id sid tid token lemma pos cord-276598-tm0yj2sn 1 1 key key NN cord-276598-tm0yj2sn 1 2 : : : cord-276598-tm0yj2sn 2 1 cord-276598-tm0yj2sn cord-276598-tm0yj2sn JJ cord-276598-tm0yj2sn 2 2 authors author NNS cord-276598-tm0yj2sn 2 3 : : : cord-276598-tm0yj2sn 2 4 Itumoh Itumoh NNP cord-276598-tm0yj2sn 2 5 , , , cord-276598-tm0yj2sn 2 6 Emeka Emeka NNP cord-276598-tm0yj2sn 2 7 J. J. NNP cord-276598-tm0yj2sn 2 8 ; ; : cord-276598-tm0yj2sn 2 9 Data Data NNP cord-276598-tm0yj2sn 2 10 , , , cord-276598-tm0yj2sn 2 11 Shailja Shailja NNP cord-276598-tm0yj2sn 2 12 ; ; : cord-276598-tm0yj2sn 2 13 Leitao Leitao NNP cord-276598-tm0yj2sn 2 14 , , , cord-276598-tm0yj2sn 2 15 Erin Erin NNP cord-276598-tm0yj2sn 2 16 M. M. NNP cord-276598-tm0yj2sn 2 17 title title NN cord-276598-tm0yj2sn 2 18 : : : cord-276598-tm0yj2sn 2 19 Opening open VBG cord-276598-tm0yj2sn 2 20 up up RP cord-276598-tm0yj2sn 2 21 the the DT cord-276598-tm0yj2sn 2 22 Toolbox Toolbox NNP cord-276598-tm0yj2sn 2 23 : : : cord-276598-tm0yj2sn 2 24 Synthesis Synthesis NNP cord-276598-tm0yj2sn 2 25 and and CC cord-276598-tm0yj2sn 2 26 Mechanisms Mechanisms NNPS cord-276598-tm0yj2sn 2 27 of of IN cord-276598-tm0yj2sn 2 28 Phosphoramidates Phosphoramidates NNP cord-276598-tm0yj2sn 2 29 date date NN cord-276598-tm0yj2sn 2 30 : : : cord-276598-tm0yj2sn 2 31 2020 2020 CD cord-276598-tm0yj2sn 2 32 - - HYPH cord-276598-tm0yj2sn 2 33 08 08 CD cord-276598-tm0yj2sn 2 34 - - SYM cord-276598-tm0yj2sn 2 35 13 13 CD cord-276598-tm0yj2sn 2 36 journal journal NN cord-276598-tm0yj2sn 2 37 : : : cord-276598-tm0yj2sn 3 1 Molecules molecule NNS cord-276598-tm0yj2sn 3 2 DOI DOI NNP cord-276598-tm0yj2sn 3 3 : : : cord-276598-tm0yj2sn 4 1 10.3390 10.3390 CD cord-276598-tm0yj2sn 4 2 / / SYM cord-276598-tm0yj2sn 4 3 molecules25163684 molecules25163684 NNP cord-276598-tm0yj2sn 4 4 sha sha NNP cord-276598-tm0yj2sn 4 5 : : : cord-276598-tm0yj2sn 4 6 d3d24004f408ad6be8dc1817af80e0f40510d212 d3d24004f408ad6be8dc1817af80e0f40510d212 NNP cord-276598-tm0yj2sn 4 7 doc_id doc_id CD cord-276598-tm0yj2sn 4 8 : : : cord-276598-tm0yj2sn 4 9 276598 276598 CD cord-276598-tm0yj2sn 4 10 cord_uid cord_uid NNS cord-276598-tm0yj2sn 4 11 : : : cord-276598-tm0yj2sn 5 1 tm0yj2sn tm0yj2sn NN cord-276598-tm0yj2sn 6 1 This this DT cord-276598-tm0yj2sn 6 2 review review NN cord-276598-tm0yj2sn 6 3 covers cover VBZ cord-276598-tm0yj2sn 6 4 the the DT cord-276598-tm0yj2sn 6 5 main main JJ cord-276598-tm0yj2sn 6 6 synthetic synthetic JJ cord-276598-tm0yj2sn 6 7 routes route NNS cord-276598-tm0yj2sn 6 8 to to IN cord-276598-tm0yj2sn 6 9 and and CC cord-276598-tm0yj2sn 6 10 the the DT cord-276598-tm0yj2sn 6 11 corresponding correspond VBG cord-276598-tm0yj2sn 6 12 mechanisms mechanism NNS cord-276598-tm0yj2sn 6 13 of of IN cord-276598-tm0yj2sn 6 14 phosphoramidate phosphoramidate NN cord-276598-tm0yj2sn 6 15 formation formation NN cord-276598-tm0yj2sn 6 16 . . . cord-276598-tm0yj2sn 7 1 The the DT cord-276598-tm0yj2sn 7 2 synthetic synthetic JJ cord-276598-tm0yj2sn 7 3 routes route NNS cord-276598-tm0yj2sn 7 4 can can MD cord-276598-tm0yj2sn 7 5 be be VB cord-276598-tm0yj2sn 7 6 separated separate VBN cord-276598-tm0yj2sn 7 7 into into IN cord-276598-tm0yj2sn 7 8 six six CD cord-276598-tm0yj2sn 7 9 categories category NNS cord-276598-tm0yj2sn 7 10 : : : cord-276598-tm0yj2sn 7 11 salt salt NN cord-276598-tm0yj2sn 7 12 elimination elimination NN cord-276598-tm0yj2sn 7 13 , , , cord-276598-tm0yj2sn 7 14 oxidative oxidative JJ cord-276598-tm0yj2sn 7 15 cross cross NN cord-276598-tm0yj2sn 7 16 - - NN cord-276598-tm0yj2sn 7 17 coupling coupling JJ cord-276598-tm0yj2sn 7 18 , , , cord-276598-tm0yj2sn 7 19 azide azide NN cord-276598-tm0yj2sn 7 20 , , , cord-276598-tm0yj2sn 7 21 reduction reduction NN cord-276598-tm0yj2sn 7 22 , , , cord-276598-tm0yj2sn 7 23 hydrophosphinylation hydrophosphinylation NN cord-276598-tm0yj2sn 7 24 , , , cord-276598-tm0yj2sn 7 25 and and CC cord-276598-tm0yj2sn 7 26 phosphoramidate phosphoramidate NN cord-276598-tm0yj2sn 7 27 - - HYPH cord-276598-tm0yj2sn 7 28 aldehyde aldehyde NN cord-276598-tm0yj2sn 7 29 - - HYPH cord-276598-tm0yj2sn 7 30 dienophile dienophile NN cord-276598-tm0yj2sn 7 31 ( ( -LRB- cord-276598-tm0yj2sn 7 32 PAD pad NN cord-276598-tm0yj2sn 7 33 ) ) -RRB- cord-276598-tm0yj2sn 7 34 . . . cord-276598-tm0yj2sn 8 1 Examples example NNS cord-276598-tm0yj2sn 8 2 of of IN cord-276598-tm0yj2sn 8 3 some some DT cord-276598-tm0yj2sn 8 4 important important JJ cord-276598-tm0yj2sn 8 5 compounds compound NNS cord-276598-tm0yj2sn 8 6 synthesized synthesize VBN cord-276598-tm0yj2sn 8 7 through through IN cord-276598-tm0yj2sn 8 8 these these DT cord-276598-tm0yj2sn 8 9 routes route NNS cord-276598-tm0yj2sn 8 10 are be VBP cord-276598-tm0yj2sn 8 11 provided provide VBN cord-276598-tm0yj2sn 8 12 . . . cord-276598-tm0yj2sn 9 1 As as IN cord-276598-tm0yj2sn 9 2 an an DT cord-276598-tm0yj2sn 9 3 important important JJ cord-276598-tm0yj2sn 9 4 class class NN cord-276598-tm0yj2sn 9 5 of of IN cord-276598-tm0yj2sn 9 6 organophosphorus organophosphorus JJ cord-276598-tm0yj2sn 9 7 compounds compound NNS cord-276598-tm0yj2sn 9 8 , , , cord-276598-tm0yj2sn 9 9 the the DT cord-276598-tm0yj2sn 9 10 applications application NNS cord-276598-tm0yj2sn 9 11 of of IN cord-276598-tm0yj2sn 9 12 phosphoramidate phosphoramidate NN cord-276598-tm0yj2sn 9 13 compounds compound NNS cord-276598-tm0yj2sn 9 14 , , , cord-276598-tm0yj2sn 9 15 are be VBP cord-276598-tm0yj2sn 9 16 also also RB cord-276598-tm0yj2sn 9 17 briefly briefly RB cord-276598-tm0yj2sn 9 18 introduced introduce VBN cord-276598-tm0yj2sn 9 19 . . . cord-276598-tm0yj2sn 10 1 Phosphoramidates Phosphoramidates NNP cord-276598-tm0yj2sn 10 2 ( ( -LRB- cord-276598-tm0yj2sn 10 3 P P NNP cord-276598-tm0yj2sn 10 4 - - HYPH cord-276598-tm0yj2sn 10 5 N N NNP cord-276598-tm0yj2sn 10 6 ) ) -RRB- cord-276598-tm0yj2sn 10 7 are be VBP cord-276598-tm0yj2sn 10 8 a a DT cord-276598-tm0yj2sn 10 9 class class NN cord-276598-tm0yj2sn 10 10 of of IN cord-276598-tm0yj2sn 10 11 organophosphorus organophosphorus JJ cord-276598-tm0yj2sn 10 12 compounds compound NNS cord-276598-tm0yj2sn 10 13 known know VBN cord-276598-tm0yj2sn 10 14 for for IN cord-276598-tm0yj2sn 10 15 the the DT cord-276598-tm0yj2sn 10 16 presence presence NN cord-276598-tm0yj2sn 10 17 of of IN cord-276598-tm0yj2sn 10 18 a a DT cord-276598-tm0yj2sn 10 19 single single JJ cord-276598-tm0yj2sn 10 20 covalent covalent JJ cord-276598-tm0yj2sn 10 21 bond bond NN cord-276598-tm0yj2sn 10 22 between between IN cord-276598-tm0yj2sn 10 23 the the DT cord-276598-tm0yj2sn 10 24 tetracoordinate tetracoordinate NN cord-276598-tm0yj2sn 11 1 P(V P(V NNP cord-276598-tm0yj2sn 11 2 ) ) -RRB- cord-276598-tm0yj2sn 11 3 atom atom NN cord-276598-tm0yj2sn 11 4 and and CC cord-276598-tm0yj2sn 11 5 N(III n(iii CD cord-276598-tm0yj2sn 11 6 ) ) -RRB- cord-276598-tm0yj2sn 11 7 atom atom NN cord-276598-tm0yj2sn 11 8 . . . cord-276598-tm0yj2sn 12 1 There there EX cord-276598-tm0yj2sn 12 2 are be VBP cord-276598-tm0yj2sn 12 3 generally generally RB cord-276598-tm0yj2sn 12 4 three three CD cord-276598-tm0yj2sn 12 5 types type NNS cord-276598-tm0yj2sn 12 6 of of IN cord-276598-tm0yj2sn 12 7 phosphoroamidates phosphoroamidate NNS cord-276598-tm0yj2sn 12 8 , , , cord-276598-tm0yj2sn 12 9 which which WDT cord-276598-tm0yj2sn 12 10 are be VBP cord-276598-tm0yj2sn 12 11 distinguished distinguish VBN cord-276598-tm0yj2sn 12 12 according accord VBG cord-276598-tm0yj2sn 12 13 to to IN cord-276598-tm0yj2sn 12 14 the the DT cord-276598-tm0yj2sn 12 15 substitution substitution NN cord-276598-tm0yj2sn 12 16 on on IN cord-276598-tm0yj2sn 12 17 the the DT cord-276598-tm0yj2sn 12 18 P p NN cord-276598-tm0yj2sn 12 19 and and CC cord-276598-tm0yj2sn 12 20 N n CD cord-276598-tm0yj2sn 12 21 atoms atom NNS cord-276598-tm0yj2sn 12 22 ( ( -LRB- cord-276598-tm0yj2sn 12 23 Figure figure NN cord-276598-tm0yj2sn 12 24 1 1 CD cord-276598-tm0yj2sn 12 25 ) ) -RRB- cord-276598-tm0yj2sn 12 26 [ [ -LRB- cord-276598-tm0yj2sn 12 27 1 1 CD cord-276598-tm0yj2sn 12 28 ] ] -RRB- cord-276598-tm0yj2sn 12 29 . . . cord-276598-tm0yj2sn 13 1 Another another DT cord-276598-tm0yj2sn 13 2 feature feature NN cord-276598-tm0yj2sn 13 3 of of IN cord-276598-tm0yj2sn 13 4 these these DT cord-276598-tm0yj2sn 13 5 organophosphorous organophosphorous JJ cord-276598-tm0yj2sn 13 6 compounds compound NNS cord-276598-tm0yj2sn 13 7 , , , cord-276598-tm0yj2sn 13 8 defined define VBN cord-276598-tm0yj2sn 13 9 as as IN cord-276598-tm0yj2sn 13 10 ( ( -LRB- cord-276598-tm0yj2sn 13 11 RO)2P(O)NR'2 RO)2P(O)NR'2 NNP cord-276598-tm0yj2sn 13 12 ( ( -LRB- cord-276598-tm0yj2sn 13 13 R r NN cord-276598-tm0yj2sn 13 14 , , , cord-276598-tm0yj2sn 13 15 R r NN cord-276598-tm0yj2sn 13 16 ' ' '' cord-276598-tm0yj2sn 14 1 = = SYM cord-276598-tm0yj2sn 14 2 H h NN cord-276598-tm0yj2sn 14 3 , , , cord-276598-tm0yj2sn 14 4 alkyl alkyl NN cord-276598-tm0yj2sn 14 5 , , , cord-276598-tm0yj2sn 14 6 aryl aryl NN cord-276598-tm0yj2sn 14 7 , , , cord-276598-tm0yj2sn 14 8 heteroaryl heteroaryl NNP cord-276598-tm0yj2sn 14 9 ) ) -RRB- cord-276598-tm0yj2sn 14 10 , , , cord-276598-tm0yj2sn 14 11 is be VBZ cord-276598-tm0yj2sn 14 12 a a DT cord-276598-tm0yj2sn 14 13 stable stable JJ cord-276598-tm0yj2sn 14 14 phosphoryl phosphoryl NN cord-276598-tm0yj2sn 14 15 bond bond NN cord-276598-tm0yj2sn 14 16 ( ( -LRB- cord-276598-tm0yj2sn 14 17 P p NN cord-276598-tm0yj2sn 14 18 = = SYM cord-276598-tm0yj2sn 14 19 O o NN cord-276598-tm0yj2sn 14 20 ) ) -RRB- cord-276598-tm0yj2sn 14 21 . . . cord-276598-tm0yj2sn 15 1 Both both DT cord-276598-tm0yj2sn 15 2 P p NN cord-276598-tm0yj2sn 15 3 and and CC cord-276598-tm0yj2sn 15 4 N n CD cord-276598-tm0yj2sn 15 5 atoms atom NNS cord-276598-tm0yj2sn 15 6 are be VBP cord-276598-tm0yj2sn 15 7 key key JJ cord-276598-tm0yj2sn 15 8 physiological physiological JJ cord-276598-tm0yj2sn 15 9 elements element NNS cord-276598-tm0yj2sn 15 10 present present JJ cord-276598-tm0yj2sn 15 11 in in IN cord-276598-tm0yj2sn 15 12 genetic genetic JJ cord-276598-tm0yj2sn 15 13 material material NN cord-276598-tm0yj2sn 15 14 , , , cord-276598-tm0yj2sn 15 15 energy energy NN cord-276598-tm0yj2sn 15 16 transfer transfer NN cord-276598-tm0yj2sn 15 17 , , , cord-276598-tm0yj2sn 15 18 enzymes enzyme NNS cord-276598-tm0yj2sn 15 19 , , , cord-276598-tm0yj2sn 15 20 and and CC cord-276598-tm0yj2sn 15 21 other other JJ cord-276598-tm0yj2sn 15 22 biomolecules biomolecule NNS cord-276598-tm0yj2sn 15 23 and and CC cord-276598-tm0yj2sn 15 24 are be VBP cord-276598-tm0yj2sn 15 25 required require VBN cord-276598-tm0yj2sn 15 26 for for IN cord-276598-tm0yj2sn 15 27 various various JJ cord-276598-tm0yj2sn 15 28 life life NN cord-276598-tm0yj2sn 15 29 processes process NNS cord-276598-tm0yj2sn 15 30 . . . cord-276598-tm0yj2sn 16 1 As as IN cord-276598-tm0yj2sn 16 2 such such JJ cord-276598-tm0yj2sn 16 3 , , , cord-276598-tm0yj2sn 16 4 molecules molecule NNS cord-276598-tm0yj2sn 16 5 containing contain VBG cord-276598-tm0yj2sn 16 6 P P NNP cord-276598-tm0yj2sn 16 7 - - HYPH cord-276598-tm0yj2sn 16 8 N n CD cord-276598-tm0yj2sn 16 9 linkages linkage NNS cord-276598-tm0yj2sn 16 10 are be VBP cord-276598-tm0yj2sn 16 11 found find VBN cord-276598-tm0yj2sn 16 12 in in IN cord-276598-tm0yj2sn 16 13 a a DT cord-276598-tm0yj2sn 16 14 large large JJ cord-276598-tm0yj2sn 16 15 array array NN cord-276598-tm0yj2sn 16 16 of of IN cord-276598-tm0yj2sn 16 17 biologically biologically RB cord-276598-tm0yj2sn 16 18 active active JJ cord-276598-tm0yj2sn 16 19 natural natural JJ cord-276598-tm0yj2sn 16 20 products product NNS cord-276598-tm0yj2sn 16 21 ( ( -LRB- cord-276598-tm0yj2sn 16 22 1 1 CD cord-276598-tm0yj2sn 16 23 - - SYM cord-276598-tm0yj2sn 16 24 7 7 CD cord-276598-tm0yj2sn 16 25 ) ) -RRB- cord-276598-tm0yj2sn 16 26 ( ( -LRB- cord-276598-tm0yj2sn 16 27 Figure figure NN cord-276598-tm0yj2sn 16 28 2 2 CD cord-276598-tm0yj2sn 16 29 ) ) -RRB- cord-276598-tm0yj2sn 16 30 [ [ -LRB- cord-276598-tm0yj2sn 16 31 2 2 CD cord-276598-tm0yj2sn 16 32 , , , cord-276598-tm0yj2sn 16 33 3 3 CD cord-276598-tm0yj2sn 16 34 ] ] -RRB- cord-276598-tm0yj2sn 16 35 . . . cord-276598-tm0yj2sn 17 1 For for IN cord-276598-tm0yj2sn 17 2 example example NN cord-276598-tm0yj2sn 17 3 , , , cord-276598-tm0yj2sn 17 4 Microcin Microcin NNP cord-276598-tm0yj2sn 17 5 C7 C7 NNP cord-276598-tm0yj2sn 17 6 ( ( -LRB- cord-276598-tm0yj2sn 17 7 1 1 CD cord-276598-tm0yj2sn 17 8 ) ) -RRB- cord-276598-tm0yj2sn 17 9 ( ( -LRB- cord-276598-tm0yj2sn 17 10 Figure figure NN cord-276598-tm0yj2sn 17 11 2 2 CD cord-276598-tm0yj2sn 17 12 ) ) -RRB- cord-276598-tm0yj2sn 17 13 is be VBZ cord-276598-tm0yj2sn 17 14 an an DT cord-276598-tm0yj2sn 17 15 antibiotic antibiotic NN cord-276598-tm0yj2sn 17 16 produced produce VBN cord-276598-tm0yj2sn 17 17 by by IN cord-276598-tm0yj2sn 17 18 Escherichia Escherichia NNP cord-276598-tm0yj2sn 17 19 coli coli NNS cord-276598-tm0yj2sn 17 20 [ [ -LRB- cord-276598-tm0yj2sn 17 21 4 4 CD cord-276598-tm0yj2sn 17 22 ] ] -RRB- cord-276598-tm0yj2sn 17 23 . . . cord-276598-tm0yj2sn 18 1 Dinogunellin Dinogunellin NNP cord-276598-tm0yj2sn 18 2 ( ( -LRB- cord-276598-tm0yj2sn 18 3 2 2 LS cord-276598-tm0yj2sn 18 4 ) ) -RRB- cord-276598-tm0yj2sn 18 5 ( ( -LRB- cord-276598-tm0yj2sn 18 6 Figure figure NN cord-276598-tm0yj2sn 18 7 2 2 CD cord-276598-tm0yj2sn 18 8 ) ) -RRB- cord-276598-tm0yj2sn 18 9 , , , cord-276598-tm0yj2sn 18 10 which which WDT cord-276598-tm0yj2sn 18 11 is be VBZ cord-276598-tm0yj2sn 18 12 produced produce VBN cord-276598-tm0yj2sn 18 13 in in IN cord-276598-tm0yj2sn 18 14 the the DT cord-276598-tm0yj2sn 18 15 roe roe NN cord-276598-tm0yj2sn 18 16 of of IN cord-276598-tm0yj2sn 18 17 some some DT cord-276598-tm0yj2sn 18 18 fishes fish NNS cord-276598-tm0yj2sn 18 19 , , , cord-276598-tm0yj2sn 18 20 is be VBZ cord-276598-tm0yj2sn 18 21 a a DT cord-276598-tm0yj2sn 18 22 natural natural JJ cord-276598-tm0yj2sn 18 23 toxin toxin NN cord-276598-tm0yj2sn 18 24 [ [ -LRB- cord-276598-tm0yj2sn 18 25 5 5 CD cord-276598-tm0yj2sn 18 26 ] ] -RRB- cord-276598-tm0yj2sn 18 27 . . . cord-276598-tm0yj2sn 19 1 Phosphoarginine Phosphoarginine NNP cord-276598-tm0yj2sn 19 2 and and CC cord-276598-tm0yj2sn 19 3 phosphocreatine phosphocreatine NN cord-276598-tm0yj2sn 19 4 ( ( -LRB- cord-276598-tm0yj2sn 19 5 3 3 CD cord-276598-tm0yj2sn 19 6 and and CC cord-276598-tm0yj2sn 19 7 6 6 CD cord-276598-tm0yj2sn 19 8 ) ) -RRB- cord-276598-tm0yj2sn 20 1 ( ( -LRB- cord-276598-tm0yj2sn 20 2 Figure figure NN cord-276598-tm0yj2sn 20 3 2 2 CD cord-276598-tm0yj2sn 20 4 ) ) -RRB- cord-276598-tm0yj2sn 20 5 are be VBP cord-276598-tm0yj2sn 20 6 important important JJ cord-276598-tm0yj2sn 20 7 biological biological JJ cord-276598-tm0yj2sn 20 8 molecules molecule NNS cord-276598-tm0yj2sn 20 9 used use VBN cord-276598-tm0yj2sn 20 10 as as IN cord-276598-tm0yj2sn 20 11 sources source NNS cord-276598-tm0yj2sn 20 12 of of IN cord-276598-tm0yj2sn 20 13 stored store VBN cord-276598-tm0yj2sn 20 14 energies energy NNS cord-276598-tm0yj2sn 20 15 in in IN cord-276598-tm0yj2sn 20 16 invertebrates invertebrate NNS cord-276598-tm0yj2sn 20 17 and and CC cord-276598-tm0yj2sn 20 18 vertebrates vertebrate NNS cord-276598-tm0yj2sn 20 19 , , , cord-276598-tm0yj2sn 20 20 respectively respectively RB cord-276598-tm0yj2sn 20 21 [ [ -LRB- cord-276598-tm0yj2sn 20 22 6 6 CD cord-276598-tm0yj2sn 20 23 ] ] -RRB- cord-276598-tm0yj2sn 20 24 . . . cord-276598-tm0yj2sn 21 1 Phosphoramidon Phosphoramidon NNP cord-276598-tm0yj2sn 21 2 ( ( -LRB- cord-276598-tm0yj2sn 21 3 4 4 LS cord-276598-tm0yj2sn 21 4 ) ) -RRB- cord-276598-tm0yj2sn 21 5 ( ( -LRB- cord-276598-tm0yj2sn 21 6 Figure figure NN cord-276598-tm0yj2sn 21 7 2 2 CD cord-276598-tm0yj2sn 21 8 ) ) -RRB- cord-276598-tm0yj2sn 21 9 , , , cord-276598-tm0yj2sn 21 10 derived derive VBN cord-276598-tm0yj2sn 21 11 from from IN cord-276598-tm0yj2sn 21 12 Streptomyces Streptomyces NNP cord-276598-tm0yj2sn 21 13 tanashiensis tanashiensis NN cord-276598-tm0yj2sn 21 14 , , , cord-276598-tm0yj2sn 21 15 inhibits inhibit VBZ cord-276598-tm0yj2sn 21 16 the the DT cord-276598-tm0yj2sn 21 17 thermolysin thermolysin NNP cord-276598-tm0yj2sn 21 18 enzyme enzyme NN cord-276598-tm0yj2sn 21 19 , , , cord-276598-tm0yj2sn 21 20 which which WDT cord-276598-tm0yj2sn 21 21 is be VBZ cord-276598-tm0yj2sn 21 22 a a DT cord-276598-tm0yj2sn 21 23 key key JJ cord-276598-tm0yj2sn 21 24 factor factor NN cord-276598-tm0yj2sn 21 25 in in IN cord-276598-tm0yj2sn 21 26 the the DT cord-276598-tm0yj2sn 21 27 development development NN cord-276598-tm0yj2sn 21 28 of of IN cord-276598-tm0yj2sn 21 29 various various JJ cord-276598-tm0yj2sn 21 30 diseases disease NNS cord-276598-tm0yj2sn 21 31 [ [ -LRB- cord-276598-tm0yj2sn 21 32 7 7 CD cord-276598-tm0yj2sn 21 33 , , , cord-276598-tm0yj2sn 21 34 8 8 CD cord-276598-tm0yj2sn 21 35 ] ] -RRB- cord-276598-tm0yj2sn 21 36 . . . cord-276598-tm0yj2sn 22 1 Lastly lastly RB cord-276598-tm0yj2sn 22 2 , , , cord-276598-tm0yj2sn 22 3 phosmidosine phosmidosine NNP cord-276598-tm0yj2sn 22 4 and and CC cord-276598-tm0yj2sn 22 5 agrocin agrocin NNP cord-276598-tm0yj2sn 22 6 84 84 CD cord-276598-tm0yj2sn 22 7 ( ( -LRB- cord-276598-tm0yj2sn 22 8 5 5 CD cord-276598-tm0yj2sn 22 9 and and CC cord-276598-tm0yj2sn 22 10 7 7 CD cord-276598-tm0yj2sn 22 11 ) ) -RRB- cord-276598-tm0yj2sn 22 12 ( ( -LRB- cord-276598-tm0yj2sn 22 13 Figure figure NN cord-276598-tm0yj2sn 22 14 2 2 CD cord-276598-tm0yj2sn 22 15 ) ) -RRB- cord-276598-tm0yj2sn 22 16 are be VBP cord-276598-tm0yj2sn 22 17 nucleotide nucleotide JJ cord-276598-tm0yj2sn 22 18 antibiotics antibiotic NNS cord-276598-tm0yj2sn 22 19 isolated isolate VBN cord-276598-tm0yj2sn 22 20 from from IN cord-276598-tm0yj2sn 22 21 Streptomyces Streptomyces NNP cord-276598-tm0yj2sn 22 22 durhameusis durhameusis NN cord-276598-tm0yj2sn 22 23 and and CC cord-276598-tm0yj2sn 22 24 Agrobacterium Agrobacterium NNP cord-276598-tm0yj2sn 22 25 radiobacter radiobacter NN cord-276598-tm0yj2sn 22 26 and and CC cord-276598-tm0yj2sn 22 27 are be VBP cord-276598-tm0yj2sn 22 28 used use VBN cord-276598-tm0yj2sn 22 29 to to TO cord-276598-tm0yj2sn 22 30 control control VB cord-276598-tm0yj2sn 22 31 gray gray JJ cord-276598-tm0yj2sn 22 32 mold mold NN cord-276598-tm0yj2sn 22 33 disease disease NN cord-276598-tm0yj2sn 22 34 and and CC cord-276598-tm0yj2sn 22 35 crown crown NN cord-276598-tm0yj2sn 22 36 gall gall NN cord-276598-tm0yj2sn 22 37 disease disease NN cord-276598-tm0yj2sn 22 38 in in IN cord-276598-tm0yj2sn 22 39 plants plant NNS cord-276598-tm0yj2sn 22 40 , , , cord-276598-tm0yj2sn 22 41 respectively respectively RB cord-276598-tm0yj2sn 22 42 [ [ -LRB- cord-276598-tm0yj2sn 22 43 9 9 CD cord-276598-tm0yj2sn 22 44 , , , cord-276598-tm0yj2sn 22 45 10 10 CD cord-276598-tm0yj2sn 22 46 ] ] -RRB- cord-276598-tm0yj2sn 22 47 . . . cord-276598-tm0yj2sn 23 1 Another another DT cord-276598-tm0yj2sn 23 2 feature feature NN cord-276598-tm0yj2sn 23 3 of of IN cord-276598-tm0yj2sn 23 4 these these DT cord-276598-tm0yj2sn 23 5 organophosphorous organophosphorous JJ cord-276598-tm0yj2sn 23 6 compounds compound NNS cord-276598-tm0yj2sn 23 7 , , , cord-276598-tm0yj2sn 23 8 defined define VBN cord-276598-tm0yj2sn 23 9 as as IN cord-276598-tm0yj2sn 23 10 ( ( -LRB- cord-276598-tm0yj2sn 23 11 RO RO NNP cord-276598-tm0yj2sn 23 12 ) ) -RRB- cord-276598-tm0yj2sn 23 13 2 2 CD cord-276598-tm0yj2sn 23 14 P(O)NR p(o)nr NN cord-276598-tm0yj2sn 23 15 ' ' POS cord-276598-tm0yj2sn 23 16 2 2 CD cord-276598-tm0yj2sn 23 17 ( ( -LRB- cord-276598-tm0yj2sn 23 18 R r NN cord-276598-tm0yj2sn 23 19 , , , cord-276598-tm0yj2sn 23 20 R r NN cord-276598-tm0yj2sn 23 21 ' ' '' cord-276598-tm0yj2sn 23 22 = = NN cord-276598-tm0yj2sn 23 23 H h NN cord-276598-tm0yj2sn 23 24 , , , cord-276598-tm0yj2sn 23 25 alkyl alkyl NN cord-276598-tm0yj2sn 23 26 , , , cord-276598-tm0yj2sn 23 27 aryl aryl NN cord-276598-tm0yj2sn 23 28 , , , cord-276598-tm0yj2sn 23 29 heteroaryl heteroaryl NNP cord-276598-tm0yj2sn 23 30 ) ) -RRB- cord-276598-tm0yj2sn 23 31 , , , cord-276598-tm0yj2sn 23 32 is be VBZ cord-276598-tm0yj2sn 23 33 a a DT cord-276598-tm0yj2sn 23 34 stable stable JJ cord-276598-tm0yj2sn 23 35 phosphoryl phosphoryl NN cord-276598-tm0yj2sn 23 36 bond bond NN cord-276598-tm0yj2sn 23 37 ( ( -LRB- cord-276598-tm0yj2sn 23 38 P p NN cord-276598-tm0yj2sn 23 39 = = SYM cord-276598-tm0yj2sn 23 40 O o NN cord-276598-tm0yj2sn 23 41 ) ) -RRB- cord-276598-tm0yj2sn 23 42 . . . cord-276598-tm0yj2sn 24 1 Both both DT cord-276598-tm0yj2sn 24 2 P p NN cord-276598-tm0yj2sn 24 3 and and CC cord-276598-tm0yj2sn 24 4 N n CD cord-276598-tm0yj2sn 24 5 atoms atom NNS cord-276598-tm0yj2sn 24 6 are be VBP cord-276598-tm0yj2sn 24 7 key key JJ cord-276598-tm0yj2sn 24 8 physiological physiological JJ cord-276598-tm0yj2sn 24 9 elements element NNS cord-276598-tm0yj2sn 24 10 present present JJ cord-276598-tm0yj2sn 24 11 in in IN cord-276598-tm0yj2sn 24 12 genetic genetic JJ cord-276598-tm0yj2sn 24 13 material material NN cord-276598-tm0yj2sn 24 14 , , , cord-276598-tm0yj2sn 24 15 energy energy NN cord-276598-tm0yj2sn 24 16 transfer transfer NN cord-276598-tm0yj2sn 24 17 , , , cord-276598-tm0yj2sn 24 18 enzymes enzyme NNS cord-276598-tm0yj2sn 24 19 , , , cord-276598-tm0yj2sn 24 20 and and CC cord-276598-tm0yj2sn 24 21 other other JJ cord-276598-tm0yj2sn 24 22 biomolecules biomolecule NNS cord-276598-tm0yj2sn 24 23 and and CC cord-276598-tm0yj2sn 24 24 are be VBP cord-276598-tm0yj2sn 24 25 required require VBN cord-276598-tm0yj2sn 24 26 for for IN cord-276598-tm0yj2sn 24 27 various various JJ cord-276598-tm0yj2sn 24 28 life life NN cord-276598-tm0yj2sn 24 29 processes process NNS cord-276598-tm0yj2sn 24 30 . . . cord-276598-tm0yj2sn 25 1 As as IN cord-276598-tm0yj2sn 25 2 such such JJ cord-276598-tm0yj2sn 25 3 , , , cord-276598-tm0yj2sn 25 4 molecules molecule NNS cord-276598-tm0yj2sn 25 5 containing contain VBG cord-276598-tm0yj2sn 25 6 P P NNP cord-276598-tm0yj2sn 25 7 - - HYPH cord-276598-tm0yj2sn 25 8 N n CD cord-276598-tm0yj2sn 25 9 linkages linkage NNS cord-276598-tm0yj2sn 25 10 are be VBP cord-276598-tm0yj2sn 25 11 found find VBN cord-276598-tm0yj2sn 25 12 in in IN cord-276598-tm0yj2sn 25 13 a a DT cord-276598-tm0yj2sn 25 14 large large JJ cord-276598-tm0yj2sn 25 15 array array NN cord-276598-tm0yj2sn 25 16 of of IN cord-276598-tm0yj2sn 25 17 biologically biologically RB cord-276598-tm0yj2sn 25 18 active active JJ cord-276598-tm0yj2sn 25 19 natural natural JJ cord-276598-tm0yj2sn 25 20 products product NNS cord-276598-tm0yj2sn 25 21 ( ( -LRB- cord-276598-tm0yj2sn 25 22 1 1 CD cord-276598-tm0yj2sn 25 23 - - SYM cord-276598-tm0yj2sn 25 24 7 7 CD cord-276598-tm0yj2sn 25 25 ) ) -RRB- cord-276598-tm0yj2sn 25 26 ( ( -LRB- cord-276598-tm0yj2sn 25 27 Figure figure NN cord-276598-tm0yj2sn 25 28 2 2 CD cord-276598-tm0yj2sn 25 29 ) ) -RRB- cord-276598-tm0yj2sn 25 30 [ [ -LRB- cord-276598-tm0yj2sn 25 31 2 2 CD cord-276598-tm0yj2sn 25 32 , , , cord-276598-tm0yj2sn 25 33 3 3 CD cord-276598-tm0yj2sn 25 34 ] ] -RRB- cord-276598-tm0yj2sn 25 35 . . . cord-276598-tm0yj2sn 26 1 For for IN cord-276598-tm0yj2sn 26 2 example example NN cord-276598-tm0yj2sn 26 3 , , , cord-276598-tm0yj2sn 26 4 Microcin Microcin NNP cord-276598-tm0yj2sn 26 5 C7 C7 NNP cord-276598-tm0yj2sn 26 6 ( ( -LRB- cord-276598-tm0yj2sn 26 7 1 1 CD cord-276598-tm0yj2sn 26 8 ) ) -RRB- cord-276598-tm0yj2sn 26 9 ( ( -LRB- cord-276598-tm0yj2sn 26 10 Figure figure NN cord-276598-tm0yj2sn 26 11 2 2 CD cord-276598-tm0yj2sn 26 12 ) ) -RRB- cord-276598-tm0yj2sn 26 13 is be VBZ cord-276598-tm0yj2sn 26 14 an an DT cord-276598-tm0yj2sn 26 15 antibiotic antibiotic NN cord-276598-tm0yj2sn 26 16 produced produce VBN cord-276598-tm0yj2sn 26 17 by by IN cord-276598-tm0yj2sn 26 18 Escherichia Escherichia NNP cord-276598-tm0yj2sn 26 19 coli coli NNS cord-276598-tm0yj2sn 26 20 [ [ -LRB- cord-276598-tm0yj2sn 26 21 4 4 CD cord-276598-tm0yj2sn 26 22 ] ] -RRB- cord-276598-tm0yj2sn 26 23 . . . cord-276598-tm0yj2sn 27 1 Dinogunellin Dinogunellin NNP cord-276598-tm0yj2sn 27 2 ( ( -LRB- cord-276598-tm0yj2sn 27 3 2 2 LS cord-276598-tm0yj2sn 27 4 ) ) -RRB- cord-276598-tm0yj2sn 27 5 ( ( -LRB- cord-276598-tm0yj2sn 27 6 Figure figure NN cord-276598-tm0yj2sn 27 7 2 2 CD cord-276598-tm0yj2sn 27 8 ) ) -RRB- cord-276598-tm0yj2sn 27 9 , , , cord-276598-tm0yj2sn 27 10 which which WDT cord-276598-tm0yj2sn 27 11 is be VBZ cord-276598-tm0yj2sn 27 12 produced produce VBN cord-276598-tm0yj2sn 27 13 in in IN cord-276598-tm0yj2sn 27 14 the the DT cord-276598-tm0yj2sn 27 15 roe roe NN cord-276598-tm0yj2sn 27 16 of of IN cord-276598-tm0yj2sn 27 17 some some DT cord-276598-tm0yj2sn 27 18 fishes fish NNS cord-276598-tm0yj2sn 27 19 , , , cord-276598-tm0yj2sn 27 20 is be VBZ cord-276598-tm0yj2sn 27 21 a a DT cord-276598-tm0yj2sn 27 22 natural natural JJ cord-276598-tm0yj2sn 27 23 toxin toxin NN cord-276598-tm0yj2sn 27 24 [ [ -LRB- cord-276598-tm0yj2sn 27 25 5 5 CD cord-276598-tm0yj2sn 27 26 ] ] -RRB- cord-276598-tm0yj2sn 27 27 . . . cord-276598-tm0yj2sn 28 1 Phosphoarginine Phosphoarginine NNP cord-276598-tm0yj2sn 28 2 and and CC cord-276598-tm0yj2sn 28 3 phosphocreatine phosphocreatine NN cord-276598-tm0yj2sn 28 4 ( ( -LRB- cord-276598-tm0yj2sn 28 5 3 3 CD cord-276598-tm0yj2sn 28 6 and and CC cord-276598-tm0yj2sn 28 7 6 6 CD cord-276598-tm0yj2sn 28 8 ) ) -RRB- cord-276598-tm0yj2sn 29 1 ( ( -LRB- cord-276598-tm0yj2sn 29 2 Figure figure NN cord-276598-tm0yj2sn 29 3 2 2 CD cord-276598-tm0yj2sn 29 4 ) ) -RRB- cord-276598-tm0yj2sn 29 5 are be VBP cord-276598-tm0yj2sn 29 6 important important JJ cord-276598-tm0yj2sn 29 7 biological biological JJ cord-276598-tm0yj2sn 29 8 molecules molecule NNS cord-276598-tm0yj2sn 29 9 used use VBN cord-276598-tm0yj2sn 29 10 as as IN cord-276598-tm0yj2sn 29 11 sources source NNS cord-276598-tm0yj2sn 29 12 of of IN cord-276598-tm0yj2sn 29 13 stored store VBN cord-276598-tm0yj2sn 29 14 energies energy NNS cord-276598-tm0yj2sn 29 15 in in IN cord-276598-tm0yj2sn 29 16 invertebrates invertebrate NNS cord-276598-tm0yj2sn 29 17 and and CC cord-276598-tm0yj2sn 29 18 vertebrates vertebrate NNS cord-276598-tm0yj2sn 29 19 , , , cord-276598-tm0yj2sn 29 20 respectively respectively RB cord-276598-tm0yj2sn 29 21 [ [ -LRB- cord-276598-tm0yj2sn 29 22 6 6 CD cord-276598-tm0yj2sn 29 23 ] ] -RRB- cord-276598-tm0yj2sn 29 24 . . . cord-276598-tm0yj2sn 30 1 Phosphoramidon Phosphoramidon NNP cord-276598-tm0yj2sn 30 2 ( ( -LRB- cord-276598-tm0yj2sn 30 3 4 4 LS cord-276598-tm0yj2sn 30 4 ) ) -RRB- cord-276598-tm0yj2sn 30 5 ( ( -LRB- cord-276598-tm0yj2sn 30 6 Figure figure NN cord-276598-tm0yj2sn 30 7 2 2 CD cord-276598-tm0yj2sn 30 8 ) ) -RRB- cord-276598-tm0yj2sn 30 9 , , , cord-276598-tm0yj2sn 30 10 derived derive VBN cord-276598-tm0yj2sn 30 11 from from IN cord-276598-tm0yj2sn 30 12 Streptomyces Streptomyces NNP cord-276598-tm0yj2sn 30 13 tanashiensis tanashiensis NN cord-276598-tm0yj2sn 30 14 , , , cord-276598-tm0yj2sn 30 15 inhibits inhibit VBZ cord-276598-tm0yj2sn 30 16 the the DT cord-276598-tm0yj2sn 30 17 thermolysin thermolysin NNP cord-276598-tm0yj2sn 30 18 enzyme enzyme NN cord-276598-tm0yj2sn 30 19 , , , cord-276598-tm0yj2sn 30 20 which which WDT cord-276598-tm0yj2sn 30 21 is be VBZ cord-276598-tm0yj2sn 30 22 a a DT cord-276598-tm0yj2sn 30 23 key key JJ cord-276598-tm0yj2sn 30 24 factor factor NN cord-276598-tm0yj2sn 30 25 in in IN cord-276598-tm0yj2sn 30 26 the the DT cord-276598-tm0yj2sn 30 27 development development NN cord-276598-tm0yj2sn 30 28 of of IN cord-276598-tm0yj2sn 30 29 various various JJ cord-276598-tm0yj2sn 30 30 diseases disease NNS cord-276598-tm0yj2sn 30 31 [ [ -LRB- cord-276598-tm0yj2sn 30 32 7 7 CD cord-276598-tm0yj2sn 30 33 , , , cord-276598-tm0yj2sn 30 34 8 8 CD cord-276598-tm0yj2sn 30 35 ] ] -RRB- cord-276598-tm0yj2sn 30 36 . . . cord-276598-tm0yj2sn 31 1 Lastly lastly RB cord-276598-tm0yj2sn 31 2 , , , cord-276598-tm0yj2sn 31 3 phosmidosine phosmidosine NNP cord-276598-tm0yj2sn 31 4 and and CC cord-276598-tm0yj2sn 31 5 agrocin agrocin NNP cord-276598-tm0yj2sn 31 6 84 84 CD cord-276598-tm0yj2sn 31 7 ( ( -LRB- cord-276598-tm0yj2sn 31 8 5 5 CD cord-276598-tm0yj2sn 31 9 and and CC cord-276598-tm0yj2sn 31 10 7 7 CD cord-276598-tm0yj2sn 31 11 ) ) -RRB- cord-276598-tm0yj2sn 31 12 ( ( -LRB- cord-276598-tm0yj2sn 31 13 Figure figure NN cord-276598-tm0yj2sn 31 14 2 2 CD cord-276598-tm0yj2sn 31 15 ) ) -RRB- cord-276598-tm0yj2sn 31 16 are be VBP cord-276598-tm0yj2sn 31 17 nucleotide nucleotide JJ cord-276598-tm0yj2sn 31 18 antibiotics antibiotic NNS cord-276598-tm0yj2sn 31 19 isolated isolate VBN cord-276598-tm0yj2sn 31 20 from from IN cord-276598-tm0yj2sn 31 21 Streptomyces Streptomyces NNP cord-276598-tm0yj2sn 31 22 Due due IN cord-276598-tm0yj2sn 31 23 to to IN cord-276598-tm0yj2sn 31 24 the the DT cord-276598-tm0yj2sn 31 25 inherent inherent JJ cord-276598-tm0yj2sn 31 26 physiochemical physiochemical JJ cord-276598-tm0yj2sn 31 27 properties property NNS cord-276598-tm0yj2sn 31 28 of of IN cord-276598-tm0yj2sn 31 29 the the DT cord-276598-tm0yj2sn 31 30 phosphorus phosphorus NN cord-276598-tm0yj2sn 31 31 atom atom NN cord-276598-tm0yj2sn 31 32 including include VBG cord-276598-tm0yj2sn 31 33 its -PRON- PRP$ cord-276598-tm0yj2sn 31 34 polarizability polarizability NN cord-276598-tm0yj2sn 31 35 , , , cord-276598-tm0yj2sn 31 36 multivalency multivalency NN cord-276598-tm0yj2sn 31 37 , , , cord-276598-tm0yj2sn 31 38 varying vary VBG cord-276598-tm0yj2sn 31 39 oxidation oxidation NN cord-276598-tm0yj2sn 31 40 states state NNS cord-276598-tm0yj2sn 31 41 , , , cord-276598-tm0yj2sn 31 42 and and CC cord-276598-tm0yj2sn 31 43 low low JJ cord-276598-tm0yj2sn 31 44 coordination coordination NN cord-276598-tm0yj2sn 31 45 number number NN cord-276598-tm0yj2sn 31 46 , , , cord-276598-tm0yj2sn 31 47 a a DT cord-276598-tm0yj2sn 31 48 diverse diverse JJ cord-276598-tm0yj2sn 31 49 range range NN cord-276598-tm0yj2sn 31 50 of of IN cord-276598-tm0yj2sn 31 51 compounds compound NNS cord-276598-tm0yj2sn 31 52 containing contain VBG cord-276598-tm0yj2sn 31 53 the the DT cord-276598-tm0yj2sn 31 54 P P NNP cord-276598-tm0yj2sn 31 55 - - HYPH cord-276598-tm0yj2sn 31 56 N n CD cord-276598-tm0yj2sn 31 57 motifs motif NNS cord-276598-tm0yj2sn 31 58 have have VBP cord-276598-tm0yj2sn 31 59 been be VBN cord-276598-tm0yj2sn 31 60 synthesized synthesize VBN cord-276598-tm0yj2sn 31 61 [ [ -LRB- cord-276598-tm0yj2sn 31 62 11 11 CD cord-276598-tm0yj2sn 31 63 ] ] -RRB- cord-276598-tm0yj2sn 31 64 . . . cord-276598-tm0yj2sn 32 1 These these DT cord-276598-tm0yj2sn 32 2 P P NNP cord-276598-tm0yj2sn 32 3 - - HYPH cord-276598-tm0yj2sn 32 4 Ns Ns NNP cord-276598-tm0yj2sn 32 5 are be VBP cord-276598-tm0yj2sn 32 6 widely widely RB cord-276598-tm0yj2sn 32 7 used use VBN cord-276598-tm0yj2sn 32 8 in in IN cord-276598-tm0yj2sn 32 9 medicine medicine NN cord-276598-tm0yj2sn 32 10 for for IN cord-276598-tm0yj2sn 32 11 the the DT cord-276598-tm0yj2sn 32 12 control control NN cord-276598-tm0yj2sn 32 13 and and CC cord-276598-tm0yj2sn 32 14 treatment treatment NN cord-276598-tm0yj2sn 32 15 of of IN cord-276598-tm0yj2sn 32 16 various various JJ cord-276598-tm0yj2sn 32 17 diseases disease NNS cord-276598-tm0yj2sn 32 18 , , , cord-276598-tm0yj2sn 32 19 in in IN cord-276598-tm0yj2sn 32 20 agriculture agriculture NN cord-276598-tm0yj2sn 32 21 as as IN cord-276598-tm0yj2sn 32 22 pesticides pesticide NNS cord-276598-tm0yj2sn 32 23 for for IN cord-276598-tm0yj2sn 32 24 crop crop NN cord-276598-tm0yj2sn 32 25 protection protection NN cord-276598-tm0yj2sn 32 26 , , , cord-276598-tm0yj2sn 32 27 in in IN cord-276598-tm0yj2sn 32 28 industry industry NN cord-276598-tm0yj2sn 32 29 as as IN cord-276598-tm0yj2sn 32 30 novel novel JJ cord-276598-tm0yj2sn 32 31 fire fire NN cord-276598-tm0yj2sn 32 32 - - HYPH cord-276598-tm0yj2sn 32 33 retardant retardant NN cord-276598-tm0yj2sn 32 34 compounds compound NNS cord-276598-tm0yj2sn 32 35 to to TO cord-276598-tm0yj2sn 32 36 delay delay VB cord-276598-tm0yj2sn 32 37 the the DT cord-276598-tm0yj2sn 32 38 flammability flammability NN cord-276598-tm0yj2sn 32 39 of of IN cord-276598-tm0yj2sn 32 40 polymeric polymeric JJ cord-276598-tm0yj2sn 32 41 compounds compound NNS cord-276598-tm0yj2sn 32 42 , , , cord-276598-tm0yj2sn 32 43 and and CC cord-276598-tm0yj2sn 32 44 in in IN cord-276598-tm0yj2sn 32 45 the the DT cord-276598-tm0yj2sn 32 46 fields field NNS cord-276598-tm0yj2sn 32 47 of of IN cord-276598-tm0yj2sn 32 48 analytical analytical JJ cord-276598-tm0yj2sn 32 49 and and CC cord-276598-tm0yj2sn 32 50 coordination coordination NN cord-276598-tm0yj2sn 32 51 chemistry chemistry NN cord-276598-tm0yj2sn 32 52 . . . cord-276598-tm0yj2sn 33 1 Therefore therefore RB cord-276598-tm0yj2sn 33 2 , , , cord-276598-tm0yj2sn 33 3 synthetic synthetic JJ cord-276598-tm0yj2sn 33 4 P p NN cord-276598-tm0yj2sn 33 5 - - HYPH cord-276598-tm0yj2sn 33 6 N n CD cord-276598-tm0yj2sn 33 7 compounds compound NNS cord-276598-tm0yj2sn 33 8 are be VBP cord-276598-tm0yj2sn 33 9 not not RB cord-276598-tm0yj2sn 33 10 only only RB cord-276598-tm0yj2sn 33 11 researched research VBN cord-276598-tm0yj2sn 33 12 out out IN cord-276598-tm0yj2sn 33 13 of of IN cord-276598-tm0yj2sn 33 14 academic academic JJ cord-276598-tm0yj2sn 33 15 interest interest NN cord-276598-tm0yj2sn 33 16 , , , cord-276598-tm0yj2sn 33 17 but but CC cord-276598-tm0yj2sn 33 18 they -PRON- PRP cord-276598-tm0yj2sn 33 19 also also RB cord-276598-tm0yj2sn 33 20 have have VBP cord-276598-tm0yj2sn 33 21 commercial commercial JJ cord-276598-tm0yj2sn 33 22 applications application NNS cord-276598-tm0yj2sn 33 23 . . . cord-276598-tm0yj2sn 34 1 Uses use VBZ cord-276598-tm0yj2sn 34 2 for for IN cord-276598-tm0yj2sn 34 3 P p NN cord-276598-tm0yj2sn 34 4 - - HYPH cord-276598-tm0yj2sn 34 5 Ns Ns NNP cord-276598-tm0yj2sn 34 6 can can MD cord-276598-tm0yj2sn 34 7 be be VB cord-276598-tm0yj2sn 34 8 separated separate VBN cord-276598-tm0yj2sn 34 9 into into IN cord-276598-tm0yj2sn 34 10 5 5 CD cord-276598-tm0yj2sn 34 11 main main JJ cord-276598-tm0yj2sn 34 12 classes class NNS cord-276598-tm0yj2sn 34 13 : : : cord-276598-tm0yj2sn 34 14 agriculture agriculture NN cord-276598-tm0yj2sn 34 15 , , , cord-276598-tm0yj2sn 34 16 industry industry NN cord-276598-tm0yj2sn 34 17 , , , cord-276598-tm0yj2sn 34 18 analytical analytical JJ cord-276598-tm0yj2sn 34 19 chemistry chemistry NN cord-276598-tm0yj2sn 34 20 , , , cord-276598-tm0yj2sn 34 21 synthetic synthetic JJ cord-276598-tm0yj2sn 34 22 chemistry chemistry NN cord-276598-tm0yj2sn 34 23 , , , cord-276598-tm0yj2sn 34 24 and and CC cord-276598-tm0yj2sn 34 25 medicinal medicinal JJ cord-276598-tm0yj2sn 34 26 chemistry chemistry NN cord-276598-tm0yj2sn 34 27 ( ( -LRB- cord-276598-tm0yj2sn 34 28 Figure figure NN cord-276598-tm0yj2sn 34 29 3 3 CD cord-276598-tm0yj2sn 34 30 ) ) -RRB- cord-276598-tm0yj2sn 34 31 [ [ -LRB- cord-276598-tm0yj2sn 34 32 12 12 CD cord-276598-tm0yj2sn 34 33 ] ] -RRB- cord-276598-tm0yj2sn 34 34 [ [ -LRB- cord-276598-tm0yj2sn 34 35 13 13 CD cord-276598-tm0yj2sn 34 36 ] ] -RRB- cord-276598-tm0yj2sn 34 37 [ [ -LRB- cord-276598-tm0yj2sn 34 38 14 14 CD cord-276598-tm0yj2sn 34 39 ] ] -RRB- cord-276598-tm0yj2sn 34 40 [ [ -LRB- cord-276598-tm0yj2sn 34 41 15 15 CD cord-276598-tm0yj2sn 34 42 ] ] -RRB- cord-276598-tm0yj2sn 34 43 [ [ -LRB- cord-276598-tm0yj2sn 34 44 16 16 CD cord-276598-tm0yj2sn 34 45 ] ] -RRB- cord-276598-tm0yj2sn 34 46 [ [ -LRB- cord-276598-tm0yj2sn 34 47 17 17 CD cord-276598-tm0yj2sn 34 48 ] ] -RRB- cord-276598-tm0yj2sn 34 49 [ [ -LRB- cord-276598-tm0yj2sn 34 50 18 18 CD cord-276598-tm0yj2sn 34 51 ] ] -RRB- cord-276598-tm0yj2sn 34 52 . . . cord-276598-tm0yj2sn 34 53 _SP cord-276598-tm0yj2sn 35 1 This this DT cord-276598-tm0yj2sn 35 2 class class NN cord-276598-tm0yj2sn 35 3 of of IN cord-276598-tm0yj2sn 35 4 organophosphates organophosphate NNS cord-276598-tm0yj2sn 35 5 ( ( -LRB- cord-276598-tm0yj2sn 35 6 with with IN cord-276598-tm0yj2sn 35 7 common common JJ cord-276598-tm0yj2sn 35 8 names name NNS cord-276598-tm0yj2sn 35 9 such such JJ cord-276598-tm0yj2sn 35 10 as as IN cord-276598-tm0yj2sn 35 11 cruformate cruformate NNP cord-276598-tm0yj2sn 35 12 , , , cord-276598-tm0yj2sn 35 13 fenamiphos fenamiphos NNP cord-276598-tm0yj2sn 35 14 , , , cord-276598-tm0yj2sn 35 15 and and CC cord-276598-tm0yj2sn 35 16 fosthietan fosthietan NNP cord-276598-tm0yj2sn 35 17 ) ) -RRB- cord-276598-tm0yj2sn 35 18 has have VBZ cord-276598-tm0yj2sn 35 19 been be VBN cord-276598-tm0yj2sn 35 20 widely widely RB cord-276598-tm0yj2sn 35 21 used use VBN cord-276598-tm0yj2sn 35 22 in in IN cord-276598-tm0yj2sn 35 23 pest pest NN cord-276598-tm0yj2sn 35 24 management management NN cord-276598-tm0yj2sn 35 25 for for IN cord-276598-tm0yj2sn 35 26 crop crop NN cord-276598-tm0yj2sn 35 27 protection protection NN cord-276598-tm0yj2sn 35 28 ( ( -LRB- cord-276598-tm0yj2sn 35 29 Figure figure NN cord-276598-tm0yj2sn 35 30 3 3 CD cord-276598-tm0yj2sn 35 31 ) ) -RRB- cord-276598-tm0yj2sn 36 1 [ [ -LRB- cord-276598-tm0yj2sn 36 2 19 19 CD cord-276598-tm0yj2sn 36 3 ] ] -RRB- cord-276598-tm0yj2sn 36 4 [ [ -LRB- cord-276598-tm0yj2sn 36 5 20 20 CD cord-276598-tm0yj2sn 36 6 ] ] -RRB- cord-276598-tm0yj2sn 36 7 [ [ -LRB- cord-276598-tm0yj2sn 36 8 21 21 CD cord-276598-tm0yj2sn 36 9 ] ] -RRB- cord-276598-tm0yj2sn 36 10 . . . cord-276598-tm0yj2sn 37 1 P p NN cord-276598-tm0yj2sn 37 2 - - HYPH cord-276598-tm0yj2sn 37 3 Ns Ns NNP cord-276598-tm0yj2sn 37 4 for for IN cord-276598-tm0yj2sn 37 5 pest pest NN cord-276598-tm0yj2sn 37 6 control control NN cord-276598-tm0yj2sn 37 7 affect affect VB cord-276598-tm0yj2sn 37 8 the the DT cord-276598-tm0yj2sn 37 9 nervous nervous JJ cord-276598-tm0yj2sn 37 10 system system NN cord-276598-tm0yj2sn 37 11 of of IN cord-276598-tm0yj2sn 37 12 pests pest NNS cord-276598-tm0yj2sn 37 13 / / SYM cord-276598-tm0yj2sn 37 14 insects insect NNS cord-276598-tm0yj2sn 37 15 by by IN cord-276598-tm0yj2sn 37 16 inhibiting inhibit VBG cord-276598-tm0yj2sn 37 17 acetylcholinesterase acetylcholinesterase NN cord-276598-tm0yj2sn 37 18 ( ( -LRB- cord-276598-tm0yj2sn 37 19 AChE ache NN cord-276598-tm0yj2sn 37 20 ) ) -RRB- cord-276598-tm0yj2sn 37 21 , , , cord-276598-tm0yj2sn 37 22 a a DT cord-276598-tm0yj2sn 37 23 major major JJ cord-276598-tm0yj2sn 37 24 neurotransmitter neurotransmitter NN cord-276598-tm0yj2sn 37 25 [ [ -LRB- cord-276598-tm0yj2sn 37 26 22 22 CD cord-276598-tm0yj2sn 37 27 ] ] -RRB- cord-276598-tm0yj2sn 37 28 [ [ -LRB- cord-276598-tm0yj2sn 37 29 23 23 CD cord-276598-tm0yj2sn 37 30 ] ] -RRB- cord-276598-tm0yj2sn 37 31 [ [ -LRB- cord-276598-tm0yj2sn 37 32 24 24 CD cord-276598-tm0yj2sn 37 33 ] ] -RRB- cord-276598-tm0yj2sn 37 34 [ [ -LRB- cord-276598-tm0yj2sn 37 35 25 25 CD cord-276598-tm0yj2sn 37 36 ] ] -RRB- cord-276598-tm0yj2sn 37 37 . . . cord-276598-tm0yj2sn 38 1 In in IN cord-276598-tm0yj2sn 38 2 addition addition NN cord-276598-tm0yj2sn 38 3 , , , cord-276598-tm0yj2sn 38 4 these these DT cord-276598-tm0yj2sn 38 5 P P NNP cord-276598-tm0yj2sn 38 6 - - HYPH cord-276598-tm0yj2sn 38 7 N N NNP cord-276598-tm0yj2sn 38 8 compounds compound NNS cord-276598-tm0yj2sn 38 9 have have VBP cord-276598-tm0yj2sn 38 10 been be VBN cord-276598-tm0yj2sn 38 11 utilized utilize VBN cord-276598-tm0yj2sn 38 12 as as IN cord-276598-tm0yj2sn 38 13 urease urease NN cord-276598-tm0yj2sn 38 14 inhibitors inhibitor NNS cord-276598-tm0yj2sn 38 15 [ [ -LRB- cord-276598-tm0yj2sn 38 16 26 26 CD cord-276598-tm0yj2sn 38 17 , , , cord-276598-tm0yj2sn 38 18 27 27 CD cord-276598-tm0yj2sn 38 19 ] ] -RRB- cord-276598-tm0yj2sn 38 20 . . . cord-276598-tm0yj2sn 39 1 Urease Urease NNP cord-276598-tm0yj2sn 39 2 is be VBZ cord-276598-tm0yj2sn 39 3 a a DT cord-276598-tm0yj2sn 39 4 nickel nickel NN cord-276598-tm0yj2sn 39 5 - - HYPH cord-276598-tm0yj2sn 39 6 based base VBN cord-276598-tm0yj2sn 39 7 enzyme enzyme NN cord-276598-tm0yj2sn 39 8 that that WDT cord-276598-tm0yj2sn 39 9 catalyzes catalyze VBZ cord-276598-tm0yj2sn 39 10 the the DT cord-276598-tm0yj2sn 39 11 hydrolysis hydrolysis NN cord-276598-tm0yj2sn 39 12 of of IN cord-276598-tm0yj2sn 39 13 urea urea NN cord-276598-tm0yj2sn 39 14 on on IN cord-276598-tm0yj2sn 39 15 soil soil NN cord-276598-tm0yj2sn 39 16 surfaces surface NNS cord-276598-tm0yj2sn 39 17 into into IN cord-276598-tm0yj2sn 39 18 volatile volatile JJ cord-276598-tm0yj2sn 39 19 ammonia ammonia NN cord-276598-tm0yj2sn 39 20 and and CC cord-276598-tm0yj2sn 39 21 carbon carbon NN cord-276598-tm0yj2sn 39 22 dioxide dioxide NN cord-276598-tm0yj2sn 39 23 ( ( -LRB- cord-276598-tm0yj2sn 39 24 Scheme scheme NN cord-276598-tm0yj2sn 39 25 1 1 CD cord-276598-tm0yj2sn 39 26 ) ) -RRB- cord-276598-tm0yj2sn 39 27 [ [ -LRB- cord-276598-tm0yj2sn 39 28 28 28 CD cord-276598-tm0yj2sn 39 29 , , , cord-276598-tm0yj2sn 39 30 29 29 CD cord-276598-tm0yj2sn 39 31 ] ] -RRB- cord-276598-tm0yj2sn 39 32 . . . cord-276598-tm0yj2sn 40 1 Thus thus RB cord-276598-tm0yj2sn 40 2 , , , cord-276598-tm0yj2sn 40 3 on on IN cord-276598-tm0yj2sn 40 4 inhibiting inhibit VBG cord-276598-tm0yj2sn 40 5 the the DT cord-276598-tm0yj2sn 40 6 activity activity NN cord-276598-tm0yj2sn 40 7 of of IN cord-276598-tm0yj2sn 40 8 this this DT cord-276598-tm0yj2sn 40 9 metalloenzyme metalloenzyme NNS cord-276598-tm0yj2sn 40 10 , , , cord-276598-tm0yj2sn 40 11 the the DT cord-276598-tm0yj2sn 40 12 availability availability NN cord-276598-tm0yj2sn 40 13 and and CC cord-276598-tm0yj2sn 40 14 performance performance NN cord-276598-tm0yj2sn 40 15 of of IN cord-276598-tm0yj2sn 40 16 urea urea NN cord-276598-tm0yj2sn 40 17 is be VBZ cord-276598-tm0yj2sn 40 18 enhanced enhance VBN cord-276598-tm0yj2sn 40 19 , , , cord-276598-tm0yj2sn 40 20 which which WDT cord-276598-tm0yj2sn 40 21 is be VBZ cord-276598-tm0yj2sn 40 22 a a DT cord-276598-tm0yj2sn 40 23 vital vital JJ cord-276598-tm0yj2sn 40 24 nitrogenous nitrogenous JJ cord-276598-tm0yj2sn 40 25 fertilizer fertilizer NN cord-276598-tm0yj2sn 40 26 for for IN cord-276598-tm0yj2sn 40 27 plant plant NN cord-276598-tm0yj2sn 40 28 growth growth NN cord-276598-tm0yj2sn 40 29 . . . cord-276598-tm0yj2sn 40 30 _SP cord-276598-tm0yj2sn 41 1 P p NN cord-276598-tm0yj2sn 41 2 - - HYPH cord-276598-tm0yj2sn 41 3 Ns Ns NNP cord-276598-tm0yj2sn 41 4 have have VBP cord-276598-tm0yj2sn 41 5 been be VBN cord-276598-tm0yj2sn 41 6 used use VBN cord-276598-tm0yj2sn 41 7 as as IN cord-276598-tm0yj2sn 41 8 additives additive NNS cord-276598-tm0yj2sn 41 9 in in IN cord-276598-tm0yj2sn 41 10 both both DT cord-276598-tm0yj2sn 41 11 oil oil NN cord-276598-tm0yj2sn 41 12 and and CC cord-276598-tm0yj2sn 41 13 water water NN cord-276598-tm0yj2sn 41 14 - - HYPH cord-276598-tm0yj2sn 41 15 based base VBN cord-276598-tm0yj2sn 41 16 lubricants lubricant NNS cord-276598-tm0yj2sn 41 17 ( ( -LRB- cord-276598-tm0yj2sn 41 18 Figure figure NN cord-276598-tm0yj2sn 41 19 3 3 CD cord-276598-tm0yj2sn 41 20 ) ) -RRB- cord-276598-tm0yj2sn 41 21 . . . cord-276598-tm0yj2sn 42 1 It -PRON- PRP cord-276598-tm0yj2sn 42 2 has have VBZ cord-276598-tm0yj2sn 42 3 been be VBN cord-276598-tm0yj2sn 42 4 proposed propose VBN cord-276598-tm0yj2sn 42 5 that that IN cord-276598-tm0yj2sn 42 6 phosphorus phosphorus NN cord-276598-tm0yj2sn 42 7 acts act VBZ cord-276598-tm0yj2sn 42 8 as as IN cord-276598-tm0yj2sn 42 9 a a DT cord-276598-tm0yj2sn 42 10 key key JJ cord-276598-tm0yj2sn 42 11 element element NN cord-276598-tm0yj2sn 42 12 in in IN cord-276598-tm0yj2sn 42 13 enhancing enhance VBG cord-276598-tm0yj2sn 42 14 the the DT cord-276598-tm0yj2sn 42 15 tribological tribological NNP cord-276598-tm0yj2sn 42 16 properties property NNS cord-276598-tm0yj2sn 42 17 of of IN cord-276598-tm0yj2sn 42 18 water water NN cord-276598-tm0yj2sn 42 19 / / SYM cord-276598-tm0yj2sn 42 20 oil oil NN cord-276598-tm0yj2sn 42 21 - - HYPH cord-276598-tm0yj2sn 42 22 based base VBN cord-276598-tm0yj2sn 42 23 fluids fluid NNS cord-276598-tm0yj2sn 42 24 by by IN cord-276598-tm0yj2sn 42 25 forming form VBG cord-276598-tm0yj2sn 42 26 a a DT cord-276598-tm0yj2sn 42 27 protective protective JJ cord-276598-tm0yj2sn 42 28 layer layer NN cord-276598-tm0yj2sn 42 29 containing contain VBG cord-276598-tm0yj2sn 42 30 phosphates phosphate NNS cord-276598-tm0yj2sn 42 31 and/or and/or CC cord-276598-tm0yj2sn 42 32 polyphosphates polyphosphate NNS cord-276598-tm0yj2sn 42 33 . . . cord-276598-tm0yj2sn 43 1 Thus thus RB cord-276598-tm0yj2sn 43 2 , , , cord-276598-tm0yj2sn 43 3 they -PRON- PRP cord-276598-tm0yj2sn 43 4 possess possess VBP cord-276598-tm0yj2sn 43 5 anti anti JJ cord-276598-tm0yj2sn 43 6 - - JJ cord-276598-tm0yj2sn 43 7 wear wear JJ cord-276598-tm0yj2sn 43 8 and and CC cord-276598-tm0yj2sn 43 9 friction friction NN cord-276598-tm0yj2sn 43 10 - - HYPH cord-276598-tm0yj2sn 43 11 reducing reduce VBG cord-276598-tm0yj2sn 43 12 properties property NNS cord-276598-tm0yj2sn 43 13 [ [ -LRB- cord-276598-tm0yj2sn 43 14 18 18 CD cord-276598-tm0yj2sn 43 15 , , , cord-276598-tm0yj2sn 43 16 30 30 CD cord-276598-tm0yj2sn 43 17 ] ] -RRB- cord-276598-tm0yj2sn 43 18 . . . cord-276598-tm0yj2sn 44 1 Furthermore furthermore RB cord-276598-tm0yj2sn 44 2 , , , cord-276598-tm0yj2sn 44 3 these these DT cord-276598-tm0yj2sn 44 4 P P NNP cord-276598-tm0yj2sn 44 5 - - HYPH cord-276598-tm0yj2sn 44 6 Ns Ns NNP cord-276598-tm0yj2sn 44 7 have have VBP cord-276598-tm0yj2sn 44 8 been be VBN cord-276598-tm0yj2sn 44 9 found find VBN cord-276598-tm0yj2sn 44 10 to to TO cord-276598-tm0yj2sn 44 11 be be VB cord-276598-tm0yj2sn 44 12 a a DT cord-276598-tm0yj2sn 44 13 promising promising JJ cord-276598-tm0yj2sn 44 14 alternative alternative NN cord-276598-tm0yj2sn 44 15 to to IN cord-276598-tm0yj2sn 44 16 halogenated halogenated JJ cord-276598-tm0yj2sn 44 17 flame flame NN cord-276598-tm0yj2sn 44 18 retardants retardant NNS cord-276598-tm0yj2sn 44 19 ( ( -LRB- cord-276598-tm0yj2sn 44 20 FRs FRs NNP cord-276598-tm0yj2sn 44 21 ) ) -RRB- cord-276598-tm0yj2sn 44 22 , , , cord-276598-tm0yj2sn 44 23 which which WDT cord-276598-tm0yj2sn 44 24 are be VBP cord-276598-tm0yj2sn 44 25 being be VBG cord-276598-tm0yj2sn 44 26 phased phase VBN cord-276598-tm0yj2sn 44 27 out out RP cord-276598-tm0yj2sn 44 28 as as IN cord-276598-tm0yj2sn 44 29 they -PRON- PRP cord-276598-tm0yj2sn 44 30 have have VBP cord-276598-tm0yj2sn 44 31 been be VBN cord-276598-tm0yj2sn 44 32 recognized recognize VBN cord-276598-tm0yj2sn 44 33 as as IN cord-276598-tm0yj2sn 44 34 global global JJ cord-276598-tm0yj2sn 44 35 contaminants contaminant NNS cord-276598-tm0yj2sn 44 36 due due IN cord-276598-tm0yj2sn 44 37 to to IN cord-276598-tm0yj2sn 44 38 their -PRON- PRP$ cord-276598-tm0yj2sn 44 39 ill ill JJ cord-276598-tm0yj2sn 44 40 effects effect NNS cord-276598-tm0yj2sn 44 41 on on IN cord-276598-tm0yj2sn 44 42 health health NN cord-276598-tm0yj2sn 44 43 and and CC cord-276598-tm0yj2sn 44 44 the the DT cord-276598-tm0yj2sn 44 45 environment environment NN cord-276598-tm0yj2sn 44 46 [ [ -LRB- cord-276598-tm0yj2sn 44 47 31 31 CD cord-276598-tm0yj2sn 44 48 ] ] -RRB- cord-276598-tm0yj2sn 44 49 . . . cord-276598-tm0yj2sn 45 1 P p NN cord-276598-tm0yj2sn 45 2 - - HYPH cord-276598-tm0yj2sn 45 3 N n CD cord-276598-tm0yj2sn 45 4 fire fire NN cord-276598-tm0yj2sn 45 5 retardants retardant NNS cord-276598-tm0yj2sn 45 6 are be VBP cord-276598-tm0yj2sn 45 7 less less RBR cord-276598-tm0yj2sn 45 8 volatile volatile JJ cord-276598-tm0yj2sn 45 9 and and CC cord-276598-tm0yj2sn 45 10 relatively relatively RB cord-276598-tm0yj2sn 45 11 thermally thermally RB cord-276598-tm0yj2sn 45 12 stable stable JJ cord-276598-tm0yj2sn 45 13 with with IN cord-276598-tm0yj2sn 45 14 _SP cord-276598-tm0yj2sn 45 15 This this DT cord-276598-tm0yj2sn 45 16 class class NN cord-276598-tm0yj2sn 45 17 of of IN cord-276598-tm0yj2sn 45 18 organophosphates organophosphate NNS cord-276598-tm0yj2sn 45 19 ( ( -LRB- cord-276598-tm0yj2sn 45 20 with with IN cord-276598-tm0yj2sn 45 21 common common JJ cord-276598-tm0yj2sn 45 22 names name NNS cord-276598-tm0yj2sn 45 23 such such JJ cord-276598-tm0yj2sn 45 24 as as IN cord-276598-tm0yj2sn 45 25 cruformate cruformate NNP cord-276598-tm0yj2sn 45 26 , , , cord-276598-tm0yj2sn 45 27 fenamiphos fenamiphos NNP cord-276598-tm0yj2sn 45 28 , , , cord-276598-tm0yj2sn 45 29 and and CC cord-276598-tm0yj2sn 45 30 fosthietan fosthietan NNP cord-276598-tm0yj2sn 45 31 ) ) -RRB- cord-276598-tm0yj2sn 45 32 has have VBZ cord-276598-tm0yj2sn 45 33 been be VBN cord-276598-tm0yj2sn 45 34 widely widely RB cord-276598-tm0yj2sn 45 35 used use VBN cord-276598-tm0yj2sn 45 36 in in IN cord-276598-tm0yj2sn 45 37 pest pest NN cord-276598-tm0yj2sn 45 38 management management NN cord-276598-tm0yj2sn 45 39 for for IN cord-276598-tm0yj2sn 45 40 crop crop NN cord-276598-tm0yj2sn 45 41 protection protection NN cord-276598-tm0yj2sn 45 42 ( ( -LRB- cord-276598-tm0yj2sn 45 43 Figure figure NN cord-276598-tm0yj2sn 45 44 3 3 CD cord-276598-tm0yj2sn 45 45 ) ) -RRB- cord-276598-tm0yj2sn 45 46 [ [ -LRB- cord-276598-tm0yj2sn 45 47 19 19 CD cord-276598-tm0yj2sn 45 48 ] ] -RRB- cord-276598-tm0yj2sn 45 49 [ [ -LRB- cord-276598-tm0yj2sn 45 50 20 20 CD cord-276598-tm0yj2sn 45 51 ] ] -RRB- cord-276598-tm0yj2sn 45 52 [ [ -LRB- cord-276598-tm0yj2sn 45 53 21 21 CD cord-276598-tm0yj2sn 45 54 ] ] -RRB- cord-276598-tm0yj2sn 45 55 . . . cord-276598-tm0yj2sn 46 1 P p NN cord-276598-tm0yj2sn 46 2 - - HYPH cord-276598-tm0yj2sn 46 3 Ns Ns NNP cord-276598-tm0yj2sn 46 4 for for IN cord-276598-tm0yj2sn 46 5 pest pest NN cord-276598-tm0yj2sn 46 6 control control NN cord-276598-tm0yj2sn 46 7 affect affect VB cord-276598-tm0yj2sn 46 8 the the DT cord-276598-tm0yj2sn 46 9 nervous nervous JJ cord-276598-tm0yj2sn 46 10 system system NN cord-276598-tm0yj2sn 46 11 of of IN cord-276598-tm0yj2sn 46 12 pests pest NNS cord-276598-tm0yj2sn 46 13 / / SYM cord-276598-tm0yj2sn 46 14 insects insect NNS cord-276598-tm0yj2sn 46 15 by by IN cord-276598-tm0yj2sn 46 16 inhibiting inhibit VBG cord-276598-tm0yj2sn 46 17 acetylcholinesterase acetylcholinesterase NN cord-276598-tm0yj2sn 46 18 ( ( -LRB- cord-276598-tm0yj2sn 46 19 AChE ache NN cord-276598-tm0yj2sn 46 20 ) ) -RRB- cord-276598-tm0yj2sn 46 21 , , , cord-276598-tm0yj2sn 46 22 a a DT cord-276598-tm0yj2sn 46 23 major major JJ cord-276598-tm0yj2sn 46 24 neurotransmitter neurotransmitter NN cord-276598-tm0yj2sn 46 25 [ [ -LRB- cord-276598-tm0yj2sn 46 26 22 22 CD cord-276598-tm0yj2sn 46 27 ] ] -RRB- cord-276598-tm0yj2sn 46 28 [ [ -LRB- cord-276598-tm0yj2sn 46 29 23 23 CD cord-276598-tm0yj2sn 46 30 ] ] -RRB- cord-276598-tm0yj2sn 46 31 [ [ -LRB- cord-276598-tm0yj2sn 46 32 24 24 CD cord-276598-tm0yj2sn 46 33 ] ] -RRB- cord-276598-tm0yj2sn 46 34 [ [ -LRB- cord-276598-tm0yj2sn 46 35 25 25 CD cord-276598-tm0yj2sn 46 36 ] ] -RRB- cord-276598-tm0yj2sn 46 37 . . . cord-276598-tm0yj2sn 47 1 In in IN cord-276598-tm0yj2sn 47 2 addition addition NN cord-276598-tm0yj2sn 47 3 , , , cord-276598-tm0yj2sn 47 4 these these DT cord-276598-tm0yj2sn 47 5 P P NNP cord-276598-tm0yj2sn 47 6 - - HYPH cord-276598-tm0yj2sn 47 7 N N NNP cord-276598-tm0yj2sn 47 8 compounds compound NNS cord-276598-tm0yj2sn 47 9 have have VBP cord-276598-tm0yj2sn 47 10 been be VBN cord-276598-tm0yj2sn 47 11 utilized utilize VBN cord-276598-tm0yj2sn 47 12 as as IN cord-276598-tm0yj2sn 47 13 urease urease NN cord-276598-tm0yj2sn 47 14 inhibitors inhibitor NNS cord-276598-tm0yj2sn 47 15 [ [ -LRB- cord-276598-tm0yj2sn 47 16 26 26 CD cord-276598-tm0yj2sn 47 17 , , , cord-276598-tm0yj2sn 47 18 27 27 CD cord-276598-tm0yj2sn 47 19 ] ] -RRB- cord-276598-tm0yj2sn 47 20 . . . cord-276598-tm0yj2sn 48 1 Urease Urease NNP cord-276598-tm0yj2sn 48 2 is be VBZ cord-276598-tm0yj2sn 48 3 a a DT cord-276598-tm0yj2sn 48 4 nickel nickel NN cord-276598-tm0yj2sn 48 5 - - HYPH cord-276598-tm0yj2sn 48 6 based base VBN cord-276598-tm0yj2sn 48 7 enzyme enzyme NN cord-276598-tm0yj2sn 48 8 that that WDT cord-276598-tm0yj2sn 48 9 catalyzes catalyze VBZ cord-276598-tm0yj2sn 48 10 the the DT cord-276598-tm0yj2sn 48 11 hydrolysis hydrolysis NN cord-276598-tm0yj2sn 48 12 of of IN cord-276598-tm0yj2sn 48 13 urea urea NN cord-276598-tm0yj2sn 48 14 on on IN cord-276598-tm0yj2sn 48 15 soil soil NN cord-276598-tm0yj2sn 48 16 surfaces surface NNS cord-276598-tm0yj2sn 48 17 into into IN cord-276598-tm0yj2sn 48 18 volatile volatile JJ cord-276598-tm0yj2sn 48 19 ammonia ammonia NN cord-276598-tm0yj2sn 48 20 and and CC cord-276598-tm0yj2sn 48 21 carbon carbon NN cord-276598-tm0yj2sn 48 22 dioxide dioxide NN cord-276598-tm0yj2sn 48 23 ( ( -LRB- cord-276598-tm0yj2sn 48 24 Scheme scheme NN cord-276598-tm0yj2sn 48 25 1 1 CD cord-276598-tm0yj2sn 48 26 ) ) -RRB- cord-276598-tm0yj2sn 48 27 [ [ -LRB- cord-276598-tm0yj2sn 48 28 28 28 CD cord-276598-tm0yj2sn 48 29 , , , cord-276598-tm0yj2sn 48 30 29 29 CD cord-276598-tm0yj2sn 48 31 ] ] -RRB- cord-276598-tm0yj2sn 48 32 . . . cord-276598-tm0yj2sn 49 1 Thus thus RB cord-276598-tm0yj2sn 49 2 , , , cord-276598-tm0yj2sn 49 3 on on IN cord-276598-tm0yj2sn 49 4 inhibiting inhibit VBG cord-276598-tm0yj2sn 49 5 the the DT cord-276598-tm0yj2sn 49 6 activity activity NN cord-276598-tm0yj2sn 49 7 of of IN cord-276598-tm0yj2sn 49 8 this this DT cord-276598-tm0yj2sn 49 9 metalloenzyme metalloenzyme NNS cord-276598-tm0yj2sn 49 10 , , , cord-276598-tm0yj2sn 49 11 the the DT cord-276598-tm0yj2sn 49 12 availability availability NN cord-276598-tm0yj2sn 49 13 and and CC cord-276598-tm0yj2sn 49 14 performance performance NN cord-276598-tm0yj2sn 49 15 of of IN cord-276598-tm0yj2sn 49 16 urea urea NN cord-276598-tm0yj2sn 49 17 is be VBZ cord-276598-tm0yj2sn 49 18 enhanced enhance VBN cord-276598-tm0yj2sn 49 19 , , , cord-276598-tm0yj2sn 49 20 which which WDT cord-276598-tm0yj2sn 49 21 is be VBZ cord-276598-tm0yj2sn 49 22 a a DT cord-276598-tm0yj2sn 49 23 vital vital JJ cord-276598-tm0yj2sn 49 24 nitrogenous nitrogenous JJ cord-276598-tm0yj2sn 49 25 fertilizer fertilizer NN cord-276598-tm0yj2sn 49 26 for for IN cord-276598-tm0yj2sn 49 27 plant plant NN cord-276598-tm0yj2sn 49 28 growth growth NN cord-276598-tm0yj2sn 49 29 . . . cord-276598-tm0yj2sn 49 30 _SP cord-276598-tm0yj2sn 50 1 This this DT cord-276598-tm0yj2sn 50 2 class class NN cord-276598-tm0yj2sn 50 3 of of IN cord-276598-tm0yj2sn 50 4 organophosphates organophosphate NNS cord-276598-tm0yj2sn 50 5 ( ( -LRB- cord-276598-tm0yj2sn 50 6 with with IN cord-276598-tm0yj2sn 50 7 common common JJ cord-276598-tm0yj2sn 50 8 names name NNS cord-276598-tm0yj2sn 50 9 such such JJ cord-276598-tm0yj2sn 50 10 as as IN cord-276598-tm0yj2sn 50 11 cruformate cruformate NNP cord-276598-tm0yj2sn 50 12 , , , cord-276598-tm0yj2sn 50 13 fenamiphos fenamiphos NNP cord-276598-tm0yj2sn 50 14 , , , cord-276598-tm0yj2sn 50 15 and and CC cord-276598-tm0yj2sn 50 16 fosthietan fosthietan NNP cord-276598-tm0yj2sn 50 17 ) ) -RRB- cord-276598-tm0yj2sn 50 18 has have VBZ cord-276598-tm0yj2sn 50 19 been be VBN cord-276598-tm0yj2sn 50 20 widely widely RB cord-276598-tm0yj2sn 50 21 used use VBN cord-276598-tm0yj2sn 50 22 in in IN cord-276598-tm0yj2sn 50 23 pest pest NN cord-276598-tm0yj2sn 50 24 management management NN cord-276598-tm0yj2sn 50 25 for for IN cord-276598-tm0yj2sn 50 26 crop crop NN cord-276598-tm0yj2sn 50 27 protection protection NN cord-276598-tm0yj2sn 50 28 ( ( -LRB- cord-276598-tm0yj2sn 50 29 Figure figure NN cord-276598-tm0yj2sn 50 30 3 3 CD cord-276598-tm0yj2sn 50 31 ) ) -RRB- cord-276598-tm0yj2sn 51 1 [ [ -LRB- cord-276598-tm0yj2sn 51 2 19 19 CD cord-276598-tm0yj2sn 51 3 ] ] -RRB- cord-276598-tm0yj2sn 51 4 [ [ -LRB- cord-276598-tm0yj2sn 51 5 20 20 CD cord-276598-tm0yj2sn 51 6 ] ] -RRB- cord-276598-tm0yj2sn 51 7 [ [ -LRB- cord-276598-tm0yj2sn 51 8 21 21 CD cord-276598-tm0yj2sn 51 9 ] ] -RRB- cord-276598-tm0yj2sn 51 10 . . . cord-276598-tm0yj2sn 52 1 P p NN cord-276598-tm0yj2sn 52 2 - - HYPH cord-276598-tm0yj2sn 52 3 Ns Ns NNP cord-276598-tm0yj2sn 52 4 for for IN cord-276598-tm0yj2sn 52 5 pest pest NN cord-276598-tm0yj2sn 52 6 control control NN cord-276598-tm0yj2sn 52 7 affect affect VB cord-276598-tm0yj2sn 52 8 the the DT cord-276598-tm0yj2sn 52 9 nervous nervous JJ cord-276598-tm0yj2sn 52 10 system system NN cord-276598-tm0yj2sn 52 11 of of IN cord-276598-tm0yj2sn 52 12 pests pest NNS cord-276598-tm0yj2sn 52 13 / / SYM cord-276598-tm0yj2sn 52 14 insects insect NNS cord-276598-tm0yj2sn 52 15 by by IN cord-276598-tm0yj2sn 52 16 inhibiting inhibit VBG cord-276598-tm0yj2sn 52 17 acetylcholinesterase acetylcholinesterase NN cord-276598-tm0yj2sn 52 18 ( ( -LRB- cord-276598-tm0yj2sn 52 19 AChE ache NN cord-276598-tm0yj2sn 52 20 ) ) -RRB- cord-276598-tm0yj2sn 52 21 , , , cord-276598-tm0yj2sn 52 22 a a DT cord-276598-tm0yj2sn 52 23 major major JJ cord-276598-tm0yj2sn 52 24 neurotransmitter neurotransmitter NN cord-276598-tm0yj2sn 52 25 [ [ -LRB- cord-276598-tm0yj2sn 52 26 22 22 CD cord-276598-tm0yj2sn 52 27 ] ] -RRB- cord-276598-tm0yj2sn 52 28 [ [ -LRB- cord-276598-tm0yj2sn 52 29 23 23 CD cord-276598-tm0yj2sn 52 30 ] ] -RRB- cord-276598-tm0yj2sn 52 31 [ [ -LRB- cord-276598-tm0yj2sn 52 32 24 24 CD cord-276598-tm0yj2sn 52 33 ] ] -RRB- cord-276598-tm0yj2sn 52 34 [ [ -LRB- cord-276598-tm0yj2sn 52 35 25 25 CD cord-276598-tm0yj2sn 52 36 ] ] -RRB- cord-276598-tm0yj2sn 52 37 . . . cord-276598-tm0yj2sn 53 1 In in IN cord-276598-tm0yj2sn 53 2 addition addition NN cord-276598-tm0yj2sn 53 3 , , , cord-276598-tm0yj2sn 53 4 these these DT cord-276598-tm0yj2sn 53 5 P P NNP cord-276598-tm0yj2sn 53 6 - - HYPH cord-276598-tm0yj2sn 53 7 N N NNP cord-276598-tm0yj2sn 53 8 compounds compound NNS cord-276598-tm0yj2sn 53 9 have have VBP cord-276598-tm0yj2sn 53 10 been be VBN cord-276598-tm0yj2sn 53 11 utilized utilize VBN cord-276598-tm0yj2sn 53 12 as as IN cord-276598-tm0yj2sn 53 13 urease urease NN cord-276598-tm0yj2sn 53 14 inhibitors inhibitor NNS cord-276598-tm0yj2sn 53 15 [ [ -LRB- cord-276598-tm0yj2sn 53 16 26 26 CD cord-276598-tm0yj2sn 53 17 , , , cord-276598-tm0yj2sn 53 18 27 27 CD cord-276598-tm0yj2sn 53 19 ] ] -RRB- cord-276598-tm0yj2sn 53 20 . . . cord-276598-tm0yj2sn 54 1 Urease Urease NNP cord-276598-tm0yj2sn 54 2 is be VBZ cord-276598-tm0yj2sn 54 3 a a DT cord-276598-tm0yj2sn 54 4 nickel nickel NN cord-276598-tm0yj2sn 54 5 - - HYPH cord-276598-tm0yj2sn 54 6 based base VBN cord-276598-tm0yj2sn 54 7 enzyme enzyme NN cord-276598-tm0yj2sn 54 8 that that WDT cord-276598-tm0yj2sn 54 9 catalyzes catalyze VBZ cord-276598-tm0yj2sn 54 10 the the DT cord-276598-tm0yj2sn 54 11 hydrolysis hydrolysis NN cord-276598-tm0yj2sn 54 12 of of IN cord-276598-tm0yj2sn 54 13 urea urea NN cord-276598-tm0yj2sn 54 14 on on IN cord-276598-tm0yj2sn 54 15 soil soil NN cord-276598-tm0yj2sn 54 16 surfaces surface NNS cord-276598-tm0yj2sn 54 17 into into IN cord-276598-tm0yj2sn 54 18 volatile volatile JJ cord-276598-tm0yj2sn 54 19 ammonia ammonia NN cord-276598-tm0yj2sn 54 20 and and CC cord-276598-tm0yj2sn 54 21 carbon carbon NN cord-276598-tm0yj2sn 54 22 dioxide dioxide NN cord-276598-tm0yj2sn 54 23 ( ( -LRB- cord-276598-tm0yj2sn 54 24 Scheme scheme NN cord-276598-tm0yj2sn 54 25 1 1 CD cord-276598-tm0yj2sn 54 26 ) ) -RRB- cord-276598-tm0yj2sn 54 27 [ [ -LRB- cord-276598-tm0yj2sn 54 28 28 28 CD cord-276598-tm0yj2sn 54 29 , , , cord-276598-tm0yj2sn 54 30 29 29 CD cord-276598-tm0yj2sn 54 31 ] ] -RRB- cord-276598-tm0yj2sn 54 32 . . . cord-276598-tm0yj2sn 55 1 Thus thus RB cord-276598-tm0yj2sn 55 2 , , , cord-276598-tm0yj2sn 55 3 on on IN cord-276598-tm0yj2sn 55 4 inhibiting inhibit VBG cord-276598-tm0yj2sn 55 5 the the DT cord-276598-tm0yj2sn 55 6 activity activity NN cord-276598-tm0yj2sn 55 7 of of IN cord-276598-tm0yj2sn 55 8 this this DT cord-276598-tm0yj2sn 55 9 metalloenzyme metalloenzyme NNS cord-276598-tm0yj2sn 55 10 , , , cord-276598-tm0yj2sn 55 11 the the DT cord-276598-tm0yj2sn 55 12 availability availability NN cord-276598-tm0yj2sn 55 13 and and CC cord-276598-tm0yj2sn 55 14 performance performance NN cord-276598-tm0yj2sn 55 15 of of IN cord-276598-tm0yj2sn 55 16 urea urea NN cord-276598-tm0yj2sn 55 17 is be VBZ cord-276598-tm0yj2sn 55 18 enhanced enhance VBN cord-276598-tm0yj2sn 55 19 , , , cord-276598-tm0yj2sn 55 20 which which WDT cord-276598-tm0yj2sn 55 21 is be VBZ cord-276598-tm0yj2sn 55 22 a a DT cord-276598-tm0yj2sn 55 23 vital vital JJ cord-276598-tm0yj2sn 55 24 nitrogenous nitrogenous JJ cord-276598-tm0yj2sn 55 25 fertilizer fertilizer NN cord-276598-tm0yj2sn 55 26 for for IN cord-276598-tm0yj2sn 55 27 plant plant NN cord-276598-tm0yj2sn 55 28 growth growth NN cord-276598-tm0yj2sn 55 29 . . . cord-276598-tm0yj2sn 55 30 _SP cord-276598-tm0yj2sn 56 1 P p NN cord-276598-tm0yj2sn 56 2 - - HYPH cord-276598-tm0yj2sn 56 3 Ns Ns NNP cord-276598-tm0yj2sn 56 4 have have VBP cord-276598-tm0yj2sn 56 5 been be VBN cord-276598-tm0yj2sn 56 6 used use VBN cord-276598-tm0yj2sn 56 7 as as IN cord-276598-tm0yj2sn 56 8 additives additive NNS cord-276598-tm0yj2sn 56 9 in in IN cord-276598-tm0yj2sn 56 10 both both DT cord-276598-tm0yj2sn 56 11 oil oil NN cord-276598-tm0yj2sn 56 12 and and CC cord-276598-tm0yj2sn 56 13 water water NN cord-276598-tm0yj2sn 56 14 - - HYPH cord-276598-tm0yj2sn 56 15 based base VBN cord-276598-tm0yj2sn 56 16 lubricants lubricant NNS cord-276598-tm0yj2sn 56 17 ( ( -LRB- cord-276598-tm0yj2sn 56 18 Figure figure NN cord-276598-tm0yj2sn 56 19 3 3 CD cord-276598-tm0yj2sn 56 20 ) ) -RRB- cord-276598-tm0yj2sn 56 21 . . . cord-276598-tm0yj2sn 57 1 It -PRON- PRP cord-276598-tm0yj2sn 57 2 has have VBZ cord-276598-tm0yj2sn 57 3 been be VBN cord-276598-tm0yj2sn 57 4 proposed propose VBN cord-276598-tm0yj2sn 57 5 that that IN cord-276598-tm0yj2sn 57 6 phosphorus phosphorus NN cord-276598-tm0yj2sn 57 7 acts act VBZ cord-276598-tm0yj2sn 57 8 as as IN cord-276598-tm0yj2sn 57 9 a a DT cord-276598-tm0yj2sn 57 10 key key JJ cord-276598-tm0yj2sn 57 11 element element NN cord-276598-tm0yj2sn 57 12 in in IN cord-276598-tm0yj2sn 57 13 enhancing enhance VBG cord-276598-tm0yj2sn 57 14 the the DT cord-276598-tm0yj2sn 57 15 tribological tribological NNP cord-276598-tm0yj2sn 57 16 properties property NNS cord-276598-tm0yj2sn 57 17 of of IN cord-276598-tm0yj2sn 57 18 water water NN cord-276598-tm0yj2sn 57 19 / / SYM cord-276598-tm0yj2sn 57 20 oil oil NN cord-276598-tm0yj2sn 57 21 - - HYPH cord-276598-tm0yj2sn 57 22 based base VBN cord-276598-tm0yj2sn 57 23 fluids fluid NNS cord-276598-tm0yj2sn 57 24 by by IN cord-276598-tm0yj2sn 57 25 forming form VBG cord-276598-tm0yj2sn 57 26 a a DT cord-276598-tm0yj2sn 57 27 protective protective JJ cord-276598-tm0yj2sn 57 28 layer layer NN cord-276598-tm0yj2sn 57 29 containing contain VBG cord-276598-tm0yj2sn 57 30 phosphates phosphate NNS cord-276598-tm0yj2sn 57 31 and/or and/or CC cord-276598-tm0yj2sn 57 32 polyphosphates polyphosphate NNS cord-276598-tm0yj2sn 57 33 . . . cord-276598-tm0yj2sn 58 1 Thus thus RB cord-276598-tm0yj2sn 58 2 , , , cord-276598-tm0yj2sn 58 3 they -PRON- PRP cord-276598-tm0yj2sn 58 4 possess possess VBP cord-276598-tm0yj2sn 58 5 anti anti JJ cord-276598-tm0yj2sn 58 6 - - JJ cord-276598-tm0yj2sn 58 7 wear wear JJ cord-276598-tm0yj2sn 58 8 and and CC cord-276598-tm0yj2sn 58 9 friction friction NN cord-276598-tm0yj2sn 58 10 - - HYPH cord-276598-tm0yj2sn 58 11 reducing reduce VBG cord-276598-tm0yj2sn 58 12 properties property NNS cord-276598-tm0yj2sn 58 13 [ [ -LRB- cord-276598-tm0yj2sn 58 14 18 18 CD cord-276598-tm0yj2sn 58 15 , , , cord-276598-tm0yj2sn 58 16 30 30 CD cord-276598-tm0yj2sn 58 17 ] ] -RRB- cord-276598-tm0yj2sn 58 18 . . . cord-276598-tm0yj2sn 59 1 Furthermore furthermore RB cord-276598-tm0yj2sn 59 2 , , , cord-276598-tm0yj2sn 59 3 these these DT cord-276598-tm0yj2sn 59 4 P P NNP cord-276598-tm0yj2sn 59 5 - - HYPH cord-276598-tm0yj2sn 59 6 Ns Ns NNP cord-276598-tm0yj2sn 59 7 have have VBP cord-276598-tm0yj2sn 59 8 been be VBN cord-276598-tm0yj2sn 59 9 found find VBN cord-276598-tm0yj2sn 59 10 to to TO cord-276598-tm0yj2sn 59 11 be be VB cord-276598-tm0yj2sn 59 12 a a DT cord-276598-tm0yj2sn 59 13 promising promising JJ cord-276598-tm0yj2sn 59 14 alternative alternative NN cord-276598-tm0yj2sn 59 15 to to IN cord-276598-tm0yj2sn 59 16 halogenated halogenated JJ cord-276598-tm0yj2sn 59 17 flame flame NN cord-276598-tm0yj2sn 59 18 retardants retardant NNS cord-276598-tm0yj2sn 59 19 ( ( -LRB- cord-276598-tm0yj2sn 59 20 FRs FRs NNP cord-276598-tm0yj2sn 59 21 ) ) -RRB- cord-276598-tm0yj2sn 59 22 , , , cord-276598-tm0yj2sn 59 23 which which WDT cord-276598-tm0yj2sn 59 24 are be VBP cord-276598-tm0yj2sn 59 25 being be VBG cord-276598-tm0yj2sn 59 26 phased phase VBN cord-276598-tm0yj2sn 59 27 out out RP cord-276598-tm0yj2sn 59 28 as as IN cord-276598-tm0yj2sn 59 29 they -PRON- PRP cord-276598-tm0yj2sn 59 30 have have VBP cord-276598-tm0yj2sn 59 31 been be VBN cord-276598-tm0yj2sn 59 32 recognized recognize VBN cord-276598-tm0yj2sn 59 33 as as IN cord-276598-tm0yj2sn 59 34 global global JJ cord-276598-tm0yj2sn 59 35 contaminants contaminant NNS cord-276598-tm0yj2sn 59 36 due due IN cord-276598-tm0yj2sn 59 37 to to IN cord-276598-tm0yj2sn 59 38 their -PRON- PRP$ cord-276598-tm0yj2sn 59 39 ill ill JJ cord-276598-tm0yj2sn 59 40 effects effect NNS cord-276598-tm0yj2sn 59 41 on on IN cord-276598-tm0yj2sn 59 42 health health NN cord-276598-tm0yj2sn 59 43 and and CC cord-276598-tm0yj2sn 59 44 the the DT cord-276598-tm0yj2sn 59 45 environment environment NN cord-276598-tm0yj2sn 59 46 [ [ -LRB- cord-276598-tm0yj2sn 59 47 31 31 CD cord-276598-tm0yj2sn 59 48 ] ] -RRB- cord-276598-tm0yj2sn 59 49 . . . cord-276598-tm0yj2sn 60 1 P p NN cord-276598-tm0yj2sn 60 2 - - HYPH cord-276598-tm0yj2sn 60 3 N n CD cord-276598-tm0yj2sn 60 4 fire fire NN cord-276598-tm0yj2sn 60 5 retardants retardant NNS cord-276598-tm0yj2sn 60 6 are be VBP cord-276598-tm0yj2sn 60 7 less less RBR cord-276598-tm0yj2sn 60 8 volatile volatile JJ cord-276598-tm0yj2sn 60 9 and and CC cord-276598-tm0yj2sn 60 10 relatively relatively RB cord-276598-tm0yj2sn 60 11 thermally thermally RB cord-276598-tm0yj2sn 60 12 stable stable JJ cord-276598-tm0yj2sn 60 13 with with IN cord-276598-tm0yj2sn 60 14 Scheme scheme NN cord-276598-tm0yj2sn 60 15 1 1 CD cord-276598-tm0yj2sn 60 16 . . . cord-276598-tm0yj2sn 61 1 Hydrolysis hydrolysis NN cord-276598-tm0yj2sn 61 2 of of IN cord-276598-tm0yj2sn 61 3 urea urea NN cord-276598-tm0yj2sn 61 4 on on IN cord-276598-tm0yj2sn 61 5 soil soil NN cord-276598-tm0yj2sn 61 6 in in IN cord-276598-tm0yj2sn 61 7 the the DT cord-276598-tm0yj2sn 61 8 presence presence NN cord-276598-tm0yj2sn 61 9 of of IN cord-276598-tm0yj2sn 61 10 urease urease NN cord-276598-tm0yj2sn 61 11 . . . cord-276598-tm0yj2sn 62 1 P p NN cord-276598-tm0yj2sn 62 2 - - HYPH cord-276598-tm0yj2sn 62 3 Ns Ns NNP cord-276598-tm0yj2sn 62 4 have have VBP cord-276598-tm0yj2sn 62 5 been be VBN cord-276598-tm0yj2sn 62 6 used use VBN cord-276598-tm0yj2sn 62 7 as as IN cord-276598-tm0yj2sn 62 8 additives additive NNS cord-276598-tm0yj2sn 62 9 in in IN cord-276598-tm0yj2sn 62 10 both both DT cord-276598-tm0yj2sn 62 11 oil oil NN cord-276598-tm0yj2sn 62 12 and and CC cord-276598-tm0yj2sn 62 13 water water NN cord-276598-tm0yj2sn 62 14 - - HYPH cord-276598-tm0yj2sn 62 15 based base VBN cord-276598-tm0yj2sn 62 16 lubricants lubricant NNS cord-276598-tm0yj2sn 62 17 ( ( -LRB- cord-276598-tm0yj2sn 62 18 Figure figure NN cord-276598-tm0yj2sn 62 19 3 3 CD cord-276598-tm0yj2sn 62 20 ) ) -RRB- cord-276598-tm0yj2sn 62 21 . . . cord-276598-tm0yj2sn 63 1 It -PRON- PRP cord-276598-tm0yj2sn 63 2 has have VBZ cord-276598-tm0yj2sn 63 3 been be VBN cord-276598-tm0yj2sn 63 4 proposed propose VBN cord-276598-tm0yj2sn 63 5 that that IN cord-276598-tm0yj2sn 63 6 phosphorus phosphorus NN cord-276598-tm0yj2sn 63 7 acts act VBZ cord-276598-tm0yj2sn 63 8 as as IN cord-276598-tm0yj2sn 63 9 a a DT cord-276598-tm0yj2sn 63 10 key key JJ cord-276598-tm0yj2sn 63 11 element element NN cord-276598-tm0yj2sn 63 12 in in IN cord-276598-tm0yj2sn 63 13 enhancing enhance VBG cord-276598-tm0yj2sn 63 14 the the DT cord-276598-tm0yj2sn 63 15 tribological tribological NNP cord-276598-tm0yj2sn 63 16 properties property NNS cord-276598-tm0yj2sn 63 17 of of IN cord-276598-tm0yj2sn 63 18 water water NN cord-276598-tm0yj2sn 63 19 / / SYM cord-276598-tm0yj2sn 63 20 oil oil NN cord-276598-tm0yj2sn 63 21 - - HYPH cord-276598-tm0yj2sn 63 22 based base VBN cord-276598-tm0yj2sn 63 23 fluids fluid NNS cord-276598-tm0yj2sn 63 24 by by IN cord-276598-tm0yj2sn 63 25 forming form VBG cord-276598-tm0yj2sn 63 26 a a DT cord-276598-tm0yj2sn 63 27 protective protective JJ cord-276598-tm0yj2sn 63 28 layer layer NN cord-276598-tm0yj2sn 63 29 containing contain VBG cord-276598-tm0yj2sn 63 30 phosphates phosphate NNS cord-276598-tm0yj2sn 63 31 and/or and/or CC cord-276598-tm0yj2sn 63 32 polyphosphates polyphosphate NNS cord-276598-tm0yj2sn 63 33 . . . cord-276598-tm0yj2sn 64 1 Thus thus RB cord-276598-tm0yj2sn 64 2 , , , cord-276598-tm0yj2sn 64 3 they -PRON- PRP cord-276598-tm0yj2sn 64 4 possess possess VBP cord-276598-tm0yj2sn 64 5 anti anti JJ cord-276598-tm0yj2sn 64 6 - - JJ cord-276598-tm0yj2sn 64 7 wear wear JJ cord-276598-tm0yj2sn 64 8 and and CC cord-276598-tm0yj2sn 64 9 friction friction NN cord-276598-tm0yj2sn 64 10 - - HYPH cord-276598-tm0yj2sn 64 11 reducing reduce VBG cord-276598-tm0yj2sn 64 12 properties property NNS cord-276598-tm0yj2sn 64 13 [ [ -LRB- cord-276598-tm0yj2sn 64 14 18 18 CD cord-276598-tm0yj2sn 64 15 , , , cord-276598-tm0yj2sn 64 16 30 30 CD cord-276598-tm0yj2sn 64 17 ] ] -RRB- cord-276598-tm0yj2sn 64 18 . . . cord-276598-tm0yj2sn 65 1 Furthermore furthermore RB cord-276598-tm0yj2sn 65 2 , , , cord-276598-tm0yj2sn 65 3 these these DT cord-276598-tm0yj2sn 65 4 P P NNP cord-276598-tm0yj2sn 65 5 - - HYPH cord-276598-tm0yj2sn 65 6 Ns Ns NNP cord-276598-tm0yj2sn 65 7 have have VBP cord-276598-tm0yj2sn 65 8 been be VBN cord-276598-tm0yj2sn 65 9 found find VBN cord-276598-tm0yj2sn 65 10 to to TO cord-276598-tm0yj2sn 65 11 be be VB cord-276598-tm0yj2sn 65 12 a a DT cord-276598-tm0yj2sn 65 13 promising promising JJ cord-276598-tm0yj2sn 65 14 alternative alternative NN cord-276598-tm0yj2sn 65 15 to to IN cord-276598-tm0yj2sn 65 16 halogenated halogenated JJ cord-276598-tm0yj2sn 65 17 flame flame NN cord-276598-tm0yj2sn 65 18 retardants retardant NNS cord-276598-tm0yj2sn 65 19 ( ( -LRB- cord-276598-tm0yj2sn 65 20 FRs FRs NNP cord-276598-tm0yj2sn 65 21 ) ) -RRB- cord-276598-tm0yj2sn 65 22 , , , cord-276598-tm0yj2sn 65 23 which which WDT cord-276598-tm0yj2sn 65 24 are be VBP cord-276598-tm0yj2sn 65 25 being be VBG cord-276598-tm0yj2sn 65 26 phased phase VBN cord-276598-tm0yj2sn 65 27 out out RP cord-276598-tm0yj2sn 65 28 as as IN cord-276598-tm0yj2sn 65 29 they -PRON- PRP cord-276598-tm0yj2sn 65 30 have have VBP cord-276598-tm0yj2sn 65 31 been be VBN cord-276598-tm0yj2sn 65 32 recognized recognize VBN cord-276598-tm0yj2sn 65 33 as as IN cord-276598-tm0yj2sn 65 34 global global JJ cord-276598-tm0yj2sn 65 35 contaminants contaminant NNS cord-276598-tm0yj2sn 65 36 due due IN cord-276598-tm0yj2sn 65 37 to to IN cord-276598-tm0yj2sn 65 38 their -PRON- PRP$ cord-276598-tm0yj2sn 65 39 ill ill JJ cord-276598-tm0yj2sn 65 40 effects effect NNS cord-276598-tm0yj2sn 65 41 on on IN cord-276598-tm0yj2sn 65 42 health health NN cord-276598-tm0yj2sn 65 43 and and CC cord-276598-tm0yj2sn 65 44 the the DT cord-276598-tm0yj2sn 65 45 environment environment NN cord-276598-tm0yj2sn 65 46 [ [ -LRB- cord-276598-tm0yj2sn 65 47 31 31 CD cord-276598-tm0yj2sn 65 48 ] ] -RRB- cord-276598-tm0yj2sn 65 49 . . . cord-276598-tm0yj2sn 66 1 P p NN cord-276598-tm0yj2sn 66 2 - - HYPH cord-276598-tm0yj2sn 66 3 N n CD cord-276598-tm0yj2sn 66 4 fire fire NN cord-276598-tm0yj2sn 66 5 retardants retardant NNS cord-276598-tm0yj2sn 66 6 are be VBP cord-276598-tm0yj2sn 66 7 less less RBR cord-276598-tm0yj2sn 66 8 volatile volatile JJ cord-276598-tm0yj2sn 66 9 and and CC cord-276598-tm0yj2sn 66 10 relatively relatively RB cord-276598-tm0yj2sn 66 11 thermally thermally RB cord-276598-tm0yj2sn 66 12 stable stable JJ cord-276598-tm0yj2sn 66 13 with with IN cord-276598-tm0yj2sn 66 14 enhanced enhanced JJ cord-276598-tm0yj2sn 66 15 char char NN cord-276598-tm0yj2sn 66 16 formation formation NN cord-276598-tm0yj2sn 66 17 , , , cord-276598-tm0yj2sn 66 18 and and CC cord-276598-tm0yj2sn 66 19 they -PRON- PRP cord-276598-tm0yj2sn 66 20 are be VBP cord-276598-tm0yj2sn 66 21 more more RBR cord-276598-tm0yj2sn 66 22 efficient efficient JJ cord-276598-tm0yj2sn 66 23 and and CC cord-276598-tm0yj2sn 66 24 sustainable sustainable JJ cord-276598-tm0yj2sn 66 25 than than IN cord-276598-tm0yj2sn 66 26 their -PRON- PRP$ cord-276598-tm0yj2sn 66 27 halogenated halogenate VBN cord-276598-tm0yj2sn 66 28 Molecules molecule NNS cord-276598-tm0yj2sn 66 29 2020 2020 CD cord-276598-tm0yj2sn 66 30 , , , cord-276598-tm0yj2sn 66 31 25 25 CD cord-276598-tm0yj2sn 66 32 , , , cord-276598-tm0yj2sn 66 33 3684 3684 CD cord-276598-tm0yj2sn 66 34 4 4 CD cord-276598-tm0yj2sn 66 35 of of IN cord-276598-tm0yj2sn 66 36 37 37 CD cord-276598-tm0yj2sn 66 37 counterparts counterpart NNS cord-276598-tm0yj2sn 66 38 [ [ -LRB- cord-276598-tm0yj2sn 66 39 32 32 CD cord-276598-tm0yj2sn 66 40 , , , cord-276598-tm0yj2sn 66 41 33 33 CD cord-276598-tm0yj2sn 66 42 ] ] -RRB- cord-276598-tm0yj2sn 66 43 . . . cord-276598-tm0yj2sn 67 1 Recently recently RB cord-276598-tm0yj2sn 67 2 , , , cord-276598-tm0yj2sn 67 3 compounds compound NNS cord-276598-tm0yj2sn 67 4 containing contain VBG cord-276598-tm0yj2sn 67 5 both both CC cord-276598-tm0yj2sn 67 6 P P NNP cord-276598-tm0yj2sn 67 7 and and CC cord-276598-tm0yj2sn 67 8 N n CD cord-276598-tm0yj2sn 67 9 atoms atom NNS cord-276598-tm0yj2sn 67 10 in in IN cord-276598-tm0yj2sn 67 11 combination combination NN cord-276598-tm0yj2sn 67 12 have have VBP cord-276598-tm0yj2sn 67 13 been be VBN cord-276598-tm0yj2sn 67 14 reported report VBN cord-276598-tm0yj2sn 67 15 to to TO cord-276598-tm0yj2sn 67 16 have have VB cord-276598-tm0yj2sn 67 17 a a DT cord-276598-tm0yj2sn 67 18 synergistic synergistic JJ cord-276598-tm0yj2sn 67 19 effect effect NN cord-276598-tm0yj2sn 67 20 , , , cord-276598-tm0yj2sn 67 21 as as IN cord-276598-tm0yj2sn 67 22 they -PRON- PRP cord-276598-tm0yj2sn 67 23 can can MD cord-276598-tm0yj2sn 67 24 act act VB cord-276598-tm0yj2sn 67 25 in in IN cord-276598-tm0yj2sn 67 26 both both DT cord-276598-tm0yj2sn 67 27 vapor vapor NN cord-276598-tm0yj2sn 67 28 phase phase NN cord-276598-tm0yj2sn 67 29 and and CC cord-276598-tm0yj2sn 67 30 condensed condensed JJ cord-276598-tm0yj2sn 67 31 phase phase NN cord-276598-tm0yj2sn 67 32 , , , cord-276598-tm0yj2sn 67 33 thus thus RB cord-276598-tm0yj2sn 67 34 offering offer VBG cord-276598-tm0yj2sn 67 35 improved improve VBN cord-276598-tm0yj2sn 67 36 flame flame NN cord-276598-tm0yj2sn 67 37 retardancy retardancy NN cord-276598-tm0yj2sn 67 38 on on IN cord-276598-tm0yj2sn 67 39 various various JJ cord-276598-tm0yj2sn 67 40 substrates substrate NNS cord-276598-tm0yj2sn 67 41 such such JJ cord-276598-tm0yj2sn 67 42 as as IN cord-276598-tm0yj2sn 67 43 polyurethane polyurethane NN cord-276598-tm0yj2sn 67 44 foams foam NNS cord-276598-tm0yj2sn 67 45 , , , cord-276598-tm0yj2sn 67 46 cotton cotton NN cord-276598-tm0yj2sn 67 47 , , , cord-276598-tm0yj2sn 67 48 cellulose cellulose NN cord-276598-tm0yj2sn 67 49 , , , cord-276598-tm0yj2sn 67 50 epoxy epoxy NN cord-276598-tm0yj2sn 67 51 resins resin NNS cord-276598-tm0yj2sn 67 52 , , , cord-276598-tm0yj2sn 67 53 textiles textile NNS cord-276598-tm0yj2sn 67 54 , , , cord-276598-tm0yj2sn 67 55 etc etc FW cord-276598-tm0yj2sn 67 56 . . . cord-276598-tm0yj2sn 68 1 [ [ -LRB- cord-276598-tm0yj2sn 68 2 34 34 CD cord-276598-tm0yj2sn 68 3 ] ] -RRB- cord-276598-tm0yj2sn 68 4 [ [ -LRB- cord-276598-tm0yj2sn 68 5 35 35 CD cord-276598-tm0yj2sn 68 6 ] ] -RRB- cord-276598-tm0yj2sn 68 7 [ [ -LRB- cord-276598-tm0yj2sn 68 8 36 36 CD cord-276598-tm0yj2sn 68 9 ] ] -RRB- cord-276598-tm0yj2sn 69 1 [ [ -LRB- cord-276598-tm0yj2sn 69 2 37 37 CD cord-276598-tm0yj2sn 69 3 ] ] -RRB- cord-276598-tm0yj2sn 69 4 [ [ -LRB- cord-276598-tm0yj2sn 69 5 38 38 CD cord-276598-tm0yj2sn 69 6 ] ] -RRB- cord-276598-tm0yj2sn 70 1 [ [ -LRB- cord-276598-tm0yj2sn 70 2 39 39 CD cord-276598-tm0yj2sn 70 3 ] ] -RRB- cord-276598-tm0yj2sn 70 4 [ [ -LRB- cord-276598-tm0yj2sn 70 5 40 40 CD cord-276598-tm0yj2sn 70 6 ] ] -RRB- cord-276598-tm0yj2sn 70 7 . . . cord-276598-tm0yj2sn 71 1 For for IN cord-276598-tm0yj2sn 71 2 example example NN cord-276598-tm0yj2sn 71 3 , , , cord-276598-tm0yj2sn 71 4 novel novel NN cord-276598-tm0yj2sn 71 5 P p NN cord-276598-tm0yj2sn 71 6 - - HYPH cord-276598-tm0yj2sn 71 7 N n NN cord-276598-tm0yj2sn 71 8 - - HYPH cord-276598-tm0yj2sn 71 9 based base VBN cord-276598-tm0yj2sn 71 10 intumescent intumescent NN cord-276598-tm0yj2sn 71 11 flame flame NN cord-276598-tm0yj2sn 71 12 retardants retardant NNS cord-276598-tm0yj2sn 71 13 have have VBP cord-276598-tm0yj2sn 71 14 been be VBN cord-276598-tm0yj2sn 71 15 incorporated incorporate VBN cord-276598-tm0yj2sn 71 16 into into IN cord-276598-tm0yj2sn 71 17 polycarbonates polycarbonate NNS cord-276598-tm0yj2sn 71 18 ( ( -LRB- cord-276598-tm0yj2sn 71 19 PC pc NN cord-276598-tm0yj2sn 71 20 ) ) -RRB- cord-276598-tm0yj2sn 71 21 to to TO cord-276598-tm0yj2sn 71 22 impart impart VB cord-276598-tm0yj2sn 71 23 flame flame NN cord-276598-tm0yj2sn 71 24 retardancy retardancy NN cord-276598-tm0yj2sn 71 25 to to IN cord-276598-tm0yj2sn 71 26 the the DT cord-276598-tm0yj2sn 71 27 composite composite NN cord-276598-tm0yj2sn 71 28 by by IN cord-276598-tm0yj2sn 71 29 forming form VBG cord-276598-tm0yj2sn 71 30 an an DT cord-276598-tm0yj2sn 71 31 expandable expandable JJ cord-276598-tm0yj2sn 71 32 protective protective JJ cord-276598-tm0yj2sn 71 33 char char NN cord-276598-tm0yj2sn 71 34 [ [ -LRB- cord-276598-tm0yj2sn 71 35 41 41 CD cord-276598-tm0yj2sn 71 36 ] ] -RRB- cord-276598-tm0yj2sn 71 37 . . . cord-276598-tm0yj2sn 72 1 MALDI MALDI NNP cord-276598-tm0yj2sn 72 2 - - HYPH cord-276598-tm0yj2sn 72 3 TOF TOF NNP cord-276598-tm0yj2sn 72 4 MS MS NNP cord-276598-tm0yj2sn 72 5 is be VBZ cord-276598-tm0yj2sn 72 6 a a DT cord-276598-tm0yj2sn 72 7 prominent prominent JJ cord-276598-tm0yj2sn 72 8 tool tool NN cord-276598-tm0yj2sn 72 9 for for IN cord-276598-tm0yj2sn 72 10 analyzing analyze VBG cord-276598-tm0yj2sn 72 11 biomolecules biomolecule NNS cord-276598-tm0yj2sn 72 12 ( ( -LRB- cord-276598-tm0yj2sn 72 13 Figure figure NN cord-276598-tm0yj2sn 72 14 3 3 CD cord-276598-tm0yj2sn 72 15 ) ) -RRB- cord-276598-tm0yj2sn 73 1 [ [ -LRB- cord-276598-tm0yj2sn 73 2 42 42 CD cord-276598-tm0yj2sn 73 3 ] ] -RRB- cord-276598-tm0yj2sn 73 4 . . . cord-276598-tm0yj2sn 74 1 For for IN cord-276598-tm0yj2sn 74 2 the the DT cord-276598-tm0yj2sn 74 3 detection detection NN cord-276598-tm0yj2sn 74 4 of of IN cord-276598-tm0yj2sn 74 5 low low JJ cord-276598-tm0yj2sn 74 6 molecular molecular JJ cord-276598-tm0yj2sn 74 7 weight weight NN cord-276598-tm0yj2sn 74 8 such such JJ cord-276598-tm0yj2sn 74 9 as as IN cord-276598-tm0yj2sn 74 10 amino amino JJ cord-276598-tm0yj2sn 74 11 acids acid NNS cord-276598-tm0yj2sn 74 12 and and CC cord-276598-tm0yj2sn 74 13 peptides peptide NNS cord-276598-tm0yj2sn 74 14 , , , cord-276598-tm0yj2sn 74 15 conventional conventional JJ cord-276598-tm0yj2sn 74 16 matrices matrix NNS cord-276598-tm0yj2sn 74 17 yield yield VBP cord-276598-tm0yj2sn 74 18 a a DT cord-276598-tm0yj2sn 74 19 lot lot NN cord-276598-tm0yj2sn 74 20 of of IN cord-276598-tm0yj2sn 74 21 matrix matrix NN cord-276598-tm0yj2sn 74 22 - - HYPH cord-276598-tm0yj2sn 74 23 related relate VBN cord-276598-tm0yj2sn 74 24 ions ion NNS cord-276598-tm0yj2sn 74 25 in in IN cord-276598-tm0yj2sn 74 26 the the DT cord-276598-tm0yj2sn 74 27 low low JJ cord-276598-tm0yj2sn 74 28 m m NN cord-276598-tm0yj2sn 74 29 / / SYM cord-276598-tm0yj2sn 74 30 z z CD cord-276598-tm0yj2sn 74 31 range range NN cord-276598-tm0yj2sn 74 32 of of IN cord-276598-tm0yj2sn 74 33 the the DT cord-276598-tm0yj2sn 74 34 spectrum spectrum NN cord-276598-tm0yj2sn 74 35 , , , cord-276598-tm0yj2sn 74 36 thus thus RB cord-276598-tm0yj2sn 74 37 interfering interfere VBG cord-276598-tm0yj2sn 74 38 with with IN cord-276598-tm0yj2sn 74 39 analyte analyte NN cord-276598-tm0yj2sn 74 40 signals signal NNS cord-276598-tm0yj2sn 74 41 . . . cord-276598-tm0yj2sn 75 1 To to TO cord-276598-tm0yj2sn 75 2 tackle tackle VB cord-276598-tm0yj2sn 75 3 this this DT cord-276598-tm0yj2sn 75 4 , , , cord-276598-tm0yj2sn 75 5 various various JJ cord-276598-tm0yj2sn 75 6 approaches approach NNS cord-276598-tm0yj2sn 75 7 such such JJ cord-276598-tm0yj2sn 75 8 as as IN cord-276598-tm0yj2sn 75 9 using use VBG cord-276598-tm0yj2sn 75 10 additives additive NNS cord-276598-tm0yj2sn 75 11 in in IN cord-276598-tm0yj2sn 75 12 the the DT cord-276598-tm0yj2sn 75 13 organic organic JJ cord-276598-tm0yj2sn 75 14 matrix matrix NN cord-276598-tm0yj2sn 75 15 , , , cord-276598-tm0yj2sn 75 16 high high JJ cord-276598-tm0yj2sn 75 17 mass mass NN cord-276598-tm0yj2sn 75 18 matrix matrix NN cord-276598-tm0yj2sn 75 19 molecules molecule NNS cord-276598-tm0yj2sn 75 20 , , , cord-276598-tm0yj2sn 75 21 or or CC cord-276598-tm0yj2sn 75 22 matrices matrix NNS cord-276598-tm0yj2sn 75 23 based base VBN cord-276598-tm0yj2sn 75 24 on on IN cord-276598-tm0yj2sn 75 25 inorganic inorganic JJ cord-276598-tm0yj2sn 75 26 compounds compound NNS cord-276598-tm0yj2sn 75 27 have have VBP cord-276598-tm0yj2sn 75 28 been be VBN cord-276598-tm0yj2sn 75 29 employed employ VBN cord-276598-tm0yj2sn 75 30 [ [ -LRB- cord-276598-tm0yj2sn 75 31 43 43 CD cord-276598-tm0yj2sn 75 32 ] ] -RRB- cord-276598-tm0yj2sn 75 33 . . . cord-276598-tm0yj2sn 76 1 Furthermore furthermore RB cord-276598-tm0yj2sn 76 2 , , , cord-276598-tm0yj2sn 76 3 to to TO cord-276598-tm0yj2sn 76 4 improve improve VB cord-276598-tm0yj2sn 76 5 analysis analysis NN cord-276598-tm0yj2sn 76 6 , , , cord-276598-tm0yj2sn 76 7 synthesizing synthesize VBG cord-276598-tm0yj2sn 76 8 derivatives derivative NNS cord-276598-tm0yj2sn 76 9 of of IN cord-276598-tm0yj2sn 76 10 small small JJ cord-276598-tm0yj2sn 76 11 analyte analyte NN cord-276598-tm0yj2sn 76 12 molecules molecule NNS cord-276598-tm0yj2sn 76 13 by by IN cord-276598-tm0yj2sn 76 14 N n CD cord-276598-tm0yj2sn 76 15 - - HYPH cord-276598-tm0yj2sn 76 16 phosphorylation phosphorylation NN cord-276598-tm0yj2sn 76 17 labeling labeling NN cord-276598-tm0yj2sn 76 18 has have VBZ cord-276598-tm0yj2sn 76 19 been be VBN cord-276598-tm0yj2sn 76 20 done do VBN cord-276598-tm0yj2sn 76 21 . . . cord-276598-tm0yj2sn 77 1 The the DT cord-276598-tm0yj2sn 77 2 neutral neutral JJ cord-276598-tm0yj2sn 77 3 phosphoryl phosphoryl NN cord-276598-tm0yj2sn 77 4 group group NN cord-276598-tm0yj2sn 77 5 attached attach VBN cord-276598-tm0yj2sn 77 6 at at IN cord-276598-tm0yj2sn 77 7 the the DT cord-276598-tm0yj2sn 77 8 N n CD cord-276598-tm0yj2sn 77 9 - - HYPH cord-276598-tm0yj2sn 77 10 terminal terminal NN cord-276598-tm0yj2sn 77 11 of of IN cord-276598-tm0yj2sn 77 12 amino amino JJ cord-276598-tm0yj2sn 77 13 acids acid NNS cord-276598-tm0yj2sn 77 14 suppresses suppress VBZ cord-276598-tm0yj2sn 77 15 the the DT cord-276598-tm0yj2sn 77 16 matrix matrix NN cord-276598-tm0yj2sn 77 17 signals signal NNS cord-276598-tm0yj2sn 77 18 and and CC cord-276598-tm0yj2sn 77 19 favors favor VBZ cord-276598-tm0yj2sn 77 20 the the DT cord-276598-tm0yj2sn 77 21 transfer transfer NN cord-276598-tm0yj2sn 77 22 of of IN cord-276598-tm0yj2sn 77 23 energy energy NN cord-276598-tm0yj2sn 77 24 from from IN cord-276598-tm0yj2sn 77 25 matrix matrix NN cord-276598-tm0yj2sn 77 26 to to IN cord-276598-tm0yj2sn 77 27 analyte analyte NN cord-276598-tm0yj2sn 77 28 for for IN cord-276598-tm0yj2sn 77 29 ionization ionization NN cord-276598-tm0yj2sn 77 30 by by IN cord-276598-tm0yj2sn 77 31 secondary secondary JJ cord-276598-tm0yj2sn 77 32 ion ion NN cord-276598-tm0yj2sn 77 33 - - HYPH cord-276598-tm0yj2sn 77 34 molecule molecule NN cord-276598-tm0yj2sn 77 35 reactions reaction NNS cord-276598-tm0yj2sn 77 36 . . . cord-276598-tm0yj2sn 78 1 Therefore therefore RB cord-276598-tm0yj2sn 78 2 , , , cord-276598-tm0yj2sn 78 3 P P NNP cord-276598-tm0yj2sn 78 4 - - HYPH cord-276598-tm0yj2sn 78 5 Ns Ns NNP cord-276598-tm0yj2sn 78 6 have have VBP cord-276598-tm0yj2sn 78 7 been be VBN cord-276598-tm0yj2sn 78 8 used use VBN cord-276598-tm0yj2sn 78 9 for for IN cord-276598-tm0yj2sn 78 10 analysis analysis NN cord-276598-tm0yj2sn 78 11 of of IN cord-276598-tm0yj2sn 78 12 biomolecules biomolecule NNS cord-276598-tm0yj2sn 78 13 to to TO cord-276598-tm0yj2sn 78 14 improve improve VB cord-276598-tm0yj2sn 78 15 the the DT cord-276598-tm0yj2sn 78 16 ionization ionization NN cord-276598-tm0yj2sn 78 17 efficiency efficiency NN cord-276598-tm0yj2sn 78 18 and and CC cord-276598-tm0yj2sn 78 19 suppress suppress VB cord-276598-tm0yj2sn 78 20 matrix matrix NN cord-276598-tm0yj2sn 78 21 background background NN cord-276598-tm0yj2sn 78 22 signals signal NNS cord-276598-tm0yj2sn 78 23 [ [ -LRB- cord-276598-tm0yj2sn 78 24 44 44 CD cord-276598-tm0yj2sn 78 25 ] ] -RRB- cord-276598-tm0yj2sn 78 26 . . . cord-276598-tm0yj2sn 79 1 In in IN cord-276598-tm0yj2sn 79 2 addition addition NN cord-276598-tm0yj2sn 79 3 to to IN cord-276598-tm0yj2sn 79 4 this this DT cord-276598-tm0yj2sn 79 5 , , , cord-276598-tm0yj2sn 79 6 P P NNP cord-276598-tm0yj2sn 79 7 - - HYPH cord-276598-tm0yj2sn 79 8 Ns Ns NNP cord-276598-tm0yj2sn 79 9 have have VBP cord-276598-tm0yj2sn 79 10 found find VBN cord-276598-tm0yj2sn 79 11 novel novel JJ cord-276598-tm0yj2sn 79 12 applications application NNS cord-276598-tm0yj2sn 79 13 as as IN cord-276598-tm0yj2sn 79 14 task task NN cord-276598-tm0yj2sn 79 15 - - HYPH cord-276598-tm0yj2sn 79 16 specific specific JJ cord-276598-tm0yj2sn 79 17 ionic ionic JJ cord-276598-tm0yj2sn 79 18 liquids liquid NNS cord-276598-tm0yj2sn 79 19 ( ( -LRB- cord-276598-tm0yj2sn 79 20 TSILs TSILs NNP cord-276598-tm0yj2sn 79 21 ) ) -RRB- cord-276598-tm0yj2sn 79 22 , , , cord-276598-tm0yj2sn 79 23 which which WDT cord-276598-tm0yj2sn 79 24 are be VBP cord-276598-tm0yj2sn 79 25 tailored tailor VBN cord-276598-tm0yj2sn 79 26 ionic ionic JJ cord-276598-tm0yj2sn 79 27 liquids liquid NNS cord-276598-tm0yj2sn 79 28 having have VBG cord-276598-tm0yj2sn 79 29 a a DT cord-276598-tm0yj2sn 79 30 specific specific JJ cord-276598-tm0yj2sn 79 31 functionality functionality NN cord-276598-tm0yj2sn 79 32 to to IN cord-276598-tm0yj2sn 79 33 complex complex JJ cord-276598-tm0yj2sn 79 34 metal metal NN cord-276598-tm0yj2sn 79 35 ions ion NNS cord-276598-tm0yj2sn 79 36 . . . cord-276598-tm0yj2sn 80 1 Recently recently RB cord-276598-tm0yj2sn 80 2 , , , cord-276598-tm0yj2sn 80 3 these these DT cord-276598-tm0yj2sn 80 4 TSILs tsil NNS cord-276598-tm0yj2sn 80 5 have have VBP cord-276598-tm0yj2sn 80 6 been be VBN cord-276598-tm0yj2sn 80 7 used use VBN cord-276598-tm0yj2sn 80 8 for for IN cord-276598-tm0yj2sn 80 9 the the DT cord-276598-tm0yj2sn 80 10 efficient efficient JJ cord-276598-tm0yj2sn 80 11 extraction extraction NN cord-276598-tm0yj2sn 80 12 of of IN cord-276598-tm0yj2sn 80 13 uranium uranium NN cord-276598-tm0yj2sn 80 14 metal metal NN cord-276598-tm0yj2sn 80 15 , , , cord-276598-tm0yj2sn 80 16 which which WDT cord-276598-tm0yj2sn 80 17 is be VBZ cord-276598-tm0yj2sn 80 18 an an DT cord-276598-tm0yj2sn 80 19 important important JJ cord-276598-tm0yj2sn 80 20 element element NN cord-276598-tm0yj2sn 80 21 in in IN cord-276598-tm0yj2sn 80 22 nuclear nuclear JJ cord-276598-tm0yj2sn 80 23 fuel fuel NN cord-276598-tm0yj2sn 80 24 , , , cord-276598-tm0yj2sn 80 25 and and CC cord-276598-tm0yj2sn 80 26 the the DT cord-276598-tm0yj2sn 80 27 extraction extraction NN cord-276598-tm0yj2sn 80 28 of of IN cord-276598-tm0yj2sn 80 29 uranium uranium NN cord-276598-tm0yj2sn 80 30 metal metal NN cord-276598-tm0yj2sn 80 31 from from IN cord-276598-tm0yj2sn 80 32 the the DT cord-276598-tm0yj2sn 80 33 spent spend VBN cord-276598-tm0yj2sn 80 34 / / SYM cord-276598-tm0yj2sn 80 35 used use VBN cord-276598-tm0yj2sn 80 36 nuclear nuclear JJ cord-276598-tm0yj2sn 80 37 fuel fuel NN cord-276598-tm0yj2sn 80 38 is be VBZ cord-276598-tm0yj2sn 80 39 vital vital JJ cord-276598-tm0yj2sn 80 40 for for IN cord-276598-tm0yj2sn 80 41 the the DT cord-276598-tm0yj2sn 80 42 sustainable sustainable JJ cord-276598-tm0yj2sn 80 43 economy economy NN cord-276598-tm0yj2sn 80 44 [ [ -LRB- cord-276598-tm0yj2sn 80 45 45 45 CD cord-276598-tm0yj2sn 80 46 ] ] -RRB- cord-276598-tm0yj2sn 80 47 . . . cord-276598-tm0yj2sn 81 1 The the DT cord-276598-tm0yj2sn 81 2 enhanced enhanced JJ cord-276598-tm0yj2sn 81 3 extraction extraction NN cord-276598-tm0yj2sn 81 4 capabilities capability NNS cord-276598-tm0yj2sn 81 5 using use VBG cord-276598-tm0yj2sn 81 6 TSILs tsil NNS cord-276598-tm0yj2sn 81 7 in in IN cord-276598-tm0yj2sn 81 8 contrast contrast NN cord-276598-tm0yj2sn 81 9 to to IN cord-276598-tm0yj2sn 81 10 liquid liquid JJ cord-276598-tm0yj2sn 81 11 - - HYPH cord-276598-tm0yj2sn 81 12 liquid liquid NN cord-276598-tm0yj2sn 81 13 extraction extraction NN cord-276598-tm0yj2sn 81 14 could could MD cord-276598-tm0yj2sn 81 15 be be VB cord-276598-tm0yj2sn 81 16 attributed attribute VBN cord-276598-tm0yj2sn 81 17 to to IN cord-276598-tm0yj2sn 81 18 synergistic synergistic JJ cord-276598-tm0yj2sn 81 19 effects effect NNS cord-276598-tm0yj2sn 81 20 as as IN cord-276598-tm0yj2sn 81 21 a a DT cord-276598-tm0yj2sn 81 22 result result NN cord-276598-tm0yj2sn 81 23 of of IN cord-276598-tm0yj2sn 81 24 complexation complexation NN cord-276598-tm0yj2sn 81 25 and and CC cord-276598-tm0yj2sn 81 26 H h NN cord-276598-tm0yj2sn 81 27 - - HYPH cord-276598-tm0yj2sn 81 28 bonding bonding NN cord-276598-tm0yj2sn 81 29 [ [ -LRB- cord-276598-tm0yj2sn 81 30 17 17 CD cord-276598-tm0yj2sn 81 31 ] ] -RRB- cord-276598-tm0yj2sn 81 32 . . . cord-276598-tm0yj2sn 82 1 To to IN cord-276598-tm0yj2sn 82 2 this this DT cord-276598-tm0yj2sn 82 3 end end NN cord-276598-tm0yj2sn 82 4 , , , cord-276598-tm0yj2sn 82 5 these these DT cord-276598-tm0yj2sn 82 6 tailored tailor VBN cord-276598-tm0yj2sn 82 7 ionic ionic JJ cord-276598-tm0yj2sn 82 8 liquids liquid NNS cord-276598-tm0yj2sn 82 9 have have VBP cord-276598-tm0yj2sn 82 10 been be VBN cord-276598-tm0yj2sn 82 11 found find VBN cord-276598-tm0yj2sn 82 12 to to TO cord-276598-tm0yj2sn 82 13 be be VB cord-276598-tm0yj2sn 82 14 selective selective JJ cord-276598-tm0yj2sn 82 15 for for IN cord-276598-tm0yj2sn 82 16 the the DT cord-276598-tm0yj2sn 82 17 micellar micellar JJ cord-276598-tm0yj2sn 82 18 extraction extraction NN cord-276598-tm0yj2sn 82 19 of of IN cord-276598-tm0yj2sn 82 20 uranium uranium NN cord-276598-tm0yj2sn 82 21 metal metal NN cord-276598-tm0yj2sn 82 22 from from IN cord-276598-tm0yj2sn 82 23 aqueous aqueous JJ cord-276598-tm0yj2sn 82 24 waste waste NN cord-276598-tm0yj2sn 82 25 samples sample NNS cord-276598-tm0yj2sn 82 26 as as IN cord-276598-tm0yj2sn 82 27 even even RB cord-276598-tm0yj2sn 82 28 the the DT cord-276598-tm0yj2sn 82 29 ultra ultra JJ cord-276598-tm0yj2sn 82 30 - - JJ cord-276598-tm0yj2sn 82 31 trace trace JJ cord-276598-tm0yj2sn 82 32 levels level NNS cord-276598-tm0yj2sn 82 33 of of IN cord-276598-tm0yj2sn 82 34 uranium uranium NN cord-276598-tm0yj2sn 82 35 are be VBP cord-276598-tm0yj2sn 82 36 toxic toxic JJ cord-276598-tm0yj2sn 82 37 [ [ -LRB- cord-276598-tm0yj2sn 82 38 46 46 CD cord-276598-tm0yj2sn 82 39 ] ] -RRB- cord-276598-tm0yj2sn 82 40 . . . cord-276598-tm0yj2sn 83 1 P p NN cord-276598-tm0yj2sn 83 2 - - HYPH cord-276598-tm0yj2sn 83 3 Ns Ns NNP cord-276598-tm0yj2sn 83 4 act act NN cord-276598-tm0yj2sn 83 5 as as IN cord-276598-tm0yj2sn 83 6 1,3-N 1,3-n CD cord-276598-tm0yj2sn 83 7 , , , cord-276598-tm0yj2sn 83 8 O o NN cord-276598-tm0yj2sn 83 9 - - HYPH cord-276598-tm0yj2sn 83 10 chelating chelate VBG cord-276598-tm0yj2sn 83 11 ligands ligand NNS cord-276598-tm0yj2sn 83 12 ( ( -LRB- cord-276598-tm0yj2sn 83 13 e.g. e.g. RB cord-276598-tm0yj2sn 83 14 , , , cord-276598-tm0yj2sn 83 15 Figure figure NN cord-276598-tm0yj2sn 83 16 3 3 CD cord-276598-tm0yj2sn 83 17 , , , cord-276598-tm0yj2sn 83 18 Ligand Ligand NNP cord-276598-tm0yj2sn 83 19 ) ) -RRB- cord-276598-tm0yj2sn 83 20 and and CC cord-276598-tm0yj2sn 83 21 have have VBP cord-276598-tm0yj2sn 83 22 diverse diverse JJ cord-276598-tm0yj2sn 83 23 applications application NNS cord-276598-tm0yj2sn 83 24 in in IN cord-276598-tm0yj2sn 83 25 the the DT cord-276598-tm0yj2sn 83 26 field field NN cord-276598-tm0yj2sn 83 27 of of IN cord-276598-tm0yj2sn 83 28 coordination coordination NN cord-276598-tm0yj2sn 83 29 chemistry chemistry NN cord-276598-tm0yj2sn 83 30 for for IN cord-276598-tm0yj2sn 83 31 bond bond NN cord-276598-tm0yj2sn 83 32 activation activation NN cord-276598-tm0yj2sn 83 33 , , , cord-276598-tm0yj2sn 83 34 catalysis catalysis NN cord-276598-tm0yj2sn 83 35 , , , cord-276598-tm0yj2sn 83 36 and and CC cord-276598-tm0yj2sn 83 37 metal metal NN cord-276598-tm0yj2sn 83 38 ligand ligand NN cord-276598-tm0yj2sn 83 39 cooperativity cooperativity NN cord-276598-tm0yj2sn 83 40 [ [ -LRB- cord-276598-tm0yj2sn 83 41 47 47 CD cord-276598-tm0yj2sn 83 42 ] ] -RRB- cord-276598-tm0yj2sn 84 1 [ [ -LRB- cord-276598-tm0yj2sn 84 2 48 48 CD cord-276598-tm0yj2sn 84 3 ] ] -RRB- cord-276598-tm0yj2sn 84 4 [ [ -LRB- cord-276598-tm0yj2sn 84 5 49 49 CD cord-276598-tm0yj2sn 84 6 ] ] -RRB- cord-276598-tm0yj2sn 84 7 . . . cord-276598-tm0yj2sn 85 1 For for IN cord-276598-tm0yj2sn 85 2 example example NN cord-276598-tm0yj2sn 85 3 , , , cord-276598-tm0yj2sn 85 4 a a DT cord-276598-tm0yj2sn 85 5 P P NNP cord-276598-tm0yj2sn 85 6 - - HYPH cord-276598-tm0yj2sn 85 7 N n NN cord-276598-tm0yj2sn 85 8 - - HYPH cord-276598-tm0yj2sn 85 9 tantalum tantalum NN cord-276598-tm0yj2sn 85 10 complex complex NN cord-276598-tm0yj2sn 85 11 has have VBZ cord-276598-tm0yj2sn 85 12 been be VBN cord-276598-tm0yj2sn 85 13 developed develop VBN cord-276598-tm0yj2sn 85 14 as as IN cord-276598-tm0yj2sn 85 15 a a DT cord-276598-tm0yj2sn 85 16 pre pre NN cord-276598-tm0yj2sn 85 17 - - NN cord-276598-tm0yj2sn 85 18 catalyst catalyst NN cord-276598-tm0yj2sn 85 19 for for IN cord-276598-tm0yj2sn 85 20 hydroaminoalkylation hydroaminoalkylation NN cord-276598-tm0yj2sn 85 21 reactions reaction NNS cord-276598-tm0yj2sn 85 22 [ [ -LRB- cord-276598-tm0yj2sn 85 23 50 50 CD cord-276598-tm0yj2sn 85 24 ] ] -RRB- cord-276598-tm0yj2sn 85 25 . . . cord-276598-tm0yj2sn 86 1 In in IN cord-276598-tm0yj2sn 86 2 addition addition NN cord-276598-tm0yj2sn 86 3 , , , cord-276598-tm0yj2sn 86 4 the the DT cord-276598-tm0yj2sn 86 5 synthesis synthesis NN cord-276598-tm0yj2sn 86 6 of of IN cord-276598-tm0yj2sn 86 7 medium medium JJ cord-276598-tm0yj2sn 86 8 and and CC cord-276598-tm0yj2sn 86 9 large large JJ cord-276598-tm0yj2sn 86 10 N n CD cord-276598-tm0yj2sn 86 11 - - HYPH cord-276598-tm0yj2sn 86 12 based base VBN cord-276598-tm0yj2sn 86 13 heterocycles heterocycle NNS cord-276598-tm0yj2sn 86 14 has have VBZ cord-276598-tm0yj2sn 86 15 been be VBN cord-276598-tm0yj2sn 86 16 achieved achieve VBN cord-276598-tm0yj2sn 86 17 with with IN cord-276598-tm0yj2sn 86 18 the the DT cord-276598-tm0yj2sn 86 19 aid aid NN cord-276598-tm0yj2sn 86 20 of of IN cord-276598-tm0yj2sn 86 21 P p NN cord-276598-tm0yj2sn 86 22 - - HYPH cord-276598-tm0yj2sn 86 23 Ns Ns NNP cord-276598-tm0yj2sn 86 24 , , , cord-276598-tm0yj2sn 86 25 as as IN cord-276598-tm0yj2sn 86 26 the the DT cord-276598-tm0yj2sn 86 27 phosphoryl phosphoryl NNP cord-276598-tm0yj2sn 86 28 group group NN cord-276598-tm0yj2sn 86 29 improves improve VBZ cord-276598-tm0yj2sn 86 30 intramolecular intramolecular JJ cord-276598-tm0yj2sn 86 31 cyclization cyclization NN cord-276598-tm0yj2sn 86 32 , , , cord-276598-tm0yj2sn 86 33 and and CC cord-276598-tm0yj2sn 86 34 it -PRON- PRP cord-276598-tm0yj2sn 86 35 can can MD cord-276598-tm0yj2sn 86 36 also also RB cord-276598-tm0yj2sn 86 37 be be VB cord-276598-tm0yj2sn 86 38 easily easily RB cord-276598-tm0yj2sn 86 39 removed remove VBN cord-276598-tm0yj2sn 86 40 afterwards afterwards RB cord-276598-tm0yj2sn 86 41 [ [ -LRB- cord-276598-tm0yj2sn 86 42 51 51 CD cord-276598-tm0yj2sn 86 43 ] ] -RRB- cord-276598-tm0yj2sn 86 44 . . . cord-276598-tm0yj2sn 87 1 Furthermore furthermore RB cord-276598-tm0yj2sn 87 2 , , , cord-276598-tm0yj2sn 87 3 P P NNP cord-276598-tm0yj2sn 87 4 - - HYPH cord-276598-tm0yj2sn 87 5 Ns Ns NNP cord-276598-tm0yj2sn 87 6 have have VBP cord-276598-tm0yj2sn 87 7 been be VBN cord-276598-tm0yj2sn 87 8 used use VBN cord-276598-tm0yj2sn 87 9 as as IN cord-276598-tm0yj2sn 87 10 directing direct VBG cord-276598-tm0yj2sn 87 11 groups group NNS cord-276598-tm0yj2sn 87 12 for for IN cord-276598-tm0yj2sn 87 13 arylation arylation NN cord-276598-tm0yj2sn 87 14 reactions reaction NNS cord-276598-tm0yj2sn 87 15 , , , cord-276598-tm0yj2sn 87 16 as as IN cord-276598-tm0yj2sn 87 17 they -PRON- PRP cord-276598-tm0yj2sn 87 18 selectively selectively RB cord-276598-tm0yj2sn 87 19 activate activate VBP cord-276598-tm0yj2sn 87 20 C C NNP cord-276598-tm0yj2sn 87 21 - - HYPH cord-276598-tm0yj2sn 87 22 H H NNP cord-276598-tm0yj2sn 87 23 bonds bond NNS cord-276598-tm0yj2sn 87 24 , , , cord-276598-tm0yj2sn 87 25 and and CC cord-276598-tm0yj2sn 87 26 thus thus RB cord-276598-tm0yj2sn 87 27 , , , cord-276598-tm0yj2sn 87 28 desired desire VBN cord-276598-tm0yj2sn 87 29 functionality functionality NN cord-276598-tm0yj2sn 87 30 can can MD cord-276598-tm0yj2sn 87 31 be be VB cord-276598-tm0yj2sn 87 32 achieved achieve VBN cord-276598-tm0yj2sn 87 33 [ [ -LRB- cord-276598-tm0yj2sn 87 34 52 52 CD cord-276598-tm0yj2sn 87 35 ] ] -RRB- cord-276598-tm0yj2sn 87 36 . . . cord-276598-tm0yj2sn 88 1 P p NN cord-276598-tm0yj2sn 88 2 - - HYPH cord-276598-tm0yj2sn 88 3 Ns Ns NNP cord-276598-tm0yj2sn 88 4 have have VBP cord-276598-tm0yj2sn 88 5 garnered garner VBN cord-276598-tm0yj2sn 88 6 considerable considerable JJ cord-276598-tm0yj2sn 88 7 interest interest NN cord-276598-tm0yj2sn 88 8 in in IN cord-276598-tm0yj2sn 88 9 the the DT cord-276598-tm0yj2sn 88 10 field field NN cord-276598-tm0yj2sn 88 11 of of IN cord-276598-tm0yj2sn 88 12 biomedicine biomedicine NN cord-276598-tm0yj2sn 88 13 due due IN cord-276598-tm0yj2sn 88 14 to to IN cord-276598-tm0yj2sn 88 15 their -PRON- PRP$ cord-276598-tm0yj2sn 88 16 potential potential JJ cord-276598-tm0yj2sn 88 17 applications application NNS cord-276598-tm0yj2sn 88 18 as as IN cord-276598-tm0yj2sn 88 19 antimicrobial antimicrobial JJ cord-276598-tm0yj2sn 88 20 [ [ -LRB- cord-276598-tm0yj2sn 88 21 53 53 CD cord-276598-tm0yj2sn 88 22 ] ] -RRB- cord-276598-tm0yj2sn 88 23 [ [ -LRB- cord-276598-tm0yj2sn 88 24 54 54 CD cord-276598-tm0yj2sn 88 25 ] ] -RRB- cord-276598-tm0yj2sn 88 26 [ [ -LRB- cord-276598-tm0yj2sn 88 27 55 55 CD cord-276598-tm0yj2sn 88 28 ] ] -RRB- cord-276598-tm0yj2sn 88 29 , , , cord-276598-tm0yj2sn 88 30 antioxidant antioxidant JJ cord-276598-tm0yj2sn 88 31 [ [ -LRB- cord-276598-tm0yj2sn 88 32 56 56 CD cord-276598-tm0yj2sn 88 33 ] ] -RRB- cord-276598-tm0yj2sn 88 34 , , , cord-276598-tm0yj2sn 88 35 anticancer anticancer JJ cord-276598-tm0yj2sn 88 36 [ [ -LRB- cord-276598-tm0yj2sn 88 37 57 57 CD cord-276598-tm0yj2sn 88 38 ] ] -RRB- cord-276598-tm0yj2sn 88 39 , , , cord-276598-tm0yj2sn 88 40 antimalarial antimalarial JJ cord-276598-tm0yj2sn 88 41 [ [ -LRB- cord-276598-tm0yj2sn 88 42 58 58 CD cord-276598-tm0yj2sn 88 43 ] ] -RRB- cord-276598-tm0yj2sn 88 44 , , , cord-276598-tm0yj2sn 88 45 antiviral antiviral JJ cord-276598-tm0yj2sn 88 46 [ [ -LRB- cord-276598-tm0yj2sn 88 47 59 59 CD cord-276598-tm0yj2sn 88 48 , , , cord-276598-tm0yj2sn 88 49 60 60 CD cord-276598-tm0yj2sn 88 50 ] ] -RRB- cord-276598-tm0yj2sn 88 51 , , , cord-276598-tm0yj2sn 88 52 and and CC cord-276598-tm0yj2sn 88 53 anti anti JJ cord-276598-tm0yj2sn 88 54 - - JJ cord-276598-tm0yj2sn 88 55 HIV HIV NNP cord-276598-tm0yj2sn 88 56 [ [ -LRB- cord-276598-tm0yj2sn 88 57 61 61 CD cord-276598-tm0yj2sn 88 58 ] ] -RRB- cord-276598-tm0yj2sn 88 59 drugs drug NNS cord-276598-tm0yj2sn 88 60 and and CC cord-276598-tm0yj2sn 88 61 prodrugs prodrug NNS cord-276598-tm0yj2sn 88 62 against against IN cord-276598-tm0yj2sn 88 63 various various JJ cord-276598-tm0yj2sn 88 64 ailments ailment NNS cord-276598-tm0yj2sn 88 65 ( ( -LRB- cord-276598-tm0yj2sn 88 66 Figure figure NN cord-276598-tm0yj2sn 88 67 3 3 CD cord-276598-tm0yj2sn 88 68 ) ) -RRB- cord-276598-tm0yj2sn 88 69 . . . cord-276598-tm0yj2sn 89 1 The the DT cord-276598-tm0yj2sn 89 2 ProTide ProTide NNP cord-276598-tm0yj2sn 89 3 approach approach NN cord-276598-tm0yj2sn 89 4 , , , cord-276598-tm0yj2sn 89 5 pioneered pioneer VBN cord-276598-tm0yj2sn 89 6 by by IN cord-276598-tm0yj2sn 89 7 the the DT cord-276598-tm0yj2sn 89 8 McGuigan McGuigan NNP cord-276598-tm0yj2sn 89 9 group group NN cord-276598-tm0yj2sn 89 10 in in IN cord-276598-tm0yj2sn 89 11 1992 1992 CD cord-276598-tm0yj2sn 89 12 for for IN cord-276598-tm0yj2sn 89 13 drug drug NN cord-276598-tm0yj2sn 89 14 delivery delivery NN cord-276598-tm0yj2sn 89 15 , , , cord-276598-tm0yj2sn 89 16 is be VBZ cord-276598-tm0yj2sn 89 17 a a DT cord-276598-tm0yj2sn 89 18 powerful powerful JJ cord-276598-tm0yj2sn 89 19 tool tool NN cord-276598-tm0yj2sn 89 20 to to TO cord-276598-tm0yj2sn 89 21 enhance enhance VB cord-276598-tm0yj2sn 89 22 the the DT cord-276598-tm0yj2sn 89 23 efficacy efficacy NN cord-276598-tm0yj2sn 89 24 , , , cord-276598-tm0yj2sn 89 25 intracellular intracellular JJ cord-276598-tm0yj2sn 89 26 delivery delivery NN cord-276598-tm0yj2sn 89 27 , , , cord-276598-tm0yj2sn 89 28 and and CC cord-276598-tm0yj2sn 89 29 therapeutic therapeutic JJ cord-276598-tm0yj2sn 89 30 potential potential NN cord-276598-tm0yj2sn 89 31 of of IN cord-276598-tm0yj2sn 89 32 the the DT cord-276598-tm0yj2sn 89 33 parent parent NN cord-276598-tm0yj2sn 89 34 drugs drug NNS cord-276598-tm0yj2sn 89 35 [ [ -LRB- cord-276598-tm0yj2sn 89 36 62 62 CD cord-276598-tm0yj2sn 89 37 , , , cord-276598-tm0yj2sn 89 38 63 63 CD cord-276598-tm0yj2sn 89 39 ] ] -RRB- cord-276598-tm0yj2sn 89 40 . . . cord-276598-tm0yj2sn 90 1 Recently recently RB cord-276598-tm0yj2sn 90 2 , , , cord-276598-tm0yj2sn 90 3 remdesivir remdesivir NNP cord-276598-tm0yj2sn 90 4 ( ( -LRB- cord-276598-tm0yj2sn 90 5 Figure figure NN cord-276598-tm0yj2sn 90 6 3 3 CD cord-276598-tm0yj2sn 90 7 , , , cord-276598-tm0yj2sn 90 8 drug drug NN cord-276598-tm0yj2sn 90 9 candidate candidate NN cord-276598-tm0yj2sn 90 10 ) ) -RRB- cord-276598-tm0yj2sn 90 11 , , , cord-276598-tm0yj2sn 90 12 which which WDT cord-276598-tm0yj2sn 90 13 has have VBZ cord-276598-tm0yj2sn 90 14 a a DT cord-276598-tm0yj2sn 90 15 P P NNP cord-276598-tm0yj2sn 90 16 - - HYPH cord-276598-tm0yj2sn 90 17 N N NNP cord-276598-tm0yj2sn 90 18 moiety moiety NN cord-276598-tm0yj2sn 90 19 , , , cord-276598-tm0yj2sn 90 20 has have VBZ cord-276598-tm0yj2sn 90 21 been be VBN cord-276598-tm0yj2sn 90 22 evaluated evaluate VBN cord-276598-tm0yj2sn 90 23 as as IN cord-276598-tm0yj2sn 90 24 a a DT cord-276598-tm0yj2sn 90 25 therapeutic therapeutic JJ cord-276598-tm0yj2sn 90 26 option option NN cord-276598-tm0yj2sn 90 27 for for IN cord-276598-tm0yj2sn 90 28 the the DT cord-276598-tm0yj2sn 90 29 treatment treatment NN cord-276598-tm0yj2sn 90 30 of of IN cord-276598-tm0yj2sn 90 31 COVID-19-affected covid-19-affecte VBN cord-276598-tm0yj2sn 90 32 patients patient NNS cord-276598-tm0yj2sn 90 33 and and CC cord-276598-tm0yj2sn 90 34 has have VBZ cord-276598-tm0yj2sn 90 35 attracted attract VBN cord-276598-tm0yj2sn 90 36 a a DT cord-276598-tm0yj2sn 90 37 lot lot NN cord-276598-tm0yj2sn 90 38 of of IN cord-276598-tm0yj2sn 90 39 attention attention NN cord-276598-tm0yj2sn 90 40 in in IN cord-276598-tm0yj2sn 90 41 the the DT cord-276598-tm0yj2sn 90 42 clinical clinical JJ cord-276598-tm0yj2sn 90 43 field field NN cord-276598-tm0yj2sn 90 44 [ [ -LRB- cord-276598-tm0yj2sn 90 45 64 64 CD cord-276598-tm0yj2sn 90 46 ] ] -RRB- cord-276598-tm0yj2sn 90 47 . . . cord-276598-tm0yj2sn 91 1 Additionally additionally RB cord-276598-tm0yj2sn 91 2 , , , cord-276598-tm0yj2sn 91 3 these these DT cord-276598-tm0yj2sn 91 4 P P NNP cord-276598-tm0yj2sn 91 5 - - HYPH cord-276598-tm0yj2sn 91 6 N N NNP cord-276598-tm0yj2sn 91 7 compounds compound NNS cord-276598-tm0yj2sn 91 8 have have VBP cord-276598-tm0yj2sn 91 9 been be VBN cord-276598-tm0yj2sn 91 10 used use VBN cord-276598-tm0yj2sn 91 11 in in IN cord-276598-tm0yj2sn 91 12 gene gene NN cord-276598-tm0yj2sn 91 13 therapy therapy NN cord-276598-tm0yj2sn 91 14 and and CC cord-276598-tm0yj2sn 91 15 nucleoside nucleoside NN cord-276598-tm0yj2sn 91 16 treatment treatment NN cord-276598-tm0yj2sn 91 17 [ [ -LRB- cord-276598-tm0yj2sn 91 18 65 65 CD cord-276598-tm0yj2sn 91 19 ] ] -RRB- cord-276598-tm0yj2sn 92 1 [ [ -LRB- cord-276598-tm0yj2sn 92 2 66 66 CD cord-276598-tm0yj2sn 92 3 ] ] -RRB- cord-276598-tm0yj2sn 92 4 [ [ -LRB- cord-276598-tm0yj2sn 92 5 67 67 CD cord-276598-tm0yj2sn 92 6 ] ] -RRB- cord-276598-tm0yj2sn 92 7 . . . cord-276598-tm0yj2sn 93 1 Moreover moreover RB cord-276598-tm0yj2sn 93 2 , , , cord-276598-tm0yj2sn 93 3 many many JJ cord-276598-tm0yj2sn 93 4 P p NN cord-276598-tm0yj2sn 93 5 - - HYPH cord-276598-tm0yj2sn 93 6 Ns Ns NNP cord-276598-tm0yj2sn 93 7 have have VBP cord-276598-tm0yj2sn 93 8 been be VBN cord-276598-tm0yj2sn 93 9 found find VBN cord-276598-tm0yj2sn 93 10 to to TO cord-276598-tm0yj2sn 93 11 be be VB cord-276598-tm0yj2sn 93 12 hydrolytically hydrolytically RB cord-276598-tm0yj2sn 93 13 degradable degradable JJ cord-276598-tm0yj2sn 93 14 under under IN cord-276598-tm0yj2sn 93 15 acidic acidic JJ cord-276598-tm0yj2sn 93 16 conditions condition NNS cord-276598-tm0yj2sn 93 17 and and CC cord-276598-tm0yj2sn 93 18 are be VBP cord-276598-tm0yj2sn 93 19 comparatively comparatively RB cord-276598-tm0yj2sn 93 20 stable stable JJ cord-276598-tm0yj2sn 93 21 at at IN cord-276598-tm0yj2sn 93 22 neutral neutral JJ cord-276598-tm0yj2sn 93 23 and and CC cord-276598-tm0yj2sn 93 24 higher high JJR cord-276598-tm0yj2sn 93 25 pHs ph NNS cord-276598-tm0yj2sn 93 26 . . . cord-276598-tm0yj2sn 94 1 The the DT cord-276598-tm0yj2sn 94 2 acid acid NN cord-276598-tm0yj2sn 94 3 labile labile JJ cord-276598-tm0yj2sn 94 4 P p NN cord-276598-tm0yj2sn 94 5 - - HYPH cord-276598-tm0yj2sn 94 6 N n CD cord-276598-tm0yj2sn 94 7 bond bond NN cord-276598-tm0yj2sn 94 8 is be VBZ cord-276598-tm0yj2sn 94 9 selectively selectively RB cord-276598-tm0yj2sn 94 10 cleaved cleave VBN cord-276598-tm0yj2sn 94 11 due due IN cord-276598-tm0yj2sn 94 12 to to IN cord-276598-tm0yj2sn 94 13 protonation protonation NN cord-276598-tm0yj2sn 94 14 at at IN cord-276598-tm0yj2sn 94 15 N n CD cord-276598-tm0yj2sn 94 16 , , , cord-276598-tm0yj2sn 94 17 which which WDT cord-276598-tm0yj2sn 94 18 then then RB cord-276598-tm0yj2sn 94 19 undergoes undergo VBZ cord-276598-tm0yj2sn 94 20 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 94 21 attack attack NN cord-276598-tm0yj2sn 94 22 by by IN cord-276598-tm0yj2sn 94 23 a a DT cord-276598-tm0yj2sn 94 24 molecule molecule NN cord-276598-tm0yj2sn 94 25 of of IN cord-276598-tm0yj2sn 94 26 water water NN cord-276598-tm0yj2sn 94 27 to to TO cord-276598-tm0yj2sn 94 28 eliminate eliminate VB cord-276598-tm0yj2sn 94 29 the the DT cord-276598-tm0yj2sn 94 30 corresponding corresponding JJ cord-276598-tm0yj2sn 94 31 phosphates phosphate NNS cord-276598-tm0yj2sn 94 32 and and CC cord-276598-tm0yj2sn 94 33 amines amine NNS cord-276598-tm0yj2sn 94 34 [ [ -LRB- cord-276598-tm0yj2sn 94 35 68 68 CD cord-276598-tm0yj2sn 94 36 , , , cord-276598-tm0yj2sn 94 37 69 69 CD cord-276598-tm0yj2sn 94 38 ] ] -RRB- cord-276598-tm0yj2sn 94 39 . . . cord-276598-tm0yj2sn 95 1 Thus thus RB cord-276598-tm0yj2sn 95 2 , , , cord-276598-tm0yj2sn 95 3 these these DT cord-276598-tm0yj2sn 95 4 pH pH NNP cord-276598-tm0yj2sn 95 5 responsive responsive JJ cord-276598-tm0yj2sn 95 6 P P NNP cord-276598-tm0yj2sn 95 7 - - HYPH cord-276598-tm0yj2sn 95 8 Ns Ns NNP cord-276598-tm0yj2sn 95 9 have have VBP cord-276598-tm0yj2sn 95 10 notable notable JJ cord-276598-tm0yj2sn 95 11 applications application NNS cord-276598-tm0yj2sn 95 12 in in IN cord-276598-tm0yj2sn 95 13 controlled control VBN cord-276598-tm0yj2sn 95 14 drug drug NN cord-276598-tm0yj2sn 95 15 release release NN cord-276598-tm0yj2sn 95 16 [ [ -LRB- cord-276598-tm0yj2sn 95 17 70 70 CD cord-276598-tm0yj2sn 95 18 , , , cord-276598-tm0yj2sn 95 19 71 71 CD cord-276598-tm0yj2sn 95 20 ] ] -RRB- cord-276598-tm0yj2sn 95 21 . . . cord-276598-tm0yj2sn 96 1 For for IN cord-276598-tm0yj2sn 96 2 example example NN cord-276598-tm0yj2sn 96 3 , , , cord-276598-tm0yj2sn 96 4 the the DT cord-276598-tm0yj2sn 96 5 P P NNP cord-276598-tm0yj2sn 96 6 - - HYPH cord-276598-tm0yj2sn 96 7 N N NNP cord-276598-tm0yj2sn 96 8 - - HYPH cord-276598-tm0yj2sn 96 9 based base VBN cord-276598-tm0yj2sn 96 10 prodrug prodrug NN cord-276598-tm0yj2sn 96 11 of of IN cord-276598-tm0yj2sn 96 12 l l NNP cord-276598-tm0yj2sn 96 13 - - HYPH cord-276598-tm0yj2sn 96 14 Dopa Dopa NNP cord-276598-tm0yj2sn 96 15 has have VBZ cord-276598-tm0yj2sn 96 16 been be VBN cord-276598-tm0yj2sn 96 17 synthesized synthesize VBN cord-276598-tm0yj2sn 96 18 for for IN cord-276598-tm0yj2sn 96 19 its -PRON- PRP$ cord-276598-tm0yj2sn 96 20 controlled controlled JJ cord-276598-tm0yj2sn 96 21 release release NN cord-276598-tm0yj2sn 96 22 for for IN cord-276598-tm0yj2sn 96 23 the the DT cord-276598-tm0yj2sn 96 24 treatment treatment NN cord-276598-tm0yj2sn 96 25 of of IN cord-276598-tm0yj2sn 96 26 Parkinson Parkinson NNP cord-276598-tm0yj2sn 96 27 's 's POS cord-276598-tm0yj2sn 96 28 disease disease NN cord-276598-tm0yj2sn 96 29 [ [ -LRB- cord-276598-tm0yj2sn 96 30 72 72 CD cord-276598-tm0yj2sn 96 31 ] ] -RRB- cord-276598-tm0yj2sn 96 32 . . . cord-276598-tm0yj2sn 97 1 Similarly similarly RB cord-276598-tm0yj2sn 97 2 , , , cord-276598-tm0yj2sn 97 3 P P NNP cord-276598-tm0yj2sn 97 4 - - HYPH cord-276598-tm0yj2sn 97 5 N n CD cord-276598-tm0yj2sn 97 6 derivatives derivative NNS cord-276598-tm0yj2sn 97 7 of of IN cord-276598-tm0yj2sn 97 8 the the DT cord-276598-tm0yj2sn 97 9 antiherpetic antiherpetic JJ cord-276598-tm0yj2sn 97 10 drug drug NN cord-276598-tm0yj2sn 97 11 , , , cord-276598-tm0yj2sn 97 12 acyclovir acyclovir NNP cord-276598-tm0yj2sn 97 13 ( ( -LRB- cord-276598-tm0yj2sn 97 14 ACV ACV NNP cord-276598-tm0yj2sn 97 15 ) ) -RRB- cord-276598-tm0yj2sn 97 16 , , , cord-276598-tm0yj2sn 97 17 hydrolyses hydrolyse VBZ cord-276598-tm0yj2sn 97 18 at at IN cord-276598-tm0yj2sn 97 19 pH pH NNP cord-276598-tm0yj2sn 97 20 2 2 CD cord-276598-tm0yj2sn 97 21 into into IN cord-276598-tm0yj2sn 97 22 ACV acv NN cord-276598-tm0yj2sn 97 23 monophosphate monophosphate NN cord-276598-tm0yj2sn 97 24 and and CC cord-276598-tm0yj2sn 97 25 can can MD cord-276598-tm0yj2sn 97 26 be be VB cord-276598-tm0yj2sn 97 27 a a DT cord-276598-tm0yj2sn 97 28 promising promising JJ cord-276598-tm0yj2sn 97 29 antiviral antiviral JJ cord-276598-tm0yj2sn 97 30 drug drug NN cord-276598-tm0yj2sn 97 31 due due IN cord-276598-tm0yj2sn 97 32 to to IN cord-276598-tm0yj2sn 97 33 increased increase VBN cord-276598-tm0yj2sn 97 34 cell cell NN cord-276598-tm0yj2sn 97 35 penetration penetration NN cord-276598-tm0yj2sn 97 36 and and CC cord-276598-tm0yj2sn 97 37 therapeutic therapeutic JJ cord-276598-tm0yj2sn 97 38 potential potential JJ cord-276598-tm0yj2sn 97 39 relative relative NN cord-276598-tm0yj2sn 97 40 to to IN cord-276598-tm0yj2sn 97 41 the the DT cord-276598-tm0yj2sn 97 42 parent parent NN cord-276598-tm0yj2sn 97 43 drug drug NN cord-276598-tm0yj2sn 97 44 [ [ -LRB- cord-276598-tm0yj2sn 97 45 73 73 CD cord-276598-tm0yj2sn 97 46 ] ] -RRB- cord-276598-tm0yj2sn 97 47 . . . cord-276598-tm0yj2sn 98 1 Although although IN cord-276598-tm0yj2sn 98 2 P P NNP cord-276598-tm0yj2sn 98 3 - - HYPH cord-276598-tm0yj2sn 98 4 N n NN cord-276598-tm0yj2sn 98 5 biomolecules biomolecule NNS cord-276598-tm0yj2sn 98 6 such such JJ cord-276598-tm0yj2sn 98 7 as as IN cord-276598-tm0yj2sn 98 8 phosphocreatine phosphocreatine NN cord-276598-tm0yj2sn 98 9 have have VBP cord-276598-tm0yj2sn 98 10 been be VBN cord-276598-tm0yj2sn 98 11 known know VBN cord-276598-tm0yj2sn 98 12 since since IN cord-276598-tm0yj2sn 98 13 the the DT cord-276598-tm0yj2sn 98 14 work work NN cord-276598-tm0yj2sn 98 15 of of IN cord-276598-tm0yj2sn 98 16 Fiske Fiske NNP cord-276598-tm0yj2sn 98 17 and and CC cord-276598-tm0yj2sn 98 18 Subbarow Subbarow NNP cord-276598-tm0yj2sn 98 19 in in IN cord-276598-tm0yj2sn 98 20 1927 1927 CD cord-276598-tm0yj2sn 98 21 , , , cord-276598-tm0yj2sn 98 22 synthetic synthetic JJ cord-276598-tm0yj2sn 98 23 routes route NNS cord-276598-tm0yj2sn 98 24 to to IN cord-276598-tm0yj2sn 98 25 P P NNP cord-276598-tm0yj2sn 98 26 - - HYPH cord-276598-tm0yj2sn 98 27 N N NNP cord-276598-tm0yj2sn 98 28 compounds compound NNS cord-276598-tm0yj2sn 98 29 prior prior RB cord-276598-tm0yj2sn 98 30 to to IN cord-276598-tm0yj2sn 98 31 1988 1988 CD cord-276598-tm0yj2sn 98 32 have have VBP cord-276598-tm0yj2sn 98 33 been be VBN cord-276598-tm0yj2sn 98 34 limited limit VBN cord-276598-tm0yj2sn 98 35 [ [ -LRB- cord-276598-tm0yj2sn 98 36 74 74 CD cord-276598-tm0yj2sn 98 37 , , , cord-276598-tm0yj2sn 98 38 75 75 CD cord-276598-tm0yj2sn 98 39 ] ] -RRB- cord-276598-tm0yj2sn 98 40 . . . cord-276598-tm0yj2sn 99 1 These these DT cord-276598-tm0yj2sn 99 2 early early JJ cord-276598-tm0yj2sn 99 3 routes route NNS cord-276598-tm0yj2sn 99 4 involve involve VBP cord-276598-tm0yj2sn 99 5 the the DT cord-276598-tm0yj2sn 99 6 preparation preparation NN cord-276598-tm0yj2sn 99 7 of of IN cord-276598-tm0yj2sn 99 8 and and CC cord-276598-tm0yj2sn 99 9 use use NN cord-276598-tm0yj2sn 99 10 of of IN cord-276598-tm0yj2sn 99 11 toxic toxic JJ cord-276598-tm0yj2sn 99 12 reagents reagent NNS cord-276598-tm0yj2sn 99 13 over over IN cord-276598-tm0yj2sn 99 14 multiple multiple JJ cord-276598-tm0yj2sn 99 15 synthetic synthetic JJ cord-276598-tm0yj2sn 99 16 steps step NNS cord-276598-tm0yj2sn 99 17 and and CC cord-276598-tm0yj2sn 99 18 often often RB cord-276598-tm0yj2sn 99 19 resulted result VBD cord-276598-tm0yj2sn 99 20 in in IN cord-276598-tm0yj2sn 99 21 the the DT cord-276598-tm0yj2sn 99 22 elimination elimination NN cord-276598-tm0yj2sn 99 23 of of IN cord-276598-tm0yj2sn 99 24 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 99 25 waste waste NN cord-276598-tm0yj2sn 99 26 . . . cord-276598-tm0yj2sn 100 1 However however RB cord-276598-tm0yj2sn 100 2 , , , cord-276598-tm0yj2sn 100 3 with with IN cord-276598-tm0yj2sn 100 4 an an DT cord-276598-tm0yj2sn 100 5 increase increase NN cord-276598-tm0yj2sn 100 6 in in IN cord-276598-tm0yj2sn 100 7 the the DT cord-276598-tm0yj2sn 100 8 number number NN cord-276598-tm0yj2sn 100 9 of of IN cord-276598-tm0yj2sn 100 10 uses use NNS cord-276598-tm0yj2sn 100 11 of of IN cord-276598-tm0yj2sn 100 12 P P NNP cord-276598-tm0yj2sn 100 13 - - HYPH cord-276598-tm0yj2sn 100 14 Ns Ns NNP cord-276598-tm0yj2sn 100 15 , , , cord-276598-tm0yj2sn 100 16 the the DT cord-276598-tm0yj2sn 100 17 need need NN cord-276598-tm0yj2sn 100 18 to to TO cord-276598-tm0yj2sn 100 19 develop develop VB cord-276598-tm0yj2sn 100 20 one one CD cord-276598-tm0yj2sn 100 21 - - HYPH cord-276598-tm0yj2sn 100 22 pot pot NN cord-276598-tm0yj2sn 100 23 synthetic synthetic JJ cord-276598-tm0yj2sn 100 24 routes route NNS cord-276598-tm0yj2sn 100 25 that that WDT cord-276598-tm0yj2sn 100 26 are be VBP cord-276598-tm0yj2sn 100 27 more more RBR cord-276598-tm0yj2sn 100 28 environmentally environmentally RB cord-276598-tm0yj2sn 100 29 benign benign JJ cord-276598-tm0yj2sn 100 30 has have VBZ cord-276598-tm0yj2sn 100 31 driven drive VBN cord-276598-tm0yj2sn 100 32 researchers researcher NNS cord-276598-tm0yj2sn 100 33 to to TO cord-276598-tm0yj2sn 100 34 discover discover VB cord-276598-tm0yj2sn 100 35 catalytic catalytic JJ cord-276598-tm0yj2sn 100 36 strategies strategy NNS cord-276598-tm0yj2sn 100 37 . . . cord-276598-tm0yj2sn 101 1 Accordingly accordingly RB cord-276598-tm0yj2sn 101 2 , , , cord-276598-tm0yj2sn 101 3 all all PDT cord-276598-tm0yj2sn 101 4 the the DT cord-276598-tm0yj2sn 101 5 known know VBN cord-276598-tm0yj2sn 101 6 synthetic synthetic JJ cord-276598-tm0yj2sn 101 7 routes route NNS cord-276598-tm0yj2sn 101 8 to to IN cord-276598-tm0yj2sn 101 9 P p NN cord-276598-tm0yj2sn 101 10 - - : cord-276598-tm0yj2sn 101 11 Ns Ns NNP cord-276598-tm0yj2sn 101 12 can can MD cord-276598-tm0yj2sn 101 13 be be VB cord-276598-tm0yj2sn 101 14 separated separate VBN cord-276598-tm0yj2sn 101 15 into into IN cord-276598-tm0yj2sn 101 16 six six CD cord-276598-tm0yj2sn 101 17 categories category NNS cord-276598-tm0yj2sn 101 18 : : : cord-276598-tm0yj2sn 101 19 salt salt NN cord-276598-tm0yj2sn 101 20 elimination elimination NN cord-276598-tm0yj2sn 101 21 , , , cord-276598-tm0yj2sn 101 22 oxidative oxidative JJ cord-276598-tm0yj2sn 101 23 cross cross NN cord-276598-tm0yj2sn 101 24 - - NN cord-276598-tm0yj2sn 101 25 coupling coupling JJ cord-276598-tm0yj2sn 101 26 , , , cord-276598-tm0yj2sn 101 27 azide azide NN cord-276598-tm0yj2sn 101 28 , , , cord-276598-tm0yj2sn 101 29 reduction reduction NN cord-276598-tm0yj2sn 101 30 , , , cord-276598-tm0yj2sn 101 31 hydrophosphinylation hydrophosphinylation NN cord-276598-tm0yj2sn 101 32 , , , cord-276598-tm0yj2sn 101 33 and and CC cord-276598-tm0yj2sn 101 34 phosphoramidate phosphoramidate NN cord-276598-tm0yj2sn 101 35 - - HYPH cord-276598-tm0yj2sn 101 36 aldehyde aldehyde NN cord-276598-tm0yj2sn 101 37 - - HYPH cord-276598-tm0yj2sn 101 38 dienophile dienophile NN cord-276598-tm0yj2sn 101 39 ( ( -LRB- cord-276598-tm0yj2sn 101 40 PAD pad NN cord-276598-tm0yj2sn 101 41 ) ) -RRB- cord-276598-tm0yj2sn 101 42 . . . cord-276598-tm0yj2sn 102 1 Each each DT cord-276598-tm0yj2sn 102 2 of of IN cord-276598-tm0yj2sn 102 3 the the DT cord-276598-tm0yj2sn 102 4 categories category NNS cord-276598-tm0yj2sn 102 5 will will MD cord-276598-tm0yj2sn 102 6 be be VB cord-276598-tm0yj2sn 102 7 discussed discuss VBN cord-276598-tm0yj2sn 102 8 in in IN cord-276598-tm0yj2sn 102 9 detail detail NN cord-276598-tm0yj2sn 102 10 in in IN cord-276598-tm0yj2sn 102 11 the the DT cord-276598-tm0yj2sn 102 12 coming come VBG cord-276598-tm0yj2sn 102 13 sections section NNS cord-276598-tm0yj2sn 102 14 , , , cord-276598-tm0yj2sn 102 15 with with IN cord-276598-tm0yj2sn 102 16 an an DT cord-276598-tm0yj2sn 102 17 emphasis emphasis NN cord-276598-tm0yj2sn 102 18 on on IN cord-276598-tm0yj2sn 102 19 conditions condition NNS cord-276598-tm0yj2sn 102 20 , , , cord-276598-tm0yj2sn 102 21 scope scope NN cord-276598-tm0yj2sn 102 22 , , , cord-276598-tm0yj2sn 102 23 and and CC cord-276598-tm0yj2sn 102 24 mechanism mechanism NN cord-276598-tm0yj2sn 102 25 . . . cord-276598-tm0yj2sn 103 1 This this DT cord-276598-tm0yj2sn 103 2 discussion discussion NN cord-276598-tm0yj2sn 103 3 will will MD cord-276598-tm0yj2sn 103 4 be be VB cord-276598-tm0yj2sn 103 5 preceded precede VBN cord-276598-tm0yj2sn 103 6 by by IN cord-276598-tm0yj2sn 103 7 a a DT cord-276598-tm0yj2sn 103 8 brief brief JJ cord-276598-tm0yj2sn 103 9 introduction introduction NN cord-276598-tm0yj2sn 103 10 to to IN cord-276598-tm0yj2sn 103 11 the the DT cord-276598-tm0yj2sn 103 12 early early JJ cord-276598-tm0yj2sn 103 13 synthetic synthetic JJ cord-276598-tm0yj2sn 103 14 routes route NNS cord-276598-tm0yj2sn 103 15 . . . cord-276598-tm0yj2sn 104 1 Based base VBN cord-276598-tm0yj2sn 104 2 on on IN cord-276598-tm0yj2sn 104 3 the the DT cord-276598-tm0yj2sn 104 4 available available JJ cord-276598-tm0yj2sn 104 5 literature literature NN cord-276598-tm0yj2sn 104 6 , , , cord-276598-tm0yj2sn 104 7 one one CD cord-276598-tm0yj2sn 104 8 of of IN cord-276598-tm0yj2sn 104 9 the the DT cord-276598-tm0yj2sn 104 10 earliest early JJS cord-276598-tm0yj2sn 104 11 syntheses synthesis NNS cord-276598-tm0yj2sn 104 12 of of IN cord-276598-tm0yj2sn 104 13 P P NNP cord-276598-tm0yj2sn 104 14 - - HYPH cord-276598-tm0yj2sn 104 15 Ns Ns NNP cord-276598-tm0yj2sn 104 16 involved involve VBD cord-276598-tm0yj2sn 104 17 the the DT cord-276598-tm0yj2sn 104 18 works work NNS cord-276598-tm0yj2sn 104 19 of of IN cord-276598-tm0yj2sn 104 20 Audrieth Audrieth NNP cord-276598-tm0yj2sn 104 21 and and CC cord-276598-tm0yj2sn 104 22 Toy Toy NNP cord-276598-tm0yj2sn 104 23 [ [ -LRB- cord-276598-tm0yj2sn 104 24 76 76 CD cord-276598-tm0yj2sn 104 25 , , , cord-276598-tm0yj2sn 104 26 77 77 CD cord-276598-tm0yj2sn 104 27 ] ] -RRB- cord-276598-tm0yj2sn 104 28 . . . cord-276598-tm0yj2sn 105 1 Audrieth Audrieth NNP cord-276598-tm0yj2sn 105 2 and and CC cord-276598-tm0yj2sn 105 3 Toy Toy NNP cord-276598-tm0yj2sn 105 4 treated treat VBD cord-276598-tm0yj2sn 105 5 phosphoryl phosphoryl NNS cord-276598-tm0yj2sn 105 6 trichloride trichloride VBN cord-276598-tm0yj2sn 105 7 with with IN cord-276598-tm0yj2sn 105 8 phenol phenol NN cord-276598-tm0yj2sn 105 9 in in IN cord-276598-tm0yj2sn 105 10 the the DT cord-276598-tm0yj2sn 105 11 presence presence NN cord-276598-tm0yj2sn 105 12 of of IN cord-276598-tm0yj2sn 105 13 pyridine pyridine NN cord-276598-tm0yj2sn 105 14 to to TO cord-276598-tm0yj2sn 105 15 obtain obtain VB cord-276598-tm0yj2sn 105 16 a a DT cord-276598-tm0yj2sn 105 17 mixture mixture NN cord-276598-tm0yj2sn 105 18 of of IN cord-276598-tm0yj2sn 105 19 diphenylchlorophosphate diphenylchlorophosphate NNP cord-276598-tm0yj2sn 105 20 ( ( -LRB- cord-276598-tm0yj2sn 105 21 dPCP dpcp JJ cord-276598-tm0yj2sn 105 22 ) ) -RRB- cord-276598-tm0yj2sn 105 23 and and CC cord-276598-tm0yj2sn 105 24 phenyl phenyl NN cord-276598-tm0yj2sn 105 25 dichlorophosphate dichlorophosphate VBP cord-276598-tm0yj2sn 105 26 ( ( -LRB- cord-276598-tm0yj2sn 105 27 PdCP PdCP NNP cord-276598-tm0yj2sn 105 28 ) ) -RRB- cord-276598-tm0yj2sn 105 29 . . . cord-276598-tm0yj2sn 106 1 Upon upon IN cord-276598-tm0yj2sn 106 2 reacting react VBG cord-276598-tm0yj2sn 106 3 the the DT cord-276598-tm0yj2sn 106 4 mixture mixture NN cord-276598-tm0yj2sn 106 5 with with IN cord-276598-tm0yj2sn 106 6 gaseous gaseous JJ cord-276598-tm0yj2sn 106 7 or or CC cord-276598-tm0yj2sn 106 8 aqueous aqueous JJ cord-276598-tm0yj2sn 106 9 NH NH NNP cord-276598-tm0yj2sn 106 10 3 3 CD cord-276598-tm0yj2sn 106 11 in in IN cord-276598-tm0yj2sn 106 12 1941 1941 CD cord-276598-tm0yj2sn 106 13 or or CC cord-276598-tm0yj2sn 106 14 primary primary JJ cord-276598-tm0yj2sn 106 15 amine amine NN cord-276598-tm0yj2sn 106 16 in in IN cord-276598-tm0yj2sn 106 17 1942 1942 CD cord-276598-tm0yj2sn 106 18 , , , cord-276598-tm0yj2sn 106 19 P P NNP cord-276598-tm0yj2sn 106 20 - - HYPH cord-276598-tm0yj2sn 106 21 N N NNP cord-276598-tm0yj2sn 106 22 and and CC cord-276598-tm0yj2sn 106 23 N N NNP cord-276598-tm0yj2sn 106 24 - - HYPH cord-276598-tm0yj2sn 106 25 P P NNP cord-276598-tm0yj2sn 106 26 - - HYPH cord-276598-tm0yj2sn 106 27 N N NNP cord-276598-tm0yj2sn 106 28 were be VBD cord-276598-tm0yj2sn 106 29 formed form VBN cord-276598-tm0yj2sn 107 1 ( ( -LRB- cord-276598-tm0yj2sn 107 2 Scheme scheme NN cord-276598-tm0yj2sn 107 3 2 2 CD cord-276598-tm0yj2sn 107 4 route route NN cord-276598-tm0yj2sn 107 5 A a NN cord-276598-tm0yj2sn 107 6 , , , cord-276598-tm0yj2sn 107 7 R r NN cord-276598-tm0yj2sn 107 8 = = NN cord-276598-tm0yj2sn 107 9 Ph Ph NNP cord-276598-tm0yj2sn 107 10 ) ) -RRB- cord-276598-tm0yj2sn 107 11 . . . cord-276598-tm0yj2sn 108 1 In in IN cord-276598-tm0yj2sn 108 2 1945 1945 CD cord-276598-tm0yj2sn 108 3 , , , cord-276598-tm0yj2sn 108 4 P P NNP cord-276598-tm0yj2sn 108 5 - - HYPH cord-276598-tm0yj2sn 108 6 Ns Ns NNP cord-276598-tm0yj2sn 108 7 were be VBD cord-276598-tm0yj2sn 108 8 made make VBN cord-276598-tm0yj2sn 108 9 by by IN cord-276598-tm0yj2sn 108 10 Atherton Atherton NNP cord-276598-tm0yj2sn 108 11 , , , cord-276598-tm0yj2sn 108 12 Openshaw Openshaw NNP cord-276598-tm0yj2sn 108 13 , , , cord-276598-tm0yj2sn 108 14 and and CC cord-276598-tm0yj2sn 108 15 Todd Todd NNP cord-276598-tm0yj2sn 108 16 through through IN cord-276598-tm0yj2sn 108 17 a a DT cord-276598-tm0yj2sn 108 18 salt salt NN cord-276598-tm0yj2sn 108 19 elimination elimination NN cord-276598-tm0yj2sn 108 20 process process NN cord-276598-tm0yj2sn 108 21 using use VBG cord-276598-tm0yj2sn 108 22 disubstituted disubstitute VBN cord-276598-tm0yj2sn 108 23 H H NNP cord-276598-tm0yj2sn 108 24 - - HYPH cord-276598-tm0yj2sn 108 25 phosphonates phosphonates NNP cord-276598-tm0yj2sn 108 26 ( ( -LRB- cord-276598-tm0yj2sn 108 27 H h NN cord-276598-tm0yj2sn 108 28 - - HYPH cord-276598-tm0yj2sn 108 29 P P NNP cord-276598-tm0yj2sn 108 30 ) ) -RRB- cord-276598-tm0yj2sn 108 31 , , , cord-276598-tm0yj2sn 108 32 amines amine NNS cord-276598-tm0yj2sn 108 33 , , , cord-276598-tm0yj2sn 108 34 and and CC cord-276598-tm0yj2sn 108 35 chlorinating chlorinate VBG cord-276598-tm0yj2sn 108 36 agents agent NNS cord-276598-tm0yj2sn 108 37 ( ( -LRB- cord-276598-tm0yj2sn 108 38 Scheme scheme NN cord-276598-tm0yj2sn 108 39 2 2 CD cord-276598-tm0yj2sn 108 40 route route NN cord-276598-tm0yj2sn 108 41 B b NN cord-276598-tm0yj2sn 108 42 ) ) -RRB- cord-276598-tm0yj2sn 108 43 [ [ -LRB- cord-276598-tm0yj2sn 108 44 78 78 CD cord-276598-tm0yj2sn 108 45 ] ] -RRB- cord-276598-tm0yj2sn 108 46 . . . cord-276598-tm0yj2sn 109 1 Subsequently subsequently RB cord-276598-tm0yj2sn 109 2 , , , cord-276598-tm0yj2sn 109 3 the the DT cord-276598-tm0yj2sn 109 4 Atherton Atherton NNP cord-276598-tm0yj2sn 109 5 - - HYPH cord-276598-tm0yj2sn 109 6 Todd Todd NNP cord-276598-tm0yj2sn 109 7 group group NN cord-276598-tm0yj2sn 109 8 synthesized synthesize VBD cord-276598-tm0yj2sn 109 9 P P NNP cord-276598-tm0yj2sn 109 10 - - HYPH cord-276598-tm0yj2sn 109 11 Ns Ns NNP cord-276598-tm0yj2sn 109 12 via via IN cord-276598-tm0yj2sn 109 13 the the DT cord-276598-tm0yj2sn 109 14 same same JJ cord-276598-tm0yj2sn 109 15 method method NN cord-276598-tm0yj2sn 109 16 using use VBG cord-276598-tm0yj2sn 109 17 different different JJ cord-276598-tm0yj2sn 109 18 polyhalogen polyhalogen NN cord-276598-tm0yj2sn 109 19 solvents solvent NNS cord-276598-tm0yj2sn 109 20 in in IN cord-276598-tm0yj2sn 109 21 1947 1947 CD cord-276598-tm0yj2sn 109 22 [ [ -LRB- cord-276598-tm0yj2sn 109 23 79 79 CD cord-276598-tm0yj2sn 109 24 ] ] -RRB- cord-276598-tm0yj2sn 109 25 and and CC cord-276598-tm0yj2sn 109 26 using use VBG cord-276598-tm0yj2sn 109 27 alternative alternative JJ cord-276598-tm0yj2sn 109 28 phosphorylating phosphorylate VBG cord-276598-tm0yj2sn 109 29 agents agent NNS cord-276598-tm0yj2sn 109 30 in in IN cord-276598-tm0yj2sn 109 31 1948 1948 CD cord-276598-tm0yj2sn 109 32 [ [ -LRB- cord-276598-tm0yj2sn 109 33 80 80 CD cord-276598-tm0yj2sn 109 34 ] ] -RRB- cord-276598-tm0yj2sn 109 35 . . . cord-276598-tm0yj2sn 110 1 In in IN cord-276598-tm0yj2sn 110 2 1951 1951 CD cord-276598-tm0yj2sn 110 3 , , , cord-276598-tm0yj2sn 110 4 Wagner Wagner NNP cord-276598-tm0yj2sn 110 5 - - HYPH cord-276598-tm0yj2sn 110 6 Jauregg Jauregg NNP cord-276598-tm0yj2sn 110 7 et et FW cord-276598-tm0yj2sn 110 8 al al NNP cord-276598-tm0yj2sn 110 9 . . . cord-276598-tm0yj2sn 111 1 synthesized synthesize VBN cord-276598-tm0yj2sn 111 2 P P NNP cord-276598-tm0yj2sn 111 3 - - HYPH cord-276598-tm0yj2sn 111 4 N N NNP cord-276598-tm0yj2sn 111 5 compounds compound NNS cord-276598-tm0yj2sn 111 6 from from IN cord-276598-tm0yj2sn 111 7 diisopropylchlorophosphate diisopropylchlorophosphate NNP cord-276598-tm0yj2sn 111 8 ( ( -LRB- cord-276598-tm0yj2sn 111 9 dPrCP dPrCP NNP cord-276598-tm0yj2sn 111 10 ) ) -RRB- cord-276598-tm0yj2sn 111 11 or or CC cord-276598-tm0yj2sn 111 12 tetraethylpyrophosphate tetraethylpyrophosphate NN cord-276598-tm0yj2sn 111 13 ( ( -LRB- cord-276598-tm0yj2sn 111 14 tEPyP tEPyP NNP cord-276598-tm0yj2sn 111 15 ) ) -RRB- cord-276598-tm0yj2sn 111 16 and and CC cord-276598-tm0yj2sn 111 17 amines amine NNS cord-276598-tm0yj2sn 111 18 ( ( -LRB- cord-276598-tm0yj2sn 111 19 Scheme scheme NN cord-276598-tm0yj2sn 111 20 2 2 CD cord-276598-tm0yj2sn 111 21 route route NN cord-276598-tm0yj2sn 111 22 A a NN cord-276598-tm0yj2sn 111 23 , , , cord-276598-tm0yj2sn 111 24 R r NN cord-276598-tm0yj2sn 111 25 = = NN cord-276598-tm0yj2sn 111 26 i i NN cord-276598-tm0yj2sn 111 27 - - HYPH cord-276598-tm0yj2sn 111 28 Pr pr NN cord-276598-tm0yj2sn 111 29 and and CC cord-276598-tm0yj2sn 111 30 route route NN cord-276598-tm0yj2sn 111 31 C C NNP cord-276598-tm0yj2sn 111 32 , , , cord-276598-tm0yj2sn 111 33 respectively respectively RB cord-276598-tm0yj2sn 111 34 ) ) -RRB- cord-276598-tm0yj2sn 111 35 [ [ -LRB- cord-276598-tm0yj2sn 111 36 81 81 CD cord-276598-tm0yj2sn 111 37 ] ] -RRB- cord-276598-tm0yj2sn 111 38 . . . cord-276598-tm0yj2sn 112 1 Sodium sodium NN cord-276598-tm0yj2sn 112 2 anilide anilide NN cord-276598-tm0yj2sn 112 3 or or CC cord-276598-tm0yj2sn 112 4 sodium sodium NN cord-276598-tm0yj2sn 112 5 diphenylamide diphenylamide NNP cord-276598-tm0yj2sn 112 6 was be VBD cord-276598-tm0yj2sn 112 7 refluxed refluxe VBN cord-276598-tm0yj2sn 112 8 with with IN cord-276598-tm0yj2sn 112 9 triphenylphosphate triphenylphosphate NNP cord-276598-tm0yj2sn 112 10 ( ( -LRB- cord-276598-tm0yj2sn 112 11 tPPO tPPO NNP cord-276598-tm0yj2sn 112 12 ) ) -RRB- cord-276598-tm0yj2sn 112 13 to to TO cord-276598-tm0yj2sn 112 14 eliminate eliminate VB cord-276598-tm0yj2sn 112 15 phenol phenol NN cord-276598-tm0yj2sn 112 16 and and CC cord-276598-tm0yj2sn 112 17 give give VB cord-276598-tm0yj2sn 112 18 diphenyl diphenyl NNP cord-276598-tm0yj2sn 112 19 N N NNP cord-276598-tm0yj2sn 112 20 - - HYPH cord-276598-tm0yj2sn 112 21 phenylphosphoramidate phenylphosphoramidate NNP cord-276598-tm0yj2sn 112 22 or or CC cord-276598-tm0yj2sn 112 23 diphenyl diphenyl NNP cord-276598-tm0yj2sn 112 24 N N NNP cord-276598-tm0yj2sn 112 25 , , , cord-276598-tm0yj2sn 112 26 N N NNP cord-276598-tm0yj2sn 112 27 - - HYPH cord-276598-tm0yj2sn 112 28 diphenylphosphoramidate diphenylphosphoramidate NNP cord-276598-tm0yj2sn 112 29 in in IN cord-276598-tm0yj2sn 112 30 1964 1964 CD cord-276598-tm0yj2sn 112 31 ( ( -LRB- cord-276598-tm0yj2sn 112 32 Scheme scheme NN cord-276598-tm0yj2sn 112 33 2 2 CD cord-276598-tm0yj2sn 112 34 route route NN cord-276598-tm0yj2sn 112 35 D d NN cord-276598-tm0yj2sn 112 36 ) ) -RRB- cord-276598-tm0yj2sn 113 1 [ [ -LRB- cord-276598-tm0yj2sn 113 2 82 82 CD cord-276598-tm0yj2sn 113 3 ] ] -RRB- cord-276598-tm0yj2sn 113 4 . . . cord-276598-tm0yj2sn 114 1 In in IN cord-276598-tm0yj2sn 114 2 1965 1965 CD cord-276598-tm0yj2sn 114 3 , , , cord-276598-tm0yj2sn 114 4 Sundberg Sundberg NNP cord-276598-tm0yj2sn 114 5 reacted react VBD cord-276598-tm0yj2sn 114 6 1-ethyl-2-nitrobenzene 1-ethyl-2-nitrobenzene CD cord-276598-tm0yj2sn 114 7 and and CC cord-276598-tm0yj2sn 114 8 triethyl triethyl NNP cord-276598-tm0yj2sn 114 9 phosphite phosphite NNP cord-276598-tm0yj2sn 114 10 to to TO cord-276598-tm0yj2sn 114 11 obtain obtain VB cord-276598-tm0yj2sn 114 12 a a DT cord-276598-tm0yj2sn 114 13 phosphorimidate phosphorimidate NN cord-276598-tm0yj2sn 114 14 - - HYPH cord-276598-tm0yj2sn 114 15 product product NN cord-276598-tm0yj2sn 114 16 ( ( -LRB- cord-276598-tm0yj2sn 114 17 N n NN cord-276598-tm0yj2sn 114 18 = = NN cord-276598-tm0yj2sn 114 19 P p NN cord-276598-tm0yj2sn 114 20 ) ) -RRB- cord-276598-tm0yj2sn 114 21 that that WDT cord-276598-tm0yj2sn 114 22 was be VBD cord-276598-tm0yj2sn 114 23 converted convert VBN cord-276598-tm0yj2sn 114 24 to to IN cord-276598-tm0yj2sn 114 25 P P NNP cord-276598-tm0yj2sn 114 26 - - HYPH cord-276598-tm0yj2sn 114 27 N N NNP cord-276598-tm0yj2sn 114 28 on on IN cord-276598-tm0yj2sn 114 29 silica silica NN cord-276598-tm0yj2sn 114 30 or or CC cord-276598-tm0yj2sn 114 31 alumina alumina NN cord-276598-tm0yj2sn 114 32 columns column NNS cord-276598-tm0yj2sn 114 33 [ [ -LRB- cord-276598-tm0yj2sn 114 34 83 83 CD cord-276598-tm0yj2sn 114 35 ] ] -RRB- cord-276598-tm0yj2sn 114 36 . . . cord-276598-tm0yj2sn 115 1 Cadogan Cadogan NNP cord-276598-tm0yj2sn 115 2 and and CC cord-276598-tm0yj2sn 115 3 coworkers coworker NNS cord-276598-tm0yj2sn 115 4 reportedly reportedly RB cord-276598-tm0yj2sn 115 5 synthesized synthesize VBD cord-276598-tm0yj2sn 115 6 and and CC cord-276598-tm0yj2sn 115 7 investigated investigate VBD cord-276598-tm0yj2sn 115 8 the the DT cord-276598-tm0yj2sn 115 9 nucleophilicity nucleophilicity NN cord-276598-tm0yj2sn 115 10 of of IN cord-276598-tm0yj2sn 115 11 various various JJ cord-276598-tm0yj2sn 115 12 P p NN cord-276598-tm0yj2sn 115 13 - - HYPH cord-276598-tm0yj2sn 115 14 Ns Ns NNP cord-276598-tm0yj2sn 115 15 in in IN cord-276598-tm0yj2sn 115 16 1967 1967 CD cord-276598-tm0yj2sn 115 17 [ [ -LRB- cord-276598-tm0yj2sn 115 18 84 84 CD cord-276598-tm0yj2sn 115 19 ] ] -RRB- cord-276598-tm0yj2sn 115 20 . . . cord-276598-tm0yj2sn 116 1 Two two CD cord-276598-tm0yj2sn 116 2 years year NNS cord-276598-tm0yj2sn 116 3 later later RB cord-276598-tm0yj2sn 116 4 , , , cord-276598-tm0yj2sn 116 5 a a DT cord-276598-tm0yj2sn 116 6 mixture mixture NN cord-276598-tm0yj2sn 116 7 of of IN cord-276598-tm0yj2sn 116 8 N n NN cord-276598-tm0yj2sn 116 9 - - HYPH cord-276598-tm0yj2sn 116 10 arylphosphoramidates arylphosphoramidates NNP cord-276598-tm0yj2sn 116 11 , , , cord-276598-tm0yj2sn 116 12 dialkyl dialkyl NNP cord-276598-tm0yj2sn 116 13 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 116 14 , , , cord-276598-tm0yj2sn 116 15 and and CC cord-276598-tm0yj2sn 116 16 phosphonates phosphonate NNS cord-276598-tm0yj2sn 116 17 were be VBD cord-276598-tm0yj2sn 116 18 obtained obtain VBN cord-276598-tm0yj2sn 116 19 when when WRB cord-276598-tm0yj2sn 116 20 nitrosoand nitrosoand NNP cord-276598-tm0yj2sn 116 21 nitro nitro NN cord-276598-tm0yj2sn 116 22 - - HYPH cord-276598-tm0yj2sn 116 23 compounds compound NNS cord-276598-tm0yj2sn 116 24 were be VBD cord-276598-tm0yj2sn 116 25 reduced reduce VBN cord-276598-tm0yj2sn 116 26 in in IN cord-276598-tm0yj2sn 116 27 the the DT cord-276598-tm0yj2sn 116 28 presence presence NN cord-276598-tm0yj2sn 116 29 of of IN cord-276598-tm0yj2sn 116 30 ( ( -LRB- cord-276598-tm0yj2sn 116 31 RO ro NN cord-276598-tm0yj2sn 116 32 ) ) -RRB- cord-276598-tm0yj2sn 116 33 3 3 CD cord-276598-tm0yj2sn 116 34 P p NN cord-276598-tm0yj2sn 116 35 ( ( -LRB- cord-276598-tm0yj2sn 116 36 R r NN cord-276598-tm0yj2sn 116 37 = = NN cord-276598-tm0yj2sn 116 38 alkyl alkyl NN cord-276598-tm0yj2sn 116 39 ) ) -RRB- cord-276598-tm0yj2sn 117 1 [ [ -LRB- cord-276598-tm0yj2sn 117 2 85 85 CD cord-276598-tm0yj2sn 117 3 ] ] -RRB- cord-276598-tm0yj2sn 117 4 . . . cord-276598-tm0yj2sn 118 1 In in IN cord-276598-tm0yj2sn 118 2 1975 1975 CD cord-276598-tm0yj2sn 118 3 , , , cord-276598-tm0yj2sn 118 4 Appel Appel NNP cord-276598-tm0yj2sn 118 5 and and CC cord-276598-tm0yj2sn 118 6 Einig Einig NNP cord-276598-tm0yj2sn 118 7 [ [ -LRB- cord-276598-tm0yj2sn 118 8 86 86 CD cord-276598-tm0yj2sn 118 9 ] ] -RRB- cord-276598-tm0yj2sn 118 10 reported report VBD cord-276598-tm0yj2sn 118 11 a a DT cord-276598-tm0yj2sn 118 12 new new JJ cord-276598-tm0yj2sn 118 13 synthesis synthesis NN cord-276598-tm0yj2sn 118 14 to to IN cord-276598-tm0yj2sn 118 15 P p NN cord-276598-tm0yj2sn 118 16 - - HYPH cord-276598-tm0yj2sn 118 17 Ns Ns NNP cord-276598-tm0yj2sn 118 18 by by IN cord-276598-tm0yj2sn 118 19 reacting react VBG cord-276598-tm0yj2sn 118 20 phosphoric phosphoric JJ cord-276598-tm0yj2sn 118 21 acid acid NN cord-276598-tm0yj2sn 118 22 and and CC cord-276598-tm0yj2sn 118 23 an an DT cord-276598-tm0yj2sn 118 24 amine amine NN cord-276598-tm0yj2sn 118 25 in in IN cord-276598-tm0yj2sn 118 26 the the DT cord-276598-tm0yj2sn 118 27 presence presence NN cord-276598-tm0yj2sn 118 28 of of IN cord-276598-tm0yj2sn 118 29 triphenylphosphine triphenylphosphine NNP cord-276598-tm0yj2sn 118 30 ( ( -LRB- cord-276598-tm0yj2sn 118 31 tPP tPP NNP cord-276598-tm0yj2sn 118 32 ) ) -RRB- cord-276598-tm0yj2sn 118 33 and and CC cord-276598-tm0yj2sn 118 34 CCl CCl NNS cord-276598-tm0yj2sn 118 35 4 4 CD cord-276598-tm0yj2sn 118 36 . . . cord-276598-tm0yj2sn 119 1 The the DT cord-276598-tm0yj2sn 119 2 same same JJ cord-276598-tm0yj2sn 119 3 year year NN cord-276598-tm0yj2sn 119 4 , , , cord-276598-tm0yj2sn 119 5 phase phase NN cord-276598-tm0yj2sn 119 6 - - HYPH cord-276598-tm0yj2sn 119 7 transfer transfer NN cord-276598-tm0yj2sn 119 8 catalysis catalysis NN cord-276598-tm0yj2sn 119 9 was be VBD cord-276598-tm0yj2sn 119 10 introduced introduce VBN cord-276598-tm0yj2sn 119 11 by by IN cord-276598-tm0yj2sn 119 12 Zwierzak Zwierzak NNP cord-276598-tm0yj2sn 119 13 to to TO cord-276598-tm0yj2sn 119 14 synthesize synthesize VB cord-276598-tm0yj2sn 119 15 P p NN cord-276598-tm0yj2sn 119 16 - - HYPH cord-276598-tm0yj2sn 119 17 Ns ns NN cord-276598-tm0yj2sn 119 18 through through IN cord-276598-tm0yj2sn 119 19 the the DT cord-276598-tm0yj2sn 119 20 phosphorylation phosphorylation NN cord-276598-tm0yj2sn 119 21 of of IN cord-276598-tm0yj2sn 119 22 amines amine NNS cord-276598-tm0yj2sn 119 23 [ [ -LRB- cord-276598-tm0yj2sn 119 24 87 87 CD cord-276598-tm0yj2sn 119 25 ] ] -RRB- cord-276598-tm0yj2sn 119 26 . . . cord-276598-tm0yj2sn 120 1 The the DT cord-276598-tm0yj2sn 120 2 selective selective JJ cord-276598-tm0yj2sn 120 3 alkylation alkylation NN cord-276598-tm0yj2sn 120 4 of of IN cord-276598-tm0yj2sn 120 5 ( ( -LRB- cord-276598-tm0yj2sn 120 6 EtO EtO NNP cord-276598-tm0yj2sn 120 7 ) ) -RRB- cord-276598-tm0yj2sn 120 8 2 2 CD cord-276598-tm0yj2sn 120 9 P(O)NH P(O)NH NNP cord-276598-tm0yj2sn 120 10 2 2 CD cord-276598-tm0yj2sn 120 11 via via IN cord-276598-tm0yj2sn 120 12 silylation silylation NN cord-276598-tm0yj2sn 120 13 was be VBD cord-276598-tm0yj2sn 120 14 achieved achieve VBN cord-276598-tm0yj2sn 120 15 by by IN cord-276598-tm0yj2sn 120 16 Zwierzak Zwierzak NNP cord-276598-tm0yj2sn 120 17 in in IN cord-276598-tm0yj2sn 120 18 1982 1982 CD cord-276598-tm0yj2sn 120 19 using use VBG cord-276598-tm0yj2sn 120 20 [ [ -LRB- cord-276598-tm0yj2sn 120 21 n n NNP cord-276598-tm0yj2sn 120 22 - - HYPH cord-276598-tm0yj2sn 120 23 Bu Bu NNP cord-276598-tm0yj2sn 120 24 4 4 CD cord-276598-tm0yj2sn 120 25 N]Br N]Br NNP cord-276598-tm0yj2sn 120 26 catalyst catalyst NN cord-276598-tm0yj2sn 120 27 ( ( -LRB- cord-276598-tm0yj2sn 120 28 Scheme scheme NN cord-276598-tm0yj2sn 120 29 2 2 CD cord-276598-tm0yj2sn 120 30 route route NN cord-276598-tm0yj2sn 120 31 E e NN cord-276598-tm0yj2sn 120 32 ) ) -RRB- cord-276598-tm0yj2sn 121 1 [ [ -LRB- cord-276598-tm0yj2sn 121 2 88 88 CD cord-276598-tm0yj2sn 121 3 ] ] -RRB- cord-276598-tm0yj2sn 121 4 . . . cord-276598-tm0yj2sn 122 1 In in IN cord-276598-tm0yj2sn 122 2 1984 1984 CD cord-276598-tm0yj2sn 122 3 , , , cord-276598-tm0yj2sn 122 4 Zwierzak Zwierzak NNP cord-276598-tm0yj2sn 122 5 and and CC cord-276598-tm0yj2sn 122 6 Osowska Osowska NNP cord-276598-tm0yj2sn 122 7 - - HYPH cord-276598-tm0yj2sn 122 8 Pacewicka Pacewicka NNP cord-276598-tm0yj2sn 122 9 reported report VBD cord-276598-tm0yj2sn 122 10 the the DT cord-276598-tm0yj2sn 122 11 synthesis synthesis NN cord-276598-tm0yj2sn 122 12 of of IN cord-276598-tm0yj2sn 122 13 various various JJ cord-276598-tm0yj2sn 122 14 P p NN cord-276598-tm0yj2sn 122 15 - - HYPH cord-276598-tm0yj2sn 122 16 Ns Ns NNP cord-276598-tm0yj2sn 122 17 via via IN cord-276598-tm0yj2sn 122 18 inorganic inorganic JJ cord-276598-tm0yj2sn 122 19 salt salt NN cord-276598-tm0yj2sn 122 20 elimination elimination NN cord-276598-tm0yj2sn 122 21 [ [ -LRB- cord-276598-tm0yj2sn 122 22 89 89 CD cord-276598-tm0yj2sn 122 23 ] ] -RRB- cord-276598-tm0yj2sn 122 24 and and CC cord-276598-tm0yj2sn 122 25 the the DT cord-276598-tm0yj2sn 122 26 direct direct JJ cord-276598-tm0yj2sn 122 27 conversion conversion NN cord-276598-tm0yj2sn 122 28 of of IN cord-276598-tm0yj2sn 122 29 phosphoric phosphoric JJ cord-276598-tm0yj2sn 122 30 acid acid NN cord-276598-tm0yj2sn 122 31 [ [ -LRB- cord-276598-tm0yj2sn 122 32 90 90 CD cord-276598-tm0yj2sn 122 33 ] ] -RRB- cord-276598-tm0yj2sn 122 34 . . . cord-276598-tm0yj2sn 123 1 In in IN cord-276598-tm0yj2sn 123 2 1985 1985 CD cord-276598-tm0yj2sn 123 3 , , , cord-276598-tm0yj2sn 123 4 Riesel Riesel NNP cord-276598-tm0yj2sn 123 5 et et NNP cord-276598-tm0yj2sn 123 6 al al NNP cord-276598-tm0yj2sn 123 7 . . NNP cord-276598-tm0yj2sn 123 8 reacted react VBD cord-276598-tm0yj2sn 123 9 primary primary JJ cord-276598-tm0yj2sn 123 10 amines amine NNS cord-276598-tm0yj2sn 123 11 or or CC cord-276598-tm0yj2sn 123 12 NH NH NNP cord-276598-tm0yj2sn 123 13 3 3 CD cord-276598-tm0yj2sn 123 14 with with IN cord-276598-tm0yj2sn 123 15 ( ( -LRB- cord-276598-tm0yj2sn 123 16 RO ro NN cord-276598-tm0yj2sn 123 17 ) ) -RRB- cord-276598-tm0yj2sn 123 18 3 3 CD cord-276598-tm0yj2sn 123 19 P p NN cord-276598-tm0yj2sn 123 20 ( ( -LRB- cord-276598-tm0yj2sn 123 21 R r NN cord-276598-tm0yj2sn 123 22 = = NN cord-276598-tm0yj2sn 123 23 alkyl alkyl NN cord-276598-tm0yj2sn 123 24 ) ) -RRB- cord-276598-tm0yj2sn 123 25 and and CC cord-276598-tm0yj2sn 123 26 CCl CCl NNS cord-276598-tm0yj2sn 123 27 4 4 CD cord-276598-tm0yj2sn 123 28 as as IN cord-276598-tm0yj2sn 123 29 an an DT cord-276598-tm0yj2sn 123 30 effective effective JJ cord-276598-tm0yj2sn 123 31 route route NN cord-276598-tm0yj2sn 123 32 to to IN cord-276598-tm0yj2sn 123 33 P p NN cord-276598-tm0yj2sn 123 34 - - HYPH cord-276598-tm0yj2sn 123 35 Ns Ns NNP cord-276598-tm0yj2sn 123 36 [ [ -LRB- cord-276598-tm0yj2sn 123 37 91 91 CD cord-276598-tm0yj2sn 123 38 ] ] -RRB- cord-276598-tm0yj2sn 123 39 . . . cord-276598-tm0yj2sn 124 1 Nielsen Nielsen NNP cord-276598-tm0yj2sn 124 2 and and CC cord-276598-tm0yj2sn 124 3 Caruthers Caruthers NNP cord-276598-tm0yj2sn 124 4 reported report VBD cord-276598-tm0yj2sn 124 5 the the DT cord-276598-tm0yj2sn 124 6 first first JJ cord-276598-tm0yj2sn 124 7 iodine iodine NN cord-276598-tm0yj2sn 124 8 - - HYPH cord-276598-tm0yj2sn 124 9 mediated mediate VBN cord-276598-tm0yj2sn 124 10 reaction reaction NN cord-276598-tm0yj2sn 124 11 of of IN cord-276598-tm0yj2sn 124 12 phosphite phosphite NNP cord-276598-tm0yj2sn 124 13 and and CC cord-276598-tm0yj2sn 124 14 n n NNP cord-276598-tm0yj2sn 124 15 - - HYPH cord-276598-tm0yj2sn 124 16 butylamine butylamine NN cord-276598-tm0yj2sn 124 17 to to TO cord-276598-tm0yj2sn 124 18 synthesize synthesize VB cord-276598-tm0yj2sn 124 19 P p NN cord-276598-tm0yj2sn 124 20 - - HYPH cord-276598-tm0yj2sn 124 21 Ns Ns NNP cord-276598-tm0yj2sn 124 22 in in IN cord-276598-tm0yj2sn 124 23 1988 1988 CD cord-276598-tm0yj2sn 124 24 ( ( -LRB- cord-276598-tm0yj2sn 124 25 Scheme scheme NN cord-276598-tm0yj2sn 124 26 2 2 CD cord-276598-tm0yj2sn 124 27 route route NN cord-276598-tm0yj2sn 124 28 F F NNP cord-276598-tm0yj2sn 124 29 ) ) -RRB- cord-276598-tm0yj2sn 124 30 [ [ -LRB- cord-276598-tm0yj2sn 124 31 92 92 CD cord-276598-tm0yj2sn 124 32 ] ] -RRB- cord-276598-tm0yj2sn 124 33 . . . cord-276598-tm0yj2sn 125 1 At at IN cord-276598-tm0yj2sn 125 2 about about RB cord-276598-tm0yj2sn 125 3 the the DT cord-276598-tm0yj2sn 125 4 same same JJ cord-276598-tm0yj2sn 125 5 time time NN cord-276598-tm0yj2sn 125 6 , , , cord-276598-tm0yj2sn 125 7 P P NNP cord-276598-tm0yj2sn 125 8 - - HYPH cord-276598-tm0yj2sn 125 9 Ns Ns NNP cord-276598-tm0yj2sn 125 10 were be VBD cord-276598-tm0yj2sn 125 11 synthesized synthesize VBN cord-276598-tm0yj2sn 125 12 from from IN cord-276598-tm0yj2sn 125 13 a a DT cord-276598-tm0yj2sn 125 14 reaction reaction NN cord-276598-tm0yj2sn 125 15 of of IN cord-276598-tm0yj2sn 125 16 azide azide NN cord-276598-tm0yj2sn 125 17 and and CC cord-276598-tm0yj2sn 125 18 ( ( -LRB- cord-276598-tm0yj2sn 125 19 RO RO NNP cord-276598-tm0yj2sn 125 20 ) ) -RRB- cord-276598-tm0yj2sn 125 21 3 3 CD cord-276598-tm0yj2sn 125 22 P p NN cord-276598-tm0yj2sn 125 23 ( ( -LRB- cord-276598-tm0yj2sn 125 24 R r NN cord-276598-tm0yj2sn 125 25 = = NN cord-276598-tm0yj2sn 125 26 alkyl alkyl NN cord-276598-tm0yj2sn 125 27 ) ) -RRB- cord-276598-tm0yj2sn 125 28 in in IN cord-276598-tm0yj2sn 125 29 a a DT cord-276598-tm0yj2sn 125 30 one one CD cord-276598-tm0yj2sn 125 31 - - HYPH cord-276598-tm0yj2sn 125 32 pot pot NN cord-276598-tm0yj2sn 125 33 process process NN cord-276598-tm0yj2sn 125 34 [ [ -LRB- cord-276598-tm0yj2sn 125 35 93 93 CD cord-276598-tm0yj2sn 125 36 ] ] -RRB- cord-276598-tm0yj2sn 125 37 . . . cord-276598-tm0yj2sn 126 1 A a DT cord-276598-tm0yj2sn 126 2 magnesium magnesium NN cord-276598-tm0yj2sn 126 3 chloride chloride NN cord-276598-tm0yj2sn 126 4 - - HYPH cord-276598-tm0yj2sn 126 5 catalyzed catalyze VBN cord-276598-tm0yj2sn 126 6 reaction reaction NN cord-276598-tm0yj2sn 126 7 of of IN cord-276598-tm0yj2sn 126 8 2,6-dimethylphenol 2,6-dimethylphenol CD cord-276598-tm0yj2sn 126 9 and and CC cord-276598-tm0yj2sn 126 10 phosphorus phosphorus NN cord-276598-tm0yj2sn 126 11 oxychloride oxychloride NN cord-276598-tm0yj2sn 126 12 was be VBD cord-276598-tm0yj2sn 126 13 used use VBN cord-276598-tm0yj2sn 126 14 to to TO cord-276598-tm0yj2sn 126 15 generate generate VB cord-276598-tm0yj2sn 126 16 phosphorochloridate phosphorochloridate NN cord-276598-tm0yj2sn 126 17 , , , cord-276598-tm0yj2sn 126 18 which which WDT cord-276598-tm0yj2sn 126 19 was be VBD cord-276598-tm0yj2sn 126 20 used use VBN cord-276598-tm0yj2sn 126 21 for for IN cord-276598-tm0yj2sn 126 22 the the DT cord-276598-tm0yj2sn 126 23 phosphorylation phosphorylation NN cord-276598-tm0yj2sn 126 24 of of IN cord-276598-tm0yj2sn 126 25 amines amine NNS cord-276598-tm0yj2sn 126 26 to to TO cord-276598-tm0yj2sn 126 27 synthesize synthesize VB cord-276598-tm0yj2sn 126 28 P p NN cord-276598-tm0yj2sn 126 29 - - HYPH cord-276598-tm0yj2sn 126 30 Ns Ns NNP cord-276598-tm0yj2sn 126 31 [ [ -LRB- cord-276598-tm0yj2sn 126 32 94 94 CD cord-276598-tm0yj2sn 126 33 ] ] -RRB- cord-276598-tm0yj2sn 126 34 . . . cord-276598-tm0yj2sn 127 1 The the DT cord-276598-tm0yj2sn 127 2 aforementioned aforementioned JJ cord-276598-tm0yj2sn 127 3 syntheses synthesis NNS cord-276598-tm0yj2sn 127 4 demonstrate demonstrate VBP cord-276598-tm0yj2sn 127 5 the the DT cord-276598-tm0yj2sn 127 6 diversity diversity NN cord-276598-tm0yj2sn 127 7 of of IN cord-276598-tm0yj2sn 127 8 organophosphorus organophosphorus JJ cord-276598-tm0yj2sn 127 9 synthons synthon NNS cord-276598-tm0yj2sn 127 10 available available JJ cord-276598-tm0yj2sn 127 11 for for IN cord-276598-tm0yj2sn 127 12 P p NN cord-276598-tm0yj2sn 127 13 - - HYPH cord-276598-tm0yj2sn 127 14 N n CD cord-276598-tm0yj2sn 127 15 chemistry chemistry NN cord-276598-tm0yj2sn 127 16 up up IN cord-276598-tm0yj2sn 127 17 until until IN cord-276598-tm0yj2sn 127 18 1988 1988 CD cord-276598-tm0yj2sn 127 19 and and CC cord-276598-tm0yj2sn 127 20 highlight highlight VB cord-276598-tm0yj2sn 127 21 the the DT cord-276598-tm0yj2sn 127 22 main main JJ cord-276598-tm0yj2sn 127 23 pioneers pioneer NNS cord-276598-tm0yj2sn 127 24 in in IN cord-276598-tm0yj2sn 127 25 the the DT cord-276598-tm0yj2sn 127 26 field field NN cord-276598-tm0yj2sn 127 27 ( ( -LRB- cord-276598-tm0yj2sn 127 28 Figure figure NN cord-276598-tm0yj2sn 127 29 4 4 CD cord-276598-tm0yj2sn 127 30 ) ) -RRB- cord-276598-tm0yj2sn 127 31 . . . cord-276598-tm0yj2sn 128 1 The the DT cord-276598-tm0yj2sn 128 2 research research NN cord-276598-tm0yj2sn 128 3 in in IN cord-276598-tm0yj2sn 128 4 these these DT cord-276598-tm0yj2sn 128 5 initial initial JJ cord-276598-tm0yj2sn 128 6 studies study NNS cord-276598-tm0yj2sn 128 7 has have VBZ cord-276598-tm0yj2sn 128 8 focused focus VBN cord-276598-tm0yj2sn 128 9 on on IN cord-276598-tm0yj2sn 128 10 reducing reduce VBG cord-276598-tm0yj2sn 128 11 waste waste NN cord-276598-tm0yj2sn 128 12 , , , cord-276598-tm0yj2sn 128 13 limiting limit VBG cord-276598-tm0yj2sn 128 14 toxic toxic JJ cord-276598-tm0yj2sn 128 15 reagents reagent NNS cord-276598-tm0yj2sn 128 16 , , , cord-276598-tm0yj2sn 128 17 improving improve VBG cord-276598-tm0yj2sn 128 18 selectivity selectivity NN cord-276598-tm0yj2sn 128 19 , , , cord-276598-tm0yj2sn 128 20 expanding expand VBG cord-276598-tm0yj2sn 128 21 scope scope NN cord-276598-tm0yj2sn 128 22 , , , cord-276598-tm0yj2sn 128 23 and and CC cord-276598-tm0yj2sn 128 24 searching search VBG cord-276598-tm0yj2sn 128 25 for for IN cord-276598-tm0yj2sn 128 26 effective effective JJ cord-276598-tm0yj2sn 128 27 and and CC cord-276598-tm0yj2sn 128 28 efficient efficient JJ cord-276598-tm0yj2sn 128 29 catalytic catalytic JJ cord-276598-tm0yj2sn 128 30 P p NN cord-276598-tm0yj2sn 128 31 - - HYPH cord-276598-tm0yj2sn 128 32 N n CD cord-276598-tm0yj2sn 128 33 bond bond NN cord-276598-tm0yj2sn 128 34 - - HYPH cord-276598-tm0yj2sn 128 35 making make VBG cord-276598-tm0yj2sn 128 36 solutions solution NNS cord-276598-tm0yj2sn 128 37 . . . cord-276598-tm0yj2sn 129 1 The the DT cord-276598-tm0yj2sn 129 2 aforementioned aforementioned JJ cord-276598-tm0yj2sn 129 3 syntheses synthesis NNS cord-276598-tm0yj2sn 129 4 demonstrate demonstrate VBP cord-276598-tm0yj2sn 129 5 the the DT cord-276598-tm0yj2sn 129 6 diversity diversity NN cord-276598-tm0yj2sn 129 7 of of IN cord-276598-tm0yj2sn 129 8 organophosphorus organophosphorus JJ cord-276598-tm0yj2sn 129 9 synthons synthon NNS cord-276598-tm0yj2sn 129 10 available available JJ cord-276598-tm0yj2sn 129 11 for for IN cord-276598-tm0yj2sn 129 12 P p NN cord-276598-tm0yj2sn 129 13 - - HYPH cord-276598-tm0yj2sn 129 14 N n CD cord-276598-tm0yj2sn 129 15 chemistry chemistry NN cord-276598-tm0yj2sn 129 16 up up IN cord-276598-tm0yj2sn 129 17 until until IN cord-276598-tm0yj2sn 129 18 1988 1988 CD cord-276598-tm0yj2sn 129 19 and and CC cord-276598-tm0yj2sn 129 20 highlight highlight VB cord-276598-tm0yj2sn 129 21 the the DT cord-276598-tm0yj2sn 129 22 main main JJ cord-276598-tm0yj2sn 129 23 pioneers pioneer NNS cord-276598-tm0yj2sn 129 24 in in IN cord-276598-tm0yj2sn 129 25 the the DT cord-276598-tm0yj2sn 129 26 field field NN cord-276598-tm0yj2sn 129 27 ( ( -LRB- cord-276598-tm0yj2sn 129 28 Figure figure NN cord-276598-tm0yj2sn 129 29 4 4 CD cord-276598-tm0yj2sn 129 30 ) ) -RRB- cord-276598-tm0yj2sn 129 31 . . . cord-276598-tm0yj2sn 130 1 The the DT cord-276598-tm0yj2sn 130 2 research research NN cord-276598-tm0yj2sn 130 3 in in IN cord-276598-tm0yj2sn 130 4 these these DT cord-276598-tm0yj2sn 130 5 initial initial JJ cord-276598-tm0yj2sn 130 6 studies study NNS cord-276598-tm0yj2sn 130 7 has have VBZ cord-276598-tm0yj2sn 130 8 focused focus VBN cord-276598-tm0yj2sn 130 9 on on IN cord-276598-tm0yj2sn 130 10 reducing reduce VBG cord-276598-tm0yj2sn 130 11 waste waste NN cord-276598-tm0yj2sn 130 12 , , , cord-276598-tm0yj2sn 130 13 limiting limit VBG cord-276598-tm0yj2sn 130 14 toxic toxic JJ cord-276598-tm0yj2sn 130 15 reagents reagent NNS cord-276598-tm0yj2sn 130 16 , , , cord-276598-tm0yj2sn 130 17 improving improve VBG cord-276598-tm0yj2sn 130 18 selectivity selectivity NN cord-276598-tm0yj2sn 130 19 , , , cord-276598-tm0yj2sn 130 20 expanding expand VBG cord-276598-tm0yj2sn 130 21 scope scope NN cord-276598-tm0yj2sn 130 22 , , , cord-276598-tm0yj2sn 130 23 and and CC cord-276598-tm0yj2sn 130 24 searching search VBG cord-276598-tm0yj2sn 130 25 for for IN cord-276598-tm0yj2sn 130 26 effective effective JJ cord-276598-tm0yj2sn 130 27 and and CC cord-276598-tm0yj2sn 130 28 efficient efficient JJ cord-276598-tm0yj2sn 130 29 catalytic catalytic JJ cord-276598-tm0yj2sn 130 30 P p NN cord-276598-tm0yj2sn 130 31 - - HYPH cord-276598-tm0yj2sn 130 32 N n CD cord-276598-tm0yj2sn 130 33 bond bond NN cord-276598-tm0yj2sn 130 34 - - HYPH cord-276598-tm0yj2sn 130 35 making make VBG cord-276598-tm0yj2sn 130 36 solutions solution NNS cord-276598-tm0yj2sn 130 37 . . . cord-276598-tm0yj2sn 131 1 The the DT cord-276598-tm0yj2sn 131 2 aforementioned aforementioned JJ cord-276598-tm0yj2sn 131 3 syntheses synthesis NNS cord-276598-tm0yj2sn 131 4 demonstrate demonstrate VBP cord-276598-tm0yj2sn 131 5 the the DT cord-276598-tm0yj2sn 131 6 diversity diversity NN cord-276598-tm0yj2sn 131 7 of of IN cord-276598-tm0yj2sn 131 8 organophosphorus organophosphorus JJ cord-276598-tm0yj2sn 131 9 synthons synthon NNS cord-276598-tm0yj2sn 131 10 available available JJ cord-276598-tm0yj2sn 131 11 for for IN cord-276598-tm0yj2sn 131 12 P p NN cord-276598-tm0yj2sn 131 13 - - HYPH cord-276598-tm0yj2sn 131 14 N n CD cord-276598-tm0yj2sn 131 15 chemistry chemistry NN cord-276598-tm0yj2sn 131 16 up up IN cord-276598-tm0yj2sn 131 17 until until IN cord-276598-tm0yj2sn 131 18 1988 1988 CD cord-276598-tm0yj2sn 131 19 and and CC cord-276598-tm0yj2sn 131 20 highlight highlight VB cord-276598-tm0yj2sn 131 21 the the DT cord-276598-tm0yj2sn 131 22 main main JJ cord-276598-tm0yj2sn 131 23 pioneers pioneer NNS cord-276598-tm0yj2sn 131 24 in in IN cord-276598-tm0yj2sn 131 25 the the DT cord-276598-tm0yj2sn 131 26 field field NN cord-276598-tm0yj2sn 131 27 ( ( -LRB- cord-276598-tm0yj2sn 131 28 Figure figure NN cord-276598-tm0yj2sn 131 29 4 4 CD cord-276598-tm0yj2sn 131 30 ) ) -RRB- cord-276598-tm0yj2sn 131 31 . . . cord-276598-tm0yj2sn 132 1 The the DT cord-276598-tm0yj2sn 132 2 research research NN cord-276598-tm0yj2sn 132 3 in in IN cord-276598-tm0yj2sn 132 4 these these DT cord-276598-tm0yj2sn 132 5 initial initial JJ cord-276598-tm0yj2sn 132 6 studies study NNS cord-276598-tm0yj2sn 132 7 has have VBZ cord-276598-tm0yj2sn 132 8 focused focus VBN cord-276598-tm0yj2sn 132 9 on on IN cord-276598-tm0yj2sn 132 10 reducing reduce VBG cord-276598-tm0yj2sn 132 11 waste waste NN cord-276598-tm0yj2sn 132 12 , , , cord-276598-tm0yj2sn 132 13 limiting limit VBG cord-276598-tm0yj2sn 132 14 toxic toxic JJ cord-276598-tm0yj2sn 132 15 reagents reagent NNS cord-276598-tm0yj2sn 132 16 , , , cord-276598-tm0yj2sn 132 17 improving improve VBG cord-276598-tm0yj2sn 132 18 selectivity selectivity NN cord-276598-tm0yj2sn 132 19 , , , cord-276598-tm0yj2sn 132 20 expanding expand VBG cord-276598-tm0yj2sn 132 21 scope scope NN cord-276598-tm0yj2sn 132 22 , , , cord-276598-tm0yj2sn 132 23 and and CC cord-276598-tm0yj2sn 132 24 searching search VBG cord-276598-tm0yj2sn 132 25 for for IN cord-276598-tm0yj2sn 132 26 effective effective JJ cord-276598-tm0yj2sn 132 27 and and CC cord-276598-tm0yj2sn 132 28 efficient efficient JJ cord-276598-tm0yj2sn 132 29 catalytic catalytic JJ cord-276598-tm0yj2sn 132 30 P p NN cord-276598-tm0yj2sn 132 31 - - HYPH cord-276598-tm0yj2sn 132 32 N n CD cord-276598-tm0yj2sn 132 33 bond bond NN cord-276598-tm0yj2sn 132 34 - - HYPH cord-276598-tm0yj2sn 132 35 making make VBG cord-276598-tm0yj2sn 132 36 solutions solution NNS cord-276598-tm0yj2sn 132 37 . . . cord-276598-tm0yj2sn 132 38 _SP cord-276598-tm0yj2sn 133 1 A a DT cord-276598-tm0yj2sn 133 2 synthetic synthetic JJ cord-276598-tm0yj2sn 133 3 P p NN cord-276598-tm0yj2sn 133 4 - - HYPH cord-276598-tm0yj2sn 133 5 N N NNP cord-276598-tm0yj2sn 133 6 was be VBD cord-276598-tm0yj2sn 133 7 fortuitously fortuitously RB cord-276598-tm0yj2sn 133 8 prepared prepare VBN cord-276598-tm0yj2sn 133 9 by by IN cord-276598-tm0yj2sn 133 10 Atherton Atherton NNP cord-276598-tm0yj2sn 133 11 , , , cord-276598-tm0yj2sn 133 12 Openshaw Openshaw NNP cord-276598-tm0yj2sn 133 13 , , , cord-276598-tm0yj2sn 133 14 and and CC cord-276598-tm0yj2sn 133 15 Todd Todd NNP cord-276598-tm0yj2sn 133 16 in in IN cord-276598-tm0yj2sn 133 17 1945 1945 CD cord-276598-tm0yj2sn 133 18 by by IN cord-276598-tm0yj2sn 133 19 the the DT cord-276598-tm0yj2sn 133 20 salt salt NN cord-276598-tm0yj2sn 133 21 elimination elimination NN cord-276598-tm0yj2sn 133 22 method method NN cord-276598-tm0yj2sn 133 23 using use VBG cord-276598-tm0yj2sn 133 24 H h NN cord-276598-tm0yj2sn 133 25 - - HYPH cord-276598-tm0yj2sn 133 26 phosphonates phosphonates FW cord-276598-tm0yj2sn 133 27 ( ( -LRB- cord-276598-tm0yj2sn 133 28 H h NN cord-276598-tm0yj2sn 133 29 - - HYPH cord-276598-tm0yj2sn 133 30 P p NN cord-276598-tm0yj2sn 133 31 ) ) -RRB- cord-276598-tm0yj2sn 133 32 ( ( -LRB- cord-276598-tm0yj2sn 133 33 ( ( -LRB- cord-276598-tm0yj2sn 133 34 RO RO NNP cord-276598-tm0yj2sn 133 35 ) ) -RRB- cord-276598-tm0yj2sn 133 36 2 2 CD cord-276598-tm0yj2sn 133 37 P(O)H p(o)h NN cord-276598-tm0yj2sn 133 38 ; ; : cord-276598-tm0yj2sn 134 1 R r NN cord-276598-tm0yj2sn 134 2 = = FW cord-276598-tm0yj2sn 134 3 Et Et NNP cord-276598-tm0yj2sn 134 4 , , , cord-276598-tm0yj2sn 134 5 i i NN cord-276598-tm0yj2sn 134 6 - - HYPH cord-276598-tm0yj2sn 134 7 Pr Pr NNP cord-276598-tm0yj2sn 134 8 , , , cord-276598-tm0yj2sn 134 9 Bn Bn NNP cord-276598-tm0yj2sn 134 10 ) ) -RRB- cord-276598-tm0yj2sn 134 11 and and CC cord-276598-tm0yj2sn 134 12 ammonia ammonia NN cord-276598-tm0yj2sn 134 13 in in IN cord-276598-tm0yj2sn 134 14 the the DT cord-276598-tm0yj2sn 134 15 presence presence NN cord-276598-tm0yj2sn 134 16 of of IN cord-276598-tm0yj2sn 134 17 a a DT cord-276598-tm0yj2sn 134 18 base base NN cord-276598-tm0yj2sn 134 19 ( ( -LRB- cord-276598-tm0yj2sn 134 20 Scheme scheme NN cord-276598-tm0yj2sn 134 21 2 2 CD cord-276598-tm0yj2sn 134 22 route route NN cord-276598-tm0yj2sn 134 23 B b NN cord-276598-tm0yj2sn 134 24 ) ) -RRB- cord-276598-tm0yj2sn 134 25 [ [ -LRB- cord-276598-tm0yj2sn 134 26 78 78 CD cord-276598-tm0yj2sn 134 27 ] ] -RRB- cord-276598-tm0yj2sn 134 28 . . . cord-276598-tm0yj2sn 135 1 The the DT cord-276598-tm0yj2sn 135 2 scope scope NN cord-276598-tm0yj2sn 135 3 of of IN cord-276598-tm0yj2sn 135 4 this this DT cord-276598-tm0yj2sn 135 5 method method NN cord-276598-tm0yj2sn 135 6 was be VBD cord-276598-tm0yj2sn 135 7 investigated investigate VBN cord-276598-tm0yj2sn 135 8 using use VBG cord-276598-tm0yj2sn 135 9 different different JJ cord-276598-tm0yj2sn 135 10 amines amine NNS cord-276598-tm0yj2sn 135 11 ( ( -LRB- cord-276598-tm0yj2sn 135 12 e.g. e.g. RB cord-276598-tm0yj2sn 135 13 , , , cord-276598-tm0yj2sn 135 14 morpholine morpholine NNP cord-276598-tm0yj2sn 135 15 , , , cord-276598-tm0yj2sn 135 16 cyclohexylamine cyclohexylamine NNP cord-276598-tm0yj2sn 135 17 , , , cord-276598-tm0yj2sn 135 18 1-phenylethan-1-amine 1-phenylethan-1-amine CD cord-276598-tm0yj2sn 135 19 and and CC cord-276598-tm0yj2sn 135 20 benzylamine benzylamine NN cord-276598-tm0yj2sn 135 21 , , , cord-276598-tm0yj2sn 135 22 4-methylmorpholine 4-methylmorpholine CD cord-276598-tm0yj2sn 135 23 ) ) -RRB- cord-276598-tm0yj2sn 135 24 or or CC cord-276598-tm0yj2sn 135 25 a a DT cord-276598-tm0yj2sn 135 26 mixture mixture NN cord-276598-tm0yj2sn 135 27 of of IN cord-276598-tm0yj2sn 135 28 aniline aniline NN cord-276598-tm0yj2sn 135 29 and and CC cord-276598-tm0yj2sn 135 30 N N NNP cord-276598-tm0yj2sn 135 31 , , , cord-276598-tm0yj2sn 135 32 N N NNP cord-276598-tm0yj2sn 135 33 - - HYPH cord-276598-tm0yj2sn 135 34 dimethylcyclohexanamine dimethylcyclohexanamine NNP cord-276598-tm0yj2sn 135 35 , , , cord-276598-tm0yj2sn 135 36 as as RB cord-276598-tm0yj2sn 135 37 well well RB cord-276598-tm0yj2sn 135 38 as as IN cord-276598-tm0yj2sn 135 39 different different JJ cord-276598-tm0yj2sn 135 40 solvents solvent NNS cord-276598-tm0yj2sn 135 41 ( ( -LRB- cord-276598-tm0yj2sn 135 42 e.g. e.g. RB cord-276598-tm0yj2sn 135 43 , , , cord-276598-tm0yj2sn 135 44 CCl CCl NNS cord-276598-tm0yj2sn 135 45 4 4 CD cord-276598-tm0yj2sn 135 46 , , , cord-276598-tm0yj2sn 135 47 Cl Cl NNP cord-276598-tm0yj2sn 135 48 3 3 CD cord-276598-tm0yj2sn 135 49 CCCl CCCl NNS cord-276598-tm0yj2sn 135 50 3 3 CD cord-276598-tm0yj2sn 135 51 , , , cord-276598-tm0yj2sn 135 52 and and CC cord-276598-tm0yj2sn 135 53 HCl hcl NN cord-276598-tm0yj2sn 135 54 2 2 CD cord-276598-tm0yj2sn 135 55 CCCl CCCl NNP cord-276598-tm0yj2sn 135 56 3 3 CD cord-276598-tm0yj2sn 135 57 ) ) -RRB- cord-276598-tm0yj2sn 135 58 . . . cord-276598-tm0yj2sn 136 1 Isolated isolated JJ cord-276598-tm0yj2sn 136 2 yields yield NNS cord-276598-tm0yj2sn 136 3 of of IN cord-276598-tm0yj2sn 136 4 62 62 CD cord-276598-tm0yj2sn 136 5 - - SYM cord-276598-tm0yj2sn 136 6 92 92 CD cord-276598-tm0yj2sn 136 7 % % NN cord-276598-tm0yj2sn 136 8 were be VBD cord-276598-tm0yj2sn 136 9 obtained obtain VBN cord-276598-tm0yj2sn 136 10 . . . cord-276598-tm0yj2sn 137 1 The the DT cord-276598-tm0yj2sn 137 2 Atherton Atherton NNP cord-276598-tm0yj2sn 137 3 - - HYPH cord-276598-tm0yj2sn 137 4 Todd Todd NNP cord-276598-tm0yj2sn 137 5 method method NN cord-276598-tm0yj2sn 137 6 was be VBD cord-276598-tm0yj2sn 137 7 prominent prominent JJ cord-276598-tm0yj2sn 137 8 for for IN cord-276598-tm0yj2sn 137 9 its -PRON- PRP$ cord-276598-tm0yj2sn 137 10 in in IN cord-276598-tm0yj2sn 137 11 situ situ JJ cord-276598-tm0yj2sn 137 12 generation generation NN cord-276598-tm0yj2sn 137 13 of of IN cord-276598-tm0yj2sn 137 14 ( ( -LRB- cord-276598-tm0yj2sn 137 15 RO ro NN cord-276598-tm0yj2sn 137 16 ) ) -RRB- cord-276598-tm0yj2sn 137 17 2 2 CD cord-276598-tm0yj2sn 138 1 P(O)Cl P(O)Cl VBN cord-276598-tm0yj2sn 139 1 ( ( -LRB- cord-276598-tm0yj2sn 139 2 dACP dacp JJ cord-276598-tm0yj2sn 139 3 ; ; : cord-276598-tm0yj2sn 139 4 R r NN cord-276598-tm0yj2sn 139 5 = = NN cord-276598-tm0yj2sn 139 6 alkyl alkyl NN cord-276598-tm0yj2sn 139 7 , , , cord-276598-tm0yj2sn 139 8 benzyl benzyl NN cord-276598-tm0yj2sn 139 9 ) ) -RRB- cord-276598-tm0yj2sn 139 10 , , , cord-276598-tm0yj2sn 139 11 which which WDT cord-276598-tm0yj2sn 139 12 eliminates eliminate VBZ cord-276598-tm0yj2sn 139 13 the the DT cord-276598-tm0yj2sn 139 14 use use NN cord-276598-tm0yj2sn 139 15 of of IN cord-276598-tm0yj2sn 139 16 moisture moisture NN cord-276598-tm0yj2sn 139 17 - - HYPH cord-276598-tm0yj2sn 139 18 and and CC cord-276598-tm0yj2sn 139 19 air air NN cord-276598-tm0yj2sn 139 20 - - HYPH cord-276598-tm0yj2sn 139 21 sensitive sensitive JJ cord-276598-tm0yj2sn 139 22 dACP dacp NN cord-276598-tm0yj2sn 139 23 . . . cord-276598-tm0yj2sn 140 1 However however RB cord-276598-tm0yj2sn 140 2 , , , cord-276598-tm0yj2sn 140 3 the the DT cord-276598-tm0yj2sn 140 4 major major JJ cord-276598-tm0yj2sn 140 5 drawbacks drawback NNS cord-276598-tm0yj2sn 140 6 of of IN cord-276598-tm0yj2sn 140 7 the the DT cord-276598-tm0yj2sn 140 8 method method NN cord-276598-tm0yj2sn 140 9 include include VBP cord-276598-tm0yj2sn 140 10 the the DT cord-276598-tm0yj2sn 140 11 use use NN cord-276598-tm0yj2sn 140 12 of of IN cord-276598-tm0yj2sn 140 13 halogen halogen NN cord-276598-tm0yj2sn 140 14 sources source NNS cord-276598-tm0yj2sn 140 15 such such JJ cord-276598-tm0yj2sn 140 16 as as IN cord-276598-tm0yj2sn 140 17 CCl CCl NNS cord-276598-tm0yj2sn 140 18 4 4 CD cord-276598-tm0yj2sn 140 19 , , , cord-276598-tm0yj2sn 140 20 Cl Cl NNP cord-276598-tm0yj2sn 140 21 3 3 CD cord-276598-tm0yj2sn 140 22 CCCl CCCl NNS cord-276598-tm0yj2sn 140 23 3 3 CD cord-276598-tm0yj2sn 140 24 , , , cord-276598-tm0yj2sn 140 25 and and CC cord-276598-tm0yj2sn 140 26 HCl hcl NN cord-276598-tm0yj2sn 140 27 2 2 CD cord-276598-tm0yj2sn 140 28 CCCl CCCl NNS cord-276598-tm0yj2sn 140 29 3 3 CD cord-276598-tm0yj2sn 140 30 and and CC cord-276598-tm0yj2sn 140 31 extensive extensive JJ cord-276598-tm0yj2sn 140 32 work work NN cord-276598-tm0yj2sn 140 33 - - HYPH cord-276598-tm0yj2sn 140 34 up up NN cord-276598-tm0yj2sn 140 35 / / SYM cord-276598-tm0yj2sn 140 36 purification purification NN cord-276598-tm0yj2sn 140 37 of of IN cord-276598-tm0yj2sn 140 38 the the DT cord-276598-tm0yj2sn 140 39 products product NNS cord-276598-tm0yj2sn 140 40 . . . cord-276598-tm0yj2sn 141 1 In in IN cord-276598-tm0yj2sn 141 2 2020 2020 CD cord-276598-tm0yj2sn 141 3 , , , cord-276598-tm0yj2sn 141 4 Chen Chen NNP cord-276598-tm0yj2sn 141 5 et et NNP cord-276598-tm0yj2sn 141 6 al al NNP cord-276598-tm0yj2sn 141 7 . . NNP cord-276598-tm0yj2sn 141 8 reported report VBD cord-276598-tm0yj2sn 141 9 a a DT cord-276598-tm0yj2sn 141 10 modified modify VBN cord-276598-tm0yj2sn 141 11 Atherton Atherton NNP cord-276598-tm0yj2sn 141 12 - - HYPH cord-276598-tm0yj2sn 141 13 Todd Todd NNP cord-276598-tm0yj2sn 141 14 reaction reaction NN cord-276598-tm0yj2sn 141 15 for for IN cord-276598-tm0yj2sn 141 16 the the DT cord-276598-tm0yj2sn 141 17 synthesis synthesis NN cord-276598-tm0yj2sn 141 18 of of IN cord-276598-tm0yj2sn 141 19 P P NNP cord-276598-tm0yj2sn 141 20 - - HYPH cord-276598-tm0yj2sn 141 21 Ns Ns NNP cord-276598-tm0yj2sn 141 22 using use VBG cord-276598-tm0yj2sn 141 23 air air NN cord-276598-tm0yj2sn 141 24 as as IN cord-276598-tm0yj2sn 141 25 a a DT cord-276598-tm0yj2sn 141 26 radical radical JJ cord-276598-tm0yj2sn 141 27 initiator initiator NN cord-276598-tm0yj2sn 141 28 ( ( -LRB- cord-276598-tm0yj2sn 141 29 Scheme scheme NN cord-276598-tm0yj2sn 141 30 3 3 CD cord-276598-tm0yj2sn 141 31 ) ) -RRB- cord-276598-tm0yj2sn 141 32 [ [ -LRB- cord-276598-tm0yj2sn 141 33 95 95 CD cord-276598-tm0yj2sn 141 34 ] ] -RRB- cord-276598-tm0yj2sn 141 35 . . . cord-276598-tm0yj2sn 142 1 The the DT cord-276598-tm0yj2sn 142 2 modified modify VBN cord-276598-tm0yj2sn 142 3 method method NN cord-276598-tm0yj2sn 142 4 explored explore VBN cord-276598-tm0yj2sn 142 5 P P NNP cord-276598-tm0yj2sn 142 6 - - HYPH cord-276598-tm0yj2sn 142 7 N n CD cord-276598-tm0yj2sn 142 8 synthesis synthesis NN cord-276598-tm0yj2sn 142 9 using use VBG cord-276598-tm0yj2sn 142 10 ( ( -LRB- cord-276598-tm0yj2sn 142 11 H h NN cord-276598-tm0yj2sn 142 12 - - HYPH cord-276598-tm0yj2sn 142 13 P p NN cord-276598-tm0yj2sn 142 14 ) ) -RRB- cord-276598-tm0yj2sn 142 15 ( ( -LRB- cord-276598-tm0yj2sn 143 1 ( ( -LRB- cord-276598-tm0yj2sn 143 2 RO RO NNP cord-276598-tm0yj2sn 143 3 ) ) -RRB- cord-276598-tm0yj2sn 143 4 2 2 CD cord-276598-tm0yj2sn 143 5 P(O)H p(o)h NN cord-276598-tm0yj2sn 143 6 ; ; : cord-276598-tm0yj2sn 143 7 R r NN cord-276598-tm0yj2sn 143 8 = = FW cord-276598-tm0yj2sn 143 9 Et et NN cord-276598-tm0yj2sn 143 10 , , , cord-276598-tm0yj2sn 143 11 i i NN cord-276598-tm0yj2sn 143 12 - - HYPH cord-276598-tm0yj2sn 143 13 Pr Pr NNP cord-276598-tm0yj2sn 143 14 , , , cord-276598-tm0yj2sn 143 15 Bu Bu NNP cord-276598-tm0yj2sn 143 16 , , , cord-276598-tm0yj2sn 143 17 i i PRP cord-276598-tm0yj2sn 143 18 - - HYPH cord-276598-tm0yj2sn 143 19 Bu Bu NNP cord-276598-tm0yj2sn 143 20 ) ) -RRB- cord-276598-tm0yj2sn 143 21 and and CC cord-276598-tm0yj2sn 143 22 benzylamine benzylamine JJ cord-276598-tm0yj2sn 143 23 with with IN cord-276598-tm0yj2sn 143 24 yields yield NNS cord-276598-tm0yj2sn 143 25 in in IN cord-276598-tm0yj2sn 143 26 the the DT cord-276598-tm0yj2sn 143 27 range range NN cord-276598-tm0yj2sn 143 28 of of IN cord-276598-tm0yj2sn 143 29 30 30 CD cord-276598-tm0yj2sn 143 30 - - SYM cord-276598-tm0yj2sn 143 31 75 75 CD cord-276598-tm0yj2sn 143 32 % % NN cord-276598-tm0yj2sn 143 33 . . . cord-276598-tm0yj2sn 144 1 Although although IN cord-276598-tm0yj2sn 144 2 this this DT cord-276598-tm0yj2sn 144 3 method method NN cord-276598-tm0yj2sn 144 4 offered offer VBD cord-276598-tm0yj2sn 144 5 advantages advantage NNS cord-276598-tm0yj2sn 144 6 such such JJ cord-276598-tm0yj2sn 144 7 as as IN cord-276598-tm0yj2sn 144 8 using use VBG cord-276598-tm0yj2sn 144 9 air air NN cord-276598-tm0yj2sn 144 10 as as IN cord-276598-tm0yj2sn 144 11 a a DT cord-276598-tm0yj2sn 144 12 radical radical JJ cord-276598-tm0yj2sn 144 13 initiator initiator NN cord-276598-tm0yj2sn 144 14 at at IN cord-276598-tm0yj2sn 144 15 room room NN cord-276598-tm0yj2sn 144 16 temperature temperature NN cord-276598-tm0yj2sn 144 17 , , , cord-276598-tm0yj2sn 144 18 the the DT cord-276598-tm0yj2sn 144 19 use use NN cord-276598-tm0yj2sn 144 20 of of IN cord-276598-tm0yj2sn 144 21 relatively relatively RB cord-276598-tm0yj2sn 144 22 expensive expensive JJ cord-276598-tm0yj2sn 144 23 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine CD cord-276598-tm0yj2sn 144 24 ( ( -LRB- cord-276598-tm0yj2sn 144 25 DBU DBU NNP cord-276598-tm0yj2sn 144 26 ) ) -RRB- cord-276598-tm0yj2sn 144 27 as as IN cord-276598-tm0yj2sn 144 28 a a DT cord-276598-tm0yj2sn 144 29 base base NN cord-276598-tm0yj2sn 144 30 in in IN cord-276598-tm0yj2sn 144 31 the the DT cord-276598-tm0yj2sn 144 32 process process NN cord-276598-tm0yj2sn 144 33 , , , cord-276598-tm0yj2sn 144 34 the the DT cord-276598-tm0yj2sn 144 35 elimination elimination NN cord-276598-tm0yj2sn 144 36 of of IN cord-276598-tm0yj2sn 144 37 large large JJ cord-276598-tm0yj2sn 144 38 amounts amount NNS cord-276598-tm0yj2sn 144 39 of of IN cord-276598-tm0yj2sn 144 40 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 144 41 waste waste NN cord-276598-tm0yj2sn 144 42 , , , cord-276598-tm0yj2sn 144 43 and and CC cord-276598-tm0yj2sn 144 44 comparatively comparatively RB cord-276598-tm0yj2sn 144 45 lower low JJR cord-276598-tm0yj2sn 144 46 yields yield NNS cord-276598-tm0yj2sn 144 47 of of IN cord-276598-tm0yj2sn 144 48 products product NNS cord-276598-tm0yj2sn 144 49 are be VBP cord-276598-tm0yj2sn 144 50 some some DT cord-276598-tm0yj2sn 144 51 of of IN cord-276598-tm0yj2sn 144 52 the the DT cord-276598-tm0yj2sn 144 53 limitations limitation NNS cord-276598-tm0yj2sn 144 54 . . . cord-276598-tm0yj2sn 145 1 [ [ -LRB- cord-276598-tm0yj2sn 145 2 78 78 CD cord-276598-tm0yj2sn 145 3 ] ] -RRB- cord-276598-tm0yj2sn 145 4 . . . cord-276598-tm0yj2sn 146 1 The the DT cord-276598-tm0yj2sn 146 2 scope scope NN cord-276598-tm0yj2sn 146 3 of of IN cord-276598-tm0yj2sn 146 4 this this DT cord-276598-tm0yj2sn 146 5 method method NN cord-276598-tm0yj2sn 146 6 was be VBD cord-276598-tm0yj2sn 146 7 investigated investigate VBN cord-276598-tm0yj2sn 146 8 using use VBG cord-276598-tm0yj2sn 146 9 different different JJ cord-276598-tm0yj2sn 146 10 amines amine NNS cord-276598-tm0yj2sn 146 11 ( ( -LRB- cord-276598-tm0yj2sn 146 12 e.g. e.g. RB cord-276598-tm0yj2sn 146 13 , , , cord-276598-tm0yj2sn 146 14 morpholine morpholine NNP cord-276598-tm0yj2sn 146 15 , , , cord-276598-tm0yj2sn 146 16 cyclohexylamine cyclohexylamine NNP cord-276598-tm0yj2sn 146 17 , , , cord-276598-tm0yj2sn 146 18 1-phenylethan-1-amine 1-phenylethan-1-amine CD cord-276598-tm0yj2sn 146 19 and and CC cord-276598-tm0yj2sn 146 20 benzylamine benzylamine NN cord-276598-tm0yj2sn 146 21 , , , cord-276598-tm0yj2sn 146 22 4-methylmorpholine 4-methylmorpholine CD cord-276598-tm0yj2sn 146 23 ) ) -RRB- cord-276598-tm0yj2sn 146 24 or or CC cord-276598-tm0yj2sn 146 25 a a DT cord-276598-tm0yj2sn 146 26 mixture mixture NN cord-276598-tm0yj2sn 146 27 of of IN cord-276598-tm0yj2sn 146 28 aniline aniline NN cord-276598-tm0yj2sn 146 29 and and CC cord-276598-tm0yj2sn 146 30 N N NNP cord-276598-tm0yj2sn 146 31 , , , cord-276598-tm0yj2sn 146 32 N N NNP cord-276598-tm0yj2sn 146 33 - - HYPH cord-276598-tm0yj2sn 146 34 dimethylcyclohexanamine dimethylcyclohexanamine NNP cord-276598-tm0yj2sn 146 35 , , , cord-276598-tm0yj2sn 146 36 as as RB cord-276598-tm0yj2sn 146 37 well well RB cord-276598-tm0yj2sn 146 38 as as IN cord-276598-tm0yj2sn 146 39 different different JJ cord-276598-tm0yj2sn 146 40 solvents solvent NNS cord-276598-tm0yj2sn 146 41 ( ( -LRB- cord-276598-tm0yj2sn 146 42 e.g. e.g. RB cord-276598-tm0yj2sn 146 43 , , , cord-276598-tm0yj2sn 146 44 CCl4 CCl4 NNP cord-276598-tm0yj2sn 146 45 , , , cord-276598-tm0yj2sn 146 46 Cl3CCCl3 Cl3CCCl3 NNP cord-276598-tm0yj2sn 146 47 , , , cord-276598-tm0yj2sn 146 48 and and CC cord-276598-tm0yj2sn 146 49 HCl2CCCl3 HCl2CCCl3 NNP cord-276598-tm0yj2sn 146 50 ) ) -RRB- cord-276598-tm0yj2sn 146 51 . . . cord-276598-tm0yj2sn 147 1 Isolated isolated JJ cord-276598-tm0yj2sn 147 2 yields yield NNS cord-276598-tm0yj2sn 147 3 of of IN cord-276598-tm0yj2sn 147 4 62 62 CD cord-276598-tm0yj2sn 147 5 - - SYM cord-276598-tm0yj2sn 147 6 92 92 CD cord-276598-tm0yj2sn 147 7 % % NN cord-276598-tm0yj2sn 147 8 were be VBD cord-276598-tm0yj2sn 147 9 obtained obtain VBN cord-276598-tm0yj2sn 147 10 . . . cord-276598-tm0yj2sn 148 1 The the DT cord-276598-tm0yj2sn 148 2 Atherton Atherton NNP cord-276598-tm0yj2sn 148 3 - - HYPH cord-276598-tm0yj2sn 148 4 Todd Todd NNP cord-276598-tm0yj2sn 148 5 method method NN cord-276598-tm0yj2sn 148 6 was be VBD cord-276598-tm0yj2sn 148 7 prominent prominent JJ cord-276598-tm0yj2sn 148 8 for for IN cord-276598-tm0yj2sn 148 9 its -PRON- PRP$ cord-276598-tm0yj2sn 148 10 in in IN cord-276598-tm0yj2sn 148 11 situ situ JJ cord-276598-tm0yj2sn 148 12 generation generation NN cord-276598-tm0yj2sn 148 13 of of IN cord-276598-tm0yj2sn 148 14 ( ( -LRB- cord-276598-tm0yj2sn 149 1 RO)2P(O)Cl RO)2P(O)Cl NNP cord-276598-tm0yj2sn 149 2 ( ( -LRB- cord-276598-tm0yj2sn 149 3 dACP dacp NN cord-276598-tm0yj2sn 149 4 ; ; : cord-276598-tm0yj2sn 149 5 R r NN cord-276598-tm0yj2sn 149 6 = = NN cord-276598-tm0yj2sn 149 7 alkyl alkyl NN cord-276598-tm0yj2sn 149 8 , , , cord-276598-tm0yj2sn 149 9 benzyl benzyl NN cord-276598-tm0yj2sn 149 10 ) ) -RRB- cord-276598-tm0yj2sn 149 11 , , , cord-276598-tm0yj2sn 149 12 which which WDT cord-276598-tm0yj2sn 149 13 eliminates eliminate VBZ cord-276598-tm0yj2sn 149 14 the the DT cord-276598-tm0yj2sn 149 15 use use NN cord-276598-tm0yj2sn 149 16 of of IN cord-276598-tm0yj2sn 149 17 moisture moisture NN cord-276598-tm0yj2sn 149 18 - - HYPH cord-276598-tm0yj2sn 149 19 and and CC cord-276598-tm0yj2sn 149 20 air air NN cord-276598-tm0yj2sn 149 21 - - HYPH cord-276598-tm0yj2sn 149 22 sensitive sensitive JJ cord-276598-tm0yj2sn 149 23 dACP dacp NN cord-276598-tm0yj2sn 149 24 . . . cord-276598-tm0yj2sn 150 1 However however RB cord-276598-tm0yj2sn 150 2 , , , cord-276598-tm0yj2sn 150 3 the the DT cord-276598-tm0yj2sn 150 4 major major JJ cord-276598-tm0yj2sn 150 5 drawbacks drawback NNS cord-276598-tm0yj2sn 150 6 of of IN cord-276598-tm0yj2sn 150 7 the the DT cord-276598-tm0yj2sn 150 8 method method NN cord-276598-tm0yj2sn 150 9 include include VBP cord-276598-tm0yj2sn 150 10 the the DT cord-276598-tm0yj2sn 150 11 use use NN cord-276598-tm0yj2sn 150 12 of of IN cord-276598-tm0yj2sn 150 13 halogen halogen NN cord-276598-tm0yj2sn 150 14 sources source NNS cord-276598-tm0yj2sn 150 15 such such JJ cord-276598-tm0yj2sn 150 16 as as IN cord-276598-tm0yj2sn 150 17 CCl4 CCl4 NNP cord-276598-tm0yj2sn 150 18 , , , cord-276598-tm0yj2sn 150 19 Cl3CCCl3 Cl3CCCl3 NNP cord-276598-tm0yj2sn 150 20 , , , cord-276598-tm0yj2sn 150 21 and and CC cord-276598-tm0yj2sn 150 22 HCl2CCCl3 HCl2CCCl3 NNP cord-276598-tm0yj2sn 150 23 and and CC cord-276598-tm0yj2sn 150 24 extensive extensive JJ cord-276598-tm0yj2sn 150 25 work work NN cord-276598-tm0yj2sn 150 26 - - HYPH cord-276598-tm0yj2sn 150 27 up up NN cord-276598-tm0yj2sn 150 28 / / SYM cord-276598-tm0yj2sn 150 29 purification purification NN cord-276598-tm0yj2sn 150 30 of of IN cord-276598-tm0yj2sn 150 31 the the DT cord-276598-tm0yj2sn 150 32 products product NNS cord-276598-tm0yj2sn 150 33 . . . cord-276598-tm0yj2sn 151 1 In in IN cord-276598-tm0yj2sn 151 2 2020 2020 CD cord-276598-tm0yj2sn 151 3 , , , cord-276598-tm0yj2sn 151 4 Chen Chen NNP cord-276598-tm0yj2sn 151 5 et et NNP cord-276598-tm0yj2sn 151 6 al al NNP cord-276598-tm0yj2sn 151 7 . . NNP cord-276598-tm0yj2sn 151 8 reported report VBD cord-276598-tm0yj2sn 151 9 a a DT cord-276598-tm0yj2sn 151 10 modified modify VBN cord-276598-tm0yj2sn 151 11 Atherton Atherton NNP cord-276598-tm0yj2sn 151 12 - - HYPH cord-276598-tm0yj2sn 151 13 Todd Todd NNP cord-276598-tm0yj2sn 151 14 reaction reaction NN cord-276598-tm0yj2sn 151 15 for for IN cord-276598-tm0yj2sn 151 16 the the DT cord-276598-tm0yj2sn 151 17 synthesis synthesis NN cord-276598-tm0yj2sn 151 18 of of IN cord-276598-tm0yj2sn 151 19 P P NNP cord-276598-tm0yj2sn 151 20 - - HYPH cord-276598-tm0yj2sn 151 21 Ns Ns NNP cord-276598-tm0yj2sn 151 22 using use VBG cord-276598-tm0yj2sn 151 23 air air NN cord-276598-tm0yj2sn 151 24 as as IN cord-276598-tm0yj2sn 151 25 a a DT cord-276598-tm0yj2sn 151 26 radical radical JJ cord-276598-tm0yj2sn 151 27 initiator initiator NN cord-276598-tm0yj2sn 151 28 ( ( -LRB- cord-276598-tm0yj2sn 151 29 Scheme scheme NN cord-276598-tm0yj2sn 151 30 3 3 CD cord-276598-tm0yj2sn 151 31 ) ) -RRB- cord-276598-tm0yj2sn 151 32 [ [ -LRB- cord-276598-tm0yj2sn 151 33 95 95 CD cord-276598-tm0yj2sn 151 34 ] ] -RRB- cord-276598-tm0yj2sn 151 35 . . . cord-276598-tm0yj2sn 152 1 The the DT cord-276598-tm0yj2sn 152 2 modified modify VBN cord-276598-tm0yj2sn 152 3 method method NN cord-276598-tm0yj2sn 152 4 explored explore VBN cord-276598-tm0yj2sn 152 5 P P NNP cord-276598-tm0yj2sn 152 6 - - HYPH cord-276598-tm0yj2sn 152 7 N n CD cord-276598-tm0yj2sn 152 8 synthesis synthesis NN cord-276598-tm0yj2sn 152 9 using use VBG cord-276598-tm0yj2sn 152 10 ( ( -LRB- cord-276598-tm0yj2sn 152 11 H h NN cord-276598-tm0yj2sn 152 12 - - HYPH cord-276598-tm0yj2sn 152 13 P p NN cord-276598-tm0yj2sn 152 14 ) ) -RRB- cord-276598-tm0yj2sn 152 15 ( ( -LRB- cord-276598-tm0yj2sn 152 16 ( ( -LRB- cord-276598-tm0yj2sn 152 17 RO)2P(O)H ro)2p(o)h NN cord-276598-tm0yj2sn 152 18 ; ; . cord-276598-tm0yj2sn 153 1 R r NN cord-276598-tm0yj2sn 153 2 = = FW cord-276598-tm0yj2sn 153 3 Et Et NNP cord-276598-tm0yj2sn 153 4 , , , cord-276598-tm0yj2sn 153 5 i i NN cord-276598-tm0yj2sn 153 6 - - HYPH cord-276598-tm0yj2sn 153 7 Pr Pr NNP cord-276598-tm0yj2sn 153 8 , , , cord-276598-tm0yj2sn 153 9 Bu Bu NNP cord-276598-tm0yj2sn 153 10 , , , cord-276598-tm0yj2sn 153 11 i i PRP cord-276598-tm0yj2sn 153 12 - - HYPH cord-276598-tm0yj2sn 153 13 Bu Bu NNP cord-276598-tm0yj2sn 153 14 ) ) -RRB- cord-276598-tm0yj2sn 153 15 and and CC cord-276598-tm0yj2sn 153 16 benzylamine benzylamine JJ cord-276598-tm0yj2sn 153 17 with with IN cord-276598-tm0yj2sn 153 18 yields yield NNS cord-276598-tm0yj2sn 153 19 in in IN cord-276598-tm0yj2sn 153 20 the the DT cord-276598-tm0yj2sn 153 21 range range NN cord-276598-tm0yj2sn 153 22 of of IN cord-276598-tm0yj2sn 153 23 30 30 CD cord-276598-tm0yj2sn 153 24 - - SYM cord-276598-tm0yj2sn 153 25 75 75 CD cord-276598-tm0yj2sn 153 26 % % NN cord-276598-tm0yj2sn 153 27 . . . cord-276598-tm0yj2sn 154 1 Although although IN cord-276598-tm0yj2sn 154 2 this this DT cord-276598-tm0yj2sn 154 3 method method NN cord-276598-tm0yj2sn 154 4 offered offer VBD cord-276598-tm0yj2sn 154 5 advantages advantage NNS cord-276598-tm0yj2sn 154 6 such such JJ cord-276598-tm0yj2sn 154 7 as as IN cord-276598-tm0yj2sn 154 8 using use VBG cord-276598-tm0yj2sn 154 9 air air NN cord-276598-tm0yj2sn 154 10 as as IN cord-276598-tm0yj2sn 154 11 a a DT cord-276598-tm0yj2sn 154 12 radical radical JJ cord-276598-tm0yj2sn 154 13 initiator initiator NN cord-276598-tm0yj2sn 154 14 at at IN cord-276598-tm0yj2sn 154 15 room room NN cord-276598-tm0yj2sn 154 16 temperature temperature NN cord-276598-tm0yj2sn 154 17 , , , cord-276598-tm0yj2sn 154 18 the the DT cord-276598-tm0yj2sn 154 19 use use NN cord-276598-tm0yj2sn 154 20 of of IN cord-276598-tm0yj2sn 154 21 relatively relatively RB cord-276598-tm0yj2sn 154 22 expensive expensive JJ cord-276598-tm0yj2sn 154 23 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine CD cord-276598-tm0yj2sn 154 24 ( ( -LRB- cord-276598-tm0yj2sn 154 25 DBU DBU NNP cord-276598-tm0yj2sn 154 26 ) ) -RRB- cord-276598-tm0yj2sn 154 27 as as IN cord-276598-tm0yj2sn 154 28 a a DT cord-276598-tm0yj2sn 154 29 base base NN cord-276598-tm0yj2sn 154 30 in in IN cord-276598-tm0yj2sn 154 31 the the DT cord-276598-tm0yj2sn 154 32 process process NN cord-276598-tm0yj2sn 154 33 , , , cord-276598-tm0yj2sn 154 34 the the DT cord-276598-tm0yj2sn 154 35 elimination elimination NN cord-276598-tm0yj2sn 154 36 of of IN cord-276598-tm0yj2sn 154 37 large large JJ cord-276598-tm0yj2sn 154 38 amounts amount NNS cord-276598-tm0yj2sn 154 39 of of IN cord-276598-tm0yj2sn 154 40 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 154 41 waste waste NN cord-276598-tm0yj2sn 154 42 , , , cord-276598-tm0yj2sn 154 43 and and CC cord-276598-tm0yj2sn 154 44 comparatively comparatively RB cord-276598-tm0yj2sn 154 45 lower low JJR cord-276598-tm0yj2sn 154 46 yields yield NNS cord-276598-tm0yj2sn 154 47 of of IN cord-276598-tm0yj2sn 154 48 products product NNS cord-276598-tm0yj2sn 154 49 are be VBP cord-276598-tm0yj2sn 154 50 some some DT cord-276598-tm0yj2sn 154 51 of of IN cord-276598-tm0yj2sn 154 52 the the DT cord-276598-tm0yj2sn 154 53 limitations limitation NNS cord-276598-tm0yj2sn 154 54 . . . cord-276598-tm0yj2sn 154 55 _SP cord-276598-tm0yj2sn 155 1 With with IN cord-276598-tm0yj2sn 155 2 reference reference NN cord-276598-tm0yj2sn 155 3 to to IN cord-276598-tm0yj2sn 155 4 the the DT cord-276598-tm0yj2sn 155 5 limitations limitation NNS cord-276598-tm0yj2sn 155 6 ( ( -LRB- cord-276598-tm0yj2sn 155 7 such such JJ cord-276598-tm0yj2sn 155 8 as as IN cord-276598-tm0yj2sn 155 9 low low JJ cord-276598-tm0yj2sn 155 10 yield yield NN cord-276598-tm0yj2sn 155 11 and and CC cord-276598-tm0yj2sn 155 12 the the DT cord-276598-tm0yj2sn 155 13 formation formation NN cord-276598-tm0yj2sn 155 14 of of IN cord-276598-tm0yj2sn 155 15 organophosphorus organophosphorus JJ cord-276598-tm0yj2sn 155 16 anhydrides anhydride NNS cord-276598-tm0yj2sn 155 17 side side NN cord-276598-tm0yj2sn 155 18 products product NNS cord-276598-tm0yj2sn 155 19 ) ) -RRB- cord-276598-tm0yj2sn 155 20 in in IN cord-276598-tm0yj2sn 155 21 the the DT cord-276598-tm0yj2sn 155 22 method method NN cord-276598-tm0yj2sn 155 23 reported report VBN cord-276598-tm0yj2sn 155 24 by by IN cord-276598-tm0yj2sn 155 25 Appel Appel NNP cord-276598-tm0yj2sn 155 26 and and CC cord-276598-tm0yj2sn 155 27 Einig Einig NNP cord-276598-tm0yj2sn 155 28 [ [ -LRB- cord-276598-tm0yj2sn 155 29 86 86 CD cord-276598-tm0yj2sn 155 30 ] ] -RRB- cord-276598-tm0yj2sn 155 31 , , , cord-276598-tm0yj2sn 155 32 Zwierzak Zwierzak NNP cord-276598-tm0yj2sn 155 33 and and CC cord-276598-tm0yj2sn 155 34 Osowska Osowska NNP cord-276598-tm0yj2sn 155 35 - - HYPH cord-276598-tm0yj2sn 155 36 Pacewicka Pacewicka NNP cord-276598-tm0yj2sn 155 37 [ [ -LRB- cord-276598-tm0yj2sn 155 38 90 90 CD cord-276598-tm0yj2sn 155 39 ] ] -RRB- cord-276598-tm0yj2sn 155 40 proposed propose VBD cord-276598-tm0yj2sn 155 41 an an DT cord-276598-tm0yj2sn 155 42 alternative alternative JJ cord-276598-tm0yj2sn 155 43 method method NN cord-276598-tm0yj2sn 155 44 that that WDT cord-276598-tm0yj2sn 155 45 uses use VBZ cord-276598-tm0yj2sn 155 46 −OH −oh CD cord-276598-tm0yj2sn 155 47 group group NN cord-276598-tm0yj2sn 155 48 activator activator NN cord-276598-tm0yj2sn 155 49 , , , cord-276598-tm0yj2sn 155 50 hexamethyltriaminodibromophosphorane hexamethyltriaminodibromophosphorane NNP cord-276598-tm0yj2sn 155 51 ( ( -LRB- cord-276598-tm0yj2sn 155 52 ( ( -LRB- cord-276598-tm0yj2sn 155 53 Me2N)3PBr2 Me2N)3PBr2 NNP cord-276598-tm0yj2sn 155 54 ) ) -RRB- cord-276598-tm0yj2sn 155 55 . . . cord-276598-tm0yj2sn 156 1 In in IN cord-276598-tm0yj2sn 156 2 the the DT cord-276598-tm0yj2sn 156 3 reported report VBN cord-276598-tm0yj2sn 156 4 method method NN cord-276598-tm0yj2sn 156 5 , , , cord-276598-tm0yj2sn 156 6 ( ( -LRB- cord-276598-tm0yj2sn 156 7 Me2N)3PBr2 Me2N)3PBr2 NNP cord-276598-tm0yj2sn 156 8 was be VBD cord-276598-tm0yj2sn 156 9 prepared prepare VBN cord-276598-tm0yj2sn 156 10 in in IN cord-276598-tm0yj2sn 156 11 situ situ NNS cord-276598-tm0yj2sn 156 12 in in IN cord-276598-tm0yj2sn 156 13 a a DT cord-276598-tm0yj2sn 156 14 one one CD cord-276598-tm0yj2sn 156 15 - - HYPH cord-276598-tm0yj2sn 156 16 pot pot NN cord-276598-tm0yj2sn 156 17 two two CD cord-276598-tm0yj2sn 156 18 - - HYPH cord-276598-tm0yj2sn 156 19 step step NN cord-276598-tm0yj2sn 156 20 synthesis synthesis NN cord-276598-tm0yj2sn 156 21 of of IN cord-276598-tm0yj2sn 156 22 P p NN cord-276598-tm0yj2sn 156 23 - - HYPH cord-276598-tm0yj2sn 156 24 Ns Ns NNP cord-276598-tm0yj2sn 156 25 from from IN cord-276598-tm0yj2sn 156 26 ( ( -LRB- cord-276598-tm0yj2sn 156 27 EtO)2P(O)OH eto)2p(o)oh NN cord-276598-tm0yj2sn 156 28 and and CC cord-276598-tm0yj2sn 156 29 amines amine NNS cord-276598-tm0yj2sn 156 30 ( ( -LRB- cord-276598-tm0yj2sn 156 31 Scheme scheme NN cord-276598-tm0yj2sn 156 32 4 4 CD cord-276598-tm0yj2sn 156 33 ) ) -RRB- cord-276598-tm0yj2sn 156 34 [ [ -LRB- cord-276598-tm0yj2sn 156 35 90 90 CD cord-276598-tm0yj2sn 156 36 ] ] -RRB- cord-276598-tm0yj2sn 156 37 . . . cord-276598-tm0yj2sn 157 1 The the DT cord-276598-tm0yj2sn 157 2 synthesis synthesis NN cord-276598-tm0yj2sn 157 3 was be VBD cord-276598-tm0yj2sn 157 4 explored explore VBN cord-276598-tm0yj2sn 157 5 using use VBG cord-276598-tm0yj2sn 157 6 various various JJ cord-276598-tm0yj2sn 157 7 amines amine NNS cord-276598-tm0yj2sn 157 8 such such JJ cord-276598-tm0yj2sn 157 9 as as IN cord-276598-tm0yj2sn 157 10 aniline aniline NN cord-276598-tm0yj2sn 157 11 , , , cord-276598-tm0yj2sn 157 12 phenylmethanamine phenylmethanamine NN cord-276598-tm0yj2sn 157 13 , , , cord-276598-tm0yj2sn 157 14 dibutylamine dibutylamine NNP cord-276598-tm0yj2sn 157 15 , , , cord-276598-tm0yj2sn 157 16 butan-1-amine butan-1-amine NNP cord-276598-tm0yj2sn 157 17 , , , cord-276598-tm0yj2sn 157 18 dipropylamine dipropylamine NN cord-276598-tm0yj2sn 157 19 , , , cord-276598-tm0yj2sn 157 20 and and CC cord-276598-tm0yj2sn 157 21 hept-1-en-2-amine hept-1-en-2-amine NN cord-276598-tm0yj2sn 157 22 . . . cord-276598-tm0yj2sn 158 1 This this DT cord-276598-tm0yj2sn 158 2 method method NN cord-276598-tm0yj2sn 158 3 was be VBD cord-276598-tm0yj2sn 158 4 favorable favorable JJ cord-276598-tm0yj2sn 158 5 with with IN cord-276598-tm0yj2sn 158 6 improved improved JJ cord-276598-tm0yj2sn 158 7 yields yield NNS cord-276598-tm0yj2sn 158 8 of of IN cord-276598-tm0yj2sn 158 9 P p NN cord-276598-tm0yj2sn 158 10 - - HYPH cord-276598-tm0yj2sn 158 11 N n CD cord-276598-tm0yj2sn 158 12 products product NNS cord-276598-tm0yj2sn 158 13 ( ( -LRB- cord-276598-tm0yj2sn 158 14 59 59 CD cord-276598-tm0yj2sn 158 15 - - SYM cord-276598-tm0yj2sn 158 16 91 91 CD cord-276598-tm0yj2sn 158 17 % % NN cord-276598-tm0yj2sn 158 18 ) ) -RRB- cord-276598-tm0yj2sn 158 19 after after IN cord-276598-tm0yj2sn 158 20 workup workup NN cord-276598-tm0yj2sn 158 21 and and CC cord-276598-tm0yj2sn 158 22 eliminated eliminate VBD cord-276598-tm0yj2sn 158 23 the the DT cord-276598-tm0yj2sn 158 24 route(s route(s NNP cord-276598-tm0yj2sn 158 25 ) ) -RRB- cord-276598-tm0yj2sn 158 26 for for IN cord-276598-tm0yj2sn 158 27 anhydride anhydride NN cord-276598-tm0yj2sn 158 28 formation formation NN cord-276598-tm0yj2sn 158 29 . . . cord-276598-tm0yj2sn 159 1 Nevertheless nevertheless RB cord-276598-tm0yj2sn 159 2 , , , cord-276598-tm0yj2sn 159 3 the the DT cord-276598-tm0yj2sn 159 4 method method NN cord-276598-tm0yj2sn 159 5 used use VBN cord-276598-tm0yj2sn 159 6 potentially potentially RB cord-276598-tm0yj2sn 159 7 harmful harmful JJ cord-276598-tm0yj2sn 159 8 bromine bromine NN cord-276598-tm0yj2sn 159 9 in in IN cord-276598-tm0yj2sn 159 10 a a DT cord-276598-tm0yj2sn 159 11 multi multi JJ cord-276598-tm0yj2sn 159 12 - - JJ cord-276598-tm0yj2sn 159 13 step step JJ cord-276598-tm0yj2sn 159 14 tedious tedious JJ cord-276598-tm0yj2sn 159 15 process process NN cord-276598-tm0yj2sn 159 16 with with IN cord-276598-tm0yj2sn 159 17 low low JJ cord-276598-tm0yj2sn 159 18 atom atom NN cord-276598-tm0yj2sn 159 19 economy economy NN cord-276598-tm0yj2sn 159 20 . . . cord-276598-tm0yj2sn 159 21 _SP cord-276598-tm0yj2sn 160 1 With with IN cord-276598-tm0yj2sn 160 2 reference reference NN cord-276598-tm0yj2sn 160 3 to to IN cord-276598-tm0yj2sn 160 4 the the DT cord-276598-tm0yj2sn 160 5 limitations limitation NNS cord-276598-tm0yj2sn 160 6 ( ( -LRB- cord-276598-tm0yj2sn 160 7 such such JJ cord-276598-tm0yj2sn 160 8 as as IN cord-276598-tm0yj2sn 160 9 low low JJ cord-276598-tm0yj2sn 160 10 yield yield NN cord-276598-tm0yj2sn 160 11 and and CC cord-276598-tm0yj2sn 160 12 the the DT cord-276598-tm0yj2sn 160 13 formation formation NN cord-276598-tm0yj2sn 160 14 of of IN cord-276598-tm0yj2sn 160 15 organophosphorus organophosphorus JJ cord-276598-tm0yj2sn 160 16 anhydrides anhydride NNS cord-276598-tm0yj2sn 160 17 side side NN cord-276598-tm0yj2sn 160 18 products product NNS cord-276598-tm0yj2sn 160 19 ) ) -RRB- cord-276598-tm0yj2sn 160 20 in in IN cord-276598-tm0yj2sn 160 21 the the DT cord-276598-tm0yj2sn 160 22 method method NN cord-276598-tm0yj2sn 160 23 reported report VBN cord-276598-tm0yj2sn 160 24 by by IN cord-276598-tm0yj2sn 160 25 Appel Appel NNP cord-276598-tm0yj2sn 160 26 and and CC cord-276598-tm0yj2sn 160 27 Einig Einig NNP cord-276598-tm0yj2sn 160 28 [ [ -LRB- cord-276598-tm0yj2sn 160 29 86 86 CD cord-276598-tm0yj2sn 160 30 ] ] -RRB- cord-276598-tm0yj2sn 160 31 , , , cord-276598-tm0yj2sn 160 32 Zwierzak Zwierzak NNP cord-276598-tm0yj2sn 160 33 and and CC cord-276598-tm0yj2sn 160 34 Osowska Osowska NNP cord-276598-tm0yj2sn 160 35 - - HYPH cord-276598-tm0yj2sn 160 36 Pacewicka Pacewicka NNP cord-276598-tm0yj2sn 160 37 [ [ -LRB- cord-276598-tm0yj2sn 160 38 90 90 CD cord-276598-tm0yj2sn 160 39 ] ] -RRB- cord-276598-tm0yj2sn 160 40 proposed propose VBD cord-276598-tm0yj2sn 160 41 an an DT cord-276598-tm0yj2sn 160 42 alternative alternative JJ cord-276598-tm0yj2sn 160 43 method method NN cord-276598-tm0yj2sn 160 44 that that WDT cord-276598-tm0yj2sn 160 45 uses use VBZ cord-276598-tm0yj2sn 160 46 −OH −oh CD cord-276598-tm0yj2sn 160 47 group group NN cord-276598-tm0yj2sn 160 48 activator activator NN cord-276598-tm0yj2sn 160 49 , , , cord-276598-tm0yj2sn 160 50 hexamethyltriaminodibromophosphorane hexamethyltriaminodibromophosphorane NNP cord-276598-tm0yj2sn 160 51 ( ( -LRB- cord-276598-tm0yj2sn 160 52 ( ( -LRB- cord-276598-tm0yj2sn 160 53 Me Me NNP cord-276598-tm0yj2sn 160 54 2 2 CD cord-276598-tm0yj2sn 160 55 N n CD cord-276598-tm0yj2sn 160 56 ) ) -RRB- cord-276598-tm0yj2sn 160 57 3 3 CD cord-276598-tm0yj2sn 160 58 PBr PBr NNS cord-276598-tm0yj2sn 160 59 2 2 CD cord-276598-tm0yj2sn 160 60 ) ) -RRB- cord-276598-tm0yj2sn 160 61 . . . cord-276598-tm0yj2sn 161 1 In in IN cord-276598-tm0yj2sn 161 2 the the DT cord-276598-tm0yj2sn 161 3 reported report VBN cord-276598-tm0yj2sn 161 4 method method NN cord-276598-tm0yj2sn 161 5 , , , cord-276598-tm0yj2sn 161 6 ( ( -LRB- cord-276598-tm0yj2sn 161 7 Me Me NNP cord-276598-tm0yj2sn 161 8 2 2 CD cord-276598-tm0yj2sn 161 9 N n CD cord-276598-tm0yj2sn 161 10 ) ) -RRB- cord-276598-tm0yj2sn 161 11 3 3 CD cord-276598-tm0yj2sn 161 12 PBr PBr NNS cord-276598-tm0yj2sn 161 13 2 2 CD cord-276598-tm0yj2sn 161 14 was be VBD cord-276598-tm0yj2sn 161 15 prepared prepare VBN cord-276598-tm0yj2sn 161 16 in in IN cord-276598-tm0yj2sn 161 17 situ situ NNS cord-276598-tm0yj2sn 161 18 in in IN cord-276598-tm0yj2sn 161 19 a a DT cord-276598-tm0yj2sn 161 20 one one CD cord-276598-tm0yj2sn 161 21 - - HYPH cord-276598-tm0yj2sn 161 22 pot pot NN cord-276598-tm0yj2sn 161 23 two two CD cord-276598-tm0yj2sn 161 24 - - HYPH cord-276598-tm0yj2sn 161 25 step step NN cord-276598-tm0yj2sn 161 26 synthesis synthesis NN cord-276598-tm0yj2sn 161 27 of of IN cord-276598-tm0yj2sn 161 28 P p NN cord-276598-tm0yj2sn 161 29 - - HYPH cord-276598-tm0yj2sn 161 30 Ns Ns NNP cord-276598-tm0yj2sn 161 31 from from IN cord-276598-tm0yj2sn 161 32 ( ( -LRB- cord-276598-tm0yj2sn 161 33 EtO EtO NNP cord-276598-tm0yj2sn 161 34 ) ) -RRB- cord-276598-tm0yj2sn 162 1 2 2 CD cord-276598-tm0yj2sn 162 2 P(O)OH p(o)oh NN cord-276598-tm0yj2sn 162 3 and and CC cord-276598-tm0yj2sn 162 4 amines amine NNS cord-276598-tm0yj2sn 162 5 ( ( -LRB- cord-276598-tm0yj2sn 162 6 Scheme scheme NN cord-276598-tm0yj2sn 162 7 4 4 CD cord-276598-tm0yj2sn 162 8 ) ) -RRB- cord-276598-tm0yj2sn 162 9 [ [ -LRB- cord-276598-tm0yj2sn 162 10 90 90 CD cord-276598-tm0yj2sn 162 11 ] ] -RRB- cord-276598-tm0yj2sn 162 12 . . . cord-276598-tm0yj2sn 163 1 The the DT cord-276598-tm0yj2sn 163 2 synthesis synthesis NN cord-276598-tm0yj2sn 163 3 was be VBD cord-276598-tm0yj2sn 163 4 explored explore VBN cord-276598-tm0yj2sn 163 5 using use VBG cord-276598-tm0yj2sn 163 6 various various JJ cord-276598-tm0yj2sn 163 7 amines amine NNS cord-276598-tm0yj2sn 163 8 such such JJ cord-276598-tm0yj2sn 163 9 as as IN cord-276598-tm0yj2sn 163 10 aniline aniline NN cord-276598-tm0yj2sn 163 11 , , , cord-276598-tm0yj2sn 163 12 phenylmethanamine phenylmethanamine NN cord-276598-tm0yj2sn 163 13 , , , cord-276598-tm0yj2sn 163 14 dibutylamine dibutylamine NNP cord-276598-tm0yj2sn 163 15 , , , cord-276598-tm0yj2sn 163 16 butan-1-amine butan-1-amine NNP cord-276598-tm0yj2sn 163 17 , , , cord-276598-tm0yj2sn 163 18 dipropylamine dipropylamine NN cord-276598-tm0yj2sn 163 19 , , , cord-276598-tm0yj2sn 163 20 and and CC cord-276598-tm0yj2sn 163 21 hept-1-en-2-amine hept-1-en-2-amine NN cord-276598-tm0yj2sn 163 22 . . . cord-276598-tm0yj2sn 164 1 This this DT cord-276598-tm0yj2sn 164 2 method method NN cord-276598-tm0yj2sn 164 3 was be VBD cord-276598-tm0yj2sn 164 4 favorable favorable JJ cord-276598-tm0yj2sn 164 5 with with IN cord-276598-tm0yj2sn 164 6 improved improved JJ cord-276598-tm0yj2sn 164 7 yields yield NNS cord-276598-tm0yj2sn 164 8 of of IN cord-276598-tm0yj2sn 164 9 P p NN cord-276598-tm0yj2sn 164 10 - - HYPH cord-276598-tm0yj2sn 164 11 N n CD cord-276598-tm0yj2sn 164 12 products product NNS cord-276598-tm0yj2sn 164 13 ( ( -LRB- cord-276598-tm0yj2sn 164 14 59 59 CD cord-276598-tm0yj2sn 164 15 - - SYM cord-276598-tm0yj2sn 164 16 91 91 CD cord-276598-tm0yj2sn 164 17 % % NN cord-276598-tm0yj2sn 164 18 ) ) -RRB- cord-276598-tm0yj2sn 164 19 after after IN cord-276598-tm0yj2sn 164 20 workup workup NN cord-276598-tm0yj2sn 164 21 and and CC cord-276598-tm0yj2sn 164 22 eliminated eliminate VBD cord-276598-tm0yj2sn 164 23 the the DT cord-276598-tm0yj2sn 164 24 route(s route(s NNP cord-276598-tm0yj2sn 164 25 ) ) -RRB- cord-276598-tm0yj2sn 164 26 for for IN cord-276598-tm0yj2sn 164 27 anhydride anhydride NN cord-276598-tm0yj2sn 164 28 formation formation NN cord-276598-tm0yj2sn 164 29 . . . cord-276598-tm0yj2sn 165 1 Nevertheless nevertheless RB cord-276598-tm0yj2sn 165 2 , , , cord-276598-tm0yj2sn 165 3 the the DT cord-276598-tm0yj2sn 165 4 method method NN cord-276598-tm0yj2sn 165 5 used use VBN cord-276598-tm0yj2sn 165 6 potentially potentially RB cord-276598-tm0yj2sn 165 7 harmful harmful JJ cord-276598-tm0yj2sn 165 8 bromine bromine NN cord-276598-tm0yj2sn 165 9 in in IN cord-276598-tm0yj2sn 165 10 a a DT cord-276598-tm0yj2sn 165 11 multi multi JJ cord-276598-tm0yj2sn 165 12 - - JJ cord-276598-tm0yj2sn 165 13 step step JJ cord-276598-tm0yj2sn 165 14 tedious tedious JJ cord-276598-tm0yj2sn 165 15 process process NN cord-276598-tm0yj2sn 165 16 with with IN cord-276598-tm0yj2sn 165 17 low low JJ cord-276598-tm0yj2sn 165 18 atom atom NN cord-276598-tm0yj2sn 165 19 economy economy NN cord-276598-tm0yj2sn 165 20 . . . cord-276598-tm0yj2sn 166 1 [ [ -LRB- cord-276598-tm0yj2sn 166 2 78 78 CD cord-276598-tm0yj2sn 166 3 ] ] -RRB- cord-276598-tm0yj2sn 166 4 . . . cord-276598-tm0yj2sn 167 1 The the DT cord-276598-tm0yj2sn 167 2 scope scope NN cord-276598-tm0yj2sn 167 3 of of IN cord-276598-tm0yj2sn 167 4 this this DT cord-276598-tm0yj2sn 167 5 method method NN cord-276598-tm0yj2sn 167 6 was be VBD cord-276598-tm0yj2sn 167 7 investigated investigate VBN cord-276598-tm0yj2sn 167 8 using use VBG cord-276598-tm0yj2sn 167 9 different different JJ cord-276598-tm0yj2sn 167 10 amines amine NNS cord-276598-tm0yj2sn 167 11 ( ( -LRB- cord-276598-tm0yj2sn 167 12 e.g. e.g. RB cord-276598-tm0yj2sn 167 13 , , , cord-276598-tm0yj2sn 167 14 morpholine morpholine NNP cord-276598-tm0yj2sn 167 15 , , , cord-276598-tm0yj2sn 167 16 cyclohexylamine cyclohexylamine NNP cord-276598-tm0yj2sn 167 17 , , , cord-276598-tm0yj2sn 167 18 1-phenylethan-1-amine 1-phenylethan-1-amine CD cord-276598-tm0yj2sn 167 19 and and CC cord-276598-tm0yj2sn 167 20 benzylamine benzylamine NN cord-276598-tm0yj2sn 167 21 , , , cord-276598-tm0yj2sn 167 22 4-methylmorpholine 4-methylmorpholine CD cord-276598-tm0yj2sn 167 23 ) ) -RRB- cord-276598-tm0yj2sn 167 24 or or CC cord-276598-tm0yj2sn 167 25 a a DT cord-276598-tm0yj2sn 167 26 mixture mixture NN cord-276598-tm0yj2sn 167 27 of of IN cord-276598-tm0yj2sn 167 28 aniline aniline NN cord-276598-tm0yj2sn 167 29 and and CC cord-276598-tm0yj2sn 167 30 N N NNP cord-276598-tm0yj2sn 167 31 , , , cord-276598-tm0yj2sn 167 32 N N NNP cord-276598-tm0yj2sn 167 33 - - HYPH cord-276598-tm0yj2sn 167 34 dimethylcyclohexanamine dimethylcyclohexanamine NNP cord-276598-tm0yj2sn 167 35 , , , cord-276598-tm0yj2sn 167 36 as as RB cord-276598-tm0yj2sn 167 37 well well RB cord-276598-tm0yj2sn 167 38 as as IN cord-276598-tm0yj2sn 167 39 different different JJ cord-276598-tm0yj2sn 167 40 solvents solvent NNS cord-276598-tm0yj2sn 167 41 ( ( -LRB- cord-276598-tm0yj2sn 167 42 e.g. e.g. RB cord-276598-tm0yj2sn 167 43 , , , cord-276598-tm0yj2sn 167 44 CCl4 CCl4 NNP cord-276598-tm0yj2sn 167 45 , , , cord-276598-tm0yj2sn 167 46 Cl3CCCl3 Cl3CCCl3 NNP cord-276598-tm0yj2sn 167 47 , , , cord-276598-tm0yj2sn 167 48 and and CC cord-276598-tm0yj2sn 167 49 HCl2CCCl3 HCl2CCCl3 NNP cord-276598-tm0yj2sn 167 50 ) ) -RRB- cord-276598-tm0yj2sn 167 51 . . . cord-276598-tm0yj2sn 168 1 Isolated isolated JJ cord-276598-tm0yj2sn 168 2 yields yield NNS cord-276598-tm0yj2sn 168 3 of of IN cord-276598-tm0yj2sn 168 4 62 62 CD cord-276598-tm0yj2sn 168 5 - - SYM cord-276598-tm0yj2sn 168 6 92 92 CD cord-276598-tm0yj2sn 168 7 % % NN cord-276598-tm0yj2sn 168 8 were be VBD cord-276598-tm0yj2sn 168 9 obtained obtain VBN cord-276598-tm0yj2sn 168 10 . . . cord-276598-tm0yj2sn 169 1 The the DT cord-276598-tm0yj2sn 169 2 Atherton Atherton NNP cord-276598-tm0yj2sn 169 3 - - HYPH cord-276598-tm0yj2sn 169 4 Todd Todd NNP cord-276598-tm0yj2sn 169 5 method method NN cord-276598-tm0yj2sn 169 6 was be VBD cord-276598-tm0yj2sn 169 7 prominent prominent JJ cord-276598-tm0yj2sn 169 8 for for IN cord-276598-tm0yj2sn 169 9 its -PRON- PRP$ cord-276598-tm0yj2sn 169 10 in in IN cord-276598-tm0yj2sn 169 11 situ situ JJ cord-276598-tm0yj2sn 169 12 generation generation NN cord-276598-tm0yj2sn 169 13 of of IN cord-276598-tm0yj2sn 169 14 ( ( -LRB- cord-276598-tm0yj2sn 170 1 RO)2P(O)Cl RO)2P(O)Cl NNP cord-276598-tm0yj2sn 170 2 ( ( -LRB- cord-276598-tm0yj2sn 170 3 dACP dacp NN cord-276598-tm0yj2sn 170 4 ; ; : cord-276598-tm0yj2sn 170 5 R r NN cord-276598-tm0yj2sn 170 6 = = NN cord-276598-tm0yj2sn 170 7 alkyl alkyl NN cord-276598-tm0yj2sn 170 8 , , , cord-276598-tm0yj2sn 170 9 benzyl benzyl NN cord-276598-tm0yj2sn 170 10 ) ) -RRB- cord-276598-tm0yj2sn 170 11 , , , cord-276598-tm0yj2sn 170 12 which which WDT cord-276598-tm0yj2sn 170 13 eliminates eliminate VBZ cord-276598-tm0yj2sn 170 14 the the DT cord-276598-tm0yj2sn 170 15 use use NN cord-276598-tm0yj2sn 170 16 of of IN cord-276598-tm0yj2sn 170 17 moisture moisture NN cord-276598-tm0yj2sn 170 18 - - HYPH cord-276598-tm0yj2sn 170 19 and and CC cord-276598-tm0yj2sn 170 20 air air NN cord-276598-tm0yj2sn 170 21 - - HYPH cord-276598-tm0yj2sn 170 22 sensitive sensitive JJ cord-276598-tm0yj2sn 170 23 dACP dacp NN cord-276598-tm0yj2sn 170 24 . . . cord-276598-tm0yj2sn 171 1 However however RB cord-276598-tm0yj2sn 171 2 , , , cord-276598-tm0yj2sn 171 3 the the DT cord-276598-tm0yj2sn 171 4 major major JJ cord-276598-tm0yj2sn 171 5 drawbacks drawback NNS cord-276598-tm0yj2sn 171 6 of of IN cord-276598-tm0yj2sn 171 7 the the DT cord-276598-tm0yj2sn 171 8 method method NN cord-276598-tm0yj2sn 171 9 include include VBP cord-276598-tm0yj2sn 171 10 the the DT cord-276598-tm0yj2sn 171 11 use use NN cord-276598-tm0yj2sn 171 12 of of IN cord-276598-tm0yj2sn 171 13 halogen halogen NN cord-276598-tm0yj2sn 171 14 sources source NNS cord-276598-tm0yj2sn 171 15 such such JJ cord-276598-tm0yj2sn 171 16 as as IN cord-276598-tm0yj2sn 171 17 CCl4 CCl4 NNP cord-276598-tm0yj2sn 171 18 , , , cord-276598-tm0yj2sn 171 19 Cl3CCCl3 Cl3CCCl3 NNP cord-276598-tm0yj2sn 171 20 , , , cord-276598-tm0yj2sn 171 21 and and CC cord-276598-tm0yj2sn 171 22 HCl2CCCl3 HCl2CCCl3 NNP cord-276598-tm0yj2sn 171 23 and and CC cord-276598-tm0yj2sn 171 24 extensive extensive JJ cord-276598-tm0yj2sn 171 25 work work NN cord-276598-tm0yj2sn 171 26 - - HYPH cord-276598-tm0yj2sn 171 27 up up NN cord-276598-tm0yj2sn 171 28 / / SYM cord-276598-tm0yj2sn 171 29 purification purification NN cord-276598-tm0yj2sn 171 30 of of IN cord-276598-tm0yj2sn 171 31 the the DT cord-276598-tm0yj2sn 171 32 products product NNS cord-276598-tm0yj2sn 171 33 . . . cord-276598-tm0yj2sn 172 1 In in IN cord-276598-tm0yj2sn 172 2 2020 2020 CD cord-276598-tm0yj2sn 172 3 , , , cord-276598-tm0yj2sn 172 4 Chen Chen NNP cord-276598-tm0yj2sn 172 5 et et NNP cord-276598-tm0yj2sn 172 6 al al NNP cord-276598-tm0yj2sn 172 7 . . NNP cord-276598-tm0yj2sn 172 8 reported report VBD cord-276598-tm0yj2sn 172 9 a a DT cord-276598-tm0yj2sn 172 10 modified modify VBN cord-276598-tm0yj2sn 172 11 Atherton Atherton NNP cord-276598-tm0yj2sn 172 12 - - HYPH cord-276598-tm0yj2sn 172 13 Todd Todd NNP cord-276598-tm0yj2sn 172 14 reaction reaction NN cord-276598-tm0yj2sn 172 15 for for IN cord-276598-tm0yj2sn 172 16 the the DT cord-276598-tm0yj2sn 172 17 synthesis synthesis NN cord-276598-tm0yj2sn 172 18 of of IN cord-276598-tm0yj2sn 172 19 P P NNP cord-276598-tm0yj2sn 172 20 - - HYPH cord-276598-tm0yj2sn 172 21 Ns Ns NNP cord-276598-tm0yj2sn 172 22 using use VBG cord-276598-tm0yj2sn 172 23 air air NN cord-276598-tm0yj2sn 172 24 as as IN cord-276598-tm0yj2sn 172 25 a a DT cord-276598-tm0yj2sn 172 26 radical radical JJ cord-276598-tm0yj2sn 172 27 initiator initiator NN cord-276598-tm0yj2sn 172 28 ( ( -LRB- cord-276598-tm0yj2sn 172 29 Scheme scheme NN cord-276598-tm0yj2sn 172 30 3 3 CD cord-276598-tm0yj2sn 172 31 ) ) -RRB- cord-276598-tm0yj2sn 172 32 [ [ -LRB- cord-276598-tm0yj2sn 172 33 95 95 CD cord-276598-tm0yj2sn 172 34 ] ] -RRB- cord-276598-tm0yj2sn 172 35 . . . cord-276598-tm0yj2sn 173 1 The the DT cord-276598-tm0yj2sn 173 2 modified modify VBN cord-276598-tm0yj2sn 173 3 method method NN cord-276598-tm0yj2sn 173 4 explored explore VBN cord-276598-tm0yj2sn 173 5 P P NNP cord-276598-tm0yj2sn 173 6 - - HYPH cord-276598-tm0yj2sn 173 7 N n CD cord-276598-tm0yj2sn 173 8 synthesis synthesis NN cord-276598-tm0yj2sn 173 9 using use VBG cord-276598-tm0yj2sn 173 10 ( ( -LRB- cord-276598-tm0yj2sn 173 11 H h NN cord-276598-tm0yj2sn 173 12 - - HYPH cord-276598-tm0yj2sn 173 13 P p NN cord-276598-tm0yj2sn 173 14 ) ) -RRB- cord-276598-tm0yj2sn 173 15 ( ( -LRB- cord-276598-tm0yj2sn 173 16 ( ( -LRB- cord-276598-tm0yj2sn 173 17 RO)2P(O)H ro)2p(o)h NN cord-276598-tm0yj2sn 173 18 ; ; . cord-276598-tm0yj2sn 174 1 R r NN cord-276598-tm0yj2sn 174 2 = = FW cord-276598-tm0yj2sn 174 3 Et Et NNP cord-276598-tm0yj2sn 174 4 , , , cord-276598-tm0yj2sn 174 5 i i NN cord-276598-tm0yj2sn 174 6 - - HYPH cord-276598-tm0yj2sn 174 7 Pr Pr NNP cord-276598-tm0yj2sn 174 8 , , , cord-276598-tm0yj2sn 174 9 Bu Bu NNP cord-276598-tm0yj2sn 174 10 , , , cord-276598-tm0yj2sn 174 11 i i PRP cord-276598-tm0yj2sn 174 12 - - HYPH cord-276598-tm0yj2sn 174 13 Bu Bu NNP cord-276598-tm0yj2sn 174 14 ) ) -RRB- cord-276598-tm0yj2sn 174 15 and and CC cord-276598-tm0yj2sn 174 16 benzylamine benzylamine JJ cord-276598-tm0yj2sn 174 17 with with IN cord-276598-tm0yj2sn 174 18 yields yield NNS cord-276598-tm0yj2sn 174 19 in in IN cord-276598-tm0yj2sn 174 20 the the DT cord-276598-tm0yj2sn 174 21 range range NN cord-276598-tm0yj2sn 174 22 of of IN cord-276598-tm0yj2sn 174 23 30 30 CD cord-276598-tm0yj2sn 174 24 - - SYM cord-276598-tm0yj2sn 174 25 75 75 CD cord-276598-tm0yj2sn 174 26 % % NN cord-276598-tm0yj2sn 174 27 . . . cord-276598-tm0yj2sn 175 1 Although although IN cord-276598-tm0yj2sn 175 2 this this DT cord-276598-tm0yj2sn 175 3 method method NN cord-276598-tm0yj2sn 175 4 offered offer VBD cord-276598-tm0yj2sn 175 5 advantages advantage NNS cord-276598-tm0yj2sn 175 6 such such JJ cord-276598-tm0yj2sn 175 7 as as IN cord-276598-tm0yj2sn 175 8 using use VBG cord-276598-tm0yj2sn 175 9 air air NN cord-276598-tm0yj2sn 175 10 as as IN cord-276598-tm0yj2sn 175 11 a a DT cord-276598-tm0yj2sn 175 12 radical radical JJ cord-276598-tm0yj2sn 175 13 initiator initiator NN cord-276598-tm0yj2sn 175 14 at at IN cord-276598-tm0yj2sn 175 15 room room NN cord-276598-tm0yj2sn 175 16 temperature temperature NN cord-276598-tm0yj2sn 175 17 , , , cord-276598-tm0yj2sn 175 18 the the DT cord-276598-tm0yj2sn 175 19 use use NN cord-276598-tm0yj2sn 175 20 of of IN cord-276598-tm0yj2sn 175 21 relatively relatively RB cord-276598-tm0yj2sn 175 22 expensive expensive JJ cord-276598-tm0yj2sn 175 23 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine CD cord-276598-tm0yj2sn 175 24 ( ( -LRB- cord-276598-tm0yj2sn 175 25 DBU DBU NNP cord-276598-tm0yj2sn 175 26 ) ) -RRB- cord-276598-tm0yj2sn 175 27 as as IN cord-276598-tm0yj2sn 175 28 a a DT cord-276598-tm0yj2sn 175 29 base base NN cord-276598-tm0yj2sn 175 30 in in IN cord-276598-tm0yj2sn 175 31 the the DT cord-276598-tm0yj2sn 175 32 process process NN cord-276598-tm0yj2sn 175 33 , , , cord-276598-tm0yj2sn 175 34 the the DT cord-276598-tm0yj2sn 175 35 elimination elimination NN cord-276598-tm0yj2sn 175 36 of of IN cord-276598-tm0yj2sn 175 37 large large JJ cord-276598-tm0yj2sn 175 38 amounts amount NNS cord-276598-tm0yj2sn 175 39 of of IN cord-276598-tm0yj2sn 175 40 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 175 41 waste waste NN cord-276598-tm0yj2sn 175 42 , , , cord-276598-tm0yj2sn 175 43 and and CC cord-276598-tm0yj2sn 175 44 comparatively comparatively RB cord-276598-tm0yj2sn 175 45 lower low JJR cord-276598-tm0yj2sn 175 46 yields yield NNS cord-276598-tm0yj2sn 175 47 of of IN cord-276598-tm0yj2sn 175 48 products product NNS cord-276598-tm0yj2sn 175 49 are be VBP cord-276598-tm0yj2sn 175 50 some some DT cord-276598-tm0yj2sn 175 51 of of IN cord-276598-tm0yj2sn 175 52 the the DT cord-276598-tm0yj2sn 175 53 limitations limitation NNS cord-276598-tm0yj2sn 175 54 . . . cord-276598-tm0yj2sn 175 55 _SP cord-276598-tm0yj2sn 176 1 With with IN cord-276598-tm0yj2sn 176 2 reference reference NN cord-276598-tm0yj2sn 176 3 to to IN cord-276598-tm0yj2sn 176 4 the the DT cord-276598-tm0yj2sn 176 5 limitations limitation NNS cord-276598-tm0yj2sn 176 6 ( ( -LRB- cord-276598-tm0yj2sn 176 7 such such JJ cord-276598-tm0yj2sn 176 8 as as IN cord-276598-tm0yj2sn 176 9 low low JJ cord-276598-tm0yj2sn 176 10 yield yield NN cord-276598-tm0yj2sn 176 11 and and CC cord-276598-tm0yj2sn 176 12 the the DT cord-276598-tm0yj2sn 176 13 formation formation NN cord-276598-tm0yj2sn 176 14 of of IN cord-276598-tm0yj2sn 176 15 organophosphorus organophosphorus JJ cord-276598-tm0yj2sn 176 16 anhydrides anhydride NNS cord-276598-tm0yj2sn 176 17 side side NN cord-276598-tm0yj2sn 176 18 products product NNS cord-276598-tm0yj2sn 176 19 ) ) -RRB- cord-276598-tm0yj2sn 176 20 in in IN cord-276598-tm0yj2sn 176 21 the the DT cord-276598-tm0yj2sn 176 22 method method NN cord-276598-tm0yj2sn 176 23 reported report VBN cord-276598-tm0yj2sn 176 24 by by IN cord-276598-tm0yj2sn 176 25 Appel Appel NNP cord-276598-tm0yj2sn 176 26 and and CC cord-276598-tm0yj2sn 176 27 Einig Einig NNP cord-276598-tm0yj2sn 176 28 [ [ -LRB- cord-276598-tm0yj2sn 176 29 86 86 CD cord-276598-tm0yj2sn 176 30 ] ] -RRB- cord-276598-tm0yj2sn 176 31 , , , cord-276598-tm0yj2sn 176 32 Zwierzak Zwierzak NNP cord-276598-tm0yj2sn 176 33 and and CC cord-276598-tm0yj2sn 176 34 Osowska Osowska NNP cord-276598-tm0yj2sn 176 35 - - HYPH cord-276598-tm0yj2sn 176 36 Pacewicka Pacewicka NNP cord-276598-tm0yj2sn 176 37 [ [ -LRB- cord-276598-tm0yj2sn 176 38 90 90 CD cord-276598-tm0yj2sn 176 39 ] ] -RRB- cord-276598-tm0yj2sn 176 40 proposed propose VBD cord-276598-tm0yj2sn 176 41 an an DT cord-276598-tm0yj2sn 176 42 alternative alternative JJ cord-276598-tm0yj2sn 176 43 method method NN cord-276598-tm0yj2sn 176 44 that that WDT cord-276598-tm0yj2sn 176 45 uses use VBZ cord-276598-tm0yj2sn 176 46 −OH −oh CD cord-276598-tm0yj2sn 176 47 group group NN cord-276598-tm0yj2sn 176 48 activator activator NN cord-276598-tm0yj2sn 176 49 , , , cord-276598-tm0yj2sn 176 50 hexamethyltriaminodibromophosphorane hexamethyltriaminodibromophosphorane NNP cord-276598-tm0yj2sn 176 51 ( ( -LRB- cord-276598-tm0yj2sn 176 52 ( ( -LRB- cord-276598-tm0yj2sn 176 53 Me2N)3PBr2 Me2N)3PBr2 NNP cord-276598-tm0yj2sn 176 54 ) ) -RRB- cord-276598-tm0yj2sn 176 55 . . . cord-276598-tm0yj2sn 177 1 In in IN cord-276598-tm0yj2sn 177 2 the the DT cord-276598-tm0yj2sn 177 3 reported report VBN cord-276598-tm0yj2sn 177 4 method method NN cord-276598-tm0yj2sn 177 5 , , , cord-276598-tm0yj2sn 177 6 ( ( -LRB- cord-276598-tm0yj2sn 177 7 Me2N)3PBr2 Me2N)3PBr2 NNP cord-276598-tm0yj2sn 177 8 was be VBD cord-276598-tm0yj2sn 177 9 prepared prepare VBN cord-276598-tm0yj2sn 177 10 in in IN cord-276598-tm0yj2sn 177 11 situ situ NNS cord-276598-tm0yj2sn 177 12 in in IN cord-276598-tm0yj2sn 177 13 a a DT cord-276598-tm0yj2sn 177 14 one one CD cord-276598-tm0yj2sn 177 15 - - HYPH cord-276598-tm0yj2sn 177 16 pot pot NN cord-276598-tm0yj2sn 177 17 two two CD cord-276598-tm0yj2sn 177 18 - - HYPH cord-276598-tm0yj2sn 177 19 step step NN cord-276598-tm0yj2sn 177 20 synthesis synthesis NN cord-276598-tm0yj2sn 177 21 of of IN cord-276598-tm0yj2sn 177 22 P p NN cord-276598-tm0yj2sn 177 23 - - HYPH cord-276598-tm0yj2sn 177 24 Ns Ns NNP cord-276598-tm0yj2sn 177 25 from from IN cord-276598-tm0yj2sn 177 26 ( ( -LRB- cord-276598-tm0yj2sn 177 27 EtO)2P(O)OH eto)2p(o)oh NN cord-276598-tm0yj2sn 177 28 and and CC cord-276598-tm0yj2sn 177 29 amines amine NNS cord-276598-tm0yj2sn 177 30 ( ( -LRB- cord-276598-tm0yj2sn 177 31 Scheme scheme NN cord-276598-tm0yj2sn 177 32 4 4 CD cord-276598-tm0yj2sn 177 33 ) ) -RRB- cord-276598-tm0yj2sn 177 34 [ [ -LRB- cord-276598-tm0yj2sn 177 35 90 90 CD cord-276598-tm0yj2sn 177 36 ] ] -RRB- cord-276598-tm0yj2sn 177 37 . . . cord-276598-tm0yj2sn 178 1 The the DT cord-276598-tm0yj2sn 178 2 synthesis synthesis NN cord-276598-tm0yj2sn 178 3 was be VBD cord-276598-tm0yj2sn 178 4 explored explore VBN cord-276598-tm0yj2sn 178 5 using use VBG cord-276598-tm0yj2sn 178 6 various various JJ cord-276598-tm0yj2sn 178 7 amines amine NNS cord-276598-tm0yj2sn 178 8 such such JJ cord-276598-tm0yj2sn 178 9 as as IN cord-276598-tm0yj2sn 178 10 aniline aniline NN cord-276598-tm0yj2sn 178 11 , , , cord-276598-tm0yj2sn 178 12 phenylmethanamine phenylmethanamine NN cord-276598-tm0yj2sn 178 13 , , , cord-276598-tm0yj2sn 178 14 dibutylamine dibutylamine NNP cord-276598-tm0yj2sn 178 15 , , , cord-276598-tm0yj2sn 178 16 butan-1-amine butan-1-amine NNP cord-276598-tm0yj2sn 178 17 , , , cord-276598-tm0yj2sn 178 18 dipropylamine dipropylamine NN cord-276598-tm0yj2sn 178 19 , , , cord-276598-tm0yj2sn 178 20 and and CC cord-276598-tm0yj2sn 178 21 hept-1-en-2-amine hept-1-en-2-amine NN cord-276598-tm0yj2sn 178 22 . . . cord-276598-tm0yj2sn 179 1 This this DT cord-276598-tm0yj2sn 179 2 method method NN cord-276598-tm0yj2sn 179 3 was be VBD cord-276598-tm0yj2sn 179 4 favorable favorable JJ cord-276598-tm0yj2sn 179 5 with with IN cord-276598-tm0yj2sn 179 6 improved improved JJ cord-276598-tm0yj2sn 179 7 yields yield NNS cord-276598-tm0yj2sn 179 8 of of IN cord-276598-tm0yj2sn 179 9 P p NN cord-276598-tm0yj2sn 179 10 - - HYPH cord-276598-tm0yj2sn 179 11 N n CD cord-276598-tm0yj2sn 179 12 products product NNS cord-276598-tm0yj2sn 179 13 ( ( -LRB- cord-276598-tm0yj2sn 179 14 59 59 CD cord-276598-tm0yj2sn 179 15 - - SYM cord-276598-tm0yj2sn 179 16 91 91 CD cord-276598-tm0yj2sn 179 17 % % NN cord-276598-tm0yj2sn 179 18 ) ) -RRB- cord-276598-tm0yj2sn 179 19 after after IN cord-276598-tm0yj2sn 179 20 workup workup NN cord-276598-tm0yj2sn 179 21 and and CC cord-276598-tm0yj2sn 179 22 eliminated eliminate VBD cord-276598-tm0yj2sn 179 23 the the DT cord-276598-tm0yj2sn 179 24 route(s route(s NNP cord-276598-tm0yj2sn 179 25 ) ) -RRB- cord-276598-tm0yj2sn 179 26 for for IN cord-276598-tm0yj2sn 179 27 anhydride anhydride NN cord-276598-tm0yj2sn 179 28 formation formation NN cord-276598-tm0yj2sn 179 29 . . . cord-276598-tm0yj2sn 180 1 Nevertheless nevertheless RB cord-276598-tm0yj2sn 180 2 , , , cord-276598-tm0yj2sn 180 3 the the DT cord-276598-tm0yj2sn 180 4 method method NN cord-276598-tm0yj2sn 180 5 used use VBN cord-276598-tm0yj2sn 180 6 potentially potentially RB cord-276598-tm0yj2sn 180 7 harmful harmful JJ cord-276598-tm0yj2sn 180 8 bromine bromine NN cord-276598-tm0yj2sn 180 9 in in IN cord-276598-tm0yj2sn 180 10 a a DT cord-276598-tm0yj2sn 180 11 multi multi JJ cord-276598-tm0yj2sn 180 12 - - JJ cord-276598-tm0yj2sn 180 13 step step JJ cord-276598-tm0yj2sn 180 14 tedious tedious JJ cord-276598-tm0yj2sn 180 15 process process NN cord-276598-tm0yj2sn 180 16 with with IN cord-276598-tm0yj2sn 180 17 low low JJ cord-276598-tm0yj2sn 180 18 atom atom NN cord-276598-tm0yj2sn 180 19 economy economy NN cord-276598-tm0yj2sn 180 20 . . . cord-276598-tm0yj2sn 181 1 In in IN cord-276598-tm0yj2sn 181 2 another another DT cord-276598-tm0yj2sn 181 3 salt salt NN cord-276598-tm0yj2sn 181 4 elimination elimination NN cord-276598-tm0yj2sn 181 5 route route NN cord-276598-tm0yj2sn 181 6 , , , cord-276598-tm0yj2sn 181 7 this this DT cord-276598-tm0yj2sn 181 8 time time NN cord-276598-tm0yj2sn 181 9 using use VBG cord-276598-tm0yj2sn 181 10 inorganic inorganic JJ cord-276598-tm0yj2sn 181 11 bases basis NNS cord-276598-tm0yj2sn 181 12 and and CC cord-276598-tm0yj2sn 181 13 [ [ -LRB- cord-276598-tm0yj2sn 181 14 n n NNP cord-276598-tm0yj2sn 181 15 - - HYPH cord-276598-tm0yj2sn 181 16 Bu Bu NNP cord-276598-tm0yj2sn 181 17 4 4 CD cord-276598-tm0yj2sn 181 18 N]Br N]Br NNP cord-276598-tm0yj2sn 181 19 as as IN cord-276598-tm0yj2sn 181 20 a a DT cord-276598-tm0yj2sn 181 21 catalyst catalyst NN cord-276598-tm0yj2sn 181 22 , , , cord-276598-tm0yj2sn 181 23 Zwierzak Zwierzak NNP cord-276598-tm0yj2sn 181 24 and and CC cord-276598-tm0yj2sn 181 25 Osowska Osowska NNP cord-276598-tm0yj2sn 181 26 - - HYPH cord-276598-tm0yj2sn 181 27 Pacewicka Pacewicka NNP cord-276598-tm0yj2sn 181 28 synthesized synthesize VBD cord-276598-tm0yj2sn 181 29 P P NNP cord-276598-tm0yj2sn 181 30 - - HYPH cord-276598-tm0yj2sn 181 31 Ns Ns NNP cord-276598-tm0yj2sn 181 32 from from IN cord-276598-tm0yj2sn 181 33 ( ( -LRB- cord-276598-tm0yj2sn 181 34 EtO EtO NNP cord-276598-tm0yj2sn 181 35 ) ) -RRB- cord-276598-tm0yj2sn 181 36 2 2 CD cord-276598-tm0yj2sn 181 37 P(O)H P(O)H NNP cord-276598-tm0yj2sn 181 38 ( ( -LRB- cord-276598-tm0yj2sn 181 39 diethyl diethyl NNP cord-276598-tm0yj2sn 181 40 H H NNP cord-276598-tm0yj2sn 181 41 - - HYPH cord-276598-tm0yj2sn 181 42 P P NNP cord-276598-tm0yj2sn 181 43 ) ) -RRB- cord-276598-tm0yj2sn 181 44 and and CC cord-276598-tm0yj2sn 181 45 various various JJ cord-276598-tm0yj2sn 181 46 amines amine NNS cord-276598-tm0yj2sn 181 47 ( ( -LRB- cord-276598-tm0yj2sn 181 48 Scheme scheme NN cord-276598-tm0yj2sn 181 49 5a 5a CD cord-276598-tm0yj2sn 181 50 ) ) -RRB- cord-276598-tm0yj2sn 182 1 [ [ -LRB- cord-276598-tm0yj2sn 182 2 89 89 CD cord-276598-tm0yj2sn 182 3 ] ] -RRB- cord-276598-tm0yj2sn 182 4 . . . cord-276598-tm0yj2sn 183 1 Aromatic aromatic JJ cord-276598-tm0yj2sn 183 2 amines amine NNS cord-276598-tm0yj2sn 183 3 such such JJ cord-276598-tm0yj2sn 183 4 as as IN cord-276598-tm0yj2sn 183 5 aniline aniline NN cord-276598-tm0yj2sn 183 6 and and CC cord-276598-tm0yj2sn 183 7 4-chloroaniline 4-chloroaniline CD cord-276598-tm0yj2sn 183 8 , , , cord-276598-tm0yj2sn 183 9 aliphatic aliphatic JJ cord-276598-tm0yj2sn 183 10 amines amine NNS cord-276598-tm0yj2sn 183 11 such such JJ cord-276598-tm0yj2sn 183 12 as as IN cord-276598-tm0yj2sn 183 13 cyclohexylamine cyclohexylamine NNP cord-276598-tm0yj2sn 183 14 , , , cord-276598-tm0yj2sn 183 15 n n JJ cord-276598-tm0yj2sn 183 16 - - HYPH cord-276598-tm0yj2sn 183 17 butylamine butylamine NNP cord-276598-tm0yj2sn 183 18 , , , cord-276598-tm0yj2sn 183 19 and and CC cord-276598-tm0yj2sn 183 20 ethanamine ethanamine NN cord-276598-tm0yj2sn 183 21 , , , cord-276598-tm0yj2sn 183 22 and and CC cord-276598-tm0yj2sn 183 23 alkanolamines alkanolamine NNS cord-276598-tm0yj2sn 183 24 such such JJ cord-276598-tm0yj2sn 183 25 as as IN cord-276598-tm0yj2sn 183 26 2-aminoethan-1-ol 2-aminoethan-1-ol CD cord-276598-tm0yj2sn 183 27 , , , cord-276598-tm0yj2sn 183 28 3-aminopropan-1-ol 3-aminopropan-1-ol CD cord-276598-tm0yj2sn 183 29 , , , cord-276598-tm0yj2sn 183 30 and and CC cord-276598-tm0yj2sn 184 1 bis(2-(-ethoxy)ethyl)amine bis(2-(-ethoxy)ethyl)amine NNP cord-276598-tm0yj2sn 184 2 were be VBD cord-276598-tm0yj2sn 184 3 explored explore VBN cord-276598-tm0yj2sn 184 4 to to TO cord-276598-tm0yj2sn 184 5 demonstrate demonstrate VB cord-276598-tm0yj2sn 184 6 the the DT cord-276598-tm0yj2sn 184 7 broad broad JJ cord-276598-tm0yj2sn 184 8 scope scope NN cord-276598-tm0yj2sn 184 9 of of IN cord-276598-tm0yj2sn 184 10 this this DT cord-276598-tm0yj2sn 184 11 synthetic synthetic JJ cord-276598-tm0yj2sn 184 12 transformation transformation NN cord-276598-tm0yj2sn 184 13 . . . cord-276598-tm0yj2sn 185 1 The the DT cord-276598-tm0yj2sn 185 2 P P NNP cord-276598-tm0yj2sn 185 3 - - HYPH cord-276598-tm0yj2sn 185 4 Ns Ns NNP cord-276598-tm0yj2sn 185 5 were be VBD cord-276598-tm0yj2sn 185 6 isolated isolate VBN cord-276598-tm0yj2sn 185 7 in in IN cord-276598-tm0yj2sn 185 8 83 83 CD cord-276598-tm0yj2sn 185 9 - - SYM cord-276598-tm0yj2sn 185 10 100 100 CD cord-276598-tm0yj2sn 185 11 % % NN cord-276598-tm0yj2sn 185 12 yield yield NN cord-276598-tm0yj2sn 185 13 after after IN cord-276598-tm0yj2sn 185 14 recrystallization recrystallization NN cord-276598-tm0yj2sn 185 15 . . . cord-276598-tm0yj2sn 186 1 In in IN cord-276598-tm0yj2sn 186 2 a a DT cord-276598-tm0yj2sn 186 3 similar similar JJ cord-276598-tm0yj2sn 186 4 synthesis synthesis NN cord-276598-tm0yj2sn 186 5 , , , cord-276598-tm0yj2sn 186 6 using use VBG cord-276598-tm0yj2sn 186 7 [ [ -LRB- cord-276598-tm0yj2sn 186 8 BnEt BnEt NNP cord-276598-tm0yj2sn 186 9 3 3 CD cord-276598-tm0yj2sn 186 10 N]Cl N]Cl NNP cord-276598-tm0yj2sn 186 11 as as IN cord-276598-tm0yj2sn 186 12 the the DT cord-276598-tm0yj2sn 186 13 catalyst catalyst NN cord-276598-tm0yj2sn 186 14 instead instead RB cord-276598-tm0yj2sn 186 15 of of IN cord-276598-tm0yj2sn 186 16 [ [ -LRB- cord-276598-tm0yj2sn 186 17 n n NNP cord-276598-tm0yj2sn 186 18 - - HYPH cord-276598-tm0yj2sn 186 19 Bu Bu NNP cord-276598-tm0yj2sn 186 20 4 4 CD cord-276598-tm0yj2sn 186 21 N]Br N]Br NNP cord-276598-tm0yj2sn 186 22 , , , cord-276598-tm0yj2sn 186 23 Zwierzak Zwierzak NNP cord-276598-tm0yj2sn 186 24 accomplished accomplish VBD cord-276598-tm0yj2sn 186 25 the the DT cord-276598-tm0yj2sn 186 26 phosphorylation phosphorylation NN cord-276598-tm0yj2sn 186 27 of of IN cord-276598-tm0yj2sn 186 28 amines amine NNS cord-276598-tm0yj2sn 186 29 using use VBG cord-276598-tm0yj2sn 186 30 dialkyl dialkyl NNP cord-276598-tm0yj2sn 186 31 H H NNP cord-276598-tm0yj2sn 186 32 - - HYPH cord-276598-tm0yj2sn 186 33 phosphonate phosphonate NNP cord-276598-tm0yj2sn 187 1 ( ( -LRB- cord-276598-tm0yj2sn 187 2 RO RO NNP cord-276598-tm0yj2sn 187 3 ) ) -RRB- cord-276598-tm0yj2sn 187 4 2 2 CD cord-276598-tm0yj2sn 187 5 P(O)H p(o)h NN cord-276598-tm0yj2sn 188 1 ( ( -LRB- cord-276598-tm0yj2sn 188 2 R r NN cord-276598-tm0yj2sn 188 3 = = FW cord-276598-tm0yj2sn 188 4 Et Et NNP cord-276598-tm0yj2sn 188 5 , , , cord-276598-tm0yj2sn 188 6 Bn Bn NNP cord-276598-tm0yj2sn 188 7 , , , cord-276598-tm0yj2sn 188 8 t t NN cord-276598-tm0yj2sn 188 9 - - HYPH cord-276598-tm0yj2sn 188 10 Bu Bu NNP cord-276598-tm0yj2sn 188 11 ; ; : cord-276598-tm0yj2sn 188 12 Scheme scheme NN cord-276598-tm0yj2sn 188 13 5b 5b CD cord-276598-tm0yj2sn 188 14 ) ) -RRB- cord-276598-tm0yj2sn 189 1 [ [ -LRB- cord-276598-tm0yj2sn 189 2 87 87 CD cord-276598-tm0yj2sn 189 3 ] ] -RRB- cord-276598-tm0yj2sn 189 4 . . . cord-276598-tm0yj2sn 190 1 A a DT cord-276598-tm0yj2sn 190 2 range range NN cord-276598-tm0yj2sn 190 3 of of IN cord-276598-tm0yj2sn 190 4 amines amine NNS cord-276598-tm0yj2sn 190 5 , , , cord-276598-tm0yj2sn 190 6 such such JJ cord-276598-tm0yj2sn 190 7 as as IN cord-276598-tm0yj2sn 190 8 aniline aniline NN cord-276598-tm0yj2sn 190 9 , , , cord-276598-tm0yj2sn 190 10 benzylamine benzylamine JJ cord-276598-tm0yj2sn 190 11 , , , cord-276598-tm0yj2sn 190 12 cyclohexylamine cyclohexylamine NNP cord-276598-tm0yj2sn 190 13 , , , cord-276598-tm0yj2sn 190 14 ethylamine ethylamine NNP cord-276598-tm0yj2sn 190 15 , , , cord-276598-tm0yj2sn 190 16 and and CC cord-276598-tm0yj2sn 190 17 diethylamine diethylamine NN cord-276598-tm0yj2sn 190 18 were be VBD cord-276598-tm0yj2sn 190 19 used use VBN cord-276598-tm0yj2sn 190 20 . . . cord-276598-tm0yj2sn 191 1 The the DT cord-276598-tm0yj2sn 191 2 crude crude NN cord-276598-tm0yj2sn 191 3 P p NN cord-276598-tm0yj2sn 191 4 - - HYPH cord-276598-tm0yj2sn 191 5 Ns Ns NNP cord-276598-tm0yj2sn 191 6 were be VBD cord-276598-tm0yj2sn 191 7 recrystallized recrystallize VBN cord-276598-tm0yj2sn 191 8 to to TO cord-276598-tm0yj2sn 191 9 afford afford VB cord-276598-tm0yj2sn 191 10 pure pure JJ cord-276598-tm0yj2sn 191 11 products product NNS cord-276598-tm0yj2sn 191 12 in in IN cord-276598-tm0yj2sn 191 13 35 35 CD cord-276598-tm0yj2sn 191 14 - - SYM cord-276598-tm0yj2sn 191 15 93 93 CD cord-276598-tm0yj2sn 191 16 % % NN cord-276598-tm0yj2sn 191 17 yield yield NN cord-276598-tm0yj2sn 191 18 . . . cord-276598-tm0yj2sn 192 1 Due due IN cord-276598-tm0yj2sn 192 2 to to IN cord-276598-tm0yj2sn 192 3 the the DT cord-276598-tm0yj2sn 192 4 difficulty difficulty NN cord-276598-tm0yj2sn 192 5 encountered encounter VBN cord-276598-tm0yj2sn 192 6 in in IN cord-276598-tm0yj2sn 192 7 phosphorylating phosphorylate VBG cord-276598-tm0yj2sn 192 8 aromatic aromatic JJ cord-276598-tm0yj2sn 192 9 amines amine NNS cord-276598-tm0yj2sn 192 10 , , , cord-276598-tm0yj2sn 192 11 as as IN cord-276598-tm0yj2sn 192 12 mentioned mention VBN cord-276598-tm0yj2sn 192 13 by by IN cord-276598-tm0yj2sn 192 14 Zwierzak Zwierzak NNP cord-276598-tm0yj2sn 192 15 [ [ -LRB- cord-276598-tm0yj2sn 192 16 87 87 CD cord-276598-tm0yj2sn 192 17 , , , cord-276598-tm0yj2sn 192 18 89 89 CD cord-276598-tm0yj2sn 192 19 ] ] -RRB- cord-276598-tm0yj2sn 192 20 , , , cord-276598-tm0yj2sn 192 21 Lukanov Lukanov NNP cord-276598-tm0yj2sn 192 22 et et NNP cord-276598-tm0yj2sn 192 23 al al NNP cord-276598-tm0yj2sn 192 24 . . NNP cord-276598-tm0yj2sn 192 25 proposed propose VBD cord-276598-tm0yj2sn 192 26 a a DT cord-276598-tm0yj2sn 192 27 similar similar JJ cord-276598-tm0yj2sn 192 28 synthetic synthetic JJ cord-276598-tm0yj2sn 192 29 route route NN cord-276598-tm0yj2sn 192 30 using use VBG cord-276598-tm0yj2sn 192 31 N n NN cord-276598-tm0yj2sn 192 32 - - HYPH cord-276598-tm0yj2sn 192 33 phenylformamide phenylformamide NN cord-276598-tm0yj2sn 192 34 or or CC cord-276598-tm0yj2sn 192 35 2-chloro 2-chloro CD cord-276598-tm0yj2sn 192 36 - - HYPH cord-276598-tm0yj2sn 192 37 N n NN cord-276598-tm0yj2sn 192 38 - - HYPH cord-276598-tm0yj2sn 192 39 phenylacetamide phenylacetamide NN cord-276598-tm0yj2sn 192 40 as as IN cord-276598-tm0yj2sn 192 41 the the DT cord-276598-tm0yj2sn 192 42 N n CD cord-276598-tm0yj2sn 192 43 - - HYPH cord-276598-tm0yj2sn 192 44 source source NN cord-276598-tm0yj2sn 192 45 , , , cord-276598-tm0yj2sn 192 46 which which WDT cord-276598-tm0yj2sn 192 47 offered offer VBD cord-276598-tm0yj2sn 192 48 less less JJR cord-276598-tm0yj2sn 192 49 steric steric JJ cord-276598-tm0yj2sn 192 50 hindrance hindrance NN cord-276598-tm0yj2sn 192 51 and and CC cord-276598-tm0yj2sn 192 52 better well JJR cord-276598-tm0yj2sn 192 53 N n CD cord-276598-tm0yj2sn 192 54 - - HYPH cord-276598-tm0yj2sn 192 55 H h NN cord-276598-tm0yj2sn 192 56 acidity acidity NN cord-276598-tm0yj2sn 192 57 ( ( -LRB- cord-276598-tm0yj2sn 192 58 Scheme scheme NN cord-276598-tm0yj2sn 192 59 5c 5c CD cord-276598-tm0yj2sn 192 60 ) ) -RRB- cord-276598-tm0yj2sn 192 61 [ [ -LRB- cord-276598-tm0yj2sn 192 62 96 96 CD cord-276598-tm0yj2sn 192 63 ] ] -RRB- cord-276598-tm0yj2sn 192 64 . . . cord-276598-tm0yj2sn 193 1 Derivatives derivative NNS cord-276598-tm0yj2sn 193 2 of of IN cord-276598-tm0yj2sn 193 3 N n NN cord-276598-tm0yj2sn 193 4 - - HYPH cord-276598-tm0yj2sn 193 5 phenylformamide phenylformamide NN cord-276598-tm0yj2sn 193 6 or or CC cord-276598-tm0yj2sn 193 7 2-chloro 2-chloro CD cord-276598-tm0yj2sn 193 8 - - HYPH cord-276598-tm0yj2sn 193 9 N n CD cord-276598-tm0yj2sn 193 10 - - HYPH cord-276598-tm0yj2sn 193 11 phenylacetamide phenylacetamide NN cord-276598-tm0yj2sn 193 12 ( ( -LRB- cord-276598-tm0yj2sn 193 13 R'R"NC(O)R R'R"NC(O)R NNP cord-276598-tm0yj2sn 193 14 " " '' cord-276598-tm0yj2sn 193 15 ' ' '' cord-276598-tm0yj2sn 193 16 ) ) -RRB- cord-276598-tm0yj2sn 193 17 were be VBD cord-276598-tm0yj2sn 193 18 used use VBN cord-276598-tm0yj2sn 193 19 containing contain VBG cord-276598-tm0yj2sn 193 20 a a DT cord-276598-tm0yj2sn 193 21 wide wide JJ cord-276598-tm0yj2sn 193 22 range range NN cord-276598-tm0yj2sn 193 23 of of IN cord-276598-tm0yj2sn 193 24 aryl aryl NN cord-276598-tm0yj2sn 193 25 - - HYPH cord-276598-tm0yj2sn 193 26 substituents substituent NNS cord-276598-tm0yj2sn 193 27 ( ( -LRB- cord-276598-tm0yj2sn 193 28 e.g. e.g. RB cord-276598-tm0yj2sn 193 29 , , , cord-276598-tm0yj2sn 193 30 R r NN cord-276598-tm0yj2sn 193 31 " " '' cord-276598-tm0yj2sn 193 32 = = NFP cord-276598-tm0yj2sn 194 1 Ph Ph NNP cord-276598-tm0yj2sn 194 2 , , , cord-276598-tm0yj2sn 194 3 4-MeOPh 4-meoph CD cord-276598-tm0yj2sn 194 4 , , , cord-276598-tm0yj2sn 194 5 4-ClPh 4-clph CD cord-276598-tm0yj2sn 194 6 , , , cord-276598-tm0yj2sn 194 7 2-MeOPh 2-meoph CD cord-276598-tm0yj2sn 194 8 , , , cord-276598-tm0yj2sn 194 9 2,3-Cl 2,3-cl CD cord-276598-tm0yj2sn 194 10 2 2 CD cord-276598-tm0yj2sn 194 11 Ph Ph NNP cord-276598-tm0yj2sn 194 12 , , , cord-276598-tm0yj2sn 194 13 2-MePh 2-meph CD cord-276598-tm0yj2sn 194 14 , , , cord-276598-tm0yj2sn 194 15 and and CC cord-276598-tm0yj2sn 194 16 2,6-(C 2,6-(c CD cord-276598-tm0yj2sn 194 17 2 2 CD cord-276598-tm0yj2sn 194 18 H h NN cord-276598-tm0yj2sn 194 19 5 5 CD cord-276598-tm0yj2sn 194 20 ) ) -RRB- cord-276598-tm0yj2sn 194 21 2 2 CD cord-276598-tm0yj2sn 194 22 Ph Ph NNP cord-276598-tm0yj2sn 194 23 and and CC cord-276598-tm0yj2sn 194 24 2,6-(CH 2,6-(ch CD cord-276598-tm0yj2sn 194 25 3 3 CD cord-276598-tm0yj2sn 194 26 ) ) -RRB- cord-276598-tm0yj2sn 194 27 2 2 CD cord-276598-tm0yj2sn 194 28 Ph Ph NNP cord-276598-tm0yj2sn 194 29 ) ) -RRB- cord-276598-tm0yj2sn 194 30 . . . cord-276598-tm0yj2sn 195 1 Either either CC cord-276598-tm0yj2sn 195 2 column column NN cord-276598-tm0yj2sn 195 3 chromatography chromatography NN cord-276598-tm0yj2sn 195 4 ( ( -LRB- cord-276598-tm0yj2sn 195 5 on on IN cord-276598-tm0yj2sn 195 6 silica silica NN cord-276598-tm0yj2sn 195 7 ) ) -RRB- cord-276598-tm0yj2sn 195 8 or or CC cord-276598-tm0yj2sn 195 9 recrystallization recrystallization NN cord-276598-tm0yj2sn 195 10 were be VBD cord-276598-tm0yj2sn 195 11 used use VBN cord-276598-tm0yj2sn 195 12 to to TO cord-276598-tm0yj2sn 195 13 purify purify VB cord-276598-tm0yj2sn 195 14 the the DT cord-276598-tm0yj2sn 195 15 P P NNP cord-276598-tm0yj2sn 195 16 - - HYPH cord-276598-tm0yj2sn 195 17 Ns Ns NNP cord-276598-tm0yj2sn 195 18 to to TO cord-276598-tm0yj2sn 195 19 obtain obtain VB cord-276598-tm0yj2sn 195 20 isolated isolated JJ cord-276598-tm0yj2sn 195 21 yields yield NNS cord-276598-tm0yj2sn 195 22 in in IN cord-276598-tm0yj2sn 195 23 the the DT cord-276598-tm0yj2sn 195 24 range range NN cord-276598-tm0yj2sn 195 25 of of IN cord-276598-tm0yj2sn 195 26 30 30 CD cord-276598-tm0yj2sn 195 27 - - SYM cord-276598-tm0yj2sn 195 28 80 80 CD cord-276598-tm0yj2sn 195 29 % % NN cord-276598-tm0yj2sn 195 30 . . . cord-276598-tm0yj2sn 195 31 _SP cord-276598-tm0yj2sn 196 1 In in IN cord-276598-tm0yj2sn 196 2 another another DT cord-276598-tm0yj2sn 196 3 salt salt NN cord-276598-tm0yj2sn 196 4 elimination elimination NN cord-276598-tm0yj2sn 196 5 route route NN cord-276598-tm0yj2sn 196 6 , , , cord-276598-tm0yj2sn 196 7 this this DT cord-276598-tm0yj2sn 196 8 time time NN cord-276598-tm0yj2sn 196 9 using use VBG cord-276598-tm0yj2sn 196 10 inorganic inorganic JJ cord-276598-tm0yj2sn 196 11 bases basis NNS cord-276598-tm0yj2sn 196 12 and and CC cord-276598-tm0yj2sn 196 13 [ [ -LRB- cord-276598-tm0yj2sn 196 14 n n NN cord-276598-tm0yj2sn 196 15 - - HYPH cord-276598-tm0yj2sn 196 16 Bu4N]Br Bu4N]Br NNP cord-276598-tm0yj2sn 196 17 as as IN cord-276598-tm0yj2sn 196 18 a a DT cord-276598-tm0yj2sn 196 19 catalyst catalyst NN cord-276598-tm0yj2sn 196 20 , , , cord-276598-tm0yj2sn 196 21 Zwierzak Zwierzak NNP cord-276598-tm0yj2sn 196 22 and and CC cord-276598-tm0yj2sn 196 23 Osowska Osowska NNP cord-276598-tm0yj2sn 196 24 - - HYPH cord-276598-tm0yj2sn 196 25 Pacewicka Pacewicka NNP cord-276598-tm0yj2sn 196 26 synthesized synthesize VBD cord-276598-tm0yj2sn 196 27 P P NNP cord-276598-tm0yj2sn 196 28 - - HYPH cord-276598-tm0yj2sn 196 29 Ns Ns NNP cord-276598-tm0yj2sn 196 30 from from IN cord-276598-tm0yj2sn 196 31 ( ( -LRB- cord-276598-tm0yj2sn 196 32 EtO)2P(O)H EtO)2P(O)H NNP cord-276598-tm0yj2sn 196 33 ( ( -LRB- cord-276598-tm0yj2sn 196 34 diethyl diethyl NNP cord-276598-tm0yj2sn 196 35 H H NNP cord-276598-tm0yj2sn 196 36 - - HYPH cord-276598-tm0yj2sn 196 37 P P NNP cord-276598-tm0yj2sn 196 38 ) ) -RRB- cord-276598-tm0yj2sn 196 39 and and CC cord-276598-tm0yj2sn 196 40 various various JJ cord-276598-tm0yj2sn 196 41 amines amine NNS cord-276598-tm0yj2sn 196 42 ( ( -LRB- cord-276598-tm0yj2sn 196 43 Scheme scheme NN cord-276598-tm0yj2sn 196 44 5a 5a CD cord-276598-tm0yj2sn 196 45 ) ) -RRB- cord-276598-tm0yj2sn 196 46 [ [ -LRB- cord-276598-tm0yj2sn 196 47 89 89 CD cord-276598-tm0yj2sn 196 48 ] ] -RRB- cord-276598-tm0yj2sn 196 49 . . . cord-276598-tm0yj2sn 197 1 Aromatic aromatic JJ cord-276598-tm0yj2sn 197 2 amines amine NNS cord-276598-tm0yj2sn 197 3 such such JJ cord-276598-tm0yj2sn 197 4 as as IN cord-276598-tm0yj2sn 197 5 aniline aniline NN cord-276598-tm0yj2sn 197 6 and and CC cord-276598-tm0yj2sn 197 7 4-chloroaniline 4-chloroaniline CD cord-276598-tm0yj2sn 197 8 , , , cord-276598-tm0yj2sn 197 9 aliphatic aliphatic JJ cord-276598-tm0yj2sn 197 10 amines amine NNS cord-276598-tm0yj2sn 197 11 such such JJ cord-276598-tm0yj2sn 197 12 as as IN cord-276598-tm0yj2sn 197 13 cyclohexylamine cyclohexylamine NNP cord-276598-tm0yj2sn 197 14 , , , cord-276598-tm0yj2sn 197 15 n n JJ cord-276598-tm0yj2sn 197 16 - - HYPH cord-276598-tm0yj2sn 197 17 butylamine butylamine NNP cord-276598-tm0yj2sn 197 18 , , , cord-276598-tm0yj2sn 197 19 and and CC cord-276598-tm0yj2sn 197 20 ethanamine ethanamine NN cord-276598-tm0yj2sn 197 21 , , , cord-276598-tm0yj2sn 197 22 and and CC cord-276598-tm0yj2sn 197 23 alkanolamines alkanolamine NNS cord-276598-tm0yj2sn 197 24 such such JJ cord-276598-tm0yj2sn 197 25 as as IN cord-276598-tm0yj2sn 197 26 2-aminoethan-1-ol 2-aminoethan-1-ol CD cord-276598-tm0yj2sn 197 27 , , , cord-276598-tm0yj2sn 197 28 3-aminopropan-1-ol 3-aminopropan-1-ol CD cord-276598-tm0yj2sn 197 29 , , , cord-276598-tm0yj2sn 197 30 and and CC cord-276598-tm0yj2sn 198 1 bis(2-(-ethoxy)ethyl)amine bis(2-(-ethoxy)ethyl)amine NNP cord-276598-tm0yj2sn 198 2 were be VBD cord-276598-tm0yj2sn 198 3 explored explore VBN cord-276598-tm0yj2sn 198 4 to to TO cord-276598-tm0yj2sn 198 5 demonstrate demonstrate VB cord-276598-tm0yj2sn 198 6 the the DT cord-276598-tm0yj2sn 198 7 broad broad JJ cord-276598-tm0yj2sn 198 8 scope scope NN cord-276598-tm0yj2sn 198 9 of of IN cord-276598-tm0yj2sn 198 10 this this DT cord-276598-tm0yj2sn 198 11 synthetic synthetic JJ cord-276598-tm0yj2sn 198 12 transformation transformation NN cord-276598-tm0yj2sn 198 13 . . . cord-276598-tm0yj2sn 199 1 The the DT cord-276598-tm0yj2sn 199 2 P P NNP cord-276598-tm0yj2sn 199 3 - - HYPH cord-276598-tm0yj2sn 199 4 Ns Ns NNP cord-276598-tm0yj2sn 199 5 were be VBD cord-276598-tm0yj2sn 199 6 isolated isolate VBN cord-276598-tm0yj2sn 199 7 in in IN cord-276598-tm0yj2sn 199 8 83 83 CD cord-276598-tm0yj2sn 199 9 - - SYM cord-276598-tm0yj2sn 199 10 100 100 CD cord-276598-tm0yj2sn 199 11 % % NN cord-276598-tm0yj2sn 199 12 yield yield NN cord-276598-tm0yj2sn 199 13 after after IN cord-276598-tm0yj2sn 199 14 recrystallization recrystallization NN cord-276598-tm0yj2sn 199 15 . . . cord-276598-tm0yj2sn 200 1 In in IN cord-276598-tm0yj2sn 200 2 a a DT cord-276598-tm0yj2sn 200 3 similar similar JJ cord-276598-tm0yj2sn 200 4 synthesis synthesis NN cord-276598-tm0yj2sn 200 5 , , , cord-276598-tm0yj2sn 200 6 using use VBG cord-276598-tm0yj2sn 200 7 [ [ -LRB- cord-276598-tm0yj2sn 200 8 BnEt3N]Cl BnEt3N]Cl NNP cord-276598-tm0yj2sn 200 9 as as IN cord-276598-tm0yj2sn 200 10 the the DT cord-276598-tm0yj2sn 200 11 catalyst catalyst NN cord-276598-tm0yj2sn 200 12 instead instead RB cord-276598-tm0yj2sn 200 13 of of IN cord-276598-tm0yj2sn 200 14 [ [ -LRB- cord-276598-tm0yj2sn 200 15 n n NNP cord-276598-tm0yj2sn 200 16 - - HYPH cord-276598-tm0yj2sn 200 17 Bu4N]Br Bu4N]Br NNP cord-276598-tm0yj2sn 200 18 , , , cord-276598-tm0yj2sn 200 19 Zwierzak Zwierzak NNP cord-276598-tm0yj2sn 200 20 accomplished accomplish VBD cord-276598-tm0yj2sn 200 21 the the DT cord-276598-tm0yj2sn 200 22 phosphorylation phosphorylation NN cord-276598-tm0yj2sn 200 23 of of IN cord-276598-tm0yj2sn 200 24 amines amine NNS cord-276598-tm0yj2sn 200 25 using use VBG cord-276598-tm0yj2sn 200 26 dialkyl dialkyl NNP cord-276598-tm0yj2sn 200 27 H H NNP cord-276598-tm0yj2sn 200 28 - - HYPH cord-276598-tm0yj2sn 200 29 phosphonate phosphonate NNP cord-276598-tm0yj2sn 201 1 ( ( -LRB- cord-276598-tm0yj2sn 201 2 RO)2P(O)H RO)2P(O)H NNP cord-276598-tm0yj2sn 201 3 ( ( -LRB- cord-276598-tm0yj2sn 201 4 R r NN cord-276598-tm0yj2sn 201 5 = = FW cord-276598-tm0yj2sn 201 6 Et et NN cord-276598-tm0yj2sn 201 7 , , , cord-276598-tm0yj2sn 202 1 Bn Bn NNP cord-276598-tm0yj2sn 202 2 , , , cord-276598-tm0yj2sn 202 3 t t NN cord-276598-tm0yj2sn 202 4 - - HYPH cord-276598-tm0yj2sn 202 5 Bu Bu NNP cord-276598-tm0yj2sn 202 6 ; ; : cord-276598-tm0yj2sn 202 7 Scheme scheme NN cord-276598-tm0yj2sn 202 8 5b 5b CD cord-276598-tm0yj2sn 202 9 ) ) -RRB- cord-276598-tm0yj2sn 203 1 [ [ -LRB- cord-276598-tm0yj2sn 203 2 87 87 CD cord-276598-tm0yj2sn 203 3 ] ] -RRB- cord-276598-tm0yj2sn 203 4 . . . cord-276598-tm0yj2sn 204 1 A a DT cord-276598-tm0yj2sn 204 2 range range NN cord-276598-tm0yj2sn 204 3 of of IN cord-276598-tm0yj2sn 204 4 amines amine NNS cord-276598-tm0yj2sn 204 5 , , , cord-276598-tm0yj2sn 204 6 such such JJ cord-276598-tm0yj2sn 204 7 as as IN cord-276598-tm0yj2sn 204 8 aniline aniline NN cord-276598-tm0yj2sn 204 9 , , , cord-276598-tm0yj2sn 204 10 benzylamine benzylamine JJ cord-276598-tm0yj2sn 204 11 , , , cord-276598-tm0yj2sn 204 12 cyclohexylamine cyclohexylamine NNP cord-276598-tm0yj2sn 204 13 , , , cord-276598-tm0yj2sn 204 14 ethylamine ethylamine NNP cord-276598-tm0yj2sn 204 15 , , , cord-276598-tm0yj2sn 204 16 and and CC cord-276598-tm0yj2sn 204 17 diethylamine diethylamine NN cord-276598-tm0yj2sn 204 18 were be VBD cord-276598-tm0yj2sn 204 19 used use VBN cord-276598-tm0yj2sn 204 20 . . . cord-276598-tm0yj2sn 205 1 The the DT cord-276598-tm0yj2sn 205 2 crude crude NN cord-276598-tm0yj2sn 205 3 P p NN cord-276598-tm0yj2sn 205 4 - - HYPH cord-276598-tm0yj2sn 205 5 Ns Ns NNP cord-276598-tm0yj2sn 205 6 were be VBD cord-276598-tm0yj2sn 205 7 recrystallized recrystallize VBN cord-276598-tm0yj2sn 205 8 to to TO cord-276598-tm0yj2sn 205 9 afford afford VB cord-276598-tm0yj2sn 205 10 pure pure JJ cord-276598-tm0yj2sn 205 11 products product NNS cord-276598-tm0yj2sn 205 12 in in IN cord-276598-tm0yj2sn 205 13 35 35 CD cord-276598-tm0yj2sn 205 14 - - SYM cord-276598-tm0yj2sn 205 15 93 93 CD cord-276598-tm0yj2sn 205 16 % % NN cord-276598-tm0yj2sn 205 17 yield yield NN cord-276598-tm0yj2sn 205 18 . . . cord-276598-tm0yj2sn 206 1 Due due IN cord-276598-tm0yj2sn 206 2 to to IN cord-276598-tm0yj2sn 206 3 the the DT cord-276598-tm0yj2sn 206 4 difficulty difficulty NN cord-276598-tm0yj2sn 206 5 encountered encounter VBN cord-276598-tm0yj2sn 206 6 in in IN cord-276598-tm0yj2sn 206 7 phosphorylating phosphorylate VBG cord-276598-tm0yj2sn 206 8 aromatic aromatic JJ cord-276598-tm0yj2sn 206 9 amines amine NNS cord-276598-tm0yj2sn 206 10 , , , cord-276598-tm0yj2sn 206 11 as as IN cord-276598-tm0yj2sn 206 12 mentioned mention VBN cord-276598-tm0yj2sn 206 13 by by IN cord-276598-tm0yj2sn 206 14 Zwierzak Zwierzak NNP cord-276598-tm0yj2sn 206 15 [ [ -LRB- cord-276598-tm0yj2sn 206 16 87 87 CD cord-276598-tm0yj2sn 206 17 , , , cord-276598-tm0yj2sn 206 18 89 89 CD cord-276598-tm0yj2sn 206 19 ] ] -RRB- cord-276598-tm0yj2sn 206 20 , , , cord-276598-tm0yj2sn 206 21 Lukanov Lukanov NNP cord-276598-tm0yj2sn 206 22 et et NNP cord-276598-tm0yj2sn 206 23 al al NNP cord-276598-tm0yj2sn 206 24 . . NNP cord-276598-tm0yj2sn 206 25 proposed propose VBD cord-276598-tm0yj2sn 206 26 a a DT cord-276598-tm0yj2sn 206 27 similar similar JJ cord-276598-tm0yj2sn 206 28 synthetic synthetic JJ cord-276598-tm0yj2sn 206 29 route route NN cord-276598-tm0yj2sn 206 30 using use VBG cord-276598-tm0yj2sn 206 31 N n NN cord-276598-tm0yj2sn 206 32 - - HYPH cord-276598-tm0yj2sn 206 33 phenylformamide phenylformamide NN cord-276598-tm0yj2sn 206 34 or or CC cord-276598-tm0yj2sn 206 35 2-chloro 2-chloro CD cord-276598-tm0yj2sn 206 36 - - HYPH cord-276598-tm0yj2sn 206 37 N n NN cord-276598-tm0yj2sn 206 38 - - HYPH cord-276598-tm0yj2sn 206 39 phenylacetamide phenylacetamide NN cord-276598-tm0yj2sn 206 40 as as IN cord-276598-tm0yj2sn 206 41 the the DT cord-276598-tm0yj2sn 206 42 N n CD cord-276598-tm0yj2sn 206 43 - - HYPH cord-276598-tm0yj2sn 206 44 source source NN cord-276598-tm0yj2sn 206 45 , , , cord-276598-tm0yj2sn 206 46 which which WDT cord-276598-tm0yj2sn 206 47 offered offer VBD cord-276598-tm0yj2sn 206 48 less less JJR cord-276598-tm0yj2sn 206 49 steric steric JJ cord-276598-tm0yj2sn 206 50 hindrance hindrance NN cord-276598-tm0yj2sn 206 51 and and CC cord-276598-tm0yj2sn 206 52 better well JJR cord-276598-tm0yj2sn 206 53 N n CD cord-276598-tm0yj2sn 206 54 - - HYPH cord-276598-tm0yj2sn 206 55 H h NN cord-276598-tm0yj2sn 206 56 acidity acidity NN cord-276598-tm0yj2sn 206 57 ( ( -LRB- cord-276598-tm0yj2sn 206 58 Scheme scheme NN cord-276598-tm0yj2sn 206 59 5c 5c CD cord-276598-tm0yj2sn 206 60 ) ) -RRB- cord-276598-tm0yj2sn 206 61 [ [ -LRB- cord-276598-tm0yj2sn 206 62 96 96 CD cord-276598-tm0yj2sn 206 63 ] ] -RRB- cord-276598-tm0yj2sn 206 64 . . . cord-276598-tm0yj2sn 207 1 Derivatives derivative NNS cord-276598-tm0yj2sn 207 2 of of IN cord-276598-tm0yj2sn 207 3 N n NN cord-276598-tm0yj2sn 207 4 - - HYPH cord-276598-tm0yj2sn 207 5 phenylformamide phenylformamide NN cord-276598-tm0yj2sn 207 6 or or CC cord-276598-tm0yj2sn 207 7 2-chloro 2-chloro CD cord-276598-tm0yj2sn 207 8 - - HYPH cord-276598-tm0yj2sn 207 9 N n CD cord-276598-tm0yj2sn 207 10 - - HYPH cord-276598-tm0yj2sn 207 11 phenylacetamide phenylacetamide NN cord-276598-tm0yj2sn 207 12 ( ( -LRB- cord-276598-tm0yj2sn 207 13 R'R''NC(O)R R'R''NC(O)R NNP cord-276598-tm0yj2sn 207 14 ' ' '' cord-276598-tm0yj2sn 207 15 ' ' '' cord-276598-tm0yj2sn 207 16 ' ' '' cord-276598-tm0yj2sn 207 17 ) ) -RRB- cord-276598-tm0yj2sn 207 18 were be VBD cord-276598-tm0yj2sn 207 19 used use VBN cord-276598-tm0yj2sn 207 20 containing contain VBG cord-276598-tm0yj2sn 207 21 a a DT cord-276598-tm0yj2sn 207 22 wide wide JJ cord-276598-tm0yj2sn 207 23 range range NN cord-276598-tm0yj2sn 207 24 of of IN cord-276598-tm0yj2sn 207 25 aryl aryl NN cord-276598-tm0yj2sn 207 26 - - HYPH cord-276598-tm0yj2sn 207 27 substituents substituent NNS cord-276598-tm0yj2sn 207 28 ( ( -LRB- cord-276598-tm0yj2sn 207 29 e.g. e.g. RB cord-276598-tm0yj2sn 207 30 , , , cord-276598-tm0yj2sn 207 31 R r NN cord-276598-tm0yj2sn 207 32 ' ' '' cord-276598-tm0yj2sn 207 33 ' ' '' cord-276598-tm0yj2sn 207 34 = = NFP cord-276598-tm0yj2sn 208 1 Ph Ph NNP cord-276598-tm0yj2sn 208 2 , , , cord-276598-tm0yj2sn 208 3 4-MeOPh 4-meoph CD cord-276598-tm0yj2sn 208 4 , , , cord-276598-tm0yj2sn 208 5 4-ClPh 4-clph CD cord-276598-tm0yj2sn 208 6 , , , cord-276598-tm0yj2sn 208 7 2-MeOPh 2-meoph CD cord-276598-tm0yj2sn 208 8 , , , cord-276598-tm0yj2sn 208 9 2,3-Cl2Ph 2,3-cl2ph CD cord-276598-tm0yj2sn 208 10 , , , cord-276598-tm0yj2sn 208 11 2-MePh 2-meph CD cord-276598-tm0yj2sn 208 12 , , , cord-276598-tm0yj2sn 208 13 and and CC cord-276598-tm0yj2sn 208 14 2,6-(C2H5)2Ph 2,6-(c2h5)2ph CD cord-276598-tm0yj2sn 208 15 and and CC cord-276598-tm0yj2sn 208 16 2,6-(CH3)2Ph 2,6-(ch3)2ph CD cord-276598-tm0yj2sn 208 17 ) ) -RRB- cord-276598-tm0yj2sn 208 18 . . . cord-276598-tm0yj2sn 209 1 Either either CC cord-276598-tm0yj2sn 209 2 column column NN cord-276598-tm0yj2sn 209 3 chromatography chromatography NN cord-276598-tm0yj2sn 209 4 ( ( -LRB- cord-276598-tm0yj2sn 209 5 on on IN cord-276598-tm0yj2sn 209 6 silica silica NN cord-276598-tm0yj2sn 209 7 ) ) -RRB- cord-276598-tm0yj2sn 209 8 or or CC cord-276598-tm0yj2sn 209 9 recrystallization recrystallization NN cord-276598-tm0yj2sn 209 10 were be VBD cord-276598-tm0yj2sn 209 11 used use VBN cord-276598-tm0yj2sn 209 12 to to TO cord-276598-tm0yj2sn 209 13 purify purify VB cord-276598-tm0yj2sn 209 14 the the DT cord-276598-tm0yj2sn 209 15 P P NNP cord-276598-tm0yj2sn 209 16 - - HYPH cord-276598-tm0yj2sn 209 17 Ns Ns NNP cord-276598-tm0yj2sn 209 18 to to TO cord-276598-tm0yj2sn 209 19 obtain obtain VB cord-276598-tm0yj2sn 209 20 isolated isolated JJ cord-276598-tm0yj2sn 209 21 yields yield NNS cord-276598-tm0yj2sn 209 22 in in IN cord-276598-tm0yj2sn 209 23 the the DT cord-276598-tm0yj2sn 209 24 range range NN cord-276598-tm0yj2sn 209 25 of of IN cord-276598-tm0yj2sn 209 26 30 30 CD cord-276598-tm0yj2sn 209 27 - - SYM cord-276598-tm0yj2sn 209 28 80 80 CD cord-276598-tm0yj2sn 209 29 % % NN cord-276598-tm0yj2sn 209 30 . . . cord-276598-tm0yj2sn 210 1 Inorganic inorganic JJ cord-276598-tm0yj2sn 210 2 salt salt NN cord-276598-tm0yj2sn 210 3 elimination elimination NN cord-276598-tm0yj2sn 210 4 methods method NNS cord-276598-tm0yj2sn 210 5 stimulated stimulate VBD cord-276598-tm0yj2sn 210 6 an an DT cord-276598-tm0yj2sn 210 7 era era NN cord-276598-tm0yj2sn 210 8 of of IN cord-276598-tm0yj2sn 210 9 catalytic catalytic JJ cord-276598-tm0yj2sn 210 10 transformations transformation NNS cord-276598-tm0yj2sn 210 11 of of IN cord-276598-tm0yj2sn 210 12 dialkyl dialkyl NN cord-276598-tm0yj2sn 210 13 H H NNP cord-276598-tm0yj2sn 210 14 - - HYPH cord-276598-tm0yj2sn 210 15 P p NN cord-276598-tm0yj2sn 210 16 ( ( -LRB- cord-276598-tm0yj2sn 210 17 ( ( -LRB- cord-276598-tm0yj2sn 210 18 RO RO NNP cord-276598-tm0yj2sn 210 19 ) ) -RRB- cord-276598-tm0yj2sn 210 20 2 2 CD cord-276598-tm0yj2sn 210 21 P(O)H p(o)h NN cord-276598-tm0yj2sn 210 22 ; ; : cord-276598-tm0yj2sn 210 23 R r NN cord-276598-tm0yj2sn 210 24 = = NN cord-276598-tm0yj2sn 210 25 alkyl alkyl NN cord-276598-tm0yj2sn 210 26 ) ) -RRB- cord-276598-tm0yj2sn 210 27 to to IN cord-276598-tm0yj2sn 210 28 ( ( -LRB- cord-276598-tm0yj2sn 210 29 RO RO NNP cord-276598-tm0yj2sn 210 30 ) ) -RRB- cord-276598-tm0yj2sn 210 31 2 2 CD cord-276598-tm0yj2sn 211 1 P(O)Cl P(O)Cl VBN cord-276598-tm0yj2sn 212 1 ( ( -LRB- cord-276598-tm0yj2sn 212 2 dACP dacp JJ cord-276598-tm0yj2sn 212 3 ; ; : cord-276598-tm0yj2sn 212 4 R r NN cord-276598-tm0yj2sn 212 5 = = NN cord-276598-tm0yj2sn 212 6 alkyl alkyl NN cord-276598-tm0yj2sn 212 7 ) ) -RRB- cord-276598-tm0yj2sn 212 8 in in IN cord-276598-tm0yj2sn 212 9 the the DT cord-276598-tm0yj2sn 212 10 presence presence NN cord-276598-tm0yj2sn 212 11 of of IN cord-276598-tm0yj2sn 212 12 readily readily RB cord-276598-tm0yj2sn 212 13 available available JJ cord-276598-tm0yj2sn 212 14 inorganic inorganic JJ cord-276598-tm0yj2sn 212 15 bases basis NNS cord-276598-tm0yj2sn 212 16 , , , cord-276598-tm0yj2sn 212 17 thereby thereby RB cord-276598-tm0yj2sn 212 18 eliminating eliminate VBG cord-276598-tm0yj2sn 212 19 the the DT cord-276598-tm0yj2sn 212 20 use use NN cord-276598-tm0yj2sn 212 21 of of IN cord-276598-tm0yj2sn 212 22 Et Et NNP cord-276598-tm0yj2sn 212 23 3 3 CD cord-276598-tm0yj2sn 212 24 N. n. NN cord-276598-tm0yj2sn 213 1 However however RB cord-276598-tm0yj2sn 213 2 , , , cord-276598-tm0yj2sn 213 3 this this DT cord-276598-tm0yj2sn 213 4 method method NN cord-276598-tm0yj2sn 213 5 has have VBZ cord-276598-tm0yj2sn 213 6 limitations limitation NNS cord-276598-tm0yj2sn 213 7 including include VBG cord-276598-tm0yj2sn 213 8 a a DT cord-276598-tm0yj2sn 213 9 pre pre JJ cord-276598-tm0yj2sn 213 10 - - NN cord-276598-tm0yj2sn 213 11 functionalization functionalization JJ cord-276598-tm0yj2sn 213 12 step step NN cord-276598-tm0yj2sn 213 13 , , , cord-276598-tm0yj2sn 213 14 the the DT cord-276598-tm0yj2sn 213 15 production production NN cord-276598-tm0yj2sn 213 16 of of IN cord-276598-tm0yj2sn 213 17 large large JJ cord-276598-tm0yj2sn 213 18 amounts amount NNS cord-276598-tm0yj2sn 213 19 of of IN cord-276598-tm0yj2sn 213 20 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 213 21 waste waste NN cord-276598-tm0yj2sn 213 22 , , , cord-276598-tm0yj2sn 213 23 and and CC cord-276598-tm0yj2sn 213 24 the the DT cord-276598-tm0yj2sn 213 25 use use NN cord-276598-tm0yj2sn 213 26 of of IN cord-276598-tm0yj2sn 213 27 hazardous hazardous JJ cord-276598-tm0yj2sn 213 28 halogenating halogenating NN cord-276598-tm0yj2sn 213 29 reagents reagent NNS cord-276598-tm0yj2sn 213 30 . . . cord-276598-tm0yj2sn 214 1 A a DT cord-276598-tm0yj2sn 214 2 one one CD cord-276598-tm0yj2sn 214 3 - - HYPH cord-276598-tm0yj2sn 214 4 pot pot NN cord-276598-tm0yj2sn 214 5 synthesis synthesis NN cord-276598-tm0yj2sn 214 6 of of IN cord-276598-tm0yj2sn 214 7 P p NN cord-276598-tm0yj2sn 214 8 - - HYPH cord-276598-tm0yj2sn 214 9 Ns Ns NNP cord-276598-tm0yj2sn 214 10 was be VBD cord-276598-tm0yj2sn 214 11 reported report VBN cord-276598-tm0yj2sn 214 12 by by IN cord-276598-tm0yj2sn 214 13 Gupta Gupta NNP cord-276598-tm0yj2sn 214 14 et et NNP cord-276598-tm0yj2sn 214 15 al al NNP cord-276598-tm0yj2sn 214 16 . . . cord-276598-tm0yj2sn 215 1 ( ( -LRB- cord-276598-tm0yj2sn 215 2 Scheme scheme NN cord-276598-tm0yj2sn 215 3 6a 6a CD cord-276598-tm0yj2sn 215 4 ) ) -RRB- cord-276598-tm0yj2sn 216 1 [ [ -LRB- cord-276598-tm0yj2sn 216 2 97 97 CD cord-276598-tm0yj2sn 216 3 ] ] -RRB- cord-276598-tm0yj2sn 216 4 . . . cord-276598-tm0yj2sn 217 1 According accord VBG cord-276598-tm0yj2sn 217 2 to to IN cord-276598-tm0yj2sn 217 3 the the DT cord-276598-tm0yj2sn 217 4 authors author NNS cord-276598-tm0yj2sn 217 5 , , , cord-276598-tm0yj2sn 217 6 the the DT cord-276598-tm0yj2sn 217 7 chlorination chlorination NN cord-276598-tm0yj2sn 217 8 of of IN cord-276598-tm0yj2sn 217 9 ( ( -LRB- cord-276598-tm0yj2sn 217 10 RO ro NN cord-276598-tm0yj2sn 217 11 ) ) -RRB- cord-276598-tm0yj2sn 217 12 2 2 CD cord-276598-tm0yj2sn 217 13 P(O)H p(o)h NN cord-276598-tm0yj2sn 218 1 ( ( -LRB- cord-276598-tm0yj2sn 218 2 R r NN cord-276598-tm0yj2sn 218 3 = = NFP cord-276598-tm0yj2sn 218 4 Me -PRON- PRP cord-276598-tm0yj2sn 218 5 , , , cord-276598-tm0yj2sn 218 6 Et Et NNP cord-276598-tm0yj2sn 218 7 , , , cord-276598-tm0yj2sn 218 8 Pr Pr NNP cord-276598-tm0yj2sn 218 9 , , , cord-276598-tm0yj2sn 218 10 i i NN cord-276598-tm0yj2sn 218 11 - - HYPH cord-276598-tm0yj2sn 218 12 Pr pr NN cord-276598-tm0yj2sn 218 13 ; ; : cord-276598-tm0yj2sn 218 14 3 3 CD cord-276598-tm0yj2sn 218 15 eq eq NN cord-276598-tm0yj2sn 218 16 . . . cord-276598-tm0yj2sn 218 17 ) ) -RRB- cord-276598-tm0yj2sn 219 1 to to TO cord-276598-tm0yj2sn 219 2 afford afford VB cord-276598-tm0yj2sn 219 3 ( ( -LRB- cord-276598-tm0yj2sn 219 4 RO ro NN cord-276598-tm0yj2sn 219 5 ) ) -RRB- cord-276598-tm0yj2sn 219 6 2 2 CD cord-276598-tm0yj2sn 220 1 P(O)Cl P(O)Cl VBN cord-276598-tm0yj2sn 221 1 ( ( -LRB- cord-276598-tm0yj2sn 221 2 dACP dacp JJ cord-276598-tm0yj2sn 221 3 ; ; : cord-276598-tm0yj2sn 221 4 R r NN cord-276598-tm0yj2sn 221 5 = = NN cord-276598-tm0yj2sn 221 6 alkyl alkyl NN cord-276598-tm0yj2sn 221 7 ) ) -RRB- cord-276598-tm0yj2sn 221 8 was be VBD cord-276598-tm0yj2sn 221 9 possible possible JJ cord-276598-tm0yj2sn 221 10 upon upon IN cord-276598-tm0yj2sn 221 11 reacting react VBG cord-276598-tm0yj2sn 221 12 with with IN cord-276598-tm0yj2sn 221 13 trichloroisocyanuric trichloroisocyanuric NN cord-276598-tm0yj2sn 221 14 acid acid NN cord-276598-tm0yj2sn 221 15 ( ( -LRB- cord-276598-tm0yj2sn 221 16 tCiC tCiC NNP cord-276598-tm0yj2sn 221 17 - - HYPH cord-276598-tm0yj2sn 221 18 A a NN cord-276598-tm0yj2sn 221 19 ; ; : cord-276598-tm0yj2sn 221 20 1 1 CD cord-276598-tm0yj2sn 221 21 eq eq NN cord-276598-tm0yj2sn 221 22 . . NNP cord-276598-tm0yj2sn 221 23 ) ) -RRB- cord-276598-tm0yj2sn 221 24 , , , cord-276598-tm0yj2sn 221 25 which which WDT cord-276598-tm0yj2sn 221 26 was be VBD cord-276598-tm0yj2sn 221 27 then then RB cord-276598-tm0yj2sn 221 28 treated treat VBN cord-276598-tm0yj2sn 221 29 with with IN cord-276598-tm0yj2sn 221 30 an an DT cord-276598-tm0yj2sn 221 31 equal equal JJ cord-276598-tm0yj2sn 221 32 mixture mixture NN cord-276598-tm0yj2sn 221 33 of of IN cord-276598-tm0yj2sn 221 34 amines amine NNS cord-276598-tm0yj2sn 221 35 , , , cord-276598-tm0yj2sn 222 1 R'R"NH R'R"NH NNP cord-276598-tm0yj2sn 223 1 ( ( -LRB- cord-276598-tm0yj2sn 223 2 R r NN cord-276598-tm0yj2sn 223 3 ' ' '' cord-276598-tm0yj2sn 223 4 = = NFP cord-276598-tm0yj2sn 224 1 Me -PRON- PRP cord-276598-tm0yj2sn 224 2 , , , cord-276598-tm0yj2sn 224 3 Et Et NNP cord-276598-tm0yj2sn 224 4 , , , cord-276598-tm0yj2sn 224 5 Pr Pr NNP cord-276598-tm0yj2sn 224 6 ; ; : cord-276598-tm0yj2sn 224 7 R r NN cord-276598-tm0yj2sn 224 8 " " '' cord-276598-tm0yj2sn 224 9 = = SYM cord-276598-tm0yj2sn 224 10 H h NN cord-276598-tm0yj2sn 224 11 ) ) -RRB- cord-276598-tm0yj2sn 224 12 and and CC cord-276598-tm0yj2sn 224 13 Et Et NNP cord-276598-tm0yj2sn 224 14 3 3 CD cord-276598-tm0yj2sn 224 15 N N NNP cord-276598-tm0yj2sn 224 16 , , , cord-276598-tm0yj2sn 224 17 to to TO cord-276598-tm0yj2sn 224 18 form form VB cord-276598-tm0yj2sn 224 19 the the DT cord-276598-tm0yj2sn 224 20 P P NNP cord-276598-tm0yj2sn 224 21 - - HYPH cord-276598-tm0yj2sn 224 22 N n CD cord-276598-tm0yj2sn 224 23 in in IN cord-276598-tm0yj2sn 224 24 82 82 CD cord-276598-tm0yj2sn 224 25 - - SYM cord-276598-tm0yj2sn 224 26 92 92 CD cord-276598-tm0yj2sn 224 27 % % NN cord-276598-tm0yj2sn 224 28 yield yield NN cord-276598-tm0yj2sn 224 29 , , , cord-276598-tm0yj2sn 224 30 which which WDT cord-276598-tm0yj2sn 224 31 was be VBD cord-276598-tm0yj2sn 224 32 determined determine VBN cord-276598-tm0yj2sn 224 33 as as IN cord-276598-tm0yj2sn 224 34 conversions conversion NNS cord-276598-tm0yj2sn 224 35 by by IN cord-276598-tm0yj2sn 224 36 31 31 CD cord-276598-tm0yj2sn 224 37 P p NN cord-276598-tm0yj2sn 224 38 NMR nmr NN cord-276598-tm0yj2sn 224 39 spectroscopy spectroscopy NN cord-276598-tm0yj2sn 224 40 . . . cord-276598-tm0yj2sn 225 1 However however RB cord-276598-tm0yj2sn 225 2 , , , cord-276598-tm0yj2sn 225 3 the the DT cord-276598-tm0yj2sn 225 4 isolation isolation NN cord-276598-tm0yj2sn 225 5 of of IN cord-276598-tm0yj2sn 225 6 ( ( -LRB- cord-276598-tm0yj2sn 225 7 RO ro NN cord-276598-tm0yj2sn 225 8 ) ) -RRB- cord-276598-tm0yj2sn 225 9 2 2 CD cord-276598-tm0yj2sn 225 10 P(O)NR'R P(O)NR'R NNP cord-276598-tm0yj2sn 225 11 " " '' cord-276598-tm0yj2sn 225 12 ( ( -LRB- cord-276598-tm0yj2sn 225 13 R r NN cord-276598-tm0yj2sn 225 14 = = FW cord-276598-tm0yj2sn 225 15 Et et NN cord-276598-tm0yj2sn 225 16 , , , cord-276598-tm0yj2sn 225 17 R R NNP cord-276598-tm0yj2sn 225 18 ' ' '' cord-276598-tm0yj2sn 225 19 , , , cord-276598-tm0yj2sn 225 20 R r NN cord-276598-tm0yj2sn 225 21 " " '' cord-276598-tm0yj2sn 225 22 = = NFP cord-276598-tm0yj2sn 226 1 Et Et NNP cord-276598-tm0yj2sn 226 2 , , , cord-276598-tm0yj2sn 226 3 Pr pr NN cord-276598-tm0yj2sn 226 4 ) ) -RRB- cord-276598-tm0yj2sn 226 5 product product NN cord-276598-tm0yj2sn 226 6 gave give VBD cord-276598-tm0yj2sn 226 7 79 79 CD cord-276598-tm0yj2sn 226 8 % % NN cord-276598-tm0yj2sn 226 9 yield yield NN cord-276598-tm0yj2sn 226 10 . . . cord-276598-tm0yj2sn 227 1 A a DT cord-276598-tm0yj2sn 227 2 similar similar JJ cord-276598-tm0yj2sn 227 3 method method NN cord-276598-tm0yj2sn 227 4 , , , cord-276598-tm0yj2sn 227 5 under under IN cord-276598-tm0yj2sn 227 6 base base NN cord-276598-tm0yj2sn 227 7 - - HYPH cord-276598-tm0yj2sn 227 8 free free JJ cord-276598-tm0yj2sn 227 9 reaction reaction NN cord-276598-tm0yj2sn 227 10 conditions condition NNS cord-276598-tm0yj2sn 227 11 , , , cord-276598-tm0yj2sn 227 12 was be VBD cord-276598-tm0yj2sn 227 13 achieved achieve VBN cord-276598-tm0yj2sn 227 14 by by IN cord-276598-tm0yj2sn 227 15 Kaboudin Kaboudin NNP cord-276598-tm0yj2sn 227 16 et et NNP cord-276598-tm0yj2sn 227 17 al al NNP cord-276598-tm0yj2sn 227 18 . . . cord-276598-tm0yj2sn 228 1 ( ( -LRB- cord-276598-tm0yj2sn 228 2 Scheme scheme NN cord-276598-tm0yj2sn 228 3 6b 6b CD cord-276598-tm0yj2sn 228 4 ) ) -RRB- cord-276598-tm0yj2sn 228 5 [ [ -LRB- cord-276598-tm0yj2sn 228 6 98 98 CD cord-276598-tm0yj2sn 228 7 ] ] -RRB- cord-276598-tm0yj2sn 228 8 . . . cord-276598-tm0yj2sn 229 1 The the DT cord-276598-tm0yj2sn 229 2 scope scope NN cord-276598-tm0yj2sn 229 3 of of IN cord-276598-tm0yj2sn 229 4 the the DT cord-276598-tm0yj2sn 229 5 synthesis synthesis NN cord-276598-tm0yj2sn 229 6 was be VBD cord-276598-tm0yj2sn 229 7 explored explore VBN cord-276598-tm0yj2sn 229 8 with with IN cord-276598-tm0yj2sn 229 9 ( ( -LRB- cord-276598-tm0yj2sn 229 10 H h NN cord-276598-tm0yj2sn 229 11 - - HYPH cord-276598-tm0yj2sn 229 12 P p NN cord-276598-tm0yj2sn 229 13 ) ) -RRB- cord-276598-tm0yj2sn 230 1 ( ( -LRB- cord-276598-tm0yj2sn 230 2 ( ( -LRB- cord-276598-tm0yj2sn 230 3 RO RO NNP cord-276598-tm0yj2sn 230 4 ) ) -RRB- cord-276598-tm0yj2sn 230 5 2 2 CD cord-276598-tm0yj2sn 230 6 P(O)H p(o)h NN cord-276598-tm0yj2sn 230 7 ; ; : cord-276598-tm0yj2sn 230 8 R r NN cord-276598-tm0yj2sn 230 9 = = FW cord-276598-tm0yj2sn 230 10 Et et NN cord-276598-tm0yj2sn 230 11 , , , cord-276598-tm0yj2sn 230 12 i i NN cord-276598-tm0yj2sn 230 13 - - HYPH cord-276598-tm0yj2sn 230 14 Pr Pr NNP cord-276598-tm0yj2sn 230 15 ) ) -RRB- cord-276598-tm0yj2sn 230 16 and and CC cord-276598-tm0yj2sn 230 17 amine amine NN cord-276598-tm0yj2sn 230 18 ( ( -LRB- cord-276598-tm0yj2sn 230 19 e.g. e.g. RB cord-276598-tm0yj2sn 230 20 , , , cord-276598-tm0yj2sn 230 21 N n NN cord-276598-tm0yj2sn 230 22 - - HYPH cord-276598-tm0yj2sn 230 23 methylaniline methylaniline NNP cord-276598-tm0yj2sn 230 24 , , , cord-276598-tm0yj2sn 230 25 naphthalen-1-amine naphthalen-1-amine NNP cord-276598-tm0yj2sn 230 26 , , , cord-276598-tm0yj2sn 230 27 2-phenylethan-1-amine 2-phenylethan-1-amine CD cord-276598-tm0yj2sn 230 28 , , , cord-276598-tm0yj2sn 230 29 3-chloro-2-methylaniline 3-chloro-2-methylaniline CD cord-276598-tm0yj2sn 230 30 , , , cord-276598-tm0yj2sn 230 31 3-nitroaniline 3-nitroaniline CD cord-276598-tm0yj2sn 230 32 , , , cord-276598-tm0yj2sn 230 33 benzylamine benzylamine JJ cord-276598-tm0yj2sn 230 34 , , , cord-276598-tm0yj2sn 230 35 or or CC cord-276598-tm0yj2sn 230 36 aniline aniline NN cord-276598-tm0yj2sn 230 37 ) ) -RRB- cord-276598-tm0yj2sn 230 38 . . . cord-276598-tm0yj2sn 231 1 The the DT cord-276598-tm0yj2sn 231 2 crude crude JJ cord-276598-tm0yj2sn 231 3 product product NN cord-276598-tm0yj2sn 231 4 was be VBD cord-276598-tm0yj2sn 231 5 purified purify VBN cord-276598-tm0yj2sn 231 6 by by IN cord-276598-tm0yj2sn 231 7 column column NN cord-276598-tm0yj2sn 231 8 chromatography chromatography NN cord-276598-tm0yj2sn 231 9 ( ( -LRB- cord-276598-tm0yj2sn 231 10 on on IN cord-276598-tm0yj2sn 231 11 silica silica NN cord-276598-tm0yj2sn 231 12 ) ) -RRB- cord-276598-tm0yj2sn 231 13 to to TO cord-276598-tm0yj2sn 231 14 yield yield VB cord-276598-tm0yj2sn 231 15 isolated isolate VBN cord-276598-tm0yj2sn 231 16 pure pure JJ cord-276598-tm0yj2sn 231 17 products product NNS cord-276598-tm0yj2sn 231 18 in in IN cord-276598-tm0yj2sn 231 19 the the DT cord-276598-tm0yj2sn 231 20 range range NN cord-276598-tm0yj2sn 231 21 of of IN cord-276598-tm0yj2sn 231 22 22 22 CD cord-276598-tm0yj2sn 231 23 - - SYM cord-276598-tm0yj2sn 231 24 92 92 CD cord-276598-tm0yj2sn 231 25 % % NN cord-276598-tm0yj2sn 231 26 . . . cord-276598-tm0yj2sn 232 1 alkyl alkyl JJ cord-276598-tm0yj2sn 232 2 ) ) -RRB- cord-276598-tm0yj2sn 232 3 was be VBD cord-276598-tm0yj2sn 232 4 possible possible JJ cord-276598-tm0yj2sn 232 5 upon upon IN cord-276598-tm0yj2sn 232 6 reacting react VBG cord-276598-tm0yj2sn 232 7 with with IN cord-276598-tm0yj2sn 232 8 trichloroisocyanuric trichloroisocyanuric NN cord-276598-tm0yj2sn 232 9 acid acid NN cord-276598-tm0yj2sn 232 10 ( ( -LRB- cord-276598-tm0yj2sn 232 11 tCiC tCiC NNP cord-276598-tm0yj2sn 232 12 - - HYPH cord-276598-tm0yj2sn 232 13 A a NN cord-276598-tm0yj2sn 232 14 ; ; : cord-276598-tm0yj2sn 232 15 1 1 CD cord-276598-tm0yj2sn 232 16 eq eq NN cord-276598-tm0yj2sn 232 17 . . NNP cord-276598-tm0yj2sn 232 18 ) ) -RRB- cord-276598-tm0yj2sn 232 19 , , , cord-276598-tm0yj2sn 232 20 which which WDT cord-276598-tm0yj2sn 232 21 was be VBD cord-276598-tm0yj2sn 232 22 then then RB cord-276598-tm0yj2sn 232 23 treated treat VBN cord-276598-tm0yj2sn 232 24 with with IN cord-276598-tm0yj2sn 232 25 an an DT cord-276598-tm0yj2sn 232 26 equal equal JJ cord-276598-tm0yj2sn 232 27 mixture mixture NN cord-276598-tm0yj2sn 232 28 of of IN cord-276598-tm0yj2sn 232 29 amines amine NNS cord-276598-tm0yj2sn 232 30 , , , cord-276598-tm0yj2sn 232 31 R'R''NH R'R''NH NNS cord-276598-tm0yj2sn 232 32 ( ( -LRB- cord-276598-tm0yj2sn 232 33 R r NN cord-276598-tm0yj2sn 232 34 ' ' '' cord-276598-tm0yj2sn 232 35 = = NFP cord-276598-tm0yj2sn 233 1 Me -PRON- PRP cord-276598-tm0yj2sn 233 2 , , , cord-276598-tm0yj2sn 233 3 Et Et NNP cord-276598-tm0yj2sn 233 4 , , , cord-276598-tm0yj2sn 233 5 Pr Pr NNP cord-276598-tm0yj2sn 233 6 ; ; : cord-276598-tm0yj2sn 233 7 R R NNP cord-276598-tm0yj2sn 233 8 ' ' '' cord-276598-tm0yj2sn 233 9 ' ' '' cord-276598-tm0yj2sn 233 10 = = SYM cord-276598-tm0yj2sn 233 11 H h NN cord-276598-tm0yj2sn 233 12 ) ) -RRB- cord-276598-tm0yj2sn 233 13 and and CC cord-276598-tm0yj2sn 233 14 Et3N Et3N NNP cord-276598-tm0yj2sn 233 15 , , , cord-276598-tm0yj2sn 233 16 to to TO cord-276598-tm0yj2sn 233 17 form form VB cord-276598-tm0yj2sn 233 18 the the DT cord-276598-tm0yj2sn 233 19 P P NNP cord-276598-tm0yj2sn 233 20 - - HYPH cord-276598-tm0yj2sn 233 21 N n CD cord-276598-tm0yj2sn 233 22 in in IN cord-276598-tm0yj2sn 233 23 82 82 CD cord-276598-tm0yj2sn 233 24 - - SYM cord-276598-tm0yj2sn 233 25 92 92 CD cord-276598-tm0yj2sn 233 26 % % NN cord-276598-tm0yj2sn 233 27 yield yield NN cord-276598-tm0yj2sn 233 28 , , , cord-276598-tm0yj2sn 233 29 which which WDT cord-276598-tm0yj2sn 233 30 was be VBD cord-276598-tm0yj2sn 233 31 determined determine VBN cord-276598-tm0yj2sn 233 32 as as IN cord-276598-tm0yj2sn 233 33 conversions conversion NNS cord-276598-tm0yj2sn 233 34 by by IN cord-276598-tm0yj2sn 233 35 31 31 CD cord-276598-tm0yj2sn 233 36 P p NN cord-276598-tm0yj2sn 233 37 NMR nmr NN cord-276598-tm0yj2sn 233 38 spectroscopy spectroscopy NN cord-276598-tm0yj2sn 233 39 . . . cord-276598-tm0yj2sn 234 1 However however RB cord-276598-tm0yj2sn 234 2 , , , cord-276598-tm0yj2sn 234 3 the the DT cord-276598-tm0yj2sn 234 4 isolation isolation NN cord-276598-tm0yj2sn 234 5 of of IN cord-276598-tm0yj2sn 234 6 ( ( -LRB- cord-276598-tm0yj2sn 234 7 RO)2P(O)NR'R RO)2P(O)NR'R `` cord-276598-tm0yj2sn 234 8 " " '' cord-276598-tm0yj2sn 234 9 ( ( -LRB- cord-276598-tm0yj2sn 234 10 R r NN cord-276598-tm0yj2sn 234 11 = = FW cord-276598-tm0yj2sn 234 12 Et et NN cord-276598-tm0yj2sn 234 13 , , , cord-276598-tm0yj2sn 234 14 R R NNP cord-276598-tm0yj2sn 234 15 ' ' '' cord-276598-tm0yj2sn 234 16 , , , cord-276598-tm0yj2sn 234 17 R r NN cord-276598-tm0yj2sn 234 18 " " '' cord-276598-tm0yj2sn 234 19 = = FW cord-276598-tm0yj2sn 234 20 Et et NN cord-276598-tm0yj2sn 234 21 , , , cord-276598-tm0yj2sn 234 22 Pr pr NN cord-276598-tm0yj2sn 234 23 ) ) -RRB- cord-276598-tm0yj2sn 234 24 product product NN cord-276598-tm0yj2sn 234 25 gave give VBD cord-276598-tm0yj2sn 234 26 79 79 CD cord-276598-tm0yj2sn 234 27 % % NN cord-276598-tm0yj2sn 234 28 yield yield NN cord-276598-tm0yj2sn 234 29 . . . cord-276598-tm0yj2sn 235 1 A a DT cord-276598-tm0yj2sn 235 2 similar similar JJ cord-276598-tm0yj2sn 235 3 method method NN cord-276598-tm0yj2sn 235 4 , , , cord-276598-tm0yj2sn 235 5 under under IN cord-276598-tm0yj2sn 235 6 base base NN cord-276598-tm0yj2sn 235 7 - - HYPH cord-276598-tm0yj2sn 235 8 free free JJ cord-276598-tm0yj2sn 235 9 reaction reaction NN cord-276598-tm0yj2sn 235 10 conditions condition NNS cord-276598-tm0yj2sn 235 11 , , , cord-276598-tm0yj2sn 235 12 was be VBD cord-276598-tm0yj2sn 235 13 achieved achieve VBN cord-276598-tm0yj2sn 235 14 by by IN cord-276598-tm0yj2sn 235 15 Kaboudin Kaboudin NNP cord-276598-tm0yj2sn 235 16 et et NNP cord-276598-tm0yj2sn 235 17 al al NNP cord-276598-tm0yj2sn 235 18 . . . cord-276598-tm0yj2sn 236 1 ( ( -LRB- cord-276598-tm0yj2sn 236 2 Scheme scheme NN cord-276598-tm0yj2sn 236 3 6b 6b CD cord-276598-tm0yj2sn 236 4 ) ) -RRB- cord-276598-tm0yj2sn 236 5 [ [ -LRB- cord-276598-tm0yj2sn 236 6 98 98 CD cord-276598-tm0yj2sn 236 7 ] ] -RRB- cord-276598-tm0yj2sn 236 8 . . . cord-276598-tm0yj2sn 237 1 The the DT cord-276598-tm0yj2sn 237 2 scope scope NN cord-276598-tm0yj2sn 237 3 of of IN cord-276598-tm0yj2sn 237 4 the the DT cord-276598-tm0yj2sn 237 5 synthesis synthesis NN cord-276598-tm0yj2sn 237 6 was be VBD cord-276598-tm0yj2sn 237 7 explored explore VBN cord-276598-tm0yj2sn 237 8 with with IN cord-276598-tm0yj2sn 237 9 ( ( -LRB- cord-276598-tm0yj2sn 237 10 H h NN cord-276598-tm0yj2sn 237 11 - - HYPH cord-276598-tm0yj2sn 237 12 P p NN cord-276598-tm0yj2sn 237 13 ) ) -RRB- cord-276598-tm0yj2sn 237 14 ( ( -LRB- cord-276598-tm0yj2sn 237 15 ( ( -LRB- cord-276598-tm0yj2sn 237 16 RO)2P(O)H ro)2p(o)h NN cord-276598-tm0yj2sn 237 17 ; ; . cord-276598-tm0yj2sn 238 1 R r NN cord-276598-tm0yj2sn 238 2 = = FW cord-276598-tm0yj2sn 238 3 Et Et NNP cord-276598-tm0yj2sn 238 4 , , , cord-276598-tm0yj2sn 238 5 i i NN cord-276598-tm0yj2sn 238 6 - - HYPH cord-276598-tm0yj2sn 238 7 Pr Pr NNP cord-276598-tm0yj2sn 238 8 ) ) -RRB- cord-276598-tm0yj2sn 238 9 and and CC cord-276598-tm0yj2sn 238 10 amine amine NN cord-276598-tm0yj2sn 238 11 ( ( -LRB- cord-276598-tm0yj2sn 238 12 e.g. e.g. RB cord-276598-tm0yj2sn 238 13 , , , cord-276598-tm0yj2sn 238 14 N n NN cord-276598-tm0yj2sn 238 15 - - HYPH cord-276598-tm0yj2sn 238 16 methylaniline methylaniline NNP cord-276598-tm0yj2sn 238 17 , , , cord-276598-tm0yj2sn 238 18 naphthalen-1-amine naphthalen-1-amine NNP cord-276598-tm0yj2sn 238 19 , , , cord-276598-tm0yj2sn 238 20 2-phenylethan-1-amine 2-phenylethan-1-amine CD cord-276598-tm0yj2sn 238 21 , , , cord-276598-tm0yj2sn 238 22 3-chloro-2-methylaniline 3-chloro-2-methylaniline CD cord-276598-tm0yj2sn 238 23 , , , cord-276598-tm0yj2sn 238 24 3-nitroaniline 3-nitroaniline CD cord-276598-tm0yj2sn 238 25 , , , cord-276598-tm0yj2sn 238 26 benzylamine benzylamine JJ cord-276598-tm0yj2sn 238 27 , , , cord-276598-tm0yj2sn 238 28 or or CC cord-276598-tm0yj2sn 238 29 aniline aniline NN cord-276598-tm0yj2sn 238 30 ) ) -RRB- cord-276598-tm0yj2sn 238 31 . . . cord-276598-tm0yj2sn 239 1 The the DT cord-276598-tm0yj2sn 239 2 crude crude JJ cord-276598-tm0yj2sn 239 3 product product NN cord-276598-tm0yj2sn 239 4 was be VBD cord-276598-tm0yj2sn 239 5 purified purify VBN cord-276598-tm0yj2sn 239 6 by by IN cord-276598-tm0yj2sn 239 7 column column NN cord-276598-tm0yj2sn 239 8 chromatography chromatography NN cord-276598-tm0yj2sn 239 9 ( ( -LRB- cord-276598-tm0yj2sn 239 10 on on IN cord-276598-tm0yj2sn 239 11 silica silica NN cord-276598-tm0yj2sn 239 12 ) ) -RRB- cord-276598-tm0yj2sn 239 13 to to TO cord-276598-tm0yj2sn 239 14 yield yield VB cord-276598-tm0yj2sn 239 15 isolated isolate VBN cord-276598-tm0yj2sn 239 16 pure pure JJ cord-276598-tm0yj2sn 239 17 products product NNS cord-276598-tm0yj2sn 239 18 in in IN cord-276598-tm0yj2sn 239 19 the the DT cord-276598-tm0yj2sn 239 20 range range NN cord-276598-tm0yj2sn 239 21 of of IN cord-276598-tm0yj2sn 239 22 22 22 CD cord-276598-tm0yj2sn 239 23 - - SYM cord-276598-tm0yj2sn 239 24 92 92 CD cord-276598-tm0yj2sn 239 25 % % NN cord-276598-tm0yj2sn 239 26 . . . cord-276598-tm0yj2sn 240 1 Jang Jang NNP cord-276598-tm0yj2sn 240 2 and and CC cord-276598-tm0yj2sn 240 3 coworkers coworker NNS cord-276598-tm0yj2sn 240 4 reported report VBD cord-276598-tm0yj2sn 240 5 a a DT cord-276598-tm0yj2sn 240 6 facile facile JJ cord-276598-tm0yj2sn 240 7 synthetic synthetic JJ cord-276598-tm0yj2sn 240 8 route route NN cord-276598-tm0yj2sn 240 9 to to TO cord-276598-tm0yj2sn 240 10 form form VB cord-276598-tm0yj2sn 240 11 P p NN cord-276598-tm0yj2sn 240 12 - - HYPH cord-276598-tm0yj2sn 240 13 Ns Ns NNP cord-276598-tm0yj2sn 240 14 using use VBG cord-276598-tm0yj2sn 240 15 diphenyl diphenyl NNP cord-276598-tm0yj2sn 240 16 phosphoric phosphoric JJ cord-276598-tm0yj2sn 240 17 acid acid NN cord-276598-tm0yj2sn 240 18 ( ( -LRB- cord-276598-tm0yj2sn 240 19 dPPA dPPA NNP cord-276598-tm0yj2sn 240 20 ) ) -RRB- cord-276598-tm0yj2sn 240 21 and and CC cord-276598-tm0yj2sn 240 22 an an DT cord-276598-tm0yj2sn 240 23 amine amine NN cord-276598-tm0yj2sn 240 24 in in IN cord-276598-tm0yj2sn 240 25 the the DT cord-276598-tm0yj2sn 240 26 presence presence NN cord-276598-tm0yj2sn 240 27 of of IN cord-276598-tm0yj2sn 240 28 both both CC cord-276598-tm0yj2sn 240 29 a a DT cord-276598-tm0yj2sn 240 30 chlorinating chlorinate VBG cord-276598-tm0yj2sn 240 31 agent agent NN cord-276598-tm0yj2sn 240 32 ( ( -LRB- cord-276598-tm0yj2sn 240 33 Cl3CCN Cl3CCN NNP cord-276598-tm0yj2sn 240 34 ) ) -RRB- cord-276598-tm0yj2sn 240 35 and and CC cord-276598-tm0yj2sn 240 36 a a DT cord-276598-tm0yj2sn 240 37 base base NN cord-276598-tm0yj2sn 240 38 ( ( -LRB- cord-276598-tm0yj2sn 240 39 Et3N Et3N NNP cord-276598-tm0yj2sn 240 40 ) ) -RRB- cord-276598-tm0yj2sn 240 41 , , , cord-276598-tm0yj2sn 240 42 which which WDT cord-276598-tm0yj2sn 240 43 was be VBD cord-276598-tm0yj2sn 240 44 added add VBN cord-276598-tm0yj2sn 240 45 to to TO cord-276598-tm0yj2sn 240 46 sequester sequester VB cord-276598-tm0yj2sn 240 47 the the DT cord-276598-tm0yj2sn 240 48 acid acid NN cord-276598-tm0yj2sn 240 49 formed form VBN cord-276598-tm0yj2sn 240 50 during during IN cord-276598-tm0yj2sn 240 51 the the DT cord-276598-tm0yj2sn 240 52 reaction reaction NN cord-276598-tm0yj2sn 240 53 ( ( -LRB- cord-276598-tm0yj2sn 240 54 Scheme scheme NN cord-276598-tm0yj2sn 240 55 6c 6c CD cord-276598-tm0yj2sn 240 56 ) ) -RRB- cord-276598-tm0yj2sn 240 57 [ [ -LRB- cord-276598-tm0yj2sn 240 58 99 99 CD cord-276598-tm0yj2sn 240 59 ] ] -RRB- cord-276598-tm0yj2sn 240 60 . . . cord-276598-tm0yj2sn 241 1 The the DT cord-276598-tm0yj2sn 241 2 applicability applicability NN cord-276598-tm0yj2sn 241 3 of of IN cord-276598-tm0yj2sn 241 4 the the DT cord-276598-tm0yj2sn 241 5 method method NN cord-276598-tm0yj2sn 241 6 was be VBD cord-276598-tm0yj2sn 241 7 explored explore VBN cord-276598-tm0yj2sn 241 8 using use VBG cord-276598-tm0yj2sn 241 9 prop-2-en-1-amine prop-2-en-1-amine NN cord-276598-tm0yj2sn 241 10 , , , cord-276598-tm0yj2sn 241 11 diethylamine diethylamine NNP cord-276598-tm0yj2sn 241 12 , , , cord-276598-tm0yj2sn 241 13 2-methylpropan-2-amine 2-methylpropan-2-amine CD cord-276598-tm0yj2sn 241 14 , , , cord-276598-tm0yj2sn 241 15 cyclohexylamine cyclohexylamine NN cord-276598-tm0yj2sn 241 16 , , , cord-276598-tm0yj2sn 241 17 piperidine piperidine NN cord-276598-tm0yj2sn 241 18 , , , cord-276598-tm0yj2sn 241 19 morpholine morpholine NN cord-276598-tm0yj2sn 241 20 , , , cord-276598-tm0yj2sn 241 21 and and CC cord-276598-tm0yj2sn 241 22 aniline aniline NN cord-276598-tm0yj2sn 241 23 . . . cord-276598-tm0yj2sn 242 1 The the DT cord-276598-tm0yj2sn 242 2 crude crude JJ cord-276598-tm0yj2sn 242 3 product product NN cord-276598-tm0yj2sn 242 4 was be VBD cord-276598-tm0yj2sn 242 5 purified purify VBN cord-276598-tm0yj2sn 242 6 by by IN cord-276598-tm0yj2sn 242 7 column column NN cord-276598-tm0yj2sn 242 8 chromatography chromatography NN cord-276598-tm0yj2sn 242 9 ( ( -LRB- cord-276598-tm0yj2sn 242 10 on on IN cord-276598-tm0yj2sn 242 11 silica silica NN cord-276598-tm0yj2sn 242 12 ) ) -RRB- cord-276598-tm0yj2sn 242 13 to to TO cord-276598-tm0yj2sn 242 14 obtain obtain VB cord-276598-tm0yj2sn 242 15 isolated isolated JJ cord-276598-tm0yj2sn 242 16 yields yield NNS cord-276598-tm0yj2sn 242 17 of of IN cord-276598-tm0yj2sn 242 18 P p NN cord-276598-tm0yj2sn 242 19 - - HYPH cord-276598-tm0yj2sn 242 20 N n CD cord-276598-tm0yj2sn 242 21 products product NNS cord-276598-tm0yj2sn 242 22 in in IN cord-276598-tm0yj2sn 242 23 the the DT cord-276598-tm0yj2sn 242 24 range range NN cord-276598-tm0yj2sn 242 25 of of IN cord-276598-tm0yj2sn 242 26 53 53 CD cord-276598-tm0yj2sn 242 27 - - SYM cord-276598-tm0yj2sn 242 28 93 93 CD cord-276598-tm0yj2sn 242 29 % % NN cord-276598-tm0yj2sn 242 30 . . . cord-276598-tm0yj2sn 243 1 A a DT cord-276598-tm0yj2sn 243 2 similar similar JJ cord-276598-tm0yj2sn 243 3 chlorination chlorination NN cord-276598-tm0yj2sn 243 4 method method NN cord-276598-tm0yj2sn 243 5 reacting react VBG cord-276598-tm0yj2sn 243 6 an an DT cord-276598-tm0yj2sn 243 7 amine amine NN cord-276598-tm0yj2sn 243 8 ( ( -LRB- cord-276598-tm0yj2sn 243 9 e.g. e.g. RB cord-276598-tm0yj2sn 243 10 , , , cord-276598-tm0yj2sn 243 11 aniline aniline NN cord-276598-tm0yj2sn 243 12 , , , cord-276598-tm0yj2sn 243 13 hexylamine hexylamine NNP cord-276598-tm0yj2sn 243 14 , , , cord-276598-tm0yj2sn 243 15 diethylamine diethylamine NNP cord-276598-tm0yj2sn 243 16 , , , cord-276598-tm0yj2sn 243 17 and and CC cord-276598-tm0yj2sn 243 18 methanamine methanamine NN cord-276598-tm0yj2sn 243 19 ) ) -RRB- cord-276598-tm0yj2sn 243 20 with with IN cord-276598-tm0yj2sn 243 21 phosphoric phosphoric JJ cord-276598-tm0yj2sn 243 22 acid acid NN cord-276598-tm0yj2sn 243 23 ( ( -LRB- cord-276598-tm0yj2sn 243 24 ( ( -LRB- cord-276598-tm0yj2sn 243 25 R2P(O)OH r2p(o)oh NN cord-276598-tm0yj2sn 243 26 ; ; : cord-276598-tm0yj2sn 243 27 R r NN cord-276598-tm0yj2sn 243 28 = = SYM cord-276598-tm0yj2sn 243 29 OEt OEt NNS cord-276598-tm0yj2sn 243 30 , , , cord-276598-tm0yj2sn 243 31 OBu OBu NNS cord-276598-tm0yj2sn 243 32 , , , cord-276598-tm0yj2sn 243 33 OBn OBn NNS cord-276598-tm0yj2sn 243 34 ) ) -RRB- cord-276598-tm0yj2sn 243 35 in in IN cord-276598-tm0yj2sn 243 36 the the DT cord-276598-tm0yj2sn 243 37 presence presence NN cord-276598-tm0yj2sn 243 38 of of IN cord-276598-tm0yj2sn 243 39 triphenylphosphine triphenylphosphine NN cord-276598-tm0yj2sn 243 40 and and CC cord-276598-tm0yj2sn 243 41 CCl4 CCl4 NNP cord-276598-tm0yj2sn 243 42 was be VBD cord-276598-tm0yj2sn 243 43 also also RB cord-276598-tm0yj2sn 243 44 used use VBN cord-276598-tm0yj2sn 243 45 to to TO cord-276598-tm0yj2sn 243 46 synthesize synthesize VB cord-276598-tm0yj2sn 243 47 P p NN cord-276598-tm0yj2sn 243 48 - - HYPH cord-276598-tm0yj2sn 243 49 Ns Ns NNP cord-276598-tm0yj2sn 243 50 ( ( -LRB- cord-276598-tm0yj2sn 243 51 Scheme scheme NN cord-276598-tm0yj2sn 243 52 6d 6d CD cord-276598-tm0yj2sn 243 53 ) ) -RRB- cord-276598-tm0yj2sn 243 54 [ [ -LRB- cord-276598-tm0yj2sn 243 55 86 86 CD cord-276598-tm0yj2sn 243 56 ] ] -RRB- cord-276598-tm0yj2sn 243 57 . . . cord-276598-tm0yj2sn 244 1 The the DT cord-276598-tm0yj2sn 244 2 isolated isolated JJ cord-276598-tm0yj2sn 244 3 yields yield NNS cord-276598-tm0yj2sn 244 4 of of IN cord-276598-tm0yj2sn 244 5 the the DT cord-276598-tm0yj2sn 244 6 products product NNS cord-276598-tm0yj2sn 244 7 in in IN cord-276598-tm0yj2sn 244 8 this this DT cord-276598-tm0yj2sn 244 9 case case NN cord-276598-tm0yj2sn 244 10 were be VBD cord-276598-tm0yj2sn 244 11 in in IN cord-276598-tm0yj2sn 244 12 the the DT cord-276598-tm0yj2sn 244 13 range range NN cord-276598-tm0yj2sn 244 14 of of IN cord-276598-tm0yj2sn 244 15 30 30 CD cord-276598-tm0yj2sn 244 16 - - SYM cord-276598-tm0yj2sn 244 17 75 75 CD cord-276598-tm0yj2sn 244 18 % % NN cord-276598-tm0yj2sn 244 19 . . . cord-276598-tm0yj2sn 245 1 P p NN cord-276598-tm0yj2sn 245 2 - - HYPH cord-276598-tm0yj2sn 245 3 N n CD cord-276598-tm0yj2sn 245 4 synthesis synthesis NN cord-276598-tm0yj2sn 245 5 via via IN cord-276598-tm0yj2sn 245 6 oxidative oxidative JJ cord-276598-tm0yj2sn 245 7 cross cross NN cord-276598-tm0yj2sn 245 8 - - NN cord-276598-tm0yj2sn 245 9 coupling coupling JJ cord-276598-tm0yj2sn 245 10 using use VBG cord-276598-tm0yj2sn 245 11 chlorinating chlorinate VBG cord-276598-tm0yj2sn 245 12 agents agent NNS cord-276598-tm0yj2sn 245 13 offers offer VBZ cord-276598-tm0yj2sn 245 14 a a DT cord-276598-tm0yj2sn 245 15 short short JJ cord-276598-tm0yj2sn 245 16 reaction reaction NN cord-276598-tm0yj2sn 245 17 time time NN cord-276598-tm0yj2sn 245 18 , , , cord-276598-tm0yj2sn 245 19 low low JJ cord-276598-tm0yj2sn 245 20 temperature temperature NN cord-276598-tm0yj2sn 245 21 synthesis synthesis NN cord-276598-tm0yj2sn 245 22 , , , cord-276598-tm0yj2sn 245 23 and and CC cord-276598-tm0yj2sn 245 24 a a DT cord-276598-tm0yj2sn 245 25 diverse diverse JJ cord-276598-tm0yj2sn 245 26 choice choice NN cord-276598-tm0yj2sn 245 27 of of IN cord-276598-tm0yj2sn 245 28 phosphorylating phosphorylate VBG cord-276598-tm0yj2sn 245 29 reagents reagent NNS cord-276598-tm0yj2sn 245 30 . . . cord-276598-tm0yj2sn 246 1 Nevertheless nevertheless RB cord-276598-tm0yj2sn 246 2 , , , cord-276598-tm0yj2sn 246 3 the the DT cord-276598-tm0yj2sn 246 4 methods method NNS cord-276598-tm0yj2sn 246 5 use use VBP cord-276598-tm0yj2sn 246 6 hazardous hazardous JJ cord-276598-tm0yj2sn 246 7 chlorinating chlorinating NN cord-276598-tm0yj2sn 246 8 agents agent NNS cord-276598-tm0yj2sn 246 9 such such JJ cord-276598-tm0yj2sn 246 10 as as IN cord-276598-tm0yj2sn 246 11 CCl4 CCl4 NNP cord-276598-tm0yj2sn 246 12 and and CC cord-276598-tm0yj2sn 246 13 Cl3CCN Cl3CCN NNP cord-276598-tm0yj2sn 246 14 , , , cord-276598-tm0yj2sn 246 15 generate generate VBP cord-276598-tm0yj2sn 246 16 large large JJ cord-276598-tm0yj2sn 246 17 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 246 18 wastes waste NNS cord-276598-tm0yj2sn 246 19 , , , cord-276598-tm0yj2sn 246 20 and and CC cord-276598-tm0yj2sn 246 21 involve involve VBP cord-276598-tm0yj2sn 246 22 a a DT cord-276598-tm0yj2sn 246 23 pre pre JJ cord-276598-tm0yj2sn 246 24 - - NN cord-276598-tm0yj2sn 246 25 functionalization functionalization JJ cord-276598-tm0yj2sn 246 26 step step NN cord-276598-tm0yj2sn 246 27 in in IN cord-276598-tm0yj2sn 246 28 the the DT cord-276598-tm0yj2sn 246 29 synthetic synthetic JJ cord-276598-tm0yj2sn 246 30 process process NN cord-276598-tm0yj2sn 246 31 . . . cord-276598-tm0yj2sn 246 32 _SP cord-276598-tm0yj2sn 247 1 The the DT cord-276598-tm0yj2sn 247 2 synthesis synthesis NN cord-276598-tm0yj2sn 247 3 of of IN cord-276598-tm0yj2sn 247 4 P p NN cord-276598-tm0yj2sn 247 5 - - HYPH cord-276598-tm0yj2sn 247 6 Ns Ns NNP cord-276598-tm0yj2sn 247 7 from from IN cord-276598-tm0yj2sn 247 8 amines amine NNS cord-276598-tm0yj2sn 247 9 ( ( -LRB- cord-276598-tm0yj2sn 247 10 aromatic aromatic JJ cord-276598-tm0yj2sn 247 11 and and CC cord-276598-tm0yj2sn 247 12 aliphatic aliphatic JJ cord-276598-tm0yj2sn 247 13 ) ) -RRB- cord-276598-tm0yj2sn 247 14 and and CC cord-276598-tm0yj2sn 247 15 symmetrical symmetrical JJ cord-276598-tm0yj2sn 247 16 trialkyl trialkyl NN cord-276598-tm0yj2sn 247 17 phosphite phosphite NNP cord-276598-tm0yj2sn 247 18 ( ( -LRB- cord-276598-tm0yj2sn 247 19 P(OR)3 p(or)3 CD cord-276598-tm0yj2sn 247 20 ; ; : cord-276598-tm0yj2sn 248 1 R= R= VBZ cord-276598-tm0yj2sn 248 2 Me -PRON- PRP cord-276598-tm0yj2sn 248 3 , , , cord-276598-tm0yj2sn 248 4 Et Et NNP cord-276598-tm0yj2sn 248 5 , , , cord-276598-tm0yj2sn 248 6 i i NN cord-276598-tm0yj2sn 248 7 - - HYPH cord-276598-tm0yj2sn 248 8 Pr Pr NNP cord-276598-tm0yj2sn 248 9 ) ) -RRB- cord-276598-tm0yj2sn 248 10 in in IN cord-276598-tm0yj2sn 248 11 the the DT cord-276598-tm0yj2sn 248 12 presence presence NN cord-276598-tm0yj2sn 248 13 I2 I2 NNP cord-276598-tm0yj2sn 248 14 was be VBD cord-276598-tm0yj2sn 248 15 reported report VBN cord-276598-tm0yj2sn 248 16 by by IN cord-276598-tm0yj2sn 248 17 Chen Chen NNP cord-276598-tm0yj2sn 248 18 et et NNP cord-276598-tm0yj2sn 248 19 al al NNP cord-276598-tm0yj2sn 248 20 . . . cord-276598-tm0yj2sn 249 1 [ [ -LRB- cord-276598-tm0yj2sn 249 2 100 100 CD cord-276598-tm0yj2sn 249 3 ] ] -RRB- cord-276598-tm0yj2sn 249 4 . . . cord-276598-tm0yj2sn 250 1 Crude crude JJ cord-276598-tm0yj2sn 250 2 products product NNS cord-276598-tm0yj2sn 250 3 were be VBD cord-276598-tm0yj2sn 250 4 purified purify VBN cord-276598-tm0yj2sn 250 5 by by IN cord-276598-tm0yj2sn 250 6 column column NN cord-276598-tm0yj2sn 250 7 chromatography chromatography NN cord-276598-tm0yj2sn 250 8 ( ( -LRB- cord-276598-tm0yj2sn 250 9 on on IN cord-276598-tm0yj2sn 250 10 silica silica NN cord-276598-tm0yj2sn 250 11 ) ) -RRB- cord-276598-tm0yj2sn 250 12 and and CC cord-276598-tm0yj2sn 250 13 resulted result VBD cord-276598-tm0yj2sn 250 14 in in IN cord-276598-tm0yj2sn 250 15 yields yield NNS cord-276598-tm0yj2sn 250 16 in in IN cord-276598-tm0yj2sn 250 17 the the DT cord-276598-tm0yj2sn 250 18 range range NN cord-276598-tm0yj2sn 250 19 of of IN cord-276598-tm0yj2sn 250 20 0 0 CD cord-276598-tm0yj2sn 250 21 - - SYM cord-276598-tm0yj2sn 250 22 95 95 CD cord-276598-tm0yj2sn 250 23 % % NN cord-276598-tm0yj2sn 250 24 . . . cord-276598-tm0yj2sn 251 1 For for IN cord-276598-tm0yj2sn 251 2 the the DT cord-276598-tm0yj2sn 251 3 low low JJ cord-276598-tm0yj2sn 251 4 yielding yield VBG cord-276598-tm0yj2sn 251 5 derivatives derivative NNS cord-276598-tm0yj2sn 251 6 , , , cord-276598-tm0yj2sn 251 7 the the DT cord-276598-tm0yj2sn 251 8 reaction reaction NN cord-276598-tm0yj2sn 251 9 was be VBD cord-276598-tm0yj2sn 251 10 more more RBR cord-276598-tm0yj2sn 251 11 selective selective JJ cord-276598-tm0yj2sn 251 12 to to IN cord-276598-tm0yj2sn 251 13 three three CD cord-276598-tm0yj2sn 251 14 identified identify VBN cord-276598-tm0yj2sn 251 15 by by IN cord-276598-tm0yj2sn 251 16 - - HYPH cord-276598-tm0yj2sn 251 17 products product NNS cord-276598-tm0yj2sn 251 18 , , , cord-276598-tm0yj2sn 251 19 H H NNP cord-276598-tm0yj2sn 251 20 - - HYPH cord-276598-tm0yj2sn 251 21 phosphonate phosphonate NNP cord-276598-tm0yj2sn 251 22 , , , cord-276598-tm0yj2sn 251 23 trialkyl trialkyl JJ cord-276598-tm0yj2sn 251 24 phosphate phosphate NN cord-276598-tm0yj2sn 251 25 , , , cord-276598-tm0yj2sn 251 26 and and CC cord-276598-tm0yj2sn 251 27 tetraalkyl tetraalkyl NN cord-276598-tm0yj2sn 251 28 diphosphate diphosphate NN cord-276598-tm0yj2sn 251 29 , , , cord-276598-tm0yj2sn 251 30 as as RB cord-276598-tm0yj2sn 251 31 well well RB cord-276598-tm0yj2sn 251 32 as as IN cord-276598-tm0yj2sn 251 33 some some DT cord-276598-tm0yj2sn 251 34 other other JJ cord-276598-tm0yj2sn 251 35 unidentified unidentified JJ cord-276598-tm0yj2sn 251 36 Jang Jang NNP cord-276598-tm0yj2sn 251 37 and and CC cord-276598-tm0yj2sn 251 38 coworkers coworker NNS cord-276598-tm0yj2sn 251 39 reported report VBD cord-276598-tm0yj2sn 251 40 a a DT cord-276598-tm0yj2sn 251 41 facile facile JJ cord-276598-tm0yj2sn 251 42 synthetic synthetic JJ cord-276598-tm0yj2sn 251 43 route route NN cord-276598-tm0yj2sn 251 44 to to TO cord-276598-tm0yj2sn 251 45 form form VB cord-276598-tm0yj2sn 251 46 P p NN cord-276598-tm0yj2sn 251 47 - - HYPH cord-276598-tm0yj2sn 251 48 Ns Ns NNP cord-276598-tm0yj2sn 251 49 using use VBG cord-276598-tm0yj2sn 251 50 diphenyl diphenyl NNP cord-276598-tm0yj2sn 251 51 phosphoric phosphoric JJ cord-276598-tm0yj2sn 251 52 acid acid NN cord-276598-tm0yj2sn 251 53 ( ( -LRB- cord-276598-tm0yj2sn 251 54 dPPA dPPA NNP cord-276598-tm0yj2sn 251 55 ) ) -RRB- cord-276598-tm0yj2sn 251 56 and and CC cord-276598-tm0yj2sn 251 57 an an DT cord-276598-tm0yj2sn 251 58 amine amine NN cord-276598-tm0yj2sn 251 59 in in IN cord-276598-tm0yj2sn 251 60 the the DT cord-276598-tm0yj2sn 251 61 presence presence NN cord-276598-tm0yj2sn 251 62 of of IN cord-276598-tm0yj2sn 251 63 both both CC cord-276598-tm0yj2sn 251 64 a a DT cord-276598-tm0yj2sn 251 65 chlorinating chlorinate VBG cord-276598-tm0yj2sn 251 66 agent agent NN cord-276598-tm0yj2sn 251 67 ( ( -LRB- cord-276598-tm0yj2sn 251 68 Cl Cl NNP cord-276598-tm0yj2sn 251 69 3 3 CD cord-276598-tm0yj2sn 251 70 CCN CCN NNP cord-276598-tm0yj2sn 251 71 ) ) -RRB- cord-276598-tm0yj2sn 251 72 and and CC cord-276598-tm0yj2sn 251 73 a a DT cord-276598-tm0yj2sn 251 74 base base NN cord-276598-tm0yj2sn 251 75 ( ( -LRB- cord-276598-tm0yj2sn 251 76 Et Et NNP cord-276598-tm0yj2sn 251 77 3 3 CD cord-276598-tm0yj2sn 251 78 N N NNP cord-276598-tm0yj2sn 251 79 ) ) -RRB- cord-276598-tm0yj2sn 251 80 , , , cord-276598-tm0yj2sn 251 81 which which WDT cord-276598-tm0yj2sn 251 82 was be VBD cord-276598-tm0yj2sn 251 83 added add VBN cord-276598-tm0yj2sn 251 84 to to TO cord-276598-tm0yj2sn 251 85 sequester sequester VB cord-276598-tm0yj2sn 251 86 the the DT cord-276598-tm0yj2sn 251 87 acid acid NN cord-276598-tm0yj2sn 251 88 formed form VBN cord-276598-tm0yj2sn 251 89 during during IN cord-276598-tm0yj2sn 251 90 the the DT cord-276598-tm0yj2sn 251 91 reaction reaction NN cord-276598-tm0yj2sn 251 92 ( ( -LRB- cord-276598-tm0yj2sn 251 93 Scheme scheme NN cord-276598-tm0yj2sn 251 94 6c 6c CD cord-276598-tm0yj2sn 251 95 ) ) -RRB- cord-276598-tm0yj2sn 251 96 [ [ -LRB- cord-276598-tm0yj2sn 251 97 99 99 CD cord-276598-tm0yj2sn 251 98 ] ] -RRB- cord-276598-tm0yj2sn 251 99 . . . cord-276598-tm0yj2sn 252 1 The the DT cord-276598-tm0yj2sn 252 2 applicability applicability NN cord-276598-tm0yj2sn 252 3 of of IN cord-276598-tm0yj2sn 252 4 the the DT cord-276598-tm0yj2sn 252 5 method method NN cord-276598-tm0yj2sn 252 6 was be VBD cord-276598-tm0yj2sn 252 7 explored explore VBN cord-276598-tm0yj2sn 252 8 using use VBG cord-276598-tm0yj2sn 252 9 prop-2-en-1-amine prop-2-en-1-amine NN cord-276598-tm0yj2sn 252 10 , , , cord-276598-tm0yj2sn 252 11 diethylamine diethylamine NNP cord-276598-tm0yj2sn 252 12 , , , cord-276598-tm0yj2sn 252 13 2-methylpropan-2-amine 2-methylpropan-2-amine CD cord-276598-tm0yj2sn 252 14 , , , cord-276598-tm0yj2sn 252 15 cyclohexylamine cyclohexylamine NN cord-276598-tm0yj2sn 252 16 , , , cord-276598-tm0yj2sn 252 17 piperidine piperidine NN cord-276598-tm0yj2sn 252 18 , , , cord-276598-tm0yj2sn 252 19 morpholine morpholine NN cord-276598-tm0yj2sn 252 20 , , , cord-276598-tm0yj2sn 252 21 and and CC cord-276598-tm0yj2sn 252 22 aniline aniline NN cord-276598-tm0yj2sn 252 23 . . . cord-276598-tm0yj2sn 253 1 The the DT cord-276598-tm0yj2sn 253 2 crude crude JJ cord-276598-tm0yj2sn 253 3 product product NN cord-276598-tm0yj2sn 253 4 was be VBD cord-276598-tm0yj2sn 253 5 purified purify VBN cord-276598-tm0yj2sn 253 6 by by IN cord-276598-tm0yj2sn 253 7 column column NN cord-276598-tm0yj2sn 253 8 chromatography chromatography NN cord-276598-tm0yj2sn 253 9 ( ( -LRB- cord-276598-tm0yj2sn 253 10 on on IN cord-276598-tm0yj2sn 253 11 silica silica NN cord-276598-tm0yj2sn 253 12 ) ) -RRB- cord-276598-tm0yj2sn 253 13 to to TO cord-276598-tm0yj2sn 253 14 obtain obtain VB cord-276598-tm0yj2sn 253 15 isolated isolated JJ cord-276598-tm0yj2sn 253 16 yields yield NNS cord-276598-tm0yj2sn 253 17 of of IN cord-276598-tm0yj2sn 253 18 P p NN cord-276598-tm0yj2sn 253 19 - - HYPH cord-276598-tm0yj2sn 253 20 N n CD cord-276598-tm0yj2sn 253 21 products product NNS cord-276598-tm0yj2sn 253 22 in in IN cord-276598-tm0yj2sn 253 23 the the DT cord-276598-tm0yj2sn 253 24 range range NN cord-276598-tm0yj2sn 253 25 of of IN cord-276598-tm0yj2sn 253 26 53 53 CD cord-276598-tm0yj2sn 253 27 - - SYM cord-276598-tm0yj2sn 253 28 93 93 CD cord-276598-tm0yj2sn 253 29 % % NN cord-276598-tm0yj2sn 253 30 . . . cord-276598-tm0yj2sn 254 1 A a DT cord-276598-tm0yj2sn 254 2 similar similar JJ cord-276598-tm0yj2sn 254 3 chlorination chlorination NN cord-276598-tm0yj2sn 254 4 method method NN cord-276598-tm0yj2sn 254 5 reacting react VBG cord-276598-tm0yj2sn 254 6 an an DT cord-276598-tm0yj2sn 254 7 amine amine NN cord-276598-tm0yj2sn 254 8 ( ( -LRB- cord-276598-tm0yj2sn 254 9 e.g. e.g. RB cord-276598-tm0yj2sn 254 10 , , , cord-276598-tm0yj2sn 254 11 aniline aniline NN cord-276598-tm0yj2sn 254 12 , , , cord-276598-tm0yj2sn 254 13 hexylamine hexylamine NNP cord-276598-tm0yj2sn 254 14 , , , cord-276598-tm0yj2sn 254 15 diethylamine diethylamine NNP cord-276598-tm0yj2sn 254 16 , , , cord-276598-tm0yj2sn 254 17 and and CC cord-276598-tm0yj2sn 254 18 methanamine methanamine NN cord-276598-tm0yj2sn 254 19 ) ) -RRB- cord-276598-tm0yj2sn 254 20 with with IN cord-276598-tm0yj2sn 254 21 phosphoric phosphoric JJ cord-276598-tm0yj2sn 254 22 acid acid NN cord-276598-tm0yj2sn 254 23 ( ( -LRB- cord-276598-tm0yj2sn 254 24 ( ( -LRB- cord-276598-tm0yj2sn 254 25 R R NNP cord-276598-tm0yj2sn 254 26 2 2 CD cord-276598-tm0yj2sn 254 27 P(O)OH p(o)oh NN cord-276598-tm0yj2sn 254 28 ; ; : cord-276598-tm0yj2sn 254 29 R r NN cord-276598-tm0yj2sn 254 30 = = SYM cord-276598-tm0yj2sn 254 31 OEt OEt NNS cord-276598-tm0yj2sn 254 32 , , , cord-276598-tm0yj2sn 254 33 OBu OBu NNS cord-276598-tm0yj2sn 254 34 , , , cord-276598-tm0yj2sn 254 35 OBn OBn NNS cord-276598-tm0yj2sn 254 36 ) ) -RRB- cord-276598-tm0yj2sn 254 37 in in IN cord-276598-tm0yj2sn 254 38 the the DT cord-276598-tm0yj2sn 254 39 presence presence NN cord-276598-tm0yj2sn 254 40 of of IN cord-276598-tm0yj2sn 254 41 triphenylphosphine triphenylphosphine NN cord-276598-tm0yj2sn 254 42 and and CC cord-276598-tm0yj2sn 254 43 CCl CCl NNS cord-276598-tm0yj2sn 254 44 4 4 CD cord-276598-tm0yj2sn 254 45 was be VBD cord-276598-tm0yj2sn 254 46 also also RB cord-276598-tm0yj2sn 254 47 used use VBN cord-276598-tm0yj2sn 254 48 to to TO cord-276598-tm0yj2sn 254 49 synthesize synthesize VB cord-276598-tm0yj2sn 254 50 P p NN cord-276598-tm0yj2sn 254 51 - - HYPH cord-276598-tm0yj2sn 254 52 Ns Ns NNP cord-276598-tm0yj2sn 254 53 ( ( -LRB- cord-276598-tm0yj2sn 254 54 Scheme scheme NN cord-276598-tm0yj2sn 254 55 6d 6d CD cord-276598-tm0yj2sn 254 56 ) ) -RRB- cord-276598-tm0yj2sn 255 1 [ [ -LRB- cord-276598-tm0yj2sn 255 2 86 86 CD cord-276598-tm0yj2sn 255 3 ] ] -RRB- cord-276598-tm0yj2sn 255 4 . . . cord-276598-tm0yj2sn 256 1 The the DT cord-276598-tm0yj2sn 256 2 isolated isolated JJ cord-276598-tm0yj2sn 256 3 yields yield NNS cord-276598-tm0yj2sn 256 4 of of IN cord-276598-tm0yj2sn 256 5 the the DT cord-276598-tm0yj2sn 256 6 products product NNS cord-276598-tm0yj2sn 256 7 in in IN cord-276598-tm0yj2sn 256 8 this this DT cord-276598-tm0yj2sn 256 9 case case NN cord-276598-tm0yj2sn 256 10 were be VBD cord-276598-tm0yj2sn 256 11 in in IN cord-276598-tm0yj2sn 256 12 the the DT cord-276598-tm0yj2sn 256 13 range range NN cord-276598-tm0yj2sn 256 14 of of IN cord-276598-tm0yj2sn 256 15 30 30 CD cord-276598-tm0yj2sn 256 16 - - SYM cord-276598-tm0yj2sn 256 17 75 75 CD cord-276598-tm0yj2sn 256 18 % % NN cord-276598-tm0yj2sn 256 19 . . . cord-276598-tm0yj2sn 257 1 P p NN cord-276598-tm0yj2sn 257 2 - - HYPH cord-276598-tm0yj2sn 257 3 N n CD cord-276598-tm0yj2sn 257 4 synthesis synthesis NN cord-276598-tm0yj2sn 257 5 via via IN cord-276598-tm0yj2sn 257 6 oxidative oxidative JJ cord-276598-tm0yj2sn 257 7 cross cross NN cord-276598-tm0yj2sn 257 8 - - NN cord-276598-tm0yj2sn 257 9 coupling coupling JJ cord-276598-tm0yj2sn 257 10 using use VBG cord-276598-tm0yj2sn 257 11 chlorinating chlorinate VBG cord-276598-tm0yj2sn 257 12 agents agent NNS cord-276598-tm0yj2sn 257 13 offers offer VBZ cord-276598-tm0yj2sn 257 14 a a DT cord-276598-tm0yj2sn 257 15 short short JJ cord-276598-tm0yj2sn 257 16 reaction reaction NN cord-276598-tm0yj2sn 257 17 time time NN cord-276598-tm0yj2sn 257 18 , , , cord-276598-tm0yj2sn 257 19 low low JJ cord-276598-tm0yj2sn 257 20 temperature temperature NN cord-276598-tm0yj2sn 257 21 synthesis synthesis NN cord-276598-tm0yj2sn 257 22 , , , cord-276598-tm0yj2sn 257 23 and and CC cord-276598-tm0yj2sn 257 24 a a DT cord-276598-tm0yj2sn 257 25 diverse diverse JJ cord-276598-tm0yj2sn 257 26 choice choice NN cord-276598-tm0yj2sn 257 27 of of IN cord-276598-tm0yj2sn 257 28 phosphorylating phosphorylate VBG cord-276598-tm0yj2sn 257 29 reagents reagent NNS cord-276598-tm0yj2sn 257 30 . . . cord-276598-tm0yj2sn 258 1 Nevertheless nevertheless RB cord-276598-tm0yj2sn 258 2 , , , cord-276598-tm0yj2sn 258 3 the the DT cord-276598-tm0yj2sn 258 4 methods method NNS cord-276598-tm0yj2sn 258 5 use use VBP cord-276598-tm0yj2sn 258 6 hazardous hazardous JJ cord-276598-tm0yj2sn 258 7 chlorinating chlorinating NN cord-276598-tm0yj2sn 258 8 agents agent NNS cord-276598-tm0yj2sn 258 9 such such JJ cord-276598-tm0yj2sn 258 10 as as IN cord-276598-tm0yj2sn 258 11 CCl CCl NNS cord-276598-tm0yj2sn 258 12 4 4 CD cord-276598-tm0yj2sn 258 13 and and CC cord-276598-tm0yj2sn 258 14 Cl Cl NNP cord-276598-tm0yj2sn 258 15 3 3 CD cord-276598-tm0yj2sn 258 16 CCN CCN NNP cord-276598-tm0yj2sn 258 17 , , , cord-276598-tm0yj2sn 258 18 generate generate VB cord-276598-tm0yj2sn 258 19 large large JJ cord-276598-tm0yj2sn 258 20 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 258 21 wastes waste NNS cord-276598-tm0yj2sn 258 22 , , , cord-276598-tm0yj2sn 258 23 and and CC cord-276598-tm0yj2sn 258 24 involve involve VBP cord-276598-tm0yj2sn 258 25 a a DT cord-276598-tm0yj2sn 258 26 pre pre JJ cord-276598-tm0yj2sn 258 27 - - NN cord-276598-tm0yj2sn 258 28 functionalization functionalization JJ cord-276598-tm0yj2sn 258 29 step step NN cord-276598-tm0yj2sn 258 30 in in IN cord-276598-tm0yj2sn 258 31 the the DT cord-276598-tm0yj2sn 258 32 synthetic synthetic JJ cord-276598-tm0yj2sn 258 33 process process NN cord-276598-tm0yj2sn 258 34 . . . cord-276598-tm0yj2sn 259 1 The the DT cord-276598-tm0yj2sn 259 2 synthesis synthesis NN cord-276598-tm0yj2sn 259 3 of of IN cord-276598-tm0yj2sn 259 4 P p NN cord-276598-tm0yj2sn 259 5 - - HYPH cord-276598-tm0yj2sn 259 6 Ns Ns NNP cord-276598-tm0yj2sn 259 7 from from IN cord-276598-tm0yj2sn 259 8 amines amine NNS cord-276598-tm0yj2sn 259 9 ( ( -LRB- cord-276598-tm0yj2sn 259 10 aromatic aromatic JJ cord-276598-tm0yj2sn 259 11 and and CC cord-276598-tm0yj2sn 259 12 aliphatic aliphatic JJ cord-276598-tm0yj2sn 259 13 ) ) -RRB- cord-276598-tm0yj2sn 259 14 and and CC cord-276598-tm0yj2sn 259 15 symmetrical symmetrical JJ cord-276598-tm0yj2sn 259 16 trialkyl trialkyl NN cord-276598-tm0yj2sn 259 17 phosphite phosphite NNP cord-276598-tm0yj2sn 259 18 ( ( -LRB- cord-276598-tm0yj2sn 259 19 P(OR P(OR NNP cord-276598-tm0yj2sn 260 1 ) ) -RRB- cord-276598-tm0yj2sn 260 2 3 3 LS cord-276598-tm0yj2sn 260 3 ; ; : cord-276598-tm0yj2sn 260 4 R= R= VBZ cord-276598-tm0yj2sn 260 5 Me -PRON- PRP cord-276598-tm0yj2sn 260 6 , , , cord-276598-tm0yj2sn 260 7 Et Et NNP cord-276598-tm0yj2sn 260 8 , , , cord-276598-tm0yj2sn 260 9 i i NN cord-276598-tm0yj2sn 260 10 - - HYPH cord-276598-tm0yj2sn 260 11 Pr Pr NNP cord-276598-tm0yj2sn 260 12 ) ) -RRB- cord-276598-tm0yj2sn 260 13 in in IN cord-276598-tm0yj2sn 260 14 the the DT cord-276598-tm0yj2sn 260 15 presence presence NN cord-276598-tm0yj2sn 260 16 I -PRON- PRP cord-276598-tm0yj2sn 260 17 2 2 CD cord-276598-tm0yj2sn 260 18 was be VBD cord-276598-tm0yj2sn 260 19 reported report VBN cord-276598-tm0yj2sn 260 20 by by IN cord-276598-tm0yj2sn 260 21 Chen Chen NNP cord-276598-tm0yj2sn 260 22 et et NNP cord-276598-tm0yj2sn 260 23 al al NNP cord-276598-tm0yj2sn 260 24 . . . cord-276598-tm0yj2sn 261 1 [ [ -LRB- cord-276598-tm0yj2sn 261 2 100 100 CD cord-276598-tm0yj2sn 261 3 ] ] -RRB- cord-276598-tm0yj2sn 261 4 . . . cord-276598-tm0yj2sn 262 1 Crude crude JJ cord-276598-tm0yj2sn 262 2 products product NNS cord-276598-tm0yj2sn 262 3 were be VBD cord-276598-tm0yj2sn 262 4 purified purify VBN cord-276598-tm0yj2sn 262 5 by by IN cord-276598-tm0yj2sn 262 6 column column NN cord-276598-tm0yj2sn 262 7 chromatography chromatography NN cord-276598-tm0yj2sn 262 8 ( ( -LRB- cord-276598-tm0yj2sn 262 9 on on IN cord-276598-tm0yj2sn 262 10 silica silica NN cord-276598-tm0yj2sn 262 11 ) ) -RRB- cord-276598-tm0yj2sn 262 12 and and CC cord-276598-tm0yj2sn 262 13 resulted result VBD cord-276598-tm0yj2sn 262 14 in in IN cord-276598-tm0yj2sn 262 15 yields yield NNS cord-276598-tm0yj2sn 262 16 in in IN cord-276598-tm0yj2sn 262 17 the the DT cord-276598-tm0yj2sn 262 18 range range NN cord-276598-tm0yj2sn 262 19 of of IN cord-276598-tm0yj2sn 262 20 0 0 CD cord-276598-tm0yj2sn 262 21 - - SYM cord-276598-tm0yj2sn 262 22 95 95 CD cord-276598-tm0yj2sn 262 23 % % NN cord-276598-tm0yj2sn 262 24 . . . cord-276598-tm0yj2sn 263 1 For for IN cord-276598-tm0yj2sn 263 2 the the DT cord-276598-tm0yj2sn 263 3 low low JJ cord-276598-tm0yj2sn 263 4 yielding yield VBG cord-276598-tm0yj2sn 263 5 derivatives derivative NNS cord-276598-tm0yj2sn 263 6 , , , cord-276598-tm0yj2sn 263 7 the the DT cord-276598-tm0yj2sn 263 8 reaction reaction NN cord-276598-tm0yj2sn 263 9 was be VBD cord-276598-tm0yj2sn 263 10 more more RBR cord-276598-tm0yj2sn 263 11 selective selective JJ cord-276598-tm0yj2sn 263 12 to to IN cord-276598-tm0yj2sn 263 13 three three CD cord-276598-tm0yj2sn 263 14 identified identify VBN cord-276598-tm0yj2sn 263 15 by by IN cord-276598-tm0yj2sn 263 16 - - HYPH cord-276598-tm0yj2sn 263 17 products product NNS cord-276598-tm0yj2sn 263 18 , , , cord-276598-tm0yj2sn 263 19 H H NNP cord-276598-tm0yj2sn 263 20 - - HYPH cord-276598-tm0yj2sn 263 21 phosphonate phosphonate NNP cord-276598-tm0yj2sn 263 22 , , , cord-276598-tm0yj2sn 263 23 trialkyl trialkyl JJ cord-276598-tm0yj2sn 263 24 phosphate phosphate NN cord-276598-tm0yj2sn 263 25 , , , cord-276598-tm0yj2sn 263 26 and and CC cord-276598-tm0yj2sn 263 27 tetraalkyl tetraalkyl NN cord-276598-tm0yj2sn 263 28 diphosphate diphosphate NN cord-276598-tm0yj2sn 263 29 , , , cord-276598-tm0yj2sn 263 30 as as RB cord-276598-tm0yj2sn 263 31 well well RB cord-276598-tm0yj2sn 263 32 as as IN cord-276598-tm0yj2sn 263 33 some some DT cord-276598-tm0yj2sn 263 34 other other JJ cord-276598-tm0yj2sn 263 35 unidentified unidentified JJ cord-276598-tm0yj2sn 263 36 by by IN cord-276598-tm0yj2sn 263 37 - - HYPH cord-276598-tm0yj2sn 263 38 products product NNS cord-276598-tm0yj2sn 263 39 . . . cord-276598-tm0yj2sn 264 1 Important important JJ cord-276598-tm0yj2sn 264 2 compounds compound NNS cord-276598-tm0yj2sn 264 3 such such JJ cord-276598-tm0yj2sn 264 4 as as IN cord-276598-tm0yj2sn 264 5 phosphoryl phosphoryl NN cord-276598-tm0yj2sn 264 6 amino amino NN cord-276598-tm0yj2sn 264 7 acid acid NN cord-276598-tm0yj2sn 264 8 esters ester NNS cord-276598-tm0yj2sn 264 9 ( ( -LRB- cord-276598-tm0yj2sn 264 10 8) 8) NNP cord-276598-tm0yj2sn 264 11 ( ( -LRB- cord-276598-tm0yj2sn 264 12 9 9 CD cord-276598-tm0yj2sn 264 13 ) ) -RRB- cord-276598-tm0yj2sn 264 14 ( ( -LRB- cord-276598-tm0yj2sn 264 15 10 10 CD cord-276598-tm0yj2sn 264 16 ) ) -RRB- cord-276598-tm0yj2sn 264 17 ( ( -LRB- cord-276598-tm0yj2sn 264 18 11 11 CD cord-276598-tm0yj2sn 264 19 ) ) -RRB- cord-276598-tm0yj2sn 264 20 were be VBD cord-276598-tm0yj2sn 264 21 synthesized synthesize VBN cord-276598-tm0yj2sn 264 22 using use VBG cord-276598-tm0yj2sn 264 23 the the DT cord-276598-tm0yj2sn 264 24 iodine iodine NN cord-276598-tm0yj2sn 264 25 - - HYPH cord-276598-tm0yj2sn 264 26 mediated mediate VBN cord-276598-tm0yj2sn 264 27 method method NN cord-276598-tm0yj2sn 264 28 ( ( -LRB- cord-276598-tm0yj2sn 264 29 Figure figure NN cord-276598-tm0yj2sn 264 30 5 5 CD cord-276598-tm0yj2sn 264 31 ) ) -RRB- cord-276598-tm0yj2sn 264 32 . . . cord-276598-tm0yj2sn 265 1 Molecules molecule NNS cord-276598-tm0yj2sn 265 2 2020 2020 CD cord-276598-tm0yj2sn 265 3 , , , cord-276598-tm0yj2sn 265 4 25 25 CD cord-276598-tm0yj2sn 265 5 , , , cord-276598-tm0yj2sn 265 6 x x NN cord-276598-tm0yj2sn 265 7 FOR for IN cord-276598-tm0yj2sn 265 8 PEER PEER NNP cord-276598-tm0yj2sn 265 9 REVIEW REVIEW NNP cord-276598-tm0yj2sn 265 10 10 10 CD cord-276598-tm0yj2sn 265 11 of of IN cord-276598-tm0yj2sn 265 12 37 37 CD cord-276598-tm0yj2sn 265 13 by by IN cord-276598-tm0yj2sn 265 14 - - HYPH cord-276598-tm0yj2sn 265 15 products product NNS cord-276598-tm0yj2sn 265 16 . . . cord-276598-tm0yj2sn 266 1 Important important JJ cord-276598-tm0yj2sn 266 2 compounds compound NNS cord-276598-tm0yj2sn 266 3 such such JJ cord-276598-tm0yj2sn 266 4 as as IN cord-276598-tm0yj2sn 266 5 phosphoryl phosphoryl NN cord-276598-tm0yj2sn 266 6 amino amino NN cord-276598-tm0yj2sn 266 7 acid acid NN cord-276598-tm0yj2sn 266 8 esters ester NNS cord-276598-tm0yj2sn 266 9 ( ( -LRB- cord-276598-tm0yj2sn 266 10 8) 8) NNP cord-276598-tm0yj2sn 266 11 ( ( -LRB- cord-276598-tm0yj2sn 266 12 9 9 CD cord-276598-tm0yj2sn 266 13 ) ) -RRB- cord-276598-tm0yj2sn 266 14 ( ( -LRB- cord-276598-tm0yj2sn 266 15 10 10 CD cord-276598-tm0yj2sn 266 16 ) ) -RRB- cord-276598-tm0yj2sn 266 17 ( ( -LRB- cord-276598-tm0yj2sn 266 18 11 11 CD cord-276598-tm0yj2sn 266 19 ) ) -RRB- cord-276598-tm0yj2sn 266 20 were be VBD cord-276598-tm0yj2sn 266 21 synthesized synthesize VBN cord-276598-tm0yj2sn 266 22 using use VBG cord-276598-tm0yj2sn 266 23 the the DT cord-276598-tm0yj2sn 266 24 iodine iodine NN cord-276598-tm0yj2sn 266 25 - - HYPH cord-276598-tm0yj2sn 266 26 mediated mediate VBN cord-276598-tm0yj2sn 266 27 method method NN cord-276598-tm0yj2sn 266 28 ( ( -LRB- cord-276598-tm0yj2sn 266 29 Figure figure NN cord-276598-tm0yj2sn 266 30 5 5 CD cord-276598-tm0yj2sn 266 31 ) ) -RRB- cord-276598-tm0yj2sn 266 32 . . . cord-276598-tm0yj2sn 267 1 Structures structure NNS cord-276598-tm0yj2sn 267 2 ( ( -LRB- cord-276598-tm0yj2sn 267 3 11 11 CD cord-276598-tm0yj2sn 267 4 ) ) -RRB- cord-276598-tm0yj2sn 267 5 synthesized synthesize VBN cord-276598-tm0yj2sn 267 6 by by IN cord-276598-tm0yj2sn 267 7 iodinating iodinate VBG cord-276598-tm0yj2sn 267 8 agents agent NNS cord-276598-tm0yj2sn 267 9 . . . cord-276598-tm0yj2sn 268 1 Iodine iodine NN cord-276598-tm0yj2sn 268 2 ( ( -LRB- cord-276598-tm0yj2sn 268 3 I2 I2 NNP cord-276598-tm0yj2sn 268 4 ) ) -RRB- cord-276598-tm0yj2sn 268 5 has have VBZ cord-276598-tm0yj2sn 268 6 also also RB cord-276598-tm0yj2sn 268 7 been be VBN cord-276598-tm0yj2sn 268 8 used use VBN cord-276598-tm0yj2sn 268 9 as as IN cord-276598-tm0yj2sn 268 10 a a DT cord-276598-tm0yj2sn 268 11 catalyst catalyst NN cord-276598-tm0yj2sn 268 12 under under IN cord-276598-tm0yj2sn 268 13 solvent solvent NN cord-276598-tm0yj2sn 268 14 - - HYPH cord-276598-tm0yj2sn 268 15 free free JJ cord-276598-tm0yj2sn 268 16 conditions condition NNS cord-276598-tm0yj2sn 268 17 to to IN cord-276598-tm0yj2sn 268 18 couple couple NN cord-276598-tm0yj2sn 268 19 aryl aryl NN cord-276598-tm0yj2sn 268 20 amines amine NNS cord-276598-tm0yj2sn 268 21 ( ( -LRB- cord-276598-tm0yj2sn 268 22 PhNH2 phnh2 NN cord-276598-tm0yj2sn 268 23 and and CC cord-276598-tm0yj2sn 268 24 derivatives derivative NNS cord-276598-tm0yj2sn 268 25 containing contain VBG cord-276598-tm0yj2sn 268 26 OH oh UH cord-276598-tm0yj2sn 268 27 , , , cord-276598-tm0yj2sn 268 28 OEt OEt NNS cord-276598-tm0yj2sn 268 29 , , , cord-276598-tm0yj2sn 268 30 CN CN NNP cord-276598-tm0yj2sn 268 31 , , , cord-276598-tm0yj2sn 268 32 OMe OMe NNS cord-276598-tm0yj2sn 268 33 , , , cord-276598-tm0yj2sn 268 34 NO2 NO2 NNP cord-276598-tm0yj2sn 268 35 , , , cord-276598-tm0yj2sn 268 36 F F NNP cord-276598-tm0yj2sn 268 37 , , , cord-276598-tm0yj2sn 268 38 Cl Cl NNP cord-276598-tm0yj2sn 268 39 , , , cord-276598-tm0yj2sn 268 40 or or CC cord-276598-tm0yj2sn 268 41 Br Br NNP cord-276598-tm0yj2sn 268 42 substituents substituent NNS cord-276598-tm0yj2sn 268 43 on on IN cord-276598-tm0yj2sn 268 44 Ph Ph NNP cord-276598-tm0yj2sn 268 45 ) ) -RRB- cord-276598-tm0yj2sn 268 46 with with IN cord-276598-tm0yj2sn 268 47 ( ( -LRB- cord-276598-tm0yj2sn 268 48 RO)2P(O)H RO)2P(O)H NNP cord-276598-tm0yj2sn 268 49 ( ( -LRB- cord-276598-tm0yj2sn 268 50 dialkyl dialkyl NNP cord-276598-tm0yj2sn 268 51 H H NNP cord-276598-tm0yj2sn 268 52 - - HYPH cord-276598-tm0yj2sn 268 53 P p NN cord-276598-tm0yj2sn 268 54 ; ; : cord-276598-tm0yj2sn 268 55 R r NN cord-276598-tm0yj2sn 268 56 = = NN cord-276598-tm0yj2sn 269 1 Me -PRON- PRP cord-276598-tm0yj2sn 269 2 , , , cord-276598-tm0yj2sn 269 3 Et Et NNP cord-276598-tm0yj2sn 269 4 ) ) -RRB- cord-276598-tm0yj2sn 269 5 affording afford VBG cord-276598-tm0yj2sn 269 6 dialkyl dialkyl NN cord-276598-tm0yj2sn 269 7 P P NNP cord-276598-tm0yj2sn 269 8 - - HYPH cord-276598-tm0yj2sn 269 9 Ns Ns NNP cord-276598-tm0yj2sn 269 10 ( ( -LRB- cord-276598-tm0yj2sn 269 11 Scheme scheme NN cord-276598-tm0yj2sn 269 12 7b 7b CD cord-276598-tm0yj2sn 269 13 ) ) -RRB- cord-276598-tm0yj2sn 269 14 [ [ -LRB- cord-276598-tm0yj2sn 269 15 101 101 CD cord-276598-tm0yj2sn 269 16 ] ] -RRB- cord-276598-tm0yj2sn 269 17 . . . cord-276598-tm0yj2sn 270 1 Then then RB cord-276598-tm0yj2sn 270 2 , , , cord-276598-tm0yj2sn 270 3 the the DT cord-276598-tm0yj2sn 270 4 crude crude JJ cord-276598-tm0yj2sn 270 5 products product NNS cord-276598-tm0yj2sn 270 6 were be VBD cord-276598-tm0yj2sn 270 7 purified purify VBN cord-276598-tm0yj2sn 270 8 by by IN cord-276598-tm0yj2sn 270 9 column column NN cord-276598-tm0yj2sn 270 10 chromatography chromatography NN cord-276598-tm0yj2sn 270 11 ( ( -LRB- cord-276598-tm0yj2sn 270 12 on on IN cord-276598-tm0yj2sn 270 13 silica silica NN cord-276598-tm0yj2sn 270 14 ) ) -RRB- cord-276598-tm0yj2sn 270 15 to to TO cord-276598-tm0yj2sn 270 16 obtain obtain VB cord-276598-tm0yj2sn 270 17 yields yield NNS cord-276598-tm0yj2sn 270 18 of of IN cord-276598-tm0yj2sn 270 19 product product NN cord-276598-tm0yj2sn 270 20 in in IN cord-276598-tm0yj2sn 270 21 0 0 CD cord-276598-tm0yj2sn 270 22 - - SYM cord-276598-tm0yj2sn 270 23 88 88 CD cord-276598-tm0yj2sn 270 24 % % NN cord-276598-tm0yj2sn 270 25 . . . cord-276598-tm0yj2sn 271 1 The the DT cord-276598-tm0yj2sn 271 2 best good JJS cord-276598-tm0yj2sn 271 3 yielding yielding JJ cord-276598-tm0yj2sn 271 4 conditions condition NNS cord-276598-tm0yj2sn 271 5 were be VBD cord-276598-tm0yj2sn 271 6 shorter short JJR cord-276598-tm0yj2sn 271 7 reaction reaction NN cord-276598-tm0yj2sn 271 8 times time NNS cord-276598-tm0yj2sn 271 9 without without IN cord-276598-tm0yj2sn 271 10 solvent solvent NN cord-276598-tm0yj2sn 271 11 . . . cord-276598-tm0yj2sn 272 1 Reactions reaction NNS cord-276598-tm0yj2sn 272 2 performed perform VBN cord-276598-tm0yj2sn 272 3 in in IN cord-276598-tm0yj2sn 272 4 polar polar JJ cord-276598-tm0yj2sn 272 5 non non JJ cord-276598-tm0yj2sn 272 6 - - JJ cord-276598-tm0yj2sn 272 7 protic protic JJ cord-276598-tm0yj2sn 272 8 solvents solvent NNS cord-276598-tm0yj2sn 272 9 ( ( -LRB- cord-276598-tm0yj2sn 272 10 e.g. e.g. RB cord-276598-tm0yj2sn 272 11 , , , cord-276598-tm0yj2sn 272 12 CH2Cl2 ch2cl2 NN cord-276598-tm0yj2sn 272 13 ) ) -RRB- cord-276598-tm0yj2sn 272 14 , , , cord-276598-tm0yj2sn 272 15 non non JJ cord-276598-tm0yj2sn 272 16 - - JJ cord-276598-tm0yj2sn 272 17 polar polar JJ cord-276598-tm0yj2sn 272 18 solvents solvent NNS cord-276598-tm0yj2sn 272 19 ( ( -LRB- cord-276598-tm0yj2sn 272 20 e.g. e.g. RB cord-276598-tm0yj2sn 272 21 , , , cord-276598-tm0yj2sn 272 22 hexane hexane NNP cord-276598-tm0yj2sn 272 23 ) ) -RRB- cord-276598-tm0yj2sn 272 24 , , , cord-276598-tm0yj2sn 272 25 or or CC cord-276598-tm0yj2sn 272 26 protic protic JJ cord-276598-tm0yj2sn 272 27 solvents solvent NNS cord-276598-tm0yj2sn 272 28 ( ( -LRB- cord-276598-tm0yj2sn 272 29 e.g. e.g. RB cord-276598-tm0yj2sn 272 30 , , , cord-276598-tm0yj2sn 272 31 MeOH MeOH NNP cord-276598-tm0yj2sn 272 32 ) ) -RRB- cord-276598-tm0yj2sn 272 33 all all DT cord-276598-tm0yj2sn 272 34 suffered suffer VBD cord-276598-tm0yj2sn 272 35 from from IN cord-276598-tm0yj2sn 272 36 reduced reduced JJ cord-276598-tm0yj2sn 272 37 efficiency efficiency NN cord-276598-tm0yj2sn 272 38 and and CC cord-276598-tm0yj2sn 272 39 selectivity selectivity NN cord-276598-tm0yj2sn 272 40 . . . cord-276598-tm0yj2sn 273 1 Furthermore furthermore RB cord-276598-tm0yj2sn 273 2 , , , cord-276598-tm0yj2sn 273 3 aniline aniline NN cord-276598-tm0yj2sn 273 4 with with IN cord-276598-tm0yj2sn 273 5 substituents substituent NNS cord-276598-tm0yj2sn 273 6 at at IN cord-276598-tm0yj2sn 273 7 ortho ortho NNP cord-276598-tm0yj2sn 273 8 - - HYPH cord-276598-tm0yj2sn 273 9 and and CC cord-276598-tm0yj2sn 273 10 meta meta NNP cord-276598-tm0yj2sn 273 11 - - HYPH cord-276598-tm0yj2sn 273 12 positions position NNS cord-276598-tm0yj2sn 273 13 were be VBD cord-276598-tm0yj2sn 273 14 observed observe VBN cord-276598-tm0yj2sn 273 15 to to TO cord-276598-tm0yj2sn 273 16 have have VB cord-276598-tm0yj2sn 273 17 reacted react VBN cord-276598-tm0yj2sn 273 18 faster fast RBR cord-276598-tm0yj2sn 273 19 and and CC cord-276598-tm0yj2sn 273 20 were be VBD cord-276598-tm0yj2sn 273 21 higher high JJR cord-276598-tm0yj2sn 273 22 yielding yield VBG cord-276598-tm0yj2sn 273 23 than than IN cord-276598-tm0yj2sn 273 24 aniline aniline NN cord-276598-tm0yj2sn 273 25 containing contain VBG cord-276598-tm0yj2sn 273 26 substituents substituent NNS cord-276598-tm0yj2sn 273 27 at at IN cord-276598-tm0yj2sn 273 28 the the DT cord-276598-tm0yj2sn 273 29 para para NNP cord-276598-tm0yj2sn 273 30 - - HYPH cord-276598-tm0yj2sn 273 31 position position NN cord-276598-tm0yj2sn 273 32 . . . cord-276598-tm0yj2sn 274 1 I2 I2 NNP cord-276598-tm0yj2sn 274 2 was be VBD cord-276598-tm0yj2sn 274 3 used use VBN cord-276598-tm0yj2sn 274 4 in in IN cord-276598-tm0yj2sn 274 5 the the DT cord-276598-tm0yj2sn 274 6 presence presence NN cord-276598-tm0yj2sn 274 7 of of IN cord-276598-tm0yj2sn 274 8 H2O2 H2O2 NNP cord-276598-tm0yj2sn 274 9 as as IN cord-276598-tm0yj2sn 274 10 a a DT cord-276598-tm0yj2sn 274 11 catalyst catalyst NN cord-276598-tm0yj2sn 274 12 at at IN cord-276598-tm0yj2sn 274 13 20 20 CD cord-276598-tm0yj2sn 274 14 ° ° NN cord-276598-tm0yj2sn 274 15 C c NN cord-276598-tm0yj2sn 274 16 for for IN cord-276598-tm0yj2sn 274 17 the the DT cord-276598-tm0yj2sn 274 18 dehydrogenative dehydrogenative JJ cord-276598-tm0yj2sn 274 19 cross cross NN cord-276598-tm0yj2sn 274 20 - - NN cord-276598-tm0yj2sn 274 21 coupling coupling NN cord-276598-tm0yj2sn 274 22 of of IN cord-276598-tm0yj2sn 274 23 diethyl diethyl NNP cord-276598-tm0yj2sn 274 24 H H NNP cord-276598-tm0yj2sn 274 25 - - HYPH cord-276598-tm0yj2sn 274 26 P p NN cord-276598-tm0yj2sn 274 27 and and CC cord-276598-tm0yj2sn 274 28 amine amine NN cord-276598-tm0yj2sn 274 29 or or CC cord-276598-tm0yj2sn 274 30 sulfoximines sulfoximine NNS cord-276598-tm0yj2sn 274 31 to to TO cord-276598-tm0yj2sn 274 32 form form VB cord-276598-tm0yj2sn 274 33 P p NN cord-276598-tm0yj2sn 274 34 - - HYPH cord-276598-tm0yj2sn 274 35 Ns Ns NNP cord-276598-tm0yj2sn 274 36 ( ( -LRB- cord-276598-tm0yj2sn 274 37 Scheme scheme NN cord-276598-tm0yj2sn 274 38 7c 7c CD cord-276598-tm0yj2sn 274 39 ) ) -RRB- cord-276598-tm0yj2sn 274 40 [ [ -LRB- cord-276598-tm0yj2sn 274 41 102 102 CD cord-276598-tm0yj2sn 274 42 ] ] -RRB- cord-276598-tm0yj2sn 274 43 . . . cord-276598-tm0yj2sn 275 1 Purification purification NN cord-276598-tm0yj2sn 275 2 of of IN cord-276598-tm0yj2sn 275 3 the the DT cord-276598-tm0yj2sn 275 4 products product NNS cord-276598-tm0yj2sn 275 5 by by IN cord-276598-tm0yj2sn 275 6 column column NN cord-276598-tm0yj2sn 275 7 chromatography chromatography NN cord-276598-tm0yj2sn 275 8 ( ( -LRB- cord-276598-tm0yj2sn 275 9 on on IN cord-276598-tm0yj2sn 275 10 silica silica NN cord-276598-tm0yj2sn 275 11 ) ) -RRB- cord-276598-tm0yj2sn 275 12 afforded afford VBN cord-276598-tm0yj2sn 275 13 P p NN cord-276598-tm0yj2sn 275 14 - - HYPH cord-276598-tm0yj2sn 275 15 Ns Ns NNP cord-276598-tm0yj2sn 275 16 with with IN cord-276598-tm0yj2sn 275 17 isolated isolated JJ cord-276598-tm0yj2sn 275 18 yields yield NNS cord-276598-tm0yj2sn 275 19 of of IN cord-276598-tm0yj2sn 275 20 31 31 CD cord-276598-tm0yj2sn 275 21 - - SYM cord-276598-tm0yj2sn 275 22 96 96 CD cord-276598-tm0yj2sn 275 23 % % NN cord-276598-tm0yj2sn 275 24 , , , cord-276598-tm0yj2sn 275 25 with with IN cord-276598-tm0yj2sn 275 26 the the DT cord-276598-tm0yj2sn 275 27 lower lower RBR cord-276598-tm0yj2sn 275 28 yielding yield VBG cord-276598-tm0yj2sn 275 29 products product NNS cord-276598-tm0yj2sn 275 30 reported report VBN cord-276598-tm0yj2sn 275 31 from from IN cord-276598-tm0yj2sn 275 32 sulfoximine sulfoximine NNP cord-276598-tm0yj2sn 275 33 . . . cord-276598-tm0yj2sn 276 1 Both both DT cord-276598-tm0yj2sn 276 2 alkyl alkyl NN cord-276598-tm0yj2sn 276 3 and and CC cord-276598-tm0yj2sn 276 4 aryl aryl NN cord-276598-tm0yj2sn 276 5 H H NNP cord-276598-tm0yj2sn 276 6 - - HYPH cord-276598-tm0yj2sn 276 7 P p NN cord-276598-tm0yj2sn 276 8 ( ( -LRB- cord-276598-tm0yj2sn 276 9 ( ( -LRB- cord-276598-tm0yj2sn 276 10 RO)2P(O)H RO)2P(O)H NNP cord-276598-tm0yj2sn 276 11 , , , cord-276598-tm0yj2sn 276 12 R r NN cord-276598-tm0yj2sn 276 13 = = FW cord-276598-tm0yj2sn 276 14 Et et NN cord-276598-tm0yj2sn 276 15 , , , cord-276598-tm0yj2sn 276 16 i i NN cord-276598-tm0yj2sn 276 17 - - HYPH cord-276598-tm0yj2sn 276 18 Pr Pr NNP cord-276598-tm0yj2sn 276 19 , , , cord-276598-tm0yj2sn 276 20 Ph Ph NNP cord-276598-tm0yj2sn 276 21 ) ) -RRB- cord-276598-tm0yj2sn 276 22 were be VBD cord-276598-tm0yj2sn 276 23 used use VBN cord-276598-tm0yj2sn 276 24 as as IN cord-276598-tm0yj2sn 276 25 the the DT cord-276598-tm0yj2sn 276 26 substrate substrate NN cord-276598-tm0yj2sn 276 27 along along IN cord-276598-tm0yj2sn 276 28 with with IN cord-276598-tm0yj2sn 276 29 cyclic cyclic JJ cord-276598-tm0yj2sn 276 30 aromatic aromatic JJ cord-276598-tm0yj2sn 276 31 secondary secondary JJ cord-276598-tm0yj2sn 276 32 amines amine NNS cord-276598-tm0yj2sn 276 33 ( ( -LRB- cord-276598-tm0yj2sn 276 34 e.g. e.g. RB cord-276598-tm0yj2sn 276 35 , , , cord-276598-tm0yj2sn 276 36 indole indole NN cord-276598-tm0yj2sn 276 37 ) ) -RRB- cord-276598-tm0yj2sn 276 38 , , , cord-276598-tm0yj2sn 276 39 derivatives derivative NNS cord-276598-tm0yj2sn 276 40 of of IN cord-276598-tm0yj2sn 276 41 heterocyclic heterocyclic JJ cord-276598-tm0yj2sn 276 42 amines amine NNS cord-276598-tm0yj2sn 276 43 ( ( -LRB- cord-276598-tm0yj2sn 276 44 e.g. e.g. RB cord-276598-tm0yj2sn 276 45 , , , cord-276598-tm0yj2sn 276 46 furfurylamine furfurylamine NN cord-276598-tm0yj2sn 276 47 ) ) -RRB- cord-276598-tm0yj2sn 276 48 , , , cord-276598-tm0yj2sn 276 49 aliphatic aliphatic JJ cord-276598-tm0yj2sn 276 50 cyclic cyclic JJ cord-276598-tm0yj2sn 276 51 secondary secondary JJ cord-276598-tm0yj2sn 276 52 amines amine NNS cord-276598-tm0yj2sn 276 53 ( ( -LRB- cord-276598-tm0yj2sn 276 54 e.g. e.g. RB cord-276598-tm0yj2sn 276 55 , , , cord-276598-tm0yj2sn 276 56 1-benzhydrylpiperazine 1-benzhydrylpiperazine CD cord-276598-tm0yj2sn 276 57 ) ) -RRB- cord-276598-tm0yj2sn 277 1 , , , cord-276598-tm0yj2sn 277 2 tertiary tertiary JJ cord-276598-tm0yj2sn 277 3 amines amine NNS cord-276598-tm0yj2sn 277 4 ( ( -LRB- cord-276598-tm0yj2sn 277 5 e.g. e.g. RB cord-276598-tm0yj2sn 277 6 , , , cord-276598-tm0yj2sn 277 7 N N NNP cord-276598-tm0yj2sn 277 8 - - HYPH cord-276598-tm0yj2sn 277 9 methylhomopiperazine methylhomopiperazine NNP cord-276598-tm0yj2sn 277 10 ) ) -RRB- cord-276598-tm0yj2sn 277 11 , , , cord-276598-tm0yj2sn 277 12 or or CC cord-276598-tm0yj2sn 277 13 sulfoximine sulfoximine NNP cord-276598-tm0yj2sn 277 14 . . . cord-276598-tm0yj2sn 278 1 According accord VBG cord-276598-tm0yj2sn 278 2 to to IN cord-276598-tm0yj2sn 278 3 the the DT cord-276598-tm0yj2sn 278 4 article article NN cord-276598-tm0yj2sn 278 5 , , , cord-276598-tm0yj2sn 278 6 using use VBG cord-276598-tm0yj2sn 278 7 other other JJ cord-276598-tm0yj2sn 278 8 sources source NNS cord-276598-tm0yj2sn 278 9 of of IN cord-276598-tm0yj2sn 278 10 I2 I2 NNP cord-276598-tm0yj2sn 278 11 such such JJ cord-276598-tm0yj2sn 278 12 as as IN cord-276598-tm0yj2sn 278 13 KI KI NNP cord-276598-tm0yj2sn 278 14 or or CC cord-276598-tm0yj2sn 278 15 N N NNP cord-276598-tm0yj2sn 278 16 - - HYPH cord-276598-tm0yj2sn 278 17 bromosuccinimide bromosuccinimide NN cord-276598-tm0yj2sn 278 18 ( ( -LRB- cord-276598-tm0yj2sn 278 19 NBS NBS NNP cord-276598-tm0yj2sn 278 20 ) ) -RRB- cord-276598-tm0yj2sn 278 21 for for IN cord-276598-tm0yj2sn 278 22 the the DT cord-276598-tm0yj2sn 278 23 reaction reaction NN cord-276598-tm0yj2sn 278 24 resulted result VBD cord-276598-tm0yj2sn 278 25 in in IN cord-276598-tm0yj2sn 278 26 decreased decreased JJ cord-276598-tm0yj2sn 278 27 yield yield NN cord-276598-tm0yj2sn 278 28 and and CC cord-276598-tm0yj2sn 278 29 trace trace NN cord-276598-tm0yj2sn 278 30 quantities quantity NNS cord-276598-tm0yj2sn 278 31 of of IN cord-276598-tm0yj2sn 278 32 the the DT cord-276598-tm0yj2sn 278 33 desired desire VBN cord-276598-tm0yj2sn 278 34 products product NNS cord-276598-tm0yj2sn 278 35 , , , cord-276598-tm0yj2sn 278 36 respectively respectively RB cord-276598-tm0yj2sn 278 37 . . . cord-276598-tm0yj2sn 279 1 Iodine iodine NN cord-276598-tm0yj2sn 279 2 - - HYPH cord-276598-tm0yj2sn 279 3 mediated mediate VBN cord-276598-tm0yj2sn 279 4 oxidative oxidative JJ cord-276598-tm0yj2sn 279 5 cross cross JJ cord-276598-tm0yj2sn 279 6 - - JJ cord-276598-tm0yj2sn 279 7 coupling coupling JJ cord-276598-tm0yj2sn 279 8 methods method NNS cord-276598-tm0yj2sn 279 9 offer offer VBP cord-276598-tm0yj2sn 279 10 better well JJR cord-276598-tm0yj2sn 279 11 routes route NNS cord-276598-tm0yj2sn 279 12 to to IN cord-276598-tm0yj2sn 279 13 P P NNP cord-276598-tm0yj2sn 279 14 - - HYPH cord-276598-tm0yj2sn 279 15 N n CD cord-276598-tm0yj2sn 279 16 compounds compound NNS cord-276598-tm0yj2sn 279 17 by by IN cord-276598-tm0yj2sn 279 18 eliminating eliminate VBG cord-276598-tm0yj2sn 279 19 toxic toxic JJ cord-276598-tm0yj2sn 279 20 halogenating halogenating NN cord-276598-tm0yj2sn 279 21 agents agent NNS cord-276598-tm0yj2sn 279 22 such such JJ cord-276598-tm0yj2sn 279 23 as as IN cord-276598-tm0yj2sn 279 24 CCl4 ccl4 NN cord-276598-tm0yj2sn 279 25 in in IN cord-276598-tm0yj2sn 279 26 the the DT cord-276598-tm0yj2sn 279 27 synthetic synthetic JJ cord-276598-tm0yj2sn 279 28 processes process NNS cord-276598-tm0yj2sn 279 29 . . . cord-276598-tm0yj2sn 280 1 The the DT cord-276598-tm0yj2sn 280 2 method method NN cord-276598-tm0yj2sn 280 3 also also RB cord-276598-tm0yj2sn 280 4 uses use VBZ cord-276598-tm0yj2sn 280 5 inexpensive inexpensive JJ cord-276598-tm0yj2sn 280 6 oxidants oxidant NNS cord-276598-tm0yj2sn 280 7 without without IN cord-276598-tm0yj2sn 280 8 additives additive NNS cord-276598-tm0yj2sn 280 9 and and CC cord-276598-tm0yj2sn 280 10 generates generate VBZ cord-276598-tm0yj2sn 280 11 water water NN cord-276598-tm0yj2sn 280 12 or or CC cord-276598-tm0yj2sn 280 13 alkanol alkanol NN cord-276598-tm0yj2sn 280 14 as as IN cord-276598-tm0yj2sn 280 15 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 280 16 waste waste NN cord-276598-tm0yj2sn 280 17 . . . cord-276598-tm0yj2sn 281 1 However however RB cord-276598-tm0yj2sn 281 2 , , , cord-276598-tm0yj2sn 281 3 the the DT cord-276598-tm0yj2sn 281 4 synthetic synthetic JJ cord-276598-tm0yj2sn 281 5 routes route NNS cord-276598-tm0yj2sn 281 6 are be VBP cord-276598-tm0yj2sn 281 7 prone prone JJ cord-276598-tm0yj2sn 281 8 to to IN cord-276598-tm0yj2sn 281 9 the the DT cord-276598-tm0yj2sn 281 10 formation formation NN cord-276598-tm0yj2sn 281 11 of of IN cord-276598-tm0yj2sn 281 12 many many JJ cord-276598-tm0yj2sn 281 13 undesired undesired JJ cord-276598-tm0yj2sn 281 14 side side NN cord-276598-tm0yj2sn 281 15 products product NNS cord-276598-tm0yj2sn 281 16 , , , cord-276598-tm0yj2sn 281 17 suffer suffer VBP cord-276598-tm0yj2sn 281 18 from from IN cord-276598-tm0yj2sn 281 19 low low JJ cord-276598-tm0yj2sn 281 20 yields yield NNS cord-276598-tm0yj2sn 281 21 , , , cord-276598-tm0yj2sn 281 22 and and CC cord-276598-tm0yj2sn 281 23 sometimes sometimes RB cord-276598-tm0yj2sn 281 24 have have VBP cord-276598-tm0yj2sn 281 25 limited limit VBN cord-276598-tm0yj2sn 281 26 applicability applicability NN cord-276598-tm0yj2sn 281 27 . . . cord-276598-tm0yj2sn 282 1 Iodine iodine NN cord-276598-tm0yj2sn 282 2 ( ( -LRB- cord-276598-tm0yj2sn 282 3 I i NN cord-276598-tm0yj2sn 282 4 2 2 CD cord-276598-tm0yj2sn 282 5 ) ) -RRB- cord-276598-tm0yj2sn 282 6 has have VBZ cord-276598-tm0yj2sn 282 7 also also RB cord-276598-tm0yj2sn 282 8 been be VBN cord-276598-tm0yj2sn 282 9 used use VBN cord-276598-tm0yj2sn 282 10 as as IN cord-276598-tm0yj2sn 282 11 a a DT cord-276598-tm0yj2sn 282 12 catalyst catalyst NN cord-276598-tm0yj2sn 282 13 under under IN cord-276598-tm0yj2sn 282 14 solvent solvent NN cord-276598-tm0yj2sn 282 15 - - HYPH cord-276598-tm0yj2sn 282 16 free free JJ cord-276598-tm0yj2sn 282 17 conditions condition NNS cord-276598-tm0yj2sn 282 18 to to IN cord-276598-tm0yj2sn 282 19 couple couple NN cord-276598-tm0yj2sn 282 20 aryl aryl NN cord-276598-tm0yj2sn 282 21 amines amine NNS cord-276598-tm0yj2sn 282 22 ( ( -LRB- cord-276598-tm0yj2sn 282 23 PhNH PhNH NNP cord-276598-tm0yj2sn 282 24 2 2 CD cord-276598-tm0yj2sn 282 25 and and CC cord-276598-tm0yj2sn 282 26 derivatives derivative NNS cord-276598-tm0yj2sn 282 27 containing contain VBG cord-276598-tm0yj2sn 282 28 OH oh UH cord-276598-tm0yj2sn 282 29 , , , cord-276598-tm0yj2sn 282 30 OEt OEt NNS cord-276598-tm0yj2sn 282 31 , , , cord-276598-tm0yj2sn 282 32 CN CN NNP cord-276598-tm0yj2sn 282 33 , , , cord-276598-tm0yj2sn 282 34 OMe OMe NNS cord-276598-tm0yj2sn 282 35 , , , cord-276598-tm0yj2sn 282 36 NO no DT cord-276598-tm0yj2sn 282 37 2 2 CD cord-276598-tm0yj2sn 282 38 , , , cord-276598-tm0yj2sn 282 39 F F NNP cord-276598-tm0yj2sn 282 40 , , , cord-276598-tm0yj2sn 282 41 Cl Cl NNP cord-276598-tm0yj2sn 282 42 , , , cord-276598-tm0yj2sn 282 43 or or CC cord-276598-tm0yj2sn 282 44 Br Br NNP cord-276598-tm0yj2sn 282 45 substituents substituent NNS cord-276598-tm0yj2sn 282 46 on on IN cord-276598-tm0yj2sn 282 47 Ph Ph NNP cord-276598-tm0yj2sn 282 48 ) ) -RRB- cord-276598-tm0yj2sn 282 49 with with IN cord-276598-tm0yj2sn 282 50 ( ( -LRB- cord-276598-tm0yj2sn 282 51 RO ro NN cord-276598-tm0yj2sn 282 52 ) ) -RRB- cord-276598-tm0yj2sn 282 53 2 2 CD cord-276598-tm0yj2sn 283 1 P(O)H p(o)h NN cord-276598-tm0yj2sn 284 1 ( ( -LRB- cord-276598-tm0yj2sn 284 2 dialkyl dialkyl NNP cord-276598-tm0yj2sn 284 3 H H NNP cord-276598-tm0yj2sn 284 4 - - HYPH cord-276598-tm0yj2sn 284 5 P p NN cord-276598-tm0yj2sn 284 6 ; ; : cord-276598-tm0yj2sn 285 1 R r NN cord-276598-tm0yj2sn 285 2 = = NFP cord-276598-tm0yj2sn 286 1 Me -PRON- PRP cord-276598-tm0yj2sn 286 2 , , , cord-276598-tm0yj2sn 286 3 Et Et NNP cord-276598-tm0yj2sn 286 4 ) ) -RRB- cord-276598-tm0yj2sn 286 5 affording afford VBG cord-276598-tm0yj2sn 286 6 dialkyl dialkyl NN cord-276598-tm0yj2sn 286 7 P P NNP cord-276598-tm0yj2sn 286 8 - - HYPH cord-276598-tm0yj2sn 286 9 Ns Ns NNP cord-276598-tm0yj2sn 286 10 ( ( -LRB- cord-276598-tm0yj2sn 286 11 Scheme scheme NN cord-276598-tm0yj2sn 286 12 7b 7b CD cord-276598-tm0yj2sn 286 13 ) ) -RRB- cord-276598-tm0yj2sn 286 14 [ [ -LRB- cord-276598-tm0yj2sn 286 15 101 101 CD cord-276598-tm0yj2sn 286 16 ] ] -RRB- cord-276598-tm0yj2sn 286 17 . . . cord-276598-tm0yj2sn 287 1 Then then RB cord-276598-tm0yj2sn 287 2 , , , cord-276598-tm0yj2sn 287 3 the the DT cord-276598-tm0yj2sn 287 4 crude crude JJ cord-276598-tm0yj2sn 287 5 products product NNS cord-276598-tm0yj2sn 287 6 were be VBD cord-276598-tm0yj2sn 287 7 purified purify VBN cord-276598-tm0yj2sn 287 8 by by IN cord-276598-tm0yj2sn 287 9 column column NN cord-276598-tm0yj2sn 287 10 chromatography chromatography NN cord-276598-tm0yj2sn 287 11 ( ( -LRB- cord-276598-tm0yj2sn 287 12 on on IN cord-276598-tm0yj2sn 287 13 silica silica NN cord-276598-tm0yj2sn 287 14 ) ) -RRB- cord-276598-tm0yj2sn 287 15 to to TO cord-276598-tm0yj2sn 287 16 obtain obtain VB cord-276598-tm0yj2sn 287 17 yields yield NNS cord-276598-tm0yj2sn 287 18 of of IN cord-276598-tm0yj2sn 287 19 product product NN cord-276598-tm0yj2sn 287 20 in in IN cord-276598-tm0yj2sn 287 21 0 0 CD cord-276598-tm0yj2sn 287 22 - - SYM cord-276598-tm0yj2sn 287 23 88 88 CD cord-276598-tm0yj2sn 287 24 % % NN cord-276598-tm0yj2sn 287 25 . . . cord-276598-tm0yj2sn 288 1 The the DT cord-276598-tm0yj2sn 288 2 best good JJS cord-276598-tm0yj2sn 288 3 yielding yielding JJ cord-276598-tm0yj2sn 288 4 conditions condition NNS cord-276598-tm0yj2sn 288 5 were be VBD cord-276598-tm0yj2sn 288 6 shorter short JJR cord-276598-tm0yj2sn 288 7 reaction reaction NN cord-276598-tm0yj2sn 288 8 times time NNS cord-276598-tm0yj2sn 288 9 without without IN cord-276598-tm0yj2sn 288 10 solvent solvent NN cord-276598-tm0yj2sn 288 11 . . . cord-276598-tm0yj2sn 289 1 Reactions reaction NNS cord-276598-tm0yj2sn 289 2 performed perform VBN cord-276598-tm0yj2sn 289 3 in in IN cord-276598-tm0yj2sn 289 4 polar polar JJ cord-276598-tm0yj2sn 289 5 non non JJ cord-276598-tm0yj2sn 289 6 - - JJ cord-276598-tm0yj2sn 289 7 protic protic JJ cord-276598-tm0yj2sn 289 8 solvents solvent NNS cord-276598-tm0yj2sn 289 9 ( ( -LRB- cord-276598-tm0yj2sn 289 10 e.g. e.g. RB cord-276598-tm0yj2sn 289 11 , , , cord-276598-tm0yj2sn 289 12 CH CH NNP cord-276598-tm0yj2sn 289 13 2 2 CD cord-276598-tm0yj2sn 289 14 Cl Cl NNP cord-276598-tm0yj2sn 289 15 2 2 CD cord-276598-tm0yj2sn 289 16 ) ) -RRB- cord-276598-tm0yj2sn 289 17 , , , cord-276598-tm0yj2sn 289 18 non non JJ cord-276598-tm0yj2sn 289 19 - - JJ cord-276598-tm0yj2sn 289 20 polar polar JJ cord-276598-tm0yj2sn 289 21 solvents solvent NNS cord-276598-tm0yj2sn 289 22 ( ( -LRB- cord-276598-tm0yj2sn 289 23 e.g. e.g. RB cord-276598-tm0yj2sn 289 24 , , , cord-276598-tm0yj2sn 289 25 hexane hexane NNP cord-276598-tm0yj2sn 289 26 ) ) -RRB- cord-276598-tm0yj2sn 289 27 , , , cord-276598-tm0yj2sn 289 28 or or CC cord-276598-tm0yj2sn 289 29 protic protic JJ cord-276598-tm0yj2sn 289 30 solvents solvent NNS cord-276598-tm0yj2sn 289 31 ( ( -LRB- cord-276598-tm0yj2sn 289 32 e.g. e.g. RB cord-276598-tm0yj2sn 289 33 , , , cord-276598-tm0yj2sn 289 34 MeOH MeOH NNP cord-276598-tm0yj2sn 289 35 ) ) -RRB- cord-276598-tm0yj2sn 289 36 all all DT cord-276598-tm0yj2sn 289 37 suffered suffer VBD cord-276598-tm0yj2sn 289 38 from from IN cord-276598-tm0yj2sn 289 39 reduced reduced JJ cord-276598-tm0yj2sn 289 40 efficiency efficiency NN cord-276598-tm0yj2sn 289 41 and and CC cord-276598-tm0yj2sn 289 42 selectivity selectivity NN cord-276598-tm0yj2sn 289 43 . . . cord-276598-tm0yj2sn 290 1 Furthermore furthermore RB cord-276598-tm0yj2sn 290 2 , , , cord-276598-tm0yj2sn 290 3 aniline aniline NN cord-276598-tm0yj2sn 290 4 with with IN cord-276598-tm0yj2sn 290 5 substituents substituent NNS cord-276598-tm0yj2sn 290 6 at at IN cord-276598-tm0yj2sn 290 7 orthoand orthoand NNP cord-276598-tm0yj2sn 290 8 meta meta NNP cord-276598-tm0yj2sn 290 9 - - HYPH cord-276598-tm0yj2sn 290 10 positions position NNS cord-276598-tm0yj2sn 290 11 were be VBD cord-276598-tm0yj2sn 290 12 observed observe VBN cord-276598-tm0yj2sn 290 13 to to TO cord-276598-tm0yj2sn 290 14 have have VB cord-276598-tm0yj2sn 290 15 reacted react VBN cord-276598-tm0yj2sn 290 16 faster fast RBR cord-276598-tm0yj2sn 290 17 and and CC cord-276598-tm0yj2sn 290 18 were be VBD cord-276598-tm0yj2sn 290 19 higher high JJR cord-276598-tm0yj2sn 290 20 yielding yield VBG cord-276598-tm0yj2sn 290 21 than than IN cord-276598-tm0yj2sn 290 22 aniline aniline NN cord-276598-tm0yj2sn 290 23 containing contain VBG cord-276598-tm0yj2sn 290 24 substituents substituent NNS cord-276598-tm0yj2sn 290 25 at at IN cord-276598-tm0yj2sn 290 26 the the DT cord-276598-tm0yj2sn 290 27 para para NNP cord-276598-tm0yj2sn 290 28 - - HYPH cord-276598-tm0yj2sn 290 29 position position NN cord-276598-tm0yj2sn 290 30 . . . cord-276598-tm0yj2sn 291 1 Iodine iodine NN cord-276598-tm0yj2sn 291 2 ( ( -LRB- cord-276598-tm0yj2sn 291 3 I2 I2 NNP cord-276598-tm0yj2sn 291 4 ) ) -RRB- cord-276598-tm0yj2sn 291 5 has have VBZ cord-276598-tm0yj2sn 291 6 also also RB cord-276598-tm0yj2sn 291 7 been be VBN cord-276598-tm0yj2sn 291 8 used use VBN cord-276598-tm0yj2sn 291 9 as as IN cord-276598-tm0yj2sn 291 10 a a DT cord-276598-tm0yj2sn 291 11 catalyst catalyst NN cord-276598-tm0yj2sn 291 12 under under IN cord-276598-tm0yj2sn 291 13 solvent solvent NN cord-276598-tm0yj2sn 291 14 - - HYPH cord-276598-tm0yj2sn 291 15 free free JJ cord-276598-tm0yj2sn 291 16 conditions condition NNS cord-276598-tm0yj2sn 291 17 to to IN cord-276598-tm0yj2sn 291 18 couple couple NN cord-276598-tm0yj2sn 291 19 aryl aryl NN cord-276598-tm0yj2sn 291 20 amines amine NNS cord-276598-tm0yj2sn 291 21 ( ( -LRB- cord-276598-tm0yj2sn 291 22 PhNH2 phnh2 NN cord-276598-tm0yj2sn 291 23 and and CC cord-276598-tm0yj2sn 291 24 derivatives derivative NNS cord-276598-tm0yj2sn 291 25 containing contain VBG cord-276598-tm0yj2sn 291 26 OH oh UH cord-276598-tm0yj2sn 291 27 , , , cord-276598-tm0yj2sn 291 28 OEt OEt NNS cord-276598-tm0yj2sn 291 29 , , , cord-276598-tm0yj2sn 291 30 CN CN NNP cord-276598-tm0yj2sn 291 31 , , , cord-276598-tm0yj2sn 291 32 OMe OMe NNS cord-276598-tm0yj2sn 291 33 , , , cord-276598-tm0yj2sn 291 34 NO2 NO2 NNP cord-276598-tm0yj2sn 291 35 , , , cord-276598-tm0yj2sn 291 36 F F NNP cord-276598-tm0yj2sn 291 37 , , , cord-276598-tm0yj2sn 291 38 Cl Cl NNP cord-276598-tm0yj2sn 291 39 , , , cord-276598-tm0yj2sn 291 40 or or CC cord-276598-tm0yj2sn 291 41 Br Br NNP cord-276598-tm0yj2sn 291 42 substituents substituent NNS cord-276598-tm0yj2sn 291 43 on on IN cord-276598-tm0yj2sn 291 44 Ph Ph NNP cord-276598-tm0yj2sn 291 45 ) ) -RRB- cord-276598-tm0yj2sn 291 46 with with IN cord-276598-tm0yj2sn 291 47 ( ( -LRB- cord-276598-tm0yj2sn 291 48 RO)2P(O)H RO)2P(O)H NNP cord-276598-tm0yj2sn 291 49 ( ( -LRB- cord-276598-tm0yj2sn 291 50 dialkyl dialkyl NNP cord-276598-tm0yj2sn 291 51 H H NNP cord-276598-tm0yj2sn 291 52 - - HYPH cord-276598-tm0yj2sn 291 53 P p NN cord-276598-tm0yj2sn 291 54 ; ; : cord-276598-tm0yj2sn 291 55 R r NN cord-276598-tm0yj2sn 291 56 = = NN cord-276598-tm0yj2sn 292 1 Me -PRON- PRP cord-276598-tm0yj2sn 292 2 , , , cord-276598-tm0yj2sn 292 3 Et Et NNP cord-276598-tm0yj2sn 292 4 ) ) -RRB- cord-276598-tm0yj2sn 292 5 affording afford VBG cord-276598-tm0yj2sn 292 6 dialkyl dialkyl NN cord-276598-tm0yj2sn 292 7 P P NNP cord-276598-tm0yj2sn 292 8 - - HYPH cord-276598-tm0yj2sn 292 9 Ns Ns NNP cord-276598-tm0yj2sn 292 10 ( ( -LRB- cord-276598-tm0yj2sn 292 11 Scheme scheme NN cord-276598-tm0yj2sn 292 12 7b 7b CD cord-276598-tm0yj2sn 292 13 ) ) -RRB- cord-276598-tm0yj2sn 292 14 [ [ -LRB- cord-276598-tm0yj2sn 292 15 101 101 CD cord-276598-tm0yj2sn 292 16 ] ] -RRB- cord-276598-tm0yj2sn 292 17 . . . cord-276598-tm0yj2sn 293 1 Then then RB cord-276598-tm0yj2sn 293 2 , , , cord-276598-tm0yj2sn 293 3 the the DT cord-276598-tm0yj2sn 293 4 crude crude JJ cord-276598-tm0yj2sn 293 5 products product NNS cord-276598-tm0yj2sn 293 6 were be VBD cord-276598-tm0yj2sn 293 7 purified purify VBN cord-276598-tm0yj2sn 293 8 by by IN cord-276598-tm0yj2sn 293 9 column column NN cord-276598-tm0yj2sn 293 10 chromatography chromatography NN cord-276598-tm0yj2sn 293 11 ( ( -LRB- cord-276598-tm0yj2sn 293 12 on on IN cord-276598-tm0yj2sn 293 13 silica silica NN cord-276598-tm0yj2sn 293 14 ) ) -RRB- cord-276598-tm0yj2sn 293 15 to to TO cord-276598-tm0yj2sn 293 16 obtain obtain VB cord-276598-tm0yj2sn 293 17 yields yield NNS cord-276598-tm0yj2sn 293 18 of of IN cord-276598-tm0yj2sn 293 19 product product NN cord-276598-tm0yj2sn 293 20 in in IN cord-276598-tm0yj2sn 293 21 0 0 CD cord-276598-tm0yj2sn 293 22 - - SYM cord-276598-tm0yj2sn 293 23 88 88 CD cord-276598-tm0yj2sn 293 24 % % NN cord-276598-tm0yj2sn 293 25 . . . cord-276598-tm0yj2sn 294 1 The the DT cord-276598-tm0yj2sn 294 2 best good JJS cord-276598-tm0yj2sn 294 3 yielding yielding JJ cord-276598-tm0yj2sn 294 4 conditions condition NNS cord-276598-tm0yj2sn 294 5 were be VBD cord-276598-tm0yj2sn 294 6 shorter short JJR cord-276598-tm0yj2sn 294 7 reaction reaction NN cord-276598-tm0yj2sn 294 8 times time NNS cord-276598-tm0yj2sn 294 9 without without IN cord-276598-tm0yj2sn 294 10 solvent solvent NN cord-276598-tm0yj2sn 294 11 . . . cord-276598-tm0yj2sn 295 1 Reactions reaction NNS cord-276598-tm0yj2sn 295 2 performed perform VBN cord-276598-tm0yj2sn 295 3 in in IN cord-276598-tm0yj2sn 295 4 polar polar JJ cord-276598-tm0yj2sn 295 5 non non JJ cord-276598-tm0yj2sn 295 6 - - JJ cord-276598-tm0yj2sn 295 7 protic protic JJ cord-276598-tm0yj2sn 295 8 solvents solvent NNS cord-276598-tm0yj2sn 295 9 ( ( -LRB- cord-276598-tm0yj2sn 295 10 e.g. e.g. RB cord-276598-tm0yj2sn 295 11 , , , cord-276598-tm0yj2sn 295 12 CH2Cl2 ch2cl2 NN cord-276598-tm0yj2sn 295 13 ) ) -RRB- cord-276598-tm0yj2sn 295 14 , , , cord-276598-tm0yj2sn 295 15 non non JJ cord-276598-tm0yj2sn 295 16 - - JJ cord-276598-tm0yj2sn 295 17 polar polar JJ cord-276598-tm0yj2sn 295 18 solvents solvent NNS cord-276598-tm0yj2sn 295 19 ( ( -LRB- cord-276598-tm0yj2sn 295 20 e.g. e.g. RB cord-276598-tm0yj2sn 295 21 , , , cord-276598-tm0yj2sn 295 22 hexane hexane NNP cord-276598-tm0yj2sn 295 23 ) ) -RRB- cord-276598-tm0yj2sn 295 24 , , , cord-276598-tm0yj2sn 295 25 or or CC cord-276598-tm0yj2sn 295 26 protic protic JJ cord-276598-tm0yj2sn 295 27 solvents solvent NNS cord-276598-tm0yj2sn 295 28 ( ( -LRB- cord-276598-tm0yj2sn 295 29 e.g. e.g. RB cord-276598-tm0yj2sn 295 30 , , , cord-276598-tm0yj2sn 295 31 MeOH MeOH NNP cord-276598-tm0yj2sn 295 32 ) ) -RRB- cord-276598-tm0yj2sn 295 33 all all DT cord-276598-tm0yj2sn 295 34 suffered suffer VBD cord-276598-tm0yj2sn 295 35 from from IN cord-276598-tm0yj2sn 295 36 reduced reduced JJ cord-276598-tm0yj2sn 295 37 efficiency efficiency NN cord-276598-tm0yj2sn 295 38 and and CC cord-276598-tm0yj2sn 295 39 selectivity selectivity NN cord-276598-tm0yj2sn 295 40 . . . cord-276598-tm0yj2sn 296 1 Furthermore furthermore RB cord-276598-tm0yj2sn 296 2 , , , cord-276598-tm0yj2sn 296 3 aniline aniline NN cord-276598-tm0yj2sn 296 4 with with IN cord-276598-tm0yj2sn 296 5 substituents substituent NNS cord-276598-tm0yj2sn 296 6 at at IN cord-276598-tm0yj2sn 296 7 ortho ortho NNP cord-276598-tm0yj2sn 296 8 - - HYPH cord-276598-tm0yj2sn 296 9 and and CC cord-276598-tm0yj2sn 296 10 meta meta NNP cord-276598-tm0yj2sn 296 11 - - HYPH cord-276598-tm0yj2sn 296 12 positions position NNS cord-276598-tm0yj2sn 296 13 were be VBD cord-276598-tm0yj2sn 296 14 observed observe VBN cord-276598-tm0yj2sn 296 15 to to TO cord-276598-tm0yj2sn 296 16 have have VB cord-276598-tm0yj2sn 296 17 reacted react VBN cord-276598-tm0yj2sn 296 18 faster fast RBR cord-276598-tm0yj2sn 296 19 and and CC cord-276598-tm0yj2sn 296 20 were be VBD cord-276598-tm0yj2sn 296 21 higher high JJR cord-276598-tm0yj2sn 296 22 yielding yield VBG cord-276598-tm0yj2sn 296 23 than than IN cord-276598-tm0yj2sn 296 24 aniline aniline NN cord-276598-tm0yj2sn 296 25 containing contain VBG cord-276598-tm0yj2sn 296 26 substituents substituent NNS cord-276598-tm0yj2sn 296 27 at at IN cord-276598-tm0yj2sn 296 28 the the DT cord-276598-tm0yj2sn 296 29 para para NNP cord-276598-tm0yj2sn 296 30 - - HYPH cord-276598-tm0yj2sn 296 31 position position NN cord-276598-tm0yj2sn 296 32 . . . cord-276598-tm0yj2sn 297 1 I2 I2 NNP cord-276598-tm0yj2sn 297 2 was be VBD cord-276598-tm0yj2sn 297 3 used use VBN cord-276598-tm0yj2sn 297 4 in in IN cord-276598-tm0yj2sn 297 5 the the DT cord-276598-tm0yj2sn 297 6 presence presence NN cord-276598-tm0yj2sn 297 7 of of IN cord-276598-tm0yj2sn 297 8 H2O2 H2O2 NNP cord-276598-tm0yj2sn 297 9 as as IN cord-276598-tm0yj2sn 297 10 a a DT cord-276598-tm0yj2sn 297 11 catalyst catalyst NN cord-276598-tm0yj2sn 297 12 at at IN cord-276598-tm0yj2sn 297 13 20 20 CD cord-276598-tm0yj2sn 297 14 ° ° NN cord-276598-tm0yj2sn 297 15 C c NN cord-276598-tm0yj2sn 297 16 for for IN cord-276598-tm0yj2sn 297 17 the the DT cord-276598-tm0yj2sn 297 18 dehydrogenative dehydrogenative JJ cord-276598-tm0yj2sn 297 19 cross cross NN cord-276598-tm0yj2sn 297 20 - - NN cord-276598-tm0yj2sn 297 21 coupling coupling NN cord-276598-tm0yj2sn 297 22 of of IN cord-276598-tm0yj2sn 297 23 diethyl diethyl NNP cord-276598-tm0yj2sn 297 24 H H NNP cord-276598-tm0yj2sn 297 25 - - HYPH cord-276598-tm0yj2sn 297 26 P p NN cord-276598-tm0yj2sn 297 27 and and CC cord-276598-tm0yj2sn 297 28 amine amine NN cord-276598-tm0yj2sn 297 29 or or CC cord-276598-tm0yj2sn 297 30 sulfoximines sulfoximine NNS cord-276598-tm0yj2sn 297 31 to to TO cord-276598-tm0yj2sn 297 32 form form VB cord-276598-tm0yj2sn 297 33 P p NN cord-276598-tm0yj2sn 297 34 - - HYPH cord-276598-tm0yj2sn 297 35 Ns Ns NNP cord-276598-tm0yj2sn 297 36 ( ( -LRB- cord-276598-tm0yj2sn 297 37 Scheme scheme NN cord-276598-tm0yj2sn 297 38 7c 7c CD cord-276598-tm0yj2sn 297 39 ) ) -RRB- cord-276598-tm0yj2sn 297 40 [ [ -LRB- cord-276598-tm0yj2sn 297 41 102 102 CD cord-276598-tm0yj2sn 297 42 ] ] -RRB- cord-276598-tm0yj2sn 297 43 . . . cord-276598-tm0yj2sn 298 1 Purification purification NN cord-276598-tm0yj2sn 298 2 of of IN cord-276598-tm0yj2sn 298 3 the the DT cord-276598-tm0yj2sn 298 4 products product NNS cord-276598-tm0yj2sn 298 5 by by IN cord-276598-tm0yj2sn 298 6 column column NN cord-276598-tm0yj2sn 298 7 chromatography chromatography NN cord-276598-tm0yj2sn 298 8 ( ( -LRB- cord-276598-tm0yj2sn 298 9 on on IN cord-276598-tm0yj2sn 298 10 silica silica NN cord-276598-tm0yj2sn 298 11 ) ) -RRB- cord-276598-tm0yj2sn 298 12 afforded afford VBN cord-276598-tm0yj2sn 298 13 P p NN cord-276598-tm0yj2sn 298 14 - - HYPH cord-276598-tm0yj2sn 298 15 Ns Ns NNP cord-276598-tm0yj2sn 298 16 with with IN cord-276598-tm0yj2sn 298 17 isolated isolated JJ cord-276598-tm0yj2sn 298 18 yields yield NNS cord-276598-tm0yj2sn 298 19 of of IN cord-276598-tm0yj2sn 298 20 31 31 CD cord-276598-tm0yj2sn 298 21 - - SYM cord-276598-tm0yj2sn 298 22 96 96 CD cord-276598-tm0yj2sn 298 23 % % NN cord-276598-tm0yj2sn 298 24 , , , cord-276598-tm0yj2sn 298 25 with with IN cord-276598-tm0yj2sn 298 26 the the DT cord-276598-tm0yj2sn 298 27 lower lower RBR cord-276598-tm0yj2sn 298 28 yielding yield VBG cord-276598-tm0yj2sn 298 29 products product NNS cord-276598-tm0yj2sn 298 30 reported report VBN cord-276598-tm0yj2sn 298 31 from from IN cord-276598-tm0yj2sn 298 32 sulfoximine sulfoximine NNP cord-276598-tm0yj2sn 298 33 . . . cord-276598-tm0yj2sn 299 1 Both both DT cord-276598-tm0yj2sn 299 2 alkyl alkyl NN cord-276598-tm0yj2sn 299 3 and and CC cord-276598-tm0yj2sn 299 4 aryl aryl NN cord-276598-tm0yj2sn 299 5 H H NNP cord-276598-tm0yj2sn 299 6 - - HYPH cord-276598-tm0yj2sn 299 7 P p NN cord-276598-tm0yj2sn 299 8 ( ( -LRB- cord-276598-tm0yj2sn 299 9 ( ( -LRB- cord-276598-tm0yj2sn 299 10 RO)2P(O)H RO)2P(O)H NNP cord-276598-tm0yj2sn 299 11 , , , cord-276598-tm0yj2sn 299 12 R r NN cord-276598-tm0yj2sn 299 13 = = FW cord-276598-tm0yj2sn 299 14 Et et NN cord-276598-tm0yj2sn 299 15 , , , cord-276598-tm0yj2sn 299 16 i i NN cord-276598-tm0yj2sn 299 17 - - HYPH cord-276598-tm0yj2sn 299 18 Pr Pr NNP cord-276598-tm0yj2sn 299 19 , , , cord-276598-tm0yj2sn 299 20 Ph Ph NNP cord-276598-tm0yj2sn 299 21 ) ) -RRB- cord-276598-tm0yj2sn 299 22 were be VBD cord-276598-tm0yj2sn 299 23 used use VBN cord-276598-tm0yj2sn 299 24 as as IN cord-276598-tm0yj2sn 299 25 the the DT cord-276598-tm0yj2sn 299 26 substrate substrate NN cord-276598-tm0yj2sn 299 27 along along IN cord-276598-tm0yj2sn 299 28 with with IN cord-276598-tm0yj2sn 299 29 cyclic cyclic JJ cord-276598-tm0yj2sn 299 30 aromatic aromatic JJ cord-276598-tm0yj2sn 299 31 secondary secondary JJ cord-276598-tm0yj2sn 299 32 amines amine NNS cord-276598-tm0yj2sn 299 33 ( ( -LRB- cord-276598-tm0yj2sn 299 34 e.g. e.g. RB cord-276598-tm0yj2sn 299 35 , , , cord-276598-tm0yj2sn 299 36 indole indole NN cord-276598-tm0yj2sn 299 37 ) ) -RRB- cord-276598-tm0yj2sn 299 38 , , , cord-276598-tm0yj2sn 299 39 derivatives derivative NNS cord-276598-tm0yj2sn 299 40 of of IN cord-276598-tm0yj2sn 299 41 heterocyclic heterocyclic JJ cord-276598-tm0yj2sn 299 42 amines amine NNS cord-276598-tm0yj2sn 299 43 ( ( -LRB- cord-276598-tm0yj2sn 299 44 e.g. e.g. RB cord-276598-tm0yj2sn 299 45 , , , cord-276598-tm0yj2sn 299 46 furfurylamine furfurylamine NN cord-276598-tm0yj2sn 299 47 ) ) -RRB- cord-276598-tm0yj2sn 299 48 , , , cord-276598-tm0yj2sn 299 49 aliphatic aliphatic JJ cord-276598-tm0yj2sn 299 50 cyclic cyclic JJ cord-276598-tm0yj2sn 299 51 secondary secondary JJ cord-276598-tm0yj2sn 299 52 amines amine NNS cord-276598-tm0yj2sn 299 53 ( ( -LRB- cord-276598-tm0yj2sn 299 54 e.g. e.g. RB cord-276598-tm0yj2sn 299 55 , , , cord-276598-tm0yj2sn 299 56 1-benzhydrylpiperazine 1-benzhydrylpiperazine CD cord-276598-tm0yj2sn 299 57 ) ) -RRB- cord-276598-tm0yj2sn 300 1 , , , cord-276598-tm0yj2sn 300 2 tertiary tertiary JJ cord-276598-tm0yj2sn 300 3 amines amine NNS cord-276598-tm0yj2sn 300 4 ( ( -LRB- cord-276598-tm0yj2sn 300 5 e.g. e.g. RB cord-276598-tm0yj2sn 300 6 , , , cord-276598-tm0yj2sn 300 7 N N NNP cord-276598-tm0yj2sn 300 8 - - HYPH cord-276598-tm0yj2sn 300 9 methylhomopiperazine methylhomopiperazine NNP cord-276598-tm0yj2sn 300 10 ) ) -RRB- cord-276598-tm0yj2sn 300 11 , , , cord-276598-tm0yj2sn 300 12 or or CC cord-276598-tm0yj2sn 300 13 sulfoximine sulfoximine NNP cord-276598-tm0yj2sn 300 14 . . . cord-276598-tm0yj2sn 301 1 According accord VBG cord-276598-tm0yj2sn 301 2 to to IN cord-276598-tm0yj2sn 301 3 the the DT cord-276598-tm0yj2sn 301 4 article article NN cord-276598-tm0yj2sn 301 5 , , , cord-276598-tm0yj2sn 301 6 using use VBG cord-276598-tm0yj2sn 301 7 other other JJ cord-276598-tm0yj2sn 301 8 sources source NNS cord-276598-tm0yj2sn 301 9 of of IN cord-276598-tm0yj2sn 301 10 I2 I2 NNP cord-276598-tm0yj2sn 301 11 such such JJ cord-276598-tm0yj2sn 301 12 as as IN cord-276598-tm0yj2sn 301 13 KI KI NNP cord-276598-tm0yj2sn 301 14 or or CC cord-276598-tm0yj2sn 301 15 N N NNP cord-276598-tm0yj2sn 301 16 - - HYPH cord-276598-tm0yj2sn 301 17 bromosuccinimide bromosuccinimide NN cord-276598-tm0yj2sn 301 18 ( ( -LRB- cord-276598-tm0yj2sn 301 19 NBS NBS NNP cord-276598-tm0yj2sn 301 20 ) ) -RRB- cord-276598-tm0yj2sn 301 21 for for IN cord-276598-tm0yj2sn 301 22 the the DT cord-276598-tm0yj2sn 301 23 reaction reaction NN cord-276598-tm0yj2sn 301 24 resulted result VBD cord-276598-tm0yj2sn 301 25 in in IN cord-276598-tm0yj2sn 301 26 decreased decreased JJ cord-276598-tm0yj2sn 301 27 yield yield NN cord-276598-tm0yj2sn 301 28 and and CC cord-276598-tm0yj2sn 301 29 trace trace NN cord-276598-tm0yj2sn 301 30 quantities quantity NNS cord-276598-tm0yj2sn 301 31 of of IN cord-276598-tm0yj2sn 301 32 the the DT cord-276598-tm0yj2sn 301 33 desired desire VBN cord-276598-tm0yj2sn 301 34 products product NNS cord-276598-tm0yj2sn 301 35 , , , cord-276598-tm0yj2sn 301 36 respectively respectively RB cord-276598-tm0yj2sn 301 37 . . . cord-276598-tm0yj2sn 302 1 Iodine iodine NN cord-276598-tm0yj2sn 302 2 - - HYPH cord-276598-tm0yj2sn 302 3 mediated mediate VBN cord-276598-tm0yj2sn 302 4 oxidative oxidative JJ cord-276598-tm0yj2sn 302 5 cross cross JJ cord-276598-tm0yj2sn 302 6 - - JJ cord-276598-tm0yj2sn 302 7 coupling coupling JJ cord-276598-tm0yj2sn 302 8 methods method NNS cord-276598-tm0yj2sn 302 9 offer offer VBP cord-276598-tm0yj2sn 302 10 better well JJR cord-276598-tm0yj2sn 302 11 routes route NNS cord-276598-tm0yj2sn 302 12 to to IN cord-276598-tm0yj2sn 302 13 P P NNP cord-276598-tm0yj2sn 302 14 - - HYPH cord-276598-tm0yj2sn 302 15 N n CD cord-276598-tm0yj2sn 302 16 compounds compound NNS cord-276598-tm0yj2sn 302 17 by by IN cord-276598-tm0yj2sn 302 18 eliminating eliminate VBG cord-276598-tm0yj2sn 302 19 toxic toxic JJ cord-276598-tm0yj2sn 302 20 halogenating halogenating NN cord-276598-tm0yj2sn 302 21 agents agent NNS cord-276598-tm0yj2sn 302 22 such such JJ cord-276598-tm0yj2sn 302 23 as as IN cord-276598-tm0yj2sn 302 24 CCl4 ccl4 NN cord-276598-tm0yj2sn 302 25 in in IN cord-276598-tm0yj2sn 302 26 the the DT cord-276598-tm0yj2sn 302 27 synthetic synthetic JJ cord-276598-tm0yj2sn 302 28 processes process NNS cord-276598-tm0yj2sn 302 29 . . . cord-276598-tm0yj2sn 303 1 The the DT cord-276598-tm0yj2sn 303 2 method method NN cord-276598-tm0yj2sn 303 3 also also RB cord-276598-tm0yj2sn 303 4 uses use VBZ cord-276598-tm0yj2sn 303 5 inexpensive inexpensive JJ cord-276598-tm0yj2sn 303 6 oxidants oxidant NNS cord-276598-tm0yj2sn 303 7 without without IN cord-276598-tm0yj2sn 303 8 additives additive NNS cord-276598-tm0yj2sn 303 9 and and CC cord-276598-tm0yj2sn 303 10 generates generate VBZ cord-276598-tm0yj2sn 303 11 water water NN cord-276598-tm0yj2sn 303 12 or or CC cord-276598-tm0yj2sn 303 13 alkanol alkanol NN cord-276598-tm0yj2sn 303 14 as as IN cord-276598-tm0yj2sn 303 15 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 303 16 waste waste NN cord-276598-tm0yj2sn 303 17 . . . cord-276598-tm0yj2sn 304 1 However however RB cord-276598-tm0yj2sn 304 2 , , , cord-276598-tm0yj2sn 304 3 the the DT cord-276598-tm0yj2sn 304 4 synthetic synthetic JJ cord-276598-tm0yj2sn 304 5 routes route NNS cord-276598-tm0yj2sn 304 6 are be VBP cord-276598-tm0yj2sn 304 7 prone prone JJ cord-276598-tm0yj2sn 304 8 to to IN cord-276598-tm0yj2sn 304 9 the the DT cord-276598-tm0yj2sn 304 10 formation formation NN cord-276598-tm0yj2sn 304 11 of of IN cord-276598-tm0yj2sn 304 12 many many JJ cord-276598-tm0yj2sn 304 13 undesired undesired JJ cord-276598-tm0yj2sn 304 14 side side NN cord-276598-tm0yj2sn 304 15 products product NNS cord-276598-tm0yj2sn 304 16 , , , cord-276598-tm0yj2sn 304 17 suffer suffer VBP cord-276598-tm0yj2sn 304 18 from from IN cord-276598-tm0yj2sn 304 19 low low JJ cord-276598-tm0yj2sn 304 20 yields yield NNS cord-276598-tm0yj2sn 304 21 , , , cord-276598-tm0yj2sn 304 22 and and CC cord-276598-tm0yj2sn 304 23 sometimes sometimes RB cord-276598-tm0yj2sn 304 24 have have VBP cord-276598-tm0yj2sn 304 25 limited limit VBN cord-276598-tm0yj2sn 304 26 applicability applicability NN cord-276598-tm0yj2sn 304 27 . . . cord-276598-tm0yj2sn 305 1 I -PRON- PRP cord-276598-tm0yj2sn 305 2 2 2 CD cord-276598-tm0yj2sn 305 3 was be VBD cord-276598-tm0yj2sn 305 4 used use VBN cord-276598-tm0yj2sn 305 5 in in IN cord-276598-tm0yj2sn 305 6 the the DT cord-276598-tm0yj2sn 305 7 presence presence NN cord-276598-tm0yj2sn 305 8 of of IN cord-276598-tm0yj2sn 305 9 H h NN cord-276598-tm0yj2sn 305 10 2 2 CD cord-276598-tm0yj2sn 305 11 O o NN cord-276598-tm0yj2sn 305 12 2 2 CD cord-276598-tm0yj2sn 305 13 as as IN cord-276598-tm0yj2sn 305 14 a a DT cord-276598-tm0yj2sn 305 15 catalyst catalyst NN cord-276598-tm0yj2sn 305 16 at at IN cord-276598-tm0yj2sn 305 17 20 20 CD cord-276598-tm0yj2sn 305 18 • • NN cord-276598-tm0yj2sn 305 19 C c NN cord-276598-tm0yj2sn 305 20 for for IN cord-276598-tm0yj2sn 305 21 the the DT cord-276598-tm0yj2sn 305 22 dehydrogenative dehydrogenative JJ cord-276598-tm0yj2sn 305 23 cross cross NN cord-276598-tm0yj2sn 305 24 - - NN cord-276598-tm0yj2sn 305 25 coupling coupling NN cord-276598-tm0yj2sn 305 26 of of IN cord-276598-tm0yj2sn 305 27 diethyl diethyl NNP cord-276598-tm0yj2sn 305 28 H H NNP cord-276598-tm0yj2sn 305 29 - - HYPH cord-276598-tm0yj2sn 305 30 P p NN cord-276598-tm0yj2sn 305 31 and and CC cord-276598-tm0yj2sn 305 32 amine amine NN cord-276598-tm0yj2sn 305 33 or or CC cord-276598-tm0yj2sn 305 34 sulfoximines sulfoximine NNS cord-276598-tm0yj2sn 305 35 to to TO cord-276598-tm0yj2sn 305 36 form form VB cord-276598-tm0yj2sn 305 37 P p NN cord-276598-tm0yj2sn 305 38 - - HYPH cord-276598-tm0yj2sn 305 39 Ns Ns NNP cord-276598-tm0yj2sn 305 40 ( ( -LRB- cord-276598-tm0yj2sn 305 41 Scheme scheme NN cord-276598-tm0yj2sn 305 42 7c 7c CD cord-276598-tm0yj2sn 305 43 ) ) -RRB- cord-276598-tm0yj2sn 305 44 [ [ -LRB- cord-276598-tm0yj2sn 305 45 102 102 CD cord-276598-tm0yj2sn 305 46 ] ] -RRB- cord-276598-tm0yj2sn 305 47 . . . cord-276598-tm0yj2sn 306 1 Purification purification NN cord-276598-tm0yj2sn 306 2 of of IN cord-276598-tm0yj2sn 306 3 the the DT cord-276598-tm0yj2sn 306 4 products product NNS cord-276598-tm0yj2sn 306 5 by by IN cord-276598-tm0yj2sn 306 6 column column NN cord-276598-tm0yj2sn 306 7 chromatography chromatography NN cord-276598-tm0yj2sn 306 8 ( ( -LRB- cord-276598-tm0yj2sn 306 9 on on IN cord-276598-tm0yj2sn 306 10 silica silica NN cord-276598-tm0yj2sn 306 11 ) ) -RRB- cord-276598-tm0yj2sn 306 12 afforded afford VBN cord-276598-tm0yj2sn 306 13 P p NN cord-276598-tm0yj2sn 306 14 - - HYPH cord-276598-tm0yj2sn 306 15 Ns Ns NNP cord-276598-tm0yj2sn 306 16 with with IN cord-276598-tm0yj2sn 306 17 isolated isolated JJ cord-276598-tm0yj2sn 306 18 yields yield NNS cord-276598-tm0yj2sn 306 19 of of IN cord-276598-tm0yj2sn 306 20 31 31 CD cord-276598-tm0yj2sn 306 21 - - SYM cord-276598-tm0yj2sn 306 22 96 96 CD cord-276598-tm0yj2sn 306 23 % % NN cord-276598-tm0yj2sn 306 24 , , , cord-276598-tm0yj2sn 306 25 with with IN cord-276598-tm0yj2sn 306 26 the the DT cord-276598-tm0yj2sn 306 27 lower lower RBR cord-276598-tm0yj2sn 306 28 yielding yield VBG cord-276598-tm0yj2sn 306 29 products product NNS cord-276598-tm0yj2sn 306 30 reported report VBN cord-276598-tm0yj2sn 306 31 from from IN cord-276598-tm0yj2sn 306 32 sulfoximine sulfoximine NNP cord-276598-tm0yj2sn 306 33 . . . cord-276598-tm0yj2sn 307 1 Both both DT cord-276598-tm0yj2sn 307 2 alkyl alkyl NN cord-276598-tm0yj2sn 307 3 and and CC cord-276598-tm0yj2sn 307 4 aryl aryl NN cord-276598-tm0yj2sn 307 5 H H NNP cord-276598-tm0yj2sn 307 6 - - HYPH cord-276598-tm0yj2sn 307 7 P p NN cord-276598-tm0yj2sn 307 8 ( ( -LRB- cord-276598-tm0yj2sn 307 9 ( ( -LRB- cord-276598-tm0yj2sn 307 10 RO RO NNP cord-276598-tm0yj2sn 307 11 ) ) -RRB- cord-276598-tm0yj2sn 307 12 2 2 CD cord-276598-tm0yj2sn 308 1 P(O)H p(o)h NN cord-276598-tm0yj2sn 309 1 , , , cord-276598-tm0yj2sn 309 2 R r NN cord-276598-tm0yj2sn 309 3 = = SYM cord-276598-tm0yj2sn 309 4 Et Et NNP cord-276598-tm0yj2sn 309 5 , , , cord-276598-tm0yj2sn 309 6 i i NN cord-276598-tm0yj2sn 309 7 - - HYPH cord-276598-tm0yj2sn 309 8 Pr Pr NNP cord-276598-tm0yj2sn 309 9 , , , cord-276598-tm0yj2sn 309 10 Ph Ph NNP cord-276598-tm0yj2sn 309 11 ) ) -RRB- cord-276598-tm0yj2sn 309 12 were be VBD cord-276598-tm0yj2sn 309 13 used use VBN cord-276598-tm0yj2sn 309 14 as as IN cord-276598-tm0yj2sn 309 15 the the DT cord-276598-tm0yj2sn 309 16 substrate substrate NN cord-276598-tm0yj2sn 309 17 along along IN cord-276598-tm0yj2sn 309 18 with with IN cord-276598-tm0yj2sn 309 19 cyclic cyclic JJ cord-276598-tm0yj2sn 309 20 aromatic aromatic JJ cord-276598-tm0yj2sn 309 21 secondary secondary JJ cord-276598-tm0yj2sn 309 22 amines amine NNS cord-276598-tm0yj2sn 309 23 ( ( -LRB- cord-276598-tm0yj2sn 309 24 e.g. e.g. RB cord-276598-tm0yj2sn 309 25 , , , cord-276598-tm0yj2sn 309 26 indole indole NN cord-276598-tm0yj2sn 309 27 ) ) -RRB- cord-276598-tm0yj2sn 309 28 , , , cord-276598-tm0yj2sn 309 29 derivatives derivative NNS cord-276598-tm0yj2sn 309 30 of of IN cord-276598-tm0yj2sn 309 31 heterocyclic heterocyclic JJ cord-276598-tm0yj2sn 309 32 amines amine NNS cord-276598-tm0yj2sn 309 33 ( ( -LRB- cord-276598-tm0yj2sn 309 34 e.g. e.g. RB cord-276598-tm0yj2sn 309 35 , , , cord-276598-tm0yj2sn 309 36 furfurylamine furfurylamine NN cord-276598-tm0yj2sn 309 37 ) ) -RRB- cord-276598-tm0yj2sn 309 38 , , , cord-276598-tm0yj2sn 309 39 aliphatic aliphatic JJ cord-276598-tm0yj2sn 309 40 cyclic cyclic JJ cord-276598-tm0yj2sn 309 41 secondary secondary JJ cord-276598-tm0yj2sn 309 42 amines amine NNS cord-276598-tm0yj2sn 309 43 ( ( -LRB- cord-276598-tm0yj2sn 309 44 e.g. e.g. RB cord-276598-tm0yj2sn 309 45 , , , cord-276598-tm0yj2sn 309 46 1-benzhydrylpiperazine 1-benzhydrylpiperazine CD cord-276598-tm0yj2sn 309 47 ) ) -RRB- cord-276598-tm0yj2sn 310 1 , , , cord-276598-tm0yj2sn 310 2 tertiary tertiary JJ cord-276598-tm0yj2sn 310 3 amines amine NNS cord-276598-tm0yj2sn 310 4 ( ( -LRB- cord-276598-tm0yj2sn 310 5 e.g. e.g. RB cord-276598-tm0yj2sn 310 6 , , , cord-276598-tm0yj2sn 310 7 N N NNP cord-276598-tm0yj2sn 310 8 - - HYPH cord-276598-tm0yj2sn 310 9 methylhomopiperazine methylhomopiperazine NNP cord-276598-tm0yj2sn 310 10 ) ) -RRB- cord-276598-tm0yj2sn 310 11 , , , cord-276598-tm0yj2sn 310 12 or or CC cord-276598-tm0yj2sn 310 13 sulfoximine sulfoximine NNP cord-276598-tm0yj2sn 310 14 . . . cord-276598-tm0yj2sn 311 1 According accord VBG cord-276598-tm0yj2sn 311 2 to to IN cord-276598-tm0yj2sn 311 3 the the DT cord-276598-tm0yj2sn 311 4 article article NN cord-276598-tm0yj2sn 311 5 , , , cord-276598-tm0yj2sn 311 6 using use VBG cord-276598-tm0yj2sn 311 7 other other JJ cord-276598-tm0yj2sn 311 8 sources source NNS cord-276598-tm0yj2sn 311 9 of of IN cord-276598-tm0yj2sn 311 10 I -PRON- PRP cord-276598-tm0yj2sn 311 11 2 2 CD cord-276598-tm0yj2sn 311 12 such such JJ cord-276598-tm0yj2sn 311 13 as as IN cord-276598-tm0yj2sn 311 14 KI KI NNP cord-276598-tm0yj2sn 311 15 or or CC cord-276598-tm0yj2sn 311 16 N N NNP cord-276598-tm0yj2sn 311 17 - - HYPH cord-276598-tm0yj2sn 311 18 bromosuccinimide bromosuccinimide NN cord-276598-tm0yj2sn 311 19 ( ( -LRB- cord-276598-tm0yj2sn 311 20 NBS NBS NNP cord-276598-tm0yj2sn 311 21 ) ) -RRB- cord-276598-tm0yj2sn 311 22 for for IN cord-276598-tm0yj2sn 311 23 the the DT cord-276598-tm0yj2sn 311 24 reaction reaction NN cord-276598-tm0yj2sn 311 25 resulted result VBD cord-276598-tm0yj2sn 311 26 in in IN cord-276598-tm0yj2sn 311 27 decreased decreased JJ cord-276598-tm0yj2sn 311 28 yield yield NN cord-276598-tm0yj2sn 311 29 and and CC cord-276598-tm0yj2sn 311 30 trace trace NN cord-276598-tm0yj2sn 311 31 quantities quantity NNS cord-276598-tm0yj2sn 311 32 of of IN cord-276598-tm0yj2sn 311 33 the the DT cord-276598-tm0yj2sn 311 34 desired desire VBN cord-276598-tm0yj2sn 311 35 products product NNS cord-276598-tm0yj2sn 311 36 , , , cord-276598-tm0yj2sn 311 37 respectively respectively RB cord-276598-tm0yj2sn 311 38 . . . cord-276598-tm0yj2sn 312 1 Iodine iodine NN cord-276598-tm0yj2sn 312 2 - - HYPH cord-276598-tm0yj2sn 312 3 mediated mediate VBN cord-276598-tm0yj2sn 312 4 oxidative oxidative JJ cord-276598-tm0yj2sn 312 5 cross cross JJ cord-276598-tm0yj2sn 312 6 - - JJ cord-276598-tm0yj2sn 312 7 coupling coupling JJ cord-276598-tm0yj2sn 312 8 methods method NNS cord-276598-tm0yj2sn 312 9 offer offer VBP cord-276598-tm0yj2sn 312 10 better well JJR cord-276598-tm0yj2sn 312 11 routes route NNS cord-276598-tm0yj2sn 312 12 to to IN cord-276598-tm0yj2sn 312 13 P P NNP cord-276598-tm0yj2sn 312 14 - - HYPH cord-276598-tm0yj2sn 312 15 N n CD cord-276598-tm0yj2sn 312 16 compounds compound NNS cord-276598-tm0yj2sn 312 17 by by IN cord-276598-tm0yj2sn 312 18 eliminating eliminate VBG cord-276598-tm0yj2sn 312 19 toxic toxic JJ cord-276598-tm0yj2sn 312 20 halogenating halogenating NN cord-276598-tm0yj2sn 312 21 agents agent NNS cord-276598-tm0yj2sn 312 22 such such JJ cord-276598-tm0yj2sn 312 23 as as IN cord-276598-tm0yj2sn 312 24 CCl CCl NNS cord-276598-tm0yj2sn 312 25 4 4 CD cord-276598-tm0yj2sn 312 26 in in IN cord-276598-tm0yj2sn 312 27 the the DT cord-276598-tm0yj2sn 312 28 synthetic synthetic JJ cord-276598-tm0yj2sn 312 29 processes process NNS cord-276598-tm0yj2sn 312 30 . . . cord-276598-tm0yj2sn 313 1 The the DT cord-276598-tm0yj2sn 313 2 method method NN cord-276598-tm0yj2sn 313 3 also also RB cord-276598-tm0yj2sn 313 4 uses use VBZ cord-276598-tm0yj2sn 313 5 inexpensive inexpensive JJ cord-276598-tm0yj2sn 313 6 oxidants oxidant NNS cord-276598-tm0yj2sn 313 7 without without IN cord-276598-tm0yj2sn 313 8 additives additive NNS cord-276598-tm0yj2sn 313 9 and and CC cord-276598-tm0yj2sn 313 10 generates generate VBZ cord-276598-tm0yj2sn 313 11 water water NN cord-276598-tm0yj2sn 313 12 or or CC cord-276598-tm0yj2sn 313 13 alkanol alkanol NN cord-276598-tm0yj2sn 313 14 as as IN cord-276598-tm0yj2sn 313 15 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 313 16 waste waste NN cord-276598-tm0yj2sn 313 17 . . . cord-276598-tm0yj2sn 314 1 However however RB cord-276598-tm0yj2sn 314 2 , , , cord-276598-tm0yj2sn 314 3 the the DT cord-276598-tm0yj2sn 314 4 synthetic synthetic JJ cord-276598-tm0yj2sn 314 5 routes route NNS cord-276598-tm0yj2sn 314 6 are be VBP cord-276598-tm0yj2sn 314 7 prone prone JJ cord-276598-tm0yj2sn 314 8 to to IN cord-276598-tm0yj2sn 314 9 the the DT cord-276598-tm0yj2sn 314 10 formation formation NN cord-276598-tm0yj2sn 314 11 of of IN cord-276598-tm0yj2sn 314 12 many many JJ cord-276598-tm0yj2sn 314 13 undesired undesired JJ cord-276598-tm0yj2sn 314 14 side side NN cord-276598-tm0yj2sn 314 15 products product NNS cord-276598-tm0yj2sn 314 16 , , , cord-276598-tm0yj2sn 314 17 suffer suffer VBP cord-276598-tm0yj2sn 314 18 from from IN cord-276598-tm0yj2sn 314 19 low low JJ cord-276598-tm0yj2sn 314 20 yields yield NNS cord-276598-tm0yj2sn 314 21 , , , cord-276598-tm0yj2sn 314 22 and and CC cord-276598-tm0yj2sn 314 23 sometimes sometimes RB cord-276598-tm0yj2sn 314 24 have have VBP cord-276598-tm0yj2sn 314 25 limited limit VBN cord-276598-tm0yj2sn 314 26 applicability applicability NN cord-276598-tm0yj2sn 314 27 . . . cord-276598-tm0yj2sn 315 1 The the DT cord-276598-tm0yj2sn 315 2 aerobic aerobic JJ cord-276598-tm0yj2sn 315 3 oxidative oxidative JJ cord-276598-tm0yj2sn 315 4 coupling coupling NN cord-276598-tm0yj2sn 315 5 of of IN cord-276598-tm0yj2sn 315 6 amines amine NNS cord-276598-tm0yj2sn 315 7 and and CC cord-276598-tm0yj2sn 315 8 disubstituted disubstituted JJ cord-276598-tm0yj2sn 315 9 H H NNP cord-276598-tm0yj2sn 315 10 - - HYPH cord-276598-tm0yj2sn 315 11 phosphonates phosphonates NNP cord-276598-tm0yj2sn 315 12 ( ( -LRB- cord-276598-tm0yj2sn 315 13 H h NN cord-276598-tm0yj2sn 315 14 - - HYPH cord-276598-tm0yj2sn 315 15 P p NN cord-276598-tm0yj2sn 315 16 ) ) -RRB- cord-276598-tm0yj2sn 316 1 ( ( -LRB- cord-276598-tm0yj2sn 316 2 RO RO NNP cord-276598-tm0yj2sn 316 3 ) ) -RRB- cord-276598-tm0yj2sn 316 4 2 2 CD cord-276598-tm0yj2sn 317 1 P(O)H p(o)h NN cord-276598-tm0yj2sn 318 1 ( ( -LRB- cord-276598-tm0yj2sn 318 2 R r NN cord-276598-tm0yj2sn 318 3 = = NFP cord-276598-tm0yj2sn 319 1 Me -PRON- PRP cord-276598-tm0yj2sn 319 2 , , , cord-276598-tm0yj2sn 319 3 Et Et NNP cord-276598-tm0yj2sn 319 4 , , , cord-276598-tm0yj2sn 319 5 i i NN cord-276598-tm0yj2sn 319 6 - - HYPH cord-276598-tm0yj2sn 319 7 Pr pr NN cord-276598-tm0yj2sn 319 8 ; ; : cord-276598-tm0yj2sn 319 9 1 1 CD cord-276598-tm0yj2sn 319 10 eq eq NN cord-276598-tm0yj2sn 319 11 . . . cord-276598-tm0yj2sn 319 12 ) ) -RRB- cord-276598-tm0yj2sn 320 1 in in IN cord-276598-tm0yj2sn 320 2 the the DT cord-276598-tm0yj2sn 320 3 presence presence NN cord-276598-tm0yj2sn 320 4 of of IN cord-276598-tm0yj2sn 320 5 copper copper NN cord-276598-tm0yj2sn 320 6 catalysts catalyst NNS cord-276598-tm0yj2sn 320 7 to to TO cord-276598-tm0yj2sn 320 8 synthesize synthesize VB cord-276598-tm0yj2sn 320 9 P p NN cord-276598-tm0yj2sn 320 10 - - HYPH cord-276598-tm0yj2sn 320 11 Ns Ns NNP cord-276598-tm0yj2sn 320 12 was be VBD cord-276598-tm0yj2sn 320 13 reported report VBN cord-276598-tm0yj2sn 320 14 by by IN cord-276598-tm0yj2sn 320 15 Hayes Hayes NNP cord-276598-tm0yj2sn 320 16 and and CC cord-276598-tm0yj2sn 320 17 coworkers coworker NNS cord-276598-tm0yj2sn 320 18 ( ( -LRB- cord-276598-tm0yj2sn 320 19 Table table NN cord-276598-tm0yj2sn 320 20 1 1 CD cord-276598-tm0yj2sn 320 21 , , , cord-276598-tm0yj2sn 320 22 route route VBP cord-276598-tm0yj2sn 320 23 a a DT cord-276598-tm0yj2sn 320 24 ) ) -RRB- cord-276598-tm0yj2sn 320 25 [ [ -LRB- cord-276598-tm0yj2sn 320 26 103 103 CD cord-276598-tm0yj2sn 320 27 ] ] -RRB- cord-276598-tm0yj2sn 320 28 . . . cord-276598-tm0yj2sn 321 1 The the DT cord-276598-tm0yj2sn 321 2 authors author NNS cord-276598-tm0yj2sn 321 3 reported report VBD cord-276598-tm0yj2sn 321 4 that that IN cord-276598-tm0yj2sn 321 5 the the DT cord-276598-tm0yj2sn 321 6 ligands ligand NNS cord-276598-tm0yj2sn 321 7 on on IN cord-276598-tm0yj2sn 321 8 the the DT cord-276598-tm0yj2sn 321 9 copper copper NN cord-276598-tm0yj2sn 321 10 catalyst catalyst NN cord-276598-tm0yj2sn 321 11 were be VBD cord-276598-tm0yj2sn 321 12 important important JJ cord-276598-tm0yj2sn 321 13 in in IN cord-276598-tm0yj2sn 321 14 the the DT cord-276598-tm0yj2sn 321 15 reaction reaction NN cord-276598-tm0yj2sn 321 16 , , , cord-276598-tm0yj2sn 321 17 but but CC cord-276598-tm0yj2sn 321 18 not not RB cord-276598-tm0yj2sn 321 19 the the DT cord-276598-tm0yj2sn 321 20 initial initial JJ cord-276598-tm0yj2sn 321 21 oxidation oxidation NN cord-276598-tm0yj2sn 321 22 state state NN cord-276598-tm0yj2sn 321 23 of of IN cord-276598-tm0yj2sn 321 24 copper copper NN cord-276598-tm0yj2sn 321 25 catalyst catalyst NN cord-276598-tm0yj2sn 321 26 , , , cord-276598-tm0yj2sn 321 27 and and CC cord-276598-tm0yj2sn 321 28 that that IN cord-276598-tm0yj2sn 321 29 the the DT cord-276598-tm0yj2sn 321 30 primary primary JJ cord-276598-tm0yj2sn 321 31 amines amine NNS cord-276598-tm0yj2sn 321 32 coupled couple VBN cord-276598-tm0yj2sn 321 33 better well RBR cord-276598-tm0yj2sn 321 34 than than IN cord-276598-tm0yj2sn 321 35 the the DT cord-276598-tm0yj2sn 321 36 secondary secondary JJ cord-276598-tm0yj2sn 321 37 and and CC cord-276598-tm0yj2sn 321 38 tertiary tertiary JJ cord-276598-tm0yj2sn 321 39 amines amine NNS cord-276598-tm0yj2sn 321 40 due due IN cord-276598-tm0yj2sn 321 41 to to IN cord-276598-tm0yj2sn 321 42 the the DT cord-276598-tm0yj2sn 321 43 reduced reduce VBN cord-276598-tm0yj2sn 321 44 steric steric JJ cord-276598-tm0yj2sn 321 45 hindrance hindrance NN cord-276598-tm0yj2sn 321 46 . . . cord-276598-tm0yj2sn 322 1 The the DT cord-276598-tm0yj2sn 322 2 method method NN cord-276598-tm0yj2sn 322 3 was be VBD cord-276598-tm0yj2sn 322 4 slightly slightly RB cord-276598-tm0yj2sn 322 5 modified modify VBN cord-276598-tm0yj2sn 322 6 for for IN cord-276598-tm0yj2sn 322 7 the the DT cord-276598-tm0yj2sn 322 8 synthesis synthesis NN cord-276598-tm0yj2sn 322 9 of of IN cord-276598-tm0yj2sn 322 10 some some DT cord-276598-tm0yj2sn 322 11 important important JJ cord-276598-tm0yj2sn 322 12 phosphoryl phosphoryl NN cord-276598-tm0yj2sn 322 13 amino amino NN cord-276598-tm0yj2sn 322 14 compounds compound NNS cord-276598-tm0yj2sn 322 15 such such JJ cord-276598-tm0yj2sn 322 16 as as IN cord-276598-tm0yj2sn 322 17 ethyl ethyl NN cord-276598-tm0yj2sn 322 18 ( ( -LRB- cord-276598-tm0yj2sn 322 19 diethoxyphosphoryl)glycinate diethoxyphosphoryl)glycinate NNP cord-276598-tm0yj2sn 322 20 , , , cord-276598-tm0yj2sn 322 21 etc etc FW cord-276598-tm0yj2sn 322 22 . . . cord-276598-tm0yj2sn 323 1 ( ( -LRB- cord-276598-tm0yj2sn 323 2 12 12 CD cord-276598-tm0yj2sn 323 3 - - SYM cord-276598-tm0yj2sn 323 4 15 15 CD cord-276598-tm0yj2sn 323 5 ) ) -RRB- cord-276598-tm0yj2sn 323 6 ( ( -LRB- cord-276598-tm0yj2sn 323 7 Figure figure NN cord-276598-tm0yj2sn 323 8 6 6 CD cord-276598-tm0yj2sn 323 9 ) ) -RRB- cord-276598-tm0yj2sn 323 10 . . . cord-276598-tm0yj2sn 323 11 _SP cord-276598-tm0yj2sn 324 1 The the DT cord-276598-tm0yj2sn 324 2 aerobic aerobic JJ cord-276598-tm0yj2sn 324 3 oxidative oxidative JJ cord-276598-tm0yj2sn 324 4 coupling coupling NN cord-276598-tm0yj2sn 324 5 of of IN cord-276598-tm0yj2sn 324 6 amines amine NNS cord-276598-tm0yj2sn 324 7 and and CC cord-276598-tm0yj2sn 324 8 disubstituted disubstituted JJ cord-276598-tm0yj2sn 324 9 H H NNP cord-276598-tm0yj2sn 324 10 - - HYPH cord-276598-tm0yj2sn 324 11 phosphonates phosphonates NNP cord-276598-tm0yj2sn 324 12 ( ( -LRB- cord-276598-tm0yj2sn 324 13 H h NN cord-276598-tm0yj2sn 324 14 - - HYPH cord-276598-tm0yj2sn 324 15 P p NN cord-276598-tm0yj2sn 324 16 ) ) -RRB- cord-276598-tm0yj2sn 325 1 ( ( -LRB- cord-276598-tm0yj2sn 325 2 RO)2P(O)H ro)2p(o)h CD cord-276598-tm0yj2sn 326 1 ( ( -LRB- cord-276598-tm0yj2sn 326 2 R r NN cord-276598-tm0yj2sn 327 1 = = NFP cord-276598-tm0yj2sn 327 2 Me -PRON- PRP cord-276598-tm0yj2sn 327 3 , , , cord-276598-tm0yj2sn 327 4 Et Et NNP cord-276598-tm0yj2sn 327 5 , , , cord-276598-tm0yj2sn 327 6 i i NN cord-276598-tm0yj2sn 327 7 - - HYPH cord-276598-tm0yj2sn 327 8 Pr pr NN cord-276598-tm0yj2sn 327 9 ; ; : cord-276598-tm0yj2sn 327 10 1 1 CD cord-276598-tm0yj2sn 327 11 eq eq NN cord-276598-tm0yj2sn 327 12 . . . cord-276598-tm0yj2sn 327 13 ) ) -RRB- cord-276598-tm0yj2sn 328 1 in in IN cord-276598-tm0yj2sn 328 2 the the DT cord-276598-tm0yj2sn 328 3 presence presence NN cord-276598-tm0yj2sn 328 4 of of IN cord-276598-tm0yj2sn 328 5 copper copper NN cord-276598-tm0yj2sn 328 6 catalysts catalyst NNS cord-276598-tm0yj2sn 328 7 to to TO cord-276598-tm0yj2sn 328 8 synthesize synthesize VB cord-276598-tm0yj2sn 328 9 P p NN cord-276598-tm0yj2sn 328 10 - - HYPH cord-276598-tm0yj2sn 328 11 Ns Ns NNP cord-276598-tm0yj2sn 328 12 was be VBD cord-276598-tm0yj2sn 328 13 reported report VBN cord-276598-tm0yj2sn 328 14 by by IN cord-276598-tm0yj2sn 328 15 Hayes Hayes NNP cord-276598-tm0yj2sn 328 16 and and CC cord-276598-tm0yj2sn 328 17 coworkers coworker NNS cord-276598-tm0yj2sn 328 18 ( ( -LRB- cord-276598-tm0yj2sn 328 19 Table table NN cord-276598-tm0yj2sn 328 20 1 1 CD cord-276598-tm0yj2sn 328 21 , , , cord-276598-tm0yj2sn 328 22 route route VBP cord-276598-tm0yj2sn 328 23 a a DT cord-276598-tm0yj2sn 328 24 ) ) -RRB- cord-276598-tm0yj2sn 328 25 [ [ -LRB- cord-276598-tm0yj2sn 328 26 103 103 CD cord-276598-tm0yj2sn 328 27 ] ] -RRB- cord-276598-tm0yj2sn 328 28 . . . cord-276598-tm0yj2sn 329 1 The the DT cord-276598-tm0yj2sn 329 2 authors author NNS cord-276598-tm0yj2sn 329 3 reported report VBD cord-276598-tm0yj2sn 329 4 that that IN cord-276598-tm0yj2sn 329 5 the the DT cord-276598-tm0yj2sn 329 6 ligands ligand NNS cord-276598-tm0yj2sn 329 7 on on IN cord-276598-tm0yj2sn 329 8 the the DT cord-276598-tm0yj2sn 329 9 copper copper NN cord-276598-tm0yj2sn 329 10 catalyst catalyst NN cord-276598-tm0yj2sn 329 11 were be VBD cord-276598-tm0yj2sn 329 12 important important JJ cord-276598-tm0yj2sn 329 13 in in IN cord-276598-tm0yj2sn 329 14 the the DT cord-276598-tm0yj2sn 329 15 reaction reaction NN cord-276598-tm0yj2sn 329 16 , , , cord-276598-tm0yj2sn 329 17 but but CC cord-276598-tm0yj2sn 329 18 not not RB cord-276598-tm0yj2sn 329 19 the the DT cord-276598-tm0yj2sn 329 20 initial initial JJ cord-276598-tm0yj2sn 329 21 oxidation oxidation NN cord-276598-tm0yj2sn 329 22 state state NN cord-276598-tm0yj2sn 329 23 of of IN cord-276598-tm0yj2sn 329 24 copper copper NN cord-276598-tm0yj2sn 329 25 catalyst catalyst NN cord-276598-tm0yj2sn 329 26 , , , cord-276598-tm0yj2sn 329 27 and and CC cord-276598-tm0yj2sn 329 28 that that IN cord-276598-tm0yj2sn 329 29 the the DT cord-276598-tm0yj2sn 329 30 primary primary JJ cord-276598-tm0yj2sn 329 31 amines amine NNS cord-276598-tm0yj2sn 329 32 coupled couple VBN cord-276598-tm0yj2sn 329 33 better well RBR cord-276598-tm0yj2sn 329 34 than than IN cord-276598-tm0yj2sn 329 35 the the DT cord-276598-tm0yj2sn 329 36 secondary secondary JJ cord-276598-tm0yj2sn 329 37 and and CC cord-276598-tm0yj2sn 329 38 tertiary tertiary JJ cord-276598-tm0yj2sn 329 39 amines amine NNS cord-276598-tm0yj2sn 329 40 due due IN cord-276598-tm0yj2sn 329 41 to to IN cord-276598-tm0yj2sn 329 42 the the DT cord-276598-tm0yj2sn 329 43 reduced reduce VBN cord-276598-tm0yj2sn 329 44 steric steric JJ cord-276598-tm0yj2sn 329 45 hindrance hindrance NN cord-276598-tm0yj2sn 329 46 . . . cord-276598-tm0yj2sn 330 1 The the DT cord-276598-tm0yj2sn 330 2 method method NN cord-276598-tm0yj2sn 330 3 was be VBD cord-276598-tm0yj2sn 330 4 slightly slightly RB cord-276598-tm0yj2sn 330 5 modified modify VBN cord-276598-tm0yj2sn 330 6 for for IN cord-276598-tm0yj2sn 330 7 the the DT cord-276598-tm0yj2sn 330 8 synthesis synthesis NN cord-276598-tm0yj2sn 330 9 of of IN cord-276598-tm0yj2sn 330 10 some some DT cord-276598-tm0yj2sn 330 11 important important JJ cord-276598-tm0yj2sn 330 12 phosphoryl phosphoryl NN cord-276598-tm0yj2sn 330 13 amino amino NN cord-276598-tm0yj2sn 330 14 compounds compound NNS cord-276598-tm0yj2sn 330 15 such such JJ cord-276598-tm0yj2sn 330 16 as as IN cord-276598-tm0yj2sn 330 17 ethyl ethyl NN cord-276598-tm0yj2sn 330 18 ( ( -LRB- cord-276598-tm0yj2sn 330 19 diethoxyphosphoryl)glycinate diethoxyphosphoryl)glycinate NNP cord-276598-tm0yj2sn 330 20 , , , cord-276598-tm0yj2sn 330 21 etc etc FW cord-276598-tm0yj2sn 330 22 . . . cord-276598-tm0yj2sn 331 1 ( ( -LRB- cord-276598-tm0yj2sn 331 2 12 12 CD cord-276598-tm0yj2sn 331 3 - - SYM cord-276598-tm0yj2sn 331 4 15 15 CD cord-276598-tm0yj2sn 331 5 ) ) -RRB- cord-276598-tm0yj2sn 331 6 ( ( -LRB- cord-276598-tm0yj2sn 331 7 Figure figure NN cord-276598-tm0yj2sn 331 8 6 6 CD cord-276598-tm0yj2sn 331 9 ) ) -RRB- cord-276598-tm0yj2sn 331 10 . . . cord-276598-tm0yj2sn 332 1 ( ( -LRB- cord-276598-tm0yj2sn 332 2 Table table NN cord-276598-tm0yj2sn 332 3 1 1 CD cord-276598-tm0yj2sn 332 4 , , , cord-276598-tm0yj2sn 332 5 route route NN cord-276598-tm0yj2sn 332 6 b b NN cord-276598-tm0yj2sn 332 7 ) ) -RRB- cord-276598-tm0yj2sn 332 8 [ [ -LRB- cord-276598-tm0yj2sn 332 9 104 104 CD cord-276598-tm0yj2sn 332 10 ] ] -RRB- cord-276598-tm0yj2sn 332 11 . . . cord-276598-tm0yj2sn 333 1 Although although IN cord-276598-tm0yj2sn 333 2 paraor paraor NNP cord-276598-tm0yj2sn 333 3 meta meta NNP cord-276598-tm0yj2sn 333 4 - - HYPH cord-276598-tm0yj2sn 333 5 substituted substitute VBN cord-276598-tm0yj2sn 333 6 aryl aryl NN cord-276598-tm0yj2sn 333 7 amines amine NNS cord-276598-tm0yj2sn 333 8 were be VBD cord-276598-tm0yj2sn 333 9 very very RB cord-276598-tm0yj2sn 333 10 effective effective JJ cord-276598-tm0yj2sn 333 11 substrates substrate NNS cord-276598-tm0yj2sn 333 12 in in IN cord-276598-tm0yj2sn 333 13 this this DT cord-276598-tm0yj2sn 333 14 reaction reaction NN cord-276598-tm0yj2sn 333 15 , , , cord-276598-tm0yj2sn 333 16 the the DT cord-276598-tm0yj2sn 333 17 conversions conversion NNS cord-276598-tm0yj2sn 333 18 observed observe VBN cord-276598-tm0yj2sn 333 19 with with IN cord-276598-tm0yj2sn 333 20 ortho ortho NNP cord-276598-tm0yj2sn 333 21 - - HYPH cord-276598-tm0yj2sn 333 22 substituted substitute VBN cord-276598-tm0yj2sn 333 23 aryl aryl NN cord-276598-tm0yj2sn 333 24 amines amine NNS cord-276598-tm0yj2sn 333 25 or or CC cord-276598-tm0yj2sn 333 26 aryl aryl NN cord-276598-tm0yj2sn 334 1 amines amine NNS cord-276598-tm0yj2sn 334 2 with with IN cord-276598-tm0yj2sn 334 3 strong strong JJ cord-276598-tm0yj2sn 334 4 electron electron NN cord-276598-tm0yj2sn 334 5 - - HYPH cord-276598-tm0yj2sn 334 6 withdrawing withdraw VBG cord-276598-tm0yj2sn 334 7 Another another DT cord-276598-tm0yj2sn 334 8 copper copper NN cord-276598-tm0yj2sn 334 9 - - HYPH cord-276598-tm0yj2sn 334 10 catalyzed catalyze VBN cord-276598-tm0yj2sn 334 11 aerobic aerobic JJ cord-276598-tm0yj2sn 334 12 oxidative oxidative JJ cord-276598-tm0yj2sn 334 13 cross cross JJ cord-276598-tm0yj2sn 334 14 - - JJ cord-276598-tm0yj2sn 334 15 coupling coupling JJ cord-276598-tm0yj2sn 334 16 reaction reaction NN cord-276598-tm0yj2sn 334 17 reported report VBN cord-276598-tm0yj2sn 334 18 by by IN cord-276598-tm0yj2sn 334 19 Wang Wang NNP cord-276598-tm0yj2sn 334 20 et et NNP cord-276598-tm0yj2sn 334 21 al al NNP cord-276598-tm0yj2sn 334 22 . . . cord-276598-tm0yj2sn 335 1 in in IN cord-276598-tm0yj2sn 335 2 2013 2013 CD cord-276598-tm0yj2sn 335 3 involved involve VBD cord-276598-tm0yj2sn 335 4 the the DT cord-276598-tm0yj2sn 335 5 coupling coupling NN cord-276598-tm0yj2sn 335 6 of of IN cord-276598-tm0yj2sn 335 7 aryl aryl NN cord-276598-tm0yj2sn 335 8 amines amine NNS cord-276598-tm0yj2sn 335 9 ( ( -LRB- cord-276598-tm0yj2sn 335 10 1.5 1.5 CD cord-276598-tm0yj2sn 335 11 eq eq NN cord-276598-tm0yj2sn 335 12 . . . cord-276598-tm0yj2sn 335 13 ) ) -RRB- cord-276598-tm0yj2sn 335 14 and and CC cord-276598-tm0yj2sn 335 15 dialkyl dialkyl NNP cord-276598-tm0yj2sn 335 16 H H NNP cord-276598-tm0yj2sn 335 17 - - HYPH cord-276598-tm0yj2sn 335 18 phosphonates phosphonates NNP cord-276598-tm0yj2sn 335 19 ( ( -LRB- cord-276598-tm0yj2sn 335 20 RO RO NNP cord-276598-tm0yj2sn 335 21 ) ) -RRB- cord-276598-tm0yj2sn 335 22 2 2 CD cord-276598-tm0yj2sn 336 1 P(O)H p(o)h NN cord-276598-tm0yj2sn 337 1 ( ( -LRB- cord-276598-tm0yj2sn 337 2 R r NN cord-276598-tm0yj2sn 337 3 = = FW cord-276598-tm0yj2sn 337 4 Et Et NNP cord-276598-tm0yj2sn 337 5 , , , cord-276598-tm0yj2sn 337 6 i i NN cord-276598-tm0yj2sn 337 7 - - HYPH cord-276598-tm0yj2sn 337 8 Pr Pr NNP cord-276598-tm0yj2sn 337 9 , , , cord-276598-tm0yj2sn 337 10 Bu Bu NNP cord-276598-tm0yj2sn 337 11 ; ; : cord-276598-tm0yj2sn 337 12 1 1 CD cord-276598-tm0yj2sn 337 13 eq eq NN cord-276598-tm0yj2sn 337 14 . . . cord-276598-tm0yj2sn 337 15 ) ) -RRB- cord-276598-tm0yj2sn 337 16 in in IN cord-276598-tm0yj2sn 337 17 the the DT cord-276598-tm0yj2sn 337 18 presence presence NN cord-276598-tm0yj2sn 337 19 of of IN cord-276598-tm0yj2sn 337 20 CuBr CuBr NNP cord-276598-tm0yj2sn 337 21 ( ( -LRB- cord-276598-tm0yj2sn 337 22 5 5 CD cord-276598-tm0yj2sn 337 23 mol% mol% CD cord-276598-tm0yj2sn 337 24 ) ) -RRB- cord-276598-tm0yj2sn 337 25 to to TO cord-276598-tm0yj2sn 337 26 give give VB cord-276598-tm0yj2sn 337 27 P p NN cord-276598-tm0yj2sn 337 28 - - HYPH cord-276598-tm0yj2sn 337 29 Ns Ns NNP cord-276598-tm0yj2sn 337 30 ( ( -LRB- cord-276598-tm0yj2sn 337 31 Table table NN cord-276598-tm0yj2sn 337 32 1 1 CD cord-276598-tm0yj2sn 337 33 , , , cord-276598-tm0yj2sn 337 34 route route NN cord-276598-tm0yj2sn 337 35 b b NN cord-276598-tm0yj2sn 337 36 ) ) -RRB- cord-276598-tm0yj2sn 337 37 [ [ -LRB- cord-276598-tm0yj2sn 337 38 104 104 CD cord-276598-tm0yj2sn 337 39 ] ] -RRB- cord-276598-tm0yj2sn 337 40 . . . cord-276598-tm0yj2sn 338 1 Although although IN cord-276598-tm0yj2sn 338 2 paraor paraor NNP cord-276598-tm0yj2sn 338 3 meta meta NNP cord-276598-tm0yj2sn 338 4 - - HYPH cord-276598-tm0yj2sn 338 5 substituted substitute VBN cord-276598-tm0yj2sn 338 6 aryl aryl NN cord-276598-tm0yj2sn 338 7 amines amine NNS cord-276598-tm0yj2sn 338 8 were be VBD cord-276598-tm0yj2sn 338 9 very very RB cord-276598-tm0yj2sn 338 10 effective effective JJ cord-276598-tm0yj2sn 338 11 substrates substrate NNS cord-276598-tm0yj2sn 338 12 in in IN cord-276598-tm0yj2sn 338 13 this this DT cord-276598-tm0yj2sn 338 14 reaction reaction NN cord-276598-tm0yj2sn 338 15 , , , cord-276598-tm0yj2sn 338 16 the the DT cord-276598-tm0yj2sn 338 17 conversions conversion NNS cord-276598-tm0yj2sn 338 18 observed observe VBN cord-276598-tm0yj2sn 338 19 with with IN cord-276598-tm0yj2sn 338 20 ortho ortho NNP cord-276598-tm0yj2sn 338 21 - - HYPH cord-276598-tm0yj2sn 338 22 substituted substitute VBN cord-276598-tm0yj2sn 338 23 aryl aryl NN cord-276598-tm0yj2sn 338 24 amines amine NNS cord-276598-tm0yj2sn 338 25 or or CC cord-276598-tm0yj2sn 338 26 aryl aryl NN cord-276598-tm0yj2sn 339 1 amines amine NNS cord-276598-tm0yj2sn 339 2 with with IN cord-276598-tm0yj2sn 339 3 strong strong JJ cord-276598-tm0yj2sn 339 4 electron electron NN cord-276598-tm0yj2sn 339 5 - - HYPH cord-276598-tm0yj2sn 339 6 withdrawing withdraw VBG cord-276598-tm0yj2sn 339 7 substituents substituent NNS cord-276598-tm0yj2sn 339 8 ( ( -LRB- cord-276598-tm0yj2sn 339 9 e.g. e.g. RB cord-276598-tm0yj2sn 339 10 , , , cord-276598-tm0yj2sn 339 11 4-nitroaniline 4-nitroaniline CD cord-276598-tm0yj2sn 339 12 ) ) -RRB- cord-276598-tm0yj2sn 339 13 as as RB cord-276598-tm0yj2sn 339 14 well well RB cord-276598-tm0yj2sn 339 15 as as IN cord-276598-tm0yj2sn 339 16 alkylamines alkylamine NNS cord-276598-tm0yj2sn 339 17 were be VBD cord-276598-tm0yj2sn 339 18 very very RB cord-276598-tm0yj2sn 339 19 poor poor JJ cord-276598-tm0yj2sn 339 20 . . . cord-276598-tm0yj2sn 340 1 The the DT cord-276598-tm0yj2sn 340 2 effectiveness effectiveness NN cord-276598-tm0yj2sn 340 3 of of IN cord-276598-tm0yj2sn 340 4 the the DT cord-276598-tm0yj2sn 340 5 reaction reaction NN cord-276598-tm0yj2sn 340 6 with with IN cord-276598-tm0yj2sn 340 7 diaryl diaryl NNP cord-276598-tm0yj2sn 340 8 H H NNP cord-276598-tm0yj2sn 340 9 - - HYPH cord-276598-tm0yj2sn 340 10 phosphonates phosphonates NNP cord-276598-tm0yj2sn 340 11 was be VBD cord-276598-tm0yj2sn 340 12 not not RB cord-276598-tm0yj2sn 340 13 reported report VBN cord-276598-tm0yj2sn 340 14 . . . cord-276598-tm0yj2sn 341 1 In in IN cord-276598-tm0yj2sn 341 2 2015 2015 CD cord-276598-tm0yj2sn 341 3 , , , cord-276598-tm0yj2sn 341 4 Fe Fe NNP cord-276598-tm0yj2sn 341 5 3 3 CD cord-276598-tm0yj2sn 341 6 O o NN cord-276598-tm0yj2sn 341 7 4 4 CD cord-276598-tm0yj2sn 341 8 @MgO @MgO NNS cord-276598-tm0yj2sn 341 9 nanoparticles nanoparticle NNS cord-276598-tm0yj2sn 341 10 were be VBD cord-276598-tm0yj2sn 341 11 used use VBN cord-276598-tm0yj2sn 341 12 as as IN cord-276598-tm0yj2sn 341 13 a a DT cord-276598-tm0yj2sn 341 14 catalyst catalyst NN cord-276598-tm0yj2sn 341 15 to to TO cord-276598-tm0yj2sn 341 16 synthesize synthesize VB cord-276598-tm0yj2sn 341 17 P P NNP cord-276598-tm0yj2sn 341 18 - - HYPH cord-276598-tm0yj2sn 341 19 N N NNP cord-276598-tm0yj2sn 341 20 from from IN cord-276598-tm0yj2sn 341 21 primary primary JJ cord-276598-tm0yj2sn 341 22 amines amine NNS cord-276598-tm0yj2sn 341 23 and and CC cord-276598-tm0yj2sn 341 24 H h NN cord-276598-tm0yj2sn 341 25 - - HYPH cord-276598-tm0yj2sn 341 26 P p NN cord-276598-tm0yj2sn 341 27 via via IN cord-276598-tm0yj2sn 341 28 the the DT cord-276598-tm0yj2sn 341 29 Atherton Atherton NNP cord-276598-tm0yj2sn 341 30 - - HYPH cord-276598-tm0yj2sn 341 31 Todd Todd NNP cord-276598-tm0yj2sn 341 32 coupling coupling NN cord-276598-tm0yj2sn 341 33 reaction reaction NN cord-276598-tm0yj2sn 341 34 with with IN cord-276598-tm0yj2sn 341 35 CCl CCl NNS cord-276598-tm0yj2sn 341 36 4 4 CD cord-276598-tm0yj2sn 341 37 ( ( -LRB- cord-276598-tm0yj2sn 341 38 Table table NN cord-276598-tm0yj2sn 341 39 1 1 CD cord-276598-tm0yj2sn 341 40 , , , cord-276598-tm0yj2sn 341 41 route route NN cord-276598-tm0yj2sn 341 42 c c NN cord-276598-tm0yj2sn 341 43 ) ) -RRB- cord-276598-tm0yj2sn 341 44 [ [ -LRB- cord-276598-tm0yj2sn 341 45 105 105 CD cord-276598-tm0yj2sn 341 46 ] ] -RRB- cord-276598-tm0yj2sn 341 47 . . . cord-276598-tm0yj2sn 342 1 After after IN cord-276598-tm0yj2sn 342 2 column column NN cord-276598-tm0yj2sn 342 3 chromatography chromatography NN cord-276598-tm0yj2sn 342 4 ( ( -LRB- cord-276598-tm0yj2sn 342 5 on on IN cord-276598-tm0yj2sn 342 6 silica silica NN cord-276598-tm0yj2sn 342 7 ) ) -RRB- cord-276598-tm0yj2sn 342 8 , , , cord-276598-tm0yj2sn 342 9 P P NNP cord-276598-tm0yj2sn 342 10 - - HYPH cord-276598-tm0yj2sn 342 11 Ns Ns NNP cord-276598-tm0yj2sn 342 12 were be VBD cord-276598-tm0yj2sn 342 13 isolated isolate VBN cord-276598-tm0yj2sn 342 14 in in IN cord-276598-tm0yj2sn 342 15 52 52 CD cord-276598-tm0yj2sn 342 16 - - SYM cord-276598-tm0yj2sn 342 17 85 85 CD cord-276598-tm0yj2sn 342 18 % % NN cord-276598-tm0yj2sn 342 19 yield yield NN cord-276598-tm0yj2sn 342 20 . . . cord-276598-tm0yj2sn 343 1 The the DT cord-276598-tm0yj2sn 343 2 Fe Fe NNP cord-276598-tm0yj2sn 343 3 3 3 CD cord-276598-tm0yj2sn 343 4 O o NN cord-276598-tm0yj2sn 343 5 4 4 CD cord-276598-tm0yj2sn 343 6 @MgO @MgO NNS cord-276598-tm0yj2sn 343 7 nanoparticles nanoparticle NNS cord-276598-tm0yj2sn 343 8 were be VBD cord-276598-tm0yj2sn 343 9 recycled recycle VBN cord-276598-tm0yj2sn 343 10 by by IN cord-276598-tm0yj2sn 343 11 washing wash VBG cord-276598-tm0yj2sn 343 12 successively successively RB cord-276598-tm0yj2sn 343 13 with with IN cord-276598-tm0yj2sn 343 14 H h NN cord-276598-tm0yj2sn 343 15 2 2 CD cord-276598-tm0yj2sn 343 16 O o NN cord-276598-tm0yj2sn 343 17 and and CC cord-276598-tm0yj2sn 343 18 MeOH MeOH NNS cord-276598-tm0yj2sn 343 19 and and CC cord-276598-tm0yj2sn 343 20 drying dry VBG cord-276598-tm0yj2sn 343 21 before before IN cord-276598-tm0yj2sn 343 22 reuse reuse NN cord-276598-tm0yj2sn 343 23 . . . cord-276598-tm0yj2sn 344 1 Although although IN cord-276598-tm0yj2sn 344 2 the the DT cord-276598-tm0yj2sn 344 3 scope scope NN cord-276598-tm0yj2sn 344 4 of of IN cord-276598-tm0yj2sn 344 5 the the DT cord-276598-tm0yj2sn 344 6 transformation transformation NN cord-276598-tm0yj2sn 344 7 was be VBD cord-276598-tm0yj2sn 344 8 not not RB cord-276598-tm0yj2sn 344 9 challenged challenge VBN cord-276598-tm0yj2sn 344 10 by by IN cord-276598-tm0yj2sn 344 11 investigating investigate VBG cord-276598-tm0yj2sn 344 12 aromatic aromatic JJ cord-276598-tm0yj2sn 344 13 H H NNP cord-276598-tm0yj2sn 344 14 - - HYPH cord-276598-tm0yj2sn 344 15 Ps Ps NNP cord-276598-tm0yj2sn 344 16 , , , cord-276598-tm0yj2sn 344 17 this this DT cord-276598-tm0yj2sn 344 18 route route NN cord-276598-tm0yj2sn 344 19 offers offer VBZ cord-276598-tm0yj2sn 344 20 some some DT cord-276598-tm0yj2sn 344 21 advantages advantage NNS cord-276598-tm0yj2sn 344 22 , , , cord-276598-tm0yj2sn 344 23 such such JJ cord-276598-tm0yj2sn 344 24 as as IN cord-276598-tm0yj2sn 344 25 the the DT cord-276598-tm0yj2sn 344 26 use use NN cord-276598-tm0yj2sn 344 27 of of IN cord-276598-tm0yj2sn 344 28 a a DT cord-276598-tm0yj2sn 344 29 low low JJ cord-276598-tm0yj2sn 344 30 - - HYPH cord-276598-tm0yj2sn 344 31 cost cost NN cord-276598-tm0yj2sn 344 32 reusable reusable JJ cord-276598-tm0yj2sn 344 33 catalyst catalyst NN cord-276598-tm0yj2sn 344 34 with with IN cord-276598-tm0yj2sn 344 35 proven prove VBN cord-276598-tm0yj2sn 344 36 activity activity NN cord-276598-tm0yj2sn 344 37 for for IN cord-276598-tm0yj2sn 344 38 up up IN cord-276598-tm0yj2sn 344 39 to to TO cord-276598-tm0yj2sn 344 40 four four CD cord-276598-tm0yj2sn 344 41 consecutive consecutive JJ cord-276598-tm0yj2sn 344 42 reactions reaction NNS cord-276598-tm0yj2sn 344 43 . . . cord-276598-tm0yj2sn 345 1 Purohit Purohit NNP cord-276598-tm0yj2sn 345 2 et et NNP cord-276598-tm0yj2sn 345 3 al al NNP cord-276598-tm0yj2sn 345 4 . . NNP cord-276598-tm0yj2sn 345 5 reported report VBD cord-276598-tm0yj2sn 345 6 a a DT cord-276598-tm0yj2sn 345 7 one one CD cord-276598-tm0yj2sn 345 8 - - HYPH cord-276598-tm0yj2sn 345 9 pot pot NN cord-276598-tm0yj2sn 345 10 synthesis synthesis NN cord-276598-tm0yj2sn 345 11 of of IN cord-276598-tm0yj2sn 345 12 P p NN cord-276598-tm0yj2sn 345 13 - - HYPH cord-276598-tm0yj2sn 345 14 Ns Ns NNP cord-276598-tm0yj2sn 345 15 from from IN cord-276598-tm0yj2sn 345 16 ( ( -LRB- cord-276598-tm0yj2sn 345 17 RO ro NN cord-276598-tm0yj2sn 345 18 ) ) -RRB- cord-276598-tm0yj2sn 345 19 2 2 CD cord-276598-tm0yj2sn 346 1 P(O)H p(o)h NN cord-276598-tm0yj2sn 347 1 ( ( -LRB- cord-276598-tm0yj2sn 347 2 R r NN cord-276598-tm0yj2sn 347 3 = = FW cord-276598-tm0yj2sn 347 4 Et Et NNP cord-276598-tm0yj2sn 347 5 , , , cord-276598-tm0yj2sn 347 6 Pr Pr NNP cord-276598-tm0yj2sn 347 7 , , , cord-276598-tm0yj2sn 347 8 i i NN cord-276598-tm0yj2sn 347 9 - - HYPH cord-276598-tm0yj2sn 347 10 Pr pr NN cord-276598-tm0yj2sn 347 11 ; ; : cord-276598-tm0yj2sn 347 12 1 1 CD cord-276598-tm0yj2sn 347 13 eq eq NN cord-276598-tm0yj2sn 347 14 . . . cord-276598-tm0yj2sn 347 15 ) ) -RRB- cord-276598-tm0yj2sn 347 16 and and CC cord-276598-tm0yj2sn 347 17 amine amine NN cord-276598-tm0yj2sn 347 18 in in IN cord-276598-tm0yj2sn 347 19 the the DT cord-276598-tm0yj2sn 347 20 presence presence NN cord-276598-tm0yj2sn 347 21 of of IN cord-276598-tm0yj2sn 347 22 CuCl CuCl NNP cord-276598-tm0yj2sn 347 23 2 2 CD cord-276598-tm0yj2sn 347 24 and and CC cord-276598-tm0yj2sn 347 25 Cs Cs NNP cord-276598-tm0yj2sn 347 26 2 2 CD cord-276598-tm0yj2sn 347 27 CO CO NNP cord-276598-tm0yj2sn 347 28 3 3 CD cord-276598-tm0yj2sn 347 29 ( ( -LRB- cord-276598-tm0yj2sn 347 30 Table table NN cord-276598-tm0yj2sn 347 31 1 1 CD cord-276598-tm0yj2sn 347 32 , , , cord-276598-tm0yj2sn 347 33 route route NN cord-276598-tm0yj2sn 347 34 d d NN cord-276598-tm0yj2sn 347 35 ) ) -RRB- cord-276598-tm0yj2sn 347 36 [ [ -LRB- cord-276598-tm0yj2sn 347 37 106 106 CD cord-276598-tm0yj2sn 347 38 ] ] -RRB- cord-276598-tm0yj2sn 347 39 . . . cord-276598-tm0yj2sn 348 1 The the DT cord-276598-tm0yj2sn 348 2 reported report VBN cord-276598-tm0yj2sn 348 3 yields yield NNS cord-276598-tm0yj2sn 348 4 for for IN cord-276598-tm0yj2sn 348 5 the the DT cord-276598-tm0yj2sn 348 6 variety variety NN cord-276598-tm0yj2sn 348 7 of of IN cord-276598-tm0yj2sn 348 8 desired desire VBN cord-276598-tm0yj2sn 348 9 products product NNS cord-276598-tm0yj2sn 348 10 were be VBD cord-276598-tm0yj2sn 348 11 in in IN cord-276598-tm0yj2sn 348 12 the the DT cord-276598-tm0yj2sn 348 13 range range NN cord-276598-tm0yj2sn 348 14 of of IN cord-276598-tm0yj2sn 348 15 25 25 CD cord-276598-tm0yj2sn 348 16 - - SYM cord-276598-tm0yj2sn 348 17 93 93 CD cord-276598-tm0yj2sn 348 18 % % NN cord-276598-tm0yj2sn 348 19 as as IN cord-276598-tm0yj2sn 348 20 determined determine VBN cord-276598-tm0yj2sn 348 21 by by IN cord-276598-tm0yj2sn 348 22 31 31 CD cord-276598-tm0yj2sn 348 23 P p NN cord-276598-tm0yj2sn 348 24 NMR nmr NN cord-276598-tm0yj2sn 348 25 spectroscopy spectroscopy NN cord-276598-tm0yj2sn 348 26 . . . cord-276598-tm0yj2sn 349 1 A a DT cord-276598-tm0yj2sn 349 2 Cu(II cu(ii NN cord-276598-tm0yj2sn 349 3 ) ) -RRB- cord-276598-tm0yj2sn 349 4 catalyst catalyst NN cord-276598-tm0yj2sn 349 5 , , , cord-276598-tm0yj2sn 349 6 a a DT cord-276598-tm0yj2sn 349 7 base base NN cord-276598-tm0yj2sn 349 8 , , , cord-276598-tm0yj2sn 349 9 and and CC cord-276598-tm0yj2sn 349 10 air air NN cord-276598-tm0yj2sn 349 11 as as IN cord-276598-tm0yj2sn 349 12 an an DT cord-276598-tm0yj2sn 349 13 oxidant oxidant NN cord-276598-tm0yj2sn 349 14 were be VBD cord-276598-tm0yj2sn 349 15 used use VBN cord-276598-tm0yj2sn 349 16 to to TO cord-276598-tm0yj2sn 349 17 synthesize synthesize VB cord-276598-tm0yj2sn 349 18 N N NNP cord-276598-tm0yj2sn 349 19 - - HYPH cord-276598-tm0yj2sn 349 20 acylphosphoramidates acylphosphoramidates NNP cord-276598-tm0yj2sn 349 21 ( ( -LRB- cord-276598-tm0yj2sn 349 22 AcP AcP NNP cord-276598-tm0yj2sn 349 23 - - HYPH cord-276598-tm0yj2sn 349 24 N N NNP cord-276598-tm0yj2sn 349 25 ) ) -RRB- cord-276598-tm0yj2sn 349 26 from from IN cord-276598-tm0yj2sn 349 27 ( ( -LRB- cord-276598-tm0yj2sn 349 28 RO RO NNP cord-276598-tm0yj2sn 349 29 ) ) -RRB- cord-276598-tm0yj2sn 349 30 2 2 CD cord-276598-tm0yj2sn 350 1 P(O)H p(o)h NN cord-276598-tm0yj2sn 351 1 ( ( -LRB- cord-276598-tm0yj2sn 351 2 R r NN cord-276598-tm0yj2sn 351 3 = = NFP cord-276598-tm0yj2sn 352 1 Me -PRON- PRP cord-276598-tm0yj2sn 352 2 , , , cord-276598-tm0yj2sn 352 3 Et Et NNP cord-276598-tm0yj2sn 352 4 , , , cord-276598-tm0yj2sn 352 5 i i NN cord-276598-tm0yj2sn 352 6 - - HYPH cord-276598-tm0yj2sn 352 7 Pr Pr NNP cord-276598-tm0yj2sn 352 8 , , , cord-276598-tm0yj2sn 352 9 Bu Bu NNP cord-276598-tm0yj2sn 352 10 ) ) -RRB- cord-276598-tm0yj2sn 352 11 and and CC cord-276598-tm0yj2sn 352 12 an an DT cord-276598-tm0yj2sn 352 13 amide amide NN cord-276598-tm0yj2sn 352 14 via via IN cord-276598-tm0yj2sn 352 15 an an DT cord-276598-tm0yj2sn 352 16 oxidative oxidative JJ cord-276598-tm0yj2sn 352 17 cross cross JJ cord-276598-tm0yj2sn 352 18 - - JJ cord-276598-tm0yj2sn 352 19 coupling coupling JJ cord-276598-tm0yj2sn 352 20 reaction reaction NN cord-276598-tm0yj2sn 352 21 according accord VBG cord-276598-tm0yj2sn 352 22 to to IN cord-276598-tm0yj2sn 352 23 Mizuno Mizuno NNP cord-276598-tm0yj2sn 352 24 et et NNP cord-276598-tm0yj2sn 352 25 al al NNP cord-276598-tm0yj2sn 352 26 . . . cord-276598-tm0yj2sn 353 1 ( ( -LRB- cord-276598-tm0yj2sn 353 2 Table table NN cord-276598-tm0yj2sn 353 3 1 1 CD cord-276598-tm0yj2sn 353 4 , , , cord-276598-tm0yj2sn 353 5 route route NN cord-276598-tm0yj2sn 353 6 e e NN cord-276598-tm0yj2sn 353 7 ) ) -RRB- cord-276598-tm0yj2sn 354 1 [ [ -LRB- cord-276598-tm0yj2sn 354 2 107 107 CD cord-276598-tm0yj2sn 354 3 ] ] -RRB- cord-276598-tm0yj2sn 354 4 . . . cord-276598-tm0yj2sn 355 1 The the DT cord-276598-tm0yj2sn 355 2 scope scope NN cord-276598-tm0yj2sn 355 3 of of IN cord-276598-tm0yj2sn 355 4 the the DT cord-276598-tm0yj2sn 355 5 reaction reaction NN cord-276598-tm0yj2sn 355 6 was be VBD cord-276598-tm0yj2sn 355 7 investigated investigate VBN cord-276598-tm0yj2sn 355 8 by by IN cord-276598-tm0yj2sn 355 9 changing change VBG cord-276598-tm0yj2sn 355 10 the the DT cord-276598-tm0yj2sn 355 11 R r NN cord-276598-tm0yj2sn 355 12 substituent substituent NN cord-276598-tm0yj2sn 355 13 as as RB cord-276598-tm0yj2sn 355 14 well well RB cord-276598-tm0yj2sn 355 15 as as IN cord-276598-tm0yj2sn 355 16 the the DT cord-276598-tm0yj2sn 355 17 nitrogen nitrogen NN cord-276598-tm0yj2sn 355 18 nucleophiles nucleophile NNS cord-276598-tm0yj2sn 355 19 ( ( -LRB- cord-276598-tm0yj2sn 355 20 e.g. e.g. RB cord-276598-tm0yj2sn 355 21 , , , cord-276598-tm0yj2sn 355 22 urea urea NN cord-276598-tm0yj2sn 355 23 , , , cord-276598-tm0yj2sn 355 24 oxazolidinone oxazolidinone NN cord-276598-tm0yj2sn 355 25 , , , cord-276598-tm0yj2sn 355 26 indole indole NN cord-276598-tm0yj2sn 355 27 , , , cord-276598-tm0yj2sn 355 28 pyrrolidinone pyrrolidinone NN cord-276598-tm0yj2sn 355 29 , , , cord-276598-tm0yj2sn 355 30 lactam lactam NNS cord-276598-tm0yj2sn 355 31 , , , cord-276598-tm0yj2sn 355 32 and and CC cord-276598-tm0yj2sn 355 33 sulfonamide sulfonamide NN cord-276598-tm0yj2sn 355 34 derivatives derivative NNS cord-276598-tm0yj2sn 355 35 ) ) -RRB- cord-276598-tm0yj2sn 355 36 . . . cord-276598-tm0yj2sn 356 1 Column column NN cord-276598-tm0yj2sn 356 2 chromatography chromatography NN cord-276598-tm0yj2sn 356 3 ( ( -LRB- cord-276598-tm0yj2sn 356 4 on on IN cord-276598-tm0yj2sn 356 5 silica silica NN cord-276598-tm0yj2sn 356 6 ) ) -RRB- cord-276598-tm0yj2sn 356 7 using use VBG cord-276598-tm0yj2sn 356 8 different different JJ cord-276598-tm0yj2sn 356 9 solvent solvent NN cord-276598-tm0yj2sn 356 10 mixtures mixture NNS cord-276598-tm0yj2sn 356 11 was be VBD cord-276598-tm0yj2sn 356 12 used use VBN cord-276598-tm0yj2sn 356 13 to to TO cord-276598-tm0yj2sn 356 14 purify purify VB cord-276598-tm0yj2sn 356 15 the the DT cord-276598-tm0yj2sn 356 16 desired desire VBN cord-276598-tm0yj2sn 356 17 P P NNP cord-276598-tm0yj2sn 356 18 - - HYPH cord-276598-tm0yj2sn 356 19 Ns Ns NNP cord-276598-tm0yj2sn 356 20 in in IN cord-276598-tm0yj2sn 356 21 52 52 CD cord-276598-tm0yj2sn 356 22 - - SYM cord-276598-tm0yj2sn 356 23 99 99 CD cord-276598-tm0yj2sn 356 24 % % NN cord-276598-tm0yj2sn 356 25 yield yield NN cord-276598-tm0yj2sn 356 26 . . . cord-276598-tm0yj2sn 357 1 Through through IN cord-276598-tm0yj2sn 357 2 the the DT cord-276598-tm0yj2sn 357 3 reagent reagent NN cord-276598-tm0yj2sn 357 4 screening screening NN cord-276598-tm0yj2sn 357 5 , , , cord-276598-tm0yj2sn 357 6 Mizuno Mizuno NNP cord-276598-tm0yj2sn 357 7 et et NNP cord-276598-tm0yj2sn 357 8 al al NNP cord-276598-tm0yj2sn 357 9 . . . cord-276598-tm0yj2sn 358 1 [ [ -LRB- cord-276598-tm0yj2sn 358 2 107 107 CD cord-276598-tm0yj2sn 358 3 ] ] -RRB- cord-276598-tm0yj2sn 358 4 found find VBD cord-276598-tm0yj2sn 358 5 that that IN cord-276598-tm0yj2sn 358 6 Cu(OTf cu(otf NN cord-276598-tm0yj2sn 358 7 ) ) -RRB- cord-276598-tm0yj2sn 358 8 2 2 CD cord-276598-tm0yj2sn 358 9 gave give VBD cord-276598-tm0yj2sn 358 10 similar similar JJ cord-276598-tm0yj2sn 358 11 cross cross JJ cord-276598-tm0yj2sn 358 12 - - JJ cord-276598-tm0yj2sn 358 13 coupling coupling JJ cord-276598-tm0yj2sn 358 14 results result NNS cord-276598-tm0yj2sn 358 15 as as IN cord-276598-tm0yj2sn 358 16 Cu(OAc Cu(OAc NNS cord-276598-tm0yj2sn 358 17 ) ) -RRB- cord-276598-tm0yj2sn 358 18 2 2 CD cord-276598-tm0yj2sn 358 19 , , , cord-276598-tm0yj2sn 358 20 while while IN cord-276598-tm0yj2sn 358 21 other other JJ cord-276598-tm0yj2sn 358 22 Cu Cu NNP cord-276598-tm0yj2sn 358 23 catalysts catalyst NNS cord-276598-tm0yj2sn 358 24 such such JJ cord-276598-tm0yj2sn 358 25 as as IN cord-276598-tm0yj2sn 358 26 CuCl CuCl NNP cord-276598-tm0yj2sn 358 27 2 2 CD cord-276598-tm0yj2sn 358 28 and and CC cord-276598-tm0yj2sn 358 29 CuSO CuSO NNP cord-276598-tm0yj2sn 358 30 4 4 CD cord-276598-tm0yj2sn 358 31 and and CC cord-276598-tm0yj2sn 358 32 other other JJ cord-276598-tm0yj2sn 358 33 transition transition NN cord-276598-tm0yj2sn 358 34 metal metal NN cord-276598-tm0yj2sn 358 35 catalysts catalyst NNS cord-276598-tm0yj2sn 358 36 ( ( -LRB- cord-276598-tm0yj2sn 358 37 e.g. e.g. RB cord-276598-tm0yj2sn 358 38 , , , cord-276598-tm0yj2sn 358 39 Co(OAc Co(OAc NNS cord-276598-tm0yj2sn 358 40 ) ) -RRB- cord-276598-tm0yj2sn 358 41 2 2 CD cord-276598-tm0yj2sn 358 42 .4H .4h SYM cord-276598-tm0yj2sn 358 43 2 2 CD cord-276598-tm0yj2sn 358 44 O o NN cord-276598-tm0yj2sn 358 45 , , , cord-276598-tm0yj2sn 358 46 Fe(OAc Fe(OAc NNS cord-276598-tm0yj2sn 358 47 ) ) -RRB- cord-276598-tm0yj2sn 358 48 2 2 CD cord-276598-tm0yj2sn 358 49 ) ) -RRB- cord-276598-tm0yj2sn 358 50 were be VBD cord-276598-tm0yj2sn 358 51 not not RB cord-276598-tm0yj2sn 358 52 selective selective JJ cord-276598-tm0yj2sn 358 53 or or CC cord-276598-tm0yj2sn 358 54 completely completely RB cord-276598-tm0yj2sn 358 55 ineffective ineffective JJ cord-276598-tm0yj2sn 358 56 . . . cord-276598-tm0yj2sn 359 1 Another another DT cord-276598-tm0yj2sn 359 2 copper copper NN cord-276598-tm0yj2sn 359 3 - - HYPH cord-276598-tm0yj2sn 359 4 catalyzed catalyze VBN cord-276598-tm0yj2sn 359 5 synthesis synthesis NN cord-276598-tm0yj2sn 359 6 of of IN cord-276598-tm0yj2sn 359 7 P p NN cord-276598-tm0yj2sn 359 8 - - HYPH cord-276598-tm0yj2sn 359 9 N N NNP cord-276598-tm0yj2sn 359 10 at at IN cord-276598-tm0yj2sn 359 11 20 20 CD cord-276598-tm0yj2sn 360 1 • • NNP cord-276598-tm0yj2sn 361 1 C C NNP cord-276598-tm0yj2sn 361 2 in in IN cord-276598-tm0yj2sn 361 3 the the DT cord-276598-tm0yj2sn 361 4 presence presence NN cord-276598-tm0yj2sn 361 5 of of IN cord-276598-tm0yj2sn 361 6 air air NN cord-276598-tm0yj2sn 361 7 , , , cord-276598-tm0yj2sn 361 8 reported report VBN cord-276598-tm0yj2sn 361 9 by by IN cord-276598-tm0yj2sn 361 10 Zhou Zhou NNP cord-276598-tm0yj2sn 361 11 et et NNP cord-276598-tm0yj2sn 361 12 al al NNP cord-276598-tm0yj2sn 361 13 . . . cord-276598-tm0yj2sn 362 1 , , , cord-276598-tm0yj2sn 362 2 involved involve VBN cord-276598-tm0yj2sn 362 3 reacting react VBG cord-276598-tm0yj2sn 362 4 ( ( -LRB- cord-276598-tm0yj2sn 362 5 RO RO NNP cord-276598-tm0yj2sn 362 6 ) ) -RRB- cord-276598-tm0yj2sn 362 7 2 2 CD cord-276598-tm0yj2sn 363 1 P(O)H p(o)h NN cord-276598-tm0yj2sn 364 1 ( ( -LRB- cord-276598-tm0yj2sn 364 2 R r NN cord-276598-tm0yj2sn 364 3 = = NFP cord-276598-tm0yj2sn 365 1 Me -PRON- PRP cord-276598-tm0yj2sn 365 2 , , , cord-276598-tm0yj2sn 365 3 Et Et NNP cord-276598-tm0yj2sn 365 4 , , , cord-276598-tm0yj2sn 365 5 i i NN cord-276598-tm0yj2sn 365 6 - - HYPH cord-276598-tm0yj2sn 365 7 Pr Pr NNP cord-276598-tm0yj2sn 365 8 , , , cord-276598-tm0yj2sn 365 9 Ph Ph NNP cord-276598-tm0yj2sn 365 10 ) ) -RRB- cord-276598-tm0yj2sn 365 11 with with IN cord-276598-tm0yj2sn 365 12 primary primary JJ cord-276598-tm0yj2sn 365 13 or or CC cord-276598-tm0yj2sn 365 14 secondary secondary JJ cord-276598-tm0yj2sn 365 15 amines amine NNS cord-276598-tm0yj2sn 365 16 ( ( -LRB- cord-276598-tm0yj2sn 365 17 butylamine butylamine NNP cord-276598-tm0yj2sn 365 18 , , , cord-276598-tm0yj2sn 365 19 dibutylamine dibutylamine NNP cord-276598-tm0yj2sn 365 20 , , , cord-276598-tm0yj2sn 365 21 hexylamine hexylamine NNP cord-276598-tm0yj2sn 365 22 , , , cord-276598-tm0yj2sn 365 23 cylohexylamine cylohexylamine NN cord-276598-tm0yj2sn 365 24 , , , cord-276598-tm0yj2sn 365 25 and and CC cord-276598-tm0yj2sn 365 26 methyl methyl NN cord-276598-tm0yj2sn 365 27 alaninate alaninate NN cord-276598-tm0yj2sn 365 28 ; ; : cord-276598-tm0yj2sn 365 29 Table table NN cord-276598-tm0yj2sn 365 30 1 1 CD cord-276598-tm0yj2sn 365 31 , , , cord-276598-tm0yj2sn 365 32 route route NN cord-276598-tm0yj2sn 365 33 f f NNP cord-276598-tm0yj2sn 365 34 ) ) -RRB- cord-276598-tm0yj2sn 365 35 [ [ -LRB- cord-276598-tm0yj2sn 365 36 108 108 CD cord-276598-tm0yj2sn 365 37 ] ] -RRB- cord-276598-tm0yj2sn 365 38 . . . cord-276598-tm0yj2sn 366 1 The the DT cord-276598-tm0yj2sn 366 2 crude crude NN cord-276598-tm0yj2sn 366 3 P p NN cord-276598-tm0yj2sn 366 4 - - HYPH cord-276598-tm0yj2sn 366 5 Ns Ns NNP cord-276598-tm0yj2sn 366 6 were be VBD cord-276598-tm0yj2sn 366 7 extracted extract VBN cord-276598-tm0yj2sn 366 8 and and CC cord-276598-tm0yj2sn 366 9 then then RB cord-276598-tm0yj2sn 366 10 concentrated concentrate VBN cord-276598-tm0yj2sn 366 11 under under IN cord-276598-tm0yj2sn 366 12 vacuum vacuum NN cord-276598-tm0yj2sn 366 13 to to TO cord-276598-tm0yj2sn 366 14 obtain obtain VB cord-276598-tm0yj2sn 366 15 pure pure JJ cord-276598-tm0yj2sn 366 16 products product NNS cord-276598-tm0yj2sn 366 17 with with IN cord-276598-tm0yj2sn 366 18 excellent excellent JJ cord-276598-tm0yj2sn 366 19 isolated isolated JJ cord-276598-tm0yj2sn 366 20 yields yield NNS cord-276598-tm0yj2sn 366 21 ( ( -LRB- cord-276598-tm0yj2sn 366 22 86 86 CD cord-276598-tm0yj2sn 366 23 - - SYM cord-276598-tm0yj2sn 366 24 96 96 CD cord-276598-tm0yj2sn 366 25 % % NN cord-276598-tm0yj2sn 366 26 ) ) -RRB- cord-276598-tm0yj2sn 366 27 . . . cord-276598-tm0yj2sn 367 1 Similar similar JJ cord-276598-tm0yj2sn 367 2 to to IN cord-276598-tm0yj2sn 367 3 other other JJ cord-276598-tm0yj2sn 367 4 copper copper NN cord-276598-tm0yj2sn 367 5 - - HYPH cord-276598-tm0yj2sn 367 6 catalyzed catalyze VBN cord-276598-tm0yj2sn 367 7 P P NNP cord-276598-tm0yj2sn 367 8 - - HYPH cord-276598-tm0yj2sn 367 9 N n CD cord-276598-tm0yj2sn 367 10 synthesis synthesis NN cord-276598-tm0yj2sn 367 11 , , , cord-276598-tm0yj2sn 367 12 the the DT cord-276598-tm0yj2sn 367 13 authors author NNS cord-276598-tm0yj2sn 367 14 reported report VBD cord-276598-tm0yj2sn 367 15 a a DT cord-276598-tm0yj2sn 367 16 low low JJ cord-276598-tm0yj2sn 367 17 yield yield NN cord-276598-tm0yj2sn 367 18 ( ( -LRB- cord-276598-tm0yj2sn 367 19 21 21 CD cord-276598-tm0yj2sn 367 20 % % NN cord-276598-tm0yj2sn 367 21 ) ) -RRB- cord-276598-tm0yj2sn 367 22 when when WRB cord-276598-tm0yj2sn 367 23 dibutylamine dibutylamine NNP cord-276598-tm0yj2sn 367 24 and and CC cord-276598-tm0yj2sn 367 25 diisopropyl diisopropyl NNP cord-276598-tm0yj2sn 367 26 H H NNP cord-276598-tm0yj2sn 367 27 - - HYPH cord-276598-tm0yj2sn 367 28 P P NNP cord-276598-tm0yj2sn 367 29 were be VBD cord-276598-tm0yj2sn 367 30 used use VBN cord-276598-tm0yj2sn 367 31 as as IN cord-276598-tm0yj2sn 367 32 substrates substrate NNS cord-276598-tm0yj2sn 367 33 , , , cord-276598-tm0yj2sn 367 34 which which WDT cord-276598-tm0yj2sn 367 35 could could MD cord-276598-tm0yj2sn 367 36 be be VB cord-276598-tm0yj2sn 367 37 attributed attribute VBN cord-276598-tm0yj2sn 367 38 to to IN cord-276598-tm0yj2sn 367 39 steric steric JJ cord-276598-tm0yj2sn 367 40 effects effect NNS cord-276598-tm0yj2sn 367 41 . . . cord-276598-tm0yj2sn 368 1 In in IN cord-276598-tm0yj2sn 368 2 addition addition NN cord-276598-tm0yj2sn 368 3 , , , cord-276598-tm0yj2sn 368 4 the the DT cord-276598-tm0yj2sn 368 5 method method NN cord-276598-tm0yj2sn 368 6 was be VBD cord-276598-tm0yj2sn 368 7 not not RB cord-276598-tm0yj2sn 368 8 effective effective JJ cord-276598-tm0yj2sn 368 9 when when WRB cord-276598-tm0yj2sn 368 10 diphenylphosphine diphenylphosphine JJ cord-276598-tm0yj2sn 368 11 oxide oxide NN cord-276598-tm0yj2sn 368 12 ( ( -LRB- cord-276598-tm0yj2sn 368 13 dPPO dPPO NNP cord-276598-tm0yj2sn 368 14 ) ) -RRB- cord-276598-tm0yj2sn 368 15 was be VBD cord-276598-tm0yj2sn 368 16 reacted react VBN cord-276598-tm0yj2sn 368 17 with with IN cord-276598-tm0yj2sn 368 18 butylamine butylamine NN cord-276598-tm0yj2sn 368 19 ( ( -LRB- cord-276598-tm0yj2sn 368 20 13 13 CD cord-276598-tm0yj2sn 368 21 % % NN cord-276598-tm0yj2sn 368 22 isolated isolated JJ cord-276598-tm0yj2sn 368 23 yield yield NN cord-276598-tm0yj2sn 368 24 ) ) -RRB- cord-276598-tm0yj2sn 368 25 due due IN cord-276598-tm0yj2sn 368 26 to to IN cord-276598-tm0yj2sn 368 27 oxidative oxidative JJ cord-276598-tm0yj2sn 368 28 conversion conversion NN cord-276598-tm0yj2sn 368 29 to to IN cord-276598-tm0yj2sn 368 30 phosphonic phosphonic NNP cord-276598-tm0yj2sn 368 31 acid acid NNP cord-276598-tm0yj2sn 368 32 ( ( -LRB- cord-276598-tm0yj2sn 368 33 PP PP NNP cord-276598-tm0yj2sn 368 34 - - HYPH cord-276598-tm0yj2sn 368 35 A A NNP cord-276598-tm0yj2sn 368 36 ) ) -RRB- cord-276598-tm0yj2sn 368 37 . . . cord-276598-tm0yj2sn 369 1 Using use VBG cord-276598-tm0yj2sn 369 2 this this DT cord-276598-tm0yj2sn 369 3 aerobic aerobic JJ cord-276598-tm0yj2sn 369 4 copper copper NN cord-276598-tm0yj2sn 369 5 - - HYPH cord-276598-tm0yj2sn 369 6 catalyzed catalyze VBN cord-276598-tm0yj2sn 369 7 dehydrocoupling dehydrocoupling NN cord-276598-tm0yj2sn 369 8 method method NN cord-276598-tm0yj2sn 369 9 , , , cord-276598-tm0yj2sn 369 10 Zhou Zhou NNP cord-276598-tm0yj2sn 369 11 et et NNP cord-276598-tm0yj2sn 369 12 al al NNP cord-276598-tm0yj2sn 369 13 . . NNP cord-276598-tm0yj2sn 369 14 synthesized synthesize VBD cord-276598-tm0yj2sn 369 15 a a DT cord-276598-tm0yj2sn 369 16 phosphoryl phosphoryl NN cord-276598-tm0yj2sn 369 17 amino amino NN cord-276598-tm0yj2sn 369 18 compound compound NN cord-276598-tm0yj2sn 369 19 ( ( -LRB- cord-276598-tm0yj2sn 369 20 16 16 CD cord-276598-tm0yj2sn 369 21 ) ) -RRB- cord-276598-tm0yj2sn 369 22 ( ( -LRB- cord-276598-tm0yj2sn 369 23 Figure figure NN cord-276598-tm0yj2sn 369 24 7 7 CD cord-276598-tm0yj2sn 369 25 ) ) -RRB- cord-276598-tm0yj2sn 369 26 . . . cord-276598-tm0yj2sn 370 1 ( ( -LRB- cord-276598-tm0yj2sn 370 2 butylamine butylamine NNP cord-276598-tm0yj2sn 370 3 , , , cord-276598-tm0yj2sn 370 4 dibutylamine dibutylamine NNP cord-276598-tm0yj2sn 370 5 , , , cord-276598-tm0yj2sn 370 6 hexylamine hexylamine NNP cord-276598-tm0yj2sn 370 7 , , , cord-276598-tm0yj2sn 370 8 cylohexylamine cylohexylamine NN cord-276598-tm0yj2sn 370 9 , , , cord-276598-tm0yj2sn 370 10 and and CC cord-276598-tm0yj2sn 370 11 methyl methyl NN cord-276598-tm0yj2sn 370 12 alaninate alaninate NN cord-276598-tm0yj2sn 370 13 ; ; : cord-276598-tm0yj2sn 370 14 Table table NN cord-276598-tm0yj2sn 370 15 1 1 CD cord-276598-tm0yj2sn 370 16 , , , cord-276598-tm0yj2sn 370 17 route route NN cord-276598-tm0yj2sn 370 18 f f NNP cord-276598-tm0yj2sn 370 19 ) ) -RRB- cord-276598-tm0yj2sn 370 20 [ [ -LRB- cord-276598-tm0yj2sn 370 21 108 108 CD cord-276598-tm0yj2sn 370 22 ] ] -RRB- cord-276598-tm0yj2sn 370 23 . . . cord-276598-tm0yj2sn 371 1 The the DT cord-276598-tm0yj2sn 371 2 crude crude NN cord-276598-tm0yj2sn 371 3 P p NN cord-276598-tm0yj2sn 371 4 - - HYPH cord-276598-tm0yj2sn 371 5 Ns Ns NNP cord-276598-tm0yj2sn 371 6 were be VBD cord-276598-tm0yj2sn 371 7 extracted extract VBN cord-276598-tm0yj2sn 371 8 and and CC cord-276598-tm0yj2sn 371 9 then then RB cord-276598-tm0yj2sn 371 10 concentrated concentrate VBN cord-276598-tm0yj2sn 371 11 under under IN cord-276598-tm0yj2sn 371 12 vacuum vacuum NN cord-276598-tm0yj2sn 371 13 to to TO cord-276598-tm0yj2sn 371 14 obtain obtain VB cord-276598-tm0yj2sn 371 15 pure pure JJ cord-276598-tm0yj2sn 371 16 products product NNS cord-276598-tm0yj2sn 371 17 with with IN cord-276598-tm0yj2sn 371 18 excellent excellent JJ cord-276598-tm0yj2sn 371 19 isolated isolated JJ cord-276598-tm0yj2sn 371 20 yields yield NNS cord-276598-tm0yj2sn 371 21 ( ( -LRB- cord-276598-tm0yj2sn 371 22 86 86 CD cord-276598-tm0yj2sn 371 23 - - SYM cord-276598-tm0yj2sn 371 24 96 96 CD cord-276598-tm0yj2sn 371 25 % % NN cord-276598-tm0yj2sn 371 26 ) ) -RRB- cord-276598-tm0yj2sn 371 27 . . . cord-276598-tm0yj2sn 372 1 Similar similar JJ cord-276598-tm0yj2sn 372 2 to to IN cord-276598-tm0yj2sn 372 3 other other JJ cord-276598-tm0yj2sn 372 4 copper copper NN cord-276598-tm0yj2sn 372 5 - - HYPH cord-276598-tm0yj2sn 372 6 catalyzed catalyze VBN cord-276598-tm0yj2sn 372 7 P P NNP cord-276598-tm0yj2sn 372 8 - - HYPH cord-276598-tm0yj2sn 372 9 N n CD cord-276598-tm0yj2sn 372 10 synthesis synthesis NN cord-276598-tm0yj2sn 372 11 , , , cord-276598-tm0yj2sn 372 12 the the DT cord-276598-tm0yj2sn 372 13 authors author NNS cord-276598-tm0yj2sn 372 14 reported report VBD cord-276598-tm0yj2sn 372 15 a a DT cord-276598-tm0yj2sn 372 16 low low JJ cord-276598-tm0yj2sn 372 17 yield yield NN cord-276598-tm0yj2sn 372 18 ( ( -LRB- cord-276598-tm0yj2sn 372 19 21 21 CD cord-276598-tm0yj2sn 372 20 % % NN cord-276598-tm0yj2sn 372 21 ) ) -RRB- cord-276598-tm0yj2sn 372 22 when when WRB cord-276598-tm0yj2sn 372 23 dibutylamine dibutylamine NNP cord-276598-tm0yj2sn 372 24 and and CC cord-276598-tm0yj2sn 372 25 diisopropyl diisopropyl NNP cord-276598-tm0yj2sn 372 26 H H NNP cord-276598-tm0yj2sn 372 27 - - HYPH cord-276598-tm0yj2sn 372 28 P P NNP cord-276598-tm0yj2sn 372 29 were be VBD cord-276598-tm0yj2sn 372 30 used use VBN cord-276598-tm0yj2sn 372 31 as as IN cord-276598-tm0yj2sn 372 32 substrates substrate NNS cord-276598-tm0yj2sn 372 33 , , , cord-276598-tm0yj2sn 372 34 which which WDT cord-276598-tm0yj2sn 372 35 could could MD cord-276598-tm0yj2sn 372 36 be be VB cord-276598-tm0yj2sn 372 37 attributed attribute VBN cord-276598-tm0yj2sn 372 38 to to IN cord-276598-tm0yj2sn 372 39 steric steric JJ cord-276598-tm0yj2sn 372 40 effects effect NNS cord-276598-tm0yj2sn 372 41 . . . cord-276598-tm0yj2sn 373 1 In in IN cord-276598-tm0yj2sn 373 2 addition addition NN cord-276598-tm0yj2sn 373 3 , , , cord-276598-tm0yj2sn 373 4 the the DT cord-276598-tm0yj2sn 373 5 method method NN cord-276598-tm0yj2sn 373 6 was be VBD cord-276598-tm0yj2sn 373 7 not not RB cord-276598-tm0yj2sn 373 8 effective effective JJ cord-276598-tm0yj2sn 373 9 when when WRB cord-276598-tm0yj2sn 373 10 diphenylphosphine diphenylphosphine JJ cord-276598-tm0yj2sn 373 11 oxide oxide NN cord-276598-tm0yj2sn 373 12 ( ( -LRB- cord-276598-tm0yj2sn 373 13 dPPO dPPO NNP cord-276598-tm0yj2sn 373 14 ) ) -RRB- cord-276598-tm0yj2sn 373 15 was be VBD cord-276598-tm0yj2sn 373 16 reacted react VBN cord-276598-tm0yj2sn 373 17 with with IN cord-276598-tm0yj2sn 373 18 butylamine butylamine NN cord-276598-tm0yj2sn 373 19 ( ( -LRB- cord-276598-tm0yj2sn 373 20 13 13 CD cord-276598-tm0yj2sn 373 21 % % NN cord-276598-tm0yj2sn 373 22 isolated isolated JJ cord-276598-tm0yj2sn 373 23 yield yield NN cord-276598-tm0yj2sn 373 24 ) ) -RRB- cord-276598-tm0yj2sn 373 25 due due IN cord-276598-tm0yj2sn 373 26 to to IN cord-276598-tm0yj2sn 373 27 oxidative oxidative JJ cord-276598-tm0yj2sn 373 28 conversion conversion NN cord-276598-tm0yj2sn 373 29 to to IN cord-276598-tm0yj2sn 373 30 phosphonic phosphonic NNP cord-276598-tm0yj2sn 373 31 acid acid NNP cord-276598-tm0yj2sn 373 32 ( ( -LRB- cord-276598-tm0yj2sn 373 33 PP PP NNP cord-276598-tm0yj2sn 373 34 - - HYPH cord-276598-tm0yj2sn 373 35 A A NNP cord-276598-tm0yj2sn 373 36 ) ) -RRB- cord-276598-tm0yj2sn 373 37 . . . cord-276598-tm0yj2sn 374 1 Using use VBG cord-276598-tm0yj2sn 374 2 this this DT cord-276598-tm0yj2sn 374 3 aerobic aerobic JJ cord-276598-tm0yj2sn 374 4 copper copper NN cord-276598-tm0yj2sn 374 5 - - HYPH cord-276598-tm0yj2sn 374 6 catalyzed catalyze VBN cord-276598-tm0yj2sn 374 7 dehydrocoupling dehydrocoupling NN cord-276598-tm0yj2sn 374 8 method method NN cord-276598-tm0yj2sn 374 9 , , , cord-276598-tm0yj2sn 374 10 Zhou Zhou NNP cord-276598-tm0yj2sn 374 11 et et NNP cord-276598-tm0yj2sn 374 12 al al NNP cord-276598-tm0yj2sn 374 13 . . NNP cord-276598-tm0yj2sn 374 14 synthesized synthesize VBD cord-276598-tm0yj2sn 374 15 a a DT cord-276598-tm0yj2sn 374 16 phosphoryl phosphoryl NN cord-276598-tm0yj2sn 374 17 amino amino NN cord-276598-tm0yj2sn 374 18 compound compound NN cord-276598-tm0yj2sn 374 19 ( ( -LRB- cord-276598-tm0yj2sn 374 20 16 16 CD cord-276598-tm0yj2sn 374 21 ) ) -RRB- cord-276598-tm0yj2sn 374 22 ( ( -LRB- cord-276598-tm0yj2sn 374 23 Figure figure NN cord-276598-tm0yj2sn 374 24 7 7 CD cord-276598-tm0yj2sn 374 25 ) ) -RRB- cord-276598-tm0yj2sn 374 26 . . . cord-276598-tm0yj2sn 375 1 Phenylboronic Phenylboronic NNP cord-276598-tm0yj2sn 375 2 acid acid NN cord-276598-tm0yj2sn 375 3 or or CC cord-276598-tm0yj2sn 375 4 ester ester NN cord-276598-tm0yj2sn 375 5 - - HYPH cord-276598-tm0yj2sn 375 6 based base VBN cord-276598-tm0yj2sn 375 7 substrates substrate NNS cord-276598-tm0yj2sn 375 8 were be VBD cord-276598-tm0yj2sn 375 9 converted convert VBN cord-276598-tm0yj2sn 375 10 in in IN cord-276598-tm0yj2sn 375 11 situ situ NN cord-276598-tm0yj2sn 375 12 to to IN cord-276598-tm0yj2sn 375 13 an an DT cord-276598-tm0yj2sn 375 14 organic organic JJ cord-276598-tm0yj2sn 375 15 azide azide NN cord-276598-tm0yj2sn 375 16 using use VBG cord-276598-tm0yj2sn 375 17 a a DT cord-276598-tm0yj2sn 375 18 Cu Cu NNP cord-276598-tm0yj2sn 375 19 - - HYPH cord-276598-tm0yj2sn 375 20 based base VBN cord-276598-tm0yj2sn 375 21 catalyst catalyst NN cord-276598-tm0yj2sn 375 22 and and CC cord-276598-tm0yj2sn 375 23 subsequently subsequently RB cord-276598-tm0yj2sn 375 24 used use VBN cord-276598-tm0yj2sn 375 25 for for IN cord-276598-tm0yj2sn 375 26 the the DT cord-276598-tm0yj2sn 375 27 synthesis synthesis NN cord-276598-tm0yj2sn 375 28 of of IN cord-276598-tm0yj2sn 375 29 P P NNP cord-276598-tm0yj2sn 375 30 - - HYPH cord-276598-tm0yj2sn 375 31 Ns Ns NNP cord-276598-tm0yj2sn 375 32 via via IN cord-276598-tm0yj2sn 375 33 a a DT cord-276598-tm0yj2sn 375 34 coupling coupling NN cord-276598-tm0yj2sn 375 35 reaction reaction NN cord-276598-tm0yj2sn 375 36 , , , cord-276598-tm0yj2sn 375 37 according accord VBG cord-276598-tm0yj2sn 375 38 to to IN cord-276598-tm0yj2sn 375 39 Dangroo Dangroo NNP cord-276598-tm0yj2sn 375 40 et et FW cord-276598-tm0yj2sn 375 41 al al NNP cord-276598-tm0yj2sn 375 42 . . . cord-276598-tm0yj2sn 376 1 ( ( -LRB- cord-276598-tm0yj2sn 376 2 Table table NN cord-276598-tm0yj2sn 376 3 1 1 CD cord-276598-tm0yj2sn 376 4 , , , cord-276598-tm0yj2sn 376 5 route route NN cord-276598-tm0yj2sn 376 6 g g NN cord-276598-tm0yj2sn 376 7 ) ) -RRB- cord-276598-tm0yj2sn 377 1 [ [ -LRB- cord-276598-tm0yj2sn 377 2 109 109 CD cord-276598-tm0yj2sn 377 3 ] ] -RRB- cord-276598-tm0yj2sn 377 4 . . . cord-276598-tm0yj2sn 378 1 Triethyl Triethyl NNP cord-276598-tm0yj2sn 378 2 and and CC cord-276598-tm0yj2sn 378 3 trimethyl trimethyl NN cord-276598-tm0yj2sn 378 4 phosphate phosphate NN cord-276598-tm0yj2sn 378 5 were be VBD cord-276598-tm0yj2sn 378 6 used use VBN cord-276598-tm0yj2sn 378 7 as as IN cord-276598-tm0yj2sn 378 8 the the DT cord-276598-tm0yj2sn 378 9 P p NN cord-276598-tm0yj2sn 378 10 - - HYPH cord-276598-tm0yj2sn 378 11 sources source NNS cord-276598-tm0yj2sn 378 12 while while IN cord-276598-tm0yj2sn 378 13 phenylboronic phenylboronic JJ cord-276598-tm0yj2sn 378 14 acids acid NNS cord-276598-tm0yj2sn 378 15 or or CC cord-276598-tm0yj2sn 378 16 esters ester NNS cord-276598-tm0yj2sn 378 17 with with IN cord-276598-tm0yj2sn 378 18 substituents substituent NNS cord-276598-tm0yj2sn 378 19 such such JJ cord-276598-tm0yj2sn 378 20 as as IN cord-276598-tm0yj2sn 378 21 CN CN NNP cord-276598-tm0yj2sn 378 22 , , , cord-276598-tm0yj2sn 378 23 NO2 NO2 NNP cord-276598-tm0yj2sn 378 24 , , , cord-276598-tm0yj2sn 378 25 OH oh UH cord-276598-tm0yj2sn 378 26 , , , cord-276598-tm0yj2sn 378 27 OMe OMe NNS cord-276598-tm0yj2sn 378 28 and and CC cord-276598-tm0yj2sn 378 29 halides halide NNS cord-276598-tm0yj2sn 378 30 were be VBD cord-276598-tm0yj2sn 378 31 used use VBN cord-276598-tm0yj2sn 378 32 for for IN cord-276598-tm0yj2sn 378 33 azide azide NN cord-276598-tm0yj2sn 378 34 conversion conversion NN cord-276598-tm0yj2sn 378 35 . . . cord-276598-tm0yj2sn 379 1 The the DT cord-276598-tm0yj2sn 379 2 reaction reaction NN cord-276598-tm0yj2sn 379 3 was be VBD cord-276598-tm0yj2sn 379 4 very very RB cord-276598-tm0yj2sn 379 5 tolerant tolerant JJ cord-276598-tm0yj2sn 379 6 to to IN cord-276598-tm0yj2sn 379 7 compounds compound NNS cord-276598-tm0yj2sn 379 8 with with IN cord-276598-tm0yj2sn 379 9 unsaturated unsaturated JJ cord-276598-tm0yj2sn 379 10 boron boron NN cord-276598-tm0yj2sn 379 11 - - HYPH cord-276598-tm0yj2sn 379 12 carbon carbon NN cord-276598-tm0yj2sn 379 13 bonds bond NNS cord-276598-tm0yj2sn 379 14 giving give VBG cord-276598-tm0yj2sn 379 15 isolated isolate VBN cord-276598-tm0yj2sn 379 16 yields yield NNS cord-276598-tm0yj2sn 379 17 of of IN cord-276598-tm0yj2sn 379 18 67 67 CD cord-276598-tm0yj2sn 379 19 - - SYM cord-276598-tm0yj2sn 379 20 93 93 CD cord-276598-tm0yj2sn 379 21 % % NN cord-276598-tm0yj2sn 379 22 . . . cord-276598-tm0yj2sn 380 1 However however RB cord-276598-tm0yj2sn 380 2 , , , cord-276598-tm0yj2sn 380 3 this this DT cord-276598-tm0yj2sn 380 4 reaction reaction NN cord-276598-tm0yj2sn 380 5 is be VBZ cord-276598-tm0yj2sn 380 6 not not RB cord-276598-tm0yj2sn 380 7 effective effective JJ cord-276598-tm0yj2sn 380 8 for for IN cord-276598-tm0yj2sn 380 9 compounds compound NNS cord-276598-tm0yj2sn 380 10 containing contain VBG cord-276598-tm0yj2sn 380 11 saturated saturate VBN cord-276598-tm0yj2sn 380 12 boron boron NN cord-276598-tm0yj2sn 380 13 - - HYPH cord-276598-tm0yj2sn 380 14 carbon carbon NN cord-276598-tm0yj2sn 380 15 bonds bond NNS cord-276598-tm0yj2sn 380 16 such such JJ cord-276598-tm0yj2sn 380 17 as as IN cord-276598-tm0yj2sn 380 18 butyl butyl NN cord-276598-tm0yj2sn 380 19 boronic boronic NNP cord-276598-tm0yj2sn 380 20 acid acid NNP cord-276598-tm0yj2sn 380 21 or or CC cord-276598-tm0yj2sn 380 22 cyclopentyl cyclopentyl NNP cord-276598-tm0yj2sn 380 23 boronic boronic NNP cord-276598-tm0yj2sn 380 24 acid acid NNP cord-276598-tm0yj2sn 380 25 . . . cord-276598-tm0yj2sn 381 1 Transition transition NN cord-276598-tm0yj2sn 381 2 metal metal NN cord-276598-tm0yj2sn 381 3 - - HYPH cord-276598-tm0yj2sn 381 4 catalyzed catalyzed JJ cord-276598-tm0yj2sn 381 5 oxidative oxidative JJ cord-276598-tm0yj2sn 381 6 cross cross JJ cord-276598-tm0yj2sn 381 7 - - JJ cord-276598-tm0yj2sn 381 8 coupling coupling JJ cord-276598-tm0yj2sn 381 9 methods method NNS cord-276598-tm0yj2sn 381 10 for for IN cord-276598-tm0yj2sn 381 11 P p NN cord-276598-tm0yj2sn 381 12 - - HYPH cord-276598-tm0yj2sn 381 13 N n CD cord-276598-tm0yj2sn 381 14 synthesis synthesis NN cord-276598-tm0yj2sn 381 15 have have VBP cord-276598-tm0yj2sn 381 16 become become VBN cord-276598-tm0yj2sn 381 17 Phenylboronic Phenylboronic NNP cord-276598-tm0yj2sn 381 18 acid acid NN cord-276598-tm0yj2sn 381 19 or or CC cord-276598-tm0yj2sn 381 20 ester ester NN cord-276598-tm0yj2sn 381 21 - - HYPH cord-276598-tm0yj2sn 381 22 based base VBN cord-276598-tm0yj2sn 381 23 substrates substrate NNS cord-276598-tm0yj2sn 381 24 were be VBD cord-276598-tm0yj2sn 381 25 converted convert VBN cord-276598-tm0yj2sn 381 26 in in IN cord-276598-tm0yj2sn 381 27 situ situ NN cord-276598-tm0yj2sn 381 28 to to IN cord-276598-tm0yj2sn 381 29 an an DT cord-276598-tm0yj2sn 381 30 organic organic JJ cord-276598-tm0yj2sn 381 31 azide azide NN cord-276598-tm0yj2sn 381 32 using use VBG cord-276598-tm0yj2sn 381 33 a a DT cord-276598-tm0yj2sn 381 34 Cu Cu NNP cord-276598-tm0yj2sn 381 35 - - HYPH cord-276598-tm0yj2sn 381 36 based base VBN cord-276598-tm0yj2sn 381 37 catalyst catalyst NN cord-276598-tm0yj2sn 381 38 and and CC cord-276598-tm0yj2sn 381 39 subsequently subsequently RB cord-276598-tm0yj2sn 381 40 used use VBN cord-276598-tm0yj2sn 381 41 for for IN cord-276598-tm0yj2sn 381 42 the the DT cord-276598-tm0yj2sn 381 43 synthesis synthesis NN cord-276598-tm0yj2sn 381 44 of of IN cord-276598-tm0yj2sn 381 45 P P NNP cord-276598-tm0yj2sn 381 46 - - HYPH cord-276598-tm0yj2sn 381 47 Ns Ns NNP cord-276598-tm0yj2sn 381 48 via via IN cord-276598-tm0yj2sn 381 49 a a DT cord-276598-tm0yj2sn 381 50 coupling coupling NN cord-276598-tm0yj2sn 381 51 reaction reaction NN cord-276598-tm0yj2sn 381 52 , , , cord-276598-tm0yj2sn 381 53 according accord VBG cord-276598-tm0yj2sn 381 54 to to IN cord-276598-tm0yj2sn 381 55 Dangroo Dangroo NNP cord-276598-tm0yj2sn 381 56 et et FW cord-276598-tm0yj2sn 381 57 al al NNP cord-276598-tm0yj2sn 381 58 . . . cord-276598-tm0yj2sn 382 1 ( ( -LRB- cord-276598-tm0yj2sn 382 2 Table table NN cord-276598-tm0yj2sn 382 3 1 1 CD cord-276598-tm0yj2sn 382 4 , , , cord-276598-tm0yj2sn 382 5 route route NN cord-276598-tm0yj2sn 382 6 g g NN cord-276598-tm0yj2sn 382 7 ) ) -RRB- cord-276598-tm0yj2sn 383 1 [ [ -LRB- cord-276598-tm0yj2sn 383 2 109 109 CD cord-276598-tm0yj2sn 383 3 ] ] -RRB- cord-276598-tm0yj2sn 383 4 . . . cord-276598-tm0yj2sn 384 1 Triethyl Triethyl NNP cord-276598-tm0yj2sn 384 2 and and CC cord-276598-tm0yj2sn 384 3 trimethyl trimethyl NN cord-276598-tm0yj2sn 384 4 phosphate phosphate NN cord-276598-tm0yj2sn 384 5 were be VBD cord-276598-tm0yj2sn 384 6 used use VBN cord-276598-tm0yj2sn 384 7 as as IN cord-276598-tm0yj2sn 384 8 the the DT cord-276598-tm0yj2sn 384 9 P p NN cord-276598-tm0yj2sn 384 10 - - HYPH cord-276598-tm0yj2sn 384 11 sources source NNS cord-276598-tm0yj2sn 384 12 while while IN cord-276598-tm0yj2sn 384 13 phenylboronic phenylboronic JJ cord-276598-tm0yj2sn 384 14 acids acid NNS cord-276598-tm0yj2sn 384 15 or or CC cord-276598-tm0yj2sn 384 16 esters ester NNS cord-276598-tm0yj2sn 384 17 with with IN cord-276598-tm0yj2sn 384 18 substituents substituent NNS cord-276598-tm0yj2sn 384 19 such such JJ cord-276598-tm0yj2sn 384 20 as as IN cord-276598-tm0yj2sn 384 21 CN CN NNP cord-276598-tm0yj2sn 384 22 , , , cord-276598-tm0yj2sn 384 23 NO no DT cord-276598-tm0yj2sn 384 24 2 2 CD cord-276598-tm0yj2sn 384 25 , , , cord-276598-tm0yj2sn 384 26 OH oh UH cord-276598-tm0yj2sn 384 27 , , , cord-276598-tm0yj2sn 384 28 OMe OMe NNS cord-276598-tm0yj2sn 384 29 and and CC cord-276598-tm0yj2sn 384 30 halides halide NNS cord-276598-tm0yj2sn 384 31 were be VBD cord-276598-tm0yj2sn 384 32 used use VBN cord-276598-tm0yj2sn 384 33 for for IN cord-276598-tm0yj2sn 384 34 azide azide NN cord-276598-tm0yj2sn 384 35 conversion conversion NN cord-276598-tm0yj2sn 384 36 . . . cord-276598-tm0yj2sn 385 1 The the DT cord-276598-tm0yj2sn 385 2 reaction reaction NN cord-276598-tm0yj2sn 385 3 was be VBD cord-276598-tm0yj2sn 385 4 very very RB cord-276598-tm0yj2sn 385 5 tolerant tolerant JJ cord-276598-tm0yj2sn 385 6 to to IN cord-276598-tm0yj2sn 385 7 compounds compound NNS cord-276598-tm0yj2sn 385 8 with with IN cord-276598-tm0yj2sn 385 9 unsaturated unsaturated JJ cord-276598-tm0yj2sn 385 10 boron boron NN cord-276598-tm0yj2sn 385 11 - - HYPH cord-276598-tm0yj2sn 385 12 carbon carbon NN cord-276598-tm0yj2sn 385 13 bonds bond NNS cord-276598-tm0yj2sn 385 14 giving give VBG cord-276598-tm0yj2sn 385 15 isolated isolate VBN cord-276598-tm0yj2sn 385 16 yields yield NNS cord-276598-tm0yj2sn 385 17 of of IN cord-276598-tm0yj2sn 385 18 67 67 CD cord-276598-tm0yj2sn 385 19 - - SYM cord-276598-tm0yj2sn 385 20 93 93 CD cord-276598-tm0yj2sn 385 21 % % NN cord-276598-tm0yj2sn 385 22 . . . cord-276598-tm0yj2sn 386 1 However however RB cord-276598-tm0yj2sn 386 2 , , , cord-276598-tm0yj2sn 386 3 this this DT cord-276598-tm0yj2sn 386 4 reaction reaction NN cord-276598-tm0yj2sn 386 5 is be VBZ cord-276598-tm0yj2sn 386 6 not not RB cord-276598-tm0yj2sn 386 7 effective effective JJ cord-276598-tm0yj2sn 386 8 for for IN cord-276598-tm0yj2sn 386 9 compounds compound NNS cord-276598-tm0yj2sn 386 10 containing contain VBG cord-276598-tm0yj2sn 386 11 saturated saturate VBN cord-276598-tm0yj2sn 386 12 boron boron NN cord-276598-tm0yj2sn 386 13 - - HYPH cord-276598-tm0yj2sn 386 14 carbon carbon NN cord-276598-tm0yj2sn 386 15 bonds bond NNS cord-276598-tm0yj2sn 386 16 such such JJ cord-276598-tm0yj2sn 386 17 as as IN cord-276598-tm0yj2sn 386 18 butyl butyl NN cord-276598-tm0yj2sn 386 19 boronic boronic NNP cord-276598-tm0yj2sn 386 20 acid acid NNP cord-276598-tm0yj2sn 386 21 or or CC cord-276598-tm0yj2sn 386 22 cyclopentyl cyclopentyl NNP cord-276598-tm0yj2sn 386 23 boronic boronic NNP cord-276598-tm0yj2sn 386 24 acid acid NNP cord-276598-tm0yj2sn 386 25 . . . cord-276598-tm0yj2sn 387 1 Transition transition NN cord-276598-tm0yj2sn 387 2 metal metal NN cord-276598-tm0yj2sn 387 3 - - HYPH cord-276598-tm0yj2sn 387 4 catalyzed catalyzed JJ cord-276598-tm0yj2sn 387 5 oxidative oxidative JJ cord-276598-tm0yj2sn 387 6 cross cross JJ cord-276598-tm0yj2sn 387 7 - - JJ cord-276598-tm0yj2sn 387 8 coupling coupling JJ cord-276598-tm0yj2sn 387 9 methods method NNS cord-276598-tm0yj2sn 387 10 for for IN cord-276598-tm0yj2sn 387 11 P p NN cord-276598-tm0yj2sn 387 12 - - HYPH cord-276598-tm0yj2sn 387 13 N n CD cord-276598-tm0yj2sn 387 14 synthesis synthesis NN cord-276598-tm0yj2sn 387 15 have have VBP cord-276598-tm0yj2sn 387 16 become become VBN cord-276598-tm0yj2sn 387 17 attractive attractive JJ cord-276598-tm0yj2sn 387 18 in in IN cord-276598-tm0yj2sn 387 19 recent recent JJ cord-276598-tm0yj2sn 387 20 years year NNS cord-276598-tm0yj2sn 387 21 because because IN cord-276598-tm0yj2sn 387 22 of of IN cord-276598-tm0yj2sn 387 23 the the DT cord-276598-tm0yj2sn 387 24 advantages advantage NNS cord-276598-tm0yj2sn 387 25 of of IN cord-276598-tm0yj2sn 387 26 using use VBG cord-276598-tm0yj2sn 387 27 readily readily RB cord-276598-tm0yj2sn 387 28 available available JJ cord-276598-tm0yj2sn 387 29 inexpensive inexpensive JJ cord-276598-tm0yj2sn 387 30 catalysts catalyst NNS cord-276598-tm0yj2sn 387 31 , , , cord-276598-tm0yj2sn 387 32 for for IN cord-276598-tm0yj2sn 387 33 example example NN cord-276598-tm0yj2sn 387 34 CuX CuX NNP cord-276598-tm0yj2sn 387 35 n n NNP cord-276598-tm0yj2sn 388 1 ( ( -LRB- cord-276598-tm0yj2sn 388 2 X x NN cord-276598-tm0yj2sn 388 3 = = SYM cord-276598-tm0yj2sn 388 4 Cl Cl NNP cord-276598-tm0yj2sn 388 5 , , , cord-276598-tm0yj2sn 388 6 Br Br NNP cord-276598-tm0yj2sn 388 7 , , , cord-276598-tm0yj2sn 388 8 ( ( -LRB- cord-276598-tm0yj2sn 388 9 OAc OAc NNS cord-276598-tm0yj2sn 388 10 ) ) -RRB- cord-276598-tm0yj2sn 388 11 , , , cord-276598-tm0yj2sn 388 12 etc etc FW cord-276598-tm0yj2sn 388 13 . . . cord-276598-tm0yj2sn 389 1 , , , cord-276598-tm0yj2sn 389 2 n n NN cord-276598-tm0yj2sn 389 3 = = SYM cord-276598-tm0yj2sn 389 4 1 1 CD cord-276598-tm0yj2sn 389 5 , , , cord-276598-tm0yj2sn 389 6 2 2 CD cord-276598-tm0yj2sn 389 7 ) ) -RRB- cord-276598-tm0yj2sn 389 8 , , , cord-276598-tm0yj2sn 389 9 and and CC cord-276598-tm0yj2sn 389 10 air air NN cord-276598-tm0yj2sn 389 11 as as IN cord-276598-tm0yj2sn 389 12 an an DT cord-276598-tm0yj2sn 389 13 oxidant oxidant NN cord-276598-tm0yj2sn 389 14 . . . cord-276598-tm0yj2sn 390 1 In in IN cord-276598-tm0yj2sn 390 2 addition addition NN cord-276598-tm0yj2sn 390 3 , , , cord-276598-tm0yj2sn 390 4 this this DT cord-276598-tm0yj2sn 390 5 route route NN cord-276598-tm0yj2sn 390 6 uses use VBZ cord-276598-tm0yj2sn 390 7 environmentally environmentally RB cord-276598-tm0yj2sn 390 8 friendly friendly JJ cord-276598-tm0yj2sn 390 9 H h NN cord-276598-tm0yj2sn 390 10 - - HYPH cord-276598-tm0yj2sn 390 11 P p NN cord-276598-tm0yj2sn 390 12 ( ( -LRB- cord-276598-tm0yj2sn 390 13 RO RO NNP cord-276598-tm0yj2sn 390 14 ) ) -RRB- cord-276598-tm0yj2sn 390 15 2 2 CD cord-276598-tm0yj2sn 391 1 P(O)H p(o)h NN cord-276598-tm0yj2sn 392 1 ( ( -LRB- cord-276598-tm0yj2sn 392 2 R r NN cord-276598-tm0yj2sn 392 3 = = NN cord-276598-tm0yj2sn 392 4 alkyl alkyl NN cord-276598-tm0yj2sn 392 5 , , , cord-276598-tm0yj2sn 392 6 Ph Ph NNP cord-276598-tm0yj2sn 392 7 ) ) -RRB- cord-276598-tm0yj2sn 392 8 and and CC cord-276598-tm0yj2sn 392 9 amines amine NNS cord-276598-tm0yj2sn 392 10 as as IN cord-276598-tm0yj2sn 392 11 starting start VBG cord-276598-tm0yj2sn 392 12 materials material NNS cord-276598-tm0yj2sn 392 13 in in IN cord-276598-tm0yj2sn 392 14 a a DT cord-276598-tm0yj2sn 392 15 one one CD cord-276598-tm0yj2sn 392 16 - - HYPH cord-276598-tm0yj2sn 392 17 pot pot NN cord-276598-tm0yj2sn 392 18 single single JJ cord-276598-tm0yj2sn 392 19 - - HYPH cord-276598-tm0yj2sn 392 20 step step NN cord-276598-tm0yj2sn 392 21 process process NN cord-276598-tm0yj2sn 392 22 without without IN cord-276598-tm0yj2sn 392 23 any any DT cord-276598-tm0yj2sn 392 24 need need NN cord-276598-tm0yj2sn 392 25 for for IN cord-276598-tm0yj2sn 392 26 purification purification NN cord-276598-tm0yj2sn 392 27 of of IN cord-276598-tm0yj2sn 392 28 the the DT cord-276598-tm0yj2sn 392 29 starting starting NN cord-276598-tm0yj2sn 392 30 material material NN cord-276598-tm0yj2sn 392 31 , , , cord-276598-tm0yj2sn 392 32 thereby thereby RB cord-276598-tm0yj2sn 392 33 making make VBG cord-276598-tm0yj2sn 393 1 the the DT cord-276598-tm0yj2sn 393 2 process process NN cord-276598-tm0yj2sn 393 3 cost cost NN cord-276598-tm0yj2sn 393 4 - - HYPH cord-276598-tm0yj2sn 393 5 and and CC cord-276598-tm0yj2sn 393 6 time time NN cord-276598-tm0yj2sn 393 7 - - HYPH cord-276598-tm0yj2sn 393 8 effective effective JJ cord-276598-tm0yj2sn 393 9 . . . cord-276598-tm0yj2sn 394 1 Apart apart RB cord-276598-tm0yj2sn 394 2 from from IN cord-276598-tm0yj2sn 394 3 eliminating eliminate VBG cord-276598-tm0yj2sn 394 4 hazardous hazardous JJ cord-276598-tm0yj2sn 394 5 starting starting NN cord-276598-tm0yj2sn 394 6 materials material NNS cord-276598-tm0yj2sn 394 7 , , , cord-276598-tm0yj2sn 394 8 the the DT cord-276598-tm0yj2sn 394 9 method method NN cord-276598-tm0yj2sn 394 10 uses use VBZ cord-276598-tm0yj2sn 394 11 fewer few JJR cord-276598-tm0yj2sn 394 12 chemical chemical NN cord-276598-tm0yj2sn 394 13 additives additive NNS cord-276598-tm0yj2sn 394 14 and and CC cord-276598-tm0yj2sn 394 15 generates generate VBZ cord-276598-tm0yj2sn 394 16 mainly mainly RB cord-276598-tm0yj2sn 394 17 water water NN cord-276598-tm0yj2sn 394 18 as as IN cord-276598-tm0yj2sn 394 19 a a DT cord-276598-tm0yj2sn 394 20 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 394 21 waste waste NN cord-276598-tm0yj2sn 394 22 . . . cord-276598-tm0yj2sn 395 1 Furthermore furthermore RB cord-276598-tm0yj2sn 395 2 , , , cord-276598-tm0yj2sn 395 3 the the DT cord-276598-tm0yj2sn 395 4 methods method NNS cord-276598-tm0yj2sn 395 5 offer offer VBP cord-276598-tm0yj2sn 395 6 a a DT cord-276598-tm0yj2sn 395 7 possibility possibility NN cord-276598-tm0yj2sn 395 8 of of IN cord-276598-tm0yj2sn 395 9 catalyst catalyst NN cord-276598-tm0yj2sn 395 10 recycling recycling NN cord-276598-tm0yj2sn 395 11 , , , cord-276598-tm0yj2sn 395 12 which which WDT cord-276598-tm0yj2sn 395 13 is be VBZ cord-276598-tm0yj2sn 395 14 an an DT cord-276598-tm0yj2sn 395 15 important important JJ cord-276598-tm0yj2sn 395 16 attribute attribute NN cord-276598-tm0yj2sn 395 17 for for IN cord-276598-tm0yj2sn 395 18 any any DT cord-276598-tm0yj2sn 395 19 green green JJ cord-276598-tm0yj2sn 395 20 chemical chemical NN cord-276598-tm0yj2sn 395 21 process process NN cord-276598-tm0yj2sn 395 22 in in IN cord-276598-tm0yj2sn 395 23 terms term NNS cord-276598-tm0yj2sn 395 24 of of IN cord-276598-tm0yj2sn 395 25 mass mass NN cord-276598-tm0yj2sn 395 26 production production NN cord-276598-tm0yj2sn 395 27 . . . cord-276598-tm0yj2sn 396 1 However however RB cord-276598-tm0yj2sn 396 2 , , , cord-276598-tm0yj2sn 396 3 a a DT cord-276598-tm0yj2sn 396 4 notable notable JJ cord-276598-tm0yj2sn 396 5 limitation limitation NN cord-276598-tm0yj2sn 396 6 of of IN cord-276598-tm0yj2sn 396 7 the the DT cord-276598-tm0yj2sn 396 8 synthetic synthetic JJ cord-276598-tm0yj2sn 396 9 route route NN cord-276598-tm0yj2sn 396 10 is be VBZ cord-276598-tm0yj2sn 396 11 the the DT cord-276598-tm0yj2sn 396 12 formation formation NN cord-276598-tm0yj2sn 396 13 of of IN cord-276598-tm0yj2sn 396 14 various various JJ cord-276598-tm0yj2sn 396 15 undesired undesired JJ cord-276598-tm0yj2sn 396 16 by by IN cord-276598-tm0yj2sn 396 17 - - HYPH cord-276598-tm0yj2sn 396 18 products product NNS cord-276598-tm0yj2sn 396 19 from from IN cord-276598-tm0yj2sn 396 20 the the DT cord-276598-tm0yj2sn 396 21 reactivities reactivity NNS cord-276598-tm0yj2sn 396 22 of of IN cord-276598-tm0yj2sn 396 23 H H NNP cord-276598-tm0yj2sn 396 24 - - HYPH cord-276598-tm0yj2sn 396 25 P p NN cord-276598-tm0yj2sn 396 26 and and CC cord-276598-tm0yj2sn 396 27 amine amine NN cord-276598-tm0yj2sn 396 28 with with IN cord-276598-tm0yj2sn 396 29 the the DT cord-276598-tm0yj2sn 396 30 catalysts catalyst NNS cord-276598-tm0yj2sn 396 31 under under IN cord-276598-tm0yj2sn 396 32 oxidative oxidative JJ cord-276598-tm0yj2sn 396 33 conditions condition NNS cord-276598-tm0yj2sn 396 34 [ [ -LRB- cord-276598-tm0yj2sn 396 35 103 103 CD cord-276598-tm0yj2sn 396 36 ] ] -RRB- cord-276598-tm0yj2sn 396 37 . . . cord-276598-tm0yj2sn 397 1 Guo Guo NNP cord-276598-tm0yj2sn 397 2 et et FW cord-276598-tm0yj2sn 397 3 al al NNP cord-276598-tm0yj2sn 397 4 . . . cord-276598-tm0yj2sn 397 5 used use VBD cord-276598-tm0yj2sn 397 6 visible visible JJ cord-276598-tm0yj2sn 397 7 light light NN cord-276598-tm0yj2sn 397 8 and and CC cord-276598-tm0yj2sn 397 9 organic organic JJ cord-276598-tm0yj2sn 397 10 dyes dye NNS cord-276598-tm0yj2sn 397 11 as as IN cord-276598-tm0yj2sn 397 12 catalysts catalyst NNS cord-276598-tm0yj2sn 397 13 for for IN cord-276598-tm0yj2sn 397 14 the the DT cord-276598-tm0yj2sn 397 15 dehydrogenative dehydrogenative JJ cord-276598-tm0yj2sn 397 16 cross cross JJ cord-276598-tm0yj2sn 397 17 - - JJ cord-276598-tm0yj2sn 397 18 coupling coupling JJ cord-276598-tm0yj2sn 397 19 reaction reaction NN cord-276598-tm0yj2sn 397 20 of of IN cord-276598-tm0yj2sn 397 21 ( ( -LRB- cord-276598-tm0yj2sn 397 22 EtO EtO NNP cord-276598-tm0yj2sn 397 23 ) ) -RRB- cord-276598-tm0yj2sn 397 24 2 2 CD cord-276598-tm0yj2sn 398 1 P(O)H p(o)h NN cord-276598-tm0yj2sn 399 1 ( ( -LRB- cord-276598-tm0yj2sn 399 2 H h NN cord-276598-tm0yj2sn 399 3 - - HYPH cord-276598-tm0yj2sn 399 4 P p NN cord-276598-tm0yj2sn 399 5 ) ) -RRB- cord-276598-tm0yj2sn 399 6 and and CC cord-276598-tm0yj2sn 399 7 amines amine NNS cord-276598-tm0yj2sn 399 8 ( ( -LRB- cord-276598-tm0yj2sn 399 9 aniline aniline NN cord-276598-tm0yj2sn 399 10 , , , cord-276598-tm0yj2sn 399 11 aniline aniline NN cord-276598-tm0yj2sn 399 12 derivatives derivative NNS cord-276598-tm0yj2sn 399 13 with with IN cord-276598-tm0yj2sn 399 14 CN CN NNP cord-276598-tm0yj2sn 399 15 , , , cord-276598-tm0yj2sn 399 16 X X NNP cord-276598-tm0yj2sn 399 17 , , , cord-276598-tm0yj2sn 399 18 Me -PRON- PRP cord-276598-tm0yj2sn 399 19 , , , cord-276598-tm0yj2sn 399 20 OMe OMe NNS cord-276598-tm0yj2sn 399 21 and and CC cord-276598-tm0yj2sn 399 22 1-naphthylamine 1-naphthylamine CD cord-276598-tm0yj2sn 399 23 ) ) -RRB- cord-276598-tm0yj2sn 399 24 to to TO cord-276598-tm0yj2sn 399 25 form form VB cord-276598-tm0yj2sn 399 26 the the DT cord-276598-tm0yj2sn 399 27 corresponding correspond VBG cord-276598-tm0yj2sn 399 28 P P NNP cord-276598-tm0yj2sn 399 29 - - HYPH cord-276598-tm0yj2sn 399 30 Ns Ns NNP cord-276598-tm0yj2sn 399 31 ( ( -LRB- cord-276598-tm0yj2sn 399 32 Scheme scheme NN cord-276598-tm0yj2sn 399 33 8) 8) . cord-276598-tm0yj2sn 399 34 [ [ -LRB- cord-276598-tm0yj2sn 399 35 110 110 CD cord-276598-tm0yj2sn 399 36 ] ] -RRB- cord-276598-tm0yj2sn 399 37 . . . cord-276598-tm0yj2sn 400 1 After after IN cord-276598-tm0yj2sn 400 2 an an DT cord-276598-tm0yj2sn 400 3 extraction extraction NN cord-276598-tm0yj2sn 400 4 , , , cord-276598-tm0yj2sn 400 5 the the DT cord-276598-tm0yj2sn 400 6 pure pure JJ cord-276598-tm0yj2sn 400 7 product product NN cord-276598-tm0yj2sn 400 8 was be VBD cord-276598-tm0yj2sn 400 9 formed form VBN cord-276598-tm0yj2sn 400 10 with with IN cord-276598-tm0yj2sn 400 11 isolated isolated JJ cord-276598-tm0yj2sn 400 12 yield yield NN cord-276598-tm0yj2sn 400 13 in in IN cord-276598-tm0yj2sn 400 14 the the DT cord-276598-tm0yj2sn 400 15 range range NN cord-276598-tm0yj2sn 400 16 of of IN cord-276598-tm0yj2sn 400 17 0 0 CD cord-276598-tm0yj2sn 400 18 - - SYM cord-276598-tm0yj2sn 400 19 99 99 CD cord-276598-tm0yj2sn 400 20 % % NN cord-276598-tm0yj2sn 400 21 . . . cord-276598-tm0yj2sn 401 1 It -PRON- PRP cord-276598-tm0yj2sn 401 2 is be VBZ cord-276598-tm0yj2sn 401 3 noteworthy noteworthy JJ cord-276598-tm0yj2sn 401 4 that that IN cord-276598-tm0yj2sn 401 5 the the DT cord-276598-tm0yj2sn 401 6 method method NN cord-276598-tm0yj2sn 401 7 was be VBD cord-276598-tm0yj2sn 401 8 not not RB cord-276598-tm0yj2sn 401 9 effective effective JJ cord-276598-tm0yj2sn 401 10 when when WRB cord-276598-tm0yj2sn 401 11 vinylaniline vinylaniline NN cord-276598-tm0yj2sn 401 12 and and CC cord-276598-tm0yj2sn 401 13 2-aminothiazole 2-aminothiazole CD cord-276598-tm0yj2sn 401 14 were be VBD cord-276598-tm0yj2sn 401 15 used use VBN cord-276598-tm0yj2sn 401 16 because because IN cord-276598-tm0yj2sn 401 17 of of IN cord-276598-tm0yj2sn 401 18 their -PRON- PRP$ cord-276598-tm0yj2sn 401 19 radical radical JJ cord-276598-tm0yj2sn 401 20 sensitivity sensitivity NN cord-276598-tm0yj2sn 401 21 making make VBG cord-276598-tm0yj2sn 401 22 them -PRON- PRP cord-276598-tm0yj2sn 401 23 prone prone JJ cord-276598-tm0yj2sn 401 24 to to IN cord-276598-tm0yj2sn 401 25 either either CC cord-276598-tm0yj2sn 401 26 polymerization polymerization NN cord-276598-tm0yj2sn 401 27 or or CC cord-276598-tm0yj2sn 401 28 decomposition decomposition NN cord-276598-tm0yj2sn 401 29 in in IN cord-276598-tm0yj2sn 401 30 the the DT cord-276598-tm0yj2sn 401 31 reaction reaction NN cord-276598-tm0yj2sn 401 32 media medium NNS cord-276598-tm0yj2sn 401 33 , , , cord-276598-tm0yj2sn 401 34 respectively respectively RB cord-276598-tm0yj2sn 401 35 . . . cord-276598-tm0yj2sn 402 1 Although although IN cord-276598-tm0yj2sn 402 2 no no DT cord-276598-tm0yj2sn 402 3 product product NN cord-276598-tm0yj2sn 402 4 was be VBD cord-276598-tm0yj2sn 402 5 formed form VBN cord-276598-tm0yj2sn 402 6 when when WRB cord-276598-tm0yj2sn 402 7 secondary secondary JJ cord-276598-tm0yj2sn 402 8 aliphatic aliphatic JJ cord-276598-tm0yj2sn 402 9 amines amine NNS cord-276598-tm0yj2sn 402 10 were be VBD cord-276598-tm0yj2sn 402 11 used use VBN cord-276598-tm0yj2sn 402 12 , , , cord-276598-tm0yj2sn 402 13 moderate moderate JJ cord-276598-tm0yj2sn 402 14 yields yield NNS cord-276598-tm0yj2sn 402 15 of of IN cord-276598-tm0yj2sn 402 16 up up IN cord-276598-tm0yj2sn 402 17 to to TO cord-276598-tm0yj2sn 402 18 59 59 CD cord-276598-tm0yj2sn 402 19 % % NN cord-276598-tm0yj2sn 402 20 were be VBD cord-276598-tm0yj2sn 402 21 obtained obtain VBN cord-276598-tm0yj2sn 402 22 from from IN cord-276598-tm0yj2sn 402 23 primary primary JJ cord-276598-tm0yj2sn 402 24 or or CC cord-276598-tm0yj2sn 402 25 tertiary tertiary JJ cord-276598-tm0yj2sn 402 26 aliphatic aliphatic JJ cord-276598-tm0yj2sn 402 27 amines amine NNS cord-276598-tm0yj2sn 402 28 , , , cord-276598-tm0yj2sn 402 29 while while IN cord-276598-tm0yj2sn 402 30 a a DT cord-276598-tm0yj2sn 402 31 complex complex JJ cord-276598-tm0yj2sn 402 32 mixture mixture NN cord-276598-tm0yj2sn 402 33 of of IN cord-276598-tm0yj2sn 402 34 products product NNS cord-276598-tm0yj2sn 402 35 was be VBD cord-276598-tm0yj2sn 402 36 formed form VBN cord-276598-tm0yj2sn 402 37 when when WRB cord-276598-tm0yj2sn 402 38 an an DT cord-276598-tm0yj2sn 402 39 aromatic aromatic JJ cord-276598-tm0yj2sn 402 40 H h NN cord-276598-tm0yj2sn 402 41 - - HYPH cord-276598-tm0yj2sn 402 42 P P NNP cord-276598-tm0yj2sn 402 43 was be VBD cord-276598-tm0yj2sn 402 44 used use VBN cord-276598-tm0yj2sn 402 45 . . . cord-276598-tm0yj2sn 403 1 [ [ -LRB- cord-276598-tm0yj2sn 403 2 111 111 CD cord-276598-tm0yj2sn 403 3 ] ] -RRB- cord-276598-tm0yj2sn 403 4 . . . cord-276598-tm0yj2sn 404 1 The the DT cord-276598-tm0yj2sn 404 2 crude crude JJ cord-276598-tm0yj2sn 404 3 products product NNS cord-276598-tm0yj2sn 404 4 were be VBD cord-276598-tm0yj2sn 404 5 purified purify VBN cord-276598-tm0yj2sn 404 6 by by IN cord-276598-tm0yj2sn 404 7 column column NN cord-276598-tm0yj2sn 404 8 chromatography chromatography NN cord-276598-tm0yj2sn 404 9 ( ( -LRB- cord-276598-tm0yj2sn 404 10 on on IN cord-276598-tm0yj2sn 404 11 silica silica NN cord-276598-tm0yj2sn 404 12 ) ) -RRB- cord-276598-tm0yj2sn 404 13 with with IN cord-276598-tm0yj2sn 404 14 isolated isolated JJ cord-276598-tm0yj2sn 404 15 yields yield NNS cord-276598-tm0yj2sn 404 16 of of IN cord-276598-tm0yj2sn 404 17 65 65 CD cord-276598-tm0yj2sn 404 18 % % NN cord-276598-tm0yj2sn 404 19 and and CC cord-276598-tm0yj2sn 404 20 31 31 CD cord-276598-tm0yj2sn 404 21 % % NN cord-276598-tm0yj2sn 404 22 for for IN cord-276598-tm0yj2sn 404 23 the the DT cord-276598-tm0yj2sn 404 24 use use NN cord-276598-tm0yj2sn 404 25 of of IN cord-276598-tm0yj2sn 404 26 benzylamine benzylamine NN cord-276598-tm0yj2sn 404 27 and and CC cord-276598-tm0yj2sn 404 28 4-chloroaniline 4-chloroaniline CD cord-276598-tm0yj2sn 404 29 , , , cord-276598-tm0yj2sn 404 30 respectively respectively RB cord-276598-tm0yj2sn 404 31 . . . cord-276598-tm0yj2sn 405 1 Other other JJ cord-276598-tm0yj2sn 405 2 amines amine NNS cord-276598-tm0yj2sn 405 3 were be VBD cord-276598-tm0yj2sn 405 4 not not RB cord-276598-tm0yj2sn 405 5 investigated investigate VBN cord-276598-tm0yj2sn 405 6 . . . cord-276598-tm0yj2sn 406 1 Although although IN cord-276598-tm0yj2sn 406 2 the the DT cord-276598-tm0yj2sn 406 3 method method NN cord-276598-tm0yj2sn 406 4 uses use VBZ cord-276598-tm0yj2sn 406 5 an an DT cord-276598-tm0yj2sn 406 6 inexpensive inexpensive JJ cord-276598-tm0yj2sn 406 7 catalyst catalyst NN cord-276598-tm0yj2sn 406 8 and and CC cord-276598-tm0yj2sn 406 9 oxidant oxidant NN cord-276598-tm0yj2sn 406 10 , , , cord-276598-tm0yj2sn 406 11 the the DT cord-276598-tm0yj2sn 406 12 applicability applicability NN cord-276598-tm0yj2sn 406 13 of of IN cord-276598-tm0yj2sn 406 14 the the DT cord-276598-tm0yj2sn 406 15 process process NN cord-276598-tm0yj2sn 406 16 was be VBD cord-276598-tm0yj2sn 406 17 not not RB cord-276598-tm0yj2sn 406 18 explored explore VBN cord-276598-tm0yj2sn 406 19 using use VBG cord-276598-tm0yj2sn 406 20 diverse diverse JJ cord-276598-tm0yj2sn 406 21 H h NN cord-276598-tm0yj2sn 406 22 - - HYPH cord-276598-tm0yj2sn 406 23 P p NN cord-276598-tm0yj2sn 406 24 and and CC cord-276598-tm0yj2sn 406 25 amines amine NNS cord-276598-tm0yj2sn 406 26 . . . cord-276598-tm0yj2sn 407 1 Scheme scheme NN cord-276598-tm0yj2sn 407 2 9 9 CD cord-276598-tm0yj2sn 407 3 . . . cord-276598-tm0yj2sn 408 1 Oxidative oxidative JJ cord-276598-tm0yj2sn 408 2 cross cross JJ cord-276598-tm0yj2sn 408 3 - - JJ cord-276598-tm0yj2sn 408 4 coupling coupling JJ cord-276598-tm0yj2sn 408 5 reaction reaction NN cord-276598-tm0yj2sn 408 6 of of IN cord-276598-tm0yj2sn 408 7 amines amine NNS cord-276598-tm0yj2sn 408 8 and and CC cord-276598-tm0yj2sn 408 9 H h NN cord-276598-tm0yj2sn 408 10 - - HYPH cord-276598-tm0yj2sn 408 11 phosphonates phosphonate NNS cord-276598-tm0yj2sn 408 12 to to TO cord-276598-tm0yj2sn 408 13 form form VB cord-276598-tm0yj2sn 408 14 phosphoramidates phosphoramidate NNS cord-276598-tm0yj2sn 408 15 in in IN cord-276598-tm0yj2sn 408 16 the the DT cord-276598-tm0yj2sn 408 17 presence presence NN cord-276598-tm0yj2sn 408 18 of of IN cord-276598-tm0yj2sn 408 19 LiI lii NN cord-276598-tm0yj2sn 408 20 / / SYM cord-276598-tm0yj2sn 408 21 TBHP TBHP NNP cord-276598-tm0yj2sn 408 22 . . . cord-276598-tm0yj2sn 409 1 [ [ -LRB- cord-276598-tm0yj2sn 409 2 111 111 CD cord-276598-tm0yj2sn 409 3 ] ] -RRB- cord-276598-tm0yj2sn 409 4 . . . cord-276598-tm0yj2sn 410 1 The the DT cord-276598-tm0yj2sn 410 2 crude crude JJ cord-276598-tm0yj2sn 410 3 products product NNS cord-276598-tm0yj2sn 410 4 were be VBD cord-276598-tm0yj2sn 410 5 purified purify VBN cord-276598-tm0yj2sn 410 6 by by IN cord-276598-tm0yj2sn 410 7 column column NN cord-276598-tm0yj2sn 410 8 chromatography chromatography NN cord-276598-tm0yj2sn 410 9 ( ( -LRB- cord-276598-tm0yj2sn 410 10 on on IN cord-276598-tm0yj2sn 410 11 silica silica NN cord-276598-tm0yj2sn 410 12 ) ) -RRB- cord-276598-tm0yj2sn 410 13 with with IN cord-276598-tm0yj2sn 410 14 isolated isolated JJ cord-276598-tm0yj2sn 410 15 yields yield NNS cord-276598-tm0yj2sn 410 16 of of IN cord-276598-tm0yj2sn 410 17 65 65 CD cord-276598-tm0yj2sn 410 18 % % NN cord-276598-tm0yj2sn 410 19 and and CC cord-276598-tm0yj2sn 410 20 31 31 CD cord-276598-tm0yj2sn 410 21 % % NN cord-276598-tm0yj2sn 410 22 for for IN cord-276598-tm0yj2sn 410 23 the the DT cord-276598-tm0yj2sn 410 24 use use NN cord-276598-tm0yj2sn 410 25 of of IN cord-276598-tm0yj2sn 410 26 benzylamine benzylamine NN cord-276598-tm0yj2sn 410 27 and and CC cord-276598-tm0yj2sn 410 28 4-chloroaniline 4-chloroaniline CD cord-276598-tm0yj2sn 410 29 , , , cord-276598-tm0yj2sn 410 30 respectively respectively RB cord-276598-tm0yj2sn 410 31 . . . cord-276598-tm0yj2sn 411 1 Other other JJ cord-276598-tm0yj2sn 411 2 amines amine NNS cord-276598-tm0yj2sn 411 3 were be VBD cord-276598-tm0yj2sn 411 4 not not RB cord-276598-tm0yj2sn 411 5 investigated investigate VBN cord-276598-tm0yj2sn 411 6 . . . cord-276598-tm0yj2sn 412 1 Although although IN cord-276598-tm0yj2sn 412 2 the the DT cord-276598-tm0yj2sn 412 3 method method NN cord-276598-tm0yj2sn 412 4 uses use VBZ cord-276598-tm0yj2sn 412 5 an an DT cord-276598-tm0yj2sn 412 6 inexpensive inexpensive JJ cord-276598-tm0yj2sn 412 7 catalyst catalyst NN cord-276598-tm0yj2sn 412 8 and and CC cord-276598-tm0yj2sn 412 9 oxidant oxidant NN cord-276598-tm0yj2sn 412 10 , , , cord-276598-tm0yj2sn 412 11 the the DT cord-276598-tm0yj2sn 412 12 applicability applicability NN cord-276598-tm0yj2sn 412 13 of of IN cord-276598-tm0yj2sn 412 14 the the DT cord-276598-tm0yj2sn 412 15 process process NN cord-276598-tm0yj2sn 412 16 was be VBD cord-276598-tm0yj2sn 412 17 not not RB cord-276598-tm0yj2sn 412 18 explored explore VBN cord-276598-tm0yj2sn 412 19 using use VBG cord-276598-tm0yj2sn 412 20 diverse diverse JJ cord-276598-tm0yj2sn 412 21 H h NN cord-276598-tm0yj2sn 412 22 - - HYPH cord-276598-tm0yj2sn 412 23 P p NN cord-276598-tm0yj2sn 412 24 and and CC cord-276598-tm0yj2sn 412 25 amines amine NNS cord-276598-tm0yj2sn 412 26 . . . cord-276598-tm0yj2sn 413 1 lithium lithium NN cord-276598-tm0yj2sn 413 2 iodide iodide NN cord-276598-tm0yj2sn 413 3 - - HYPH cord-276598-tm0yj2sn 413 4 tert tert NN cord-276598-tm0yj2sn 413 5 - - HYPH cord-276598-tm0yj2sn 413 6 butyl butyl NN cord-276598-tm0yj2sn 413 7 hydroperoxide hydroperoxide NN cord-276598-tm0yj2sn 414 1 ( ( -LRB- cord-276598-tm0yj2sn 414 2 LiI lii NN cord-276598-tm0yj2sn 414 3 / / SYM cord-276598-tm0yj2sn 414 4 TBHP TBHP NNP cord-276598-tm0yj2sn 414 5 ) ) -RRB- cord-276598-tm0yj2sn 414 6 was be VBD cord-276598-tm0yj2sn 414 7 used use VBN cord-276598-tm0yj2sn 414 8 for for IN cord-276598-tm0yj2sn 414 9 the the DT cord-276598-tm0yj2sn 414 10 synthesis synthesis NN cord-276598-tm0yj2sn 414 11 of of IN cord-276598-tm0yj2sn 414 12 P P NNP cord-276598-tm0yj2sn 414 13 - - HYPH cord-276598-tm0yj2sn 414 14 N N NNP cord-276598-tm0yj2sn 414 15 and and CC cord-276598-tm0yj2sn 414 16 other other JJ cord-276598-tm0yj2sn 414 17 compounds compound NNS cord-276598-tm0yj2sn 414 18 by by IN cord-276598-tm0yj2sn 414 19 Reddy Reddy NNP cord-276598-tm0yj2sn 414 20 et et NNP cord-276598-tm0yj2sn 414 21 al al NNP cord-276598-tm0yj2sn 414 22 . . . cord-276598-tm0yj2sn 415 1 ( ( -LRB- cord-276598-tm0yj2sn 415 2 Scheme scheme NN cord-276598-tm0yj2sn 415 3 9 9 CD cord-276598-tm0yj2sn 415 4 ) ) -RRB- cord-276598-tm0yj2sn 415 5 [ [ -LRB- cord-276598-tm0yj2sn 415 6 111 111 CD cord-276598-tm0yj2sn 415 7 ] ] -RRB- cord-276598-tm0yj2sn 415 8 . . . cord-276598-tm0yj2sn 416 1 The the DT cord-276598-tm0yj2sn 416 2 crude crude JJ cord-276598-tm0yj2sn 416 3 products product NNS cord-276598-tm0yj2sn 416 4 were be VBD cord-276598-tm0yj2sn 416 5 purified purify VBN cord-276598-tm0yj2sn 416 6 by by IN cord-276598-tm0yj2sn 416 7 column column NN cord-276598-tm0yj2sn 416 8 chromatography chromatography NN cord-276598-tm0yj2sn 416 9 ( ( -LRB- cord-276598-tm0yj2sn 416 10 on on IN cord-276598-tm0yj2sn 416 11 silica silica NN cord-276598-tm0yj2sn 416 12 ) ) -RRB- cord-276598-tm0yj2sn 416 13 with with IN cord-276598-tm0yj2sn 416 14 isolated isolated JJ cord-276598-tm0yj2sn 416 15 yields yield NNS cord-276598-tm0yj2sn 416 16 of of IN cord-276598-tm0yj2sn 416 17 65 65 CD cord-276598-tm0yj2sn 416 18 % % NN cord-276598-tm0yj2sn 416 19 and and CC cord-276598-tm0yj2sn 416 20 31 31 CD cord-276598-tm0yj2sn 416 21 % % NN cord-276598-tm0yj2sn 416 22 for for IN cord-276598-tm0yj2sn 416 23 the the DT cord-276598-tm0yj2sn 416 24 use use NN cord-276598-tm0yj2sn 416 25 of of IN cord-276598-tm0yj2sn 416 26 benzylamine benzylamine NN cord-276598-tm0yj2sn 416 27 and and CC cord-276598-tm0yj2sn 416 28 4-chloroaniline 4-chloroaniline CD cord-276598-tm0yj2sn 416 29 , , , cord-276598-tm0yj2sn 416 30 respectively respectively RB cord-276598-tm0yj2sn 416 31 . . . cord-276598-tm0yj2sn 417 1 Other other JJ cord-276598-tm0yj2sn 417 2 amines amine NNS cord-276598-tm0yj2sn 417 3 were be VBD cord-276598-tm0yj2sn 417 4 not not RB cord-276598-tm0yj2sn 417 5 investigated investigate VBN cord-276598-tm0yj2sn 417 6 . . . cord-276598-tm0yj2sn 418 1 Although although IN cord-276598-tm0yj2sn 418 2 the the DT cord-276598-tm0yj2sn 418 3 method method NN cord-276598-tm0yj2sn 418 4 uses use VBZ cord-276598-tm0yj2sn 418 5 an an DT cord-276598-tm0yj2sn 418 6 inexpensive inexpensive JJ cord-276598-tm0yj2sn 418 7 catalyst catalyst NN cord-276598-tm0yj2sn 418 8 and and CC cord-276598-tm0yj2sn 418 9 oxidant oxidant NN cord-276598-tm0yj2sn 418 10 , , , cord-276598-tm0yj2sn 418 11 the the DT cord-276598-tm0yj2sn 418 12 applicability applicability NN cord-276598-tm0yj2sn 418 13 of of IN cord-276598-tm0yj2sn 418 14 the the DT cord-276598-tm0yj2sn 418 15 process process NN cord-276598-tm0yj2sn 418 16 was be VBD cord-276598-tm0yj2sn 418 17 not not RB cord-276598-tm0yj2sn 418 18 explored explore VBN cord-276598-tm0yj2sn 418 19 using use VBG cord-276598-tm0yj2sn 418 20 diverse diverse JJ cord-276598-tm0yj2sn 418 21 H h NN cord-276598-tm0yj2sn 418 22 - - HYPH cord-276598-tm0yj2sn 418 23 P p NN cord-276598-tm0yj2sn 418 24 and and CC cord-276598-tm0yj2sn 418 25 amines amine NNS cord-276598-tm0yj2sn 418 26 . . . cord-276598-tm0yj2sn 419 1 Scheme scheme NN cord-276598-tm0yj2sn 419 2 9 9 CD cord-276598-tm0yj2sn 419 3 . . . cord-276598-tm0yj2sn 420 1 Oxidative oxidative JJ cord-276598-tm0yj2sn 420 2 cross cross JJ cord-276598-tm0yj2sn 420 3 - - JJ cord-276598-tm0yj2sn 420 4 coupling coupling JJ cord-276598-tm0yj2sn 420 5 reaction reaction NN cord-276598-tm0yj2sn 420 6 of of IN cord-276598-tm0yj2sn 420 7 amines amine NNS cord-276598-tm0yj2sn 420 8 and and CC cord-276598-tm0yj2sn 420 9 H h NN cord-276598-tm0yj2sn 420 10 - - HYPH cord-276598-tm0yj2sn 420 11 phosphonates phosphonate NNS cord-276598-tm0yj2sn 420 12 to to TO cord-276598-tm0yj2sn 420 13 form form VB cord-276598-tm0yj2sn 420 14 phosphoramidates phosphoramidate NNS cord-276598-tm0yj2sn 420 15 in in IN cord-276598-tm0yj2sn 420 16 the the DT cord-276598-tm0yj2sn 420 17 presence presence NN cord-276598-tm0yj2sn 420 18 of of IN cord-276598-tm0yj2sn 420 19 LiI lii NN cord-276598-tm0yj2sn 420 20 / / SYM cord-276598-tm0yj2sn 420 21 TBHP TBHP NNP cord-276598-tm0yj2sn 420 22 . . . cord-276598-tm0yj2sn 421 1 Many many JJ cord-276598-tm0yj2sn 421 2 conventional conventional JJ cord-276598-tm0yj2sn 421 3 routes route NNS cord-276598-tm0yj2sn 421 4 to to IN cord-276598-tm0yj2sn 421 5 P P NNP cord-276598-tm0yj2sn 421 6 - - HYPH cord-276598-tm0yj2sn 421 7 N n CD cord-276598-tm0yj2sn 421 8 synthesis synthesis NN cord-276598-tm0yj2sn 421 9 as as IN cord-276598-tm0yj2sn 421 10 discussed discuss VBN cord-276598-tm0yj2sn 421 11 above above RB cord-276598-tm0yj2sn 421 12 have have VBP cord-276598-tm0yj2sn 421 13 used use VBN cord-276598-tm0yj2sn 421 14 H h NN cord-276598-tm0yj2sn 421 15 - - HYPH cord-276598-tm0yj2sn 421 16 P p NN cord-276598-tm0yj2sn 421 17 ( ( -LRB- cord-276598-tm0yj2sn 421 18 RO)2P(O)H ro)2p(o)h CD cord-276598-tm0yj2sn 422 1 ( ( -LRB- cord-276598-tm0yj2sn 422 2 R r NN cord-276598-tm0yj2sn 422 3 = = NN cord-276598-tm0yj2sn 422 4 alkyl alkyl NN cord-276598-tm0yj2sn 422 5 , , , cord-276598-tm0yj2sn 423 1 Bn Bn NNP cord-276598-tm0yj2sn 423 2 , , , cord-276598-tm0yj2sn 423 3 Ph Ph NNP cord-276598-tm0yj2sn 423 4 ) ) -RRB- cord-276598-tm0yj2sn 423 5 or or CC cord-276598-tm0yj2sn 424 1 ( ( -LRB- cord-276598-tm0yj2sn 424 2 RO)2P(O)Cl RO)2P(O)Cl NNP cord-276598-tm0yj2sn 424 3 ( ( -LRB- cord-276598-tm0yj2sn 424 4 dACP dacp NN cord-276598-tm0yj2sn 424 5 ; ; : cord-276598-tm0yj2sn 424 6 R r NN cord-276598-tm0yj2sn 424 7 = = NN cord-276598-tm0yj2sn 424 8 alkyl alkyl NN cord-276598-tm0yj2sn 424 9 , , , cord-276598-tm0yj2sn 424 10 Bn Bn NNP cord-276598-tm0yj2sn 424 11 , , , cord-276598-tm0yj2sn 424 12 Ph Ph NNP cord-276598-tm0yj2sn 424 13 ) ) -RRB- cord-276598-tm0yj2sn 424 14 and and CC cord-276598-tm0yj2sn 424 15 amine amine NN cord-276598-tm0yj2sn 424 16 as as IN cord-276598-tm0yj2sn 424 17 the the DT cord-276598-tm0yj2sn 424 18 P P NNP cord-276598-tm0yj2sn 424 19 - - , cord-276598-tm0yj2sn 424 20 and and CC cord-276598-tm0yj2sn 424 21 N n CD cord-276598-tm0yj2sn 424 22 - - HYPH cord-276598-tm0yj2sn 424 23 sources source NNS cord-276598-tm0yj2sn 424 24 , , , cord-276598-tm0yj2sn 424 25 respectively respectively RB cord-276598-tm0yj2sn 424 26 . . . cord-276598-tm0yj2sn 425 1 As as IN cord-276598-tm0yj2sn 425 2 a a DT cord-276598-tm0yj2sn 425 3 result result NN cord-276598-tm0yj2sn 425 4 , , , cord-276598-tm0yj2sn 425 5 derivatives derivative NNS cord-276598-tm0yj2sn 425 6 of of IN cord-276598-tm0yj2sn 425 7 P P NNP cord-276598-tm0yj2sn 425 8 - - HYPH cord-276598-tm0yj2sn 425 9 N N NNP cord-276598-tm0yj2sn 425 10 compounds compound NNS cord-276598-tm0yj2sn 425 11 synthesized synthesize VBN cord-276598-tm0yj2sn 425 12 through through IN cord-276598-tm0yj2sn 425 13 these these DT cord-276598-tm0yj2sn 425 14 routes route NNS cord-276598-tm0yj2sn 425 15 are be VBP cord-276598-tm0yj2sn 425 16 limited limit VBN cord-276598-tm0yj2sn 425 17 mainly mainly RB cord-276598-tm0yj2sn 425 18 to to IN cord-276598-tm0yj2sn 425 19 substituents substituent NNS cord-276598-tm0yj2sn 425 20 on on IN cord-276598-tm0yj2sn 425 21 the the DT cord-276598-tm0yj2sn 425 22 amine amine NN cord-276598-tm0yj2sn 425 23 starting start VBG cord-276598-tm0yj2sn 425 24 materials material NNS cord-276598-tm0yj2sn 425 25 . . . cord-276598-tm0yj2sn 426 1 Due due IN cord-276598-tm0yj2sn 426 2 to to IN cord-276598-tm0yj2sn 426 3 increased increase VBN cord-276598-tm0yj2sn 426 4 applicability applicability NN cord-276598-tm0yj2sn 426 5 , , , cord-276598-tm0yj2sn 426 6 it -PRON- PRP cord-276598-tm0yj2sn 426 7 has have VBZ cord-276598-tm0yj2sn 426 8 become become VBN cord-276598-tm0yj2sn 426 9 necessary necessary JJ cord-276598-tm0yj2sn 426 10 to to TO cord-276598-tm0yj2sn 426 11 synthesize synthesize VB cord-276598-tm0yj2sn 426 12 P P NNP cord-276598-tm0yj2sn 426 13 - - HYPH cord-276598-tm0yj2sn 426 14 N n CD cord-276598-tm0yj2sn 426 15 compounds compound NNS cord-276598-tm0yj2sn 426 16 with with IN cord-276598-tm0yj2sn 426 17 diverse diverse JJ cord-276598-tm0yj2sn 426 18 functionalities functionality NNS cord-276598-tm0yj2sn 426 19 . . . cord-276598-tm0yj2sn 427 1 In in IN cord-276598-tm0yj2sn 427 2 order order NN cord-276598-tm0yj2sn 427 3 to to TO cord-276598-tm0yj2sn 427 4 achieve achieve VB cord-276598-tm0yj2sn 427 5 this this DT cord-276598-tm0yj2sn 427 6 , , , cord-276598-tm0yj2sn 427 7 nitrene nitrene JJ cord-276598-tm0yj2sn 427 8 insertion insertion NN cord-276598-tm0yj2sn 427 9 from from IN cord-276598-tm0yj2sn 427 10 organic organic JJ cord-276598-tm0yj2sn 427 11 azides azide NNS cord-276598-tm0yj2sn 427 12 is be VBZ cord-276598-tm0yj2sn 427 13 becoming become VBG cord-276598-tm0yj2sn 427 14 a a DT cord-276598-tm0yj2sn 427 15 popular popular JJ cord-276598-tm0yj2sn 427 16 one one NN cord-276598-tm0yj2sn 427 17 because because IN cord-276598-tm0yj2sn 427 18 the the DT cord-276598-tm0yj2sn 427 19 route route NN cord-276598-tm0yj2sn 427 20 uses use VBZ cord-276598-tm0yj2sn 427 21 phosphoryl phosphoryl NNP cord-276598-tm0yj2sn 427 22 azide azide NN cord-276598-tm0yj2sn 427 23 , , , cord-276598-tm0yj2sn 427 24 which which WDT cord-276598-tm0yj2sn 427 25 acts act VBZ cord-276598-tm0yj2sn 427 26 a a DT cord-276598-tm0yj2sn 427 27 dual dual JJ cord-276598-tm0yj2sn 427 28 source source NN cord-276598-tm0yj2sn 427 29 of of IN cord-276598-tm0yj2sn 427 30 P p NN cord-276598-tm0yj2sn 427 31 and and CC cord-276598-tm0yj2sn 427 32 N. n. NN cord-276598-tm0yj2sn 428 1 In in IN cord-276598-tm0yj2sn 428 2 this this DT cord-276598-tm0yj2sn 428 3 case case NN cord-276598-tm0yj2sn 428 4 , , , cord-276598-tm0yj2sn 428 5 it -PRON- PRP cord-276598-tm0yj2sn 428 6 is be VBZ cord-276598-tm0yj2sn 428 7 possible possible JJ cord-276598-tm0yj2sn 428 8 to to TO cord-276598-tm0yj2sn 428 9 add add VB cord-276598-tm0yj2sn 428 10 ( ( -LRB- cord-276598-tm0yj2sn 428 11 or or CC cord-276598-tm0yj2sn 428 12 insert insert VB cord-276598-tm0yj2sn 428 13 ) ) -RRB- cord-276598-tm0yj2sn 428 14 diverse diverse JJ cord-276598-tm0yj2sn 428 15 molecules molecule NNS cord-276598-tm0yj2sn 428 16 on on IN cord-276598-tm0yj2sn 428 17 the the DT cord-276598-tm0yj2sn 428 18 P P NNP cord-276598-tm0yj2sn 428 19 - - HYPH cord-276598-tm0yj2sn 428 20 N N NNP cord-276598-tm0yj2sn 428 21 moiety moiety NN cord-276598-tm0yj2sn 428 22 through through IN cord-276598-tm0yj2sn 428 23 C C NNP cord-276598-tm0yj2sn 428 24 - - HYPH cord-276598-tm0yj2sn 428 25 N N NNP cord-276598-tm0yj2sn 428 26 bond bond NN cord-276598-tm0yj2sn 428 27 formation formation NN cord-276598-tm0yj2sn 428 28 . . . cord-276598-tm0yj2sn 429 1 A a DT cord-276598-tm0yj2sn 429 2 route route NN cord-276598-tm0yj2sn 429 3 to to IN cord-276598-tm0yj2sn 429 4 P p NN cord-276598-tm0yj2sn 429 5 - - HYPH cord-276598-tm0yj2sn 429 6 N n CD cord-276598-tm0yj2sn 429 7 formation formation NN cord-276598-tm0yj2sn 429 8 through through IN cord-276598-tm0yj2sn 429 9 C C NNP cord-276598-tm0yj2sn 429 10 - - HYPH cord-276598-tm0yj2sn 429 11 N N NNP cord-276598-tm0yj2sn 429 12 bond bond NN cord-276598-tm0yj2sn 429 13 formation formation NN cord-276598-tm0yj2sn 429 14 was be VBD cord-276598-tm0yj2sn 429 15 explored explore VBN cord-276598-tm0yj2sn 429 16 by by IN cord-276598-tm0yj2sn 429 17 Chang Chang NNP cord-276598-tm0yj2sn 429 18 , , , cord-276598-tm0yj2sn 429 19 Kim Kim NNP cord-276598-tm0yj2sn 429 20 , , , cord-276598-tm0yj2sn 429 21 and and CC cord-276598-tm0yj2sn 429 22 coworkers coworker NNS cord-276598-tm0yj2sn 429 23 ( ( -LRB- cord-276598-tm0yj2sn 429 24 Scheme scheme NN cord-276598-tm0yj2sn 429 25 10a 10a CD cord-276598-tm0yj2sn 429 26 ) ) -RRB- cord-276598-tm0yj2sn 429 27 [ [ -LRB- cord-276598-tm0yj2sn 429 28 112 112 CD cord-276598-tm0yj2sn 429 29 ] ] -RRB- cord-276598-tm0yj2sn 429 30 . . . cord-276598-tm0yj2sn 430 1 The the DT cord-276598-tm0yj2sn 430 2 P P NNP cord-276598-tm0yj2sn 430 3 - - HYPH cord-276598-tm0yj2sn 430 4 N N NNP cord-276598-tm0yj2sn 430 5 was be VBD cord-276598-tm0yj2sn 430 6 synthesized synthesize VBN cord-276598-tm0yj2sn 430 7 in in IN cord-276598-tm0yj2sn 430 8 the the DT cord-276598-tm0yj2sn 430 9 presence presence NN cord-276598-tm0yj2sn 430 10 of of IN cord-276598-tm0yj2sn 430 11 an an DT cord-276598-tm0yj2sn 430 12 Ir(III)-based ir(iii)-based JJ cord-276598-tm0yj2sn 430 13 catalyst catalyst NN cord-276598-tm0yj2sn 430 14 using use VBG cord-276598-tm0yj2sn 430 15 an an DT cord-276598-tm0yj2sn 430 16 amide amide NN cord-276598-tm0yj2sn 430 17 or or CC cord-276598-tm0yj2sn 430 18 a a DT cord-276598-tm0yj2sn 430 19 ketone ketone NN cord-276598-tm0yj2sn 430 20 and and CC cord-276598-tm0yj2sn 430 21 a a DT cord-276598-tm0yj2sn 430 22 phosphoryl phosphoryl NN cord-276598-tm0yj2sn 430 23 azide azide NN cord-276598-tm0yj2sn 430 24 . . . cord-276598-tm0yj2sn 431 1 The the DT cord-276598-tm0yj2sn 431 2 product product NN cord-276598-tm0yj2sn 431 3 was be VBD cord-276598-tm0yj2sn 431 4 purified purify VBN cord-276598-tm0yj2sn 431 5 by by IN cord-276598-tm0yj2sn 431 6 column column NN cord-276598-tm0yj2sn 431 7 chromatography chromatography NN cord-276598-tm0yj2sn 431 8 ( ( -LRB- cord-276598-tm0yj2sn 431 9 on on IN cord-276598-tm0yj2sn 431 10 silica silica NN cord-276598-tm0yj2sn 431 11 ) ) -RRB- cord-276598-tm0yj2sn 431 12 with with IN cord-276598-tm0yj2sn 431 13 isolated isolate VBN cord-276598-tm0yj2sn 431 14 yields yield NNS cord-276598-tm0yj2sn 431 15 in in IN cord-276598-tm0yj2sn 431 16 the the DT cord-276598-tm0yj2sn 431 17 range range NN cord-276598-tm0yj2sn 431 18 41 41 CD cord-276598-tm0yj2sn 431 19 - - SYM cord-276598-tm0yj2sn 431 20 99 99 CD cord-276598-tm0yj2sn 431 21 % % NN cord-276598-tm0yj2sn 431 22 . . . cord-276598-tm0yj2sn 432 1 The the DT cord-276598-tm0yj2sn 432 2 scope scope NN cord-276598-tm0yj2sn 432 3 of of IN cord-276598-tm0yj2sn 432 4 the the DT cord-276598-tm0yj2sn 432 5 synthesis synthesis NN cord-276598-tm0yj2sn 432 6 was be VBD cord-276598-tm0yj2sn 432 7 explored explore VBN cord-276598-tm0yj2sn 432 8 using use VBG cord-276598-tm0yj2sn 432 9 phosphoryl phosphoryl NNS cord-276598-tm0yj2sn 432 10 azide azide NN cord-276598-tm0yj2sn 432 11 substituted substitute VBN cord-276598-tm0yj2sn 432 12 with with IN cord-276598-tm0yj2sn 432 13 binaphthyl binaphthyl NN cord-276598-tm0yj2sn 432 14 , , , cord-276598-tm0yj2sn 432 15 aryl aryl NN cord-276598-tm0yj2sn 432 16 , , , cord-276598-tm0yj2sn 432 17 and and CC cord-276598-tm0yj2sn 432 18 alkyl alkyl JJ cord-276598-tm0yj2sn 432 19 groups group NNS cord-276598-tm0yj2sn 432 20 , , , cord-276598-tm0yj2sn 432 21 while while IN cord-276598-tm0yj2sn 432 22 the the DT cord-276598-tm0yj2sn 432 23 phenone phenone NN cord-276598-tm0yj2sn 432 24 had have VBD cord-276598-tm0yj2sn 432 25 substituents substituent NNS cord-276598-tm0yj2sn 432 26 such such JJ cord-276598-tm0yj2sn 432 27 as as IN cord-276598-tm0yj2sn 432 28 phenyl phenyl NN cord-276598-tm0yj2sn 432 29 , , , cord-276598-tm0yj2sn 432 30 methyl methyl NN cord-276598-tm0yj2sn 432 31 , , , cord-276598-tm0yj2sn 432 32 and and CC cord-276598-tm0yj2sn 432 33 isobutane isobutane NN cord-276598-tm0yj2sn 432 34 groups group NNS cord-276598-tm0yj2sn 432 35 . . . cord-276598-tm0yj2sn 433 1 Furthermore furthermore RB cord-276598-tm0yj2sn 433 2 , , , cord-276598-tm0yj2sn 433 3 4-methoxy 4-methoxy CD cord-276598-tm0yj2sn 433 4 , , , cord-276598-tm0yj2sn 433 5 4-CF3 4-cf3 CD cord-276598-tm0yj2sn 433 6 , , , cord-276598-tm0yj2sn 433 7 and and CC cord-276598-tm0yj2sn 433 8 tert tert NN cord-276598-tm0yj2sn 433 9 - - HYPH cord-276598-tm0yj2sn 433 10 butyl butyl NN cord-276598-tm0yj2sn 433 11 were be VBD cord-276598-tm0yj2sn 433 12 some some DT cord-276598-tm0yj2sn 433 13 of of IN cord-276598-tm0yj2sn 433 14 the the DT cord-276598-tm0yj2sn 433 15 substituents substituent NNS cord-276598-tm0yj2sn 433 16 on on IN cord-276598-tm0yj2sn 433 17 the the DT cord-276598-tm0yj2sn 433 18 benzamide benzamide NN cord-276598-tm0yj2sn 433 19 . . . cord-276598-tm0yj2sn 434 1 Biologically biologically RB cord-276598-tm0yj2sn 434 2 active active JJ cord-276598-tm0yj2sn 434 3 phosphoramidates phosphoramidate NNS cord-276598-tm0yj2sn 434 4 ( ( -LRB- cord-276598-tm0yj2sn 434 5 17 17 CD cord-276598-tm0yj2sn 434 6 and and CC cord-276598-tm0yj2sn 434 7 18 18 CD cord-276598-tm0yj2sn 434 8 ) ) -RRB- cord-276598-tm0yj2sn 434 9 were be VBD cord-276598-tm0yj2sn 434 10 synthesized synthesize VBN cord-276598-tm0yj2sn 434 11 through through IN cord-276598-tm0yj2sn 434 12 this this DT cord-276598-tm0yj2sn 434 13 method method NN cord-276598-tm0yj2sn 434 14 ( ( -LRB- cord-276598-tm0yj2sn 434 15 Figure Figure NNP cord-276598-tm0yj2sn 434 16 8 8 CD cord-276598-tm0yj2sn 434 17 ) ) -RRB- cord-276598-tm0yj2sn 434 18 . . . cord-276598-tm0yj2sn 435 1 Oxidative oxidative JJ cord-276598-tm0yj2sn 435 2 cross cross JJ cord-276598-tm0yj2sn 435 3 - - JJ cord-276598-tm0yj2sn 435 4 coupling coupling JJ cord-276598-tm0yj2sn 435 5 reaction reaction NN cord-276598-tm0yj2sn 435 6 of of IN cord-276598-tm0yj2sn 435 7 amines amine NNS cord-276598-tm0yj2sn 435 8 and and CC cord-276598-tm0yj2sn 435 9 H h NN cord-276598-tm0yj2sn 435 10 - - HYPH cord-276598-tm0yj2sn 435 11 phosphonates phosphonate NNS cord-276598-tm0yj2sn 435 12 to to TO cord-276598-tm0yj2sn 435 13 form form VB cord-276598-tm0yj2sn 435 14 phosphoramidates phosphoramidate NNS cord-276598-tm0yj2sn 435 15 in in IN cord-276598-tm0yj2sn 435 16 the the DT cord-276598-tm0yj2sn 435 17 presence presence NN cord-276598-tm0yj2sn 435 18 of of IN cord-276598-tm0yj2sn 435 19 LiI lii NN cord-276598-tm0yj2sn 435 20 / / SYM cord-276598-tm0yj2sn 435 21 TBHP TBHP NNP cord-276598-tm0yj2sn 435 22 . . . cord-276598-tm0yj2sn 436 1 Many many JJ cord-276598-tm0yj2sn 436 2 conventional conventional JJ cord-276598-tm0yj2sn 436 3 routes route NNS cord-276598-tm0yj2sn 436 4 to to IN cord-276598-tm0yj2sn 436 5 P P NNP cord-276598-tm0yj2sn 436 6 - - HYPH cord-276598-tm0yj2sn 436 7 N n CD cord-276598-tm0yj2sn 436 8 synthesis synthesis NN cord-276598-tm0yj2sn 436 9 as as IN cord-276598-tm0yj2sn 436 10 discussed discuss VBN cord-276598-tm0yj2sn 436 11 above above RB cord-276598-tm0yj2sn 436 12 have have VBP cord-276598-tm0yj2sn 436 13 used use VBN cord-276598-tm0yj2sn 436 14 H h NN cord-276598-tm0yj2sn 436 15 - - HYPH cord-276598-tm0yj2sn 436 16 P p NN cord-276598-tm0yj2sn 436 17 ( ( -LRB- cord-276598-tm0yj2sn 436 18 RO RO NNP cord-276598-tm0yj2sn 436 19 ) ) -RRB- cord-276598-tm0yj2sn 436 20 2 2 CD cord-276598-tm0yj2sn 437 1 P(O)H p(o)h NN cord-276598-tm0yj2sn 438 1 ( ( -LRB- cord-276598-tm0yj2sn 438 2 R r NN cord-276598-tm0yj2sn 438 3 = = NN cord-276598-tm0yj2sn 438 4 alkyl alkyl NN cord-276598-tm0yj2sn 438 5 , , , cord-276598-tm0yj2sn 439 1 Bn Bn NNP cord-276598-tm0yj2sn 439 2 , , , cord-276598-tm0yj2sn 439 3 Ph Ph NNP cord-276598-tm0yj2sn 439 4 ) ) -RRB- cord-276598-tm0yj2sn 439 5 or or CC cord-276598-tm0yj2sn 439 6 ( ( -LRB- cord-276598-tm0yj2sn 439 7 RO RO NNP cord-276598-tm0yj2sn 439 8 ) ) -RRB- cord-276598-tm0yj2sn 439 9 2 2 CD cord-276598-tm0yj2sn 440 1 P(O)Cl P(O)Cl VBN cord-276598-tm0yj2sn 441 1 ( ( -LRB- cord-276598-tm0yj2sn 441 2 dACP dacp JJ cord-276598-tm0yj2sn 441 3 ; ; : cord-276598-tm0yj2sn 441 4 R r NN cord-276598-tm0yj2sn 441 5 = = NN cord-276598-tm0yj2sn 441 6 alkyl alkyl NN cord-276598-tm0yj2sn 441 7 , , , cord-276598-tm0yj2sn 441 8 Bn Bn NNP cord-276598-tm0yj2sn 441 9 , , , cord-276598-tm0yj2sn 441 10 Ph Ph NNP cord-276598-tm0yj2sn 441 11 ) ) -RRB- cord-276598-tm0yj2sn 441 12 and and CC cord-276598-tm0yj2sn 441 13 amine amine NN cord-276598-tm0yj2sn 441 14 as as IN cord-276598-tm0yj2sn 441 15 the the DT cord-276598-tm0yj2sn 441 16 P P NNP cord-276598-tm0yj2sn 441 17 - - , cord-276598-tm0yj2sn 441 18 and and CC cord-276598-tm0yj2sn 441 19 N n CD cord-276598-tm0yj2sn 441 20 - - HYPH cord-276598-tm0yj2sn 441 21 sources source NNS cord-276598-tm0yj2sn 441 22 , , , cord-276598-tm0yj2sn 441 23 respectively respectively RB cord-276598-tm0yj2sn 441 24 . . . cord-276598-tm0yj2sn 442 1 As as IN cord-276598-tm0yj2sn 442 2 a a DT cord-276598-tm0yj2sn 442 3 result result NN cord-276598-tm0yj2sn 442 4 , , , cord-276598-tm0yj2sn 442 5 derivatives derivative NNS cord-276598-tm0yj2sn 442 6 of of IN cord-276598-tm0yj2sn 442 7 P P NNP cord-276598-tm0yj2sn 442 8 - - HYPH cord-276598-tm0yj2sn 442 9 N N NNP cord-276598-tm0yj2sn 442 10 compounds compound NNS cord-276598-tm0yj2sn 442 11 synthesized synthesize VBN cord-276598-tm0yj2sn 442 12 through through IN cord-276598-tm0yj2sn 442 13 these these DT cord-276598-tm0yj2sn 442 14 routes route NNS cord-276598-tm0yj2sn 442 15 are be VBP cord-276598-tm0yj2sn 442 16 limited limit VBN cord-276598-tm0yj2sn 442 17 mainly mainly RB cord-276598-tm0yj2sn 442 18 to to IN cord-276598-tm0yj2sn 442 19 substituents substituent NNS cord-276598-tm0yj2sn 442 20 on on IN cord-276598-tm0yj2sn 442 21 the the DT cord-276598-tm0yj2sn 442 22 amine amine NN cord-276598-tm0yj2sn 442 23 starting start VBG cord-276598-tm0yj2sn 442 24 materials material NNS cord-276598-tm0yj2sn 442 25 . . . cord-276598-tm0yj2sn 443 1 Due due IN cord-276598-tm0yj2sn 443 2 to to IN cord-276598-tm0yj2sn 443 3 increased increase VBN cord-276598-tm0yj2sn 443 4 applicability applicability NN cord-276598-tm0yj2sn 443 5 , , , cord-276598-tm0yj2sn 443 6 it -PRON- PRP cord-276598-tm0yj2sn 443 7 has have VBZ cord-276598-tm0yj2sn 443 8 become become VBN cord-276598-tm0yj2sn 443 9 necessary necessary JJ cord-276598-tm0yj2sn 443 10 to to TO cord-276598-tm0yj2sn 443 11 synthesize synthesize VB cord-276598-tm0yj2sn 443 12 P P NNP cord-276598-tm0yj2sn 443 13 - - HYPH cord-276598-tm0yj2sn 443 14 N n CD cord-276598-tm0yj2sn 443 15 compounds compound NNS cord-276598-tm0yj2sn 443 16 with with IN cord-276598-tm0yj2sn 443 17 diverse diverse JJ cord-276598-tm0yj2sn 443 18 functionalities functionality NNS cord-276598-tm0yj2sn 443 19 . . . cord-276598-tm0yj2sn 444 1 In in IN cord-276598-tm0yj2sn 444 2 order order NN cord-276598-tm0yj2sn 444 3 to to TO cord-276598-tm0yj2sn 444 4 achieve achieve VB cord-276598-tm0yj2sn 444 5 this this DT cord-276598-tm0yj2sn 444 6 , , , cord-276598-tm0yj2sn 444 7 nitrene nitrene JJ cord-276598-tm0yj2sn 444 8 insertion insertion NN cord-276598-tm0yj2sn 444 9 from from IN cord-276598-tm0yj2sn 444 10 organic organic JJ cord-276598-tm0yj2sn 444 11 azides azide NNS cord-276598-tm0yj2sn 444 12 is be VBZ cord-276598-tm0yj2sn 444 13 becoming become VBG cord-276598-tm0yj2sn 444 14 a a DT cord-276598-tm0yj2sn 444 15 popular popular JJ cord-276598-tm0yj2sn 444 16 one one NN cord-276598-tm0yj2sn 444 17 because because IN cord-276598-tm0yj2sn 444 18 the the DT cord-276598-tm0yj2sn 444 19 route route NN cord-276598-tm0yj2sn 444 20 uses use VBZ cord-276598-tm0yj2sn 444 21 phosphoryl phosphoryl NNP cord-276598-tm0yj2sn 444 22 azide azide NN cord-276598-tm0yj2sn 444 23 , , , cord-276598-tm0yj2sn 444 24 which which WDT cord-276598-tm0yj2sn 444 25 acts act VBZ cord-276598-tm0yj2sn 444 26 a a DT cord-276598-tm0yj2sn 444 27 dual dual JJ cord-276598-tm0yj2sn 444 28 source source NN cord-276598-tm0yj2sn 444 29 of of IN cord-276598-tm0yj2sn 444 30 P p NN cord-276598-tm0yj2sn 444 31 and and CC cord-276598-tm0yj2sn 444 32 N. n. NN cord-276598-tm0yj2sn 445 1 In in IN cord-276598-tm0yj2sn 445 2 this this DT cord-276598-tm0yj2sn 445 3 case case NN cord-276598-tm0yj2sn 445 4 , , , cord-276598-tm0yj2sn 445 5 it -PRON- PRP cord-276598-tm0yj2sn 445 6 is be VBZ cord-276598-tm0yj2sn 445 7 possible possible JJ cord-276598-tm0yj2sn 445 8 to to TO cord-276598-tm0yj2sn 445 9 add add VB cord-276598-tm0yj2sn 445 10 ( ( -LRB- cord-276598-tm0yj2sn 445 11 or or CC cord-276598-tm0yj2sn 445 12 insert insert VB cord-276598-tm0yj2sn 445 13 ) ) -RRB- cord-276598-tm0yj2sn 445 14 diverse diverse JJ cord-276598-tm0yj2sn 445 15 molecules molecule NNS cord-276598-tm0yj2sn 445 16 on on IN cord-276598-tm0yj2sn 445 17 the the DT cord-276598-tm0yj2sn 445 18 P P NNP cord-276598-tm0yj2sn 445 19 - - HYPH cord-276598-tm0yj2sn 445 20 N N NNP cord-276598-tm0yj2sn 445 21 moiety moiety NN cord-276598-tm0yj2sn 445 22 through through IN cord-276598-tm0yj2sn 445 23 C C NNP cord-276598-tm0yj2sn 445 24 - - HYPH cord-276598-tm0yj2sn 445 25 N N NNP cord-276598-tm0yj2sn 445 26 bond bond NN cord-276598-tm0yj2sn 445 27 formation formation NN cord-276598-tm0yj2sn 445 28 . . . cord-276598-tm0yj2sn 446 1 A a DT cord-276598-tm0yj2sn 446 2 route route NN cord-276598-tm0yj2sn 446 3 to to IN cord-276598-tm0yj2sn 446 4 P p NN cord-276598-tm0yj2sn 446 5 - - HYPH cord-276598-tm0yj2sn 446 6 N n CD cord-276598-tm0yj2sn 446 7 formation formation NN cord-276598-tm0yj2sn 446 8 through through IN cord-276598-tm0yj2sn 446 9 C C NNP cord-276598-tm0yj2sn 446 10 - - HYPH cord-276598-tm0yj2sn 446 11 N N NNP cord-276598-tm0yj2sn 446 12 bond bond NN cord-276598-tm0yj2sn 446 13 formation formation NN cord-276598-tm0yj2sn 446 14 was be VBD cord-276598-tm0yj2sn 446 15 explored explore VBN cord-276598-tm0yj2sn 446 16 by by IN cord-276598-tm0yj2sn 446 17 Chang Chang NNP cord-276598-tm0yj2sn 446 18 , , , cord-276598-tm0yj2sn 446 19 Kim Kim NNP cord-276598-tm0yj2sn 446 20 , , , cord-276598-tm0yj2sn 446 21 and and CC cord-276598-tm0yj2sn 446 22 coworkers coworker NNS cord-276598-tm0yj2sn 446 23 ( ( -LRB- cord-276598-tm0yj2sn 446 24 Scheme scheme NN cord-276598-tm0yj2sn 446 25 10a 10a CD cord-276598-tm0yj2sn 446 26 ) ) -RRB- cord-276598-tm0yj2sn 446 27 [ [ -LRB- cord-276598-tm0yj2sn 446 28 112 112 CD cord-276598-tm0yj2sn 446 29 ] ] -RRB- cord-276598-tm0yj2sn 446 30 . . . cord-276598-tm0yj2sn 447 1 The the DT cord-276598-tm0yj2sn 447 2 P P NNP cord-276598-tm0yj2sn 447 3 - - HYPH cord-276598-tm0yj2sn 447 4 N N NNP cord-276598-tm0yj2sn 447 5 was be VBD cord-276598-tm0yj2sn 447 6 synthesized synthesize VBN cord-276598-tm0yj2sn 447 7 in in IN cord-276598-tm0yj2sn 447 8 the the DT cord-276598-tm0yj2sn 447 9 presence presence NN cord-276598-tm0yj2sn 447 10 of of IN cord-276598-tm0yj2sn 447 11 an an DT cord-276598-tm0yj2sn 447 12 Ir(III)-based ir(iii)-based JJ cord-276598-tm0yj2sn 447 13 catalyst catalyst NN cord-276598-tm0yj2sn 447 14 using use VBG cord-276598-tm0yj2sn 447 15 an an DT cord-276598-tm0yj2sn 447 16 amide amide NN cord-276598-tm0yj2sn 447 17 or or CC cord-276598-tm0yj2sn 447 18 a a DT cord-276598-tm0yj2sn 447 19 ketone ketone NN cord-276598-tm0yj2sn 447 20 and and CC cord-276598-tm0yj2sn 447 21 a a DT cord-276598-tm0yj2sn 447 22 phosphoryl phosphoryl NN cord-276598-tm0yj2sn 447 23 azide azide NN cord-276598-tm0yj2sn 447 24 . . . cord-276598-tm0yj2sn 448 1 The the DT cord-276598-tm0yj2sn 448 2 product product NN cord-276598-tm0yj2sn 448 3 was be VBD cord-276598-tm0yj2sn 448 4 purified purify VBN cord-276598-tm0yj2sn 448 5 by by IN cord-276598-tm0yj2sn 448 6 column column NN cord-276598-tm0yj2sn 448 7 chromatography chromatography NN cord-276598-tm0yj2sn 448 8 ( ( -LRB- cord-276598-tm0yj2sn 448 9 on on IN cord-276598-tm0yj2sn 448 10 silica silica NN cord-276598-tm0yj2sn 448 11 ) ) -RRB- cord-276598-tm0yj2sn 448 12 with with IN cord-276598-tm0yj2sn 448 13 isolated isolate VBN cord-276598-tm0yj2sn 448 14 yields yield NNS cord-276598-tm0yj2sn 448 15 in in IN cord-276598-tm0yj2sn 448 16 the the DT cord-276598-tm0yj2sn 448 17 range range NN cord-276598-tm0yj2sn 448 18 41 41 CD cord-276598-tm0yj2sn 448 19 - - SYM cord-276598-tm0yj2sn 448 20 99 99 CD cord-276598-tm0yj2sn 448 21 % % NN cord-276598-tm0yj2sn 448 22 . . . cord-276598-tm0yj2sn 449 1 The the DT cord-276598-tm0yj2sn 449 2 scope scope NN cord-276598-tm0yj2sn 449 3 of of IN cord-276598-tm0yj2sn 449 4 the the DT cord-276598-tm0yj2sn 449 5 synthesis synthesis NN cord-276598-tm0yj2sn 449 6 was be VBD cord-276598-tm0yj2sn 449 7 explored explore VBN cord-276598-tm0yj2sn 449 8 using use VBG cord-276598-tm0yj2sn 449 9 phosphoryl phosphoryl NNS cord-276598-tm0yj2sn 449 10 azide azide NN cord-276598-tm0yj2sn 449 11 substituted substitute VBN cord-276598-tm0yj2sn 449 12 with with IN cord-276598-tm0yj2sn 449 13 binaphthyl binaphthyl NN cord-276598-tm0yj2sn 449 14 , , , cord-276598-tm0yj2sn 449 15 aryl aryl NN cord-276598-tm0yj2sn 449 16 , , , cord-276598-tm0yj2sn 449 17 and and CC cord-276598-tm0yj2sn 449 18 alkyl alkyl JJ cord-276598-tm0yj2sn 449 19 groups group NNS cord-276598-tm0yj2sn 449 20 , , , cord-276598-tm0yj2sn 449 21 while while IN cord-276598-tm0yj2sn 449 22 the the DT cord-276598-tm0yj2sn 449 23 phenone phenone NN cord-276598-tm0yj2sn 449 24 had have VBD cord-276598-tm0yj2sn 449 25 substituents substituent NNS cord-276598-tm0yj2sn 449 26 such such JJ cord-276598-tm0yj2sn 449 27 as as IN cord-276598-tm0yj2sn 449 28 phenyl phenyl NN cord-276598-tm0yj2sn 449 29 , , , cord-276598-tm0yj2sn 449 30 methyl methyl NN cord-276598-tm0yj2sn 449 31 , , , cord-276598-tm0yj2sn 449 32 and and CC cord-276598-tm0yj2sn 449 33 isobutane isobutane NN cord-276598-tm0yj2sn 449 34 groups group NNS cord-276598-tm0yj2sn 449 35 . . . cord-276598-tm0yj2sn 450 1 Furthermore furthermore RB cord-276598-tm0yj2sn 450 2 , , , cord-276598-tm0yj2sn 450 3 4-methoxy 4-methoxy CD cord-276598-tm0yj2sn 450 4 , , , cord-276598-tm0yj2sn 450 5 4-CF 4-cf CD cord-276598-tm0yj2sn 450 6 3 3 CD cord-276598-tm0yj2sn 450 7 , , , cord-276598-tm0yj2sn 450 8 and and CC cord-276598-tm0yj2sn 450 9 tert tert NN cord-276598-tm0yj2sn 450 10 - - HYPH cord-276598-tm0yj2sn 450 11 butyl butyl NN cord-276598-tm0yj2sn 450 12 were be VBD cord-276598-tm0yj2sn 450 13 some some DT cord-276598-tm0yj2sn 450 14 of of IN cord-276598-tm0yj2sn 450 15 the the DT cord-276598-tm0yj2sn 450 16 substituents substituent NNS cord-276598-tm0yj2sn 450 17 on on IN cord-276598-tm0yj2sn 450 18 the the DT cord-276598-tm0yj2sn 450 19 benzamide benzamide NN cord-276598-tm0yj2sn 450 20 . . . cord-276598-tm0yj2sn 451 1 Biologically biologically RB cord-276598-tm0yj2sn 451 2 active active JJ cord-276598-tm0yj2sn 451 3 phosphoramidates phosphoramidate NNS cord-276598-tm0yj2sn 451 4 ( ( -LRB- cord-276598-tm0yj2sn 451 5 17 17 CD cord-276598-tm0yj2sn 451 6 and and CC cord-276598-tm0yj2sn 451 7 18 18 CD cord-276598-tm0yj2sn 451 8 ) ) -RRB- cord-276598-tm0yj2sn 451 9 were be VBD cord-276598-tm0yj2sn 451 10 synthesized synthesize VBN cord-276598-tm0yj2sn 451 11 through through IN cord-276598-tm0yj2sn 451 12 this this DT cord-276598-tm0yj2sn 451 13 method method NN cord-276598-tm0yj2sn 451 14 ( ( -LRB- cord-276598-tm0yj2sn 451 15 Figure Figure NNP cord-276598-tm0yj2sn 451 16 8 8 CD cord-276598-tm0yj2sn 451 17 ) ) -RRB- cord-276598-tm0yj2sn 451 18 . . . cord-276598-tm0yj2sn 452 1 Che Che NNP cord-276598-tm0yj2sn 452 2 and and CC cord-276598-tm0yj2sn 452 3 coworkers coworker NNS cord-276598-tm0yj2sn 452 4 later later RB cord-276598-tm0yj2sn 452 5 introduced introduce VBD cord-276598-tm0yj2sn 452 6 a a DT cord-276598-tm0yj2sn 452 7 Ru Ru NNP cord-276598-tm0yj2sn 452 8 IV IV NNP cord-276598-tm0yj2sn 452 9 -porphyrin -porphyrin NN cord-276598-tm0yj2sn 452 10 - - HYPH cord-276598-tm0yj2sn 452 11 catalyst catalyst NN cord-276598-tm0yj2sn 452 12 to to TO cord-276598-tm0yj2sn 452 13 synthesize synthesize VB cord-276598-tm0yj2sn 452 14 N N NNP cord-276598-tm0yj2sn 452 15 - - HYPH cord-276598-tm0yj2sn 452 16 acylphosphoramidates acylphosphoramidates NNP cord-276598-tm0yj2sn 452 17 ( ( -LRB- cord-276598-tm0yj2sn 452 18 AcP AcP NNP cord-276598-tm0yj2sn 452 19 - - HYPH cord-276598-tm0yj2sn 452 20 N N NNP cord-276598-tm0yj2sn 452 21 ) ) -RRB- cord-276598-tm0yj2sn 452 22 from from IN cord-276598-tm0yj2sn 452 23 aldehydes aldehyde NNS cord-276598-tm0yj2sn 452 24 and and CC cord-276598-tm0yj2sn 452 25 phosphoryl phosphoryl NN cord-276598-tm0yj2sn 452 26 azide azide NN cord-276598-tm0yj2sn 452 27 through through IN cord-276598-tm0yj2sn 452 28 nitrene nitrene JJ cord-276598-tm0yj2sn 452 29 insertion insertion NN cord-276598-tm0yj2sn 452 30 ( ( -LRB- cord-276598-tm0yj2sn 452 31 Scheme scheme NN cord-276598-tm0yj2sn 452 32 10b 10b CD cord-276598-tm0yj2sn 452 33 ) ) -RRB- cord-276598-tm0yj2sn 452 34 [ [ -LRB- cord-276598-tm0yj2sn 452 35 113 113 CD cord-276598-tm0yj2sn 452 36 ] ] -RRB- cord-276598-tm0yj2sn 452 37 . . . cord-276598-tm0yj2sn 453 1 The the DT cord-276598-tm0yj2sn 453 2 product product NN cord-276598-tm0yj2sn 453 3 was be VBD cord-276598-tm0yj2sn 453 4 isolated isolate VBN cord-276598-tm0yj2sn 453 5 by by IN cord-276598-tm0yj2sn 453 6 column column NN cord-276598-tm0yj2sn 453 7 chromatography chromatography NN cord-276598-tm0yj2sn 453 8 ( ( -LRB- cord-276598-tm0yj2sn 453 9 on on IN cord-276598-tm0yj2sn 453 10 silica silica NN cord-276598-tm0yj2sn 453 11 ) ) -RRB- cord-276598-tm0yj2sn 453 12 . . . cord-276598-tm0yj2sn 454 1 The the DT cord-276598-tm0yj2sn 454 2 observed observed JJ cord-276598-tm0yj2sn 454 3 product product NN cord-276598-tm0yj2sn 454 4 conversions conversion NNS cord-276598-tm0yj2sn 454 5 were be VBD cord-276598-tm0yj2sn 454 6 in in IN cord-276598-tm0yj2sn 454 7 the the DT cord-276598-tm0yj2sn 454 8 range range NN cord-276598-tm0yj2sn 454 9 56 56 CD cord-276598-tm0yj2sn 454 10 - - SYM cord-276598-tm0yj2sn 454 11 99 99 CD cord-276598-tm0yj2sn 454 12 % % NN cord-276598-tm0yj2sn 454 13 . . . cord-276598-tm0yj2sn 455 1 Aromatic aromatic JJ cord-276598-tm0yj2sn 455 2 and and CC cord-276598-tm0yj2sn 455 3 aliphatic aliphatic JJ cord-276598-tm0yj2sn 455 4 aldehydes aldehyde NNS cord-276598-tm0yj2sn 455 5 such such JJ cord-276598-tm0yj2sn 455 6 as as IN cord-276598-tm0yj2sn 455 7 2-naphthaldehyde 2-naphthaldehyde CD cord-276598-tm0yj2sn 455 8 , , , cord-276598-tm0yj2sn 455 9 benzo[d benzo[d NNP cord-276598-tm0yj2sn 455 10 ] ] -RRB- cord-276598-tm0yj2sn 456 1 [ [ -LRB- cord-276598-tm0yj2sn 456 2 1 1 CD cord-276598-tm0yj2sn 456 3 , , , cord-276598-tm0yj2sn 456 4 3 3 CD cord-276598-tm0yj2sn 456 5 ] ] -RRB- cord-276598-tm0yj2sn 456 6 dioxole-5-carbaldehyde dioxole-5-carbaldehyde NNP cord-276598-tm0yj2sn 456 7 , , , cord-276598-tm0yj2sn 456 8 5,6-dihydro-2H 5,6-dihydro-2h CD cord-276598-tm0yj2sn 456 9 - - : cord-276598-tm0yj2sn 456 10 pyran-3-carbaldehyde pyran-3-carbaldehyde NNP cord-276598-tm0yj2sn 456 11 and and CC cord-276598-tm0yj2sn 456 12 3-methylbut-2-enal 3-methylbut-2-enal CD cord-276598-tm0yj2sn 456 13 were be VBD cord-276598-tm0yj2sn 456 14 used use VBN cord-276598-tm0yj2sn 456 15 in in IN cord-276598-tm0yj2sn 456 16 the the DT cord-276598-tm0yj2sn 456 17 reaction reaction NN cord-276598-tm0yj2sn 456 18 along along IN cord-276598-tm0yj2sn 456 19 with with IN cord-276598-tm0yj2sn 456 20 aromatic aromatic JJ cord-276598-tm0yj2sn 456 21 and and CC cord-276598-tm0yj2sn 456 22 aliphatic aliphatic JJ cord-276598-tm0yj2sn 456 23 phosphoryl phosphoryl NNS cord-276598-tm0yj2sn 456 24 azide azide NN cord-276598-tm0yj2sn 456 25 such such JJ cord-276598-tm0yj2sn 456 26 as as IN cord-276598-tm0yj2sn 456 27 3-nitrophenyl 3-nitrophenyl CD cord-276598-tm0yj2sn 457 1 ( ( -LRB- cord-276598-tm0yj2sn 457 2 4-nitrophenyl 4-nitrophenyl CD cord-276598-tm0yj2sn 457 3 ) ) -RRB- cord-276598-tm0yj2sn 457 4 phosphorazidate phosphorazidate NNP cord-276598-tm0yj2sn 457 5 , , , cord-276598-tm0yj2sn 457 6 bis(2,2,2-trichloroethyl bis(2,2,2-trichloroethyl NNP cord-276598-tm0yj2sn 457 7 ) ) -RRB- cord-276598-tm0yj2sn 457 8 phosphorazidate phosphorazidate NNP cord-276598-tm0yj2sn 457 9 , , , cord-276598-tm0yj2sn 457 10 and and CC cord-276598-tm0yj2sn 457 11 diethyl diethyl NNP cord-276598-tm0yj2sn 457 12 phosphorazidate phosphorazidate NNP cord-276598-tm0yj2sn 457 13 . . . cord-276598-tm0yj2sn 458 1 However however RB cord-276598-tm0yj2sn 458 2 , , , cord-276598-tm0yj2sn 458 3 lower low JJR cord-276598-tm0yj2sn 458 4 yields yield NNS cord-276598-tm0yj2sn 458 5 were be VBD cord-276598-tm0yj2sn 458 6 obtained obtain VBN cord-276598-tm0yj2sn 458 7 from from IN cord-276598-tm0yj2sn 458 8 aliphatic aliphatic JJ cord-276598-tm0yj2sn 458 9 aldehydes aldehyde NNS cord-276598-tm0yj2sn 458 10 when when WRB cord-276598-tm0yj2sn 458 11 compared compare VBN cord-276598-tm0yj2sn 458 12 with with IN cord-276598-tm0yj2sn 458 13 the the DT cord-276598-tm0yj2sn 458 14 aromatic aromatic JJ cord-276598-tm0yj2sn 458 15 aldehydes aldehyde NNS cord-276598-tm0yj2sn 458 16 , , , cord-276598-tm0yj2sn 458 17 suggesting suggest VBG cord-276598-tm0yj2sn 458 18 that that IN cord-276598-tm0yj2sn 458 19 the the DT cord-276598-tm0yj2sn 458 20 synthetic synthetic JJ cord-276598-tm0yj2sn 458 21 procedure procedure NN cord-276598-tm0yj2sn 458 22 favors favor VBZ cord-276598-tm0yj2sn 458 23 electron electron NN cord-276598-tm0yj2sn 458 24 - - HYPH cord-276598-tm0yj2sn 458 25 rich rich JJ cord-276598-tm0yj2sn 458 26 aromatic aromatic JJ cord-276598-tm0yj2sn 458 27 aldehydes aldehyde NNS cord-276598-tm0yj2sn 458 28 . . . cord-276598-tm0yj2sn 459 1 Che Che NNP cord-276598-tm0yj2sn 459 2 and and CC cord-276598-tm0yj2sn 459 3 coworkers coworker NNS cord-276598-tm0yj2sn 459 4 later later RB cord-276598-tm0yj2sn 459 5 introduced introduce VBD cord-276598-tm0yj2sn 459 6 a a DT cord-276598-tm0yj2sn 459 7 Ru Ru NNP cord-276598-tm0yj2sn 459 8 IV IV NNP cord-276598-tm0yj2sn 459 9 -porphyrin -porphyrin NN cord-276598-tm0yj2sn 459 10 - - HYPH cord-276598-tm0yj2sn 459 11 catalyst catalyst NN cord-276598-tm0yj2sn 459 12 to to TO cord-276598-tm0yj2sn 459 13 synthesize synthesize VB cord-276598-tm0yj2sn 459 14 N N NNP cord-276598-tm0yj2sn 459 15 - - HYPH cord-276598-tm0yj2sn 459 16 acylphosphoramidates acylphosphoramidates NNP cord-276598-tm0yj2sn 459 17 ( ( -LRB- cord-276598-tm0yj2sn 459 18 AcP AcP NNP cord-276598-tm0yj2sn 459 19 - - HYPH cord-276598-tm0yj2sn 459 20 N N NNP cord-276598-tm0yj2sn 459 21 ) ) -RRB- cord-276598-tm0yj2sn 459 22 from from IN cord-276598-tm0yj2sn 459 23 aldehydes aldehyde NNS cord-276598-tm0yj2sn 459 24 and and CC cord-276598-tm0yj2sn 459 25 phosphoryl phosphoryl NN cord-276598-tm0yj2sn 459 26 azide azide NN cord-276598-tm0yj2sn 459 27 through through IN cord-276598-tm0yj2sn 459 28 nitrene nitrene JJ cord-276598-tm0yj2sn 459 29 insertion insertion NN cord-276598-tm0yj2sn 459 30 ( ( -LRB- cord-276598-tm0yj2sn 459 31 Scheme scheme NN cord-276598-tm0yj2sn 459 32 10b 10b CD cord-276598-tm0yj2sn 459 33 ) ) -RRB- cord-276598-tm0yj2sn 459 34 [ [ -LRB- cord-276598-tm0yj2sn 459 35 113 113 CD cord-276598-tm0yj2sn 459 36 ] ] -RRB- cord-276598-tm0yj2sn 459 37 . . . cord-276598-tm0yj2sn 460 1 The the DT cord-276598-tm0yj2sn 460 2 product product NN cord-276598-tm0yj2sn 460 3 was be VBD cord-276598-tm0yj2sn 460 4 isolated isolate VBN cord-276598-tm0yj2sn 460 5 by by IN cord-276598-tm0yj2sn 460 6 column column NN cord-276598-tm0yj2sn 460 7 chromatography chromatography NN cord-276598-tm0yj2sn 460 8 ( ( -LRB- cord-276598-tm0yj2sn 460 9 on on IN cord-276598-tm0yj2sn 460 10 silica silica NN cord-276598-tm0yj2sn 460 11 ) ) -RRB- cord-276598-tm0yj2sn 460 12 . . . cord-276598-tm0yj2sn 461 1 The the DT cord-276598-tm0yj2sn 461 2 observed observed JJ cord-276598-tm0yj2sn 461 3 product product NN cord-276598-tm0yj2sn 461 4 conversions conversion NNS cord-276598-tm0yj2sn 461 5 were be VBD cord-276598-tm0yj2sn 461 6 in in IN cord-276598-tm0yj2sn 461 7 the the DT cord-276598-tm0yj2sn 461 8 range range NN cord-276598-tm0yj2sn 461 9 56 56 CD cord-276598-tm0yj2sn 461 10 - - SYM cord-276598-tm0yj2sn 461 11 99 99 CD cord-276598-tm0yj2sn 461 12 % % NN cord-276598-tm0yj2sn 461 13 . . . cord-276598-tm0yj2sn 462 1 Aromatic aromatic JJ cord-276598-tm0yj2sn 462 2 and and CC cord-276598-tm0yj2sn 462 3 aliphatic aliphatic JJ cord-276598-tm0yj2sn 462 4 aldehydes aldehyde NNS cord-276598-tm0yj2sn 462 5 such such JJ cord-276598-tm0yj2sn 462 6 as as IN cord-276598-tm0yj2sn 462 7 2-naphthaldehyde 2-naphthaldehyde CD cord-276598-tm0yj2sn 462 8 , , , cord-276598-tm0yj2sn 462 9 benzo[d benzo[d NNP cord-276598-tm0yj2sn 462 10 ] ] -RRB- cord-276598-tm0yj2sn 463 1 [ [ -LRB- cord-276598-tm0yj2sn 463 2 1 1 CD cord-276598-tm0yj2sn 463 3 , , , cord-276598-tm0yj2sn 463 4 3 3 CD cord-276598-tm0yj2sn 463 5 ] ] -RRB- cord-276598-tm0yj2sn 463 6 dioxole-5-carbaldehyde dioxole-5-carbaldehyde NNP cord-276598-tm0yj2sn 463 7 , , , cord-276598-tm0yj2sn 463 8 5,6-dihydro-2H 5,6-dihydro-2h CD cord-276598-tm0yj2sn 463 9 - - : cord-276598-tm0yj2sn 463 10 pyran-3-carbaldehyde pyran-3-carbaldehyde NNP cord-276598-tm0yj2sn 463 11 and and CC cord-276598-tm0yj2sn 463 12 3-methylbut-2-enal 3-methylbut-2-enal CD cord-276598-tm0yj2sn 463 13 were be VBD cord-276598-tm0yj2sn 463 14 used use VBN cord-276598-tm0yj2sn 463 15 in in IN cord-276598-tm0yj2sn 463 16 the the DT cord-276598-tm0yj2sn 463 17 reaction reaction NN cord-276598-tm0yj2sn 463 18 along along IN cord-276598-tm0yj2sn 463 19 with with IN cord-276598-tm0yj2sn 463 20 aromatic aromatic JJ cord-276598-tm0yj2sn 463 21 and and CC cord-276598-tm0yj2sn 463 22 aliphatic aliphatic JJ cord-276598-tm0yj2sn 463 23 phosphoryl phosphoryl NNS cord-276598-tm0yj2sn 463 24 azide azide NN cord-276598-tm0yj2sn 463 25 such such JJ cord-276598-tm0yj2sn 463 26 as as IN cord-276598-tm0yj2sn 463 27 3-nitrophenyl 3-nitrophenyl CD cord-276598-tm0yj2sn 464 1 ( ( -LRB- cord-276598-tm0yj2sn 464 2 4-nitrophenyl 4-nitrophenyl CD cord-276598-tm0yj2sn 464 3 ) ) -RRB- cord-276598-tm0yj2sn 464 4 phosphorazidate phosphorazidate NNP cord-276598-tm0yj2sn 464 5 , , , cord-276598-tm0yj2sn 464 6 bis(2,2,2-trichloroethyl bis(2,2,2-trichloroethyl NNP cord-276598-tm0yj2sn 464 7 ) ) -RRB- cord-276598-tm0yj2sn 464 8 phosphorazidate phosphorazidate NNP cord-276598-tm0yj2sn 464 9 , , , cord-276598-tm0yj2sn 464 10 and and CC cord-276598-tm0yj2sn 464 11 diethyl diethyl NNP cord-276598-tm0yj2sn 464 12 phosphorazidate phosphorazidate NNP cord-276598-tm0yj2sn 464 13 . . . cord-276598-tm0yj2sn 465 1 However however RB cord-276598-tm0yj2sn 465 2 , , , cord-276598-tm0yj2sn 465 3 lower low JJR cord-276598-tm0yj2sn 465 4 yields yield NNS cord-276598-tm0yj2sn 465 5 were be VBD cord-276598-tm0yj2sn 465 6 obtained obtain VBN cord-276598-tm0yj2sn 465 7 from from IN cord-276598-tm0yj2sn 465 8 aliphatic aliphatic JJ cord-276598-tm0yj2sn 465 9 aldehydes aldehyde NNS cord-276598-tm0yj2sn 465 10 when when WRB cord-276598-tm0yj2sn 465 11 compared compare VBN cord-276598-tm0yj2sn 465 12 with with IN cord-276598-tm0yj2sn 465 13 the the DT cord-276598-tm0yj2sn 465 14 aromatic aromatic JJ cord-276598-tm0yj2sn 465 15 aldehydes aldehyde NNS cord-276598-tm0yj2sn 465 16 , , , cord-276598-tm0yj2sn 465 17 suggesting suggest VBG cord-276598-tm0yj2sn 465 18 that that IN cord-276598-tm0yj2sn 465 19 the the DT cord-276598-tm0yj2sn 465 20 synthetic synthetic JJ cord-276598-tm0yj2sn 465 21 procedure procedure NN cord-276598-tm0yj2sn 465 22 favors favor VBZ cord-276598-tm0yj2sn 465 23 electron electron NN cord-276598-tm0yj2sn 465 24 - - HYPH cord-276598-tm0yj2sn 465 25 rich rich JJ cord-276598-tm0yj2sn 465 26 aromatic aromatic JJ cord-276598-tm0yj2sn 465 27 aldehydes aldehyde NNS cord-276598-tm0yj2sn 465 28 . . . cord-276598-tm0yj2sn 466 1 A a DT cord-276598-tm0yj2sn 466 2 nitrene nitrene JJ cord-276598-tm0yj2sn 466 3 insertion insertion NN cord-276598-tm0yj2sn 466 4 route route NN cord-276598-tm0yj2sn 466 5 in in IN cord-276598-tm0yj2sn 466 6 the the DT cord-276598-tm0yj2sn 466 7 presence presence NN cord-276598-tm0yj2sn 466 8 of of IN cord-276598-tm0yj2sn 466 9 Ir(III)-based Ir(III)-based NNP cord-276598-tm0yj2sn 466 10 catalyst catalyst NN cord-276598-tm0yj2sn 466 11 was be VBD cord-276598-tm0yj2sn 466 12 also also RB cord-276598-tm0yj2sn 466 13 used use VBN cord-276598-tm0yj2sn 466 14 to to TO cord-276598-tm0yj2sn 466 15 synthesize synthesize VB cord-276598-tm0yj2sn 466 16 P p NN cord-276598-tm0yj2sn 466 17 - - HYPH cord-276598-tm0yj2sn 466 18 Ns Ns NNP cord-276598-tm0yj2sn 466 19 by by IN cord-276598-tm0yj2sn 466 20 Zhu Zhu NNP cord-276598-tm0yj2sn 466 21 et et FW cord-276598-tm0yj2sn 466 22 al al NNP cord-276598-tm0yj2sn 466 23 . . . cord-276598-tm0yj2sn 467 1 ( ( -LRB- cord-276598-tm0yj2sn 467 2 Scheme scheme NN cord-276598-tm0yj2sn 467 3 10c 10c CD cord-276598-tm0yj2sn 467 4 ) ) -RRB- cord-276598-tm0yj2sn 468 1 [ [ -LRB- cord-276598-tm0yj2sn 468 2 114 114 CD cord-276598-tm0yj2sn 468 3 ] ] -RRB- cord-276598-tm0yj2sn 468 4 . . . cord-276598-tm0yj2sn 469 1 The the DT cord-276598-tm0yj2sn 469 2 P P NNP cord-276598-tm0yj2sn 469 3 - - HYPH cord-276598-tm0yj2sn 469 4 Ns Ns NNP cord-276598-tm0yj2sn 469 5 were be VBD cord-276598-tm0yj2sn 469 6 synthesized synthesize VBN cord-276598-tm0yj2sn 469 7 under under IN cord-276598-tm0yj2sn 469 8 an an DT cord-276598-tm0yj2sn 469 9 inert inert JJ cord-276598-tm0yj2sn 469 10 environment environment NN cord-276598-tm0yj2sn 469 11 and and CC cord-276598-tm0yj2sn 469 12 the the DT cord-276598-tm0yj2sn 469 13 isolated isolated JJ cord-276598-tm0yj2sn 469 14 yield yield NN cord-276598-tm0yj2sn 469 15 of of IN cord-276598-tm0yj2sn 469 16 the the DT cord-276598-tm0yj2sn 469 17 products product NNS cord-276598-tm0yj2sn 469 18 was be VBD cord-276598-tm0yj2sn 469 19 in in IN cord-276598-tm0yj2sn 469 20 the the DT cord-276598-tm0yj2sn 469 21 range range NN cord-276598-tm0yj2sn 469 22 of of IN cord-276598-tm0yj2sn 469 23 52 52 CD cord-276598-tm0yj2sn 469 24 - - SYM cord-276598-tm0yj2sn 469 25 77 77 CD cord-276598-tm0yj2sn 469 26 % % NN cord-276598-tm0yj2sn 469 27 . . . cord-276598-tm0yj2sn 470 1 The the DT cord-276598-tm0yj2sn 470 2 scope scope NN cord-276598-tm0yj2sn 470 3 of of IN cord-276598-tm0yj2sn 470 4 the the DT cord-276598-tm0yj2sn 470 5 synthesis synthesis NN cord-276598-tm0yj2sn 470 6 was be VBD cord-276598-tm0yj2sn 470 7 investigated investigate VBN cord-276598-tm0yj2sn 470 8 using use VBG cord-276598-tm0yj2sn 470 9 diethyl diethyl NNP cord-276598-tm0yj2sn 470 10 phosphorazidate phosphorazidate NN cord-276598-tm0yj2sn 470 11 and and CC cord-276598-tm0yj2sn 470 12 diphenyl diphenyl NNP cord-276598-tm0yj2sn 470 13 phosphorazidate phosphorazidate VB cord-276598-tm0yj2sn 470 14 along along IN cord-276598-tm0yj2sn 470 15 with with IN cord-276598-tm0yj2sn 470 16 2-phenylpyridine 2-phenylpyridine CD cord-276598-tm0yj2sn 470 17 or or CC cord-276598-tm0yj2sn 470 18 pyrazole pyrazole NN cord-276598-tm0yj2sn 470 19 derivatives derivative NNS cord-276598-tm0yj2sn 470 20 with with IN cord-276598-tm0yj2sn 470 21 substituents substituent NNS cord-276598-tm0yj2sn 470 22 such such JJ cord-276598-tm0yj2sn 470 23 as as IN cord-276598-tm0yj2sn 470 24 Me -PRON- PRP cord-276598-tm0yj2sn 470 25 , , , cord-276598-tm0yj2sn 470 26 OMe OMe NNS cord-276598-tm0yj2sn 470 27 , , , cord-276598-tm0yj2sn 470 28 CF CF NNP cord-276598-tm0yj2sn 470 29 3 3 CD cord-276598-tm0yj2sn 470 30 , , , cord-276598-tm0yj2sn 470 31 Cl Cl NNP cord-276598-tm0yj2sn 470 32 , , , cord-276598-tm0yj2sn 470 33 F F NNP cord-276598-tm0yj2sn 470 34 , , , cord-276598-tm0yj2sn 470 35 Ph Ph NNP cord-276598-tm0yj2sn 470 36 , , , cord-276598-tm0yj2sn 470 37 and and CC cord-276598-tm0yj2sn 470 38 COOMe COOMe NNPS cord-276598-tm0yj2sn 470 39 at at IN cord-276598-tm0yj2sn 470 40 ortho- ortho- NN cord-276598-tm0yj2sn 470 41 , , , cord-276598-tm0yj2sn 470 42 meta- meta- NN cord-276598-tm0yj2sn 470 43 , , , cord-276598-tm0yj2sn 470 44 and and CC cord-276598-tm0yj2sn 470 45 para para NN cord-276598-tm0yj2sn 470 46 - - HYPH cord-276598-tm0yj2sn 470 47 positions position NNS cord-276598-tm0yj2sn 470 48 as as RB cord-276598-tm0yj2sn 470 49 well well RB cord-276598-tm0yj2sn 470 50 as as IN cord-276598-tm0yj2sn 470 51 benzo[h]quinoline benzo[h]quinoline NNP cord-276598-tm0yj2sn 470 52 . . . cord-276598-tm0yj2sn 471 1 Although although IN cord-276598-tm0yj2sn 471 2 nitrene nitrene JJ cord-276598-tm0yj2sn 471 3 insertion insertion NN cord-276598-tm0yj2sn 471 4 provides provide VBZ cord-276598-tm0yj2sn 471 5 a a DT cord-276598-tm0yj2sn 471 6 viable viable JJ cord-276598-tm0yj2sn 471 7 route route NN cord-276598-tm0yj2sn 471 8 to to IN cord-276598-tm0yj2sn 471 9 P p NN cord-276598-tm0yj2sn 471 10 - - HYPH cord-276598-tm0yj2sn 471 11 N n CD cord-276598-tm0yj2sn 471 12 synthesis synthesis NN cord-276598-tm0yj2sn 471 13 and and CC cord-276598-tm0yj2sn 471 14 generates generate VBZ cord-276598-tm0yj2sn 471 15 N n CD cord-276598-tm0yj2sn 471 16 2 2 CD cord-276598-tm0yj2sn 471 17 gas gas NN cord-276598-tm0yj2sn 471 18 as as IN cord-276598-tm0yj2sn 471 19 the the DT cord-276598-tm0yj2sn 471 20 only only JJ cord-276598-tm0yj2sn 471 21 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 471 22 by by IN cord-276598-tm0yj2sn 471 23 - - HYPH cord-276598-tm0yj2sn 471 24 product product NN cord-276598-tm0yj2sn 471 25 , , , cord-276598-tm0yj2sn 471 26 the the DT cord-276598-tm0yj2sn 471 27 process process NN cord-276598-tm0yj2sn 471 28 uses use VBZ cord-276598-tm0yj2sn 471 29 expensive expensive JJ cord-276598-tm0yj2sn 471 30 catalysts catalyst NNS cord-276598-tm0yj2sn 471 31 in in IN cord-276598-tm0yj2sn 471 32 addition addition NN cord-276598-tm0yj2sn 471 33 to to IN cord-276598-tm0yj2sn 471 34 many many JJ cord-276598-tm0yj2sn 471 35 chemical chemical JJ cord-276598-tm0yj2sn 471 36 additives additive NNS cord-276598-tm0yj2sn 471 37 . . . cord-276598-tm0yj2sn 472 1 Moreover moreover RB cord-276598-tm0yj2sn 472 2 , , , cord-276598-tm0yj2sn 472 3 apart apart RB cord-276598-tm0yj2sn 472 4 from from IN cord-276598-tm0yj2sn 472 5 the the DT cord-276598-tm0yj2sn 472 6 hazards hazard NNS cord-276598-tm0yj2sn 472 7 associated associate VBN cord-276598-tm0yj2sn 472 8 with with IN cord-276598-tm0yj2sn 472 9 the the DT cord-276598-tm0yj2sn 472 10 handling handling NN cord-276598-tm0yj2sn 472 11 of of IN cord-276598-tm0yj2sn 472 12 phosphoryl phosphoryl NNS cord-276598-tm0yj2sn 472 13 azide azide NN cord-276598-tm0yj2sn 472 14 , , , cord-276598-tm0yj2sn 472 15 the the DT cord-276598-tm0yj2sn 472 16 route route NN cord-276598-tm0yj2sn 472 17 requires require VBZ cord-276598-tm0yj2sn 472 18 a a DT cord-276598-tm0yj2sn 472 19 long long JJ cord-276598-tm0yj2sn 472 20 reaction reaction NN cord-276598-tm0yj2sn 472 21 time time NN cord-276598-tm0yj2sn 472 22 , , , cord-276598-tm0yj2sn 472 23 high high JJ cord-276598-tm0yj2sn 472 24 temperature temperature NN cord-276598-tm0yj2sn 472 25 , , , cord-276598-tm0yj2sn 472 26 and and CC cord-276598-tm0yj2sn 472 27 does do VBZ cord-276598-tm0yj2sn 472 28 not not RB cord-276598-tm0yj2sn 472 29 favor favor VB cord-276598-tm0yj2sn 472 30 electron electron NN cord-276598-tm0yj2sn 472 31 - - HYPH cord-276598-tm0yj2sn 472 32 deficient deficient JJ cord-276598-tm0yj2sn 472 33 starting starting NN cord-276598-tm0yj2sn 472 34 materials material NNS cord-276598-tm0yj2sn 472 35 . . . cord-276598-tm0yj2sn 473 1 An an DT cord-276598-tm0yj2sn 473 2 organic organic JJ cord-276598-tm0yj2sn 473 3 azide azide NN cord-276598-tm0yj2sn 473 4 was be VBD cord-276598-tm0yj2sn 473 5 generated generate VBN cord-276598-tm0yj2sn 473 6 in in IN cord-276598-tm0yj2sn 473 7 situ situ NN cord-276598-tm0yj2sn 473 8 from from IN cord-276598-tm0yj2sn 473 9 organic organic JJ cord-276598-tm0yj2sn 473 10 halides halide NNS cord-276598-tm0yj2sn 473 11 and and CC cord-276598-tm0yj2sn 473 12 was be VBD cord-276598-tm0yj2sn 473 13 coupled couple VBN cord-276598-tm0yj2sn 473 14 with with IN cord-276598-tm0yj2sn 473 15 ( ( -LRB- cord-276598-tm0yj2sn 473 16 RO ro NN cord-276598-tm0yj2sn 473 17 ) ) -RRB- cord-276598-tm0yj2sn 473 18 3 3 CD cord-276598-tm0yj2sn 473 19 P p NN cord-276598-tm0yj2sn 473 20 ( ( -LRB- cord-276598-tm0yj2sn 473 21 R r NN cord-276598-tm0yj2sn 473 22 = = NN cord-276598-tm0yj2sn 473 23 alkyl alkyl NN cord-276598-tm0yj2sn 473 24 ) ) -RRB- cord-276598-tm0yj2sn 473 25 for for IN cord-276598-tm0yj2sn 473 26 the the DT cord-276598-tm0yj2sn 473 27 synthesis synthesis NN cord-276598-tm0yj2sn 473 28 of of IN cord-276598-tm0yj2sn 473 29 P P NNP cord-276598-tm0yj2sn 473 30 - - HYPH cord-276598-tm0yj2sn 473 31 N N NNP cord-276598-tm0yj2sn 473 32 by by IN cord-276598-tm0yj2sn 473 33 Sangwan Sangwan NNP cord-276598-tm0yj2sn 473 34 et et NNP cord-276598-tm0yj2sn 473 35 al al NNP cord-276598-tm0yj2sn 473 36 . . . cord-276598-tm0yj2sn 474 1 ( ( -LRB- cord-276598-tm0yj2sn 474 2 Scheme scheme NN cord-276598-tm0yj2sn 474 3 11 11 CD cord-276598-tm0yj2sn 474 4 ) ) -RRB- cord-276598-tm0yj2sn 475 1 The the DT cord-276598-tm0yj2sn 475 2 crude crude JJ cord-276598-tm0yj2sn 475 3 product product NN cord-276598-tm0yj2sn 475 4 was be VBD cord-276598-tm0yj2sn 475 5 purified purify VBN cord-276598-tm0yj2sn 475 6 by by IN cord-276598-tm0yj2sn 475 7 column column NN cord-276598-tm0yj2sn 475 8 chromatography chromatography NN cord-276598-tm0yj2sn 475 9 ( ( -LRB- cord-276598-tm0yj2sn 475 10 on on IN cord-276598-tm0yj2sn 475 11 silica silica NN cord-276598-tm0yj2sn 475 12 ) ) -RRB- cord-276598-tm0yj2sn 475 13 to to TO cord-276598-tm0yj2sn 475 14 afford afford VB cord-276598-tm0yj2sn 475 15 isolated isolated JJ cord-276598-tm0yj2sn 475 16 products product NNS cord-276598-tm0yj2sn 475 17 in in IN cord-276598-tm0yj2sn 475 18 the the DT cord-276598-tm0yj2sn 475 19 range range NN cord-276598-tm0yj2sn 475 20 of of IN cord-276598-tm0yj2sn 475 21 52 52 CD cord-276598-tm0yj2sn 475 22 - - SYM cord-276598-tm0yj2sn 475 23 96 96 CD cord-276598-tm0yj2sn 475 24 % % NN cord-276598-tm0yj2sn 475 25 yield yield NN cord-276598-tm0yj2sn 475 26 . . . cord-276598-tm0yj2sn 476 1 A a DT cord-276598-tm0yj2sn 476 2 broad broad JJ cord-276598-tm0yj2sn 476 3 scope scope NN cord-276598-tm0yj2sn 476 4 of of IN cord-276598-tm0yj2sn 476 5 the the DT cord-276598-tm0yj2sn 476 6 reaction reaction NN cord-276598-tm0yj2sn 476 7 was be VBD cord-276598-tm0yj2sn 476 8 tested test VBN cord-276598-tm0yj2sn 476 9 ; ; : cord-276598-tm0yj2sn 476 10 3-bromoprop-1-yne 3-bromoprop-1-yne NN cord-276598-tm0yj2sn 476 11 , , , cord-276598-tm0yj2sn 476 12 3-bromoprop-1-ene 3-bromoprop-1-ene CD cord-276598-tm0yj2sn 476 13 , , , cord-276598-tm0yj2sn 476 14 1-bromopropane 1-bromopropane CD cord-276598-tm0yj2sn 476 15 alkyl alkyl NN cord-276598-tm0yj2sn 476 16 or or CC cord-276598-tm0yj2sn 476 17 ( ( -LRB- cord-276598-tm0yj2sn 476 18 un)substituted un)substitute VBN cord-276598-tm0yj2sn 476 19 aromatic aromatic JJ cord-276598-tm0yj2sn 476 20 halide halide NN cord-276598-tm0yj2sn 476 21 such such JJ cord-276598-tm0yj2sn 476 22 as as IN cord-276598-tm0yj2sn 476 23 ( ( -LRB- cord-276598-tm0yj2sn 476 24 bromomethyl)benzene bromomethyl)benzene NNP cord-276598-tm0yj2sn 476 25 , , , cord-276598-tm0yj2sn 476 26 1-(bromomethyl)-2-nitrobenzene 1-(bromomethyl)-2-nitrobenzene CD cord-276598-tm0yj2sn 476 27 , , , cord-276598-tm0yj2sn 476 28 1-(chloromethyl)-4-nitrobenzene 1-(chloromethyl)-4-nitrobenzene CD cord-276598-tm0yj2sn 476 29 , , , cord-276598-tm0yj2sn 476 30 ( ( -LRB- cord-276598-tm0yj2sn 476 31 chloromethyl)benzene chloromethyl)benzene NNP cord-276598-tm0yj2sn 476 32 , , , cord-276598-tm0yj2sn 476 33 1-(bromomethyl)-3,5-dimethoxybenzene 1-(bromomethyl)-3,5-dimethoxybenzene CD cord-276598-tm0yj2sn 476 34 , , , cord-276598-tm0yj2sn 476 35 or or CC cord-276598-tm0yj2sn 476 36 3-(4-(bromomethyl)-1H-1,2,3-triazol-1-yl)benzyl 3-(4-(bromomethyl)-1h-1,2,3-triazol-1-yl)benzyl CD cord-276598-tm0yj2sn 476 37 acetate acetate NN cord-276598-tm0yj2sn 476 38 were be VBD cord-276598-tm0yj2sn 476 39 reacted react VBN cord-276598-tm0yj2sn 476 40 with with IN cord-276598-tm0yj2sn 476 41 dimethyl dimethyl NN cord-276598-tm0yj2sn 476 42 or or CC cord-276598-tm0yj2sn 476 43 diethyl diethyl NN cord-276598-tm0yj2sn 476 44 H H NNP cord-276598-tm0yj2sn 476 45 - - HYPH cord-276598-tm0yj2sn 476 46 P. P. NNP cord-276598-tm0yj2sn 476 47 1-(chloromethyl)-4-nitrobenzene 1-(chloromethyl)-4-nitrobenzene CD cord-276598-tm0yj2sn 476 48 , , , cord-276598-tm0yj2sn 476 49 ( ( -LRB- cord-276598-tm0yj2sn 476 50 chloromethyl)benzene chloromethyl)benzene NNP cord-276598-tm0yj2sn 476 51 , , , cord-276598-tm0yj2sn 476 52 1-(bromomethyl)-3,5-dimethoxybenzene 1-(bromomethyl)-3,5-dimethoxybenzene CD cord-276598-tm0yj2sn 476 53 , , , cord-276598-tm0yj2sn 476 54 or or CC cord-276598-tm0yj2sn 476 55 3-(4-(bromomethyl)-1H-1,2,3-triazol-1-yl)benzyl 3-(4-(bromomethyl)-1h-1,2,3-triazol-1-yl)benzyl CD cord-276598-tm0yj2sn 476 56 acetate acetate NN cord-276598-tm0yj2sn 476 57 were be VBD cord-276598-tm0yj2sn 476 58 reacted react VBN cord-276598-tm0yj2sn 476 59 with with IN cord-276598-tm0yj2sn 476 60 dimethyl dimethyl NN cord-276598-tm0yj2sn 476 61 or or CC cord-276598-tm0yj2sn 476 62 diethyl diethyl NN cord-276598-tm0yj2sn 476 63 H h NN cord-276598-tm0yj2sn 477 1 -P. -P. : cord-276598-tm0yj2sn 477 2 A a DT cord-276598-tm0yj2sn 477 3 similar similar JJ cord-276598-tm0yj2sn 477 4 method method NN cord-276598-tm0yj2sn 477 5 of of IN cord-276598-tm0yj2sn 477 6 P p NN cord-276598-tm0yj2sn 477 7 - - HYPH cord-276598-tm0yj2sn 477 8 N n CD cord-276598-tm0yj2sn 477 9 synthesis synthesis NN cord-276598-tm0yj2sn 477 10 via via IN cord-276598-tm0yj2sn 477 11 in in IN cord-276598-tm0yj2sn 477 12 situ situ NN cord-276598-tm0yj2sn 477 13 azide azide NN cord-276598-tm0yj2sn 477 14 generation generation NN cord-276598-tm0yj2sn 477 15 from from IN cord-276598-tm0yj2sn 477 16 organic organic JJ cord-276598-tm0yj2sn 477 17 halides halide NNS cord-276598-tm0yj2sn 477 18 was be VBD cord-276598-tm0yj2sn 477 19 reported report VBN cord-276598-tm0yj2sn 477 20 by by IN cord-276598-tm0yj2sn 477 21 Dar Dar NNP cord-276598-tm0yj2sn 477 22 [ [ -LRB- cord-276598-tm0yj2sn 477 23 115 115 CD cord-276598-tm0yj2sn 477 24 ] ] -RRB- cord-276598-tm0yj2sn 477 25 , , , cord-276598-tm0yj2sn 477 26 following follow VBG cord-276598-tm0yj2sn 477 27 the the DT cord-276598-tm0yj2sn 477 28 procedure procedure NN cord-276598-tm0yj2sn 477 29 previously previously RB cord-276598-tm0yj2sn 477 30 reported report VBN cord-276598-tm0yj2sn 477 31 by by IN cord-276598-tm0yj2sn 477 32 Sangwan Sangwan NNP cord-276598-tm0yj2sn 477 33 et et NNP cord-276598-tm0yj2sn 477 34 al al NNP cord-276598-tm0yj2sn 477 35 . . . cord-276598-tm0yj2sn 478 1 ( ( -LRB- cord-276598-tm0yj2sn 478 2 Scheme scheme NN cord-276598-tm0yj2sn 478 3 11 11 CD cord-276598-tm0yj2sn 478 4 ) ) -RRB- cord-276598-tm0yj2sn 478 5 [ [ -LRB- cord-276598-tm0yj2sn 478 6 116 116 CD cord-276598-tm0yj2sn 478 7 ] ] -RRB- cord-276598-tm0yj2sn 478 8 . . . cord-276598-tm0yj2sn 479 1 The the DT cord-276598-tm0yj2sn 479 2 yield yield NN cord-276598-tm0yj2sn 479 3 range range NN cord-276598-tm0yj2sn 479 4 of of IN cord-276598-tm0yj2sn 479 5 the the DT cord-276598-tm0yj2sn 479 6 isolated isolate VBN cord-276598-tm0yj2sn 479 7 P p NN cord-276598-tm0yj2sn 479 8 - - HYPH cord-276598-tm0yj2sn 479 9 Ns Ns NNP cord-276598-tm0yj2sn 479 10 , , , cord-276598-tm0yj2sn 479 11 in in IN cord-276598-tm0yj2sn 479 12 this this DT cord-276598-tm0yj2sn 479 13 case case NN cord-276598-tm0yj2sn 479 14 , , , cord-276598-tm0yj2sn 479 15 was be VBD cord-276598-tm0yj2sn 479 16 60 60 CD cord-276598-tm0yj2sn 479 17 - - SYM cord-276598-tm0yj2sn 479 18 96 96 CD cord-276598-tm0yj2sn 479 19 % % NN cord-276598-tm0yj2sn 479 20 . . . cord-276598-tm0yj2sn 480 1 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 480 2 - - HYPH cord-276598-tm0yj2sn 480 3 derived derive VBN cord-276598-tm0yj2sn 480 4 bioactive bioactive JJ cord-276598-tm0yj2sn 480 5 compound compound NN cord-276598-tm0yj2sn 480 6 ( ( -LRB- cord-276598-tm0yj2sn 480 7 19 19 CD cord-276598-tm0yj2sn 480 8 ) ) -RRB- cord-276598-tm0yj2sn 480 9 was be VBD cord-276598-tm0yj2sn 480 10 synthesized synthesize VBN cord-276598-tm0yj2sn 480 11 using use VBG cord-276598-tm0yj2sn 480 12 the the DT cord-276598-tm0yj2sn 480 13 proposed propose VBN cord-276598-tm0yj2sn 480 14 method method NN cord-276598-tm0yj2sn 480 15 ( ( -LRB- cord-276598-tm0yj2sn 480 16 Figure figure NN cord-276598-tm0yj2sn 480 17 9 9 CD cord-276598-tm0yj2sn 480 18 ) ) -RRB- cord-276598-tm0yj2sn 480 19 . . . cord-276598-tm0yj2sn 481 1 Scheme scheme NN cord-276598-tm0yj2sn 481 2 11 11 CD cord-276598-tm0yj2sn 481 3 . . . cord-276598-tm0yj2sn 482 1 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 482 2 synthesis synthesis NN cord-276598-tm0yj2sn 482 3 from from IN cord-276598-tm0yj2sn 482 4 organic organic JJ cord-276598-tm0yj2sn 482 5 azide azide NN cord-276598-tm0yj2sn 482 6 and and CC cord-276598-tm0yj2sn 482 7 ( ( -LRB- cord-276598-tm0yj2sn 482 8 RO)3P. ro)3p. IN cord-276598-tm0yj2sn 482 9 Figure figure NN cord-276598-tm0yj2sn 482 10 9 9 CD cord-276598-tm0yj2sn 482 11 . . . cord-276598-tm0yj2sn 483 1 Structure structure NN cord-276598-tm0yj2sn 483 2 of of IN cord-276598-tm0yj2sn 483 3 ( ( -LRB- cord-276598-tm0yj2sn 483 4 1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 1r,2s,5r)-2-isopropyl-5-methylcyclohexyl CD cord-276598-tm0yj2sn 483 5 ( ( -LRB- cord-276598-tm0yj2sn 483 6 dimethoxyphosphoryl)glycinate dimethoxyphosphoryl)glycinate NNP cord-276598-tm0yj2sn 483 7 ( ( -LRB- cord-276598-tm0yj2sn 483 8 19 19 CD cord-276598-tm0yj2sn 483 9 ) ) -RRB- cord-276598-tm0yj2sn 483 10 synthesized synthesize VBN cord-276598-tm0yj2sn 483 11 via via IN cord-276598-tm0yj2sn 483 12 in in IN cord-276598-tm0yj2sn 483 13 situ situ NN cord-276598-tm0yj2sn 483 14 azide azide NN cord-276598-tm0yj2sn 483 15 generation generation NN cord-276598-tm0yj2sn 483 16 . . . cord-276598-tm0yj2sn 484 1 In in IN cord-276598-tm0yj2sn 484 2 1988 1988 CD cord-276598-tm0yj2sn 484 3 , , , cord-276598-tm0yj2sn 484 4 Koziara Koziara NNP cord-276598-tm0yj2sn 484 5 reported report VBD cord-276598-tm0yj2sn 484 6 a a DT cord-276598-tm0yj2sn 484 7 two two CD cord-276598-tm0yj2sn 484 8 - - HYPH cord-276598-tm0yj2sn 484 9 step step NN cord-276598-tm0yj2sn 484 10 P p NN cord-276598-tm0yj2sn 484 11 - - HYPH cord-276598-tm0yj2sn 484 12 N n CD cord-276598-tm0yj2sn 484 13 synthetic synthetic JJ cord-276598-tm0yj2sn 484 14 route route NN cord-276598-tm0yj2sn 484 15 via via IN cord-276598-tm0yj2sn 484 16 organic organic JJ cord-276598-tm0yj2sn 484 17 azide azide NN cord-276598-tm0yj2sn 484 18 generation generation NN cord-276598-tm0yj2sn 484 19 using use VBG cord-276598-tm0yj2sn 484 20 a a DT cord-276598-tm0yj2sn 484 21 [ [ -LRB- cord-276598-tm0yj2sn 484 22 n n NNP cord-276598-tm0yj2sn 484 23 - - HYPH cord-276598-tm0yj2sn 484 24 Bu4N]Br Bu4N]Br NNP cord-276598-tm0yj2sn 484 25 catalyst catalyst NN cord-276598-tm0yj2sn 484 26 ( ( -LRB- cord-276598-tm0yj2sn 484 27 Scheme scheme NN cord-276598-tm0yj2sn 484 28 12 12 CD cord-276598-tm0yj2sn 484 29 ) ) -RRB- cord-276598-tm0yj2sn 484 30 [ [ -LRB- cord-276598-tm0yj2sn 484 31 93 93 CD cord-276598-tm0yj2sn 484 32 ] ] -RRB- cord-276598-tm0yj2sn 484 33 . . . cord-276598-tm0yj2sn 485 1 The the DT cord-276598-tm0yj2sn 485 2 crude crude JJ cord-276598-tm0yj2sn 485 3 product product NN cord-276598-tm0yj2sn 485 4 was be VBD cord-276598-tm0yj2sn 485 5 purified purify VBN cord-276598-tm0yj2sn 485 6 by by IN cord-276598-tm0yj2sn 485 7 crystallization crystallization NN cord-276598-tm0yj2sn 485 8 or or CC cord-276598-tm0yj2sn 485 9 vacuum vacuum NN cord-276598-tm0yj2sn 485 10 distillation distillation NN cord-276598-tm0yj2sn 485 11 with with IN cord-276598-tm0yj2sn 485 12 50 50 CD cord-276598-tm0yj2sn 485 13 - - SYM cord-276598-tm0yj2sn 485 14 93 93 CD cord-276598-tm0yj2sn 485 15 % % NN cord-276598-tm0yj2sn 485 16 isolated isolated JJ cord-276598-tm0yj2sn 485 17 yield yield NN cord-276598-tm0yj2sn 485 18 . . . cord-276598-tm0yj2sn 486 1 The the DT cord-276598-tm0yj2sn 486 2 organic organic JJ cord-276598-tm0yj2sn 486 3 halides halide NNS cord-276598-tm0yj2sn 486 4 used use VBN cord-276598-tm0yj2sn 486 5 were be VBD cord-276598-tm0yj2sn 486 6 ( ( -LRB- cord-276598-tm0yj2sn 486 7 3-bromopropyl)benzene 3-bromopropyl)benzene CD cord-276598-tm0yj2sn 486 8 , , , cord-276598-tm0yj2sn 486 9 ( ( -LRB- cord-276598-tm0yj2sn 486 10 2-bromoethyl)benzene 2-bromoethyl)benzene CD cord-276598-tm0yj2sn 486 11 , , , cord-276598-tm0yj2sn 486 12 1-bromohexane 1-bromohexane CD cord-276598-tm0yj2sn 486 13 , , , cord-276598-tm0yj2sn 486 14 bromocyclohexane bromocyclohexane NNP cord-276598-tm0yj2sn 486 15 , , , cord-276598-tm0yj2sn 486 16 1-bromobutane 1-bromobutane CD cord-276598-tm0yj2sn 486 17 , , , cord-276598-tm0yj2sn 486 18 or or CC cord-276598-tm0yj2sn 486 19 bromocyclopentane bromocyclopentane NNP cord-276598-tm0yj2sn 486 20 . . . cord-276598-tm0yj2sn 487 1 Routes route NNS cord-276598-tm0yj2sn 487 2 via via IN cord-276598-tm0yj2sn 487 3 organic organic JJ cord-276598-tm0yj2sn 487 4 azide azide NN cord-276598-tm0yj2sn 487 5 generation generation NN cord-276598-tm0yj2sn 487 6 use use NN cord-276598-tm0yj2sn 487 7 readily readily RB cord-276598-tm0yj2sn 487 8 available available JJ cord-276598-tm0yj2sn 487 9 , , , cord-276598-tm0yj2sn 487 10 less less RBR cord-276598-tm0yj2sn 487 11 toxic toxic JJ cord-276598-tm0yj2sn 487 12 organic organic JJ cord-276598-tm0yj2sn 487 13 halides halide NNS cord-276598-tm0yj2sn 488 1 and and CC cord-276598-tm0yj2sn 488 2 ( ( -LRB- cord-276598-tm0yj2sn 488 3 RO)3P RO)3P NNP cord-276598-tm0yj2sn 488 4 ( ( -LRB- cord-276598-tm0yj2sn 488 5 R r NN cord-276598-tm0yj2sn 488 6 = = NN cord-276598-tm0yj2sn 488 7 alkyl alkyl NN cord-276598-tm0yj2sn 488 8 ) ) -RRB- cord-276598-tm0yj2sn 488 9 relative relative JJ cord-276598-tm0yj2sn 488 10 to to IN cord-276598-tm0yj2sn 488 11 other other JJ cord-276598-tm0yj2sn 488 12 routes route NNS cord-276598-tm0yj2sn 488 13 and and CC cord-276598-tm0yj2sn 488 14 generate generate VB cord-276598-tm0yj2sn 488 15 N2 n2 NN cord-276598-tm0yj2sn 488 16 as as IN cord-276598-tm0yj2sn 488 17 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 488 18 waste waste NN cord-276598-tm0yj2sn 488 19 . . . cord-276598-tm0yj2sn 489 1 However however RB cord-276598-tm0yj2sn 489 2 , , , cord-276598-tm0yj2sn 489 3 the the DT cord-276598-tm0yj2sn 489 4 method method NN cord-276598-tm0yj2sn 489 5 Scheme scheme NN cord-276598-tm0yj2sn 489 6 11 11 CD cord-276598-tm0yj2sn 489 7 . . . cord-276598-tm0yj2sn 490 1 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 490 2 synthesis synthesis NN cord-276598-tm0yj2sn 490 3 from from IN cord-276598-tm0yj2sn 490 4 organic organic JJ cord-276598-tm0yj2sn 490 5 azide azide NN cord-276598-tm0yj2sn 490 6 and and CC cord-276598-tm0yj2sn 490 7 ( ( -LRB- cord-276598-tm0yj2sn 490 8 RO ro NN cord-276598-tm0yj2sn 490 9 ) ) -RRB- cord-276598-tm0yj2sn 491 1 3 3 CD cord-276598-tm0yj2sn 491 2 P. P. NNP cord-276598-tm0yj2sn 491 3 A a DT cord-276598-tm0yj2sn 491 4 similar similar JJ cord-276598-tm0yj2sn 491 5 method method NN cord-276598-tm0yj2sn 491 6 of of IN cord-276598-tm0yj2sn 491 7 P p NN cord-276598-tm0yj2sn 491 8 - - HYPH cord-276598-tm0yj2sn 491 9 N n CD cord-276598-tm0yj2sn 491 10 synthesis synthesis NN cord-276598-tm0yj2sn 491 11 via via IN cord-276598-tm0yj2sn 491 12 in in IN cord-276598-tm0yj2sn 491 13 situ situ NN cord-276598-tm0yj2sn 491 14 azide azide NN cord-276598-tm0yj2sn 491 15 generation generation NN cord-276598-tm0yj2sn 491 16 from from IN cord-276598-tm0yj2sn 491 17 organic organic JJ cord-276598-tm0yj2sn 491 18 halides halide NNS cord-276598-tm0yj2sn 491 19 was be VBD cord-276598-tm0yj2sn 491 20 reported report VBN cord-276598-tm0yj2sn 491 21 by by IN cord-276598-tm0yj2sn 491 22 Dar Dar NNP cord-276598-tm0yj2sn 491 23 [ [ -LRB- cord-276598-tm0yj2sn 491 24 115 115 CD cord-276598-tm0yj2sn 491 25 ] ] -RRB- cord-276598-tm0yj2sn 491 26 , , , cord-276598-tm0yj2sn 491 27 following follow VBG cord-276598-tm0yj2sn 491 28 the the DT cord-276598-tm0yj2sn 491 29 procedure procedure NN cord-276598-tm0yj2sn 491 30 previously previously RB cord-276598-tm0yj2sn 491 31 reported report VBN cord-276598-tm0yj2sn 491 32 by by IN cord-276598-tm0yj2sn 491 33 Sangwan Sangwan NNP cord-276598-tm0yj2sn 491 34 et et NNP cord-276598-tm0yj2sn 491 35 al al NNP cord-276598-tm0yj2sn 491 36 . . . cord-276598-tm0yj2sn 492 1 ( ( -LRB- cord-276598-tm0yj2sn 492 2 Scheme scheme NN cord-276598-tm0yj2sn 492 3 11 11 CD cord-276598-tm0yj2sn 492 4 ) ) -RRB- cord-276598-tm0yj2sn 492 5 [ [ -LRB- cord-276598-tm0yj2sn 492 6 116 116 CD cord-276598-tm0yj2sn 492 7 ] ] -RRB- cord-276598-tm0yj2sn 492 8 . . . cord-276598-tm0yj2sn 493 1 The the DT cord-276598-tm0yj2sn 493 2 yield yield NN cord-276598-tm0yj2sn 493 3 range range NN cord-276598-tm0yj2sn 493 4 of of IN cord-276598-tm0yj2sn 493 5 the the DT cord-276598-tm0yj2sn 493 6 isolated isolate VBN cord-276598-tm0yj2sn 493 7 P p NN cord-276598-tm0yj2sn 493 8 - - HYPH cord-276598-tm0yj2sn 493 9 Ns Ns NNP cord-276598-tm0yj2sn 493 10 , , , cord-276598-tm0yj2sn 493 11 in in IN cord-276598-tm0yj2sn 493 12 this this DT cord-276598-tm0yj2sn 493 13 case case NN cord-276598-tm0yj2sn 493 14 , , , cord-276598-tm0yj2sn 493 15 was be VBD cord-276598-tm0yj2sn 493 16 60 60 CD cord-276598-tm0yj2sn 493 17 - - SYM cord-276598-tm0yj2sn 493 18 96 96 CD cord-276598-tm0yj2sn 493 19 % % NN cord-276598-tm0yj2sn 493 20 . . . cord-276598-tm0yj2sn 494 1 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 494 2 - - HYPH cord-276598-tm0yj2sn 494 3 derived derive VBN cord-276598-tm0yj2sn 494 4 bioactive bioactive JJ cord-276598-tm0yj2sn 494 5 compound compound NN cord-276598-tm0yj2sn 494 6 ( ( -LRB- cord-276598-tm0yj2sn 494 7 19 19 CD cord-276598-tm0yj2sn 494 8 ) ) -RRB- cord-276598-tm0yj2sn 494 9 was be VBD cord-276598-tm0yj2sn 494 10 synthesized synthesize VBN cord-276598-tm0yj2sn 494 11 using use VBG cord-276598-tm0yj2sn 494 12 the the DT cord-276598-tm0yj2sn 494 13 proposed propose VBN cord-276598-tm0yj2sn 494 14 method method NN cord-276598-tm0yj2sn 494 15 ( ( -LRB- cord-276598-tm0yj2sn 494 16 Figure figure NN cord-276598-tm0yj2sn 494 17 9 9 CD cord-276598-tm0yj2sn 494 18 ) ) -RRB- cord-276598-tm0yj2sn 494 19 . . . cord-276598-tm0yj2sn 495 1 column column NN cord-276598-tm0yj2sn 495 2 chromatography chromatography NN cord-276598-tm0yj2sn 495 3 ( ( -LRB- cord-276598-tm0yj2sn 495 4 on on IN cord-276598-tm0yj2sn 495 5 silica silica NN cord-276598-tm0yj2sn 495 6 ) ) -RRB- cord-276598-tm0yj2sn 495 7 to to TO cord-276598-tm0yj2sn 495 8 afford afford VB cord-276598-tm0yj2sn 495 9 isolated isolated JJ cord-276598-tm0yj2sn 495 10 products product NNS cord-276598-tm0yj2sn 495 11 in in IN cord-276598-tm0yj2sn 495 12 the the DT cord-276598-tm0yj2sn 495 13 range range NN cord-276598-tm0yj2sn 495 14 of of IN cord-276598-tm0yj2sn 495 15 52 52 CD cord-276598-tm0yj2sn 495 16 - - SYM cord-276598-tm0yj2sn 495 17 96 96 CD cord-276598-tm0yj2sn 495 18 % % NN cord-276598-tm0yj2sn 495 19 yield yield NN cord-276598-tm0yj2sn 495 20 . . . cord-276598-tm0yj2sn 496 1 A a DT cord-276598-tm0yj2sn 496 2 broad broad JJ cord-276598-tm0yj2sn 496 3 scope scope NN cord-276598-tm0yj2sn 496 4 of of IN cord-276598-tm0yj2sn 496 5 the the DT cord-276598-tm0yj2sn 496 6 reaction reaction NN cord-276598-tm0yj2sn 496 7 was be VBD cord-276598-tm0yj2sn 496 8 tested test VBN cord-276598-tm0yj2sn 496 9 ; ; : cord-276598-tm0yj2sn 496 10 3-bromoprop-1-yne 3-bromoprop-1-yne NN cord-276598-tm0yj2sn 496 11 , , , cord-276598-tm0yj2sn 496 12 3-bromoprop-1-ene 3-bromoprop-1-ene CD cord-276598-tm0yj2sn 496 13 , , , cord-276598-tm0yj2sn 496 14 1-bromopropane 1-bromopropane CD cord-276598-tm0yj2sn 496 15 alkyl alkyl NN cord-276598-tm0yj2sn 496 16 or or CC cord-276598-tm0yj2sn 496 17 ( ( -LRB- cord-276598-tm0yj2sn 496 18 un)substituted un)substitute VBN cord-276598-tm0yj2sn 496 19 aromatic aromatic JJ cord-276598-tm0yj2sn 496 20 halide halide NN cord-276598-tm0yj2sn 496 21 such such JJ cord-276598-tm0yj2sn 496 22 as as IN cord-276598-tm0yj2sn 496 23 ( ( -LRB- cord-276598-tm0yj2sn 496 24 bromomethyl)benzene bromomethyl)benzene NNP cord-276598-tm0yj2sn 496 25 , , , cord-276598-tm0yj2sn 496 26 1-(bromomethyl)-2-nitrobenzene 1-(bromomethyl)-2-nitrobenzene CD cord-276598-tm0yj2sn 496 27 , , , cord-276598-tm0yj2sn 496 28 1-(chloromethyl)-4-nitrobenzene 1-(chloromethyl)-4-nitrobenzene CD cord-276598-tm0yj2sn 496 29 , , , cord-276598-tm0yj2sn 496 30 ( ( -LRB- cord-276598-tm0yj2sn 496 31 chloromethyl)benzene chloromethyl)benzene NNP cord-276598-tm0yj2sn 496 32 , , , cord-276598-tm0yj2sn 496 33 1-(bromomethyl)-3,5-dimethoxybenzene 1-(bromomethyl)-3,5-dimethoxybenzene CD cord-276598-tm0yj2sn 496 34 , , , cord-276598-tm0yj2sn 496 35 or or CC cord-276598-tm0yj2sn 496 36 3-(4-(bromomethyl)-1H-1,2,3-triazol-1-yl)benzyl 3-(4-(bromomethyl)-1h-1,2,3-triazol-1-yl)benzyl CD cord-276598-tm0yj2sn 496 37 acetate acetate NN cord-276598-tm0yj2sn 496 38 were be VBD cord-276598-tm0yj2sn 496 39 reacted react VBN cord-276598-tm0yj2sn 496 40 with with IN cord-276598-tm0yj2sn 496 41 dimethyl dimethyl NN cord-276598-tm0yj2sn 496 42 or or CC cord-276598-tm0yj2sn 496 43 diethyl diethyl NN cord-276598-tm0yj2sn 496 44 H h NN cord-276598-tm0yj2sn 497 1 -P. -P. : cord-276598-tm0yj2sn 497 2 A a DT cord-276598-tm0yj2sn 497 3 similar similar JJ cord-276598-tm0yj2sn 497 4 method method NN cord-276598-tm0yj2sn 497 5 of of IN cord-276598-tm0yj2sn 497 6 P p NN cord-276598-tm0yj2sn 497 7 - - HYPH cord-276598-tm0yj2sn 497 8 N n CD cord-276598-tm0yj2sn 497 9 synthesis synthesis NN cord-276598-tm0yj2sn 497 10 via via IN cord-276598-tm0yj2sn 497 11 in in IN cord-276598-tm0yj2sn 497 12 situ situ NN cord-276598-tm0yj2sn 497 13 azide azide NN cord-276598-tm0yj2sn 497 14 generation generation NN cord-276598-tm0yj2sn 497 15 from from IN cord-276598-tm0yj2sn 497 16 organic organic JJ cord-276598-tm0yj2sn 497 17 halides halide NNS cord-276598-tm0yj2sn 497 18 was be VBD cord-276598-tm0yj2sn 497 19 reported report VBN cord-276598-tm0yj2sn 497 20 by by IN cord-276598-tm0yj2sn 497 21 Dar Dar NNP cord-276598-tm0yj2sn 497 22 [ [ -LRB- cord-276598-tm0yj2sn 497 23 115 115 CD cord-276598-tm0yj2sn 497 24 ] ] -RRB- cord-276598-tm0yj2sn 497 25 , , , cord-276598-tm0yj2sn 497 26 following follow VBG cord-276598-tm0yj2sn 497 27 the the DT cord-276598-tm0yj2sn 497 28 procedure procedure NN cord-276598-tm0yj2sn 497 29 previously previously RB cord-276598-tm0yj2sn 497 30 reported report VBN cord-276598-tm0yj2sn 497 31 by by IN cord-276598-tm0yj2sn 497 32 Sangwan Sangwan NNP cord-276598-tm0yj2sn 497 33 et et NNP cord-276598-tm0yj2sn 497 34 al al NNP cord-276598-tm0yj2sn 497 35 . . . cord-276598-tm0yj2sn 498 1 ( ( -LRB- cord-276598-tm0yj2sn 498 2 Scheme scheme NN cord-276598-tm0yj2sn 498 3 11 11 CD cord-276598-tm0yj2sn 498 4 ) ) -RRB- cord-276598-tm0yj2sn 498 5 [ [ -LRB- cord-276598-tm0yj2sn 498 6 116 116 CD cord-276598-tm0yj2sn 498 7 ] ] -RRB- cord-276598-tm0yj2sn 498 8 . . . cord-276598-tm0yj2sn 499 1 The the DT cord-276598-tm0yj2sn 499 2 yield yield NN cord-276598-tm0yj2sn 499 3 range range NN cord-276598-tm0yj2sn 499 4 of of IN cord-276598-tm0yj2sn 499 5 the the DT cord-276598-tm0yj2sn 499 6 isolated isolate VBN cord-276598-tm0yj2sn 499 7 P p NN cord-276598-tm0yj2sn 499 8 - - HYPH cord-276598-tm0yj2sn 499 9 Ns Ns NNP cord-276598-tm0yj2sn 499 10 , , , cord-276598-tm0yj2sn 499 11 in in IN cord-276598-tm0yj2sn 499 12 this this DT cord-276598-tm0yj2sn 499 13 case case NN cord-276598-tm0yj2sn 499 14 , , , cord-276598-tm0yj2sn 499 15 was be VBD cord-276598-tm0yj2sn 499 16 60 60 CD cord-276598-tm0yj2sn 499 17 - - SYM cord-276598-tm0yj2sn 499 18 96 96 CD cord-276598-tm0yj2sn 499 19 % % NN cord-276598-tm0yj2sn 499 20 . . . cord-276598-tm0yj2sn 500 1 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 500 2 - - HYPH cord-276598-tm0yj2sn 500 3 derived derive VBN cord-276598-tm0yj2sn 500 4 bioactive bioactive JJ cord-276598-tm0yj2sn 500 5 compound compound NN cord-276598-tm0yj2sn 500 6 ( ( -LRB- cord-276598-tm0yj2sn 500 7 19 19 CD cord-276598-tm0yj2sn 500 8 ) ) -RRB- cord-276598-tm0yj2sn 500 9 was be VBD cord-276598-tm0yj2sn 500 10 synthesized synthesize VBN cord-276598-tm0yj2sn 500 11 using use VBG cord-276598-tm0yj2sn 500 12 the the DT cord-276598-tm0yj2sn 500 13 proposed propose VBN cord-276598-tm0yj2sn 500 14 method method NN cord-276598-tm0yj2sn 500 15 ( ( -LRB- cord-276598-tm0yj2sn 500 16 Figure figure NN cord-276598-tm0yj2sn 500 17 9 9 CD cord-276598-tm0yj2sn 500 18 ) ) -RRB- cord-276598-tm0yj2sn 500 19 . . . cord-276598-tm0yj2sn 501 1 Scheme scheme NN cord-276598-tm0yj2sn 501 2 11 11 CD cord-276598-tm0yj2sn 501 3 . . . cord-276598-tm0yj2sn 502 1 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 502 2 synthesis synthesis NN cord-276598-tm0yj2sn 502 3 from from IN cord-276598-tm0yj2sn 502 4 organic organic JJ cord-276598-tm0yj2sn 502 5 azide azide NN cord-276598-tm0yj2sn 502 6 and and CC cord-276598-tm0yj2sn 502 7 ( ( -LRB- cord-276598-tm0yj2sn 502 8 RO)3P. ro)3p. IN cord-276598-tm0yj2sn 502 9 Figure figure NN cord-276598-tm0yj2sn 502 10 9 9 CD cord-276598-tm0yj2sn 502 11 . . . cord-276598-tm0yj2sn 503 1 Structure structure NN cord-276598-tm0yj2sn 503 2 of of IN cord-276598-tm0yj2sn 503 3 ( ( -LRB- cord-276598-tm0yj2sn 503 4 1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 1r,2s,5r)-2-isopropyl-5-methylcyclohexyl CD cord-276598-tm0yj2sn 503 5 ( ( -LRB- cord-276598-tm0yj2sn 503 6 dimethoxyphosphoryl)glycinate dimethoxyphosphoryl)glycinate NNP cord-276598-tm0yj2sn 503 7 ( ( -LRB- cord-276598-tm0yj2sn 503 8 19 19 CD cord-276598-tm0yj2sn 503 9 ) ) -RRB- cord-276598-tm0yj2sn 503 10 synthesized synthesize VBN cord-276598-tm0yj2sn 503 11 via via IN cord-276598-tm0yj2sn 503 12 in in IN cord-276598-tm0yj2sn 503 13 situ situ NN cord-276598-tm0yj2sn 503 14 azide azide NN cord-276598-tm0yj2sn 503 15 generation generation NN cord-276598-tm0yj2sn 503 16 . . . cord-276598-tm0yj2sn 504 1 In in IN cord-276598-tm0yj2sn 504 2 1988 1988 CD cord-276598-tm0yj2sn 504 3 , , , cord-276598-tm0yj2sn 504 4 Koziara Koziara NNP cord-276598-tm0yj2sn 504 5 reported report VBD cord-276598-tm0yj2sn 504 6 a a DT cord-276598-tm0yj2sn 504 7 two two CD cord-276598-tm0yj2sn 504 8 - - HYPH cord-276598-tm0yj2sn 504 9 step step NN cord-276598-tm0yj2sn 504 10 P p NN cord-276598-tm0yj2sn 504 11 - - HYPH cord-276598-tm0yj2sn 504 12 N n CD cord-276598-tm0yj2sn 504 13 synthetic synthetic JJ cord-276598-tm0yj2sn 504 14 route route NN cord-276598-tm0yj2sn 504 15 via via IN cord-276598-tm0yj2sn 504 16 organic organic JJ cord-276598-tm0yj2sn 504 17 azide azide NN cord-276598-tm0yj2sn 504 18 generation generation NN cord-276598-tm0yj2sn 504 19 using use VBG cord-276598-tm0yj2sn 504 20 a a DT cord-276598-tm0yj2sn 504 21 [ [ -LRB- cord-276598-tm0yj2sn 504 22 n n NNP cord-276598-tm0yj2sn 504 23 - - HYPH cord-276598-tm0yj2sn 504 24 Bu4N]Br Bu4N]Br NNP cord-276598-tm0yj2sn 504 25 catalyst catalyst NN cord-276598-tm0yj2sn 504 26 ( ( -LRB- cord-276598-tm0yj2sn 504 27 Scheme scheme NN cord-276598-tm0yj2sn 504 28 12 12 CD cord-276598-tm0yj2sn 504 29 ) ) -RRB- cord-276598-tm0yj2sn 504 30 [ [ -LRB- cord-276598-tm0yj2sn 504 31 93 93 CD cord-276598-tm0yj2sn 504 32 ] ] -RRB- cord-276598-tm0yj2sn 504 33 . . . cord-276598-tm0yj2sn 505 1 The the DT cord-276598-tm0yj2sn 505 2 crude crude JJ cord-276598-tm0yj2sn 505 3 product product NN cord-276598-tm0yj2sn 505 4 was be VBD cord-276598-tm0yj2sn 505 5 purified purify VBN cord-276598-tm0yj2sn 505 6 by by IN cord-276598-tm0yj2sn 505 7 crystallization crystallization NN cord-276598-tm0yj2sn 505 8 or or CC cord-276598-tm0yj2sn 505 9 vacuum vacuum NN cord-276598-tm0yj2sn 505 10 distillation distillation NN cord-276598-tm0yj2sn 505 11 with with IN cord-276598-tm0yj2sn 505 12 50 50 CD cord-276598-tm0yj2sn 505 13 - - SYM cord-276598-tm0yj2sn 505 14 93 93 CD cord-276598-tm0yj2sn 505 15 % % NN cord-276598-tm0yj2sn 505 16 isolated isolated JJ cord-276598-tm0yj2sn 505 17 yield yield NN cord-276598-tm0yj2sn 505 18 . . . cord-276598-tm0yj2sn 506 1 The the DT cord-276598-tm0yj2sn 506 2 organic organic JJ cord-276598-tm0yj2sn 506 3 halides halide NNS cord-276598-tm0yj2sn 506 4 used use VBN cord-276598-tm0yj2sn 506 5 were be VBD cord-276598-tm0yj2sn 506 6 ( ( -LRB- cord-276598-tm0yj2sn 506 7 3-bromopropyl)benzene 3-bromopropyl)benzene CD cord-276598-tm0yj2sn 506 8 , , , cord-276598-tm0yj2sn 506 9 ( ( -LRB- cord-276598-tm0yj2sn 506 10 2-bromoethyl)benzene 2-bromoethyl)benzene CD cord-276598-tm0yj2sn 506 11 , , , cord-276598-tm0yj2sn 506 12 1-bromohexane 1-bromohexane CD cord-276598-tm0yj2sn 506 13 , , , cord-276598-tm0yj2sn 506 14 bromocyclohexane bromocyclohexane NNP cord-276598-tm0yj2sn 506 15 , , , cord-276598-tm0yj2sn 506 16 1-bromobutane 1-bromobutane CD cord-276598-tm0yj2sn 506 17 , , , cord-276598-tm0yj2sn 506 18 or or CC cord-276598-tm0yj2sn 506 19 bromocyclopentane bromocyclopentane NNP cord-276598-tm0yj2sn 506 20 . . . cord-276598-tm0yj2sn 507 1 Routes route NNS cord-276598-tm0yj2sn 507 2 via via IN cord-276598-tm0yj2sn 507 3 organic organic JJ cord-276598-tm0yj2sn 507 4 azide azide NN cord-276598-tm0yj2sn 507 5 generation generation NN cord-276598-tm0yj2sn 507 6 use use NN cord-276598-tm0yj2sn 507 7 readily readily RB cord-276598-tm0yj2sn 507 8 available available JJ cord-276598-tm0yj2sn 507 9 , , , cord-276598-tm0yj2sn 507 10 less less RBR cord-276598-tm0yj2sn 507 11 toxic toxic JJ cord-276598-tm0yj2sn 507 12 organic organic JJ cord-276598-tm0yj2sn 507 13 halides halide NNS cord-276598-tm0yj2sn 508 1 and and CC cord-276598-tm0yj2sn 508 2 ( ( -LRB- cord-276598-tm0yj2sn 508 3 RO)3P RO)3P NNP cord-276598-tm0yj2sn 508 4 ( ( -LRB- cord-276598-tm0yj2sn 508 5 R r NN cord-276598-tm0yj2sn 508 6 = = NN cord-276598-tm0yj2sn 508 7 alkyl alkyl NN cord-276598-tm0yj2sn 508 8 ) ) -RRB- cord-276598-tm0yj2sn 508 9 relative relative JJ cord-276598-tm0yj2sn 508 10 to to IN cord-276598-tm0yj2sn 508 11 other other JJ cord-276598-tm0yj2sn 508 12 routes route NNS cord-276598-tm0yj2sn 508 13 and and CC cord-276598-tm0yj2sn 508 14 generate generate VB cord-276598-tm0yj2sn 508 15 N2 n2 NN cord-276598-tm0yj2sn 508 16 as as IN cord-276598-tm0yj2sn 508 17 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 508 18 waste waste NN cord-276598-tm0yj2sn 508 19 . . . cord-276598-tm0yj2sn 509 1 However however RB cord-276598-tm0yj2sn 509 2 , , , cord-276598-tm0yj2sn 509 3 the the DT cord-276598-tm0yj2sn 509 4 method method NN cord-276598-tm0yj2sn 509 5 Figure figure NN cord-276598-tm0yj2sn 509 6 9 9 CD cord-276598-tm0yj2sn 509 7 . . . cord-276598-tm0yj2sn 510 1 Structure structure NN cord-276598-tm0yj2sn 510 2 of of IN cord-276598-tm0yj2sn 510 3 ( ( -LRB- cord-276598-tm0yj2sn 510 4 1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 1r,2s,5r)-2-isopropyl-5-methylcyclohexyl CD cord-276598-tm0yj2sn 510 5 ( ( -LRB- cord-276598-tm0yj2sn 510 6 dimethoxyphosphoryl)glycinate dimethoxyphosphoryl)glycinate NNP cord-276598-tm0yj2sn 510 7 ( ( -LRB- cord-276598-tm0yj2sn 510 8 19 19 CD cord-276598-tm0yj2sn 510 9 ) ) -RRB- cord-276598-tm0yj2sn 510 10 synthesized synthesize VBN cord-276598-tm0yj2sn 510 11 via via IN cord-276598-tm0yj2sn 510 12 in in IN cord-276598-tm0yj2sn 510 13 situ situ NN cord-276598-tm0yj2sn 510 14 azide azide NN cord-276598-tm0yj2sn 510 15 generation generation NN cord-276598-tm0yj2sn 510 16 . . . cord-276598-tm0yj2sn 511 1 In in IN cord-276598-tm0yj2sn 511 2 1988 1988 CD cord-276598-tm0yj2sn 511 3 , , , cord-276598-tm0yj2sn 511 4 Koziara Koziara NNP cord-276598-tm0yj2sn 511 5 reported report VBD cord-276598-tm0yj2sn 511 6 a a DT cord-276598-tm0yj2sn 511 7 two two CD cord-276598-tm0yj2sn 511 8 - - HYPH cord-276598-tm0yj2sn 511 9 step step NN cord-276598-tm0yj2sn 511 10 P p NN cord-276598-tm0yj2sn 511 11 - - HYPH cord-276598-tm0yj2sn 511 12 N n CD cord-276598-tm0yj2sn 511 13 synthetic synthetic JJ cord-276598-tm0yj2sn 511 14 route route NN cord-276598-tm0yj2sn 511 15 via via IN cord-276598-tm0yj2sn 511 16 organic organic JJ cord-276598-tm0yj2sn 511 17 azide azide NN cord-276598-tm0yj2sn 511 18 generation generation NN cord-276598-tm0yj2sn 511 19 using use VBG cord-276598-tm0yj2sn 511 20 a a DT cord-276598-tm0yj2sn 511 21 [ [ -LRB- cord-276598-tm0yj2sn 511 22 n n NNP cord-276598-tm0yj2sn 511 23 - - HYPH cord-276598-tm0yj2sn 511 24 Bu Bu NNP cord-276598-tm0yj2sn 511 25 4 4 CD cord-276598-tm0yj2sn 511 26 N]Br N]Br NNP cord-276598-tm0yj2sn 511 27 catalyst catalyst NN cord-276598-tm0yj2sn 511 28 ( ( -LRB- cord-276598-tm0yj2sn 511 29 Scheme scheme NN cord-276598-tm0yj2sn 511 30 12 12 CD cord-276598-tm0yj2sn 511 31 ) ) -RRB- cord-276598-tm0yj2sn 512 1 [ [ -LRB- cord-276598-tm0yj2sn 512 2 93 93 CD cord-276598-tm0yj2sn 512 3 ] ] -RRB- cord-276598-tm0yj2sn 512 4 . . . cord-276598-tm0yj2sn 513 1 The the DT cord-276598-tm0yj2sn 513 2 crude crude JJ cord-276598-tm0yj2sn 513 3 product product NN cord-276598-tm0yj2sn 513 4 was be VBD cord-276598-tm0yj2sn 513 5 purified purify VBN cord-276598-tm0yj2sn 513 6 by by IN cord-276598-tm0yj2sn 513 7 crystallization crystallization NN cord-276598-tm0yj2sn 513 8 or or CC cord-276598-tm0yj2sn 513 9 vacuum vacuum NN cord-276598-tm0yj2sn 513 10 distillation distillation NN cord-276598-tm0yj2sn 513 11 with with IN cord-276598-tm0yj2sn 513 12 50 50 CD cord-276598-tm0yj2sn 513 13 - - SYM cord-276598-tm0yj2sn 513 14 93 93 CD cord-276598-tm0yj2sn 513 15 % % NN cord-276598-tm0yj2sn 513 16 isolated isolated JJ cord-276598-tm0yj2sn 513 17 yield yield NN cord-276598-tm0yj2sn 513 18 . . . cord-276598-tm0yj2sn 514 1 The the DT cord-276598-tm0yj2sn 514 2 organic organic JJ cord-276598-tm0yj2sn 514 3 halides halide NNS cord-276598-tm0yj2sn 514 4 used use VBN cord-276598-tm0yj2sn 514 5 were be VBD cord-276598-tm0yj2sn 514 6 ( ( -LRB- cord-276598-tm0yj2sn 514 7 3-bromopropyl)benzene 3-bromopropyl)benzene CD cord-276598-tm0yj2sn 514 8 , , , cord-276598-tm0yj2sn 514 9 ( ( -LRB- cord-276598-tm0yj2sn 514 10 2-bromoethyl)benzene 2-bromoethyl)benzene CD cord-276598-tm0yj2sn 514 11 , , , cord-276598-tm0yj2sn 514 12 1-bromohexane 1-bromohexane CD cord-276598-tm0yj2sn 514 13 , , , cord-276598-tm0yj2sn 514 14 bromocyclohexane bromocyclohexane NNP cord-276598-tm0yj2sn 514 15 , , , cord-276598-tm0yj2sn 514 16 1-bromobutane 1-bromobutane CD cord-276598-tm0yj2sn 514 17 , , , cord-276598-tm0yj2sn 514 18 or or CC cord-276598-tm0yj2sn 514 19 bromocyclopentane bromocyclopentane NNP cord-276598-tm0yj2sn 514 20 . . . cord-276598-tm0yj2sn 515 1 relies rely VBZ cord-276598-tm0yj2sn 515 2 on on IN cord-276598-tm0yj2sn 515 3 the the DT cord-276598-tm0yj2sn 515 4 pre pre JJ cord-276598-tm0yj2sn 515 5 - - NN cord-276598-tm0yj2sn 515 6 functionalization functionalization NN cord-276598-tm0yj2sn 515 7 and and CC cord-276598-tm0yj2sn 515 8 preparation preparation NN cord-276598-tm0yj2sn 515 9 of of IN cord-276598-tm0yj2sn 515 10 hazardous hazardous JJ cord-276598-tm0yj2sn 515 11 azide azide NN cord-276598-tm0yj2sn 515 12 precursors precursor NNS cord-276598-tm0yj2sn 515 13 in in IN cord-276598-tm0yj2sn 515 14 multi multi JJ cord-276598-tm0yj2sn 515 15 - - JJ cord-276598-tm0yj2sn 515 16 step step JJ cord-276598-tm0yj2sn 515 17 processes process NNS cord-276598-tm0yj2sn 515 18 . . . cord-276598-tm0yj2sn 516 1 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 516 2 synthesis synthesis NN cord-276598-tm0yj2sn 516 3 via via IN cord-276598-tm0yj2sn 516 4 two two CD cord-276598-tm0yj2sn 516 5 - - HYPH cord-276598-tm0yj2sn 516 6 step step NN cord-276598-tm0yj2sn 516 7 organic organic JJ cord-276598-tm0yj2sn 516 8 azide azide NN cord-276598-tm0yj2sn 516 9 generation generation NN cord-276598-tm0yj2sn 516 10 . . . cord-276598-tm0yj2sn 517 1 Transition transition NN cord-276598-tm0yj2sn 517 2 metal metal NN cord-276598-tm0yj2sn 517 3 - - HYPH cord-276598-tm0yj2sn 517 4 free free JJ cord-276598-tm0yj2sn 517 5 synthesis synthesis NN cord-276598-tm0yj2sn 517 6 of of IN cord-276598-tm0yj2sn 517 7 P P NNP cord-276598-tm0yj2sn 517 8 - - HYPH cord-276598-tm0yj2sn 517 9 N N NNP cord-276598-tm0yj2sn 517 10 from from IN cord-276598-tm0yj2sn 517 11 phosphoryl phosphoryl NNS cord-276598-tm0yj2sn 517 12 azide azide NN cord-276598-tm0yj2sn 517 13 and and CC cord-276598-tm0yj2sn 517 14 amines amine NNS cord-276598-tm0yj2sn 517 15 was be VBD cord-276598-tm0yj2sn 517 16 accomplished accomplish VBN cord-276598-tm0yj2sn 517 17 by by IN cord-276598-tm0yj2sn 517 18 Chen Chen NNP cord-276598-tm0yj2sn 517 19 et et NNP cord-276598-tm0yj2sn 517 20 al al NNP cord-276598-tm0yj2sn 517 21 . . . cord-276598-tm0yj2sn 518 1 [ [ -LRB- cord-276598-tm0yj2sn 518 2 117 117 CD cord-276598-tm0yj2sn 518 3 ] ] -RRB- cord-276598-tm0yj2sn 518 4 . . . cord-276598-tm0yj2sn 519 1 The the DT cord-276598-tm0yj2sn 519 2 synthetic synthetic JJ cord-276598-tm0yj2sn 519 3 process process NN cord-276598-tm0yj2sn 519 4 uses use VBZ cord-276598-tm0yj2sn 519 5 the the DT cord-276598-tm0yj2sn 519 6 nitrogen nitrogen NN cord-276598-tm0yj2sn 519 7 atom atom NN cord-276598-tm0yj2sn 519 8 available available JJ cord-276598-tm0yj2sn 519 9 from from IN cord-276598-tm0yj2sn 519 10 the the DT cord-276598-tm0yj2sn 519 11 amine amine NN cord-276598-tm0yj2sn 519 12 rather rather RB cord-276598-tm0yj2sn 519 13 than than IN cord-276598-tm0yj2sn 519 14 from from IN cord-276598-tm0yj2sn 519 15 the the DT cord-276598-tm0yj2sn 519 16 azide azide NN cord-276598-tm0yj2sn 519 17 ( ( -LRB- cord-276598-tm0yj2sn 519 18 Scheme scheme NN cord-276598-tm0yj2sn 519 19 13 13 CD cord-276598-tm0yj2sn 519 20 ) ) -RRB- cord-276598-tm0yj2sn 519 21 . . . cord-276598-tm0yj2sn 520 1 The the DT cord-276598-tm0yj2sn 520 2 residue residue NN cord-276598-tm0yj2sn 520 3 was be VBD cord-276598-tm0yj2sn 520 4 purified purify VBN cord-276598-tm0yj2sn 520 5 by by IN cord-276598-tm0yj2sn 520 6 column column NN cord-276598-tm0yj2sn 520 7 chromatography chromatography NN cord-276598-tm0yj2sn 520 8 ( ( -LRB- cord-276598-tm0yj2sn 520 9 on on IN cord-276598-tm0yj2sn 520 10 silica silica NN cord-276598-tm0yj2sn 520 11 ) ) -RRB- cord-276598-tm0yj2sn 520 12 to to TO cord-276598-tm0yj2sn 520 13 afford afford VB cord-276598-tm0yj2sn 520 14 the the DT cord-276598-tm0yj2sn 520 15 isolated isolate VBN cord-276598-tm0yj2sn 520 16 product product NN cord-276598-tm0yj2sn 520 17 in in IN cord-276598-tm0yj2sn 520 18 52 52 CD cord-276598-tm0yj2sn 520 19 - - SYM cord-276598-tm0yj2sn 520 20 92 92 CD cord-276598-tm0yj2sn 520 21 % % NN cord-276598-tm0yj2sn 520 22 yield yield NN cord-276598-tm0yj2sn 520 23 . . . cord-276598-tm0yj2sn 521 1 The the DT cord-276598-tm0yj2sn 521 2 scope scope NN cord-276598-tm0yj2sn 521 3 of of IN cord-276598-tm0yj2sn 521 4 the the DT cord-276598-tm0yj2sn 521 5 reaction reaction NN cord-276598-tm0yj2sn 521 6 was be VBD cord-276598-tm0yj2sn 521 7 examined examine VBN cord-276598-tm0yj2sn 521 8 by by IN cord-276598-tm0yj2sn 521 9 using use VBG cord-276598-tm0yj2sn 521 10 diphenyl diphenyl NNP cord-276598-tm0yj2sn 521 11 and and CC cord-276598-tm0yj2sn 521 12 diisopropyl diisopropyl NNP cord-276598-tm0yj2sn 521 13 phosphoryl phosphoryl NNP cord-276598-tm0yj2sn 521 14 azide azide NN cord-276598-tm0yj2sn 521 15 along along IN cord-276598-tm0yj2sn 521 16 with with IN cord-276598-tm0yj2sn 521 17 primary primary JJ cord-276598-tm0yj2sn 521 18 amines amine NNS cord-276598-tm0yj2sn 521 19 ( ( -LRB- cord-276598-tm0yj2sn 521 20 e.g. e.g. RB cord-276598-tm0yj2sn 521 21 , , , cord-276598-tm0yj2sn 521 22 isopropylamine isopropylamine NN cord-276598-tm0yj2sn 521 23 and and CC cord-276598-tm0yj2sn 521 24 t t NN cord-276598-tm0yj2sn 521 25 - - HYPH cord-276598-tm0yj2sn 521 26 butylamine butylamine NNP cord-276598-tm0yj2sn 521 27 ) ) -RRB- cord-276598-tm0yj2sn 521 28 , , , cord-276598-tm0yj2sn 521 29 substituted substitute VBN cord-276598-tm0yj2sn 521 30 primary primary JJ cord-276598-tm0yj2sn 521 31 amines amine NNS cord-276598-tm0yj2sn 521 32 ( ( -LRB- cord-276598-tm0yj2sn 521 33 e.g. e.g. RB cord-276598-tm0yj2sn 521 34 , , , cord-276598-tm0yj2sn 521 35 thiophen-2-ylmethylamine thiophen-2-ylmethylamine NNP cord-276598-tm0yj2sn 521 36 and and CC cord-276598-tm0yj2sn 521 37 4-chlorobenzylamine 4-chlorobenzylamine CD cord-276598-tm0yj2sn 521 38 ) ) -RRB- cord-276598-tm0yj2sn 521 39 , , , cord-276598-tm0yj2sn 521 40 and and CC cord-276598-tm0yj2sn 521 41 heterocyclic heterocyclic JJ cord-276598-tm0yj2sn 521 42 amines amine NNS cord-276598-tm0yj2sn 521 43 ( ( -LRB- cord-276598-tm0yj2sn 521 44 e.g. e.g. RB cord-276598-tm0yj2sn 521 45 , , , cord-276598-tm0yj2sn 521 46 pyrrolidine pyrrolidine JJ cord-276598-tm0yj2sn 521 47 and and CC cord-276598-tm0yj2sn 521 48 morpholine morpholine NNP cord-276598-tm0yj2sn 521 49 ) ) -RRB- cord-276598-tm0yj2sn 521 50 . . . cord-276598-tm0yj2sn 522 1 Although although IN cord-276598-tm0yj2sn 522 2 the the DT cord-276598-tm0yj2sn 522 3 method method NN cord-276598-tm0yj2sn 522 4 circumvents circumvent VBZ cord-276598-tm0yj2sn 522 5 the the DT cord-276598-tm0yj2sn 522 6 use use NN cord-276598-tm0yj2sn 522 7 of of IN cord-276598-tm0yj2sn 522 8 metal metal NN cord-276598-tm0yj2sn 522 9 catalysts catalyst NNS cord-276598-tm0yj2sn 522 10 in in IN cord-276598-tm0yj2sn 522 11 the the DT cord-276598-tm0yj2sn 522 12 synthesis synthesis NN cord-276598-tm0yj2sn 522 13 , , , cord-276598-tm0yj2sn 522 14 the the DT cord-276598-tm0yj2sn 522 15 use use NN cord-276598-tm0yj2sn 522 16 of of IN cord-276598-tm0yj2sn 522 17 a a DT cord-276598-tm0yj2sn 522 18 hazardous hazardous JJ cord-276598-tm0yj2sn 522 19 azide azide NN cord-276598-tm0yj2sn 522 20 and and CC cord-276598-tm0yj2sn 522 21 high high JJ cord-276598-tm0yj2sn 522 22 temperature temperature NN cord-276598-tm0yj2sn 522 23 are be VBP cord-276598-tm0yj2sn 522 24 its -PRON- PRP$ cord-276598-tm0yj2sn 522 25 limitations limitation NNS cord-276598-tm0yj2sn 522 26 . . . cord-276598-tm0yj2sn 523 1 Scheme scheme NN cord-276598-tm0yj2sn 523 2 13 13 CD cord-276598-tm0yj2sn 523 3 . . . cord-276598-tm0yj2sn 524 1 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 524 2 synthesis synthesis NN cord-276598-tm0yj2sn 524 3 from from IN cord-276598-tm0yj2sn 524 4 organic organic JJ cord-276598-tm0yj2sn 524 5 azide azide NN cord-276598-tm0yj2sn 524 6 and and CC cord-276598-tm0yj2sn 524 7 amine amine NN cord-276598-tm0yj2sn 524 8 . . . cord-276598-tm0yj2sn 525 1 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 525 2 synthesis synthesis NN cord-276598-tm0yj2sn 525 3 via via IN cord-276598-tm0yj2sn 525 4 two two CD cord-276598-tm0yj2sn 525 5 - - HYPH cord-276598-tm0yj2sn 525 6 step step NN cord-276598-tm0yj2sn 525 7 organic organic JJ cord-276598-tm0yj2sn 525 8 azide azide NN cord-276598-tm0yj2sn 525 9 generation generation NN cord-276598-tm0yj2sn 525 10 . . . cord-276598-tm0yj2sn 526 1 Routes route NNS cord-276598-tm0yj2sn 526 2 via via IN cord-276598-tm0yj2sn 526 3 organic organic JJ cord-276598-tm0yj2sn 526 4 azide azide NN cord-276598-tm0yj2sn 526 5 generation generation NN cord-276598-tm0yj2sn 526 6 use use NN cord-276598-tm0yj2sn 526 7 readily readily RB cord-276598-tm0yj2sn 526 8 available available JJ cord-276598-tm0yj2sn 526 9 , , , cord-276598-tm0yj2sn 526 10 less less RBR cord-276598-tm0yj2sn 526 11 toxic toxic JJ cord-276598-tm0yj2sn 526 12 organic organic JJ cord-276598-tm0yj2sn 526 13 halides halide NNS cord-276598-tm0yj2sn 527 1 and and CC cord-276598-tm0yj2sn 527 2 ( ( -LRB- cord-276598-tm0yj2sn 527 3 RO RO NNP cord-276598-tm0yj2sn 527 4 ) ) -RRB- cord-276598-tm0yj2sn 527 5 3 3 CD cord-276598-tm0yj2sn 527 6 P p NN cord-276598-tm0yj2sn 527 7 ( ( -LRB- cord-276598-tm0yj2sn 527 8 R r NN cord-276598-tm0yj2sn 527 9 = = NN cord-276598-tm0yj2sn 527 10 alkyl alkyl NN cord-276598-tm0yj2sn 527 11 ) ) -RRB- cord-276598-tm0yj2sn 527 12 relative relative JJ cord-276598-tm0yj2sn 527 13 to to IN cord-276598-tm0yj2sn 527 14 other other JJ cord-276598-tm0yj2sn 527 15 routes route NNS cord-276598-tm0yj2sn 527 16 and and CC cord-276598-tm0yj2sn 527 17 generate generate VB cord-276598-tm0yj2sn 527 18 N n CD cord-276598-tm0yj2sn 527 19 2 2 CD cord-276598-tm0yj2sn 527 20 as as IN cord-276598-tm0yj2sn 527 21 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 527 22 waste waste NN cord-276598-tm0yj2sn 527 23 . . . cord-276598-tm0yj2sn 528 1 However however RB cord-276598-tm0yj2sn 528 2 , , , cord-276598-tm0yj2sn 528 3 the the DT cord-276598-tm0yj2sn 528 4 method method NN cord-276598-tm0yj2sn 528 5 relies rely VBZ cord-276598-tm0yj2sn 528 6 on on IN cord-276598-tm0yj2sn 528 7 the the DT cord-276598-tm0yj2sn 528 8 pre pre JJ cord-276598-tm0yj2sn 528 9 - - NN cord-276598-tm0yj2sn 528 10 functionalization functionalization NN cord-276598-tm0yj2sn 528 11 and and CC cord-276598-tm0yj2sn 528 12 preparation preparation NN cord-276598-tm0yj2sn 528 13 of of IN cord-276598-tm0yj2sn 528 14 hazardous hazardous JJ cord-276598-tm0yj2sn 528 15 azide azide NN cord-276598-tm0yj2sn 528 16 precursors precursor NNS cord-276598-tm0yj2sn 528 17 in in IN cord-276598-tm0yj2sn 528 18 multi multi JJ cord-276598-tm0yj2sn 528 19 - - JJ cord-276598-tm0yj2sn 528 20 step step JJ cord-276598-tm0yj2sn 528 21 processes process NNS cord-276598-tm0yj2sn 528 22 . . . cord-276598-tm0yj2sn 529 1 Transition transition NN cord-276598-tm0yj2sn 529 2 metal metal NN cord-276598-tm0yj2sn 529 3 - - HYPH cord-276598-tm0yj2sn 529 4 free free JJ cord-276598-tm0yj2sn 529 5 synthesis synthesis NN cord-276598-tm0yj2sn 529 6 of of IN cord-276598-tm0yj2sn 529 7 P P NNP cord-276598-tm0yj2sn 529 8 - - HYPH cord-276598-tm0yj2sn 529 9 N N NNP cord-276598-tm0yj2sn 529 10 from from IN cord-276598-tm0yj2sn 529 11 phosphoryl phosphoryl NNS cord-276598-tm0yj2sn 529 12 azide azide NN cord-276598-tm0yj2sn 529 13 and and CC cord-276598-tm0yj2sn 529 14 amines amine NNS cord-276598-tm0yj2sn 529 15 was be VBD cord-276598-tm0yj2sn 529 16 accomplished accomplish VBN cord-276598-tm0yj2sn 529 17 by by IN cord-276598-tm0yj2sn 529 18 Chen Chen NNP cord-276598-tm0yj2sn 529 19 et et NNP cord-276598-tm0yj2sn 529 20 al al NNP cord-276598-tm0yj2sn 529 21 . . . cord-276598-tm0yj2sn 530 1 [ [ -LRB- cord-276598-tm0yj2sn 530 2 117 117 CD cord-276598-tm0yj2sn 530 3 ] ] -RRB- cord-276598-tm0yj2sn 530 4 . . . cord-276598-tm0yj2sn 531 1 The the DT cord-276598-tm0yj2sn 531 2 synthetic synthetic JJ cord-276598-tm0yj2sn 531 3 process process NN cord-276598-tm0yj2sn 531 4 uses use VBZ cord-276598-tm0yj2sn 531 5 the the DT cord-276598-tm0yj2sn 531 6 nitrogen nitrogen NN cord-276598-tm0yj2sn 531 7 atom atom NN cord-276598-tm0yj2sn 531 8 available available JJ cord-276598-tm0yj2sn 531 9 from from IN cord-276598-tm0yj2sn 531 10 the the DT cord-276598-tm0yj2sn 531 11 amine amine NN cord-276598-tm0yj2sn 531 12 rather rather RB cord-276598-tm0yj2sn 531 13 than than IN cord-276598-tm0yj2sn 531 14 from from IN cord-276598-tm0yj2sn 531 15 the the DT cord-276598-tm0yj2sn 531 16 azide azide NN cord-276598-tm0yj2sn 531 17 ( ( -LRB- cord-276598-tm0yj2sn 531 18 Scheme scheme NN cord-276598-tm0yj2sn 531 19 13 13 CD cord-276598-tm0yj2sn 531 20 ) ) -RRB- cord-276598-tm0yj2sn 531 21 . . . cord-276598-tm0yj2sn 532 1 The the DT cord-276598-tm0yj2sn 532 2 residue residue NN cord-276598-tm0yj2sn 532 3 was be VBD cord-276598-tm0yj2sn 532 4 purified purify VBN cord-276598-tm0yj2sn 532 5 by by IN cord-276598-tm0yj2sn 532 6 column column NN cord-276598-tm0yj2sn 532 7 chromatography chromatography NN cord-276598-tm0yj2sn 532 8 ( ( -LRB- cord-276598-tm0yj2sn 532 9 on on IN cord-276598-tm0yj2sn 532 10 silica silica NN cord-276598-tm0yj2sn 532 11 ) ) -RRB- cord-276598-tm0yj2sn 532 12 to to TO cord-276598-tm0yj2sn 532 13 afford afford VB cord-276598-tm0yj2sn 532 14 the the DT cord-276598-tm0yj2sn 532 15 isolated isolate VBN cord-276598-tm0yj2sn 532 16 product product NN cord-276598-tm0yj2sn 532 17 in in IN cord-276598-tm0yj2sn 532 18 52 52 CD cord-276598-tm0yj2sn 532 19 - - SYM cord-276598-tm0yj2sn 532 20 92 92 CD cord-276598-tm0yj2sn 532 21 % % NN cord-276598-tm0yj2sn 532 22 yield yield NN cord-276598-tm0yj2sn 532 23 . . . cord-276598-tm0yj2sn 533 1 The the DT cord-276598-tm0yj2sn 533 2 scope scope NN cord-276598-tm0yj2sn 533 3 of of IN cord-276598-tm0yj2sn 533 4 the the DT cord-276598-tm0yj2sn 533 5 reaction reaction NN cord-276598-tm0yj2sn 533 6 was be VBD cord-276598-tm0yj2sn 533 7 examined examine VBN cord-276598-tm0yj2sn 533 8 by by IN cord-276598-tm0yj2sn 533 9 using use VBG cord-276598-tm0yj2sn 533 10 diphenyl diphenyl NNP cord-276598-tm0yj2sn 533 11 and and CC cord-276598-tm0yj2sn 533 12 diisopropyl diisopropyl NNP cord-276598-tm0yj2sn 533 13 phosphoryl phosphoryl NNP cord-276598-tm0yj2sn 533 14 azide azide NN cord-276598-tm0yj2sn 533 15 along along IN cord-276598-tm0yj2sn 533 16 with with IN cord-276598-tm0yj2sn 533 17 primary primary JJ cord-276598-tm0yj2sn 533 18 amines amine NNS cord-276598-tm0yj2sn 533 19 ( ( -LRB- cord-276598-tm0yj2sn 533 20 e.g. e.g. RB cord-276598-tm0yj2sn 533 21 , , , cord-276598-tm0yj2sn 533 22 isopropylamine isopropylamine NN cord-276598-tm0yj2sn 533 23 and and CC cord-276598-tm0yj2sn 533 24 t t NN cord-276598-tm0yj2sn 533 25 - - HYPH cord-276598-tm0yj2sn 533 26 butylamine butylamine NNP cord-276598-tm0yj2sn 533 27 ) ) -RRB- cord-276598-tm0yj2sn 533 28 , , , cord-276598-tm0yj2sn 533 29 substituted substitute VBN cord-276598-tm0yj2sn 533 30 primary primary JJ cord-276598-tm0yj2sn 533 31 amines amine NNS cord-276598-tm0yj2sn 533 32 ( ( -LRB- cord-276598-tm0yj2sn 533 33 e.g. e.g. RB cord-276598-tm0yj2sn 533 34 , , , cord-276598-tm0yj2sn 533 35 thiophen-2-ylmethylamine thiophen-2-ylmethylamine NNP cord-276598-tm0yj2sn 533 36 and and CC cord-276598-tm0yj2sn 533 37 4-chlorobenzylamine 4-chlorobenzylamine CD cord-276598-tm0yj2sn 533 38 ) ) -RRB- cord-276598-tm0yj2sn 533 39 , , , cord-276598-tm0yj2sn 533 40 and and CC cord-276598-tm0yj2sn 533 41 heterocyclic heterocyclic JJ cord-276598-tm0yj2sn 533 42 amines amine NNS cord-276598-tm0yj2sn 533 43 ( ( -LRB- cord-276598-tm0yj2sn 533 44 e.g. e.g. RB cord-276598-tm0yj2sn 533 45 , , , cord-276598-tm0yj2sn 533 46 pyrrolidine pyrrolidine JJ cord-276598-tm0yj2sn 533 47 and and CC cord-276598-tm0yj2sn 533 48 morpholine morpholine NNP cord-276598-tm0yj2sn 533 49 ) ) -RRB- cord-276598-tm0yj2sn 533 50 . . . cord-276598-tm0yj2sn 534 1 Although although IN cord-276598-tm0yj2sn 534 2 the the DT cord-276598-tm0yj2sn 534 3 method method NN cord-276598-tm0yj2sn 534 4 circumvents circumvent VBZ cord-276598-tm0yj2sn 534 5 the the DT cord-276598-tm0yj2sn 534 6 use use NN cord-276598-tm0yj2sn 534 7 of of IN cord-276598-tm0yj2sn 534 8 metal metal NN cord-276598-tm0yj2sn 534 9 catalysts catalyst NNS cord-276598-tm0yj2sn 534 10 in in IN cord-276598-tm0yj2sn 534 11 the the DT cord-276598-tm0yj2sn 534 12 synthesis synthesis NN cord-276598-tm0yj2sn 534 13 , , , cord-276598-tm0yj2sn 534 14 the the DT cord-276598-tm0yj2sn 534 15 use use NN cord-276598-tm0yj2sn 534 16 of of IN cord-276598-tm0yj2sn 534 17 a a DT cord-276598-tm0yj2sn 534 18 hazardous hazardous JJ cord-276598-tm0yj2sn 534 19 azide azide NN cord-276598-tm0yj2sn 534 20 and and CC cord-276598-tm0yj2sn 534 21 high high JJ cord-276598-tm0yj2sn 534 22 temperature temperature NN cord-276598-tm0yj2sn 534 23 are be VBP cord-276598-tm0yj2sn 534 24 its -PRON- PRP$ cord-276598-tm0yj2sn 534 25 limitations limitation NNS cord-276598-tm0yj2sn 534 26 . . . cord-276598-tm0yj2sn 535 1 from from IN cord-276598-tm0yj2sn 535 2 the the DT cord-276598-tm0yj2sn 535 3 azide azide NN cord-276598-tm0yj2sn 535 4 ( ( -LRB- cord-276598-tm0yj2sn 535 5 Scheme scheme NN cord-276598-tm0yj2sn 535 6 13 13 CD cord-276598-tm0yj2sn 535 7 ) ) -RRB- cord-276598-tm0yj2sn 535 8 . . . cord-276598-tm0yj2sn 536 1 The the DT cord-276598-tm0yj2sn 536 2 residue residue NN cord-276598-tm0yj2sn 536 3 was be VBD cord-276598-tm0yj2sn 536 4 purified purify VBN cord-276598-tm0yj2sn 536 5 by by IN cord-276598-tm0yj2sn 536 6 column column NN cord-276598-tm0yj2sn 536 7 chromatography chromatography NN cord-276598-tm0yj2sn 536 8 ( ( -LRB- cord-276598-tm0yj2sn 536 9 on on IN cord-276598-tm0yj2sn 536 10 silica silica NN cord-276598-tm0yj2sn 536 11 ) ) -RRB- cord-276598-tm0yj2sn 536 12 to to TO cord-276598-tm0yj2sn 536 13 afford afford VB cord-276598-tm0yj2sn 536 14 the the DT cord-276598-tm0yj2sn 536 15 isolated isolate VBN cord-276598-tm0yj2sn 536 16 product product NN cord-276598-tm0yj2sn 536 17 in in IN cord-276598-tm0yj2sn 536 18 52 52 CD cord-276598-tm0yj2sn 536 19 - - SYM cord-276598-tm0yj2sn 536 20 92 92 CD cord-276598-tm0yj2sn 536 21 % % NN cord-276598-tm0yj2sn 536 22 yield yield NN cord-276598-tm0yj2sn 536 23 . . . cord-276598-tm0yj2sn 537 1 The the DT cord-276598-tm0yj2sn 537 2 scope scope NN cord-276598-tm0yj2sn 537 3 of of IN cord-276598-tm0yj2sn 537 4 the the DT cord-276598-tm0yj2sn 537 5 reaction reaction NN cord-276598-tm0yj2sn 537 6 was be VBD cord-276598-tm0yj2sn 537 7 examined examine VBN cord-276598-tm0yj2sn 537 8 by by IN cord-276598-tm0yj2sn 537 9 using use VBG cord-276598-tm0yj2sn 537 10 diphenyl diphenyl NNP cord-276598-tm0yj2sn 537 11 and and CC cord-276598-tm0yj2sn 537 12 diisopropyl diisopropyl NNP cord-276598-tm0yj2sn 537 13 phosphoryl phosphoryl NNP cord-276598-tm0yj2sn 537 14 azide azide NN cord-276598-tm0yj2sn 537 15 along along IN cord-276598-tm0yj2sn 537 16 with with IN cord-276598-tm0yj2sn 537 17 primary primary JJ cord-276598-tm0yj2sn 537 18 amines amine NNS cord-276598-tm0yj2sn 537 19 ( ( -LRB- cord-276598-tm0yj2sn 537 20 e.g. e.g. RB cord-276598-tm0yj2sn 537 21 , , , cord-276598-tm0yj2sn 537 22 isopropylamine isopropylamine NN cord-276598-tm0yj2sn 537 23 and and CC cord-276598-tm0yj2sn 537 24 t t NN cord-276598-tm0yj2sn 537 25 - - HYPH cord-276598-tm0yj2sn 537 26 butylamine butylamine NNP cord-276598-tm0yj2sn 537 27 ) ) -RRB- cord-276598-tm0yj2sn 537 28 , , , cord-276598-tm0yj2sn 537 29 substituted substitute VBN cord-276598-tm0yj2sn 537 30 primary primary JJ cord-276598-tm0yj2sn 537 31 amines amine NNS cord-276598-tm0yj2sn 537 32 ( ( -LRB- cord-276598-tm0yj2sn 537 33 e.g. e.g. RB cord-276598-tm0yj2sn 537 34 , , , cord-276598-tm0yj2sn 537 35 thiophen-2-ylmethylamine thiophen-2-ylmethylamine NNP cord-276598-tm0yj2sn 537 36 and and CC cord-276598-tm0yj2sn 537 37 4-chlorobenzylamine 4-chlorobenzylamine CD cord-276598-tm0yj2sn 537 38 ) ) -RRB- cord-276598-tm0yj2sn 537 39 , , , cord-276598-tm0yj2sn 537 40 and and CC cord-276598-tm0yj2sn 537 41 heterocyclic heterocyclic JJ cord-276598-tm0yj2sn 537 42 amines amine NNS cord-276598-tm0yj2sn 537 43 ( ( -LRB- cord-276598-tm0yj2sn 537 44 e.g. e.g. RB cord-276598-tm0yj2sn 537 45 , , , cord-276598-tm0yj2sn 537 46 pyrrolidine pyrrolidine JJ cord-276598-tm0yj2sn 537 47 and and CC cord-276598-tm0yj2sn 537 48 morpholine morpholine NNP cord-276598-tm0yj2sn 537 49 ) ) -RRB- cord-276598-tm0yj2sn 537 50 . . . cord-276598-tm0yj2sn 538 1 Although although IN cord-276598-tm0yj2sn 538 2 the the DT cord-276598-tm0yj2sn 538 3 method method NN cord-276598-tm0yj2sn 538 4 circumvents circumvent VBZ cord-276598-tm0yj2sn 538 5 the the DT cord-276598-tm0yj2sn 538 6 use use NN cord-276598-tm0yj2sn 538 7 of of IN cord-276598-tm0yj2sn 538 8 metal metal NN cord-276598-tm0yj2sn 538 9 catalysts catalyst NNS cord-276598-tm0yj2sn 538 10 in in IN cord-276598-tm0yj2sn 538 11 the the DT cord-276598-tm0yj2sn 538 12 synthesis synthesis NN cord-276598-tm0yj2sn 538 13 , , , cord-276598-tm0yj2sn 538 14 the the DT cord-276598-tm0yj2sn 538 15 use use NN cord-276598-tm0yj2sn 538 16 of of IN cord-276598-tm0yj2sn 538 17 a a DT cord-276598-tm0yj2sn 538 18 hazardous hazardous JJ cord-276598-tm0yj2sn 538 19 azide azide NN cord-276598-tm0yj2sn 538 20 and and CC cord-276598-tm0yj2sn 538 21 high high JJ cord-276598-tm0yj2sn 538 22 temperature temperature NN cord-276598-tm0yj2sn 538 23 are be VBP cord-276598-tm0yj2sn 538 24 its -PRON- PRP$ cord-276598-tm0yj2sn 538 25 limitations limitation NNS cord-276598-tm0yj2sn 538 26 . . . cord-276598-tm0yj2sn 539 1 Scheme scheme NN cord-276598-tm0yj2sn 539 2 13 13 CD cord-276598-tm0yj2sn 539 3 . . . cord-276598-tm0yj2sn 540 1 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 540 2 synthesis synthesis NN cord-276598-tm0yj2sn 540 3 from from IN cord-276598-tm0yj2sn 540 4 organic organic JJ cord-276598-tm0yj2sn 540 5 azide azide NN cord-276598-tm0yj2sn 540 6 and and CC cord-276598-tm0yj2sn 540 7 amine amine NN cord-276598-tm0yj2sn 540 8 . . . cord-276598-tm0yj2sn 541 1 Beifuss Beifuss NNP cord-276598-tm0yj2sn 541 2 et et NNP cord-276598-tm0yj2sn 541 3 al al NNP cord-276598-tm0yj2sn 541 4 . . NNP cord-276598-tm0yj2sn 541 5 reported report VBD cord-276598-tm0yj2sn 541 6 a a DT cord-276598-tm0yj2sn 541 7 microwave microwave NN cord-276598-tm0yj2sn 541 8 - - HYPH cord-276598-tm0yj2sn 541 9 assisted assist VBN cord-276598-tm0yj2sn 541 10 synthesis synthesis NN cord-276598-tm0yj2sn 541 11 of of IN cord-276598-tm0yj2sn 541 12 N n NN cord-276598-tm0yj2sn 541 13 - - HYPH cord-276598-tm0yj2sn 541 14 arylphosphoramidates arylphosphoramidate NNS cord-276598-tm0yj2sn 541 15 from from IN cord-276598-tm0yj2sn 541 16 nitrobenzene nitrobenzene NN cord-276598-tm0yj2sn 541 17 and and CC cord-276598-tm0yj2sn 541 18 ( ( -LRB- cord-276598-tm0yj2sn 541 19 RO)3P RO)3P NNP cord-276598-tm0yj2sn 541 20 ( ( -LRB- cord-276598-tm0yj2sn 541 21 R r NN cord-276598-tm0yj2sn 541 22 = = NN cord-276598-tm0yj2sn 541 23 alkyl alkyl NN cord-276598-tm0yj2sn 541 24 ) ) -RRB- cord-276598-tm0yj2sn 542 1 ( ( -LRB- cord-276598-tm0yj2sn 542 2 Scheme scheme NN cord-276598-tm0yj2sn 542 3 14 14 CD cord-276598-tm0yj2sn 542 4 ) ) -RRB- cord-276598-tm0yj2sn 542 5 [ [ -LRB- cord-276598-tm0yj2sn 542 6 118 118 CD cord-276598-tm0yj2sn 542 7 ] ] -RRB- cord-276598-tm0yj2sn 542 8 . . . cord-276598-tm0yj2sn 543 1 The the DT cord-276598-tm0yj2sn 543 2 crude crude JJ cord-276598-tm0yj2sn 543 3 residue residue NN cord-276598-tm0yj2sn 543 4 product product NN cord-276598-tm0yj2sn 543 5 was be VBD cord-276598-tm0yj2sn 543 6 purified purify VBN cord-276598-tm0yj2sn 543 7 by by IN cord-276598-tm0yj2sn 543 8 column column NN cord-276598-tm0yj2sn 543 9 chromatography chromatography NN cord-276598-tm0yj2sn 543 10 ( ( -LRB- cord-276598-tm0yj2sn 543 11 on on IN cord-276598-tm0yj2sn 543 12 silica silica NN cord-276598-tm0yj2sn 543 13 ) ) -RRB- cord-276598-tm0yj2sn 543 14 resulting result VBG cord-276598-tm0yj2sn 543 15 in in IN cord-276598-tm0yj2sn 543 16 pure pure JJ cord-276598-tm0yj2sn 543 17 P p NN cord-276598-tm0yj2sn 543 18 - - HYPH cord-276598-tm0yj2sn 543 19 Ns Ns NNP cord-276598-tm0yj2sn 543 20 with with IN cord-276598-tm0yj2sn 543 21 52 52 CD cord-276598-tm0yj2sn 543 22 - - SYM cord-276598-tm0yj2sn 543 23 79 79 CD cord-276598-tm0yj2sn 543 24 % % NN cord-276598-tm0yj2sn 543 25 isolated isolated JJ cord-276598-tm0yj2sn 543 26 yield yield NN cord-276598-tm0yj2sn 543 27 . . . cord-276598-tm0yj2sn 544 1 The the DT cord-276598-tm0yj2sn 544 2 scope scope NN cord-276598-tm0yj2sn 544 3 of of IN cord-276598-tm0yj2sn 544 4 the the DT cord-276598-tm0yj2sn 544 5 synthesis synthesis NN cord-276598-tm0yj2sn 544 6 was be VBD cord-276598-tm0yj2sn 544 7 investigated investigate VBN cord-276598-tm0yj2sn 544 8 using use VBG cord-276598-tm0yj2sn 544 9 trimethyl trimethyl NNP cord-276598-tm0yj2sn 544 10 or or CC cord-276598-tm0yj2sn 544 11 triethyl triethyl NNP cord-276598-tm0yj2sn 544 12 phosphite phosphite NNP cord-276598-tm0yj2sn 544 13 along along IN cord-276598-tm0yj2sn 544 14 with with IN cord-276598-tm0yj2sn 544 15 nitrobenzene nitrobenzene NNP cord-276598-tm0yj2sn 544 16 , , , cord-276598-tm0yj2sn 544 17 and and CC cord-276598-tm0yj2sn 544 18 mono mono NN cord-276598-tm0yj2sn 544 19 - - : cord-276598-tm0yj2sn 544 20 or or CC cord-276598-tm0yj2sn 544 21 di di NN cord-276598-tm0yj2sn 544 22 - - HYPH cord-276598-tm0yj2sn 544 23 substituted substitute VBN cord-276598-tm0yj2sn 544 24 nitrobenzenes nitrobenzene NNS cord-276598-tm0yj2sn 544 25 with with IN cord-276598-tm0yj2sn 544 26 substitution substitution NN cord-276598-tm0yj2sn 544 27 such such JJ cord-276598-tm0yj2sn 544 28 as as IN cord-276598-tm0yj2sn 544 29 Me -PRON- PRP cord-276598-tm0yj2sn 544 30 , , , cord-276598-tm0yj2sn 544 31 OMe OMe NNS cord-276598-tm0yj2sn 544 32 , , , cord-276598-tm0yj2sn 544 33 Cl Cl NNP cord-276598-tm0yj2sn 544 34 , , , cord-276598-tm0yj2sn 544 35 Br Br NNP cord-276598-tm0yj2sn 544 36 , , , cord-276598-tm0yj2sn 544 37 or or CC cord-276598-tm0yj2sn 544 38 CN CN NNP cord-276598-tm0yj2sn 544 39 groups group NNS cord-276598-tm0yj2sn 544 40 . . . cord-276598-tm0yj2sn 545 1 This this DT cord-276598-tm0yj2sn 545 2 method method NN cord-276598-tm0yj2sn 545 3 is be VBZ cord-276598-tm0yj2sn 545 4 attractive attractive JJ cord-276598-tm0yj2sn 545 5 because because IN cord-276598-tm0yj2sn 545 6 it -PRON- PRP cord-276598-tm0yj2sn 545 7 provides provide VBZ cord-276598-tm0yj2sn 545 8 a a DT cord-276598-tm0yj2sn 545 9 different different JJ cord-276598-tm0yj2sn 545 10 route route NN cord-276598-tm0yj2sn 545 11 to to IN cord-276598-tm0yj2sn 545 12 P p NN cord-276598-tm0yj2sn 545 13 - - HYPH cord-276598-tm0yj2sn 545 14 Ns Ns NNP cord-276598-tm0yj2sn 545 15 using use VBG cord-276598-tm0yj2sn 545 16 nitro nitro NN cord-276598-tm0yj2sn 545 17 compounds compound NNS cord-276598-tm0yj2sn 545 18 instead instead RB cord-276598-tm0yj2sn 545 19 of of IN cord-276598-tm0yj2sn 545 20 the the DT cord-276598-tm0yj2sn 545 21 conventional conventional JJ cord-276598-tm0yj2sn 545 22 amines amine NNS cord-276598-tm0yj2sn 545 23 . . . cord-276598-tm0yj2sn 546 1 Nonetheless nonetheless RB cord-276598-tm0yj2sn 546 2 , , , cord-276598-tm0yj2sn 546 3 the the DT cord-276598-tm0yj2sn 546 4 high high JJ cord-276598-tm0yj2sn 546 5 temperature temperature NN cord-276598-tm0yj2sn 546 6 and and CC cord-276598-tm0yj2sn 546 7 amount amount NN cord-276598-tm0yj2sn 546 8 of of IN cord-276598-tm0yj2sn 546 9 energy energy NN cord-276598-tm0yj2sn 546 10 required require VBN cord-276598-tm0yj2sn 546 11 during during IN cord-276598-tm0yj2sn 546 12 the the DT cord-276598-tm0yj2sn 546 13 synthesis synthesis NN cord-276598-tm0yj2sn 546 14 are be VBP cord-276598-tm0yj2sn 546 15 the the DT cord-276598-tm0yj2sn 546 16 obvious obvious JJ cord-276598-tm0yj2sn 546 17 limitations limitation NNS cord-276598-tm0yj2sn 546 18 . . . cord-276598-tm0yj2sn 546 19 _SP cord-276598-tm0yj2sn 547 1 Beifuss Beifuss NNP cord-276598-tm0yj2sn 547 2 et et NNP cord-276598-tm0yj2sn 547 3 al al NNP cord-276598-tm0yj2sn 547 4 . . NNP cord-276598-tm0yj2sn 547 5 reported report VBD cord-276598-tm0yj2sn 547 6 a a DT cord-276598-tm0yj2sn 547 7 microwave microwave NN cord-276598-tm0yj2sn 547 8 - - HYPH cord-276598-tm0yj2sn 547 9 assisted assist VBN cord-276598-tm0yj2sn 547 10 synthesis synthesis NN cord-276598-tm0yj2sn 547 11 of of IN cord-276598-tm0yj2sn 547 12 N n NN cord-276598-tm0yj2sn 547 13 - - HYPH cord-276598-tm0yj2sn 547 14 arylphosphoramidates arylphosphoramidate NNS cord-276598-tm0yj2sn 547 15 from from IN cord-276598-tm0yj2sn 547 16 nitrobenzene nitrobenzene NN cord-276598-tm0yj2sn 547 17 and and CC cord-276598-tm0yj2sn 547 18 ( ( -LRB- cord-276598-tm0yj2sn 547 19 RO RO NNP cord-276598-tm0yj2sn 547 20 ) ) -RRB- cord-276598-tm0yj2sn 547 21 3 3 CD cord-276598-tm0yj2sn 547 22 P p NN cord-276598-tm0yj2sn 547 23 ( ( -LRB- cord-276598-tm0yj2sn 547 24 R r NN cord-276598-tm0yj2sn 547 25 = = NN cord-276598-tm0yj2sn 547 26 alkyl alkyl NN cord-276598-tm0yj2sn 547 27 ) ) -RRB- cord-276598-tm0yj2sn 548 1 ( ( -LRB- cord-276598-tm0yj2sn 548 2 Scheme scheme NN cord-276598-tm0yj2sn 548 3 14 14 CD cord-276598-tm0yj2sn 548 4 ) ) -RRB- cord-276598-tm0yj2sn 548 5 [ [ -LRB- cord-276598-tm0yj2sn 548 6 118 118 CD cord-276598-tm0yj2sn 548 7 ] ] -RRB- cord-276598-tm0yj2sn 548 8 . . . cord-276598-tm0yj2sn 549 1 The the DT cord-276598-tm0yj2sn 549 2 crude crude JJ cord-276598-tm0yj2sn 549 3 residue residue NN cord-276598-tm0yj2sn 549 4 product product NN cord-276598-tm0yj2sn 549 5 was be VBD cord-276598-tm0yj2sn 549 6 purified purify VBN cord-276598-tm0yj2sn 549 7 by by IN cord-276598-tm0yj2sn 549 8 column column NN cord-276598-tm0yj2sn 549 9 chromatography chromatography NN cord-276598-tm0yj2sn 549 10 ( ( -LRB- cord-276598-tm0yj2sn 549 11 on on IN cord-276598-tm0yj2sn 549 12 silica silica NN cord-276598-tm0yj2sn 549 13 ) ) -RRB- cord-276598-tm0yj2sn 549 14 resulting result VBG cord-276598-tm0yj2sn 549 15 in in IN cord-276598-tm0yj2sn 549 16 pure pure JJ cord-276598-tm0yj2sn 549 17 P p NN cord-276598-tm0yj2sn 549 18 - - HYPH cord-276598-tm0yj2sn 549 19 Ns Ns NNP cord-276598-tm0yj2sn 549 20 with with IN cord-276598-tm0yj2sn 549 21 52 52 CD cord-276598-tm0yj2sn 549 22 - - SYM cord-276598-tm0yj2sn 549 23 79 79 CD cord-276598-tm0yj2sn 549 24 % % NN cord-276598-tm0yj2sn 549 25 isolated isolated JJ cord-276598-tm0yj2sn 549 26 yield yield NN cord-276598-tm0yj2sn 549 27 . . . cord-276598-tm0yj2sn 550 1 The the DT cord-276598-tm0yj2sn 550 2 scope scope NN cord-276598-tm0yj2sn 550 3 of of IN cord-276598-tm0yj2sn 550 4 the the DT cord-276598-tm0yj2sn 550 5 synthesis synthesis NN cord-276598-tm0yj2sn 550 6 was be VBD cord-276598-tm0yj2sn 550 7 investigated investigate VBN cord-276598-tm0yj2sn 550 8 using use VBG cord-276598-tm0yj2sn 550 9 trimethyl trimethyl NNP cord-276598-tm0yj2sn 550 10 or or CC cord-276598-tm0yj2sn 550 11 triethyl triethyl NNP cord-276598-tm0yj2sn 550 12 phosphite phosphite NNP cord-276598-tm0yj2sn 550 13 along along IN cord-276598-tm0yj2sn 550 14 with with IN cord-276598-tm0yj2sn 550 15 nitrobenzene nitrobenzene NNP cord-276598-tm0yj2sn 550 16 , , , cord-276598-tm0yj2sn 550 17 and and CC cord-276598-tm0yj2sn 550 18 mono mono NN cord-276598-tm0yj2sn 550 19 - - : cord-276598-tm0yj2sn 550 20 or or CC cord-276598-tm0yj2sn 550 21 di di NN cord-276598-tm0yj2sn 550 22 - - HYPH cord-276598-tm0yj2sn 550 23 substituted substitute VBN cord-276598-tm0yj2sn 550 24 nitrobenzenes nitrobenzene NNS cord-276598-tm0yj2sn 550 25 with with IN cord-276598-tm0yj2sn 550 26 substitution substitution NN cord-276598-tm0yj2sn 550 27 such such JJ cord-276598-tm0yj2sn 550 28 as as IN cord-276598-tm0yj2sn 550 29 Me -PRON- PRP cord-276598-tm0yj2sn 550 30 , , , cord-276598-tm0yj2sn 550 31 OMe OMe NNS cord-276598-tm0yj2sn 550 32 , , , cord-276598-tm0yj2sn 550 33 Cl Cl NNP cord-276598-tm0yj2sn 550 34 , , , cord-276598-tm0yj2sn 550 35 Br Br NNP cord-276598-tm0yj2sn 550 36 , , , cord-276598-tm0yj2sn 550 37 or or CC cord-276598-tm0yj2sn 550 38 CN CN NNP cord-276598-tm0yj2sn 550 39 groups group NNS cord-276598-tm0yj2sn 550 40 . . . cord-276598-tm0yj2sn 551 1 This this DT cord-276598-tm0yj2sn 551 2 method method NN cord-276598-tm0yj2sn 551 3 is be VBZ cord-276598-tm0yj2sn 551 4 attractive attractive JJ cord-276598-tm0yj2sn 551 5 because because IN cord-276598-tm0yj2sn 551 6 it -PRON- PRP cord-276598-tm0yj2sn 551 7 provides provide VBZ cord-276598-tm0yj2sn 551 8 a a DT cord-276598-tm0yj2sn 551 9 different different JJ cord-276598-tm0yj2sn 551 10 route route NN cord-276598-tm0yj2sn 551 11 to to IN cord-276598-tm0yj2sn 551 12 P p NN cord-276598-tm0yj2sn 551 13 - - HYPH cord-276598-tm0yj2sn 551 14 Ns Ns NNP cord-276598-tm0yj2sn 551 15 using use VBG cord-276598-tm0yj2sn 551 16 nitro nitro NN cord-276598-tm0yj2sn 551 17 compounds compound NNS cord-276598-tm0yj2sn 551 18 instead instead RB cord-276598-tm0yj2sn 551 19 of of IN cord-276598-tm0yj2sn 551 20 the the DT cord-276598-tm0yj2sn 551 21 conventional conventional JJ cord-276598-tm0yj2sn 551 22 amines amine NNS cord-276598-tm0yj2sn 551 23 . . . cord-276598-tm0yj2sn 552 1 Nonetheless nonetheless RB cord-276598-tm0yj2sn 552 2 , , , cord-276598-tm0yj2sn 552 3 the the DT cord-276598-tm0yj2sn 552 4 high high JJ cord-276598-tm0yj2sn 552 5 temperature temperature NN cord-276598-tm0yj2sn 552 6 and and CC cord-276598-tm0yj2sn 552 7 amount amount NN cord-276598-tm0yj2sn 552 8 of of IN cord-276598-tm0yj2sn 552 9 energy energy NN cord-276598-tm0yj2sn 552 10 required require VBN cord-276598-tm0yj2sn 552 11 during during IN cord-276598-tm0yj2sn 552 12 the the DT cord-276598-tm0yj2sn 552 13 synthesis synthesis NN cord-276598-tm0yj2sn 552 14 are be VBP cord-276598-tm0yj2sn 552 15 the the DT cord-276598-tm0yj2sn 552 16 obvious obvious JJ cord-276598-tm0yj2sn 552 17 limitations limitation NNS cord-276598-tm0yj2sn 552 18 . . . cord-276598-tm0yj2sn 553 1 afford afford VB cord-276598-tm0yj2sn 553 2 the the DT cord-276598-tm0yj2sn 553 3 isolated isolate VBN cord-276598-tm0yj2sn 553 4 product product NN cord-276598-tm0yj2sn 553 5 in in IN cord-276598-tm0yj2sn 553 6 52 52 CD cord-276598-tm0yj2sn 553 7 - - SYM cord-276598-tm0yj2sn 553 8 92 92 CD cord-276598-tm0yj2sn 553 9 % % NN cord-276598-tm0yj2sn 553 10 yield yield NN cord-276598-tm0yj2sn 553 11 . . . cord-276598-tm0yj2sn 554 1 The the DT cord-276598-tm0yj2sn 554 2 scope scope NN cord-276598-tm0yj2sn 554 3 of of IN cord-276598-tm0yj2sn 554 4 the the DT cord-276598-tm0yj2sn 554 5 reaction reaction NN cord-276598-tm0yj2sn 554 6 was be VBD cord-276598-tm0yj2sn 554 7 examined examine VBN cord-276598-tm0yj2sn 554 8 by by IN cord-276598-tm0yj2sn 554 9 using use VBG cord-276598-tm0yj2sn 554 10 diphenyl diphenyl NNP cord-276598-tm0yj2sn 554 11 and and CC cord-276598-tm0yj2sn 554 12 diisopropyl diisopropyl NNP cord-276598-tm0yj2sn 554 13 phosphoryl phosphoryl NNP cord-276598-tm0yj2sn 554 14 azide azide NN cord-276598-tm0yj2sn 554 15 along along IN cord-276598-tm0yj2sn 554 16 with with IN cord-276598-tm0yj2sn 554 17 primary primary JJ cord-276598-tm0yj2sn 554 18 amines amine NNS cord-276598-tm0yj2sn 554 19 ( ( -LRB- cord-276598-tm0yj2sn 554 20 e.g. e.g. RB cord-276598-tm0yj2sn 554 21 , , , cord-276598-tm0yj2sn 554 22 isopropylamine isopropylamine NN cord-276598-tm0yj2sn 554 23 and and CC cord-276598-tm0yj2sn 554 24 t t NN cord-276598-tm0yj2sn 554 25 - - HYPH cord-276598-tm0yj2sn 554 26 butylamine butylamine NNP cord-276598-tm0yj2sn 554 27 ) ) -RRB- cord-276598-tm0yj2sn 554 28 , , , cord-276598-tm0yj2sn 554 29 substituted substitute VBN cord-276598-tm0yj2sn 554 30 primary primary JJ cord-276598-tm0yj2sn 554 31 amines amine NNS cord-276598-tm0yj2sn 554 32 ( ( -LRB- cord-276598-tm0yj2sn 554 33 e.g. e.g. RB cord-276598-tm0yj2sn 554 34 , , , cord-276598-tm0yj2sn 554 35 thiophen-2-ylmethylamine thiophen-2-ylmethylamine NNP cord-276598-tm0yj2sn 554 36 and and CC cord-276598-tm0yj2sn 554 37 4-chlorobenzylamine 4-chlorobenzylamine CD cord-276598-tm0yj2sn 554 38 ) ) -RRB- cord-276598-tm0yj2sn 554 39 , , , cord-276598-tm0yj2sn 554 40 and and CC cord-276598-tm0yj2sn 554 41 heterocyclic heterocyclic JJ cord-276598-tm0yj2sn 554 42 amines amine NNS cord-276598-tm0yj2sn 554 43 ( ( -LRB- cord-276598-tm0yj2sn 554 44 e.g. e.g. RB cord-276598-tm0yj2sn 554 45 , , , cord-276598-tm0yj2sn 554 46 pyrrolidine pyrrolidine JJ cord-276598-tm0yj2sn 554 47 and and CC cord-276598-tm0yj2sn 554 48 morpholine morpholine NNP cord-276598-tm0yj2sn 554 49 ) ) -RRB- cord-276598-tm0yj2sn 554 50 . . . cord-276598-tm0yj2sn 555 1 Although although IN cord-276598-tm0yj2sn 555 2 the the DT cord-276598-tm0yj2sn 555 3 method method NN cord-276598-tm0yj2sn 555 4 circumvents circumvent VBZ cord-276598-tm0yj2sn 555 5 the the DT cord-276598-tm0yj2sn 555 6 use use NN cord-276598-tm0yj2sn 555 7 of of IN cord-276598-tm0yj2sn 555 8 metal metal NN cord-276598-tm0yj2sn 555 9 catalysts catalyst NNS cord-276598-tm0yj2sn 555 10 in in IN cord-276598-tm0yj2sn 555 11 the the DT cord-276598-tm0yj2sn 555 12 synthesis synthesis NN cord-276598-tm0yj2sn 555 13 , , , cord-276598-tm0yj2sn 555 14 the the DT cord-276598-tm0yj2sn 555 15 use use NN cord-276598-tm0yj2sn 555 16 of of IN cord-276598-tm0yj2sn 555 17 a a DT cord-276598-tm0yj2sn 555 18 hazardous hazardous JJ cord-276598-tm0yj2sn 555 19 azide azide NN cord-276598-tm0yj2sn 555 20 and and CC cord-276598-tm0yj2sn 555 21 high high JJ cord-276598-tm0yj2sn 555 22 temperature temperature NN cord-276598-tm0yj2sn 555 23 are be VBP cord-276598-tm0yj2sn 555 24 its -PRON- PRP$ cord-276598-tm0yj2sn 555 25 limitations limitation NNS cord-276598-tm0yj2sn 555 26 . . . cord-276598-tm0yj2sn 556 1 Scheme scheme NN cord-276598-tm0yj2sn 556 2 13 13 CD cord-276598-tm0yj2sn 556 3 . . . cord-276598-tm0yj2sn 557 1 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 557 2 synthesis synthesis NN cord-276598-tm0yj2sn 557 3 from from IN cord-276598-tm0yj2sn 557 4 organic organic JJ cord-276598-tm0yj2sn 557 5 azide azide NN cord-276598-tm0yj2sn 557 6 and and CC cord-276598-tm0yj2sn 557 7 amine amine NN cord-276598-tm0yj2sn 557 8 . . . cord-276598-tm0yj2sn 558 1 Beifuss Beifuss NNP cord-276598-tm0yj2sn 558 2 et et NNP cord-276598-tm0yj2sn 558 3 al al NNP cord-276598-tm0yj2sn 558 4 . . NNP cord-276598-tm0yj2sn 558 5 reported report VBD cord-276598-tm0yj2sn 558 6 a a DT cord-276598-tm0yj2sn 558 7 microwave microwave NN cord-276598-tm0yj2sn 558 8 - - HYPH cord-276598-tm0yj2sn 558 9 assisted assist VBN cord-276598-tm0yj2sn 558 10 synthesis synthesis NN cord-276598-tm0yj2sn 558 11 of of IN cord-276598-tm0yj2sn 558 12 N n NN cord-276598-tm0yj2sn 558 13 - - HYPH cord-276598-tm0yj2sn 558 14 arylphosphoramidates arylphosphoramidate NNS cord-276598-tm0yj2sn 558 15 from from IN cord-276598-tm0yj2sn 558 16 nitrobenzene nitrobenzene NN cord-276598-tm0yj2sn 558 17 and and CC cord-276598-tm0yj2sn 558 18 ( ( -LRB- cord-276598-tm0yj2sn 558 19 RO)3P RO)3P NNP cord-276598-tm0yj2sn 558 20 ( ( -LRB- cord-276598-tm0yj2sn 558 21 R r NN cord-276598-tm0yj2sn 558 22 = = NN cord-276598-tm0yj2sn 558 23 alkyl alkyl NN cord-276598-tm0yj2sn 558 24 ) ) -RRB- cord-276598-tm0yj2sn 559 1 ( ( -LRB- cord-276598-tm0yj2sn 559 2 Scheme scheme NN cord-276598-tm0yj2sn 559 3 14 14 CD cord-276598-tm0yj2sn 559 4 ) ) -RRB- cord-276598-tm0yj2sn 559 5 [ [ -LRB- cord-276598-tm0yj2sn 559 6 118 118 CD cord-276598-tm0yj2sn 559 7 ] ] -RRB- cord-276598-tm0yj2sn 559 8 . . . cord-276598-tm0yj2sn 560 1 The the DT cord-276598-tm0yj2sn 560 2 crude crude JJ cord-276598-tm0yj2sn 560 3 residue residue NN cord-276598-tm0yj2sn 560 4 product product NN cord-276598-tm0yj2sn 560 5 was be VBD cord-276598-tm0yj2sn 560 6 purified purify VBN cord-276598-tm0yj2sn 560 7 by by IN cord-276598-tm0yj2sn 560 8 column column NN cord-276598-tm0yj2sn 560 9 chromatography chromatography NN cord-276598-tm0yj2sn 560 10 ( ( -LRB- cord-276598-tm0yj2sn 560 11 on on IN cord-276598-tm0yj2sn 560 12 silica silica NN cord-276598-tm0yj2sn 560 13 ) ) -RRB- cord-276598-tm0yj2sn 560 14 resulting result VBG cord-276598-tm0yj2sn 560 15 in in IN cord-276598-tm0yj2sn 560 16 pure pure JJ cord-276598-tm0yj2sn 560 17 P p NN cord-276598-tm0yj2sn 560 18 - - HYPH cord-276598-tm0yj2sn 560 19 Ns Ns NNP cord-276598-tm0yj2sn 560 20 with with IN cord-276598-tm0yj2sn 560 21 52 52 CD cord-276598-tm0yj2sn 560 22 - - SYM cord-276598-tm0yj2sn 560 23 79 79 CD cord-276598-tm0yj2sn 560 24 % % NN cord-276598-tm0yj2sn 560 25 isolated isolated JJ cord-276598-tm0yj2sn 560 26 yield yield NN cord-276598-tm0yj2sn 560 27 . . . cord-276598-tm0yj2sn 561 1 The the DT cord-276598-tm0yj2sn 561 2 scope scope NN cord-276598-tm0yj2sn 561 3 of of IN cord-276598-tm0yj2sn 561 4 the the DT cord-276598-tm0yj2sn 561 5 synthesis synthesis NN cord-276598-tm0yj2sn 561 6 was be VBD cord-276598-tm0yj2sn 561 7 investigated investigate VBN cord-276598-tm0yj2sn 561 8 using use VBG cord-276598-tm0yj2sn 561 9 trimethyl trimethyl NNP cord-276598-tm0yj2sn 561 10 or or CC cord-276598-tm0yj2sn 561 11 triethyl triethyl NNP cord-276598-tm0yj2sn 561 12 phosphite phosphite NNP cord-276598-tm0yj2sn 561 13 along along IN cord-276598-tm0yj2sn 561 14 with with IN cord-276598-tm0yj2sn 561 15 nitrobenzene nitrobenzene NNP cord-276598-tm0yj2sn 561 16 , , , cord-276598-tm0yj2sn 561 17 and and CC cord-276598-tm0yj2sn 561 18 mono mono NN cord-276598-tm0yj2sn 561 19 - - : cord-276598-tm0yj2sn 561 20 or or CC cord-276598-tm0yj2sn 561 21 di di NN cord-276598-tm0yj2sn 561 22 - - HYPH cord-276598-tm0yj2sn 561 23 substituted substitute VBN cord-276598-tm0yj2sn 561 24 nitrobenzenes nitrobenzene NNS cord-276598-tm0yj2sn 561 25 with with IN cord-276598-tm0yj2sn 561 26 substitution substitution NN cord-276598-tm0yj2sn 561 27 such such JJ cord-276598-tm0yj2sn 561 28 as as IN cord-276598-tm0yj2sn 561 29 Me -PRON- PRP cord-276598-tm0yj2sn 561 30 , , , cord-276598-tm0yj2sn 561 31 OMe OMe NNS cord-276598-tm0yj2sn 561 32 , , , cord-276598-tm0yj2sn 561 33 Cl Cl NNP cord-276598-tm0yj2sn 561 34 , , , cord-276598-tm0yj2sn 561 35 Br Br NNP cord-276598-tm0yj2sn 561 36 , , , cord-276598-tm0yj2sn 561 37 or or CC cord-276598-tm0yj2sn 561 38 CN CN NNP cord-276598-tm0yj2sn 561 39 groups group NNS cord-276598-tm0yj2sn 561 40 . . . cord-276598-tm0yj2sn 562 1 This this DT cord-276598-tm0yj2sn 562 2 method method NN cord-276598-tm0yj2sn 562 3 is be VBZ cord-276598-tm0yj2sn 562 4 attractive attractive JJ cord-276598-tm0yj2sn 562 5 because because IN cord-276598-tm0yj2sn 562 6 it -PRON- PRP cord-276598-tm0yj2sn 562 7 provides provide VBZ cord-276598-tm0yj2sn 562 8 a a DT cord-276598-tm0yj2sn 562 9 different different JJ cord-276598-tm0yj2sn 562 10 route route NN cord-276598-tm0yj2sn 562 11 to to IN cord-276598-tm0yj2sn 562 12 P p NN cord-276598-tm0yj2sn 562 13 - - HYPH cord-276598-tm0yj2sn 562 14 Ns Ns NNP cord-276598-tm0yj2sn 562 15 using use VBG cord-276598-tm0yj2sn 562 16 nitro nitro NN cord-276598-tm0yj2sn 562 17 compounds compound NNS cord-276598-tm0yj2sn 562 18 instead instead RB cord-276598-tm0yj2sn 562 19 of of IN cord-276598-tm0yj2sn 562 20 the the DT cord-276598-tm0yj2sn 562 21 conventional conventional JJ cord-276598-tm0yj2sn 562 22 amines amine NNS cord-276598-tm0yj2sn 562 23 . . . cord-276598-tm0yj2sn 563 1 Nonetheless nonetheless RB cord-276598-tm0yj2sn 563 2 , , , cord-276598-tm0yj2sn 563 3 the the DT cord-276598-tm0yj2sn 563 4 high high JJ cord-276598-tm0yj2sn 563 5 temperature temperature NN cord-276598-tm0yj2sn 563 6 and and CC cord-276598-tm0yj2sn 563 7 amount amount NN cord-276598-tm0yj2sn 563 8 of of IN cord-276598-tm0yj2sn 563 9 energy energy NN cord-276598-tm0yj2sn 563 10 required require VBN cord-276598-tm0yj2sn 563 11 during during IN cord-276598-tm0yj2sn 563 12 the the DT cord-276598-tm0yj2sn 563 13 synthesis synthesis NN cord-276598-tm0yj2sn 563 14 are be VBP cord-276598-tm0yj2sn 563 15 the the DT cord-276598-tm0yj2sn 563 16 obvious obvious JJ cord-276598-tm0yj2sn 563 17 limitations limitation NNS cord-276598-tm0yj2sn 563 18 . . . cord-276598-tm0yj2sn 563 19 _SP cord-276598-tm0yj2sn 564 1 Hackenberger Hackenberger NNP cord-276598-tm0yj2sn 564 2 et et NNP cord-276598-tm0yj2sn 564 3 al al NNP cord-276598-tm0yj2sn 564 4 . . . cord-276598-tm0yj2sn 565 1 synthesized synthesize VBN cord-276598-tm0yj2sn 565 2 P P NNP cord-276598-tm0yj2sn 565 3 - - HYPH cord-276598-tm0yj2sn 565 4 N n CD cord-276598-tm0yj2sn 565 5 compounds compound NNS cord-276598-tm0yj2sn 565 6 from from IN cord-276598-tm0yj2sn 565 7 organic organic JJ cord-276598-tm0yj2sn 565 8 azide azide NN cord-276598-tm0yj2sn 565 9 derivatives derivative NNS cord-276598-tm0yj2sn 565 10 and and CC cord-276598-tm0yj2sn 565 11 ( ( -LRB- cord-276598-tm0yj2sn 565 12 RO RO NNP cord-276598-tm0yj2sn 565 13 ) ) -RRB- cord-276598-tm0yj2sn 565 14 3 3 CD cord-276598-tm0yj2sn 565 15 P p NN cord-276598-tm0yj2sn 565 16 ( ( -LRB- cord-276598-tm0yj2sn 565 17 R r NN cord-276598-tm0yj2sn 565 18 = = NN cord-276598-tm0yj2sn 565 19 alkyl alkyl NN cord-276598-tm0yj2sn 565 20 ) ) -RRB- cord-276598-tm0yj2sn 566 1 after after IN cord-276598-tm0yj2sn 566 2 Lewis Lewis NNP cord-276598-tm0yj2sn 566 3 acid acid NN cord-276598-tm0yj2sn 566 4 - - HYPH cord-276598-tm0yj2sn 566 5 catalyzed catalyze VBN cord-276598-tm0yj2sn 566 6 rearrangement rearrangement NN cord-276598-tm0yj2sn 566 7 ( ( -LRB- cord-276598-tm0yj2sn 566 8 Scheme scheme NN cord-276598-tm0yj2sn 566 9 15 15 CD cord-276598-tm0yj2sn 566 10 ) ) -RRB- cord-276598-tm0yj2sn 566 11 [ [ -LRB- cord-276598-tm0yj2sn 566 12 119 119 CD cord-276598-tm0yj2sn 566 13 ] ] -RRB- cord-276598-tm0yj2sn 566 14 . . . cord-276598-tm0yj2sn 567 1 The the DT cord-276598-tm0yj2sn 567 2 crude crude JJ cord-276598-tm0yj2sn 567 3 product product NN cord-276598-tm0yj2sn 567 4 was be VBD cord-276598-tm0yj2sn 567 5 concentrated concentrate VBN cord-276598-tm0yj2sn 567 6 under under IN cord-276598-tm0yj2sn 567 7 reduced reduce VBN cord-276598-tm0yj2sn 567 8 pressure pressure NN cord-276598-tm0yj2sn 567 9 , , , cord-276598-tm0yj2sn 567 10 and and CC cord-276598-tm0yj2sn 567 11 the the DT cord-276598-tm0yj2sn 567 12 desired desire VBN cord-276598-tm0yj2sn 567 13 product product NN cord-276598-tm0yj2sn 567 14 was be VBD cord-276598-tm0yj2sn 567 15 isolated isolate VBN cord-276598-tm0yj2sn 567 16 ( ( -LRB- cord-276598-tm0yj2sn 567 17 63 63 CD cord-276598-tm0yj2sn 567 18 - - SYM cord-276598-tm0yj2sn 567 19 98 98 CD cord-276598-tm0yj2sn 567 20 % % NN cord-276598-tm0yj2sn 567 21 yield yield NN cord-276598-tm0yj2sn 567 22 ) ) -RRB- cord-276598-tm0yj2sn 567 23 through through IN cord-276598-tm0yj2sn 567 24 column column NN cord-276598-tm0yj2sn 567 25 chromatography chromatography NN cord-276598-tm0yj2sn 567 26 ( ( -LRB- cord-276598-tm0yj2sn 567 27 on on IN cord-276598-tm0yj2sn 567 28 silica silica NN cord-276598-tm0yj2sn 567 29 ) ) -RRB- cord-276598-tm0yj2sn 567 30 . . . cord-276598-tm0yj2sn 568 1 Triethyl Triethyl NNP cord-276598-tm0yj2sn 568 2 or or CC cord-276598-tm0yj2sn 568 3 trimethyl trimethyl NNP cord-276598-tm0yj2sn 568 4 phosphite phosphite NNP cord-276598-tm0yj2sn 568 5 were be VBD cord-276598-tm0yj2sn 568 6 used use VBN cord-276598-tm0yj2sn 568 7 as as IN cord-276598-tm0yj2sn 568 8 the the DT cord-276598-tm0yj2sn 568 9 P p NN cord-276598-tm0yj2sn 568 10 - - HYPH cord-276598-tm0yj2sn 568 11 source source NN cord-276598-tm0yj2sn 568 12 along along IN cord-276598-tm0yj2sn 568 13 with with IN cord-276598-tm0yj2sn 568 14 organic organic JJ cord-276598-tm0yj2sn 568 15 azide azide NN cord-276598-tm0yj2sn 568 16 derivatives derivative NNS cord-276598-tm0yj2sn 568 17 such such JJ cord-276598-tm0yj2sn 568 18 as as IN cord-276598-tm0yj2sn 568 19 ( ( -LRB- cord-276598-tm0yj2sn 568 20 azidomethyl)benzene azidomethyl)benzene NNP cord-276598-tm0yj2sn 568 21 , , , cord-276598-tm0yj2sn 568 22 azidocyclohexane azidocyclohexane NNP cord-276598-tm0yj2sn 568 23 , , , cord-276598-tm0yj2sn 568 24 ( ( -LRB- cord-276598-tm0yj2sn 568 25 2-azidopropan-2-yl)benzene 2-azidopropan-2-yl)benzene CD cord-276598-tm0yj2sn 568 26 , , , cord-276598-tm0yj2sn 568 27 azidobenzene azidobenzene NN cord-276598-tm0yj2sn 568 28 , , , cord-276598-tm0yj2sn 568 29 ethyl ethyl NNP cord-276598-tm0yj2sn 568 30 2-azidoacetate 2-azidoacetate CD cord-276598-tm0yj2sn 568 31 , , , cord-276598-tm0yj2sn 568 32 1-azidodecane 1-azidodecane CD cord-276598-tm0yj2sn 568 33 , , , cord-276598-tm0yj2sn 568 34 ( ( -LRB- cord-276598-tm0yj2sn 568 35 azidomethylene)dibenzene azidomethylene)dibenzene NNP cord-276598-tm0yj2sn 568 36 , , , cord-276598-tm0yj2sn 568 37 and and CC cord-276598-tm0yj2sn 568 38 ( ( -LRB- cord-276598-tm0yj2sn 568 39 3-azidoprop-1-en-1-yl)benzene 3-azidoprop-1-en-1-yl)benzene CD cord-276598-tm0yj2sn 568 40 . . . cord-276598-tm0yj2sn 569 1 [ [ -LRB- cord-276598-tm0yj2sn 569 2 119 119 CD cord-276598-tm0yj2sn 569 3 ] ] -RRB- cord-276598-tm0yj2sn 569 4 . . . cord-276598-tm0yj2sn 570 1 The the DT cord-276598-tm0yj2sn 570 2 crude crude JJ cord-276598-tm0yj2sn 570 3 product product NN cord-276598-tm0yj2sn 570 4 was be VBD cord-276598-tm0yj2sn 570 5 concentrated concentrate VBN cord-276598-tm0yj2sn 570 6 under under IN cord-276598-tm0yj2sn 570 7 reduced reduce VBN cord-276598-tm0yj2sn 570 8 pressure pressure NN cord-276598-tm0yj2sn 570 9 , , , cord-276598-tm0yj2sn 570 10 and and CC cord-276598-tm0yj2sn 570 11 the the DT cord-276598-tm0yj2sn 570 12 desired desire VBN cord-276598-tm0yj2sn 570 13 product product NN cord-276598-tm0yj2sn 570 14 was be VBD cord-276598-tm0yj2sn 570 15 isolated isolate VBN cord-276598-tm0yj2sn 570 16 ( ( -LRB- cord-276598-tm0yj2sn 570 17 63 63 CD cord-276598-tm0yj2sn 570 18 - - SYM cord-276598-tm0yj2sn 570 19 98 98 CD cord-276598-tm0yj2sn 570 20 % % NN cord-276598-tm0yj2sn 570 21 yield yield NN cord-276598-tm0yj2sn 570 22 ) ) -RRB- cord-276598-tm0yj2sn 570 23 through through IN cord-276598-tm0yj2sn 570 24 column column NN cord-276598-tm0yj2sn 570 25 chromatography chromatography NN cord-276598-tm0yj2sn 570 26 ( ( -LRB- cord-276598-tm0yj2sn 570 27 on on IN cord-276598-tm0yj2sn 570 28 silica silica NN cord-276598-tm0yj2sn 570 29 ) ) -RRB- cord-276598-tm0yj2sn 570 30 . . . cord-276598-tm0yj2sn 571 1 Triethyl Triethyl NNP cord-276598-tm0yj2sn 571 2 or or CC cord-276598-tm0yj2sn 571 3 trimethyl trimethyl NNP cord-276598-tm0yj2sn 571 4 phosphite phosphite NNP cord-276598-tm0yj2sn 571 5 were be VBD cord-276598-tm0yj2sn 571 6 used use VBN cord-276598-tm0yj2sn 571 7 as as IN cord-276598-tm0yj2sn 571 8 the the DT cord-276598-tm0yj2sn 571 9 P p NN cord-276598-tm0yj2sn 571 10 - - HYPH cord-276598-tm0yj2sn 571 11 source source NN cord-276598-tm0yj2sn 571 12 along along IN cord-276598-tm0yj2sn 571 13 with with IN cord-276598-tm0yj2sn 571 14 organic organic JJ cord-276598-tm0yj2sn 571 15 azide azide NN cord-276598-tm0yj2sn 571 16 derivatives derivative NNS cord-276598-tm0yj2sn 571 17 such such JJ cord-276598-tm0yj2sn 571 18 as as IN cord-276598-tm0yj2sn 571 19 ( ( -LRB- cord-276598-tm0yj2sn 571 20 azidomethyl)benzene azidomethyl)benzene NNP cord-276598-tm0yj2sn 571 21 , , , cord-276598-tm0yj2sn 571 22 azidocyclohexane azidocyclohexane NNP cord-276598-tm0yj2sn 571 23 , , , cord-276598-tm0yj2sn 571 24 ( ( -LRB- cord-276598-tm0yj2sn 571 25 2-azidopropan-2-yl)benzene 2-azidopropan-2-yl)benzene CD cord-276598-tm0yj2sn 571 26 , , , cord-276598-tm0yj2sn 571 27 azidobenzene azidobenzene NN cord-276598-tm0yj2sn 571 28 , , , cord-276598-tm0yj2sn 571 29 ethyl ethyl NNP cord-276598-tm0yj2sn 571 30 2-azidoacetate 2-azidoacetate CD cord-276598-tm0yj2sn 571 31 , , , cord-276598-tm0yj2sn 571 32 1-azidodecane 1-azidodecane CD cord-276598-tm0yj2sn 571 33 , , , cord-276598-tm0yj2sn 571 34 ( ( -LRB- cord-276598-tm0yj2sn 571 35 azidomethylene)dibenzene azidomethylene)dibenzene NNP cord-276598-tm0yj2sn 571 36 , , , cord-276598-tm0yj2sn 571 37 and and CC cord-276598-tm0yj2sn 571 38 ( ( -LRB- cord-276598-tm0yj2sn 571 39 3-azidoprop-1-en-1-yl)benzene 3-azidoprop-1-en-1-yl)benzene CD cord-276598-tm0yj2sn 571 40 . . . cord-276598-tm0yj2sn 571 41 _SP cord-276598-tm0yj2sn 572 1 Zimin Zimin NNP cord-276598-tm0yj2sn 572 2 et et NNP cord-276598-tm0yj2sn 572 3 al al NNP cord-276598-tm0yj2sn 572 4 . . NNP cord-276598-tm0yj2sn 572 5 reported report VBD cord-276598-tm0yj2sn 572 6 the the DT cord-276598-tm0yj2sn 572 7 1,2-hydrophosphinylation 1,2-hydrophosphinylation CD cord-276598-tm0yj2sn 572 8 of of IN cord-276598-tm0yj2sn 572 9 alkyl alkyl NN cord-276598-tm0yj2sn 572 10 nitriles nitrile NNS cord-276598-tm0yj2sn 572 11 ( ( -LRB- cord-276598-tm0yj2sn 572 12 R'-CN R'-CN NNS cord-276598-tm0yj2sn 572 13 , , , cord-276598-tm0yj2sn 572 14 R r NN cord-276598-tm0yj2sn 572 15 ' ' '' cord-276598-tm0yj2sn 573 1 = = NFP cord-276598-tm0yj2sn 573 2 alkyl alkyl NN cord-276598-tm0yj2sn 573 3 , , , cord-276598-tm0yj2sn 573 4 Ph Ph NNP cord-276598-tm0yj2sn 573 5 , , , cord-276598-tm0yj2sn 573 6 Bn Bn NNP cord-276598-tm0yj2sn 573 7 ) ) -RRB- cord-276598-tm0yj2sn 573 8 using use VBG cord-276598-tm0yj2sn 573 9 sodium sodium NN cord-276598-tm0yj2sn 573 10 dialkyl dialkyl NNP cord-276598-tm0yj2sn 573 11 phosphite phosphite NNP cord-276598-tm0yj2sn 573 12 ( ( -LRB- cord-276598-tm0yj2sn 573 13 ( ( -LRB- cord-276598-tm0yj2sn 573 14 RO)2PONa RO)2PONa NNP cord-276598-tm0yj2sn 573 15 , , , cord-276598-tm0yj2sn 573 16 R r NN cord-276598-tm0yj2sn 573 17 = = FW cord-276598-tm0yj2sn 573 18 Et et NN cord-276598-tm0yj2sn 573 19 , , , cord-276598-tm0yj2sn 573 20 Pr Pr NNP cord-276598-tm0yj2sn 573 21 ) ) -RRB- cord-276598-tm0yj2sn 573 22 to to TO cord-276598-tm0yj2sn 573 23 achieve achieve VB cord-276598-tm0yj2sn 573 24 the the DT cord-276598-tm0yj2sn 573 25 formation formation NN cord-276598-tm0yj2sn 573 26 of of IN cord-276598-tm0yj2sn 573 27 a a DT cord-276598-tm0yj2sn 573 28 P P NNP cord-276598-tm0yj2sn 573 29 - - HYPH cord-276598-tm0yj2sn 573 30 N n NN cord-276598-tm0yj2sn 573 31 featuring feature VBG cord-276598-tm0yj2sn 573 32 a a DT cord-276598-tm0yj2sn 573 33 P P NNP cord-276598-tm0yj2sn 573 34 - - HYPH cord-276598-tm0yj2sn 573 35 C C NNP cord-276598-tm0yj2sn 573 36 - - HYPH cord-276598-tm0yj2sn 573 37 N N NNP cord-276598-tm0yj2sn 573 38 - - HYPH cord-276598-tm0yj2sn 573 39 P p NN cord-276598-tm0yj2sn 573 40 linkage linkage NN cord-276598-tm0yj2sn 573 41 in in IN cord-276598-tm0yj2sn 573 42 which which WDT cord-276598-tm0yj2sn 573 43 the the DT cord-276598-tm0yj2sn 573 44 dialkyl dialkyl NNP cord-276598-tm0yj2sn 573 45 phosphite phosphite NNP cord-276598-tm0yj2sn 573 46 group group NNP cord-276598-tm0yj2sn 573 47 of of IN cord-276598-tm0yj2sn 573 48 ( ( -LRB- cord-276598-tm0yj2sn 573 49 RO)2PONa RO)2PONa NNP cord-276598-tm0yj2sn 573 50 was be VBD cord-276598-tm0yj2sn 573 51 added add VBN cord-276598-tm0yj2sn 573 52 to to IN cord-276598-tm0yj2sn 573 53 the the DT cord-276598-tm0yj2sn 573 54 carbon carbon NN cord-276598-tm0yj2sn 573 55 and and CC cord-276598-tm0yj2sn 573 56 nitrogen nitrogen NN cord-276598-tm0yj2sn 573 57 atoms atom NNS cord-276598-tm0yj2sn 573 58 of of IN cord-276598-tm0yj2sn 573 59 the the DT cord-276598-tm0yj2sn 573 60 nitriles nitrile NNS cord-276598-tm0yj2sn 573 61 ( ( -LRB- cord-276598-tm0yj2sn 573 62 Scheme scheme NN cord-276598-tm0yj2sn 573 63 16 16 CD cord-276598-tm0yj2sn 573 64 ) ) -RRB- cord-276598-tm0yj2sn 573 65 [ [ -LRB- cord-276598-tm0yj2sn 573 66 120 120 CD cord-276598-tm0yj2sn 573 67 ] ] -RRB- cord-276598-tm0yj2sn 573 68 . . . cord-276598-tm0yj2sn 573 69 _SP cord-276598-tm0yj2sn 574 1 Zimin Zimin NNP cord-276598-tm0yj2sn 574 2 et et NNP cord-276598-tm0yj2sn 574 3 al al NNP cord-276598-tm0yj2sn 574 4 . . NNP cord-276598-tm0yj2sn 574 5 reported report VBD cord-276598-tm0yj2sn 574 6 the the DT cord-276598-tm0yj2sn 574 7 1,2-hydrophosphinylation 1,2-hydrophosphinylation CD cord-276598-tm0yj2sn 574 8 of of IN cord-276598-tm0yj2sn 574 9 alkyl alkyl NN cord-276598-tm0yj2sn 574 10 nitriles nitrile NNS cord-276598-tm0yj2sn 574 11 ( ( -LRB- cord-276598-tm0yj2sn 574 12 R'-CN R'-CN NNS cord-276598-tm0yj2sn 574 13 , , , cord-276598-tm0yj2sn 574 14 R r NN cord-276598-tm0yj2sn 574 15 ' ' '' cord-276598-tm0yj2sn 575 1 = = NFP cord-276598-tm0yj2sn 575 2 alkyl alkyl NN cord-276598-tm0yj2sn 575 3 , , , cord-276598-tm0yj2sn 575 4 Ph Ph NNP cord-276598-tm0yj2sn 575 5 , , , cord-276598-tm0yj2sn 575 6 Bn Bn NNP cord-276598-tm0yj2sn 575 7 ) ) -RRB- cord-276598-tm0yj2sn 575 8 using use VBG cord-276598-tm0yj2sn 575 9 sodium sodium NN cord-276598-tm0yj2sn 575 10 dialkyl dialkyl NNP cord-276598-tm0yj2sn 575 11 phosphite phosphite NNP cord-276598-tm0yj2sn 575 12 ( ( -LRB- cord-276598-tm0yj2sn 575 13 ( ( -LRB- cord-276598-tm0yj2sn 575 14 RO RO NNP cord-276598-tm0yj2sn 575 15 ) ) -RRB- cord-276598-tm0yj2sn 576 1 2 2 CD cord-276598-tm0yj2sn 576 2 PONa PONa NNS cord-276598-tm0yj2sn 576 3 , , , cord-276598-tm0yj2sn 576 4 R r NN cord-276598-tm0yj2sn 576 5 = = FW cord-276598-tm0yj2sn 576 6 Et et NN cord-276598-tm0yj2sn 576 7 , , , cord-276598-tm0yj2sn 576 8 Pr Pr NNP cord-276598-tm0yj2sn 576 9 ) ) -RRB- cord-276598-tm0yj2sn 577 1 to to TO cord-276598-tm0yj2sn 577 2 achieve achieve VB cord-276598-tm0yj2sn 577 3 the the DT cord-276598-tm0yj2sn 577 4 formation formation NN cord-276598-tm0yj2sn 577 5 of of IN cord-276598-tm0yj2sn 577 6 a a DT cord-276598-tm0yj2sn 577 7 P P NNP cord-276598-tm0yj2sn 577 8 - - HYPH cord-276598-tm0yj2sn 577 9 N n NN cord-276598-tm0yj2sn 577 10 featuring feature VBG cord-276598-tm0yj2sn 577 11 a a DT cord-276598-tm0yj2sn 577 12 P P NNP cord-276598-tm0yj2sn 577 13 - - HYPH cord-276598-tm0yj2sn 577 14 C C NNP cord-276598-tm0yj2sn 577 15 - - HYPH cord-276598-tm0yj2sn 577 16 N N NNP cord-276598-tm0yj2sn 577 17 - - HYPH cord-276598-tm0yj2sn 577 18 P p NN cord-276598-tm0yj2sn 577 19 linkage linkage NN cord-276598-tm0yj2sn 577 20 in in IN cord-276598-tm0yj2sn 577 21 which which WDT cord-276598-tm0yj2sn 577 22 the the DT cord-276598-tm0yj2sn 577 23 dialkyl dialkyl NNP cord-276598-tm0yj2sn 577 24 phosphite phosphite NNP cord-276598-tm0yj2sn 577 25 group group NNP cord-276598-tm0yj2sn 577 26 of of IN cord-276598-tm0yj2sn 577 27 ( ( -LRB- cord-276598-tm0yj2sn 577 28 RO RO NNP cord-276598-tm0yj2sn 577 29 ) ) -RRB- cord-276598-tm0yj2sn 577 30 2 2 CD cord-276598-tm0yj2sn 577 31 PONa PONa NNS cord-276598-tm0yj2sn 577 32 was be VBD cord-276598-tm0yj2sn 577 33 added add VBN cord-276598-tm0yj2sn 577 34 to to IN cord-276598-tm0yj2sn 577 35 the the DT cord-276598-tm0yj2sn 577 36 carbon carbon NN cord-276598-tm0yj2sn 577 37 and and CC cord-276598-tm0yj2sn 577 38 nitrogen nitrogen NN cord-276598-tm0yj2sn 577 39 atoms atom NNS cord-276598-tm0yj2sn 577 40 of of IN cord-276598-tm0yj2sn 577 41 the the DT cord-276598-tm0yj2sn 577 42 nitriles nitrile NNS cord-276598-tm0yj2sn 577 43 ( ( -LRB- cord-276598-tm0yj2sn 577 44 Scheme scheme NN cord-276598-tm0yj2sn 577 45 16 16 CD cord-276598-tm0yj2sn 577 46 ) ) -RRB- cord-276598-tm0yj2sn 577 47 [ [ -LRB- cord-276598-tm0yj2sn 577 48 120 120 CD cord-276598-tm0yj2sn 577 49 ] ] -RRB- cord-276598-tm0yj2sn 577 50 . . . cord-276598-tm0yj2sn 578 1 Zimin Zimin NNP cord-276598-tm0yj2sn 578 2 et et NNP cord-276598-tm0yj2sn 578 3 al al NNP cord-276598-tm0yj2sn 578 4 . . NNP cord-276598-tm0yj2sn 578 5 reported report VBD cord-276598-tm0yj2sn 578 6 the the DT cord-276598-tm0yj2sn 578 7 1,2-hydrophosphinylation 1,2-hydrophosphinylation CD cord-276598-tm0yj2sn 578 8 of of IN cord-276598-tm0yj2sn 578 9 alkyl alkyl NN cord-276598-tm0yj2sn 578 10 nitriles nitrile NNS cord-276598-tm0yj2sn 578 11 ( ( -LRB- cord-276598-tm0yj2sn 578 12 R'-CN R'-CN NNS cord-276598-tm0yj2sn 578 13 , , , cord-276598-tm0yj2sn 578 14 R r NN cord-276598-tm0yj2sn 578 15 ' ' '' cord-276598-tm0yj2sn 579 1 = = NFP cord-276598-tm0yj2sn 579 2 alkyl alkyl NN cord-276598-tm0yj2sn 579 3 , , , cord-276598-tm0yj2sn 579 4 Ph Ph NNP cord-276598-tm0yj2sn 579 5 , , , cord-276598-tm0yj2sn 579 6 Bn Bn NNP cord-276598-tm0yj2sn 579 7 ) ) -RRB- cord-276598-tm0yj2sn 579 8 using use VBG cord-276598-tm0yj2sn 579 9 sodium sodium NN cord-276598-tm0yj2sn 579 10 dialkyl dialkyl NNP cord-276598-tm0yj2sn 579 11 phosphite phosphite NNP cord-276598-tm0yj2sn 579 12 ( ( -LRB- cord-276598-tm0yj2sn 579 13 ( ( -LRB- cord-276598-tm0yj2sn 579 14 RO)2PONa RO)2PONa NNP cord-276598-tm0yj2sn 579 15 , , , cord-276598-tm0yj2sn 579 16 R r NN cord-276598-tm0yj2sn 579 17 = = FW cord-276598-tm0yj2sn 579 18 Et et NN cord-276598-tm0yj2sn 579 19 , , , cord-276598-tm0yj2sn 579 20 Pr Pr NNP cord-276598-tm0yj2sn 579 21 ) ) -RRB- cord-276598-tm0yj2sn 579 22 to to TO cord-276598-tm0yj2sn 579 23 achieve achieve VB cord-276598-tm0yj2sn 579 24 the the DT cord-276598-tm0yj2sn 579 25 formation formation NN cord-276598-tm0yj2sn 579 26 of of IN cord-276598-tm0yj2sn 579 27 a a DT cord-276598-tm0yj2sn 579 28 P P NNP cord-276598-tm0yj2sn 579 29 - - HYPH cord-276598-tm0yj2sn 579 30 N n NN cord-276598-tm0yj2sn 579 31 featuring feature VBG cord-276598-tm0yj2sn 579 32 a a DT cord-276598-tm0yj2sn 579 33 P P NNP cord-276598-tm0yj2sn 579 34 - - HYPH cord-276598-tm0yj2sn 579 35 C C NNP cord-276598-tm0yj2sn 579 36 - - HYPH cord-276598-tm0yj2sn 579 37 N N NNP cord-276598-tm0yj2sn 579 38 - - HYPH cord-276598-tm0yj2sn 579 39 P p NN cord-276598-tm0yj2sn 579 40 linkage linkage NN cord-276598-tm0yj2sn 579 41 in in IN cord-276598-tm0yj2sn 579 42 which which WDT cord-276598-tm0yj2sn 579 43 the the DT cord-276598-tm0yj2sn 579 44 dialkyl dialkyl NNP cord-276598-tm0yj2sn 579 45 phosphite phosphite NNP cord-276598-tm0yj2sn 579 46 group group NNP cord-276598-tm0yj2sn 579 47 of of IN cord-276598-tm0yj2sn 579 48 ( ( -LRB- cord-276598-tm0yj2sn 579 49 RO)2PONa RO)2PONa NNP cord-276598-tm0yj2sn 579 50 was be VBD cord-276598-tm0yj2sn 579 51 added add VBN cord-276598-tm0yj2sn 579 52 to to IN cord-276598-tm0yj2sn 579 53 the the DT cord-276598-tm0yj2sn 579 54 carbon carbon NN cord-276598-tm0yj2sn 579 55 and and CC cord-276598-tm0yj2sn 579 56 nitrogen nitrogen NN cord-276598-tm0yj2sn 579 57 atoms atom NNS cord-276598-tm0yj2sn 579 58 of of IN cord-276598-tm0yj2sn 579 59 the the DT cord-276598-tm0yj2sn 579 60 nitriles nitrile NNS cord-276598-tm0yj2sn 579 61 ( ( -LRB- cord-276598-tm0yj2sn 579 62 Scheme scheme NN cord-276598-tm0yj2sn 579 63 16 16 CD cord-276598-tm0yj2sn 579 64 ) ) -RRB- cord-276598-tm0yj2sn 579 65 [ [ -LRB- cord-276598-tm0yj2sn 579 66 120 120 CD cord-276598-tm0yj2sn 579 67 ] ] -RRB- cord-276598-tm0yj2sn 579 68 . . . cord-276598-tm0yj2sn 580 1 Scheme scheme NN cord-276598-tm0yj2sn 580 2 16 16 CD cord-276598-tm0yj2sn 580 3 . . . cord-276598-tm0yj2sn 581 1 A a DT cord-276598-tm0yj2sn 581 2 1,2-hydrophosphinylation 1,2-hydrophosphinylation CD cord-276598-tm0yj2sn 581 3 of of IN cord-276598-tm0yj2sn 581 4 nitriles nitrile NNS cord-276598-tm0yj2sn 581 5 to to TO cord-276598-tm0yj2sn 581 6 form form VB cord-276598-tm0yj2sn 581 7 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 581 8 . . . cord-276598-tm0yj2sn 582 1 Chabour Chabour NNP cord-276598-tm0yj2sn 582 2 et et FW cord-276598-tm0yj2sn 582 3 al al NNP cord-276598-tm0yj2sn 582 4 . . NNP cord-276598-tm0yj2sn 582 5 reported report VBD cord-276598-tm0yj2sn 582 6 a a DT cord-276598-tm0yj2sn 582 7 diastereoselective diastereoselective NN cord-276598-tm0yj2sn 582 8 P P NNP cord-276598-tm0yj2sn 582 9 - - HYPH cord-276598-tm0yj2sn 582 10 N n CD cord-276598-tm0yj2sn 582 11 synthesis synthesis NN cord-276598-tm0yj2sn 582 12 via via IN cord-276598-tm0yj2sn 582 13 the the DT cord-276598-tm0yj2sn 582 14 PAD pad NN cord-276598-tm0yj2sn 582 15 process process NN cord-276598-tm0yj2sn 582 16 using use VBG cord-276598-tm0yj2sn 582 17 a a DT cord-276598-tm0yj2sn 582 18 TsOH TsOH NNP cord-276598-tm0yj2sn 582 19 acid acid NN cord-276598-tm0yj2sn 582 20 catalyst catalyst NN cord-276598-tm0yj2sn 582 21 and and CC cord-276598-tm0yj2sn 582 22 a a DT cord-276598-tm0yj2sn 582 23 dienophile dienophile NN cord-276598-tm0yj2sn 582 24 , , , cord-276598-tm0yj2sn 582 25 maleimide maleimide NNP cord-276598-tm0yj2sn 582 26 ( ( -LRB- cord-276598-tm0yj2sn 582 27 Scheme scheme NN cord-276598-tm0yj2sn 582 28 17 17 CD cord-276598-tm0yj2sn 582 29 ) ) -RRB- cord-276598-tm0yj2sn 582 30 [ [ -LRB- cord-276598-tm0yj2sn 582 31 1 1 CD cord-276598-tm0yj2sn 582 32 ] ] -RRB- cord-276598-tm0yj2sn 582 33 . . . cord-276598-tm0yj2sn 583 1 Flash flash NN cord-276598-tm0yj2sn 583 2 chromatography chromatography NN cord-276598-tm0yj2sn 583 3 was be VBD cord-276598-tm0yj2sn 583 4 used use VBN cord-276598-tm0yj2sn 583 5 to to TO cord-276598-tm0yj2sn 583 6 isolate isolate VB cord-276598-tm0yj2sn 583 7 the the DT cord-276598-tm0yj2sn 583 8 desired desire VBN cord-276598-tm0yj2sn 583 9 product product NN cord-276598-tm0yj2sn 583 10 in in IN cord-276598-tm0yj2sn 583 11 40 40 CD cord-276598-tm0yj2sn 583 12 - - SYM cord-276598-tm0yj2sn 583 13 88 88 CD cord-276598-tm0yj2sn 583 14 % % NN cord-276598-tm0yj2sn 583 15 yield yield NN cord-276598-tm0yj2sn 583 16 . . . cord-276598-tm0yj2sn 584 1 The the DT cord-276598-tm0yj2sn 584 2 scope scope NN cord-276598-tm0yj2sn 584 3 of of IN cord-276598-tm0yj2sn 584 4 the the DT cord-276598-tm0yj2sn 584 5 synthesis synthesis NN cord-276598-tm0yj2sn 584 6 was be VBD cord-276598-tm0yj2sn 584 7 explored explore VBN cord-276598-tm0yj2sn 584 8 with with IN cord-276598-tm0yj2sn 584 9 maleimide maleimide NNP cord-276598-tm0yj2sn 584 10 derivatives derivative NNS cord-276598-tm0yj2sn 584 11 with with IN cord-276598-tm0yj2sn 584 12 substituents substituent NNS cord-276598-tm0yj2sn 584 13 such such JJ cord-276598-tm0yj2sn 584 14 as as IN cord-276598-tm0yj2sn 584 15 4-FC6H4CH2 4-fc6h4ch2 CD cord-276598-tm0yj2sn 584 16 , , , cord-276598-tm0yj2sn 584 17 C6H4CH2 c6h4ch2 CD cord-276598-tm0yj2sn 584 18 , , , cord-276598-tm0yj2sn 584 19 C6H4COCH3 C6H4COCH3 NNP cord-276598-tm0yj2sn 584 20 , , , cord-276598-tm0yj2sn 584 21 4-BrC6H4 4-brc6h4 CD cord-276598-tm0yj2sn 584 22 , , , cord-276598-tm0yj2sn 584 23 phenyl phenyl CD cord-276598-tm0yj2sn 584 24 , , , cord-276598-tm0yj2sn 584 25 and and CC cord-276598-tm0yj2sn 584 26 methyl methyl NN cord-276598-tm0yj2sn 584 27 . . . cord-276598-tm0yj2sn 585 1 The the DT cord-276598-tm0yj2sn 585 2 unsaturated unsaturated JJ cord-276598-tm0yj2sn 585 3 aldehyde aldehyde NN cord-276598-tm0yj2sn 585 4 derivatives derivative NNS cord-276598-tm0yj2sn 585 5 that that WDT cord-276598-tm0yj2sn 585 6 were be VBD cord-276598-tm0yj2sn 585 7 used use VBN cord-276598-tm0yj2sn 585 8 were be VBD cord-276598-tm0yj2sn 585 9 3,7-dimethylocta-2,6-dienal 3,7-dimethylocta-2,6-dienal JJ cord-276598-tm0yj2sn 585 10 , , , cord-276598-tm0yj2sn 585 11 3-methylbut-2-enal 3-methylbut-2-enal CD cord-276598-tm0yj2sn 585 12 , , , cord-276598-tm0yj2sn 585 13 pent-2-enal pent-2-enal NNP cord-276598-tm0yj2sn 585 14 , , , cord-276598-tm0yj2sn 585 15 and and CC cord-276598-tm0yj2sn 585 16 hex-2-enal hex-2-enal JJ cord-276598-tm0yj2sn 585 17 . . . cord-276598-tm0yj2sn 586 1 This this DT cord-276598-tm0yj2sn 586 2 newest new JJS cord-276598-tm0yj2sn 586 3 route route NN cord-276598-tm0yj2sn 586 4 for for IN cord-276598-tm0yj2sn 586 5 P p NN cord-276598-tm0yj2sn 586 6 - - HYPH cord-276598-tm0yj2sn 586 7 N n CD cord-276598-tm0yj2sn 586 8 synthesis synthesis NN cord-276598-tm0yj2sn 586 9 uses use VBZ cord-276598-tm0yj2sn 586 10 inexpensive inexpensive JJ cord-276598-tm0yj2sn 586 11 catalysts catalyst NNS cord-276598-tm0yj2sn 586 12 , , , cord-276598-tm0yj2sn 586 13 generates generate VBZ cord-276598-tm0yj2sn 586 14 only only RB cord-276598-tm0yj2sn 586 15 H2O h2o NN cord-276598-tm0yj2sn 586 16 as as IN cord-276598-tm0yj2sn 586 17 a a DT cord-276598-tm0yj2sn 586 18 by by IN cord-276598-tm0yj2sn 586 19 - - HYPH cord-276598-tm0yj2sn 586 20 product product NN cord-276598-tm0yj2sn 586 21 in in IN cord-276598-tm0yj2sn 586 22 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 586 23 amounts amount NNS cord-276598-tm0yj2sn 586 24 , , , cord-276598-tm0yj2sn 586 25 and and CC cord-276598-tm0yj2sn 586 26 demonstrates demonstrate VBZ cord-276598-tm0yj2sn 586 27 an an DT cord-276598-tm0yj2sn 586 28 important important JJ cord-276598-tm0yj2sn 586 29 route route NN cord-276598-tm0yj2sn 586 30 to to IN cord-276598-tm0yj2sn 586 31 the the DT cord-276598-tm0yj2sn 586 32 synthesis synthesis NN cord-276598-tm0yj2sn 586 33 of of IN cord-276598-tm0yj2sn 586 34 polyfunctionalized polyfunctionalized NNP cord-276598-tm0yj2sn 586 35 P P NNP cord-276598-tm0yj2sn 586 36 - - HYPH cord-276598-tm0yj2sn 586 37 N N NNP cord-276598-tm0yj2sn 586 38 compounds compound NNS cord-276598-tm0yj2sn 586 39 . . . cord-276598-tm0yj2sn 586 40 _SP cord-276598-tm0yj2sn 587 1 Chabour Chabour NNP cord-276598-tm0yj2sn 587 2 et et FW cord-276598-tm0yj2sn 587 3 al al NNP cord-276598-tm0yj2sn 587 4 . . NNP cord-276598-tm0yj2sn 587 5 reported report VBD cord-276598-tm0yj2sn 587 6 a a DT cord-276598-tm0yj2sn 587 7 diastereoselective diastereoselective NN cord-276598-tm0yj2sn 587 8 P P NNP cord-276598-tm0yj2sn 587 9 - - HYPH cord-276598-tm0yj2sn 587 10 N n CD cord-276598-tm0yj2sn 587 11 synthesis synthesis NN cord-276598-tm0yj2sn 587 12 via via IN cord-276598-tm0yj2sn 587 13 the the DT cord-276598-tm0yj2sn 587 14 PAD pad NN cord-276598-tm0yj2sn 587 15 process process NN cord-276598-tm0yj2sn 587 16 using use VBG cord-276598-tm0yj2sn 587 17 a a DT cord-276598-tm0yj2sn 587 18 TsOH TsOH NNP cord-276598-tm0yj2sn 587 19 acid acid NN cord-276598-tm0yj2sn 587 20 catalyst catalyst NN cord-276598-tm0yj2sn 587 21 and and CC cord-276598-tm0yj2sn 587 22 a a DT cord-276598-tm0yj2sn 587 23 dienophile dienophile NN cord-276598-tm0yj2sn 587 24 , , , cord-276598-tm0yj2sn 587 25 maleimide maleimide NNP cord-276598-tm0yj2sn 587 26 ( ( -LRB- cord-276598-tm0yj2sn 587 27 Scheme scheme NN cord-276598-tm0yj2sn 587 28 17 17 CD cord-276598-tm0yj2sn 587 29 ) ) -RRB- cord-276598-tm0yj2sn 587 30 [ [ -LRB- cord-276598-tm0yj2sn 587 31 1 1 CD cord-276598-tm0yj2sn 587 32 ] ] -RRB- cord-276598-tm0yj2sn 587 33 . . . cord-276598-tm0yj2sn 588 1 Flash flash NN cord-276598-tm0yj2sn 588 2 chromatography chromatography NN cord-276598-tm0yj2sn 588 3 was be VBD cord-276598-tm0yj2sn 588 4 used use VBN cord-276598-tm0yj2sn 588 5 to to TO cord-276598-tm0yj2sn 588 6 isolate isolate VB cord-276598-tm0yj2sn 588 7 the the DT cord-276598-tm0yj2sn 588 8 desired desire VBN cord-276598-tm0yj2sn 588 9 product product NN cord-276598-tm0yj2sn 588 10 in in IN cord-276598-tm0yj2sn 588 11 40 40 CD cord-276598-tm0yj2sn 588 12 - - SYM cord-276598-tm0yj2sn 588 13 88 88 CD cord-276598-tm0yj2sn 588 14 % % NN cord-276598-tm0yj2sn 588 15 yield yield NN cord-276598-tm0yj2sn 588 16 . . . cord-276598-tm0yj2sn 589 1 The the DT cord-276598-tm0yj2sn 589 2 scope scope NN cord-276598-tm0yj2sn 589 3 of of IN cord-276598-tm0yj2sn 589 4 the the DT cord-276598-tm0yj2sn 589 5 synthesis synthesis NN cord-276598-tm0yj2sn 589 6 was be VBD cord-276598-tm0yj2sn 589 7 explored explore VBN cord-276598-tm0yj2sn 589 8 with with IN cord-276598-tm0yj2sn 589 9 maleimide maleimide NNP cord-276598-tm0yj2sn 589 10 derivatives derivative NNS cord-276598-tm0yj2sn 589 11 with with IN cord-276598-tm0yj2sn 589 12 substituents substituent NNS cord-276598-tm0yj2sn 589 13 such such JJ cord-276598-tm0yj2sn 589 14 as as IN cord-276598-tm0yj2sn 589 15 4-FC 4-fc CD cord-276598-tm0yj2sn 589 16 6 6 CD cord-276598-tm0yj2sn 589 17 H h NN cord-276598-tm0yj2sn 589 18 4 4 CD cord-276598-tm0yj2sn 589 19 CH CH NNP cord-276598-tm0yj2sn 589 20 2 2 CD cord-276598-tm0yj2sn 589 21 , , , cord-276598-tm0yj2sn 589 22 C C NNP cord-276598-tm0yj2sn 589 23 6 6 CD cord-276598-tm0yj2sn 589 24 H h NN cord-276598-tm0yj2sn 589 25 4 4 CD cord-276598-tm0yj2sn 589 26 CH CH NNP cord-276598-tm0yj2sn 589 27 2 2 CD cord-276598-tm0yj2sn 589 28 , , , cord-276598-tm0yj2sn 589 29 C C NNP cord-276598-tm0yj2sn 589 30 6 6 CD cord-276598-tm0yj2sn 589 31 H h NN cord-276598-tm0yj2sn 589 32 4 4 CD cord-276598-tm0yj2sn 589 33 COCH COCH NNP cord-276598-tm0yj2sn 589 34 3 3 CD cord-276598-tm0yj2sn 589 35 , , , cord-276598-tm0yj2sn 589 36 4-BrC 4-brc CD cord-276598-tm0yj2sn 589 37 6 6 CD cord-276598-tm0yj2sn 589 38 H h NN cord-276598-tm0yj2sn 589 39 4 4 CD cord-276598-tm0yj2sn 589 40 , , , cord-276598-tm0yj2sn 589 41 phenyl phenyl NN cord-276598-tm0yj2sn 589 42 , , , cord-276598-tm0yj2sn 589 43 and and CC cord-276598-tm0yj2sn 589 44 methyl methyl NN cord-276598-tm0yj2sn 589 45 . . . cord-276598-tm0yj2sn 590 1 The the DT cord-276598-tm0yj2sn 590 2 unsaturated unsaturated JJ cord-276598-tm0yj2sn 590 3 aldehyde aldehyde NN cord-276598-tm0yj2sn 590 4 derivatives derivative NNS cord-276598-tm0yj2sn 590 5 that that WDT cord-276598-tm0yj2sn 590 6 were be VBD cord-276598-tm0yj2sn 590 7 used use VBN cord-276598-tm0yj2sn 590 8 were be VBD cord-276598-tm0yj2sn 590 9 3,7-dimethylocta-2,6-dienal 3,7-dimethylocta-2,6-dienal JJ cord-276598-tm0yj2sn 590 10 , , , cord-276598-tm0yj2sn 590 11 3-methylbut-2-enal 3-methylbut-2-enal CD cord-276598-tm0yj2sn 590 12 , , , cord-276598-tm0yj2sn 590 13 pent-2-enal pent-2-enal NNP cord-276598-tm0yj2sn 590 14 , , , cord-276598-tm0yj2sn 590 15 and and CC cord-276598-tm0yj2sn 590 16 hex-2-enal hex-2-enal JJ cord-276598-tm0yj2sn 590 17 . . . cord-276598-tm0yj2sn 591 1 This this DT cord-276598-tm0yj2sn 591 2 newest new JJS cord-276598-tm0yj2sn 591 3 route route NN cord-276598-tm0yj2sn 591 4 for for IN cord-276598-tm0yj2sn 591 5 P p NN cord-276598-tm0yj2sn 591 6 - - HYPH cord-276598-tm0yj2sn 591 7 N n CD cord-276598-tm0yj2sn 591 8 synthesis synthesis NN cord-276598-tm0yj2sn 591 9 uses use VBZ cord-276598-tm0yj2sn 591 10 inexpensive inexpensive JJ cord-276598-tm0yj2sn 591 11 catalysts catalyst NNS cord-276598-tm0yj2sn 591 12 , , , cord-276598-tm0yj2sn 591 13 generates generate VBZ cord-276598-tm0yj2sn 591 14 only only RB cord-276598-tm0yj2sn 591 15 H h NN cord-276598-tm0yj2sn 591 16 2 2 CD cord-276598-tm0yj2sn 591 17 O o NN cord-276598-tm0yj2sn 591 18 as as IN cord-276598-tm0yj2sn 591 19 a a DT cord-276598-tm0yj2sn 591 20 by by IN cord-276598-tm0yj2sn 591 21 - - HYPH cord-276598-tm0yj2sn 591 22 product product NN cord-276598-tm0yj2sn 591 23 in in IN cord-276598-tm0yj2sn 591 24 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 591 25 amounts amount NNS cord-276598-tm0yj2sn 591 26 , , , cord-276598-tm0yj2sn 591 27 and and CC cord-276598-tm0yj2sn 591 28 demonstrates demonstrate VBZ cord-276598-tm0yj2sn 591 29 an an DT cord-276598-tm0yj2sn 591 30 important important JJ cord-276598-tm0yj2sn 591 31 route route NN cord-276598-tm0yj2sn 591 32 to to IN cord-276598-tm0yj2sn 591 33 the the DT cord-276598-tm0yj2sn 591 34 synthesis synthesis NN cord-276598-tm0yj2sn 591 35 of of IN cord-276598-tm0yj2sn 591 36 polyfunctionalized polyfunctionalized NNP cord-276598-tm0yj2sn 591 37 P P NNP cord-276598-tm0yj2sn 591 38 - - HYPH cord-276598-tm0yj2sn 591 39 N N NNP cord-276598-tm0yj2sn 591 40 compounds compound NNS cord-276598-tm0yj2sn 591 41 . . . cord-276598-tm0yj2sn 592 1 Zimin Zimin NNP cord-276598-tm0yj2sn 592 2 et et NNP cord-276598-tm0yj2sn 592 3 al al NNP cord-276598-tm0yj2sn 592 4 . . NNP cord-276598-tm0yj2sn 592 5 reported report VBD cord-276598-tm0yj2sn 592 6 the the DT cord-276598-tm0yj2sn 592 7 1,2-hydrophosphinylation 1,2-hydrophosphinylation CD cord-276598-tm0yj2sn 592 8 of of IN cord-276598-tm0yj2sn 592 9 alkyl alkyl NN cord-276598-tm0yj2sn 592 10 nitriles nitrile NNS cord-276598-tm0yj2sn 592 11 ( ( -LRB- cord-276598-tm0yj2sn 592 12 R'-CN R'-CN NNS cord-276598-tm0yj2sn 592 13 , , , cord-276598-tm0yj2sn 592 14 R r NN cord-276598-tm0yj2sn 592 15 ' ' '' cord-276598-tm0yj2sn 593 1 = = NFP cord-276598-tm0yj2sn 593 2 alkyl alkyl NN cord-276598-tm0yj2sn 593 3 , , , cord-276598-tm0yj2sn 593 4 Ph Ph NNP cord-276598-tm0yj2sn 593 5 , , , cord-276598-tm0yj2sn 593 6 Bn Bn NNP cord-276598-tm0yj2sn 593 7 ) ) -RRB- cord-276598-tm0yj2sn 593 8 using use VBG cord-276598-tm0yj2sn 593 9 sodium sodium NN cord-276598-tm0yj2sn 593 10 dialkyl dialkyl NNP cord-276598-tm0yj2sn 593 11 phosphite phosphite NNP cord-276598-tm0yj2sn 593 12 ( ( -LRB- cord-276598-tm0yj2sn 593 13 ( ( -LRB- cord-276598-tm0yj2sn 593 14 RO)2PONa RO)2PONa NNP cord-276598-tm0yj2sn 593 15 , , , cord-276598-tm0yj2sn 593 16 R r NN cord-276598-tm0yj2sn 593 17 = = FW cord-276598-tm0yj2sn 593 18 Et et NN cord-276598-tm0yj2sn 593 19 , , , cord-276598-tm0yj2sn 593 20 Pr Pr NNP cord-276598-tm0yj2sn 593 21 ) ) -RRB- cord-276598-tm0yj2sn 593 22 to to TO cord-276598-tm0yj2sn 593 23 achieve achieve VB cord-276598-tm0yj2sn 593 24 the the DT cord-276598-tm0yj2sn 593 25 formation formation NN cord-276598-tm0yj2sn 593 26 of of IN cord-276598-tm0yj2sn 593 27 a a DT cord-276598-tm0yj2sn 593 28 P P NNP cord-276598-tm0yj2sn 593 29 - - HYPH cord-276598-tm0yj2sn 593 30 N n NN cord-276598-tm0yj2sn 593 31 featuring feature VBG cord-276598-tm0yj2sn 593 32 a a DT cord-276598-tm0yj2sn 593 33 P P NNP cord-276598-tm0yj2sn 593 34 - - HYPH cord-276598-tm0yj2sn 593 35 C C NNP cord-276598-tm0yj2sn 593 36 - - HYPH cord-276598-tm0yj2sn 593 37 N N NNP cord-276598-tm0yj2sn 593 38 - - HYPH cord-276598-tm0yj2sn 593 39 P p NN cord-276598-tm0yj2sn 593 40 linkage linkage NN cord-276598-tm0yj2sn 593 41 in in IN cord-276598-tm0yj2sn 593 42 which which WDT cord-276598-tm0yj2sn 593 43 the the DT cord-276598-tm0yj2sn 593 44 dialkyl dialkyl NNP cord-276598-tm0yj2sn 593 45 phosphite phosphite NNP cord-276598-tm0yj2sn 593 46 group group NNP cord-276598-tm0yj2sn 593 47 of of IN cord-276598-tm0yj2sn 593 48 ( ( -LRB- cord-276598-tm0yj2sn 593 49 RO)2PONa RO)2PONa NNP cord-276598-tm0yj2sn 593 50 was be VBD cord-276598-tm0yj2sn 593 51 added add VBN cord-276598-tm0yj2sn 593 52 to to IN cord-276598-tm0yj2sn 593 53 the the DT cord-276598-tm0yj2sn 593 54 carbon carbon NN cord-276598-tm0yj2sn 593 55 and and CC cord-276598-tm0yj2sn 593 56 nitrogen nitrogen NN cord-276598-tm0yj2sn 593 57 atoms atom NNS cord-276598-tm0yj2sn 593 58 of of IN cord-276598-tm0yj2sn 593 59 the the DT cord-276598-tm0yj2sn 593 60 nitriles nitrile NNS cord-276598-tm0yj2sn 593 61 ( ( -LRB- cord-276598-tm0yj2sn 593 62 Scheme scheme NN cord-276598-tm0yj2sn 593 63 16 16 CD cord-276598-tm0yj2sn 593 64 ) ) -RRB- cord-276598-tm0yj2sn 593 65 [ [ -LRB- cord-276598-tm0yj2sn 593 66 120 120 CD cord-276598-tm0yj2sn 593 67 ] ] -RRB- cord-276598-tm0yj2sn 593 68 . . . cord-276598-tm0yj2sn 594 1 Scheme scheme NN cord-276598-tm0yj2sn 594 2 16 16 CD cord-276598-tm0yj2sn 594 3 . . . cord-276598-tm0yj2sn 595 1 A a DT cord-276598-tm0yj2sn 595 2 1,2-hydrophosphinylation 1,2-hydrophosphinylation CD cord-276598-tm0yj2sn 595 3 of of IN cord-276598-tm0yj2sn 595 4 nitriles nitrile NNS cord-276598-tm0yj2sn 595 5 to to TO cord-276598-tm0yj2sn 595 6 form form VB cord-276598-tm0yj2sn 595 7 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 595 8 . . . cord-276598-tm0yj2sn 596 1 Chabour Chabour NNP cord-276598-tm0yj2sn 596 2 et et FW cord-276598-tm0yj2sn 596 3 al al NNP cord-276598-tm0yj2sn 596 4 . . NNP cord-276598-tm0yj2sn 596 5 reported report VBD cord-276598-tm0yj2sn 596 6 a a DT cord-276598-tm0yj2sn 596 7 diastereoselective diastereoselective NN cord-276598-tm0yj2sn 596 8 P P NNP cord-276598-tm0yj2sn 596 9 - - HYPH cord-276598-tm0yj2sn 596 10 N n CD cord-276598-tm0yj2sn 596 11 synthesis synthesis NN cord-276598-tm0yj2sn 596 12 via via IN cord-276598-tm0yj2sn 596 13 the the DT cord-276598-tm0yj2sn 596 14 PAD pad NN cord-276598-tm0yj2sn 596 15 process process NN cord-276598-tm0yj2sn 596 16 using use VBG cord-276598-tm0yj2sn 596 17 a a DT cord-276598-tm0yj2sn 596 18 TsOH TsOH NNP cord-276598-tm0yj2sn 596 19 acid acid NN cord-276598-tm0yj2sn 596 20 catalyst catalyst NN cord-276598-tm0yj2sn 596 21 and and CC cord-276598-tm0yj2sn 596 22 a a DT cord-276598-tm0yj2sn 596 23 dienophile dienophile NN cord-276598-tm0yj2sn 596 24 , , , cord-276598-tm0yj2sn 596 25 maleimide maleimide NNP cord-276598-tm0yj2sn 596 26 ( ( -LRB- cord-276598-tm0yj2sn 596 27 Scheme scheme NN cord-276598-tm0yj2sn 596 28 17 17 CD cord-276598-tm0yj2sn 596 29 ) ) -RRB- cord-276598-tm0yj2sn 596 30 [ [ -LRB- cord-276598-tm0yj2sn 596 31 1 1 CD cord-276598-tm0yj2sn 596 32 ] ] -RRB- cord-276598-tm0yj2sn 596 33 . . . cord-276598-tm0yj2sn 597 1 Flash flash NN cord-276598-tm0yj2sn 597 2 chromatography chromatography NN cord-276598-tm0yj2sn 597 3 was be VBD cord-276598-tm0yj2sn 597 4 used use VBN cord-276598-tm0yj2sn 597 5 to to TO cord-276598-tm0yj2sn 597 6 isolate isolate VB cord-276598-tm0yj2sn 597 7 the the DT cord-276598-tm0yj2sn 597 8 desired desire VBN cord-276598-tm0yj2sn 597 9 product product NN cord-276598-tm0yj2sn 597 10 in in IN cord-276598-tm0yj2sn 597 11 40 40 CD cord-276598-tm0yj2sn 597 12 - - SYM cord-276598-tm0yj2sn 597 13 88 88 CD cord-276598-tm0yj2sn 597 14 % % NN cord-276598-tm0yj2sn 597 15 yield yield NN cord-276598-tm0yj2sn 597 16 . . . cord-276598-tm0yj2sn 598 1 The the DT cord-276598-tm0yj2sn 598 2 scope scope NN cord-276598-tm0yj2sn 598 3 of of IN cord-276598-tm0yj2sn 598 4 the the DT cord-276598-tm0yj2sn 598 5 synthesis synthesis NN cord-276598-tm0yj2sn 598 6 was be VBD cord-276598-tm0yj2sn 598 7 explored explore VBN cord-276598-tm0yj2sn 598 8 with with IN cord-276598-tm0yj2sn 598 9 maleimide maleimide NNP cord-276598-tm0yj2sn 598 10 derivatives derivative NNS cord-276598-tm0yj2sn 598 11 with with IN cord-276598-tm0yj2sn 598 12 substituents substituent NNS cord-276598-tm0yj2sn 598 13 such such JJ cord-276598-tm0yj2sn 598 14 as as IN cord-276598-tm0yj2sn 598 15 4-FC6H4CH2 4-fc6h4ch2 CD cord-276598-tm0yj2sn 598 16 , , , cord-276598-tm0yj2sn 598 17 C6H4CH2 c6h4ch2 CD cord-276598-tm0yj2sn 598 18 , , , cord-276598-tm0yj2sn 598 19 C6H4COCH3 C6H4COCH3 NNP cord-276598-tm0yj2sn 598 20 , , , cord-276598-tm0yj2sn 598 21 4-BrC6H4 4-brc6h4 CD cord-276598-tm0yj2sn 598 22 , , , cord-276598-tm0yj2sn 598 23 phenyl phenyl CD cord-276598-tm0yj2sn 598 24 , , , cord-276598-tm0yj2sn 598 25 and and CC cord-276598-tm0yj2sn 598 26 methyl methyl NN cord-276598-tm0yj2sn 598 27 . . . cord-276598-tm0yj2sn 599 1 The the DT cord-276598-tm0yj2sn 599 2 unsaturated unsaturated JJ cord-276598-tm0yj2sn 599 3 aldehyde aldehyde NN cord-276598-tm0yj2sn 599 4 derivatives derivative NNS cord-276598-tm0yj2sn 599 5 that that WDT cord-276598-tm0yj2sn 599 6 were be VBD cord-276598-tm0yj2sn 599 7 used use VBN cord-276598-tm0yj2sn 599 8 were be VBD cord-276598-tm0yj2sn 599 9 3,7-dimethylocta-2,6-dienal 3,7-dimethylocta-2,6-dienal JJ cord-276598-tm0yj2sn 599 10 , , , cord-276598-tm0yj2sn 599 11 3-methylbut-2-enal 3-methylbut-2-enal CD cord-276598-tm0yj2sn 599 12 , , , cord-276598-tm0yj2sn 599 13 pent-2-enal pent-2-enal NNP cord-276598-tm0yj2sn 599 14 , , , cord-276598-tm0yj2sn 599 15 and and CC cord-276598-tm0yj2sn 599 16 hex-2-enal hex-2-enal JJ cord-276598-tm0yj2sn 599 17 . . . cord-276598-tm0yj2sn 600 1 This this DT cord-276598-tm0yj2sn 600 2 newest new JJS cord-276598-tm0yj2sn 600 3 route route NN cord-276598-tm0yj2sn 600 4 for for IN cord-276598-tm0yj2sn 600 5 P p NN cord-276598-tm0yj2sn 600 6 - - HYPH cord-276598-tm0yj2sn 600 7 N n CD cord-276598-tm0yj2sn 600 8 synthesis synthesis NN cord-276598-tm0yj2sn 600 9 uses use VBZ cord-276598-tm0yj2sn 600 10 inexpensive inexpensive JJ cord-276598-tm0yj2sn 600 11 catalysts catalyst NNS cord-276598-tm0yj2sn 600 12 , , , cord-276598-tm0yj2sn 600 13 generates generate VBZ cord-276598-tm0yj2sn 600 14 only only RB cord-276598-tm0yj2sn 600 15 H2O h2o NN cord-276598-tm0yj2sn 600 16 as as IN cord-276598-tm0yj2sn 600 17 a a DT cord-276598-tm0yj2sn 600 18 by by IN cord-276598-tm0yj2sn 600 19 - - HYPH cord-276598-tm0yj2sn 600 20 product product NN cord-276598-tm0yj2sn 600 21 in in IN cord-276598-tm0yj2sn 600 22 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 600 23 amounts amount NNS cord-276598-tm0yj2sn 600 24 , , , cord-276598-tm0yj2sn 600 25 and and CC cord-276598-tm0yj2sn 600 26 demonstrates demonstrate VBZ cord-276598-tm0yj2sn 600 27 an an DT cord-276598-tm0yj2sn 600 28 important important JJ cord-276598-tm0yj2sn 600 29 route route NN cord-276598-tm0yj2sn 600 30 to to IN cord-276598-tm0yj2sn 600 31 the the DT cord-276598-tm0yj2sn 600 32 synthesis synthesis NN cord-276598-tm0yj2sn 600 33 of of IN cord-276598-tm0yj2sn 600 34 polyfunctionalized polyfunctionalized NNP cord-276598-tm0yj2sn 600 35 P P NNP cord-276598-tm0yj2sn 600 36 - - HYPH cord-276598-tm0yj2sn 600 37 N N NNP cord-276598-tm0yj2sn 600 38 compounds compound NNS cord-276598-tm0yj2sn 600 39 . . . cord-276598-tm0yj2sn 600 40 _SP cord-276598-tm0yj2sn 601 1 A a DT cord-276598-tm0yj2sn 601 2 wealth wealth NN cord-276598-tm0yj2sn 601 3 of of IN cord-276598-tm0yj2sn 601 4 information information NN cord-276598-tm0yj2sn 601 5 on on IN cord-276598-tm0yj2sn 601 6 the the DT cord-276598-tm0yj2sn 601 7 mechanisms mechanism NNS cord-276598-tm0yj2sn 601 8 for for IN cord-276598-tm0yj2sn 601 9 the the DT cord-276598-tm0yj2sn 601 10 synthetic synthetic JJ cord-276598-tm0yj2sn 601 11 routes route NNS cord-276598-tm0yj2sn 601 12 to to IN cord-276598-tm0yj2sn 601 13 P p NN cord-276598-tm0yj2sn 601 14 - - HYPH cord-276598-tm0yj2sn 601 15 Ns Ns NNP cord-276598-tm0yj2sn 601 16 is be VBZ cord-276598-tm0yj2sn 601 17 available available JJ cord-276598-tm0yj2sn 601 18 . . . cord-276598-tm0yj2sn 602 1 For for IN cord-276598-tm0yj2sn 602 2 each each DT cord-276598-tm0yj2sn 602 3 of of IN cord-276598-tm0yj2sn 602 4 the the DT cord-276598-tm0yj2sn 602 5 main main JJ cord-276598-tm0yj2sn 602 6 categories category NNS cord-276598-tm0yj2sn 602 7 highlighted highlight VBN cord-276598-tm0yj2sn 602 8 above above RB cord-276598-tm0yj2sn 602 9 , , , cord-276598-tm0yj2sn 602 10 researchers researcher NNS cord-276598-tm0yj2sn 602 11 have have VBP cord-276598-tm0yj2sn 602 12 provided provide VBN cord-276598-tm0yj2sn 602 13 mechanistic mechanistic JJ cord-276598-tm0yj2sn 602 14 insight insight NN cord-276598-tm0yj2sn 602 15 into into IN cord-276598-tm0yj2sn 602 16 the the DT cord-276598-tm0yj2sn 602 17 reaction reaction NN cord-276598-tm0yj2sn 602 18 by by IN cord-276598-tm0yj2sn 602 19 determining determine VBG cord-276598-tm0yj2sn 602 20 the the DT cord-276598-tm0yj2sn 602 21 main main JJ cord-276598-tm0yj2sn 602 22 sources source NNS cord-276598-tm0yj2sn 602 23 of of IN cord-276598-tm0yj2sn 602 24 oxidation oxidation NN cord-276598-tm0yj2sn 602 25 as as RB cord-276598-tm0yj2sn 602 26 well well RB cord-276598-tm0yj2sn 602 27 as as IN cord-276598-tm0yj2sn 602 28 electronic electronic JJ cord-276598-tm0yj2sn 602 29 and and CC cord-276598-tm0yj2sn 602 30 steric steric JJ cord-276598-tm0yj2sn 602 31 factors factor NNS cord-276598-tm0yj2sn 602 32 provided provide VBN cord-276598-tm0yj2sn 602 33 from from IN cord-276598-tm0yj2sn 602 34 the the DT cord-276598-tm0yj2sn 602 35 substituents substituent NNS cord-276598-tm0yj2sn 602 36 that that WDT cord-276598-tm0yj2sn 602 37 influence influence VBP cord-276598-tm0yj2sn 602 38 the the DT cord-276598-tm0yj2sn 602 39 reaction reaction NN cord-276598-tm0yj2sn 602 40 rate rate NN cord-276598-tm0yj2sn 602 41 . . . cord-276598-tm0yj2sn 603 1 Several several JJ cord-276598-tm0yj2sn 603 2 examples example NNS cord-276598-tm0yj2sn 603 3 of of IN cord-276598-tm0yj2sn 603 4 postulated postulate VBN cord-276598-tm0yj2sn 603 5 catalytic catalytic JJ cord-276598-tm0yj2sn 603 6 cycles cycle NNS cord-276598-tm0yj2sn 603 7 will will MD cord-276598-tm0yj2sn 603 8 be be VB cord-276598-tm0yj2sn 603 9 provided provide VBN cord-276598-tm0yj2sn 603 10 below below RB cord-276598-tm0yj2sn 603 11 , , , cord-276598-tm0yj2sn 603 12 illustrating illustrate VBG cord-276598-tm0yj2sn 603 13 the the DT cord-276598-tm0yj2sn 603 14 key key JJ cord-276598-tm0yj2sn 603 15 steps step NNS cord-276598-tm0yj2sn 603 16 , , , cord-276598-tm0yj2sn 603 17 similarities similarity NNS cord-276598-tm0yj2sn 603 18 , , , cord-276598-tm0yj2sn 603 19 and and CC cord-276598-tm0yj2sn 603 20 differences difference NNS cord-276598-tm0yj2sn 603 21 between between IN cord-276598-tm0yj2sn 603 22 them -PRON- PRP cord-276598-tm0yj2sn 603 23 . . . cord-276598-tm0yj2sn 604 1 Atherton Atherton NNP cord-276598-tm0yj2sn 604 2 , , , cord-276598-tm0yj2sn 604 3 Openshaw Openshaw NNP cord-276598-tm0yj2sn 604 4 and and CC cord-276598-tm0yj2sn 604 5 Todd Todd NNP cord-276598-tm0yj2sn 604 6 suggested suggest VBD cord-276598-tm0yj2sn 604 7 that that IN cord-276598-tm0yj2sn 604 8 the the DT cord-276598-tm0yj2sn 604 9 two two CD cord-276598-tm0yj2sn 604 10 - - HYPH cord-276598-tm0yj2sn 604 11 step step NN cord-276598-tm0yj2sn 604 12 mechanistic mechanistic JJ cord-276598-tm0yj2sn 604 13 process process NN cord-276598-tm0yj2sn 604 14 for for IN cord-276598-tm0yj2sn 604 15 the the DT cord-276598-tm0yj2sn 604 16 salt salt NN cord-276598-tm0yj2sn 604 17 elimination elimination NN cord-276598-tm0yj2sn 604 18 could could MD cord-276598-tm0yj2sn 604 19 involve involve VB cord-276598-tm0yj2sn 604 20 the the DT cord-276598-tm0yj2sn 604 21 formation formation NN cord-276598-tm0yj2sn 604 22 of of IN cord-276598-tm0yj2sn 604 23 dialkyl dialkyl NNP cord-276598-tm0yj2sn 604 24 or or CC cord-276598-tm0yj2sn 604 25 dibenzyl dibenzyl NNP cord-276598-tm0yj2sn 604 26 ( ( -LRB- cord-276598-tm0yj2sn 604 27 trichloromethyl)phosphonate trichloromethyl)phosphonate NNP cord-276598-tm0yj2sn 604 28 in in IN cord-276598-tm0yj2sn 604 29 the the DT cord-276598-tm0yj2sn 604 30 first first JJ cord-276598-tm0yj2sn 604 31 step step NN cord-276598-tm0yj2sn 604 32 , , , cord-276598-tm0yj2sn 604 33 from from IN cord-276598-tm0yj2sn 604 34 a a DT cord-276598-tm0yj2sn 604 35 reaction reaction NN cord-276598-tm0yj2sn 604 36 of of IN cord-276598-tm0yj2sn 604 37 ( ( -LRB- cord-276598-tm0yj2sn 604 38 RO ro NN cord-276598-tm0yj2sn 604 39 ) ) -RRB- cord-276598-tm0yj2sn 604 40 2 2 CD cord-276598-tm0yj2sn 604 41 P(O)H p(o)h NN cord-276598-tm0yj2sn 604 42 ( ( -LRB- cord-276598-tm0yj2sn 604 43 H H NNP cord-276598-tm0yj2sn 604 44 - - HYPH cord-276598-tm0yj2sn 604 45 P p NN cord-276598-tm0yj2sn 604 46 ; ; : cord-276598-tm0yj2sn 604 47 R r NN cord-276598-tm0yj2sn 604 48 = = NN cord-276598-tm0yj2sn 604 49 alkyl alkyl NN cord-276598-tm0yj2sn 604 50 ) ) -RRB- cord-276598-tm0yj2sn 604 51 and and CC cord-276598-tm0yj2sn 604 52 CCl CCl NNS cord-276598-tm0yj2sn 604 53 4 4 CD cord-276598-tm0yj2sn 604 54 in in IN cord-276598-tm0yj2sn 604 55 the the DT cord-276598-tm0yj2sn 604 56 presence presence NN cord-276598-tm0yj2sn 604 57 of of IN cord-276598-tm0yj2sn 604 58 Et Et NNP cord-276598-tm0yj2sn 604 59 3 3 CD cord-276598-tm0yj2sn 604 60 N N NNP cord-276598-tm0yj2sn 604 61 [ [ -LRB- cord-276598-tm0yj2sn 604 62 78 78 CD cord-276598-tm0yj2sn 604 63 ] ] -RRB- cord-276598-tm0yj2sn 604 64 . . . cord-276598-tm0yj2sn 605 1 The the DT cord-276598-tm0yj2sn 605 2 desired desire VBN cord-276598-tm0yj2sn 605 3 product product NN cord-276598-tm0yj2sn 605 4 is be VBZ cord-276598-tm0yj2sn 605 5 formed form VBN cord-276598-tm0yj2sn 605 6 in in IN cord-276598-tm0yj2sn 605 7 the the DT cord-276598-tm0yj2sn 605 8 second second JJ cord-276598-tm0yj2sn 605 9 step step NN cord-276598-tm0yj2sn 606 1 when when WRB cord-276598-tm0yj2sn 606 2 the the DT cord-276598-tm0yj2sn 606 3 ( ( -LRB- cord-276598-tm0yj2sn 606 4 trichloromethyl)phosphonate trichloromethyl)phosphonate NNP cord-276598-tm0yj2sn 606 5 reacts react NNS cord-276598-tm0yj2sn 606 6 with with IN cord-276598-tm0yj2sn 606 7 amine amine NN cord-276598-tm0yj2sn 606 8 , , , cord-276598-tm0yj2sn 606 9 forming form VBG cord-276598-tm0yj2sn 606 10 also also RB cord-276598-tm0yj2sn 606 11 CHCl CHCl VBZ cord-276598-tm0yj2sn 606 12 3 3 CD cord-276598-tm0yj2sn 606 13 in in IN cord-276598-tm0yj2sn 606 14 the the DT cord-276598-tm0yj2sn 606 15 process process NN cord-276598-tm0yj2sn 606 16 ( ( -LRB- cord-276598-tm0yj2sn 606 17 Scheme scheme NN cord-276598-tm0yj2sn 606 18 18 18 CD cord-276598-tm0yj2sn 606 19 ) ) -RRB- cord-276598-tm0yj2sn 606 20 . . . cord-276598-tm0yj2sn 607 1 Although although IN cord-276598-tm0yj2sn 607 2 this this DT cord-276598-tm0yj2sn 607 3 mechanism mechanism NN cord-276598-tm0yj2sn 607 4 is be VBZ cord-276598-tm0yj2sn 607 5 plausible plausible JJ cord-276598-tm0yj2sn 607 6 , , , cord-276598-tm0yj2sn 607 7 evidence evidence NN cord-276598-tm0yj2sn 607 8 by by IN cord-276598-tm0yj2sn 607 9 NMR NMR NNP cord-276598-tm0yj2sn 607 10 spectroscopy spectroscopy NN cord-276598-tm0yj2sn 607 11 suggests suggest VBZ cord-276598-tm0yj2sn 607 12 that that IN cord-276598-tm0yj2sn 607 13 in in IN cord-276598-tm0yj2sn 607 14 the the DT cord-276598-tm0yj2sn 607 15 first first JJ cord-276598-tm0yj2sn 607 16 step step NN cord-276598-tm0yj2sn 607 17 , , , cord-276598-tm0yj2sn 607 18 a a DT cord-276598-tm0yj2sn 607 19 reaction reaction NN cord-276598-tm0yj2sn 607 20 of of IN cord-276598-tm0yj2sn 607 21 the the DT cord-276598-tm0yj2sn 607 22 base base NN cord-276598-tm0yj2sn 607 23 and and CC cord-276598-tm0yj2sn 607 24 CCl CCl NNS cord-276598-tm0yj2sn 607 25 4 4 CD cord-276598-tm0yj2sn 607 26 results result NNS cord-276598-tm0yj2sn 607 27 in in IN cord-276598-tm0yj2sn 607 28 salt salt NN cord-276598-tm0yj2sn 607 29 formation formation NN cord-276598-tm0yj2sn 607 30 [ [ -LRB- cord-276598-tm0yj2sn 607 31 Et et NN cord-276598-tm0yj2sn 607 32 3 3 CD cord-276598-tm0yj2sn 607 33 NCl NCl NNS cord-276598-tm0yj2sn 607 34 ] ] -RRB- cord-276598-tm0yj2sn 607 35 + + CC cord-276598-tm0yj2sn 607 36 [ [ -LRB- cord-276598-tm0yj2sn 607 37 CCl CCl NNS cord-276598-tm0yj2sn 607 38 3 3 CD cord-276598-tm0yj2sn 607 39 ] ] -RRB- cord-276598-tm0yj2sn 607 40 − − NN cord-276598-tm0yj2sn 607 41 [ [ -LRB- cord-276598-tm0yj2sn 607 42 121 121 CD cord-276598-tm0yj2sn 607 43 ] ] -RRB- cord-276598-tm0yj2sn 607 44 . . . cord-276598-tm0yj2sn 608 1 The the DT cord-276598-tm0yj2sn 608 2 H H NNP cord-276598-tm0yj2sn 608 3 - - HYPH cord-276598-tm0yj2sn 608 4 P p NN cord-276598-tm0yj2sn 608 5 is be VBZ cord-276598-tm0yj2sn 608 6 deprotonated deprotonate VBN cord-276598-tm0yj2sn 608 7 by by IN cord-276598-tm0yj2sn 608 8 [ [ -LRB- cord-276598-tm0yj2sn 608 9 CCl CCl NNS cord-276598-tm0yj2sn 608 10 3 3 CD cord-276598-tm0yj2sn 608 11 ] ] -RRB- cord-276598-tm0yj2sn 608 12 − − NNP cord-276598-tm0yj2sn 608 13 to to TO cord-276598-tm0yj2sn 608 14 form form VB cord-276598-tm0yj2sn 608 15 CHCl CHCl NNS cord-276598-tm0yj2sn 608 16 3 3 CD cord-276598-tm0yj2sn 608 17 and and CC cord-276598-tm0yj2sn 608 18 anionic anionic JJ cord-276598-tm0yj2sn 608 19 phosphite phosphite NNP cord-276598-tm0yj2sn 608 20 , , , cord-276598-tm0yj2sn 608 21 which which WDT cord-276598-tm0yj2sn 608 22 reacts react VBZ cord-276598-tm0yj2sn 608 23 further further RB cord-276598-tm0yj2sn 608 24 with with IN cord-276598-tm0yj2sn 608 25 [ [ -LRB- cord-276598-tm0yj2sn 608 26 Et et NN cord-276598-tm0yj2sn 608 27 3 3 CD cord-276598-tm0yj2sn 608 28 NCl NCl NNS cord-276598-tm0yj2sn 608 29 ] ] -RRB- cord-276598-tm0yj2sn 608 30 + + SYM cord-276598-tm0yj2sn 608 31 to to TO cord-276598-tm0yj2sn 608 32 form form VB cord-276598-tm0yj2sn 608 33 ( ( -LRB- cord-276598-tm0yj2sn 608 34 RO ro NN cord-276598-tm0yj2sn 608 35 ) ) -RRB- cord-276598-tm0yj2sn 608 36 2 2 CD cord-276598-tm0yj2sn 609 1 P(O)Cl P(O)Cl NNP cord-276598-tm0yj2sn 609 2 ( ( -LRB- cord-276598-tm0yj2sn 609 3 dACP dacp NN cord-276598-tm0yj2sn 609 4 ; ; : cord-276598-tm0yj2sn 609 5 R r NN cord-276598-tm0yj2sn 609 6 = = NN cord-276598-tm0yj2sn 609 7 alkyl alkyl NN cord-276598-tm0yj2sn 609 8 ) ) -RRB- cord-276598-tm0yj2sn 609 9 . . . cord-276598-tm0yj2sn 610 1 In in IN cord-276598-tm0yj2sn 610 2 the the DT cord-276598-tm0yj2sn 610 3 second second JJ cord-276598-tm0yj2sn 610 4 step step NN cord-276598-tm0yj2sn 610 5 , , , cord-276598-tm0yj2sn 610 6 dACP dacp NN cord-276598-tm0yj2sn 610 7 reacts react VBZ cord-276598-tm0yj2sn 610 8 with with IN cord-276598-tm0yj2sn 610 9 amine amine NN cord-276598-tm0yj2sn 610 10 to to TO cord-276598-tm0yj2sn 610 11 give give VB cord-276598-tm0yj2sn 610 12 the the DT cord-276598-tm0yj2sn 610 13 product product NN cord-276598-tm0yj2sn 610 14 . . . cord-276598-tm0yj2sn 611 1 desired desire VBN cord-276598-tm0yj2sn 611 2 product product NN cord-276598-tm0yj2sn 611 3 is be VBZ cord-276598-tm0yj2sn 611 4 formed form VBN cord-276598-tm0yj2sn 611 5 in in IN cord-276598-tm0yj2sn 611 6 the the DT cord-276598-tm0yj2sn 611 7 second second JJ cord-276598-tm0yj2sn 611 8 step step NN cord-276598-tm0yj2sn 612 1 when when WRB cord-276598-tm0yj2sn 612 2 the the DT cord-276598-tm0yj2sn 612 3 ( ( -LRB- cord-276598-tm0yj2sn 612 4 trichloromethyl)phosphonate trichloromethyl)phosphonate NNP cord-276598-tm0yj2sn 612 5 reacts react NNS cord-276598-tm0yj2sn 612 6 with with IN cord-276598-tm0yj2sn 612 7 amine amine NN cord-276598-tm0yj2sn 612 8 , , , cord-276598-tm0yj2sn 612 9 forming form VBG cord-276598-tm0yj2sn 612 10 also also RB cord-276598-tm0yj2sn 612 11 CHCl3 chcl3 VB cord-276598-tm0yj2sn 612 12 in in IN cord-276598-tm0yj2sn 612 13 the the DT cord-276598-tm0yj2sn 612 14 process process NN cord-276598-tm0yj2sn 612 15 ( ( -LRB- cord-276598-tm0yj2sn 612 16 Scheme scheme NN cord-276598-tm0yj2sn 612 17 18 18 CD cord-276598-tm0yj2sn 612 18 ) ) -RRB- cord-276598-tm0yj2sn 612 19 . . . cord-276598-tm0yj2sn 613 1 Although although IN cord-276598-tm0yj2sn 613 2 this this DT cord-276598-tm0yj2sn 613 3 mechanism mechanism NN cord-276598-tm0yj2sn 613 4 is be VBZ cord-276598-tm0yj2sn 613 5 plausible plausible JJ cord-276598-tm0yj2sn 613 6 , , , cord-276598-tm0yj2sn 613 7 evidence evidence NN cord-276598-tm0yj2sn 613 8 by by IN cord-276598-tm0yj2sn 613 9 NMR NMR NNP cord-276598-tm0yj2sn 613 10 spectroscopy spectroscopy NN cord-276598-tm0yj2sn 613 11 suggests suggest VBZ cord-276598-tm0yj2sn 613 12 that that IN cord-276598-tm0yj2sn 613 13 in in IN cord-276598-tm0yj2sn 613 14 the the DT cord-276598-tm0yj2sn 613 15 first first JJ cord-276598-tm0yj2sn 613 16 step step NN cord-276598-tm0yj2sn 613 17 , , , cord-276598-tm0yj2sn 613 18 a a DT cord-276598-tm0yj2sn 613 19 reaction reaction NN cord-276598-tm0yj2sn 613 20 of of IN cord-276598-tm0yj2sn 613 21 the the DT cord-276598-tm0yj2sn 613 22 base base NN cord-276598-tm0yj2sn 613 23 and and CC cord-276598-tm0yj2sn 613 24 CCl4 ccl4 NN cord-276598-tm0yj2sn 613 25 results result NNS cord-276598-tm0yj2sn 613 26 in in IN cord-276598-tm0yj2sn 613 27 salt salt NN cord-276598-tm0yj2sn 613 28 formation formation NN cord-276598-tm0yj2sn 613 29 [ [ -LRB- cord-276598-tm0yj2sn 613 30 Et3NCl et3ncl NN cord-276598-tm0yj2sn 613 31 ] ] -RRB- cord-276598-tm0yj2sn 613 32 + + CC cord-276598-tm0yj2sn 613 33 [ [ -LRB- cord-276598-tm0yj2sn 613 34 CCl3 CCl3 NNP cord-276598-tm0yj2sn 613 35 ] ] -RRB- cord-276598-tm0yj2sn 613 36 − − NNP cord-276598-tm0yj2sn 613 37 [ [ -LRB- cord-276598-tm0yj2sn 613 38 121 121 CD cord-276598-tm0yj2sn 613 39 ] ] -RRB- cord-276598-tm0yj2sn 613 40 . . . cord-276598-tm0yj2sn 614 1 The the DT cord-276598-tm0yj2sn 614 2 H H NNP cord-276598-tm0yj2sn 614 3 - - HYPH cord-276598-tm0yj2sn 614 4 P p NN cord-276598-tm0yj2sn 614 5 is be VBZ cord-276598-tm0yj2sn 614 6 deprotonated deprotonate VBN cord-276598-tm0yj2sn 614 7 by by IN cord-276598-tm0yj2sn 614 8 [ [ -LRB- cord-276598-tm0yj2sn 614 9 CCl3 CCl3 NNP cord-276598-tm0yj2sn 614 10 ] ] -RRB- cord-276598-tm0yj2sn 614 11 − − NNP cord-276598-tm0yj2sn 614 12 to to TO cord-276598-tm0yj2sn 614 13 form form VB cord-276598-tm0yj2sn 614 14 CHCl3 CHCl3 NNP cord-276598-tm0yj2sn 614 15 and and CC cord-276598-tm0yj2sn 614 16 anionic anionic JJ cord-276598-tm0yj2sn 614 17 phosphite phosphite NNP cord-276598-tm0yj2sn 614 18 , , , cord-276598-tm0yj2sn 614 19 which which WDT cord-276598-tm0yj2sn 614 20 reacts react VBZ cord-276598-tm0yj2sn 614 21 further further RB cord-276598-tm0yj2sn 614 22 with with IN cord-276598-tm0yj2sn 614 23 [ [ -LRB- cord-276598-tm0yj2sn 614 24 Et3NCl Et3NCl NNP cord-276598-tm0yj2sn 614 25 ] ] -RRB- cord-276598-tm0yj2sn 614 26 + + SYM cord-276598-tm0yj2sn 614 27 to to TO cord-276598-tm0yj2sn 614 28 form form VB cord-276598-tm0yj2sn 614 29 ( ( -LRB- cord-276598-tm0yj2sn 615 1 RO)2P(O)Cl RO)2P(O)Cl NNP cord-276598-tm0yj2sn 615 2 ( ( -LRB- cord-276598-tm0yj2sn 615 3 dACP dacp NN cord-276598-tm0yj2sn 615 4 ; ; : cord-276598-tm0yj2sn 615 5 R r NN cord-276598-tm0yj2sn 615 6 = = NN cord-276598-tm0yj2sn 615 7 alkyl alkyl NN cord-276598-tm0yj2sn 615 8 ) ) -RRB- cord-276598-tm0yj2sn 615 9 . . . cord-276598-tm0yj2sn 616 1 In in IN cord-276598-tm0yj2sn 616 2 the the DT cord-276598-tm0yj2sn 616 3 second second JJ cord-276598-tm0yj2sn 616 4 step step NN cord-276598-tm0yj2sn 616 5 , , , cord-276598-tm0yj2sn 616 6 dACP dacp NN cord-276598-tm0yj2sn 616 7 reacts react VBZ cord-276598-tm0yj2sn 616 8 with with IN cord-276598-tm0yj2sn 616 9 amine amine NN cord-276598-tm0yj2sn 616 10 to to TO cord-276598-tm0yj2sn 616 11 give give VB cord-276598-tm0yj2sn 616 12 the the DT cord-276598-tm0yj2sn 616 13 product product NN cord-276598-tm0yj2sn 616 14 . . . cord-276598-tm0yj2sn 617 1 Scheme scheme NN cord-276598-tm0yj2sn 617 2 18 18 CD cord-276598-tm0yj2sn 617 3 . . . cord-276598-tm0yj2sn 618 1 Atherton Atherton NNP cord-276598-tm0yj2sn 618 2 - - HYPH cord-276598-tm0yj2sn 618 3 Todd Todd NNP cord-276598-tm0yj2sn 618 4 mechanism mechanism NN cord-276598-tm0yj2sn 618 5 proposed propose VBN cord-276598-tm0yj2sn 618 6 for for IN cord-276598-tm0yj2sn 618 7 the the DT cord-276598-tm0yj2sn 618 8 formation formation NN cord-276598-tm0yj2sn 618 9 of of IN cord-276598-tm0yj2sn 618 10 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 618 11 . . . cord-276598-tm0yj2sn 619 1 For for IN cord-276598-tm0yj2sn 619 2 the the DT cord-276598-tm0yj2sn 619 3 modified modify VBN cord-276598-tm0yj2sn 619 4 Atherton Atherton NNP cord-276598-tm0yj2sn 619 5 - - HYPH cord-276598-tm0yj2sn 619 6 Todd Todd NNP cord-276598-tm0yj2sn 619 7 reaction reaction NN cord-276598-tm0yj2sn 619 8 , , , cord-276598-tm0yj2sn 619 9 the the DT cord-276598-tm0yj2sn 619 10 two two CD cord-276598-tm0yj2sn 619 11 - - HYPH cord-276598-tm0yj2sn 619 12 step step NN cord-276598-tm0yj2sn 619 13 mechanistic mechanistic JJ cord-276598-tm0yj2sn 619 14 process process NN cord-276598-tm0yj2sn 619 15 involves involve VBZ cord-276598-tm0yj2sn 619 16 the the DT cord-276598-tm0yj2sn 619 17 deprotonation deprotonation NN cord-276598-tm0yj2sn 619 18 of of IN cord-276598-tm0yj2sn 619 19 H H NNP cord-276598-tm0yj2sn 619 20 - - HYPH cord-276598-tm0yj2sn 619 21 P p NN cord-276598-tm0yj2sn 619 22 by by IN cord-276598-tm0yj2sn 619 23 DBU DBU NNP cord-276598-tm0yj2sn 619 24 , , , cord-276598-tm0yj2sn 619 25 and and CC cord-276598-tm0yj2sn 619 26 the the DT cord-276598-tm0yj2sn 619 27 radical radical JJ cord-276598-tm0yj2sn 619 28 formed form VBN cord-276598-tm0yj2sn 619 29 is be VBZ cord-276598-tm0yj2sn 619 30 autoxidized autoxidize VBN cord-276598-tm0yj2sn 619 31 by by IN cord-276598-tm0yj2sn 619 32 O2 O2 NNP cord-276598-tm0yj2sn 619 33 before before IN cord-276598-tm0yj2sn 619 34 it -PRON- PRP cord-276598-tm0yj2sn 619 35 abstracts abstract VBZ cord-276598-tm0yj2sn 619 36 chlorine chlorine NN cord-276598-tm0yj2sn 619 37 from from IN cord-276598-tm0yj2sn 619 38 CHCl3 CHCl3 NNP cord-276598-tm0yj2sn 619 39 to to TO cord-276598-tm0yj2sn 619 40 form form VB cord-276598-tm0yj2sn 619 41 dACP dACP . cord-276598-tm0yj2sn 620 1 ( ( -LRB- cord-276598-tm0yj2sn 620 2 Scheme scheme NN cord-276598-tm0yj2sn 620 3 19 19 CD cord-276598-tm0yj2sn 620 4 ) ) -RRB- cord-276598-tm0yj2sn 620 5 [ [ -LRB- cord-276598-tm0yj2sn 620 6 95 95 CD cord-276598-tm0yj2sn 620 7 ] ] -RRB- cord-276598-tm0yj2sn 620 8 . . . cord-276598-tm0yj2sn 621 1 The the DT cord-276598-tm0yj2sn 621 2 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 621 3 substitution substitution NN cord-276598-tm0yj2sn 621 4 of of IN cord-276598-tm0yj2sn 621 5 dACP dacp NN cord-276598-tm0yj2sn 621 6 by by IN cord-276598-tm0yj2sn 621 7 the the DT cord-276598-tm0yj2sn 621 8 amine amine NN cord-276598-tm0yj2sn 621 9 affords afford VBZ cord-276598-tm0yj2sn 621 10 the the DT cord-276598-tm0yj2sn 621 11 P P NNP cord-276598-tm0yj2sn 621 12 - - HYPH cord-276598-tm0yj2sn 621 13 N n CD cord-276598-tm0yj2sn 621 14 product product NN cord-276598-tm0yj2sn 621 15 . . . cord-276598-tm0yj2sn 621 16 _SP cord-276598-tm0yj2sn 622 1 In in IN cord-276598-tm0yj2sn 622 2 the the DT cord-276598-tm0yj2sn 622 3 plausible plausible JJ cord-276598-tm0yj2sn 622 4 mechanism mechanism NN cord-276598-tm0yj2sn 622 5 for for IN cord-276598-tm0yj2sn 622 6 the the DT cord-276598-tm0yj2sn 622 7 direct direct JJ cord-276598-tm0yj2sn 622 8 conversion conversion NN cord-276598-tm0yj2sn 622 9 of of IN cord-276598-tm0yj2sn 622 10 diethyl diethyl JJ cord-276598-tm0yj2sn 622 11 hydrogen hydrogen NN cord-276598-tm0yj2sn 622 12 phosphate phosphate NN cord-276598-tm0yj2sn 622 13 , , , cord-276598-tm0yj2sn 622 14 hexamethyltriaminophosphine hexamethyltriaminophosphine NNP cord-276598-tm0yj2sn 622 15 P(NMe2)3 P(NMe2)3 NNP cord-276598-tm0yj2sn 622 16 is be VBZ cord-276598-tm0yj2sn 622 17 oxidized oxidize VBN cord-276598-tm0yj2sn 622 18 to to IN cord-276598-tm0yj2sn 622 19 hexamethyltriaminodibromophosphorane hexamethyltriaminodibromophosphorane NNP cord-276598-tm0yj2sn 622 20 ( ( -LRB- cord-276598-tm0yj2sn 622 21 ( ( -LRB- cord-276598-tm0yj2sn 622 22 Me2N)3PBr2 Me2N)3PBr2 NNP cord-276598-tm0yj2sn 622 23 ) ) -RRB- cord-276598-tm0yj2sn 622 24 which which WDT cord-276598-tm0yj2sn 622 25 is be VBZ cord-276598-tm0yj2sn 622 26 ionized ionize VBN cord-276598-tm0yj2sn 622 27 in in IN cord-276598-tm0yj2sn 622 28 solution solution NN cord-276598-tm0yj2sn 622 29 ( ( -LRB- cord-276598-tm0yj2sn 622 30 Scheme scheme NN cord-276598-tm0yj2sn 622 31 20 20 CD cord-276598-tm0yj2sn 622 32 ) ) -RRB- cord-276598-tm0yj2sn 622 33 [ [ -LRB- cord-276598-tm0yj2sn 622 34 90 90 CD cord-276598-tm0yj2sn 622 35 ] ] -RRB- cord-276598-tm0yj2sn 622 36 . . . cord-276598-tm0yj2sn 623 1 Subsequently subsequently RB cord-276598-tm0yj2sn 623 2 , , , cord-276598-tm0yj2sn 623 3 the the DT cord-276598-tm0yj2sn 623 4 ionized ionized JJ cord-276598-tm0yj2sn 623 5 ( ( -LRB- cord-276598-tm0yj2sn 623 6 Me2N)3PBr2 Me2N)3PBr2 NNP cord-276598-tm0yj2sn 623 7 and and CC cord-276598-tm0yj2sn 623 8 diethyl diethyl JJ cord-276598-tm0yj2sn 623 9 hydrogen hydrogen NN cord-276598-tm0yj2sn 623 10 phosphate phosphate NN cord-276598-tm0yj2sn 623 11 undergo undergo VBP cord-276598-tm0yj2sn 623 12 ligand ligand NN cord-276598-tm0yj2sn 623 13 exchange exchange NN cord-276598-tm0yj2sn 623 14 in in IN cord-276598-tm0yj2sn 623 15 the the DT cord-276598-tm0yj2sn 623 16 presence presence NN cord-276598-tm0yj2sn 623 17 of of IN cord-276598-tm0yj2sn 623 18 Et3N Et3N NNP cord-276598-tm0yj2sn 623 19 to to TO cord-276598-tm0yj2sn 623 20 form form VB cord-276598-tm0yj2sn 623 21 the the DT cord-276598-tm0yj2sn 623 22 Scheme Scheme NNP cord-276598-tm0yj2sn 623 23 18 18 CD cord-276598-tm0yj2sn 623 24 . . . cord-276598-tm0yj2sn 624 1 Atherton Atherton NNP cord-276598-tm0yj2sn 624 2 - - HYPH cord-276598-tm0yj2sn 624 3 Todd Todd NNP cord-276598-tm0yj2sn 624 4 mechanism mechanism NN cord-276598-tm0yj2sn 624 5 proposed propose VBN cord-276598-tm0yj2sn 624 6 for for IN cord-276598-tm0yj2sn 624 7 the the DT cord-276598-tm0yj2sn 624 8 formation formation NN cord-276598-tm0yj2sn 624 9 of of IN cord-276598-tm0yj2sn 624 10 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 624 11 . . . cord-276598-tm0yj2sn 625 1 For for IN cord-276598-tm0yj2sn 625 2 the the DT cord-276598-tm0yj2sn 625 3 modified modify VBN cord-276598-tm0yj2sn 625 4 Atherton Atherton NNP cord-276598-tm0yj2sn 625 5 - - HYPH cord-276598-tm0yj2sn 625 6 Todd Todd NNP cord-276598-tm0yj2sn 625 7 reaction reaction NN cord-276598-tm0yj2sn 625 8 , , , cord-276598-tm0yj2sn 625 9 the the DT cord-276598-tm0yj2sn 625 10 two two CD cord-276598-tm0yj2sn 625 11 - - HYPH cord-276598-tm0yj2sn 625 12 step step NN cord-276598-tm0yj2sn 625 13 mechanistic mechanistic JJ cord-276598-tm0yj2sn 625 14 process process NN cord-276598-tm0yj2sn 625 15 involves involve VBZ cord-276598-tm0yj2sn 625 16 the the DT cord-276598-tm0yj2sn 625 17 deprotonation deprotonation NN cord-276598-tm0yj2sn 625 18 of of IN cord-276598-tm0yj2sn 625 19 H H NNP cord-276598-tm0yj2sn 625 20 - - HYPH cord-276598-tm0yj2sn 625 21 P p NN cord-276598-tm0yj2sn 625 22 by by IN cord-276598-tm0yj2sn 625 23 DBU DBU NNP cord-276598-tm0yj2sn 625 24 , , , cord-276598-tm0yj2sn 625 25 and and CC cord-276598-tm0yj2sn 625 26 the the DT cord-276598-tm0yj2sn 625 27 radical radical JJ cord-276598-tm0yj2sn 625 28 formed form VBN cord-276598-tm0yj2sn 625 29 is be VBZ cord-276598-tm0yj2sn 625 30 autoxidized autoxidize VBN cord-276598-tm0yj2sn 625 31 by by IN cord-276598-tm0yj2sn 625 32 O o NN cord-276598-tm0yj2sn 625 33 2 2 CD cord-276598-tm0yj2sn 625 34 before before IN cord-276598-tm0yj2sn 625 35 it -PRON- PRP cord-276598-tm0yj2sn 625 36 abstracts abstract VBZ cord-276598-tm0yj2sn 625 37 chlorine chlorine NN cord-276598-tm0yj2sn 625 38 from from IN cord-276598-tm0yj2sn 625 39 CHCl CHCl NNS cord-276598-tm0yj2sn 625 40 3 3 CD cord-276598-tm0yj2sn 625 41 to to TO cord-276598-tm0yj2sn 625 42 form form VB cord-276598-tm0yj2sn 625 43 dACP dACP . cord-276598-tm0yj2sn 626 1 ( ( -LRB- cord-276598-tm0yj2sn 626 2 Scheme scheme NN cord-276598-tm0yj2sn 626 3 19 19 CD cord-276598-tm0yj2sn 626 4 ) ) -RRB- cord-276598-tm0yj2sn 626 5 [ [ -LRB- cord-276598-tm0yj2sn 626 6 95 95 CD cord-276598-tm0yj2sn 626 7 ] ] -RRB- cord-276598-tm0yj2sn 626 8 . . . cord-276598-tm0yj2sn 627 1 The the DT cord-276598-tm0yj2sn 627 2 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 627 3 substitution substitution NN cord-276598-tm0yj2sn 627 4 of of IN cord-276598-tm0yj2sn 627 5 dACP dacp NN cord-276598-tm0yj2sn 627 6 by by IN cord-276598-tm0yj2sn 627 7 the the DT cord-276598-tm0yj2sn 627 8 amine amine NN cord-276598-tm0yj2sn 627 9 affords afford VBZ cord-276598-tm0yj2sn 627 10 the the DT cord-276598-tm0yj2sn 627 11 P P NNP cord-276598-tm0yj2sn 627 12 - - HYPH cord-276598-tm0yj2sn 627 13 N n CD cord-276598-tm0yj2sn 627 14 product product NN cord-276598-tm0yj2sn 627 15 . . . cord-276598-tm0yj2sn 628 1 first first JJ cord-276598-tm0yj2sn 628 2 step step NN cord-276598-tm0yj2sn 628 3 , , , cord-276598-tm0yj2sn 628 4 from from IN cord-276598-tm0yj2sn 628 5 a a DT cord-276598-tm0yj2sn 628 6 reaction reaction NN cord-276598-tm0yj2sn 628 7 of of IN cord-276598-tm0yj2sn 628 8 ( ( -LRB- cord-276598-tm0yj2sn 628 9 RO)2P(O)H ro)2p(o)h NN cord-276598-tm0yj2sn 628 10 ( ( -LRB- cord-276598-tm0yj2sn 628 11 H h NN cord-276598-tm0yj2sn 628 12 - - HYPH cord-276598-tm0yj2sn 628 13 P p NN cord-276598-tm0yj2sn 628 14 ; ; : cord-276598-tm0yj2sn 628 15 R r NN cord-276598-tm0yj2sn 628 16 = = NN cord-276598-tm0yj2sn 628 17 alkyl alkyl NN cord-276598-tm0yj2sn 628 18 ) ) -RRB- cord-276598-tm0yj2sn 628 19 and and CC cord-276598-tm0yj2sn 628 20 CCl4 ccl4 NN cord-276598-tm0yj2sn 628 21 in in IN cord-276598-tm0yj2sn 628 22 the the DT cord-276598-tm0yj2sn 628 23 presence presence NN cord-276598-tm0yj2sn 628 24 of of IN cord-276598-tm0yj2sn 628 25 Et3N Et3N NNP cord-276598-tm0yj2sn 628 26 [ [ -LRB- cord-276598-tm0yj2sn 628 27 78 78 CD cord-276598-tm0yj2sn 628 28 ] ] -RRB- cord-276598-tm0yj2sn 628 29 . . . cord-276598-tm0yj2sn 629 1 The the DT cord-276598-tm0yj2sn 629 2 desired desire VBN cord-276598-tm0yj2sn 629 3 product product NN cord-276598-tm0yj2sn 629 4 is be VBZ cord-276598-tm0yj2sn 629 5 formed form VBN cord-276598-tm0yj2sn 629 6 in in IN cord-276598-tm0yj2sn 629 7 the the DT cord-276598-tm0yj2sn 629 8 second second JJ cord-276598-tm0yj2sn 629 9 step step NN cord-276598-tm0yj2sn 630 1 when when WRB cord-276598-tm0yj2sn 630 2 the the DT cord-276598-tm0yj2sn 630 3 ( ( -LRB- cord-276598-tm0yj2sn 630 4 trichloromethyl)phosphonate trichloromethyl)phosphonate NNP cord-276598-tm0yj2sn 630 5 reacts react NNS cord-276598-tm0yj2sn 630 6 with with IN cord-276598-tm0yj2sn 630 7 amine amine NN cord-276598-tm0yj2sn 630 8 , , , cord-276598-tm0yj2sn 630 9 forming form VBG cord-276598-tm0yj2sn 630 10 also also RB cord-276598-tm0yj2sn 630 11 CHCl3 chcl3 VB cord-276598-tm0yj2sn 630 12 in in IN cord-276598-tm0yj2sn 630 13 the the DT cord-276598-tm0yj2sn 630 14 process process NN cord-276598-tm0yj2sn 630 15 ( ( -LRB- cord-276598-tm0yj2sn 630 16 Scheme scheme NN cord-276598-tm0yj2sn 630 17 18 18 CD cord-276598-tm0yj2sn 630 18 ) ) -RRB- cord-276598-tm0yj2sn 630 19 . . . cord-276598-tm0yj2sn 631 1 Although although IN cord-276598-tm0yj2sn 631 2 this this DT cord-276598-tm0yj2sn 631 3 mechanism mechanism NN cord-276598-tm0yj2sn 631 4 is be VBZ cord-276598-tm0yj2sn 631 5 plausible plausible JJ cord-276598-tm0yj2sn 631 6 , , , cord-276598-tm0yj2sn 631 7 evidence evidence NN cord-276598-tm0yj2sn 631 8 by by IN cord-276598-tm0yj2sn 631 9 NMR NMR NNP cord-276598-tm0yj2sn 631 10 spectroscopy spectroscopy NN cord-276598-tm0yj2sn 631 11 suggests suggest VBZ cord-276598-tm0yj2sn 631 12 that that IN cord-276598-tm0yj2sn 631 13 in in IN cord-276598-tm0yj2sn 631 14 the the DT cord-276598-tm0yj2sn 631 15 first first JJ cord-276598-tm0yj2sn 631 16 step step NN cord-276598-tm0yj2sn 631 17 , , , cord-276598-tm0yj2sn 631 18 a a DT cord-276598-tm0yj2sn 631 19 reaction reaction NN cord-276598-tm0yj2sn 631 20 of of IN cord-276598-tm0yj2sn 631 21 the the DT cord-276598-tm0yj2sn 631 22 base base NN cord-276598-tm0yj2sn 631 23 and and CC cord-276598-tm0yj2sn 631 24 CCl4 ccl4 NN cord-276598-tm0yj2sn 631 25 results result NNS cord-276598-tm0yj2sn 631 26 in in IN cord-276598-tm0yj2sn 631 27 salt salt NN cord-276598-tm0yj2sn 631 28 formation formation NN cord-276598-tm0yj2sn 631 29 [ [ -LRB- cord-276598-tm0yj2sn 631 30 Et3NCl et3ncl NN cord-276598-tm0yj2sn 631 31 ] ] -RRB- cord-276598-tm0yj2sn 631 32 + + CC cord-276598-tm0yj2sn 631 33 [ [ -LRB- cord-276598-tm0yj2sn 631 34 CCl3 CCl3 NNP cord-276598-tm0yj2sn 631 35 ] ] -RRB- cord-276598-tm0yj2sn 631 36 − − NNP cord-276598-tm0yj2sn 631 37 [ [ -LRB- cord-276598-tm0yj2sn 631 38 121 121 CD cord-276598-tm0yj2sn 631 39 ] ] -RRB- cord-276598-tm0yj2sn 631 40 . . . cord-276598-tm0yj2sn 632 1 The the DT cord-276598-tm0yj2sn 632 2 H H NNP cord-276598-tm0yj2sn 632 3 - - HYPH cord-276598-tm0yj2sn 632 4 P p NN cord-276598-tm0yj2sn 632 5 is be VBZ cord-276598-tm0yj2sn 632 6 deprotonated deprotonate VBN cord-276598-tm0yj2sn 632 7 by by IN cord-276598-tm0yj2sn 632 8 [ [ -LRB- cord-276598-tm0yj2sn 632 9 CCl3 CCl3 NNP cord-276598-tm0yj2sn 632 10 ] ] -RRB- cord-276598-tm0yj2sn 632 11 − − NNP cord-276598-tm0yj2sn 632 12 to to TO cord-276598-tm0yj2sn 632 13 form form VB cord-276598-tm0yj2sn 632 14 CHCl3 CHCl3 NNP cord-276598-tm0yj2sn 632 15 and and CC cord-276598-tm0yj2sn 632 16 anionic anionic JJ cord-276598-tm0yj2sn 632 17 phosphite phosphite NNP cord-276598-tm0yj2sn 632 18 , , , cord-276598-tm0yj2sn 632 19 which which WDT cord-276598-tm0yj2sn 632 20 reacts react VBZ cord-276598-tm0yj2sn 632 21 further further RB cord-276598-tm0yj2sn 632 22 with with IN cord-276598-tm0yj2sn 632 23 [ [ -LRB- cord-276598-tm0yj2sn 632 24 Et3NCl Et3NCl NNP cord-276598-tm0yj2sn 632 25 ] ] -RRB- cord-276598-tm0yj2sn 632 26 + + SYM cord-276598-tm0yj2sn 632 27 to to TO cord-276598-tm0yj2sn 632 28 form form VB cord-276598-tm0yj2sn 632 29 ( ( -LRB- cord-276598-tm0yj2sn 633 1 RO)2P(O)Cl RO)2P(O)Cl NNP cord-276598-tm0yj2sn 633 2 ( ( -LRB- cord-276598-tm0yj2sn 633 3 dACP dacp NN cord-276598-tm0yj2sn 633 4 ; ; : cord-276598-tm0yj2sn 633 5 R r NN cord-276598-tm0yj2sn 633 6 = = NN cord-276598-tm0yj2sn 633 7 alkyl alkyl NN cord-276598-tm0yj2sn 633 8 ) ) -RRB- cord-276598-tm0yj2sn 633 9 . . . cord-276598-tm0yj2sn 634 1 In in IN cord-276598-tm0yj2sn 634 2 the the DT cord-276598-tm0yj2sn 634 3 second second JJ cord-276598-tm0yj2sn 634 4 step step NN cord-276598-tm0yj2sn 634 5 , , , cord-276598-tm0yj2sn 634 6 dACP dacp NN cord-276598-tm0yj2sn 634 7 reacts react VBZ cord-276598-tm0yj2sn 634 8 with with IN cord-276598-tm0yj2sn 634 9 amine amine NN cord-276598-tm0yj2sn 634 10 to to TO cord-276598-tm0yj2sn 634 11 give give VB cord-276598-tm0yj2sn 634 12 the the DT cord-276598-tm0yj2sn 634 13 product product NN cord-276598-tm0yj2sn 634 14 . . . cord-276598-tm0yj2sn 635 1 Scheme scheme NN cord-276598-tm0yj2sn 635 2 18 18 CD cord-276598-tm0yj2sn 635 3 . . . cord-276598-tm0yj2sn 636 1 Atherton Atherton NNP cord-276598-tm0yj2sn 636 2 - - HYPH cord-276598-tm0yj2sn 636 3 Todd Todd NNP cord-276598-tm0yj2sn 636 4 mechanism mechanism NN cord-276598-tm0yj2sn 636 5 proposed propose VBN cord-276598-tm0yj2sn 636 6 for for IN cord-276598-tm0yj2sn 636 7 the the DT cord-276598-tm0yj2sn 636 8 formation formation NN cord-276598-tm0yj2sn 636 9 of of IN cord-276598-tm0yj2sn 636 10 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 636 11 . . . cord-276598-tm0yj2sn 637 1 For for IN cord-276598-tm0yj2sn 637 2 the the DT cord-276598-tm0yj2sn 637 3 modified modify VBN cord-276598-tm0yj2sn 637 4 Atherton Atherton NNP cord-276598-tm0yj2sn 637 5 - - HYPH cord-276598-tm0yj2sn 637 6 Todd Todd NNP cord-276598-tm0yj2sn 637 7 reaction reaction NN cord-276598-tm0yj2sn 637 8 , , , cord-276598-tm0yj2sn 637 9 the the DT cord-276598-tm0yj2sn 637 10 two two CD cord-276598-tm0yj2sn 637 11 - - HYPH cord-276598-tm0yj2sn 637 12 step step NN cord-276598-tm0yj2sn 637 13 mechanistic mechanistic JJ cord-276598-tm0yj2sn 637 14 process process NN cord-276598-tm0yj2sn 637 15 involves involve VBZ cord-276598-tm0yj2sn 637 16 the the DT cord-276598-tm0yj2sn 637 17 deprotonation deprotonation NN cord-276598-tm0yj2sn 637 18 of of IN cord-276598-tm0yj2sn 637 19 H H NNP cord-276598-tm0yj2sn 637 20 - - HYPH cord-276598-tm0yj2sn 637 21 P p NN cord-276598-tm0yj2sn 637 22 by by IN cord-276598-tm0yj2sn 637 23 DBU DBU NNP cord-276598-tm0yj2sn 637 24 , , , cord-276598-tm0yj2sn 637 25 and and CC cord-276598-tm0yj2sn 637 26 the the DT cord-276598-tm0yj2sn 637 27 radical radical JJ cord-276598-tm0yj2sn 637 28 formed form VBN cord-276598-tm0yj2sn 637 29 is be VBZ cord-276598-tm0yj2sn 637 30 autoxidized autoxidize VBN cord-276598-tm0yj2sn 637 31 by by IN cord-276598-tm0yj2sn 637 32 O2 O2 NNP cord-276598-tm0yj2sn 637 33 before before IN cord-276598-tm0yj2sn 637 34 it -PRON- PRP cord-276598-tm0yj2sn 637 35 abstracts abstract VBZ cord-276598-tm0yj2sn 637 36 chlorine chlorine NN cord-276598-tm0yj2sn 637 37 from from IN cord-276598-tm0yj2sn 637 38 CHCl3 CHCl3 NNP cord-276598-tm0yj2sn 637 39 to to TO cord-276598-tm0yj2sn 637 40 form form VB cord-276598-tm0yj2sn 637 41 dACP dACP . cord-276598-tm0yj2sn 638 1 ( ( -LRB- cord-276598-tm0yj2sn 638 2 Scheme scheme NN cord-276598-tm0yj2sn 638 3 19 19 CD cord-276598-tm0yj2sn 638 4 ) ) -RRB- cord-276598-tm0yj2sn 638 5 [ [ -LRB- cord-276598-tm0yj2sn 638 6 95 95 CD cord-276598-tm0yj2sn 638 7 ] ] -RRB- cord-276598-tm0yj2sn 638 8 . . . cord-276598-tm0yj2sn 639 1 The the DT cord-276598-tm0yj2sn 639 2 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 639 3 substitution substitution NN cord-276598-tm0yj2sn 639 4 of of IN cord-276598-tm0yj2sn 639 5 dACP dacp NN cord-276598-tm0yj2sn 639 6 by by IN cord-276598-tm0yj2sn 639 7 the the DT cord-276598-tm0yj2sn 639 8 amine amine NN cord-276598-tm0yj2sn 639 9 affords afford VBZ cord-276598-tm0yj2sn 639 10 the the DT cord-276598-tm0yj2sn 639 11 P P NNP cord-276598-tm0yj2sn 639 12 - - HYPH cord-276598-tm0yj2sn 639 13 N n CD cord-276598-tm0yj2sn 639 14 product product NN cord-276598-tm0yj2sn 639 15 . . . cord-276598-tm0yj2sn 639 16 _SP cord-276598-tm0yj2sn 640 1 In in IN cord-276598-tm0yj2sn 640 2 the the DT cord-276598-tm0yj2sn 640 3 plausible plausible JJ cord-276598-tm0yj2sn 640 4 mechanism mechanism NN cord-276598-tm0yj2sn 640 5 for for IN cord-276598-tm0yj2sn 640 6 the the DT cord-276598-tm0yj2sn 640 7 direct direct JJ cord-276598-tm0yj2sn 640 8 conversion conversion NN cord-276598-tm0yj2sn 640 9 of of IN cord-276598-tm0yj2sn 640 10 diethyl diethyl JJ cord-276598-tm0yj2sn 640 11 hydrogen hydrogen NN cord-276598-tm0yj2sn 640 12 phosphate phosphate NN cord-276598-tm0yj2sn 640 13 , , , cord-276598-tm0yj2sn 640 14 hexamethyltriaminophosphine hexamethyltriaminophosphine NNP cord-276598-tm0yj2sn 640 15 P(NMe2)3 P(NMe2)3 NNP cord-276598-tm0yj2sn 640 16 is be VBZ cord-276598-tm0yj2sn 640 17 oxidized oxidize VBN cord-276598-tm0yj2sn 640 18 to to IN cord-276598-tm0yj2sn 640 19 hexamethyltriaminodibromophosphorane hexamethyltriaminodibromophosphorane NNP cord-276598-tm0yj2sn 640 20 ( ( -LRB- cord-276598-tm0yj2sn 640 21 ( ( -LRB- cord-276598-tm0yj2sn 640 22 Me2N)3PBr2 Me2N)3PBr2 NNP cord-276598-tm0yj2sn 640 23 ) ) -RRB- cord-276598-tm0yj2sn 640 24 which which WDT cord-276598-tm0yj2sn 640 25 is be VBZ cord-276598-tm0yj2sn 640 26 ionized ionize VBN cord-276598-tm0yj2sn 640 27 in in IN cord-276598-tm0yj2sn 640 28 solution solution NN cord-276598-tm0yj2sn 640 29 ( ( -LRB- cord-276598-tm0yj2sn 640 30 Scheme scheme NN cord-276598-tm0yj2sn 640 31 20 20 CD cord-276598-tm0yj2sn 640 32 ) ) -RRB- cord-276598-tm0yj2sn 640 33 [ [ -LRB- cord-276598-tm0yj2sn 640 34 90 90 CD cord-276598-tm0yj2sn 640 35 ] ] -RRB- cord-276598-tm0yj2sn 640 36 . . . cord-276598-tm0yj2sn 641 1 Subsequently subsequently RB cord-276598-tm0yj2sn 641 2 , , , cord-276598-tm0yj2sn 641 3 the the DT cord-276598-tm0yj2sn 641 4 ionized ionized JJ cord-276598-tm0yj2sn 641 5 ( ( -LRB- cord-276598-tm0yj2sn 641 6 Me2N)3PBr2 Me2N)3PBr2 NNP cord-276598-tm0yj2sn 641 7 and and CC cord-276598-tm0yj2sn 641 8 diethyl diethyl JJ cord-276598-tm0yj2sn 641 9 hydrogen hydrogen NN cord-276598-tm0yj2sn 641 10 phosphate phosphate NN cord-276598-tm0yj2sn 641 11 undergo undergo VBP cord-276598-tm0yj2sn 641 12 ligand ligand NN cord-276598-tm0yj2sn 641 13 exchange exchange NN cord-276598-tm0yj2sn 641 14 in in IN cord-276598-tm0yj2sn 641 15 the the DT cord-276598-tm0yj2sn 641 16 presence presence NN cord-276598-tm0yj2sn 641 17 of of IN cord-276598-tm0yj2sn 641 18 Et3N Et3N NNP cord-276598-tm0yj2sn 641 19 to to TO cord-276598-tm0yj2sn 641 20 form form VB cord-276598-tm0yj2sn 641 21 the the DT cord-276598-tm0yj2sn 641 22 Scheme Scheme NNP cord-276598-tm0yj2sn 641 23 19 19 CD cord-276598-tm0yj2sn 641 24 . . . cord-276598-tm0yj2sn 642 1 Modified Modified NNP cord-276598-tm0yj2sn 642 2 Atherton Atherton NNP cord-276598-tm0yj2sn 642 3 - - HYPH cord-276598-tm0yj2sn 642 4 Todd Todd NNP cord-276598-tm0yj2sn 642 5 mechanism mechanism NN cord-276598-tm0yj2sn 642 6 proposed propose VBN cord-276598-tm0yj2sn 642 7 in in IN cord-276598-tm0yj2sn 642 8 the the DT cord-276598-tm0yj2sn 642 9 formation formation NN cord-276598-tm0yj2sn 642 10 of of IN cord-276598-tm0yj2sn 642 11 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 642 12 . . . cord-276598-tm0yj2sn 643 1 In in IN cord-276598-tm0yj2sn 643 2 the the DT cord-276598-tm0yj2sn 643 3 plausible plausible JJ cord-276598-tm0yj2sn 643 4 mechanism mechanism NN cord-276598-tm0yj2sn 643 5 for for IN cord-276598-tm0yj2sn 643 6 the the DT cord-276598-tm0yj2sn 643 7 direct direct JJ cord-276598-tm0yj2sn 643 8 conversion conversion NN cord-276598-tm0yj2sn 643 9 of of IN cord-276598-tm0yj2sn 643 10 diethyl diethyl JJ cord-276598-tm0yj2sn 643 11 hydrogen hydrogen NN cord-276598-tm0yj2sn 643 12 phosphate phosphate NN cord-276598-tm0yj2sn 643 13 , , , cord-276598-tm0yj2sn 643 14 hexamethyltriaminophosphine hexamethyltriaminophosphine NNP cord-276598-tm0yj2sn 643 15 P(NMe P(NMe NNP cord-276598-tm0yj2sn 643 16 2 2 CD cord-276598-tm0yj2sn 643 17 ) ) -RRB- cord-276598-tm0yj2sn 643 18 3 3 CD cord-276598-tm0yj2sn 643 19 is be VBZ cord-276598-tm0yj2sn 643 20 oxidized oxidize VBN cord-276598-tm0yj2sn 643 21 to to IN cord-276598-tm0yj2sn 643 22 hexamethyltriaminodibromophosphorane hexamethyltriaminodibromophosphorane NNP cord-276598-tm0yj2sn 643 23 ( ( -LRB- cord-276598-tm0yj2sn 643 24 ( ( -LRB- cord-276598-tm0yj2sn 643 25 Me Me NNP cord-276598-tm0yj2sn 643 26 2 2 CD cord-276598-tm0yj2sn 643 27 N n CD cord-276598-tm0yj2sn 643 28 ) ) -RRB- cord-276598-tm0yj2sn 643 29 3 3 CD cord-276598-tm0yj2sn 643 30 PBr PBr NNS cord-276598-tm0yj2sn 643 31 2 2 CD cord-276598-tm0yj2sn 643 32 ) ) -RRB- cord-276598-tm0yj2sn 643 33 which which WDT cord-276598-tm0yj2sn 643 34 is be VBZ cord-276598-tm0yj2sn 643 35 ionized ionize VBN cord-276598-tm0yj2sn 643 36 in in IN cord-276598-tm0yj2sn 643 37 solution solution NN cord-276598-tm0yj2sn 643 38 ( ( -LRB- cord-276598-tm0yj2sn 643 39 Scheme scheme NN cord-276598-tm0yj2sn 643 40 20 20 CD cord-276598-tm0yj2sn 643 41 ) ) -RRB- cord-276598-tm0yj2sn 643 42 [ [ -LRB- cord-276598-tm0yj2sn 643 43 90 90 CD cord-276598-tm0yj2sn 643 44 ] ] -RRB- cord-276598-tm0yj2sn 643 45 . . . cord-276598-tm0yj2sn 644 1 Subsequently subsequently RB cord-276598-tm0yj2sn 644 2 , , , cord-276598-tm0yj2sn 644 3 the the DT cord-276598-tm0yj2sn 644 4 ionized ionized JJ cord-276598-tm0yj2sn 644 5 ( ( -LRB- cord-276598-tm0yj2sn 644 6 Me Me NNP cord-276598-tm0yj2sn 644 7 2 2 CD cord-276598-tm0yj2sn 644 8 N n CD cord-276598-tm0yj2sn 644 9 ) ) -RRB- cord-276598-tm0yj2sn 644 10 3 3 CD cord-276598-tm0yj2sn 644 11 PBr PBr NNS cord-276598-tm0yj2sn 644 12 2 2 CD cord-276598-tm0yj2sn 644 13 and and CC cord-276598-tm0yj2sn 644 14 diethyl diethyl NN cord-276598-tm0yj2sn 644 15 hydrogen hydrogen NN cord-276598-tm0yj2sn 644 16 phosphate phosphate NN cord-276598-tm0yj2sn 644 17 undergo undergo VBP cord-276598-tm0yj2sn 644 18 ligand ligand NN cord-276598-tm0yj2sn 644 19 exchange exchange NN cord-276598-tm0yj2sn 644 20 in in IN cord-276598-tm0yj2sn 644 21 the the DT cord-276598-tm0yj2sn 644 22 presence presence NN cord-276598-tm0yj2sn 644 23 of of IN cord-276598-tm0yj2sn 644 24 Et Et NNP cord-276598-tm0yj2sn 644 25 3 3 CD cord-276598-tm0yj2sn 644 26 N N NNP cord-276598-tm0yj2sn 644 27 to to TO cord-276598-tm0yj2sn 644 28 form form VB cord-276598-tm0yj2sn 644 29 the the DT cord-276598-tm0yj2sn 644 30 intermediate intermediate JJ cord-276598-tm0yj2sn 644 31 , , , cord-276598-tm0yj2sn 644 32 diethyl diethyl JJ cord-276598-tm0yj2sn 644 33 ( ( -LRB- cord-276598-tm0yj2sn 644 34 phosphaneyloxy)phosphonate phosphaneyloxy)phosphonate NNP cord-276598-tm0yj2sn 644 35 amino amino NN cord-276598-tm0yj2sn 644 36 - - HYPH cord-276598-tm0yj2sn 644 37 hydrazine hydrazine NN cord-276598-tm0yj2sn 644 38 - - HYPH cord-276598-tm0yj2sn 644 39 bromide bromide NN cord-276598-tm0yj2sn 644 40 salt salt NN cord-276598-tm0yj2sn 644 41 complex complex NN cord-276598-tm0yj2sn 644 42 . . . cord-276598-tm0yj2sn 645 1 Nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 645 2 attack attack NN cord-276598-tm0yj2sn 645 3 from from IN cord-276598-tm0yj2sn 645 4 the the DT cord-276598-tm0yj2sn 645 5 amine amine NN cord-276598-tm0yj2sn 645 6 onto onto IN cord-276598-tm0yj2sn 645 7 the the DT cord-276598-tm0yj2sn 645 8 positively positively RB cord-276598-tm0yj2sn 645 9 charged charge VBN cord-276598-tm0yj2sn 645 10 P p NN cord-276598-tm0yj2sn 645 11 results result NNS cord-276598-tm0yj2sn 645 12 in in IN cord-276598-tm0yj2sn 645 13 the the DT cord-276598-tm0yj2sn 645 14 diethyl diethyl NN cord-276598-tm0yj2sn 645 15 phosphoramidate phosphoramidate JJ cord-276598-tm0yj2sn 645 16 bromide bromide NN cord-276598-tm0yj2sn 645 17 salt salt NN cord-276598-tm0yj2sn 645 18 , , , cord-276598-tm0yj2sn 645 19 which which WDT cord-276598-tm0yj2sn 645 20 reacts react VBZ cord-276598-tm0yj2sn 645 21 with with IN cord-276598-tm0yj2sn 645 22 Et Et NNP cord-276598-tm0yj2sn 645 23 3 3 CD cord-276598-tm0yj2sn 645 24 N N NNP cord-276598-tm0yj2sn 645 25 to to TO cord-276598-tm0yj2sn 645 26 give give VB cord-276598-tm0yj2sn 645 27 the the DT cord-276598-tm0yj2sn 645 28 desired desire VBN cord-276598-tm0yj2sn 645 29 product product NN cord-276598-tm0yj2sn 645 30 with with IN cord-276598-tm0yj2sn 645 31 a a DT cord-276598-tm0yj2sn 645 32 concomitant concomitant JJ cord-276598-tm0yj2sn 645 33 elimination elimination NN cord-276598-tm0yj2sn 645 34 of of IN cord-276598-tm0yj2sn 645 35 triethylammonium triethylammonium NN cord-276598-tm0yj2sn 645 36 bromide bromide NN cord-276598-tm0yj2sn 645 37 . . . cord-276598-tm0yj2sn 646 1 Apart apart RB cord-276598-tm0yj2sn 646 2 from from IN cord-276598-tm0yj2sn 646 3 the the DT cord-276598-tm0yj2sn 646 4 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 646 5 Et Et NNP cord-276598-tm0yj2sn 646 6 3 3 CD cord-276598-tm0yj2sn 646 7 N n NN cord-276598-tm0yj2sn 646 8 salt salt NN cord-276598-tm0yj2sn 646 9 waste waste NN cord-276598-tm0yj2sn 646 10 generated generate VBN cord-276598-tm0yj2sn 646 11 , , , cord-276598-tm0yj2sn 646 12 the the DT cord-276598-tm0yj2sn 646 13 synthetic synthetic JJ cord-276598-tm0yj2sn 646 14 process process NN cord-276598-tm0yj2sn 646 15 is be VBZ cord-276598-tm0yj2sn 646 16 prone prone JJ cord-276598-tm0yj2sn 646 17 to to IN cord-276598-tm0yj2sn 646 18 the the DT cord-276598-tm0yj2sn 646 19 formation formation NN cord-276598-tm0yj2sn 646 20 of of IN cord-276598-tm0yj2sn 646 21 significant significant JJ cord-276598-tm0yj2sn 646 22 quantities quantity NNS cord-276598-tm0yj2sn 646 23 of of IN cord-276598-tm0yj2sn 646 24 pyrophosphate pyrophosphate NN cord-276598-tm0yj2sn 646 25 or or CC cord-276598-tm0yj2sn 646 26 phosphanetetraamine phosphanetetraamine JJ cord-276598-tm0yj2sn 646 27 bromide bromide NN cord-276598-tm0yj2sn 646 28 salt salt NN cord-276598-tm0yj2sn 646 29 side side NN cord-276598-tm0yj2sn 646 30 products product NNS cord-276598-tm0yj2sn 646 31 , , , cord-276598-tm0yj2sn 646 32 resulting result VBG cord-276598-tm0yj2sn 646 33 in in IN cord-276598-tm0yj2sn 646 34 a a DT cord-276598-tm0yj2sn 646 35 low low JJ cord-276598-tm0yj2sn 646 36 yield yield NN cord-276598-tm0yj2sn 646 37 . . . cord-276598-tm0yj2sn 647 1 Nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 647 2 attack attack NN cord-276598-tm0yj2sn 647 3 from from IN cord-276598-tm0yj2sn 647 4 the the DT cord-276598-tm0yj2sn 647 5 amine amine NN cord-276598-tm0yj2sn 647 6 onto onto IN cord-276598-tm0yj2sn 647 7 the the DT cord-276598-tm0yj2sn 647 8 positively positively RB cord-276598-tm0yj2sn 647 9 charged charge VBN cord-276598-tm0yj2sn 647 10 P p NN cord-276598-tm0yj2sn 647 11 results result NNS cord-276598-tm0yj2sn 647 12 in in IN cord-276598-tm0yj2sn 647 13 the the DT cord-276598-tm0yj2sn 647 14 diethyl diethyl NN cord-276598-tm0yj2sn 647 15 phosphoramidate phosphoramidate JJ cord-276598-tm0yj2sn 647 16 bromide bromide NN cord-276598-tm0yj2sn 647 17 salt salt NN cord-276598-tm0yj2sn 647 18 , , , cord-276598-tm0yj2sn 647 19 which which WDT cord-276598-tm0yj2sn 647 20 reacts react VBZ cord-276598-tm0yj2sn 647 21 with with IN cord-276598-tm0yj2sn 647 22 Et3N Et3N NNP cord-276598-tm0yj2sn 647 23 to to TO cord-276598-tm0yj2sn 647 24 give give VB cord-276598-tm0yj2sn 647 25 the the DT cord-276598-tm0yj2sn 647 26 desired desire VBN cord-276598-tm0yj2sn 647 27 product product NN cord-276598-tm0yj2sn 647 28 with with IN cord-276598-tm0yj2sn 647 29 a a DT cord-276598-tm0yj2sn 647 30 concomitant concomitant JJ cord-276598-tm0yj2sn 647 31 elimination elimination NN cord-276598-tm0yj2sn 647 32 of of IN cord-276598-tm0yj2sn 647 33 triethylammonium triethylammonium NN cord-276598-tm0yj2sn 647 34 bromide bromide NN cord-276598-tm0yj2sn 647 35 . . . cord-276598-tm0yj2sn 648 1 Apart apart RB cord-276598-tm0yj2sn 648 2 from from IN cord-276598-tm0yj2sn 648 3 the the DT cord-276598-tm0yj2sn 648 4 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 648 5 Et3N Et3N NNP cord-276598-tm0yj2sn 648 6 salt salt NN cord-276598-tm0yj2sn 648 7 waste waste NN cord-276598-tm0yj2sn 648 8 generated generate VBN cord-276598-tm0yj2sn 648 9 , , , cord-276598-tm0yj2sn 648 10 the the DT cord-276598-tm0yj2sn 648 11 synthetic synthetic JJ cord-276598-tm0yj2sn 648 12 process process NN cord-276598-tm0yj2sn 648 13 is be VBZ cord-276598-tm0yj2sn 648 14 prone prone JJ cord-276598-tm0yj2sn 648 15 to to IN cord-276598-tm0yj2sn 648 16 the the DT cord-276598-tm0yj2sn 648 17 formation formation NN cord-276598-tm0yj2sn 648 18 of of IN cord-276598-tm0yj2sn 648 19 significant significant JJ cord-276598-tm0yj2sn 648 20 quantities quantity NNS cord-276598-tm0yj2sn 648 21 of of IN cord-276598-tm0yj2sn 648 22 pyrophosphate pyrophosphate NN cord-276598-tm0yj2sn 648 23 or or CC cord-276598-tm0yj2sn 648 24 phosphanetetraamine phosphanetetraamine JJ cord-276598-tm0yj2sn 648 25 bromide bromide NN cord-276598-tm0yj2sn 648 26 salt salt NN cord-276598-tm0yj2sn 648 27 side side NN cord-276598-tm0yj2sn 648 28 products product NNS cord-276598-tm0yj2sn 648 29 , , , cord-276598-tm0yj2sn 648 30 resulting result VBG cord-276598-tm0yj2sn 648 31 in in IN cord-276598-tm0yj2sn 648 32 a a DT cord-276598-tm0yj2sn 648 33 low low JJ cord-276598-tm0yj2sn 648 34 yield yield NN cord-276598-tm0yj2sn 648 35 . . . cord-276598-tm0yj2sn 649 1 The the DT cord-276598-tm0yj2sn 649 2 mechanistic mechanistic JJ cord-276598-tm0yj2sn 649 3 steps step NNS cord-276598-tm0yj2sn 649 4 for for IN cord-276598-tm0yj2sn 649 5 the the DT cord-276598-tm0yj2sn 649 6 synthesis synthesis NN cord-276598-tm0yj2sn 649 7 of of IN cord-276598-tm0yj2sn 649 8 P P NNP cord-276598-tm0yj2sn 649 9 - - HYPH cord-276598-tm0yj2sn 649 10 N N NNP cord-276598-tm0yj2sn 649 11 via via IN cord-276598-tm0yj2sn 649 12 a a DT cord-276598-tm0yj2sn 649 13 salt salt NN cord-276598-tm0yj2sn 649 14 elimination elimination NN cord-276598-tm0yj2sn 649 15 route route NN cord-276598-tm0yj2sn 649 16 were be VBD cord-276598-tm0yj2sn 649 17 not not RB cord-276598-tm0yj2sn 649 18 proposed propose VBN cord-276598-tm0yj2sn 649 19 by by IN cord-276598-tm0yj2sn 649 20 Zwierzak Zwierzak NNP cord-276598-tm0yj2sn 649 21 et et FW cord-276598-tm0yj2sn 649 22 al al NNP cord-276598-tm0yj2sn 649 23 . . . cord-276598-tm0yj2sn 650 1 [ [ -LRB- cord-276598-tm0yj2sn 650 2 89 89 CD cord-276598-tm0yj2sn 650 3 ] ] -RRB- cord-276598-tm0yj2sn 650 4 ; ; : cord-276598-tm0yj2sn 650 5 however however RB cord-276598-tm0yj2sn 650 6 , , , cord-276598-tm0yj2sn 650 7 based base VBN cord-276598-tm0yj2sn 650 8 on on IN cord-276598-tm0yj2sn 650 9 the the DT cord-276598-tm0yj2sn 650 10 roles role NNS cord-276598-tm0yj2sn 650 11 of of IN cord-276598-tm0yj2sn 650 12 KHCO3 KHCO3 NNP cord-276598-tm0yj2sn 650 13 , , , cord-276598-tm0yj2sn 650 14 K2CO3 K2CO3 NNP cord-276598-tm0yj2sn 650 15 , , , cord-276598-tm0yj2sn 650 16 and and CC cord-276598-tm0yj2sn 650 17 [ [ -LRB- cord-276598-tm0yj2sn 650 18 n n NN cord-276598-tm0yj2sn 650 19 - - HYPH cord-276598-tm0yj2sn 650 20 Bu4N]Br Bu4N]Br NNP cord-276598-tm0yj2sn 650 21 as as IN cord-276598-tm0yj2sn 650 22 outlined outline VBN cord-276598-tm0yj2sn 650 23 in in IN cord-276598-tm0yj2sn 650 24 the the DT cord-276598-tm0yj2sn 650 25 paper paper NN cord-276598-tm0yj2sn 650 26 and and CC cord-276598-tm0yj2sn 650 27 a a DT cord-276598-tm0yj2sn 650 28 recently recently RB cord-276598-tm0yj2sn 650 29 proposed propose VBN cord-276598-tm0yj2sn 650 30 mechanism mechanism NN cord-276598-tm0yj2sn 650 31 for for IN cord-276598-tm0yj2sn 650 32 an an DT cord-276598-tm0yj2sn 650 33 Atherton Atherton NNP cord-276598-tm0yj2sn 650 34 - - HYPH cord-276598-tm0yj2sn 650 35 Todd Todd NNP cord-276598-tm0yj2sn 650 36 type type NN cord-276598-tm0yj2sn 650 37 reaction reaction NN cord-276598-tm0yj2sn 650 38 , , , cord-276598-tm0yj2sn 650 39 a a DT cord-276598-tm0yj2sn 650 40 probable probable JJ cord-276598-tm0yj2sn 650 41 mechanism mechanism NN cord-276598-tm0yj2sn 650 42 can can MD cord-276598-tm0yj2sn 650 43 be be VB cord-276598-tm0yj2sn 650 44 postulated postulate VBN cord-276598-tm0yj2sn 650 45 ( ( -LRB- cord-276598-tm0yj2sn 650 46 Scheme scheme NN cord-276598-tm0yj2sn 650 47 21 21 CD cord-276598-tm0yj2sn 650 48 ) ) -RRB- cord-276598-tm0yj2sn 650 49 [ [ -LRB- cord-276598-tm0yj2sn 650 50 121 121 CD cord-276598-tm0yj2sn 650 51 ] ] -RRB- cord-276598-tm0yj2sn 650 52 . . . cord-276598-tm0yj2sn 651 1 In in IN cord-276598-tm0yj2sn 651 2 the the DT cord-276598-tm0yj2sn 651 3 reacting react VBG cord-276598-tm0yj2sn 651 4 system system NN cord-276598-tm0yj2sn 651 5 , , , cord-276598-tm0yj2sn 651 6 the the DT cord-276598-tm0yj2sn 651 7 HCO3 HCO3 NNP cord-276598-tm0yj2sn 651 8 − − NNP cord-276598-tm0yj2sn 651 9 migrates migrate VBZ cord-276598-tm0yj2sn 651 10 to to IN cord-276598-tm0yj2sn 651 11 the the DT cord-276598-tm0yj2sn 651 12 The the DT cord-276598-tm0yj2sn 651 13 mechanistic mechanistic JJ cord-276598-tm0yj2sn 651 14 steps step NNS cord-276598-tm0yj2sn 651 15 for for IN cord-276598-tm0yj2sn 651 16 the the DT cord-276598-tm0yj2sn 651 17 synthesis synthesis NN cord-276598-tm0yj2sn 651 18 of of IN cord-276598-tm0yj2sn 651 19 P P NNP cord-276598-tm0yj2sn 651 20 - - HYPH cord-276598-tm0yj2sn 651 21 N N NNP cord-276598-tm0yj2sn 651 22 via via IN cord-276598-tm0yj2sn 651 23 a a DT cord-276598-tm0yj2sn 651 24 salt salt NN cord-276598-tm0yj2sn 651 25 elimination elimination NN cord-276598-tm0yj2sn 651 26 route route NN cord-276598-tm0yj2sn 651 27 were be VBD cord-276598-tm0yj2sn 651 28 not not RB cord-276598-tm0yj2sn 651 29 proposed propose VBN cord-276598-tm0yj2sn 651 30 by by IN cord-276598-tm0yj2sn 651 31 Zwierzak Zwierzak NNP cord-276598-tm0yj2sn 651 32 et et FW cord-276598-tm0yj2sn 651 33 al al NNP cord-276598-tm0yj2sn 651 34 . . . cord-276598-tm0yj2sn 652 1 [ [ -LRB- cord-276598-tm0yj2sn 652 2 89 89 CD cord-276598-tm0yj2sn 652 3 ] ] -RRB- cord-276598-tm0yj2sn 652 4 ; ; : cord-276598-tm0yj2sn 652 5 however however RB cord-276598-tm0yj2sn 652 6 , , , cord-276598-tm0yj2sn 652 7 based base VBN cord-276598-tm0yj2sn 652 8 on on IN cord-276598-tm0yj2sn 652 9 the the DT cord-276598-tm0yj2sn 652 10 roles role NNS cord-276598-tm0yj2sn 652 11 of of IN cord-276598-tm0yj2sn 652 12 KHCO KHCO NNP cord-276598-tm0yj2sn 652 13 3 3 CD cord-276598-tm0yj2sn 652 14 , , , cord-276598-tm0yj2sn 652 15 K K NNP cord-276598-tm0yj2sn 652 16 2 2 CD cord-276598-tm0yj2sn 652 17 CO CO NNP cord-276598-tm0yj2sn 652 18 3 3 CD cord-276598-tm0yj2sn 652 19 , , , cord-276598-tm0yj2sn 652 20 and and CC cord-276598-tm0yj2sn 652 21 [ [ -LRB- cord-276598-tm0yj2sn 652 22 n n NNP cord-276598-tm0yj2sn 652 23 - - HYPH cord-276598-tm0yj2sn 652 24 Bu Bu NNP cord-276598-tm0yj2sn 652 25 4 4 CD cord-276598-tm0yj2sn 652 26 N]Br N]Br NNP cord-276598-tm0yj2sn 652 27 as as IN cord-276598-tm0yj2sn 652 28 outlined outline VBN cord-276598-tm0yj2sn 652 29 in in IN cord-276598-tm0yj2sn 652 30 the the DT cord-276598-tm0yj2sn 652 31 paper paper NN cord-276598-tm0yj2sn 652 32 and and CC cord-276598-tm0yj2sn 652 33 a a DT cord-276598-tm0yj2sn 652 34 recently recently RB cord-276598-tm0yj2sn 652 35 proposed propose VBN cord-276598-tm0yj2sn 652 36 mechanism mechanism NN cord-276598-tm0yj2sn 652 37 for for IN cord-276598-tm0yj2sn 652 38 an an DT cord-276598-tm0yj2sn 652 39 Atherton Atherton NNP cord-276598-tm0yj2sn 652 40 - - HYPH cord-276598-tm0yj2sn 652 41 Todd Todd NNP cord-276598-tm0yj2sn 652 42 type type NN cord-276598-tm0yj2sn 652 43 reaction reaction NN cord-276598-tm0yj2sn 652 44 , , , cord-276598-tm0yj2sn 652 45 a a DT cord-276598-tm0yj2sn 652 46 probable probable JJ cord-276598-tm0yj2sn 652 47 mechanism mechanism NN cord-276598-tm0yj2sn 652 48 can can MD cord-276598-tm0yj2sn 652 49 be be VB cord-276598-tm0yj2sn 652 50 postulated postulate VBN cord-276598-tm0yj2sn 652 51 ( ( -LRB- cord-276598-tm0yj2sn 652 52 Scheme scheme NN cord-276598-tm0yj2sn 652 53 21 21 CD cord-276598-tm0yj2sn 652 54 ) ) -RRB- cord-276598-tm0yj2sn 652 55 [ [ -LRB- cord-276598-tm0yj2sn 652 56 121 121 CD cord-276598-tm0yj2sn 652 57 ] ] -RRB- cord-276598-tm0yj2sn 652 58 . . . cord-276598-tm0yj2sn 653 1 In in IN cord-276598-tm0yj2sn 653 2 the the DT cord-276598-tm0yj2sn 653 3 reacting react VBG cord-276598-tm0yj2sn 653 4 system system NN cord-276598-tm0yj2sn 653 5 , , , cord-276598-tm0yj2sn 653 6 the the DT cord-276598-tm0yj2sn 653 7 HCO HCO NNP cord-276598-tm0yj2sn 653 8 3 3 CD cord-276598-tm0yj2sn 653 9 − − NNP cord-276598-tm0yj2sn 653 10 migrates migrate VBZ cord-276598-tm0yj2sn 653 11 to to IN cord-276598-tm0yj2sn 653 12 the the DT cord-276598-tm0yj2sn 653 13 organic organic JJ cord-276598-tm0yj2sn 653 14 phase phase NN cord-276598-tm0yj2sn 653 15 in in IN cord-276598-tm0yj2sn 653 16 the the DT cord-276598-tm0yj2sn 653 17 presence presence NN cord-276598-tm0yj2sn 653 18 of of IN cord-276598-tm0yj2sn 653 19 [ [ -LRB- cord-276598-tm0yj2sn 653 20 n n NNP cord-276598-tm0yj2sn 653 21 - - HYPH cord-276598-tm0yj2sn 653 22 Bu Bu NNP cord-276598-tm0yj2sn 653 23 4 4 CD cord-276598-tm0yj2sn 653 24 N]Br N]Br NNP cord-276598-tm0yj2sn 653 25 as as IN cord-276598-tm0yj2sn 653 26 the the DT cord-276598-tm0yj2sn 653 27 catalyst catalyst NN cord-276598-tm0yj2sn 653 28 , , , cord-276598-tm0yj2sn 653 29 where where WRB cord-276598-tm0yj2sn 653 30 it -PRON- PRP cord-276598-tm0yj2sn 653 31 is be VBZ cord-276598-tm0yj2sn 653 32 protonated protonate VBN cord-276598-tm0yj2sn 653 33 and and CC cord-276598-tm0yj2sn 653 34 reacts react VBZ cord-276598-tm0yj2sn 653 35 with with IN cord-276598-tm0yj2sn 653 36 CCl CCl NNS cord-276598-tm0yj2sn 653 37 4 4 CD cord-276598-tm0yj2sn 653 38 to to TO cord-276598-tm0yj2sn 653 39 form form VB cord-276598-tm0yj2sn 653 40 anionic anionic JJ cord-276598-tm0yj2sn 653 41 HCO HCO NNP cord-276598-tm0yj2sn 653 42 3 3 CD cord-276598-tm0yj2sn 653 43 ClH ClH NNP cord-276598-tm0yj2sn 653 44 − − NN cord-276598-tm0yj2sn 653 45 and and CC cord-276598-tm0yj2sn 653 46 cationic cationic JJ cord-276598-tm0yj2sn 653 47 Cl Cl NNP cord-276598-tm0yj2sn 653 48 3 3 CD cord-276598-tm0yj2sn 653 49 C C NNP cord-276598-tm0yj2sn 654 1 + + UH cord-276598-tm0yj2sn 654 2 . . . cord-276598-tm0yj2sn 655 1 The the DT cord-276598-tm0yj2sn 655 2 dialkyl dialkyl NN cord-276598-tm0yj2sn 655 3 H H NNP cord-276598-tm0yj2sn 655 4 - - HYPH cord-276598-tm0yj2sn 655 5 phosphonate phosphonate NNP cord-276598-tm0yj2sn 655 6 ( ( -LRB- cord-276598-tm0yj2sn 655 7 ( ( -LRB- cord-276598-tm0yj2sn 655 8 RO RO NNP cord-276598-tm0yj2sn 655 9 ) ) -RRB- cord-276598-tm0yj2sn 655 10 2 2 CD cord-276598-tm0yj2sn 656 1 P(O)H p(o)h NN cord-276598-tm0yj2sn 657 1 , , , cord-276598-tm0yj2sn 657 2 R r NN cord-276598-tm0yj2sn 657 3 = = NN cord-276598-tm0yj2sn 657 4 alkyl alkyl NN cord-276598-tm0yj2sn 657 5 ) ) -RRB- cord-276598-tm0yj2sn 657 6 is be VBZ cord-276598-tm0yj2sn 657 7 deprotonated deprotonate VBN cord-276598-tm0yj2sn 657 8 by by IN cord-276598-tm0yj2sn 657 9 the the DT cord-276598-tm0yj2sn 657 10 cationic cationic JJ cord-276598-tm0yj2sn 657 11 Cl Cl NNP cord-276598-tm0yj2sn 657 12 3 3 CD cord-276598-tm0yj2sn 657 13 C C NNP cord-276598-tm0yj2sn 657 14 + + CC cord-276598-tm0yj2sn 657 15 to to TO cord-276598-tm0yj2sn 657 16 yield yield VB cord-276598-tm0yj2sn 657 17 CHCl CHCl NNS cord-276598-tm0yj2sn 657 18 3 3 CD cord-276598-tm0yj2sn 657 19 and and CC cord-276598-tm0yj2sn 657 20 anionic anionic JJ cord-276598-tm0yj2sn 657 21 phosphate phosphate NN cord-276598-tm0yj2sn 657 22 , , , cord-276598-tm0yj2sn 657 23 ( ( -LRB- cord-276598-tm0yj2sn 657 24 RO ro NN cord-276598-tm0yj2sn 657 25 ) ) -RRB- cord-276598-tm0yj2sn 657 26 2 2 CD cord-276598-tm0yj2sn 657 27 P(O P(O NNP cord-276598-tm0yj2sn 657 28 ) ) -RRB- cord-276598-tm0yj2sn 657 29 − − NNS cord-276598-tm0yj2sn 657 30 . . . cord-276598-tm0yj2sn 658 1 Next next RB cord-276598-tm0yj2sn 658 2 , , , cord-276598-tm0yj2sn 658 3 the the DT cord-276598-tm0yj2sn 658 4 anionic anionic JJ cord-276598-tm0yj2sn 658 5 phosphate phosphate NN cord-276598-tm0yj2sn 658 6 reacts react VBZ cord-276598-tm0yj2sn 658 7 with with IN cord-276598-tm0yj2sn 658 8 HCO HCO NNP cord-276598-tm0yj2sn 658 9 3 3 CD cord-276598-tm0yj2sn 658 10 ClH clh NN cord-276598-tm0yj2sn 658 11 − − NNP cord-276598-tm0yj2sn 658 12 to to TO cord-276598-tm0yj2sn 658 13 form form VB cord-276598-tm0yj2sn 658 14 ( ( -LRB- cord-276598-tm0yj2sn 658 15 RO ro NN cord-276598-tm0yj2sn 658 16 ) ) -RRB- cord-276598-tm0yj2sn 658 17 2 2 CD cord-276598-tm0yj2sn 659 1 P(O)Cl P(O)Cl VBN cord-276598-tm0yj2sn 660 1 ( ( -LRB- cord-276598-tm0yj2sn 660 2 dACP dacp JJ cord-276598-tm0yj2sn 660 3 ; ; : cord-276598-tm0yj2sn 660 4 R r NN cord-276598-tm0yj2sn 660 5 = = NN cord-276598-tm0yj2sn 660 6 alkyl alkyl NN cord-276598-tm0yj2sn 660 7 ) ) -RRB- cord-276598-tm0yj2sn 660 8 and and CC cord-276598-tm0yj2sn 660 9 H H NNP cord-276598-tm0yj2sn 660 10 2 2 CD cord-276598-tm0yj2sn 660 11 CO CO NNP cord-276598-tm0yj2sn 660 12 3 3 CD cord-276598-tm0yj2sn 660 13 . . . cord-276598-tm0yj2sn 661 1 In in IN cord-276598-tm0yj2sn 661 2 the the DT cord-276598-tm0yj2sn 661 3 following follow VBG cord-276598-tm0yj2sn 661 4 step step NN cord-276598-tm0yj2sn 661 5 , , , cord-276598-tm0yj2sn 661 6 a a DT cord-276598-tm0yj2sn 661 7 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 661 8 substitution substitution NN cord-276598-tm0yj2sn 661 9 between between IN cord-276598-tm0yj2sn 661 10 the the DT cord-276598-tm0yj2sn 661 11 amine amine NN cord-276598-tm0yj2sn 661 12 and and CC cord-276598-tm0yj2sn 661 13 dACP dacp NN cord-276598-tm0yj2sn 661 14 results result NNS cord-276598-tm0yj2sn 661 15 in in IN cord-276598-tm0yj2sn 661 16 the the DT cord-276598-tm0yj2sn 661 17 formation formation NN cord-276598-tm0yj2sn 661 18 of of IN cord-276598-tm0yj2sn 661 19 the the DT cord-276598-tm0yj2sn 661 20 desired desire VBN cord-276598-tm0yj2sn 661 21 product product NN cord-276598-tm0yj2sn 661 22 . . . cord-276598-tm0yj2sn 662 1 Meanwhile meanwhile RB cord-276598-tm0yj2sn 662 2 , , , cord-276598-tm0yj2sn 662 3 K K NNP cord-276598-tm0yj2sn 662 4 2 2 CD cord-276598-tm0yj2sn 662 5 CO CO NNP cord-276598-tm0yj2sn 662 6 3 3 CD cord-276598-tm0yj2sn 662 7 serves serve VBZ cord-276598-tm0yj2sn 662 8 as as IN cord-276598-tm0yj2sn 662 9 the the DT cord-276598-tm0yj2sn 662 10 dehydrating dehydrate VBG cord-276598-tm0yj2sn 662 11 agent agent NN cord-276598-tm0yj2sn 662 12 in in IN cord-276598-tm0yj2sn 662 13 the the DT cord-276598-tm0yj2sn 662 14 reacting react VBG cord-276598-tm0yj2sn 662 15 system system NN cord-276598-tm0yj2sn 662 16 . . . cord-276598-tm0yj2sn 663 1 The the DT cord-276598-tm0yj2sn 663 2 plausible plausible JJ cord-276598-tm0yj2sn 663 3 mechanism mechanism NN cord-276598-tm0yj2sn 663 4 is be VBZ cord-276598-tm0yj2sn 663 5 also also RB cord-276598-tm0yj2sn 663 6 similar similar JJ cord-276598-tm0yj2sn 663 7 when when WRB cord-276598-tm0yj2sn 663 8 NaOH NaOH NNP cord-276598-tm0yj2sn 663 9 and and CC cord-276598-tm0yj2sn 663 10 The the DT cord-276598-tm0yj2sn 663 11 mechanistic mechanistic JJ cord-276598-tm0yj2sn 663 12 steps step NNS cord-276598-tm0yj2sn 663 13 for for IN cord-276598-tm0yj2sn 663 14 the the DT cord-276598-tm0yj2sn 663 15 synthesis synthesis NN cord-276598-tm0yj2sn 663 16 of of IN cord-276598-tm0yj2sn 663 17 P P NNP cord-276598-tm0yj2sn 663 18 - - HYPH cord-276598-tm0yj2sn 663 19 N N NNP cord-276598-tm0yj2sn 663 20 via via IN cord-276598-tm0yj2sn 663 21 a a DT cord-276598-tm0yj2sn 663 22 salt salt NN cord-276598-tm0yj2sn 663 23 elimination elimination NN cord-276598-tm0yj2sn 663 24 route route NN cord-276598-tm0yj2sn 663 25 were be VBD cord-276598-tm0yj2sn 663 26 not not RB cord-276598-tm0yj2sn 663 27 proposed propose VBN cord-276598-tm0yj2sn 663 28 by by IN cord-276598-tm0yj2sn 663 29 Zwierzak Zwierzak NNP cord-276598-tm0yj2sn 663 30 et et FW cord-276598-tm0yj2sn 663 31 al al NNP cord-276598-tm0yj2sn 663 32 . . . cord-276598-tm0yj2sn 664 1 [ [ -LRB- cord-276598-tm0yj2sn 664 2 89 89 CD cord-276598-tm0yj2sn 664 3 ] ] -RRB- cord-276598-tm0yj2sn 664 4 ; ; : cord-276598-tm0yj2sn 664 5 however however RB cord-276598-tm0yj2sn 664 6 , , , cord-276598-tm0yj2sn 664 7 based base VBN cord-276598-tm0yj2sn 664 8 on on IN cord-276598-tm0yj2sn 664 9 the the DT cord-276598-tm0yj2sn 664 10 roles role NNS cord-276598-tm0yj2sn 664 11 of of IN cord-276598-tm0yj2sn 664 12 KHCO3 KHCO3 NNP cord-276598-tm0yj2sn 664 13 , , , cord-276598-tm0yj2sn 664 14 K2CO3 K2CO3 NNP cord-276598-tm0yj2sn 664 15 , , , cord-276598-tm0yj2sn 664 16 and and CC cord-276598-tm0yj2sn 664 17 [ [ -LRB- cord-276598-tm0yj2sn 664 18 n n NN cord-276598-tm0yj2sn 664 19 - - HYPH cord-276598-tm0yj2sn 664 20 Bu4N]Br Bu4N]Br NNP cord-276598-tm0yj2sn 664 21 as as IN cord-276598-tm0yj2sn 664 22 outlined outline VBN cord-276598-tm0yj2sn 664 23 in in IN cord-276598-tm0yj2sn 664 24 the the DT cord-276598-tm0yj2sn 664 25 paper paper NN cord-276598-tm0yj2sn 664 26 and and CC cord-276598-tm0yj2sn 664 27 a a DT cord-276598-tm0yj2sn 664 28 recently recently RB cord-276598-tm0yj2sn 664 29 proposed propose VBN cord-276598-tm0yj2sn 664 30 mechanism mechanism NN cord-276598-tm0yj2sn 664 31 for for IN cord-276598-tm0yj2sn 664 32 an an DT cord-276598-tm0yj2sn 664 33 Atherton Atherton NNP cord-276598-tm0yj2sn 664 34 - - HYPH cord-276598-tm0yj2sn 664 35 Todd Todd NNP cord-276598-tm0yj2sn 664 36 type type NN cord-276598-tm0yj2sn 664 37 reaction reaction NN cord-276598-tm0yj2sn 664 38 , , , cord-276598-tm0yj2sn 664 39 a a DT cord-276598-tm0yj2sn 664 40 probable probable JJ cord-276598-tm0yj2sn 664 41 mechanism mechanism NN cord-276598-tm0yj2sn 664 42 can can MD cord-276598-tm0yj2sn 664 43 be be VB cord-276598-tm0yj2sn 664 44 postulated postulate VBN cord-276598-tm0yj2sn 664 45 ( ( -LRB- cord-276598-tm0yj2sn 664 46 Scheme scheme NN cord-276598-tm0yj2sn 664 47 21 21 CD cord-276598-tm0yj2sn 664 48 ) ) -RRB- cord-276598-tm0yj2sn 664 49 [ [ -LRB- cord-276598-tm0yj2sn 664 50 121 121 CD cord-276598-tm0yj2sn 664 51 ] ] -RRB- cord-276598-tm0yj2sn 664 52 . . . cord-276598-tm0yj2sn 665 1 In in IN cord-276598-tm0yj2sn 665 2 the the DT cord-276598-tm0yj2sn 665 3 reacting react VBG cord-276598-tm0yj2sn 665 4 system system NN cord-276598-tm0yj2sn 665 5 , , , cord-276598-tm0yj2sn 665 6 the the DT cord-276598-tm0yj2sn 665 7 HCO3 HCO3 NNP cord-276598-tm0yj2sn 665 8 − − NNP cord-276598-tm0yj2sn 665 9 migrates migrate VBZ cord-276598-tm0yj2sn 665 10 to to IN cord-276598-tm0yj2sn 665 11 the the DT cord-276598-tm0yj2sn 665 12 organic organic JJ cord-276598-tm0yj2sn 665 13 phase phase NN cord-276598-tm0yj2sn 665 14 in in IN cord-276598-tm0yj2sn 665 15 the the DT cord-276598-tm0yj2sn 665 16 presence presence NN cord-276598-tm0yj2sn 665 17 of of IN cord-276598-tm0yj2sn 665 18 [ [ -LRB- cord-276598-tm0yj2sn 665 19 n n NNP cord-276598-tm0yj2sn 665 20 - - HYPH cord-276598-tm0yj2sn 665 21 Bu4N]Br Bu4N]Br NNP cord-276598-tm0yj2sn 665 22 as as IN cord-276598-tm0yj2sn 665 23 the the DT cord-276598-tm0yj2sn 665 24 catalyst catalyst NN cord-276598-tm0yj2sn 665 25 , , , cord-276598-tm0yj2sn 665 26 where where WRB cord-276598-tm0yj2sn 665 27 it -PRON- PRP cord-276598-tm0yj2sn 665 28 is be VBZ cord-276598-tm0yj2sn 665 29 protonated protonate VBN cord-276598-tm0yj2sn 665 30 and and CC cord-276598-tm0yj2sn 665 31 reacts react VBZ cord-276598-tm0yj2sn 665 32 with with IN cord-276598-tm0yj2sn 665 33 CCl4 CCl4 NNP cord-276598-tm0yj2sn 665 34 to to TO cord-276598-tm0yj2sn 665 35 form form VB cord-276598-tm0yj2sn 665 36 anionic anionic JJ cord-276598-tm0yj2sn 665 37 HCO3ClH HCO3ClH NNP cord-276598-tm0yj2sn 665 38 − − NNP cord-276598-tm0yj2sn 665 39 and and CC cord-276598-tm0yj2sn 665 40 cationic cationic JJ cord-276598-tm0yj2sn 665 41 Cl3C Cl3C NNS cord-276598-tm0yj2sn 666 1 + + UH cord-276598-tm0yj2sn 666 2 . . . cord-276598-tm0yj2sn 667 1 The the DT cord-276598-tm0yj2sn 667 2 dialkyl dialkyl NN cord-276598-tm0yj2sn 667 3 H H NNP cord-276598-tm0yj2sn 667 4 - - HYPH cord-276598-tm0yj2sn 667 5 phosphonate phosphonate NNP cord-276598-tm0yj2sn 667 6 ( ( -LRB- cord-276598-tm0yj2sn 667 7 ( ( -LRB- cord-276598-tm0yj2sn 667 8 RO)2P(O)H RO)2P(O)H NNP cord-276598-tm0yj2sn 667 9 , , , cord-276598-tm0yj2sn 667 10 R r NN cord-276598-tm0yj2sn 667 11 = = NN cord-276598-tm0yj2sn 667 12 alkyl alkyl NN cord-276598-tm0yj2sn 667 13 ) ) -RRB- cord-276598-tm0yj2sn 667 14 is be VBZ cord-276598-tm0yj2sn 667 15 deprotonated deprotonate VBN cord-276598-tm0yj2sn 667 16 by by IN cord-276598-tm0yj2sn 667 17 the the DT cord-276598-tm0yj2sn 667 18 cationic cationic JJ cord-276598-tm0yj2sn 667 19 Cl3C Cl3C NNS cord-276598-tm0yj2sn 667 20 + + SYM cord-276598-tm0yj2sn 667 21 to to TO cord-276598-tm0yj2sn 667 22 yield yield VB cord-276598-tm0yj2sn 667 23 CHCl3 CHCl3 NNP cord-276598-tm0yj2sn 667 24 and and CC cord-276598-tm0yj2sn 667 25 anionic anionic JJ cord-276598-tm0yj2sn 667 26 phosphate phosphate NN cord-276598-tm0yj2sn 667 27 , , , cord-276598-tm0yj2sn 667 28 ( ( -LRB- cord-276598-tm0yj2sn 667 29 RO)2P(O ro)2p(o NN cord-276598-tm0yj2sn 667 30 ) ) -RRB- cord-276598-tm0yj2sn 667 31 − − NNS cord-276598-tm0yj2sn 667 32 . . . cord-276598-tm0yj2sn 668 1 Next next RB cord-276598-tm0yj2sn 668 2 , , , cord-276598-tm0yj2sn 668 3 the the DT cord-276598-tm0yj2sn 668 4 anionic anionic JJ cord-276598-tm0yj2sn 668 5 phosphate phosphate NN cord-276598-tm0yj2sn 668 6 reacts react VBZ cord-276598-tm0yj2sn 668 7 with with IN cord-276598-tm0yj2sn 668 8 HCO3ClH HCO3ClH NNP cord-276598-tm0yj2sn 668 9 − − NNP cord-276598-tm0yj2sn 668 10 to to TO cord-276598-tm0yj2sn 668 11 form form VB cord-276598-tm0yj2sn 669 1 ( ( -LRB- cord-276598-tm0yj2sn 669 2 RO)2P(O)Cl RO)2P(O)Cl NNP cord-276598-tm0yj2sn 669 3 ( ( -LRB- cord-276598-tm0yj2sn 669 4 dACP dacp NN cord-276598-tm0yj2sn 669 5 ; ; : cord-276598-tm0yj2sn 669 6 R r NN cord-276598-tm0yj2sn 669 7 = = NN cord-276598-tm0yj2sn 669 8 alkyl alkyl NN cord-276598-tm0yj2sn 669 9 ) ) -RRB- cord-276598-tm0yj2sn 669 10 and and CC cord-276598-tm0yj2sn 669 11 H2CO3 H2CO3 NNP cord-276598-tm0yj2sn 669 12 . . . cord-276598-tm0yj2sn 670 1 In in IN cord-276598-tm0yj2sn 670 2 the the DT cord-276598-tm0yj2sn 670 3 following follow VBG cord-276598-tm0yj2sn 670 4 step step NN cord-276598-tm0yj2sn 670 5 , , , cord-276598-tm0yj2sn 670 6 a a DT cord-276598-tm0yj2sn 670 7 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 670 8 substitution substitution NN cord-276598-tm0yj2sn 670 9 between between IN cord-276598-tm0yj2sn 670 10 the the DT cord-276598-tm0yj2sn 670 11 amine amine NN cord-276598-tm0yj2sn 670 12 and and CC cord-276598-tm0yj2sn 670 13 dACP dacp NN cord-276598-tm0yj2sn 670 14 results result NNS cord-276598-tm0yj2sn 670 15 in in IN cord-276598-tm0yj2sn 670 16 the the DT cord-276598-tm0yj2sn 670 17 formation formation NN cord-276598-tm0yj2sn 670 18 of of IN cord-276598-tm0yj2sn 670 19 the the DT cord-276598-tm0yj2sn 670 20 desired desire VBN cord-276598-tm0yj2sn 670 21 product product NN cord-276598-tm0yj2sn 670 22 . . . cord-276598-tm0yj2sn 671 1 Meanwhile meanwhile RB cord-276598-tm0yj2sn 671 2 , , , cord-276598-tm0yj2sn 671 3 K2CO3 K2CO3 NNP cord-276598-tm0yj2sn 671 4 serves serve VBZ cord-276598-tm0yj2sn 671 5 as as IN cord-276598-tm0yj2sn 671 6 the the DT cord-276598-tm0yj2sn 671 7 dehydrating dehydrate VBG cord-276598-tm0yj2sn 671 8 agent agent NN cord-276598-tm0yj2sn 671 9 in in IN cord-276598-tm0yj2sn 671 10 the the DT cord-276598-tm0yj2sn 671 11 reacting react VBG cord-276598-tm0yj2sn 671 12 system system NN cord-276598-tm0yj2sn 671 13 . . . cord-276598-tm0yj2sn 672 1 The the DT cord-276598-tm0yj2sn 672 2 plausible plausible JJ cord-276598-tm0yj2sn 672 3 mechanism mechanism NN cord-276598-tm0yj2sn 672 4 is be VBZ cord-276598-tm0yj2sn 672 5 also also RB cord-276598-tm0yj2sn 672 6 similar similar JJ cord-276598-tm0yj2sn 672 7 when when WRB cord-276598-tm0yj2sn 672 8 NaOH NaOH NNP cord-276598-tm0yj2sn 672 9 and and CC cord-276598-tm0yj2sn 672 10 [ [ -LRB- cord-276598-tm0yj2sn 672 11 BnEt3N]Cl BnEt3N]Cl NNP cord-276598-tm0yj2sn 672 12 are be VBP cord-276598-tm0yj2sn 672 13 used use VBN cord-276598-tm0yj2sn 672 14 in in IN cord-276598-tm0yj2sn 672 15 place place NN cord-276598-tm0yj2sn 672 16 of of IN cord-276598-tm0yj2sn 672 17 KHCO3 KHCO3 NNP cord-276598-tm0yj2sn 672 18 and and CC cord-276598-tm0yj2sn 672 19 [ [ -LRB- cord-276598-tm0yj2sn 672 20 n n NNP cord-276598-tm0yj2sn 672 21 - - HYPH cord-276598-tm0yj2sn 672 22 Bu4N]Br Bu4N]Br NNP cord-276598-tm0yj2sn 672 23 , , , cord-276598-tm0yj2sn 672 24 respectively respectively RB cord-276598-tm0yj2sn 672 25 . . . cord-276598-tm0yj2sn 673 1 Scheme scheme NN cord-276598-tm0yj2sn 673 2 21 21 CD cord-276598-tm0yj2sn 673 3 . . . cord-276598-tm0yj2sn 674 1 Potential potential JJ cord-276598-tm0yj2sn 674 2 mechanism mechanism NN cord-276598-tm0yj2sn 674 3 for for IN cord-276598-tm0yj2sn 674 4 the the DT cord-276598-tm0yj2sn 674 5 formation formation NN cord-276598-tm0yj2sn 674 6 of of IN cord-276598-tm0yj2sn 674 7 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 674 8 using use VBG cord-276598-tm0yj2sn 674 9 a a DT cord-276598-tm0yj2sn 674 10 salt salt NN cord-276598-tm0yj2sn 674 11 elimination elimination NN cord-276598-tm0yj2sn 674 12 route route NN cord-276598-tm0yj2sn 674 13 . . . cord-276598-tm0yj2sn 675 1 [ [ -LRB- cord-276598-tm0yj2sn 675 2 96 96 CD cord-276598-tm0yj2sn 675 3 ] ] -RRB- cord-276598-tm0yj2sn 675 4 . . . cord-276598-tm0yj2sn 676 1 Then then RB cord-276598-tm0yj2sn 676 2 , , , cord-276598-tm0yj2sn 676 3 the the DT cord-276598-tm0yj2sn 676 4 dACP dacp NN cord-276598-tm0yj2sn 676 5 reacts react VBZ cord-276598-tm0yj2sn 676 6 with with IN cord-276598-tm0yj2sn 676 7 N n CD cord-276598-tm0yj2sn 676 8 - - HYPH cord-276598-tm0yj2sn 676 9 phenylformamide phenylformamide NN cord-276598-tm0yj2sn 676 10 or or CC cord-276598-tm0yj2sn 676 11 the the DT cord-276598-tm0yj2sn 676 12 2-chloro 2-chloro CD cord-276598-tm0yj2sn 676 13 - - HYPH cord-276598-tm0yj2sn 676 14 N n CD cord-276598-tm0yj2sn 676 15 - - HYPH cord-276598-tm0yj2sn 676 16 phenylacetamide phenylacetamide NN cord-276598-tm0yj2sn 676 17 derivative derivative NN cord-276598-tm0yj2sn 676 18 to to TO cord-276598-tm0yj2sn 676 19 form form VB cord-276598-tm0yj2sn 676 20 the the DT cord-276598-tm0yj2sn 676 21 product product NN cord-276598-tm0yj2sn 676 22 . . . cord-276598-tm0yj2sn 677 1 Alternatively alternatively RB cord-276598-tm0yj2sn 677 2 , , , cord-276598-tm0yj2sn 677 3 the the DT cord-276598-tm0yj2sn 677 4 mechanism mechanism NN cord-276598-tm0yj2sn 677 5 could could MD cord-276598-tm0yj2sn 677 6 proceed proceed VB cord-276598-tm0yj2sn 677 7 via via IN cord-276598-tm0yj2sn 677 8 a a DT cord-276598-tm0yj2sn 677 9 dialkyl dialkyl NN cord-276598-tm0yj2sn 677 10 ( ( -LRB- cord-276598-tm0yj2sn 677 11 acetyl)(phenyl)phosphoramidate acetyl)(phenyl)phosphoramidate NNP cord-276598-tm0yj2sn 677 12 intermediate intermediate JJ cord-276598-tm0yj2sn 677 13 , , , cord-276598-tm0yj2sn 677 14 which which WDT cord-276598-tm0yj2sn 677 15 subsequently subsequently RB cord-276598-tm0yj2sn 677 16 undergoes undergo VBZ cord-276598-tm0yj2sn 677 17 hydrolysis hydrolysis NN cord-276598-tm0yj2sn 677 18 to to TO cord-276598-tm0yj2sn 677 19 afford afford VB cord-276598-tm0yj2sn 677 20 the the DT cord-276598-tm0yj2sn 677 21 product product NN cord-276598-tm0yj2sn 677 22 . . . cord-276598-tm0yj2sn 678 1 The the DT cord-276598-tm0yj2sn 678 2 mechanisms mechanism NNS cord-276598-tm0yj2sn 678 3 of of IN cord-276598-tm0yj2sn 678 4 P P NNP cord-276598-tm0yj2sn 678 5 - - HYPH cord-276598-tm0yj2sn 678 6 N n CD cord-276598-tm0yj2sn 678 7 formation formation NN cord-276598-tm0yj2sn 678 8 from from IN cord-276598-tm0yj2sn 678 9 Gupta Gupta NNP cord-276598-tm0yj2sn 678 10 et et NNP cord-276598-tm0yj2sn 678 11 al al NNP cord-276598-tm0yj2sn 678 12 . . . cord-276598-tm0yj2sn 679 1 [ [ -LRB- cord-276598-tm0yj2sn 679 2 97 97 CD cord-276598-tm0yj2sn 679 3 ] ] -RRB- cord-276598-tm0yj2sn 679 4 and and CC cord-276598-tm0yj2sn 679 5 Kaboudin Kaboudin NNP cord-276598-tm0yj2sn 679 6 et et NNP cord-276598-tm0yj2sn 679 7 al al NNP cord-276598-tm0yj2sn 679 8 . . . cord-276598-tm0yj2sn 680 1 [ [ -LRB- cord-276598-tm0yj2sn 680 2 98 98 CD cord-276598-tm0yj2sn 680 3 ] ] -RRB- cord-276598-tm0yj2sn 680 4 suggest suggest VBP cord-276598-tm0yj2sn 680 5 that that IN cord-276598-tm0yj2sn 680 6 the the DT cord-276598-tm0yj2sn 680 7 dialkyl dialkyl NN cord-276598-tm0yj2sn 680 8 H H NNP cord-276598-tm0yj2sn 680 9 - - HYPH cord-276598-tm0yj2sn 680 10 phosphonate phosphonate NNP cord-276598-tm0yj2sn 680 11 ( ( -LRB- cord-276598-tm0yj2sn 680 12 ( ( -LRB- cord-276598-tm0yj2sn 680 13 RO RO NNP cord-276598-tm0yj2sn 680 14 ) ) -RRB- cord-276598-tm0yj2sn 680 15 2 2 CD cord-276598-tm0yj2sn 681 1 P(O)H p(o)h NN cord-276598-tm0yj2sn 682 1 , , , cord-276598-tm0yj2sn 682 2 R r NN cord-276598-tm0yj2sn 682 3 = = NN cord-276598-tm0yj2sn 682 4 alkyl alkyl NN cord-276598-tm0yj2sn 682 5 ) ) -RRB- cord-276598-tm0yj2sn 682 6 reacts react VBZ cord-276598-tm0yj2sn 682 7 with with IN cord-276598-tm0yj2sn 682 8 trichloroisocyanuric trichloroisocyanuric NN cord-276598-tm0yj2sn 682 9 acid acid NN cord-276598-tm0yj2sn 682 10 ( ( -LRB- cord-276598-tm0yj2sn 682 11 tCiC tCiC NNP cord-276598-tm0yj2sn 682 12 - - HYPH cord-276598-tm0yj2sn 682 13 A a NN cord-276598-tm0yj2sn 682 14 ) ) -RRB- cord-276598-tm0yj2sn 682 15 to to TO cord-276598-tm0yj2sn 682 16 form form VB cord-276598-tm0yj2sn 682 17 the the DT cord-276598-tm0yj2sn 682 18 intermediate intermediate JJ cord-276598-tm0yj2sn 682 19 ( ( -LRB- cord-276598-tm0yj2sn 682 20 RO RO NNP cord-276598-tm0yj2sn 682 21 ) ) -RRB- cord-276598-tm0yj2sn 682 22 2 2 CD cord-276598-tm0yj2sn 683 1 P(O)Cl P(O)Cl VBN cord-276598-tm0yj2sn 684 1 ( ( -LRB- cord-276598-tm0yj2sn 684 2 dACP dacp JJ cord-276598-tm0yj2sn 684 3 ; ; : cord-276598-tm0yj2sn 684 4 R r NN cord-276598-tm0yj2sn 684 5 = = NN cord-276598-tm0yj2sn 684 6 alkyl alkyl NN cord-276598-tm0yj2sn 684 7 ) ) -RRB- cord-276598-tm0yj2sn 684 8 and and CC cord-276598-tm0yj2sn 684 9 1,3,5-triazinane-2,4,6-trione 1,3,5-triazinane-2,4,6-trione CD cord-276598-tm0yj2sn 684 10 ( ( -LRB- cord-276598-tm0yj2sn 684 11 tAtO tato NN cord-276598-tm0yj2sn 684 12 ) ) -RRB- cord-276598-tm0yj2sn 685 1 ( ( -LRB- cord-276598-tm0yj2sn 685 2 Scheme scheme NN cord-276598-tm0yj2sn 685 3 22 22 CD cord-276598-tm0yj2sn 685 4 ) ) -RRB- cord-276598-tm0yj2sn 685 5 . . . cord-276598-tm0yj2sn 686 1 Following follow VBG cord-276598-tm0yj2sn 686 2 , , , cord-276598-tm0yj2sn 686 3 a a DT cord-276598-tm0yj2sn 686 4 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 686 5 substitution substitution NN cord-276598-tm0yj2sn 686 6 between between IN cord-276598-tm0yj2sn 686 7 the the DT cord-276598-tm0yj2sn 686 8 dACP dacp NN cord-276598-tm0yj2sn 686 9 and and CC cord-276598-tm0yj2sn 686 10 the the DT cord-276598-tm0yj2sn 686 11 amine amine NN cord-276598-tm0yj2sn 686 12 result result NN cord-276598-tm0yj2sn 686 13 in in IN cord-276598-tm0yj2sn 686 14 the the DT cord-276598-tm0yj2sn 686 15 P P NNP cord-276598-tm0yj2sn 686 16 - - HYPH cord-276598-tm0yj2sn 686 17 N N NNP cord-276598-tm0yj2sn 686 18 with with IN cord-276598-tm0yj2sn 686 19 HCl HCl NNP cord-276598-tm0yj2sn 686 20 as as IN cord-276598-tm0yj2sn 686 21 the the DT cord-276598-tm0yj2sn 686 22 major major JJ cord-276598-tm0yj2sn 686 23 by by IN cord-276598-tm0yj2sn 686 24 - - HYPH cord-276598-tm0yj2sn 686 25 product product NN cord-276598-tm0yj2sn 686 26 . . . cord-276598-tm0yj2sn 687 1 The the DT cord-276598-tm0yj2sn 687 2 mechanisms mechanism NNS cord-276598-tm0yj2sn 687 3 of of IN cord-276598-tm0yj2sn 687 4 P P NNP cord-276598-tm0yj2sn 687 5 - - HYPH cord-276598-tm0yj2sn 687 6 N n CD cord-276598-tm0yj2sn 687 7 formation formation NN cord-276598-tm0yj2sn 687 8 from from IN cord-276598-tm0yj2sn 687 9 Gupta Gupta NNP cord-276598-tm0yj2sn 687 10 et et NNP cord-276598-tm0yj2sn 687 11 al al NNP cord-276598-tm0yj2sn 687 12 . . . cord-276598-tm0yj2sn 688 1 [ [ -LRB- cord-276598-tm0yj2sn 688 2 97 97 CD cord-276598-tm0yj2sn 688 3 ] ] -RRB- cord-276598-tm0yj2sn 688 4 and and CC cord-276598-tm0yj2sn 688 5 Kaboudin Kaboudin NNP cord-276598-tm0yj2sn 688 6 et et NNP cord-276598-tm0yj2sn 688 7 al al NNP cord-276598-tm0yj2sn 688 8 . . . cord-276598-tm0yj2sn 689 1 [ [ -LRB- cord-276598-tm0yj2sn 689 2 98 98 CD cord-276598-tm0yj2sn 689 3 ] ] -RRB- cord-276598-tm0yj2sn 689 4 suggest suggest VBP cord-276598-tm0yj2sn 689 5 that that IN cord-276598-tm0yj2sn 689 6 the the DT cord-276598-tm0yj2sn 689 7 dialkyl dialkyl NN cord-276598-tm0yj2sn 689 8 H H NNP cord-276598-tm0yj2sn 689 9 - - HYPH cord-276598-tm0yj2sn 689 10 phosphonate phosphonate NNP cord-276598-tm0yj2sn 689 11 ( ( -LRB- cord-276598-tm0yj2sn 689 12 ( ( -LRB- cord-276598-tm0yj2sn 689 13 RO)2P(O)H RO)2P(O)H NNP cord-276598-tm0yj2sn 689 14 , , , cord-276598-tm0yj2sn 689 15 R r NN cord-276598-tm0yj2sn 689 16 = = NN cord-276598-tm0yj2sn 689 17 alkyl alkyl NN cord-276598-tm0yj2sn 689 18 ) ) -RRB- cord-276598-tm0yj2sn 689 19 reacts react VBZ cord-276598-tm0yj2sn 689 20 with with IN cord-276598-tm0yj2sn 689 21 trichloroisocyanuric trichloroisocyanuric NN cord-276598-tm0yj2sn 689 22 acid acid NN cord-276598-tm0yj2sn 689 23 ( ( -LRB- cord-276598-tm0yj2sn 689 24 tCiC tCiC NNP cord-276598-tm0yj2sn 689 25 - - HYPH cord-276598-tm0yj2sn 689 26 A a NN cord-276598-tm0yj2sn 689 27 ) ) -RRB- cord-276598-tm0yj2sn 689 28 to to TO cord-276598-tm0yj2sn 689 29 form form VB cord-276598-tm0yj2sn 689 30 the the DT cord-276598-tm0yj2sn 689 31 intermediate intermediate JJ cord-276598-tm0yj2sn 689 32 ( ( -LRB- cord-276598-tm0yj2sn 689 33 RO)2P(O)Cl RO)2P(O)Cl NNP cord-276598-tm0yj2sn 689 34 ( ( -LRB- cord-276598-tm0yj2sn 689 35 dACP dacp NN cord-276598-tm0yj2sn 689 36 ; ; : cord-276598-tm0yj2sn 689 37 R r NN cord-276598-tm0yj2sn 689 38 = = NN cord-276598-tm0yj2sn 689 39 alkyl alkyl NN cord-276598-tm0yj2sn 689 40 ) ) -RRB- cord-276598-tm0yj2sn 689 41 and and CC cord-276598-tm0yj2sn 689 42 1,3,5-triazinane-2,4,6-trione 1,3,5-triazinane-2,4,6-trione CD cord-276598-tm0yj2sn 689 43 ( ( -LRB- cord-276598-tm0yj2sn 689 44 tAtO tato NN cord-276598-tm0yj2sn 689 45 ) ) -RRB- cord-276598-tm0yj2sn 690 1 ( ( -LRB- cord-276598-tm0yj2sn 690 2 Scheme scheme NN cord-276598-tm0yj2sn 690 3 22 22 CD cord-276598-tm0yj2sn 690 4 ) ) -RRB- cord-276598-tm0yj2sn 690 5 . . . cord-276598-tm0yj2sn 691 1 Following follow VBG cord-276598-tm0yj2sn 691 2 , , , cord-276598-tm0yj2sn 691 3 a a DT cord-276598-tm0yj2sn 691 4 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 691 5 substitution substitution NN cord-276598-tm0yj2sn 691 6 between between IN cord-276598-tm0yj2sn 691 7 the the DT cord-276598-tm0yj2sn 691 8 dACP dacp NN cord-276598-tm0yj2sn 691 9 and and CC cord-276598-tm0yj2sn 691 10 the the DT cord-276598-tm0yj2sn 691 11 amine amine NN cord-276598-tm0yj2sn 691 12 result result NN cord-276598-tm0yj2sn 691 13 in in IN cord-276598-tm0yj2sn 691 14 the the DT cord-276598-tm0yj2sn 691 15 P P NNP cord-276598-tm0yj2sn 691 16 - - HYPH cord-276598-tm0yj2sn 691 17 N N NNP cord-276598-tm0yj2sn 691 18 with with IN cord-276598-tm0yj2sn 691 19 HCl HCl NNP cord-276598-tm0yj2sn 691 20 as as IN cord-276598-tm0yj2sn 691 21 the the DT cord-276598-tm0yj2sn 691 22 major major JJ cord-276598-tm0yj2sn 691 23 by by IN cord-276598-tm0yj2sn 691 24 - - HYPH cord-276598-tm0yj2sn 691 25 product product NN cord-276598-tm0yj2sn 691 26 . . . cord-276598-tm0yj2sn 692 1 Proposed propose VBN cord-276598-tm0yj2sn 692 2 mechanism mechanism NN cord-276598-tm0yj2sn 692 3 for for IN cord-276598-tm0yj2sn 692 4 the the DT cord-276598-tm0yj2sn 692 5 base base NN cord-276598-tm0yj2sn 692 6 - - HYPH cord-276598-tm0yj2sn 692 7 free free JJ cord-276598-tm0yj2sn 692 8 synthesis synthesis NN cord-276598-tm0yj2sn 692 9 of of IN cord-276598-tm0yj2sn 692 10 phosphoramidates phosphoramidate NNS cord-276598-tm0yj2sn 692 11 using use VBG cord-276598-tm0yj2sn 692 12 a a DT cord-276598-tm0yj2sn 692 13 chlorinating chlorinate VBG cord-276598-tm0yj2sn 692 14 agent agent NN cord-276598-tm0yj2sn 692 15 . . . cord-276598-tm0yj2sn 693 1 The the DT cord-276598-tm0yj2sn 693 2 mechanism mechanism NN cord-276598-tm0yj2sn 693 3 of of IN cord-276598-tm0yj2sn 693 4 the the DT cord-276598-tm0yj2sn 693 5 reaction reaction NN cord-276598-tm0yj2sn 693 6 by by IN cord-276598-tm0yj2sn 693 7 Jang Jang NNP cord-276598-tm0yj2sn 693 8 et et FW cord-276598-tm0yj2sn 693 9 al al NNP cord-276598-tm0yj2sn 693 10 . . NNP cord-276598-tm0yj2sn 693 11 suggests suggest VBZ cord-276598-tm0yj2sn 693 12 that that IN cord-276598-tm0yj2sn 693 13 diphenyl diphenyl NNP cord-276598-tm0yj2sn 693 14 phosphoric phosphoric JJ cord-276598-tm0yj2sn 693 15 acid acid NN cord-276598-tm0yj2sn 693 16 ( ( -LRB- cord-276598-tm0yj2sn 693 17 dPPA dppa NN cord-276598-tm0yj2sn 693 18 ) ) -RRB- cord-276598-tm0yj2sn 693 19 undergoes undergo VBZ cord-276598-tm0yj2sn 693 20 chlorination chlorination NN cord-276598-tm0yj2sn 693 21 in in IN cord-276598-tm0yj2sn 693 22 the the DT cord-276598-tm0yj2sn 693 23 presence presence NN cord-276598-tm0yj2sn 693 24 of of IN cord-276598-tm0yj2sn 693 25 a a DT cord-276598-tm0yj2sn 693 26 base base NN cord-276598-tm0yj2sn 693 27 , , , cord-276598-tm0yj2sn 693 28 which which WDT cord-276598-tm0yj2sn 693 29 is be VBZ cord-276598-tm0yj2sn 693 30 subsequently subsequently RB cord-276598-tm0yj2sn 693 31 attacked attack VBN cord-276598-tm0yj2sn 693 32 by by IN cord-276598-tm0yj2sn 693 33 the the DT cord-276598-tm0yj2sn 693 34 amine amine NN cord-276598-tm0yj2sn 693 35 to to TO cord-276598-tm0yj2sn 693 36 afford afford VB cord-276598-tm0yj2sn 693 37 the the DT cord-276598-tm0yj2sn 693 38 P P NNP cord-276598-tm0yj2sn 693 39 - - HYPH cord-276598-tm0yj2sn 693 40 N n CD cord-276598-tm0yj2sn 693 41 product product NN cord-276598-tm0yj2sn 693 42 [ [ -LRB- cord-276598-tm0yj2sn 693 43 99 99 CD cord-276598-tm0yj2sn 693 44 ] ] -RRB- cord-276598-tm0yj2sn 693 45 . . . cord-276598-tm0yj2sn 694 1 Although although IN cord-276598-tm0yj2sn 694 2 the the DT cord-276598-tm0yj2sn 694 3 authors author NNS cord-276598-tm0yj2sn 694 4 did do VBD cord-276598-tm0yj2sn 694 5 not not RB cord-276598-tm0yj2sn 694 6 propose propose VB cord-276598-tm0yj2sn 694 7 any any DT cord-276598-tm0yj2sn 694 8 mechanism mechanism NN cord-276598-tm0yj2sn 694 9 , , , cord-276598-tm0yj2sn 694 10 they -PRON- PRP cord-276598-tm0yj2sn 694 11 suggested suggest VBD cord-276598-tm0yj2sn 694 12 that that IN cord-276598-tm0yj2sn 694 13 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 694 14 attack attack NN cord-276598-tm0yj2sn 694 15 on on IN cord-276598-tm0yj2sn 694 16 the the DT cord-276598-tm0yj2sn 694 17 P p NN cord-276598-tm0yj2sn 694 18 atom atom NN cord-276598-tm0yj2sn 694 19 was be VBD cord-276598-tm0yj2sn 694 20 consistent consistent JJ cord-276598-tm0yj2sn 694 21 with with IN cord-276598-tm0yj2sn 694 22 aliphatic aliphatic JJ cord-276598-tm0yj2sn 694 23 amines amine NNS cord-276598-tm0yj2sn 694 24 resulting result VBG cord-276598-tm0yj2sn 694 25 in in IN cord-276598-tm0yj2sn 694 26 a a DT cord-276598-tm0yj2sn 694 27 higher high JJR cord-276598-tm0yj2sn 694 28 yield yield NN cord-276598-tm0yj2sn 694 29 of of IN cord-276598-tm0yj2sn 694 30 products product NNS cord-276598-tm0yj2sn 694 31 than than IN cord-276598-tm0yj2sn 694 32 the the DT cord-276598-tm0yj2sn 694 33 aromatic aromatic JJ cord-276598-tm0yj2sn 694 34 amines amine NNS cord-276598-tm0yj2sn 694 35 because because IN cord-276598-tm0yj2sn 694 36 aliphatic aliphatic JJ cord-276598-tm0yj2sn 694 37 amines amine NNS cord-276598-tm0yj2sn 694 38 are be VBP cord-276598-tm0yj2sn 694 39 more more RBR cord-276598-tm0yj2sn 694 40 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 694 41 . . . cord-276598-tm0yj2sn 695 1 The the DT cord-276598-tm0yj2sn 695 2 mechanistic mechanistic JJ cord-276598-tm0yj2sn 695 3 step step NN cord-276598-tm0yj2sn 695 4 suggested suggest VBN cord-276598-tm0yj2sn 695 5 by by IN cord-276598-tm0yj2sn 695 6 Appel Appel NNP cord-276598-tm0yj2sn 695 7 and and CC cord-276598-tm0yj2sn 695 8 Einig Einig NNP cord-276598-tm0yj2sn 695 9 involves involve VBZ cord-276598-tm0yj2sn 695 10 the the DT cord-276598-tm0yj2sn 695 11 formation formation NN cord-276598-tm0yj2sn 695 12 of of IN cord-276598-tm0yj2sn 695 13 oxo oxo NN cord-276598-tm0yj2sn 695 14 - - HYPH cord-276598-tm0yj2sn 695 15 triphenyl triphenyl NN cord-276598-tm0yj2sn 695 16 - - HYPH cord-276598-tm0yj2sn 695 17 diphosphoxanium diphosphoxanium NN cord-276598-tm0yj2sn 695 18 salt salt NN cord-276598-tm0yj2sn 695 19 intermediate intermediate JJ cord-276598-tm0yj2sn 695 20 from from IN cord-276598-tm0yj2sn 695 21 a a DT cord-276598-tm0yj2sn 695 22 deprotonation deprotonation NN cord-276598-tm0yj2sn 695 23 of of IN cord-276598-tm0yj2sn 695 24 phosphoric phosphoric JJ cord-276598-tm0yj2sn 695 25 acid acid NN cord-276598-tm0yj2sn 695 26 by by IN cord-276598-tm0yj2sn 695 27 CCl4 ccl4 NN cord-276598-tm0yj2sn 695 28 in in IN cord-276598-tm0yj2sn 695 29 the the DT cord-276598-tm0yj2sn 695 30 presence presence NN cord-276598-tm0yj2sn 695 31 of of IN cord-276598-tm0yj2sn 695 32 phosphine phosphine NN cord-276598-tm0yj2sn 695 33 ( ( -LRB- cord-276598-tm0yj2sn 695 34 Scheme scheme NN cord-276598-tm0yj2sn 695 35 23 23 CD cord-276598-tm0yj2sn 695 36 ) ) -RRB- cord-276598-tm0yj2sn 695 37 [ [ -LRB- cord-276598-tm0yj2sn 695 38 86 86 CD cord-276598-tm0yj2sn 695 39 ] ] -RRB- cord-276598-tm0yj2sn 695 40 . . . cord-276598-tm0yj2sn 696 1 Nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 696 2 substitution substitution NN cord-276598-tm0yj2sn 696 3 from from IN cord-276598-tm0yj2sn 696 4 amine amine NN cord-276598-tm0yj2sn 696 5 results result NNS cord-276598-tm0yj2sn 696 6 in in IN cord-276598-tm0yj2sn 696 7 the the DT cord-276598-tm0yj2sn 696 8 desired desire VBN cord-276598-tm0yj2sn 696 9 product product NN cord-276598-tm0yj2sn 696 10 and and CC cord-276598-tm0yj2sn 696 11 triphenylphosphate triphenylphosphate NN cord-276598-tm0yj2sn 696 12 as as IN cord-276598-tm0yj2sn 696 13 the the DT cord-276598-tm0yj2sn 696 14 by by IN cord-276598-tm0yj2sn 696 15 - - HYPH cord-276598-tm0yj2sn 696 16 product product NN cord-276598-tm0yj2sn 696 17 . . . cord-276598-tm0yj2sn 697 1 Scheme scheme NN cord-276598-tm0yj2sn 697 2 23 23 CD cord-276598-tm0yj2sn 697 3 . . . cord-276598-tm0yj2sn 698 1 Proposed propose VBN cord-276598-tm0yj2sn 698 2 mechanism mechanism NN cord-276598-tm0yj2sn 698 3 for for IN cord-276598-tm0yj2sn 698 4 the the DT cord-276598-tm0yj2sn 698 5 synthesis synthesis NN cord-276598-tm0yj2sn 698 6 of of IN cord-276598-tm0yj2sn 698 7 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 698 8 from from IN cord-276598-tm0yj2sn 698 9 phosphoric phosphoric JJ cord-276598-tm0yj2sn 698 10 acid acid NN cord-276598-tm0yj2sn 698 11 and and CC cord-276598-tm0yj2sn 698 12 amine amine NN cord-276598-tm0yj2sn 698 13 in in IN cord-276598-tm0yj2sn 698 14 the the DT cord-276598-tm0yj2sn 698 15 presence presence NN cord-276598-tm0yj2sn 698 16 of of IN cord-276598-tm0yj2sn 698 17 phosphine phosphine NN cord-276598-tm0yj2sn 698 18 and and CC cord-276598-tm0yj2sn 698 19 CCl4 ccl4 NN cord-276598-tm0yj2sn 698 20 . . . cord-276598-tm0yj2sn 699 1 In in IN cord-276598-tm0yj2sn 699 2 the the DT cord-276598-tm0yj2sn 699 3 suggested suggest VBN cord-276598-tm0yj2sn 699 4 reaction reaction NN cord-276598-tm0yj2sn 699 5 mechanism mechanism NN cord-276598-tm0yj2sn 699 6 by by IN cord-276598-tm0yj2sn 699 7 [ [ -LRB- cord-276598-tm0yj2sn 699 8 100 100 CD cord-276598-tm0yj2sn 699 9 ] ] -RRB- cord-276598-tm0yj2sn 699 10 , , , cord-276598-tm0yj2sn 699 11 iodine iodine NN cord-276598-tm0yj2sn 699 12 reacts react VBZ cord-276598-tm0yj2sn 699 13 with with IN cord-276598-tm0yj2sn 699 14 ( ( -LRB- cord-276598-tm0yj2sn 699 15 RO)3P RO)3P NNP cord-276598-tm0yj2sn 699 16 ( ( -LRB- cord-276598-tm0yj2sn 699 17 R r NN cord-276598-tm0yj2sn 699 18 = = NN cord-276598-tm0yj2sn 699 19 alkyl alkyl NN cord-276598-tm0yj2sn 699 20 ) ) -RRB- cord-276598-tm0yj2sn 699 21 to to TO cord-276598-tm0yj2sn 699 22 form form VB cord-276598-tm0yj2sn 699 23 trialkoxyiodophosphonium trialkoxyiodophosphonium NN cord-276598-tm0yj2sn 699 24 intermediate intermediate JJ cord-276598-tm0yj2sn 699 25 , , , cord-276598-tm0yj2sn 699 26 which which WDT cord-276598-tm0yj2sn 699 27 is be VBZ cord-276598-tm0yj2sn 699 28 further further RB cord-276598-tm0yj2sn 699 29 attacked attack VBN cord-276598-tm0yj2sn 699 30 by by IN cord-276598-tm0yj2sn 699 31 iodide iodide NN cord-276598-tm0yj2sn 699 32 ion ion NN cord-276598-tm0yj2sn 699 33 to to TO cord-276598-tm0yj2sn 699 34 form form VB cord-276598-tm0yj2sn 699 35 dialkyl dialkyl FW cord-276598-tm0yj2sn 699 36 phosphoriodidate phosphoriodidate NNP cord-276598-tm0yj2sn 699 37 ( ( -LRB- cord-276598-tm0yj2sn 699 38 dAPPI dappi NN cord-276598-tm0yj2sn 699 39 ) ) -RRB- cord-276598-tm0yj2sn 700 1 ( ( -LRB- cord-276598-tm0yj2sn 700 2 Arbuzov Arbuzov NNP cord-276598-tm0yj2sn 700 3 reaction reaction NN cord-276598-tm0yj2sn 700 4 , , , cord-276598-tm0yj2sn 700 5 Scheme scheme NN cord-276598-tm0yj2sn 700 6 24 24 CD cord-276598-tm0yj2sn 700 7 ) ) -RRB- cord-276598-tm0yj2sn 700 8 . . . cord-276598-tm0yj2sn 701 1 Then then RB cord-276598-tm0yj2sn 701 2 , , , cord-276598-tm0yj2sn 701 3 the the DT cord-276598-tm0yj2sn 701 4 dAPPI dappi NN cord-276598-tm0yj2sn 701 5 is be VBZ cord-276598-tm0yj2sn 701 6 attacked attack VBN cord-276598-tm0yj2sn 701 7 by by IN cord-276598-tm0yj2sn 701 8 the the DT cord-276598-tm0yj2sn 701 9 amine amine NN cord-276598-tm0yj2sn 701 10 to to TO cord-276598-tm0yj2sn 701 11 give give VB cord-276598-tm0yj2sn 701 12 the the DT cord-276598-tm0yj2sn 701 13 desired desire VBN cord-276598-tm0yj2sn 701 14 P P NNP cord-276598-tm0yj2sn 701 15 - - HYPH cord-276598-tm0yj2sn 701 16 N N NNP cord-276598-tm0yj2sn 701 17 with with IN cord-276598-tm0yj2sn 701 18 an an DT cord-276598-tm0yj2sn 701 19 elimination elimination NN cord-276598-tm0yj2sn 701 20 of of IN cord-276598-tm0yj2sn 701 21 HI HI NNP cord-276598-tm0yj2sn 701 22 . . . cord-276598-tm0yj2sn 702 1 N N NNP cord-276598-tm0yj2sn 702 2 - - HYPH cord-276598-tm0yj2sn 702 3 phosphoryl phosphoryl NN cord-276598-tm0yj2sn 702 4 amino amino NN cord-276598-tm0yj2sn 702 5 acid acid NN cord-276598-tm0yj2sn 702 6 esters ester NNS cord-276598-tm0yj2sn 702 7 and and CC cord-276598-tm0yj2sn 702 8 P P NNP cord-276598-tm0yj2sn 702 9 - - HYPH cord-276598-tm0yj2sn 702 10 N N NNP cord-276598-tm0yj2sn 702 11 with with IN cord-276598-tm0yj2sn 702 12 a a DT cord-276598-tm0yj2sn 702 13 free free JJ cord-276598-tm0yj2sn 702 14 amino amino NN cord-276598-tm0yj2sn 702 15 group group NN cord-276598-tm0yj2sn 702 16 were be VBD cord-276598-tm0yj2sn 702 17 also also RB cord-276598-tm0yj2sn 702 18 synthesized synthesize VBN cord-276598-tm0yj2sn 702 19 using use VBG cord-276598-tm0yj2sn 702 20 the the DT cord-276598-tm0yj2sn 702 21 iodine iodine NN cord-276598-tm0yj2sn 702 22 - - HYPH cord-276598-tm0yj2sn 702 23 mediated mediate VBN cord-276598-tm0yj2sn 702 24 synthesis synthesis NN cord-276598-tm0yj2sn 702 25 method method NN cord-276598-tm0yj2sn 702 26 . . . cord-276598-tm0yj2sn 703 1 The the DT cord-276598-tm0yj2sn 703 2 challenges challenge NNS cord-276598-tm0yj2sn 703 3 with with IN cord-276598-tm0yj2sn 703 4 this this DT cord-276598-tm0yj2sn 703 5 iodine iodine NN cord-276598-tm0yj2sn 703 6 - - HYPH cord-276598-tm0yj2sn 703 7 mediated mediate VBN cord-276598-tm0yj2sn 703 8 P p NN cord-276598-tm0yj2sn 703 9 - - HYPH cord-276598-tm0yj2sn 703 10 N n CD cord-276598-tm0yj2sn 703 11 formation formation NN cord-276598-tm0yj2sn 703 12 is be VBZ cord-276598-tm0yj2sn 703 13 that that IN cord-276598-tm0yj2sn 703 14 many many JJ cord-276598-tm0yj2sn 703 15 side side NN cord-276598-tm0yj2sn 703 16 products product NNS cord-276598-tm0yj2sn 703 17 are be VBP cord-276598-tm0yj2sn 703 18 formed form VBN cord-276598-tm0yj2sn 703 19 , , , cord-276598-tm0yj2sn 703 20 and and CC cord-276598-tm0yj2sn 703 21 the the DT cord-276598-tm0yj2sn 703 22 Proposed propose VBN cord-276598-tm0yj2sn 703 23 mechanism mechanism NN cord-276598-tm0yj2sn 703 24 for for IN cord-276598-tm0yj2sn 703 25 the the DT cord-276598-tm0yj2sn 703 26 base base NN cord-276598-tm0yj2sn 703 27 - - HYPH cord-276598-tm0yj2sn 703 28 free free JJ cord-276598-tm0yj2sn 703 29 synthesis synthesis NN cord-276598-tm0yj2sn 703 30 of of IN cord-276598-tm0yj2sn 703 31 phosphoramidates phosphoramidate NNS cord-276598-tm0yj2sn 703 32 using use VBG cord-276598-tm0yj2sn 703 33 a a DT cord-276598-tm0yj2sn 703 34 chlorinating chlorinate VBG cord-276598-tm0yj2sn 703 35 agent agent NN cord-276598-tm0yj2sn 703 36 . . . cord-276598-tm0yj2sn 704 1 The the DT cord-276598-tm0yj2sn 704 2 mechanism mechanism NN cord-276598-tm0yj2sn 704 3 of of IN cord-276598-tm0yj2sn 704 4 the the DT cord-276598-tm0yj2sn 704 5 reaction reaction NN cord-276598-tm0yj2sn 704 6 by by IN cord-276598-tm0yj2sn 704 7 Jang Jang NNP cord-276598-tm0yj2sn 704 8 et et FW cord-276598-tm0yj2sn 704 9 al al NNP cord-276598-tm0yj2sn 704 10 . . NNP cord-276598-tm0yj2sn 704 11 suggests suggest VBZ cord-276598-tm0yj2sn 704 12 that that IN cord-276598-tm0yj2sn 704 13 diphenyl diphenyl NNP cord-276598-tm0yj2sn 704 14 phosphoric phosphoric JJ cord-276598-tm0yj2sn 704 15 acid acid NN cord-276598-tm0yj2sn 704 16 ( ( -LRB- cord-276598-tm0yj2sn 704 17 dPPA dppa NN cord-276598-tm0yj2sn 704 18 ) ) -RRB- cord-276598-tm0yj2sn 704 19 undergoes undergo VBZ cord-276598-tm0yj2sn 704 20 chlorination chlorination NN cord-276598-tm0yj2sn 704 21 in in IN cord-276598-tm0yj2sn 704 22 the the DT cord-276598-tm0yj2sn 704 23 presence presence NN cord-276598-tm0yj2sn 704 24 of of IN cord-276598-tm0yj2sn 704 25 a a DT cord-276598-tm0yj2sn 704 26 base base NN cord-276598-tm0yj2sn 704 27 , , , cord-276598-tm0yj2sn 704 28 which which WDT cord-276598-tm0yj2sn 704 29 is be VBZ cord-276598-tm0yj2sn 704 30 subsequently subsequently RB cord-276598-tm0yj2sn 704 31 attacked attack VBN cord-276598-tm0yj2sn 704 32 by by IN cord-276598-tm0yj2sn 704 33 the the DT cord-276598-tm0yj2sn 704 34 amine amine NN cord-276598-tm0yj2sn 704 35 to to TO cord-276598-tm0yj2sn 704 36 afford afford VB cord-276598-tm0yj2sn 704 37 the the DT cord-276598-tm0yj2sn 704 38 P P NNP cord-276598-tm0yj2sn 704 39 - - HYPH cord-276598-tm0yj2sn 704 40 N n CD cord-276598-tm0yj2sn 704 41 product product NN cord-276598-tm0yj2sn 704 42 [ [ -LRB- cord-276598-tm0yj2sn 704 43 99 99 CD cord-276598-tm0yj2sn 704 44 ] ] -RRB- cord-276598-tm0yj2sn 704 45 . . . cord-276598-tm0yj2sn 705 1 Although although IN cord-276598-tm0yj2sn 705 2 the the DT cord-276598-tm0yj2sn 705 3 authors author NNS cord-276598-tm0yj2sn 705 4 did do VBD cord-276598-tm0yj2sn 705 5 not not RB cord-276598-tm0yj2sn 705 6 propose propose VB cord-276598-tm0yj2sn 705 7 any any DT cord-276598-tm0yj2sn 705 8 mechanism mechanism NN cord-276598-tm0yj2sn 705 9 , , , cord-276598-tm0yj2sn 705 10 they -PRON- PRP cord-276598-tm0yj2sn 705 11 suggested suggest VBD cord-276598-tm0yj2sn 705 12 that that IN cord-276598-tm0yj2sn 705 13 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 705 14 attack attack NN cord-276598-tm0yj2sn 705 15 on on IN cord-276598-tm0yj2sn 705 16 the the DT cord-276598-tm0yj2sn 705 17 P p NN cord-276598-tm0yj2sn 705 18 atom atom NN cord-276598-tm0yj2sn 705 19 was be VBD cord-276598-tm0yj2sn 705 20 consistent consistent JJ cord-276598-tm0yj2sn 705 21 with with IN cord-276598-tm0yj2sn 705 22 aliphatic aliphatic JJ cord-276598-tm0yj2sn 705 23 amines amine NNS cord-276598-tm0yj2sn 705 24 resulting result VBG cord-276598-tm0yj2sn 705 25 in in IN cord-276598-tm0yj2sn 705 26 a a DT cord-276598-tm0yj2sn 705 27 higher high JJR cord-276598-tm0yj2sn 705 28 yield yield NN cord-276598-tm0yj2sn 705 29 of of IN cord-276598-tm0yj2sn 705 30 products product NNS cord-276598-tm0yj2sn 705 31 than than IN cord-276598-tm0yj2sn 705 32 the the DT cord-276598-tm0yj2sn 705 33 aromatic aromatic JJ cord-276598-tm0yj2sn 705 34 amines amine NNS cord-276598-tm0yj2sn 705 35 because because IN cord-276598-tm0yj2sn 705 36 aliphatic aliphatic JJ cord-276598-tm0yj2sn 705 37 amines amine NNS cord-276598-tm0yj2sn 705 38 are be VBP cord-276598-tm0yj2sn 705 39 more more RBR cord-276598-tm0yj2sn 705 40 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 705 41 . . . cord-276598-tm0yj2sn 706 1 The the DT cord-276598-tm0yj2sn 706 2 mechanistic mechanistic JJ cord-276598-tm0yj2sn 706 3 step step NN cord-276598-tm0yj2sn 706 4 suggested suggest VBN cord-276598-tm0yj2sn 706 5 by by IN cord-276598-tm0yj2sn 706 6 Appel Appel NNP cord-276598-tm0yj2sn 706 7 and and CC cord-276598-tm0yj2sn 706 8 Einig Einig NNP cord-276598-tm0yj2sn 706 9 involves involve VBZ cord-276598-tm0yj2sn 706 10 the the DT cord-276598-tm0yj2sn 706 11 formation formation NN cord-276598-tm0yj2sn 706 12 of of IN cord-276598-tm0yj2sn 706 13 oxo oxo NN cord-276598-tm0yj2sn 706 14 - - HYPH cord-276598-tm0yj2sn 706 15 triphenyl triphenyl NN cord-276598-tm0yj2sn 706 16 - - HYPH cord-276598-tm0yj2sn 706 17 diphosphoxanium diphosphoxanium NN cord-276598-tm0yj2sn 706 18 salt salt NN cord-276598-tm0yj2sn 706 19 intermediate intermediate JJ cord-276598-tm0yj2sn 706 20 from from IN cord-276598-tm0yj2sn 706 21 a a DT cord-276598-tm0yj2sn 706 22 deprotonation deprotonation NN cord-276598-tm0yj2sn 706 23 of of IN cord-276598-tm0yj2sn 706 24 phosphoric phosphoric JJ cord-276598-tm0yj2sn 706 25 acid acid NN cord-276598-tm0yj2sn 706 26 by by IN cord-276598-tm0yj2sn 706 27 CCl CCl NNS cord-276598-tm0yj2sn 706 28 4 4 CD cord-276598-tm0yj2sn 706 29 in in IN cord-276598-tm0yj2sn 706 30 the the DT cord-276598-tm0yj2sn 706 31 presence presence NN cord-276598-tm0yj2sn 706 32 of of IN cord-276598-tm0yj2sn 706 33 phosphine phosphine NN cord-276598-tm0yj2sn 706 34 ( ( -LRB- cord-276598-tm0yj2sn 706 35 Scheme scheme NN cord-276598-tm0yj2sn 706 36 23 23 CD cord-276598-tm0yj2sn 706 37 ) ) -RRB- cord-276598-tm0yj2sn 706 38 [ [ -LRB- cord-276598-tm0yj2sn 706 39 86 86 CD cord-276598-tm0yj2sn 706 40 ] ] -RRB- cord-276598-tm0yj2sn 706 41 . . . cord-276598-tm0yj2sn 707 1 Nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 707 2 substitution substitution NN cord-276598-tm0yj2sn 707 3 from from IN cord-276598-tm0yj2sn 707 4 amine amine NN cord-276598-tm0yj2sn 707 5 results result NNS cord-276598-tm0yj2sn 707 6 in in IN cord-276598-tm0yj2sn 707 7 the the DT cord-276598-tm0yj2sn 707 8 desired desire VBN cord-276598-tm0yj2sn 707 9 product product NN cord-276598-tm0yj2sn 707 10 and and CC cord-276598-tm0yj2sn 707 11 triphenylphosphate triphenylphosphate NN cord-276598-tm0yj2sn 707 12 as as IN cord-276598-tm0yj2sn 707 13 the the DT cord-276598-tm0yj2sn 707 14 by by IN cord-276598-tm0yj2sn 707 15 - - HYPH cord-276598-tm0yj2sn 707 16 product product NN cord-276598-tm0yj2sn 707 17 . . . cord-276598-tm0yj2sn 708 1 The the DT cord-276598-tm0yj2sn 708 2 mechanisms mechanism NNS cord-276598-tm0yj2sn 708 3 of of IN cord-276598-tm0yj2sn 708 4 P P NNP cord-276598-tm0yj2sn 708 5 - - HYPH cord-276598-tm0yj2sn 708 6 N n CD cord-276598-tm0yj2sn 708 7 formation formation NN cord-276598-tm0yj2sn 708 8 from from IN cord-276598-tm0yj2sn 708 9 Gupta Gupta NNP cord-276598-tm0yj2sn 708 10 et et NNP cord-276598-tm0yj2sn 708 11 al al NNP cord-276598-tm0yj2sn 708 12 . . . cord-276598-tm0yj2sn 709 1 [ [ -LRB- cord-276598-tm0yj2sn 709 2 97 97 CD cord-276598-tm0yj2sn 709 3 ] ] -RRB- cord-276598-tm0yj2sn 709 4 and and CC cord-276598-tm0yj2sn 709 5 Kaboudin Kaboudin NNP cord-276598-tm0yj2sn 709 6 et et NNP cord-276598-tm0yj2sn 709 7 al al NNP cord-276598-tm0yj2sn 709 8 . . . cord-276598-tm0yj2sn 710 1 [ [ -LRB- cord-276598-tm0yj2sn 710 2 98 98 CD cord-276598-tm0yj2sn 710 3 ] ] -RRB- cord-276598-tm0yj2sn 710 4 suggest suggest VBP cord-276598-tm0yj2sn 710 5 that that IN cord-276598-tm0yj2sn 710 6 the the DT cord-276598-tm0yj2sn 710 7 dialkyl dialkyl NN cord-276598-tm0yj2sn 710 8 H H NNP cord-276598-tm0yj2sn 710 9 - - HYPH cord-276598-tm0yj2sn 710 10 phosphonate phosphonate NNP cord-276598-tm0yj2sn 710 11 ( ( -LRB- cord-276598-tm0yj2sn 710 12 ( ( -LRB- cord-276598-tm0yj2sn 710 13 RO)2P(O)H RO)2P(O)H NNP cord-276598-tm0yj2sn 710 14 , , , cord-276598-tm0yj2sn 710 15 R r NN cord-276598-tm0yj2sn 710 16 = = NN cord-276598-tm0yj2sn 710 17 alkyl alkyl NN cord-276598-tm0yj2sn 710 18 ) ) -RRB- cord-276598-tm0yj2sn 710 19 reacts react VBZ cord-276598-tm0yj2sn 710 20 with with IN cord-276598-tm0yj2sn 710 21 trichloroisocyanuric trichloroisocyanuric NN cord-276598-tm0yj2sn 710 22 acid acid NN cord-276598-tm0yj2sn 710 23 ( ( -LRB- cord-276598-tm0yj2sn 710 24 tCiC tCiC NNP cord-276598-tm0yj2sn 710 25 - - HYPH cord-276598-tm0yj2sn 710 26 A a NN cord-276598-tm0yj2sn 710 27 ) ) -RRB- cord-276598-tm0yj2sn 710 28 to to TO cord-276598-tm0yj2sn 710 29 form form VB cord-276598-tm0yj2sn 710 30 the the DT cord-276598-tm0yj2sn 710 31 intermediate intermediate JJ cord-276598-tm0yj2sn 710 32 ( ( -LRB- cord-276598-tm0yj2sn 710 33 RO)2P(O)Cl RO)2P(O)Cl NNP cord-276598-tm0yj2sn 710 34 ( ( -LRB- cord-276598-tm0yj2sn 710 35 dACP dacp NN cord-276598-tm0yj2sn 710 36 ; ; : cord-276598-tm0yj2sn 710 37 R r NN cord-276598-tm0yj2sn 710 38 = = NN cord-276598-tm0yj2sn 710 39 alkyl alkyl NN cord-276598-tm0yj2sn 710 40 ) ) -RRB- cord-276598-tm0yj2sn 710 41 and and CC cord-276598-tm0yj2sn 710 42 1,3,5-triazinane-2,4,6-trione 1,3,5-triazinane-2,4,6-trione CD cord-276598-tm0yj2sn 710 43 ( ( -LRB- cord-276598-tm0yj2sn 710 44 tAtO tato NN cord-276598-tm0yj2sn 710 45 ) ) -RRB- cord-276598-tm0yj2sn 711 1 ( ( -LRB- cord-276598-tm0yj2sn 711 2 Scheme scheme NN cord-276598-tm0yj2sn 711 3 22 22 CD cord-276598-tm0yj2sn 711 4 ) ) -RRB- cord-276598-tm0yj2sn 711 5 . . . cord-276598-tm0yj2sn 712 1 Following follow VBG cord-276598-tm0yj2sn 712 2 , , , cord-276598-tm0yj2sn 712 3 a a DT cord-276598-tm0yj2sn 712 4 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 712 5 substitution substitution NN cord-276598-tm0yj2sn 712 6 between between IN cord-276598-tm0yj2sn 712 7 the the DT cord-276598-tm0yj2sn 712 8 dACP dacp NN cord-276598-tm0yj2sn 712 9 and and CC cord-276598-tm0yj2sn 712 10 the the DT cord-276598-tm0yj2sn 712 11 amine amine NN cord-276598-tm0yj2sn 712 12 result result NN cord-276598-tm0yj2sn 712 13 in in IN cord-276598-tm0yj2sn 712 14 the the DT cord-276598-tm0yj2sn 712 15 P P NNP cord-276598-tm0yj2sn 712 16 - - HYPH cord-276598-tm0yj2sn 712 17 N N NNP cord-276598-tm0yj2sn 712 18 with with IN cord-276598-tm0yj2sn 712 19 HCl HCl NNP cord-276598-tm0yj2sn 712 20 as as IN cord-276598-tm0yj2sn 712 21 the the DT cord-276598-tm0yj2sn 712 22 major major JJ cord-276598-tm0yj2sn 712 23 by by IN cord-276598-tm0yj2sn 712 24 - - HYPH cord-276598-tm0yj2sn 712 25 product product NN cord-276598-tm0yj2sn 712 26 . . . cord-276598-tm0yj2sn 713 1 Proposed propose VBN cord-276598-tm0yj2sn 713 2 mechanism mechanism NN cord-276598-tm0yj2sn 713 3 for for IN cord-276598-tm0yj2sn 713 4 the the DT cord-276598-tm0yj2sn 713 5 base base NN cord-276598-tm0yj2sn 713 6 - - HYPH cord-276598-tm0yj2sn 713 7 free free JJ cord-276598-tm0yj2sn 713 8 synthesis synthesis NN cord-276598-tm0yj2sn 713 9 of of IN cord-276598-tm0yj2sn 713 10 phosphoramidates phosphoramidate NNS cord-276598-tm0yj2sn 713 11 using use VBG cord-276598-tm0yj2sn 713 12 a a DT cord-276598-tm0yj2sn 713 13 chlorinating chlorinate VBG cord-276598-tm0yj2sn 713 14 agent agent NN cord-276598-tm0yj2sn 713 15 . . . cord-276598-tm0yj2sn 714 1 The the DT cord-276598-tm0yj2sn 714 2 mechanism mechanism NN cord-276598-tm0yj2sn 714 3 of of IN cord-276598-tm0yj2sn 714 4 the the DT cord-276598-tm0yj2sn 714 5 reaction reaction NN cord-276598-tm0yj2sn 714 6 by by IN cord-276598-tm0yj2sn 714 7 Jang Jang NNP cord-276598-tm0yj2sn 714 8 et et FW cord-276598-tm0yj2sn 714 9 al al NNP cord-276598-tm0yj2sn 714 10 . . NNP cord-276598-tm0yj2sn 714 11 suggests suggest VBZ cord-276598-tm0yj2sn 714 12 that that IN cord-276598-tm0yj2sn 714 13 diphenyl diphenyl NNP cord-276598-tm0yj2sn 714 14 phosphoric phosphoric JJ cord-276598-tm0yj2sn 714 15 acid acid NN cord-276598-tm0yj2sn 714 16 ( ( -LRB- cord-276598-tm0yj2sn 714 17 dPPA dppa NN cord-276598-tm0yj2sn 714 18 ) ) -RRB- cord-276598-tm0yj2sn 714 19 undergoes undergo VBZ cord-276598-tm0yj2sn 714 20 chlorination chlorination NN cord-276598-tm0yj2sn 714 21 in in IN cord-276598-tm0yj2sn 714 22 the the DT cord-276598-tm0yj2sn 714 23 presence presence NN cord-276598-tm0yj2sn 714 24 of of IN cord-276598-tm0yj2sn 714 25 a a DT cord-276598-tm0yj2sn 714 26 base base NN cord-276598-tm0yj2sn 714 27 , , , cord-276598-tm0yj2sn 714 28 which which WDT cord-276598-tm0yj2sn 714 29 is be VBZ cord-276598-tm0yj2sn 714 30 subsequently subsequently RB cord-276598-tm0yj2sn 714 31 attacked attack VBN cord-276598-tm0yj2sn 714 32 by by IN cord-276598-tm0yj2sn 714 33 the the DT cord-276598-tm0yj2sn 714 34 amine amine NN cord-276598-tm0yj2sn 714 35 to to TO cord-276598-tm0yj2sn 714 36 afford afford VB cord-276598-tm0yj2sn 714 37 the the DT cord-276598-tm0yj2sn 714 38 P P NNP cord-276598-tm0yj2sn 714 39 - - HYPH cord-276598-tm0yj2sn 714 40 N n CD cord-276598-tm0yj2sn 714 41 product product NN cord-276598-tm0yj2sn 714 42 [ [ -LRB- cord-276598-tm0yj2sn 714 43 99 99 CD cord-276598-tm0yj2sn 714 44 ] ] -RRB- cord-276598-tm0yj2sn 714 45 . . . cord-276598-tm0yj2sn 715 1 Although although IN cord-276598-tm0yj2sn 715 2 the the DT cord-276598-tm0yj2sn 715 3 authors author NNS cord-276598-tm0yj2sn 715 4 did do VBD cord-276598-tm0yj2sn 715 5 not not RB cord-276598-tm0yj2sn 715 6 propose propose VB cord-276598-tm0yj2sn 715 7 any any DT cord-276598-tm0yj2sn 715 8 mechanism mechanism NN cord-276598-tm0yj2sn 715 9 , , , cord-276598-tm0yj2sn 715 10 they -PRON- PRP cord-276598-tm0yj2sn 715 11 suggested suggest VBD cord-276598-tm0yj2sn 715 12 that that IN cord-276598-tm0yj2sn 715 13 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 715 14 attack attack NN cord-276598-tm0yj2sn 715 15 on on IN cord-276598-tm0yj2sn 715 16 the the DT cord-276598-tm0yj2sn 715 17 P p NN cord-276598-tm0yj2sn 715 18 atom atom NN cord-276598-tm0yj2sn 715 19 was be VBD cord-276598-tm0yj2sn 715 20 consistent consistent JJ cord-276598-tm0yj2sn 715 21 with with IN cord-276598-tm0yj2sn 715 22 aliphatic aliphatic JJ cord-276598-tm0yj2sn 715 23 amines amine NNS cord-276598-tm0yj2sn 715 24 resulting result VBG cord-276598-tm0yj2sn 715 25 in in IN cord-276598-tm0yj2sn 715 26 a a DT cord-276598-tm0yj2sn 715 27 higher high JJR cord-276598-tm0yj2sn 715 28 yield yield NN cord-276598-tm0yj2sn 715 29 of of IN cord-276598-tm0yj2sn 715 30 products product NNS cord-276598-tm0yj2sn 715 31 than than IN cord-276598-tm0yj2sn 715 32 the the DT cord-276598-tm0yj2sn 715 33 aromatic aromatic JJ cord-276598-tm0yj2sn 715 34 amines amine NNS cord-276598-tm0yj2sn 715 35 because because IN cord-276598-tm0yj2sn 715 36 aliphatic aliphatic JJ cord-276598-tm0yj2sn 715 37 amines amine NNS cord-276598-tm0yj2sn 715 38 are be VBP cord-276598-tm0yj2sn 715 39 more more RBR cord-276598-tm0yj2sn 715 40 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 715 41 . . . cord-276598-tm0yj2sn 716 1 The the DT cord-276598-tm0yj2sn 716 2 mechanistic mechanistic JJ cord-276598-tm0yj2sn 716 3 step step NN cord-276598-tm0yj2sn 716 4 suggested suggest VBN cord-276598-tm0yj2sn 716 5 by by IN cord-276598-tm0yj2sn 716 6 Appel Appel NNP cord-276598-tm0yj2sn 716 7 and and CC cord-276598-tm0yj2sn 716 8 Einig Einig NNP cord-276598-tm0yj2sn 716 9 involves involve VBZ cord-276598-tm0yj2sn 716 10 the the DT cord-276598-tm0yj2sn 716 11 formation formation NN cord-276598-tm0yj2sn 716 12 of of IN cord-276598-tm0yj2sn 716 13 oxo oxo NN cord-276598-tm0yj2sn 716 14 - - HYPH cord-276598-tm0yj2sn 716 15 triphenyl triphenyl NN cord-276598-tm0yj2sn 716 16 - - HYPH cord-276598-tm0yj2sn 716 17 diphosphoxanium diphosphoxanium NN cord-276598-tm0yj2sn 716 18 salt salt NN cord-276598-tm0yj2sn 716 19 intermediate intermediate JJ cord-276598-tm0yj2sn 716 20 from from IN cord-276598-tm0yj2sn 716 21 a a DT cord-276598-tm0yj2sn 716 22 deprotonation deprotonation NN cord-276598-tm0yj2sn 716 23 of of IN cord-276598-tm0yj2sn 716 24 phosphoric phosphoric JJ cord-276598-tm0yj2sn 716 25 acid acid NN cord-276598-tm0yj2sn 716 26 by by IN cord-276598-tm0yj2sn 716 27 CCl4 ccl4 NN cord-276598-tm0yj2sn 716 28 in in IN cord-276598-tm0yj2sn 716 29 the the DT cord-276598-tm0yj2sn 716 30 presence presence NN cord-276598-tm0yj2sn 716 31 of of IN cord-276598-tm0yj2sn 716 32 phosphine phosphine NN cord-276598-tm0yj2sn 716 33 ( ( -LRB- cord-276598-tm0yj2sn 716 34 Scheme scheme NN cord-276598-tm0yj2sn 716 35 23 23 CD cord-276598-tm0yj2sn 716 36 ) ) -RRB- cord-276598-tm0yj2sn 716 37 [ [ -LRB- cord-276598-tm0yj2sn 716 38 86 86 CD cord-276598-tm0yj2sn 716 39 ] ] -RRB- cord-276598-tm0yj2sn 716 40 . . . cord-276598-tm0yj2sn 717 1 Nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 717 2 substitution substitution NN cord-276598-tm0yj2sn 717 3 from from IN cord-276598-tm0yj2sn 717 4 amine amine NN cord-276598-tm0yj2sn 717 5 results result NNS cord-276598-tm0yj2sn 717 6 in in IN cord-276598-tm0yj2sn 717 7 the the DT cord-276598-tm0yj2sn 717 8 desired desire VBN cord-276598-tm0yj2sn 717 9 product product NN cord-276598-tm0yj2sn 717 10 and and CC cord-276598-tm0yj2sn 717 11 triphenylphosphate triphenylphosphate NN cord-276598-tm0yj2sn 717 12 as as IN cord-276598-tm0yj2sn 717 13 the the DT cord-276598-tm0yj2sn 717 14 by by IN cord-276598-tm0yj2sn 717 15 - - HYPH cord-276598-tm0yj2sn 717 16 product product NN cord-276598-tm0yj2sn 717 17 . . . cord-276598-tm0yj2sn 718 1 Scheme scheme NN cord-276598-tm0yj2sn 718 2 23 23 CD cord-276598-tm0yj2sn 718 3 . . . cord-276598-tm0yj2sn 719 1 Proposed propose VBN cord-276598-tm0yj2sn 719 2 mechanism mechanism NN cord-276598-tm0yj2sn 719 3 for for IN cord-276598-tm0yj2sn 719 4 the the DT cord-276598-tm0yj2sn 719 5 synthesis synthesis NN cord-276598-tm0yj2sn 719 6 of of IN cord-276598-tm0yj2sn 719 7 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 719 8 from from IN cord-276598-tm0yj2sn 719 9 phosphoric phosphoric JJ cord-276598-tm0yj2sn 719 10 acid acid NN cord-276598-tm0yj2sn 719 11 and and CC cord-276598-tm0yj2sn 719 12 amine amine NN cord-276598-tm0yj2sn 719 13 in in IN cord-276598-tm0yj2sn 719 14 the the DT cord-276598-tm0yj2sn 719 15 presence presence NN cord-276598-tm0yj2sn 719 16 of of IN cord-276598-tm0yj2sn 719 17 phosphine phosphine NN cord-276598-tm0yj2sn 719 18 and and CC cord-276598-tm0yj2sn 719 19 CCl4 ccl4 NN cord-276598-tm0yj2sn 719 20 . . . cord-276598-tm0yj2sn 720 1 In in IN cord-276598-tm0yj2sn 720 2 the the DT cord-276598-tm0yj2sn 720 3 suggested suggest VBN cord-276598-tm0yj2sn 720 4 reaction reaction NN cord-276598-tm0yj2sn 720 5 mechanism mechanism NN cord-276598-tm0yj2sn 720 6 by by IN cord-276598-tm0yj2sn 720 7 [ [ -LRB- cord-276598-tm0yj2sn 720 8 100 100 CD cord-276598-tm0yj2sn 720 9 ] ] -RRB- cord-276598-tm0yj2sn 720 10 , , , cord-276598-tm0yj2sn 720 11 iodine iodine NN cord-276598-tm0yj2sn 720 12 reacts react VBZ cord-276598-tm0yj2sn 720 13 with with IN cord-276598-tm0yj2sn 720 14 ( ( -LRB- cord-276598-tm0yj2sn 720 15 RO)3P RO)3P NNP cord-276598-tm0yj2sn 720 16 ( ( -LRB- cord-276598-tm0yj2sn 720 17 R r NN cord-276598-tm0yj2sn 720 18 = = NN cord-276598-tm0yj2sn 720 19 alkyl alkyl NN cord-276598-tm0yj2sn 720 20 ) ) -RRB- cord-276598-tm0yj2sn 720 21 to to TO cord-276598-tm0yj2sn 720 22 form form VB cord-276598-tm0yj2sn 720 23 trialkoxyiodophosphonium trialkoxyiodophosphonium NN cord-276598-tm0yj2sn 720 24 intermediate intermediate JJ cord-276598-tm0yj2sn 720 25 , , , cord-276598-tm0yj2sn 720 26 which which WDT cord-276598-tm0yj2sn 720 27 is be VBZ cord-276598-tm0yj2sn 720 28 further further RB cord-276598-tm0yj2sn 720 29 attacked attack VBN cord-276598-tm0yj2sn 720 30 by by IN cord-276598-tm0yj2sn 720 31 iodide iodide NN cord-276598-tm0yj2sn 720 32 ion ion NN cord-276598-tm0yj2sn 720 33 to to TO cord-276598-tm0yj2sn 720 34 form form VB cord-276598-tm0yj2sn 720 35 dialkyl dialkyl FW cord-276598-tm0yj2sn 720 36 phosphoriodidate phosphoriodidate NNP cord-276598-tm0yj2sn 720 37 ( ( -LRB- cord-276598-tm0yj2sn 720 38 dAPPI dappi NN cord-276598-tm0yj2sn 720 39 ) ) -RRB- cord-276598-tm0yj2sn 721 1 ( ( -LRB- cord-276598-tm0yj2sn 721 2 Arbuzov Arbuzov NNP cord-276598-tm0yj2sn 721 3 reaction reaction NN cord-276598-tm0yj2sn 721 4 , , , cord-276598-tm0yj2sn 721 5 Scheme scheme NN cord-276598-tm0yj2sn 721 6 24 24 CD cord-276598-tm0yj2sn 721 7 ) ) -RRB- cord-276598-tm0yj2sn 721 8 . . . cord-276598-tm0yj2sn 722 1 Then then RB cord-276598-tm0yj2sn 722 2 , , , cord-276598-tm0yj2sn 722 3 the the DT cord-276598-tm0yj2sn 722 4 dAPPI dappi NN cord-276598-tm0yj2sn 722 5 is be VBZ cord-276598-tm0yj2sn 722 6 attacked attack VBN cord-276598-tm0yj2sn 722 7 by by IN cord-276598-tm0yj2sn 722 8 the the DT cord-276598-tm0yj2sn 722 9 amine amine NN cord-276598-tm0yj2sn 722 10 to to TO cord-276598-tm0yj2sn 722 11 give give VB cord-276598-tm0yj2sn 722 12 the the DT cord-276598-tm0yj2sn 722 13 desired desire VBN cord-276598-tm0yj2sn 722 14 P P NNP cord-276598-tm0yj2sn 722 15 - - HYPH cord-276598-tm0yj2sn 722 16 N N NNP cord-276598-tm0yj2sn 722 17 with with IN cord-276598-tm0yj2sn 722 18 an an DT cord-276598-tm0yj2sn 722 19 elimination elimination NN cord-276598-tm0yj2sn 722 20 of of IN cord-276598-tm0yj2sn 722 21 HI HI NNP cord-276598-tm0yj2sn 722 22 . . . cord-276598-tm0yj2sn 723 1 N N NNP cord-276598-tm0yj2sn 723 2 - - HYPH cord-276598-tm0yj2sn 723 3 phosphoryl phosphoryl NN cord-276598-tm0yj2sn 723 4 amino amino NN cord-276598-tm0yj2sn 723 5 acid acid NN cord-276598-tm0yj2sn 723 6 esters ester NNS cord-276598-tm0yj2sn 723 7 and and CC cord-276598-tm0yj2sn 723 8 P P NNP cord-276598-tm0yj2sn 723 9 - - HYPH cord-276598-tm0yj2sn 723 10 N N NNP cord-276598-tm0yj2sn 723 11 with with IN cord-276598-tm0yj2sn 723 12 a a DT cord-276598-tm0yj2sn 723 13 free free JJ cord-276598-tm0yj2sn 723 14 amino amino NN cord-276598-tm0yj2sn 723 15 group group NN cord-276598-tm0yj2sn 723 16 were be VBD cord-276598-tm0yj2sn 723 17 also also RB cord-276598-tm0yj2sn 723 18 synthesized synthesize VBN cord-276598-tm0yj2sn 723 19 using use VBG cord-276598-tm0yj2sn 723 20 the the DT cord-276598-tm0yj2sn 723 21 iodine iodine NN cord-276598-tm0yj2sn 723 22 - - HYPH cord-276598-tm0yj2sn 723 23 mediated mediate VBN cord-276598-tm0yj2sn 723 24 synthesis synthesis NN cord-276598-tm0yj2sn 723 25 method method NN cord-276598-tm0yj2sn 723 26 . . . cord-276598-tm0yj2sn 724 1 The the DT cord-276598-tm0yj2sn 724 2 challenges challenge NNS cord-276598-tm0yj2sn 724 3 with with IN cord-276598-tm0yj2sn 724 4 this this DT cord-276598-tm0yj2sn 724 5 iodine iodine NN cord-276598-tm0yj2sn 724 6 - - HYPH cord-276598-tm0yj2sn 724 7 mediated mediate VBN cord-276598-tm0yj2sn 724 8 P p NN cord-276598-tm0yj2sn 724 9 - - HYPH cord-276598-tm0yj2sn 724 10 N n CD cord-276598-tm0yj2sn 724 11 formation formation NN cord-276598-tm0yj2sn 724 12 is be VBZ cord-276598-tm0yj2sn 724 13 that that IN cord-276598-tm0yj2sn 724 14 many many JJ cord-276598-tm0yj2sn 724 15 side side NN cord-276598-tm0yj2sn 724 16 products product NNS cord-276598-tm0yj2sn 724 17 are be VBP cord-276598-tm0yj2sn 724 18 formed form VBN cord-276598-tm0yj2sn 724 19 , , , cord-276598-tm0yj2sn 724 20 and and CC cord-276598-tm0yj2sn 724 21 the the DT cord-276598-tm0yj2sn 724 22 Scheme Scheme NNP cord-276598-tm0yj2sn 724 23 23 23 CD cord-276598-tm0yj2sn 724 24 . . . cord-276598-tm0yj2sn 725 1 Proposed propose VBN cord-276598-tm0yj2sn 725 2 mechanism mechanism NN cord-276598-tm0yj2sn 725 3 for for IN cord-276598-tm0yj2sn 725 4 the the DT cord-276598-tm0yj2sn 725 5 synthesis synthesis NN cord-276598-tm0yj2sn 725 6 of of IN cord-276598-tm0yj2sn 725 7 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 725 8 from from IN cord-276598-tm0yj2sn 725 9 phosphoric phosphoric JJ cord-276598-tm0yj2sn 725 10 acid acid NN cord-276598-tm0yj2sn 725 11 and and CC cord-276598-tm0yj2sn 725 12 amine amine NN cord-276598-tm0yj2sn 725 13 in in IN cord-276598-tm0yj2sn 725 14 the the DT cord-276598-tm0yj2sn 725 15 presence presence NN cord-276598-tm0yj2sn 725 16 of of IN cord-276598-tm0yj2sn 725 17 phosphine phosphine NN cord-276598-tm0yj2sn 725 18 and and CC cord-276598-tm0yj2sn 725 19 CCl CCl NNS cord-276598-tm0yj2sn 725 20 4 4 CD cord-276598-tm0yj2sn 725 21 . . . cord-276598-tm0yj2sn 726 1 In in IN cord-276598-tm0yj2sn 726 2 the the DT cord-276598-tm0yj2sn 726 3 suggested suggest VBN cord-276598-tm0yj2sn 726 4 reaction reaction NN cord-276598-tm0yj2sn 726 5 mechanism mechanism NN cord-276598-tm0yj2sn 726 6 by by IN cord-276598-tm0yj2sn 726 7 [ [ -LRB- cord-276598-tm0yj2sn 726 8 100 100 CD cord-276598-tm0yj2sn 726 9 ] ] -RRB- cord-276598-tm0yj2sn 726 10 , , , cord-276598-tm0yj2sn 726 11 iodine iodine NN cord-276598-tm0yj2sn 726 12 reacts react VBZ cord-276598-tm0yj2sn 726 13 with with IN cord-276598-tm0yj2sn 726 14 ( ( -LRB- cord-276598-tm0yj2sn 726 15 RO ro NN cord-276598-tm0yj2sn 726 16 ) ) -RRB- cord-276598-tm0yj2sn 726 17 3 3 CD cord-276598-tm0yj2sn 726 18 P p NN cord-276598-tm0yj2sn 726 19 ( ( -LRB- cord-276598-tm0yj2sn 726 20 R r NN cord-276598-tm0yj2sn 726 21 = = NN cord-276598-tm0yj2sn 726 22 alkyl alkyl NN cord-276598-tm0yj2sn 726 23 ) ) -RRB- cord-276598-tm0yj2sn 726 24 to to TO cord-276598-tm0yj2sn 726 25 form form VB cord-276598-tm0yj2sn 726 26 trialkoxyiodophosphonium trialkoxyiodophosphonium NN cord-276598-tm0yj2sn 726 27 intermediate intermediate JJ cord-276598-tm0yj2sn 726 28 , , , cord-276598-tm0yj2sn 726 29 which which WDT cord-276598-tm0yj2sn 726 30 is be VBZ cord-276598-tm0yj2sn 726 31 further further RB cord-276598-tm0yj2sn 726 32 attacked attack VBN cord-276598-tm0yj2sn 726 33 by by IN cord-276598-tm0yj2sn 726 34 iodide iodide NN cord-276598-tm0yj2sn 726 35 ion ion NN cord-276598-tm0yj2sn 726 36 to to TO cord-276598-tm0yj2sn 726 37 form form VB cord-276598-tm0yj2sn 726 38 dialkyl dialkyl FW cord-276598-tm0yj2sn 726 39 phosphoriodidate phosphoriodidate NNP cord-276598-tm0yj2sn 726 40 ( ( -LRB- cord-276598-tm0yj2sn 726 41 dAPPI dappi NN cord-276598-tm0yj2sn 726 42 ) ) -RRB- cord-276598-tm0yj2sn 727 1 ( ( -LRB- cord-276598-tm0yj2sn 727 2 Arbuzov Arbuzov NNP cord-276598-tm0yj2sn 727 3 reaction reaction NN cord-276598-tm0yj2sn 727 4 , , , cord-276598-tm0yj2sn 727 5 Scheme scheme NN cord-276598-tm0yj2sn 727 6 24 24 CD cord-276598-tm0yj2sn 727 7 ) ) -RRB- cord-276598-tm0yj2sn 727 8 . . . cord-276598-tm0yj2sn 728 1 Then then RB cord-276598-tm0yj2sn 728 2 , , , cord-276598-tm0yj2sn 728 3 the the DT cord-276598-tm0yj2sn 728 4 dAPPI dappi NN cord-276598-tm0yj2sn 728 5 is be VBZ cord-276598-tm0yj2sn 728 6 attacked attack VBN cord-276598-tm0yj2sn 728 7 by by IN cord-276598-tm0yj2sn 728 8 the the DT cord-276598-tm0yj2sn 728 9 amine amine NN cord-276598-tm0yj2sn 728 10 to to TO cord-276598-tm0yj2sn 728 11 give give VB cord-276598-tm0yj2sn 728 12 the the DT cord-276598-tm0yj2sn 728 13 desired desire VBN cord-276598-tm0yj2sn 728 14 P P NNP cord-276598-tm0yj2sn 728 15 - - HYPH cord-276598-tm0yj2sn 728 16 N N NNP cord-276598-tm0yj2sn 728 17 with with IN cord-276598-tm0yj2sn 728 18 an an DT cord-276598-tm0yj2sn 728 19 elimination elimination NN cord-276598-tm0yj2sn 728 20 of of IN cord-276598-tm0yj2sn 728 21 HI HI NNP cord-276598-tm0yj2sn 728 22 . . . cord-276598-tm0yj2sn 729 1 N N NNP cord-276598-tm0yj2sn 729 2 - - HYPH cord-276598-tm0yj2sn 729 3 phosphoryl phosphoryl NN cord-276598-tm0yj2sn 729 4 amino amino NN cord-276598-tm0yj2sn 729 5 acid acid NN cord-276598-tm0yj2sn 729 6 esters ester NNS cord-276598-tm0yj2sn 729 7 and and CC cord-276598-tm0yj2sn 729 8 P P NNP cord-276598-tm0yj2sn 729 9 - - HYPH cord-276598-tm0yj2sn 729 10 N N NNP cord-276598-tm0yj2sn 729 11 with with IN cord-276598-tm0yj2sn 729 12 a a DT cord-276598-tm0yj2sn 729 13 free free JJ cord-276598-tm0yj2sn 729 14 amino amino NN cord-276598-tm0yj2sn 729 15 group group NN cord-276598-tm0yj2sn 729 16 were be VBD cord-276598-tm0yj2sn 729 17 also also RB cord-276598-tm0yj2sn 729 18 synthesized synthesize VBN cord-276598-tm0yj2sn 729 19 using use VBG cord-276598-tm0yj2sn 729 20 the the DT cord-276598-tm0yj2sn 729 21 iodine iodine NN cord-276598-tm0yj2sn 729 22 - - HYPH cord-276598-tm0yj2sn 729 23 mediated mediate VBN cord-276598-tm0yj2sn 729 24 synthesis synthesis NN cord-276598-tm0yj2sn 729 25 method method NN cord-276598-tm0yj2sn 729 26 . . . cord-276598-tm0yj2sn 730 1 The the DT cord-276598-tm0yj2sn 730 2 challenges challenge NNS cord-276598-tm0yj2sn 730 3 with with IN cord-276598-tm0yj2sn 730 4 this this DT cord-276598-tm0yj2sn 730 5 iodine iodine NN cord-276598-tm0yj2sn 730 6 - - HYPH cord-276598-tm0yj2sn 730 7 mediated mediate VBN cord-276598-tm0yj2sn 730 8 P p NN cord-276598-tm0yj2sn 730 9 - - HYPH cord-276598-tm0yj2sn 730 10 N n CD cord-276598-tm0yj2sn 730 11 formation formation NN cord-276598-tm0yj2sn 730 12 is be VBZ cord-276598-tm0yj2sn 730 13 that that IN cord-276598-tm0yj2sn 730 14 many many JJ cord-276598-tm0yj2sn 730 15 side side NN cord-276598-tm0yj2sn 730 16 products product NNS cord-276598-tm0yj2sn 730 17 are be VBP cord-276598-tm0yj2sn 730 18 formed form VBN cord-276598-tm0yj2sn 730 19 , , , cord-276598-tm0yj2sn 730 20 and and CC cord-276598-tm0yj2sn 730 21 the the DT cord-276598-tm0yj2sn 730 22 reaction reaction NN cord-276598-tm0yj2sn 730 23 procedure procedure NN cord-276598-tm0yj2sn 730 24 does do VBZ cord-276598-tm0yj2sn 730 25 not not RB cord-276598-tm0yj2sn 730 26 generate generate VB cord-276598-tm0yj2sn 730 27 the the DT cord-276598-tm0yj2sn 730 28 desired desire VBN cord-276598-tm0yj2sn 730 29 product product NN cord-276598-tm0yj2sn 730 30 when when WRB cord-276598-tm0yj2sn 730 31 N n CD cord-276598-tm0yj2sn 730 32 - - HYPH cord-276598-tm0yj2sn 730 33 iodosuccinimide iodosuccinimide NNP cord-276598-tm0yj2sn 730 34 ( ( -LRB- cord-276598-tm0yj2sn 730 35 NIS NIS NNP cord-276598-tm0yj2sn 730 36 ) ) -RRB- cord-276598-tm0yj2sn 730 37 is be VBZ cord-276598-tm0yj2sn 730 38 used use VBN cord-276598-tm0yj2sn 730 39 as as IN cord-276598-tm0yj2sn 730 40 the the DT cord-276598-tm0yj2sn 730 41 iodine iodine NN cord-276598-tm0yj2sn 730 42 source source NN cord-276598-tm0yj2sn 730 43 . . . cord-276598-tm0yj2sn 731 1 In in IN cord-276598-tm0yj2sn 731 2 addition addition NN cord-276598-tm0yj2sn 731 3 , , , cord-276598-tm0yj2sn 731 4 the the DT cord-276598-tm0yj2sn 731 5 reaction reaction NN cord-276598-tm0yj2sn 731 6 process process NN cord-276598-tm0yj2sn 731 7 is be VBZ cord-276598-tm0yj2sn 731 8 ineffective ineffective JJ cord-276598-tm0yj2sn 731 9 with with IN cord-276598-tm0yj2sn 731 10 aromatic aromatic JJ cord-276598-tm0yj2sn 731 11 H h NN cord-276598-tm0yj2sn 731 12 - - HYPH cord-276598-tm0yj2sn 731 13 phosphonates phosphonate NNS cord-276598-tm0yj2sn 731 14 because because IN cord-276598-tm0yj2sn 731 15 the the DT cord-276598-tm0yj2sn 731 16 reaction reaction NN cord-276598-tm0yj2sn 731 17 is be VBZ cord-276598-tm0yj2sn 731 18 affected affect VBN cord-276598-tm0yj2sn 731 19 by by IN cord-276598-tm0yj2sn 731 20 steric steric JJ cord-276598-tm0yj2sn 731 21 effects effect NNS cord-276598-tm0yj2sn 731 22 on on IN cord-276598-tm0yj2sn 731 23 the the DT cord-276598-tm0yj2sn 731 24 substituents substituent NNS cord-276598-tm0yj2sn 731 25 . . . cord-276598-tm0yj2sn 732 1 In in IN cord-276598-tm0yj2sn 732 2 a a DT cord-276598-tm0yj2sn 732 3 mechanism mechanism NN cord-276598-tm0yj2sn 732 4 of of IN cord-276598-tm0yj2sn 732 5 the the DT cord-276598-tm0yj2sn 732 6 I I NNP cord-276598-tm0yj2sn 732 7 2 2 CD cord-276598-tm0yj2sn 732 8 -mediated -mediated JJ cord-276598-tm0yj2sn 732 9 P P NNP cord-276598-tm0yj2sn 732 10 - - HYPH cord-276598-tm0yj2sn 732 11 N n CD cord-276598-tm0yj2sn 732 12 formation formation NN cord-276598-tm0yj2sn 732 13 , , , cord-276598-tm0yj2sn 732 14 according accord VBG cord-276598-tm0yj2sn 732 15 to to IN cord-276598-tm0yj2sn 732 16 Singh Singh NNP cord-276598-tm0yj2sn 732 17 et et NNP cord-276598-tm0yj2sn 732 18 al al NNP cord-276598-tm0yj2sn 732 19 . . . cord-276598-tm0yj2sn 733 1 , , , cord-276598-tm0yj2sn 733 2 H H NNP cord-276598-tm0yj2sn 733 3 - - HYPH cord-276598-tm0yj2sn 733 4 P P NNP cord-276598-tm0yj2sn 733 5 reacts react VBZ cord-276598-tm0yj2sn 733 6 with with IN cord-276598-tm0yj2sn 733 7 I -PRON- PRP cord-276598-tm0yj2sn 733 8 2 2 CD cord-276598-tm0yj2sn 733 9 to to TO cord-276598-tm0yj2sn 733 10 form form VB cord-276598-tm0yj2sn 733 11 an an DT cord-276598-tm0yj2sn 733 12 intermediate intermediate JJ cord-276598-tm0yj2sn 733 13 , , , cord-276598-tm0yj2sn 733 14 which which WDT cord-276598-tm0yj2sn 733 15 undergoes undergo VBZ cord-276598-tm0yj2sn 733 16 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 733 17 attack attack NN cord-276598-tm0yj2sn 733 18 from from IN cord-276598-tm0yj2sn 733 19 the the DT cord-276598-tm0yj2sn 733 20 amine amine NN cord-276598-tm0yj2sn 733 21 to to TO cord-276598-tm0yj2sn 733 22 generate generate VB cord-276598-tm0yj2sn 733 23 a a DT cord-276598-tm0yj2sn 733 24 hydroxylated hydroxylate VBN cord-276598-tm0yj2sn 733 25 - - HYPH cord-276598-tm0yj2sn 733 26 dialkyl dialkyl NN cord-276598-tm0yj2sn 733 27 phenylphosphoramidate phenylphosphoramidate NN cord-276598-tm0yj2sn 733 28 complex complex NN cord-276598-tm0yj2sn 733 29 with with IN cord-276598-tm0yj2sn 733 30 an an DT cord-276598-tm0yj2sn 733 31 elimination elimination NN cord-276598-tm0yj2sn 733 32 of of IN cord-276598-tm0yj2sn 733 33 I i NN cord-276598-tm0yj2sn 733 34 2 2 CD cord-276598-tm0yj2sn 733 35 ( ( -LRB- cord-276598-tm0yj2sn 733 36 Scheme scheme NN cord-276598-tm0yj2sn 733 37 25 25 CD cord-276598-tm0yj2sn 733 38 ) ) -RRB- cord-276598-tm0yj2sn 734 1 [ [ -LRB- cord-276598-tm0yj2sn 734 2 101 101 CD cord-276598-tm0yj2sn 734 3 ] ] -RRB- cord-276598-tm0yj2sn 734 4 . . . cord-276598-tm0yj2sn 735 1 The the DT cord-276598-tm0yj2sn 735 2 phosphoramidate phosphoramidate NN cord-276598-tm0yj2sn 735 3 complex complex NN cord-276598-tm0yj2sn 735 4 further further RB cord-276598-tm0yj2sn 735 5 undergoes undergo VBZ cord-276598-tm0yj2sn 735 6 dehydrogenation dehydrogenation NN cord-276598-tm0yj2sn 735 7 to to TO cord-276598-tm0yj2sn 735 8 eliminate eliminate VB cord-276598-tm0yj2sn 735 9 H H NNP cord-276598-tm0yj2sn 735 10 2 2 CD cord-276598-tm0yj2sn 735 11 in in IN cord-276598-tm0yj2sn 735 12 form form NN cord-276598-tm0yj2sn 735 13 of of IN cord-276598-tm0yj2sn 735 14 H h NN cord-276598-tm0yj2sn 735 15 2 2 CD cord-276598-tm0yj2sn 735 16 O o NN cord-276598-tm0yj2sn 735 17 and and CC cord-276598-tm0yj2sn 735 18 afford afford VB cord-276598-tm0yj2sn 735 19 the the DT cord-276598-tm0yj2sn 735 20 desired desire VBN cord-276598-tm0yj2sn 735 21 products product NNS cord-276598-tm0yj2sn 735 22 . . . cord-276598-tm0yj2sn 736 1 The the DT cord-276598-tm0yj2sn 736 2 suggested suggested JJ cord-276598-tm0yj2sn 736 3 mechanism mechanism NN cord-276598-tm0yj2sn 736 4 of of IN cord-276598-tm0yj2sn 736 5 a a DT cord-276598-tm0yj2sn 736 6 similar similar JJ cord-276598-tm0yj2sn 736 7 reaction reaction NN cord-276598-tm0yj2sn 736 8 reported report VBN cord-276598-tm0yj2sn 736 9 by by IN cord-276598-tm0yj2sn 736 10 Prabhu Prabhu NNP cord-276598-tm0yj2sn 736 11 et et NNP cord-276598-tm0yj2sn 736 12 al al NNP cord-276598-tm0yj2sn 736 13 . . . cord-276598-tm0yj2sn 737 1 instead instead RB cord-276598-tm0yj2sn 737 2 involves involve VBZ cord-276598-tm0yj2sn 737 3 the the DT cord-276598-tm0yj2sn 737 4 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 737 5 substitution substitution NN cord-276598-tm0yj2sn 737 6 of of IN cord-276598-tm0yj2sn 737 7 phosphoriodate phosphoriodate NN cord-276598-tm0yj2sn 737 8 intermediate intermediate JJ cord-276598-tm0yj2sn 737 9 after after IN cord-276598-tm0yj2sn 737 10 the the DT cord-276598-tm0yj2sn 737 11 electrophilic electrophilic JJ cord-276598-tm0yj2sn 737 12 iodination iodination NN cord-276598-tm0yj2sn 737 13 of of IN cord-276598-tm0yj2sn 737 14 the the DT cord-276598-tm0yj2sn 737 15 H H NNP cord-276598-tm0yj2sn 737 16 - - HYPH cord-276598-tm0yj2sn 737 17 P p NN cord-276598-tm0yj2sn 737 18 starting starting NN cord-276598-tm0yj2sn 737 19 material material NN cord-276598-tm0yj2sn 737 20 ( ( -LRB- cord-276598-tm0yj2sn 737 21 Scheme scheme NN cord-276598-tm0yj2sn 737 22 26 26 CD cord-276598-tm0yj2sn 737 23 ) ) -RRB- cord-276598-tm0yj2sn 737 24 [ [ -LRB- cord-276598-tm0yj2sn 737 25 102 102 CD cord-276598-tm0yj2sn 737 26 ] ] -RRB- cord-276598-tm0yj2sn 737 27 . . . cord-276598-tm0yj2sn 738 1 Then then RB cord-276598-tm0yj2sn 738 2 , , , cord-276598-tm0yj2sn 738 3 the the DT cord-276598-tm0yj2sn 738 4 iodide iodide NN cord-276598-tm0yj2sn 738 5 ion ion NN cord-276598-tm0yj2sn 738 6 is be VBZ cord-276598-tm0yj2sn 738 7 oxidized oxidize VBN cord-276598-tm0yj2sn 738 8 to to IN cord-276598-tm0yj2sn 738 9 active active JJ cord-276598-tm0yj2sn 738 10 catalyst catalyst NN cord-276598-tm0yj2sn 738 11 , , , cord-276598-tm0yj2sn 738 12 hypoiodous hypoiodous JJ cord-276598-tm0yj2sn 738 13 acid acid NN cord-276598-tm0yj2sn 738 14 , , , cord-276598-tm0yj2sn 738 15 in in IN cord-276598-tm0yj2sn 738 16 the the DT cord-276598-tm0yj2sn 738 17 presence presence NN cord-276598-tm0yj2sn 738 18 of of IN cord-276598-tm0yj2sn 738 19 H h NN cord-276598-tm0yj2sn 738 20 2 2 CD cord-276598-tm0yj2sn 738 21 O o NN cord-276598-tm0yj2sn 738 22 2 2 CD cord-276598-tm0yj2sn 738 23 . . . cord-276598-tm0yj2sn 739 1 Molecules molecule NNS cord-276598-tm0yj2sn 739 2 2020 2020 CD cord-276598-tm0yj2sn 739 3 , , , cord-276598-tm0yj2sn 739 4 25 25 CD cord-276598-tm0yj2sn 739 5 , , , cord-276598-tm0yj2sn 739 6 x x NN cord-276598-tm0yj2sn 739 7 FOR for IN cord-276598-tm0yj2sn 739 8 PEER PEER NNP cord-276598-tm0yj2sn 739 9 REVIEW REVIEW NNP cord-276598-tm0yj2sn 739 10 22 22 CD cord-276598-tm0yj2sn 739 11 of of IN cord-276598-tm0yj2sn 739 12 37 37 CD cord-276598-tm0yj2sn 739 13 reaction reaction NN cord-276598-tm0yj2sn 739 14 procedure procedure NN cord-276598-tm0yj2sn 739 15 does do VBZ cord-276598-tm0yj2sn 739 16 not not RB cord-276598-tm0yj2sn 739 17 generate generate VB cord-276598-tm0yj2sn 739 18 the the DT cord-276598-tm0yj2sn 739 19 desired desire VBN cord-276598-tm0yj2sn 739 20 product product NN cord-276598-tm0yj2sn 739 21 when when WRB cord-276598-tm0yj2sn 739 22 N n CD cord-276598-tm0yj2sn 739 23 - - HYPH cord-276598-tm0yj2sn 739 24 iodosuccinimide iodosuccinimide NNP cord-276598-tm0yj2sn 739 25 ( ( -LRB- cord-276598-tm0yj2sn 739 26 NIS NIS NNP cord-276598-tm0yj2sn 739 27 ) ) -RRB- cord-276598-tm0yj2sn 739 28 is be VBZ cord-276598-tm0yj2sn 739 29 used use VBN cord-276598-tm0yj2sn 739 30 as as IN cord-276598-tm0yj2sn 739 31 the the DT cord-276598-tm0yj2sn 739 32 iodine iodine NN cord-276598-tm0yj2sn 739 33 source source NN cord-276598-tm0yj2sn 739 34 . . . cord-276598-tm0yj2sn 740 1 In in IN cord-276598-tm0yj2sn 740 2 addition addition NN cord-276598-tm0yj2sn 740 3 , , , cord-276598-tm0yj2sn 740 4 the the DT cord-276598-tm0yj2sn 740 5 reaction reaction NN cord-276598-tm0yj2sn 740 6 process process NN cord-276598-tm0yj2sn 740 7 is be VBZ cord-276598-tm0yj2sn 740 8 ineffective ineffective JJ cord-276598-tm0yj2sn 740 9 with with IN cord-276598-tm0yj2sn 740 10 aromatic aromatic JJ cord-276598-tm0yj2sn 740 11 H h NN cord-276598-tm0yj2sn 740 12 - - HYPH cord-276598-tm0yj2sn 740 13 phosphonates phosphonate NNS cord-276598-tm0yj2sn 740 14 because because IN cord-276598-tm0yj2sn 740 15 the the DT cord-276598-tm0yj2sn 740 16 reaction reaction NN cord-276598-tm0yj2sn 740 17 is be VBZ cord-276598-tm0yj2sn 740 18 affected affect VBN cord-276598-tm0yj2sn 740 19 by by IN cord-276598-tm0yj2sn 740 20 steric steric JJ cord-276598-tm0yj2sn 740 21 effects effect NNS cord-276598-tm0yj2sn 740 22 on on IN cord-276598-tm0yj2sn 740 23 the the DT cord-276598-tm0yj2sn 740 24 substituents substituent NNS cord-276598-tm0yj2sn 740 25 . . . cord-276598-tm0yj2sn 741 1 Proposed propose VBN cord-276598-tm0yj2sn 741 2 mechanism mechanism NN cord-276598-tm0yj2sn 741 3 for for IN cord-276598-tm0yj2sn 741 4 the the DT cord-276598-tm0yj2sn 741 5 iodine iodine NN cord-276598-tm0yj2sn 741 6 - - HYPH cord-276598-tm0yj2sn 741 7 mediated mediate VBN cord-276598-tm0yj2sn 741 8 synthesis synthesis NN cord-276598-tm0yj2sn 741 9 of of IN cord-276598-tm0yj2sn 741 10 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 741 11 . . . cord-276598-tm0yj2sn 742 1 In in IN cord-276598-tm0yj2sn 742 2 a a DT cord-276598-tm0yj2sn 742 3 mechanism mechanism NN cord-276598-tm0yj2sn 742 4 of of IN cord-276598-tm0yj2sn 742 5 the the DT cord-276598-tm0yj2sn 742 6 I2-mediated I2-mediated NNP cord-276598-tm0yj2sn 742 7 P P NNP cord-276598-tm0yj2sn 742 8 - - HYPH cord-276598-tm0yj2sn 742 9 N N NNP cord-276598-tm0yj2sn 742 10 formation formation NN cord-276598-tm0yj2sn 742 11 , , , cord-276598-tm0yj2sn 742 12 according accord VBG cord-276598-tm0yj2sn 742 13 to to IN cord-276598-tm0yj2sn 742 14 Singh Singh NNP cord-276598-tm0yj2sn 742 15 et et NNP cord-276598-tm0yj2sn 742 16 al al NNP cord-276598-tm0yj2sn 742 17 . . NNP cord-276598-tm0yj2sn 742 18 , , , cord-276598-tm0yj2sn 742 19 H H NNP cord-276598-tm0yj2sn 742 20 - - HYPH cord-276598-tm0yj2sn 742 21 P P NNP cord-276598-tm0yj2sn 742 22 reacts react VBZ cord-276598-tm0yj2sn 742 23 with with IN cord-276598-tm0yj2sn 742 24 I2 I2 NNP cord-276598-tm0yj2sn 742 25 to to TO cord-276598-tm0yj2sn 742 26 form form VB cord-276598-tm0yj2sn 742 27 an an DT cord-276598-tm0yj2sn 742 28 intermediate intermediate JJ cord-276598-tm0yj2sn 742 29 , , , cord-276598-tm0yj2sn 742 30 which which WDT cord-276598-tm0yj2sn 742 31 undergoes undergo VBZ cord-276598-tm0yj2sn 742 32 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 742 33 attack attack NN cord-276598-tm0yj2sn 742 34 from from IN cord-276598-tm0yj2sn 742 35 the the DT cord-276598-tm0yj2sn 742 36 amine amine NN cord-276598-tm0yj2sn 742 37 to to TO cord-276598-tm0yj2sn 742 38 generate generate VB cord-276598-tm0yj2sn 742 39 a a DT cord-276598-tm0yj2sn 742 40 hydroxylated hydroxylate VBN cord-276598-tm0yj2sn 742 41 - - HYPH cord-276598-tm0yj2sn 742 42 dialkyl dialkyl NN cord-276598-tm0yj2sn 742 43 phenylphosphoramidate phenylphosphoramidate NN cord-276598-tm0yj2sn 742 44 complex complex NN cord-276598-tm0yj2sn 742 45 with with IN cord-276598-tm0yj2sn 742 46 an an DT cord-276598-tm0yj2sn 742 47 elimination elimination NN cord-276598-tm0yj2sn 742 48 of of IN cord-276598-tm0yj2sn 742 49 I2 I2 NNP cord-276598-tm0yj2sn 742 50 ( ( -LRB- cord-276598-tm0yj2sn 742 51 Scheme scheme NN cord-276598-tm0yj2sn 742 52 25 25 CD cord-276598-tm0yj2sn 742 53 ) ) -RRB- cord-276598-tm0yj2sn 742 54 [ [ -LRB- cord-276598-tm0yj2sn 742 55 101 101 CD cord-276598-tm0yj2sn 742 56 ] ] -RRB- cord-276598-tm0yj2sn 742 57 . . . cord-276598-tm0yj2sn 743 1 The the DT cord-276598-tm0yj2sn 743 2 phosphoramidate phosphoramidate NN cord-276598-tm0yj2sn 743 3 complex complex NN cord-276598-tm0yj2sn 743 4 further further RB cord-276598-tm0yj2sn 743 5 undergoes undergo VBZ cord-276598-tm0yj2sn 743 6 dehydrogenation dehydrogenation NN cord-276598-tm0yj2sn 743 7 to to TO cord-276598-tm0yj2sn 743 8 eliminate eliminate VB cord-276598-tm0yj2sn 743 9 H2 H2 NNP cord-276598-tm0yj2sn 743 10 in in IN cord-276598-tm0yj2sn 743 11 form form NN cord-276598-tm0yj2sn 743 12 of of IN cord-276598-tm0yj2sn 743 13 H2O h2o NN cord-276598-tm0yj2sn 743 14 and and CC cord-276598-tm0yj2sn 743 15 afford afford VB cord-276598-tm0yj2sn 743 16 the the DT cord-276598-tm0yj2sn 743 17 desired desire VBN cord-276598-tm0yj2sn 743 18 products product NNS cord-276598-tm0yj2sn 743 19 . . . cord-276598-tm0yj2sn 744 1 [ [ -LRB- cord-276598-tm0yj2sn 744 2 102 102 CD cord-276598-tm0yj2sn 744 3 ] ] -RRB- cord-276598-tm0yj2sn 744 4 . . . cord-276598-tm0yj2sn 745 1 Then then RB cord-276598-tm0yj2sn 745 2 , , , cord-276598-tm0yj2sn 745 3 the the DT cord-276598-tm0yj2sn 745 4 iodide iodide NN cord-276598-tm0yj2sn 745 5 ion ion NN cord-276598-tm0yj2sn 745 6 is be VBZ cord-276598-tm0yj2sn 745 7 oxidized oxidize VBN cord-276598-tm0yj2sn 745 8 to to IN cord-276598-tm0yj2sn 745 9 active active JJ cord-276598-tm0yj2sn 745 10 catalyst catalyst NN cord-276598-tm0yj2sn 745 11 , , , cord-276598-tm0yj2sn 745 12 hypoiodous hypoiodous JJ cord-276598-tm0yj2sn 745 13 acid acid NN cord-276598-tm0yj2sn 745 14 , , , cord-276598-tm0yj2sn 745 15 in in IN cord-276598-tm0yj2sn 745 16 the the DT cord-276598-tm0yj2sn 745 17 presence presence NN cord-276598-tm0yj2sn 745 18 of of IN cord-276598-tm0yj2sn 745 19 H2O2 H2O2 NNP cord-276598-tm0yj2sn 745 20 . . . cord-276598-tm0yj2sn 746 1 Scheme scheme NN cord-276598-tm0yj2sn 746 2 26 26 CD cord-276598-tm0yj2sn 746 3 . . . cord-276598-tm0yj2sn 747 1 Proposed propose VBN cord-276598-tm0yj2sn 747 2 mechanism mechanism NN cord-276598-tm0yj2sn 747 3 for for IN cord-276598-tm0yj2sn 747 4 the the DT cord-276598-tm0yj2sn 747 5 hypoiodous hypoiodous JJ cord-276598-tm0yj2sn 747 6 acid acid NN cord-276598-tm0yj2sn 747 7 - - HYPH cord-276598-tm0yj2sn 747 8 mediated mediate VBN cord-276598-tm0yj2sn 747 9 synthesis synthesis NN cord-276598-tm0yj2sn 747 10 of of IN cord-276598-tm0yj2sn 747 11 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 747 12 . . . cord-276598-tm0yj2sn 748 1 In in IN cord-276598-tm0yj2sn 748 2 a a DT cord-276598-tm0yj2sn 748 3 copper copper NN cord-276598-tm0yj2sn 748 4 - - HYPH cord-276598-tm0yj2sn 748 5 catalyzed catalyze VBN cord-276598-tm0yj2sn 748 6 oxidative oxidative JJ cord-276598-tm0yj2sn 748 7 cross cross JJ cord-276598-tm0yj2sn 748 8 - - JJ cord-276598-tm0yj2sn 748 9 coupling coupling JJ cord-276598-tm0yj2sn 748 10 reaction reaction NN cord-276598-tm0yj2sn 748 11 , , , cord-276598-tm0yj2sn 748 12 Hayes Hayes NNP cord-276598-tm0yj2sn 748 13 et et NNP cord-276598-tm0yj2sn 748 14 al al NNP cord-276598-tm0yj2sn 748 15 . . NNP cord-276598-tm0yj2sn 748 16 proposed propose VBD cord-276598-tm0yj2sn 748 17 a a DT cord-276598-tm0yj2sn 748 18 reaction reaction NN cord-276598-tm0yj2sn 748 19 mechanism mechanism NN cord-276598-tm0yj2sn 748 20 involving involve VBG cord-276598-tm0yj2sn 748 21 single single JJ cord-276598-tm0yj2sn 748 22 - - HYPH cord-276598-tm0yj2sn 748 23 electron electron NN cord-276598-tm0yj2sn 748 24 transfer transfer NN cord-276598-tm0yj2sn 748 25 oxidation oxidation NN cord-276598-tm0yj2sn 748 26 of of IN cord-276598-tm0yj2sn 748 27 the the DT cord-276598-tm0yj2sn 748 28 copper copper NN cord-276598-tm0yj2sn 748 29 catalyst catalyst NN cord-276598-tm0yj2sn 748 30 , , , cord-276598-tm0yj2sn 748 31 which which WDT cord-276598-tm0yj2sn 748 32 favored favor VBD cord-276598-tm0yj2sn 748 33 the the DT cord-276598-tm0yj2sn 748 34 formation formation NN cord-276598-tm0yj2sn 748 35 of of IN cord-276598-tm0yj2sn 748 36 the the DT cord-276598-tm0yj2sn 748 37 Cu(II)-amine Cu(II)-amine NNP cord-276598-tm0yj2sn 748 38 complex complex NN cord-276598-tm0yj2sn 748 39 ( ( -LRB- cord-276598-tm0yj2sn 748 40 Scheme scheme NN cord-276598-tm0yj2sn 748 41 27 27 CD cord-276598-tm0yj2sn 748 42 ) ) -RRB- cord-276598-tm0yj2sn 748 43 [ [ -LRB- cord-276598-tm0yj2sn 748 44 103 103 CD cord-276598-tm0yj2sn 748 45 ] ] -RRB- cord-276598-tm0yj2sn 748 46 . . . cord-276598-tm0yj2sn 749 1 The the DT cord-276598-tm0yj2sn 749 2 Cu(II)-amine Cu(II)-amine NNP cord-276598-tm0yj2sn 749 3 complex complex NN cord-276598-tm0yj2sn 749 4 is be VBZ cord-276598-tm0yj2sn 749 5 further further JJ cord-276598-tm0yj2sn 749 6 Scheme scheme NN cord-276598-tm0yj2sn 749 7 24 24 CD cord-276598-tm0yj2sn 749 8 . . . cord-276598-tm0yj2sn 750 1 Proposed propose VBN cord-276598-tm0yj2sn 750 2 mechanism mechanism NN cord-276598-tm0yj2sn 750 3 for for IN cord-276598-tm0yj2sn 750 4 the the DT cord-276598-tm0yj2sn 750 5 iodine iodine NN cord-276598-tm0yj2sn 750 6 - - HYPH cord-276598-tm0yj2sn 750 7 mediated mediate VBN cord-276598-tm0yj2sn 750 8 synthesis synthesis NN cord-276598-tm0yj2sn 750 9 of of IN cord-276598-tm0yj2sn 750 10 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 750 11 . . . cord-276598-tm0yj2sn 751 1 because because IN cord-276598-tm0yj2sn 751 2 the the DT cord-276598-tm0yj2sn 751 3 reaction reaction NN cord-276598-tm0yj2sn 751 4 is be VBZ cord-276598-tm0yj2sn 751 5 affected affect VBN cord-276598-tm0yj2sn 751 6 by by IN cord-276598-tm0yj2sn 751 7 steric steric JJ cord-276598-tm0yj2sn 751 8 effects effect NNS cord-276598-tm0yj2sn 751 9 on on IN cord-276598-tm0yj2sn 751 10 the the DT cord-276598-tm0yj2sn 751 11 substituents substituent NNS cord-276598-tm0yj2sn 751 12 . . . cord-276598-tm0yj2sn 752 1 Scheme scheme NN cord-276598-tm0yj2sn 752 2 24 24 CD cord-276598-tm0yj2sn 752 3 . . . cord-276598-tm0yj2sn 753 1 Proposed propose VBN cord-276598-tm0yj2sn 753 2 mechanism mechanism NN cord-276598-tm0yj2sn 753 3 for for IN cord-276598-tm0yj2sn 753 4 the the DT cord-276598-tm0yj2sn 753 5 iodine iodine NN cord-276598-tm0yj2sn 753 6 - - HYPH cord-276598-tm0yj2sn 753 7 mediated mediate VBN cord-276598-tm0yj2sn 753 8 synthesis synthesis NN cord-276598-tm0yj2sn 753 9 of of IN cord-276598-tm0yj2sn 753 10 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 753 11 . . . cord-276598-tm0yj2sn 754 1 In in IN cord-276598-tm0yj2sn 754 2 a a DT cord-276598-tm0yj2sn 754 3 mechanism mechanism NN cord-276598-tm0yj2sn 754 4 of of IN cord-276598-tm0yj2sn 754 5 the the DT cord-276598-tm0yj2sn 754 6 I2-mediated I2-mediated NNP cord-276598-tm0yj2sn 754 7 P P NNP cord-276598-tm0yj2sn 754 8 - - HYPH cord-276598-tm0yj2sn 754 9 N N NNP cord-276598-tm0yj2sn 754 10 formation formation NN cord-276598-tm0yj2sn 754 11 , , , cord-276598-tm0yj2sn 754 12 according accord VBG cord-276598-tm0yj2sn 754 13 to to IN cord-276598-tm0yj2sn 754 14 Singh Singh NNP cord-276598-tm0yj2sn 754 15 et et NNP cord-276598-tm0yj2sn 754 16 al al NNP cord-276598-tm0yj2sn 754 17 . . NNP cord-276598-tm0yj2sn 754 18 , , , cord-276598-tm0yj2sn 754 19 H H NNP cord-276598-tm0yj2sn 754 20 - - HYPH cord-276598-tm0yj2sn 754 21 P P NNP cord-276598-tm0yj2sn 754 22 reacts react VBZ cord-276598-tm0yj2sn 754 23 with with IN cord-276598-tm0yj2sn 754 24 I2 I2 NNP cord-276598-tm0yj2sn 754 25 to to TO cord-276598-tm0yj2sn 754 26 form form VB cord-276598-tm0yj2sn 754 27 an an DT cord-276598-tm0yj2sn 754 28 intermediate intermediate JJ cord-276598-tm0yj2sn 754 29 , , , cord-276598-tm0yj2sn 754 30 which which WDT cord-276598-tm0yj2sn 754 31 undergoes undergo VBZ cord-276598-tm0yj2sn 754 32 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 754 33 attack attack NN cord-276598-tm0yj2sn 754 34 from from IN cord-276598-tm0yj2sn 754 35 the the DT cord-276598-tm0yj2sn 754 36 amine amine NN cord-276598-tm0yj2sn 754 37 to to TO cord-276598-tm0yj2sn 754 38 generate generate VB cord-276598-tm0yj2sn 754 39 a a DT cord-276598-tm0yj2sn 754 40 hydroxylated hydroxylate VBN cord-276598-tm0yj2sn 754 41 - - HYPH cord-276598-tm0yj2sn 754 42 dialkyl dialkyl NN cord-276598-tm0yj2sn 754 43 phenylphosphoramidate phenylphosphoramidate NN cord-276598-tm0yj2sn 754 44 complex complex NN cord-276598-tm0yj2sn 754 45 with with IN cord-276598-tm0yj2sn 754 46 an an DT cord-276598-tm0yj2sn 754 47 elimination elimination NN cord-276598-tm0yj2sn 754 48 of of IN cord-276598-tm0yj2sn 754 49 I2 I2 NNP cord-276598-tm0yj2sn 754 50 ( ( -LRB- cord-276598-tm0yj2sn 754 51 Scheme scheme NN cord-276598-tm0yj2sn 754 52 25 25 CD cord-276598-tm0yj2sn 754 53 ) ) -RRB- cord-276598-tm0yj2sn 754 54 [ [ -LRB- cord-276598-tm0yj2sn 754 55 101 101 CD cord-276598-tm0yj2sn 754 56 ] ] -RRB- cord-276598-tm0yj2sn 754 57 . . . cord-276598-tm0yj2sn 755 1 The the DT cord-276598-tm0yj2sn 755 2 phosphoramidate phosphoramidate NN cord-276598-tm0yj2sn 755 3 complex complex NN cord-276598-tm0yj2sn 755 4 further further RB cord-276598-tm0yj2sn 755 5 undergoes undergo VBZ cord-276598-tm0yj2sn 755 6 dehydrogenation dehydrogenation NN cord-276598-tm0yj2sn 755 7 to to TO cord-276598-tm0yj2sn 755 8 eliminate eliminate VB cord-276598-tm0yj2sn 755 9 H2 H2 NNP cord-276598-tm0yj2sn 755 10 in in IN cord-276598-tm0yj2sn 755 11 form form NN cord-276598-tm0yj2sn 755 12 of of IN cord-276598-tm0yj2sn 755 13 H2O h2o NN cord-276598-tm0yj2sn 755 14 and and CC cord-276598-tm0yj2sn 755 15 afford afford VB cord-276598-tm0yj2sn 755 16 the the DT cord-276598-tm0yj2sn 755 17 desired desire VBN cord-276598-tm0yj2sn 755 18 products product NNS cord-276598-tm0yj2sn 755 19 . . . cord-276598-tm0yj2sn 756 1 [ [ -LRB- cord-276598-tm0yj2sn 756 2 102 102 CD cord-276598-tm0yj2sn 756 3 ] ] -RRB- cord-276598-tm0yj2sn 756 4 . . . cord-276598-tm0yj2sn 757 1 Then then RB cord-276598-tm0yj2sn 757 2 , , , cord-276598-tm0yj2sn 757 3 the the DT cord-276598-tm0yj2sn 757 4 iodide iodide NN cord-276598-tm0yj2sn 757 5 ion ion NN cord-276598-tm0yj2sn 757 6 is be VBZ cord-276598-tm0yj2sn 757 7 oxidized oxidize VBN cord-276598-tm0yj2sn 757 8 to to IN cord-276598-tm0yj2sn 757 9 active active JJ cord-276598-tm0yj2sn 757 10 catalyst catalyst NN cord-276598-tm0yj2sn 757 11 , , , cord-276598-tm0yj2sn 757 12 hypoiodous hypoiodous JJ cord-276598-tm0yj2sn 757 13 acid acid NN cord-276598-tm0yj2sn 757 14 , , , cord-276598-tm0yj2sn 757 15 in in IN cord-276598-tm0yj2sn 757 16 the the DT cord-276598-tm0yj2sn 757 17 presence presence NN cord-276598-tm0yj2sn 757 18 of of IN cord-276598-tm0yj2sn 757 19 H2O2 H2O2 NNP cord-276598-tm0yj2sn 757 20 . . . cord-276598-tm0yj2sn 758 1 Proposed propose VBN cord-276598-tm0yj2sn 758 2 mechanism mechanism NN cord-276598-tm0yj2sn 758 3 for for IN cord-276598-tm0yj2sn 758 4 the the DT cord-276598-tm0yj2sn 758 5 hypoiodous hypoiodous JJ cord-276598-tm0yj2sn 758 6 acid acid NN cord-276598-tm0yj2sn 758 7 - - HYPH cord-276598-tm0yj2sn 758 8 mediated mediate VBN cord-276598-tm0yj2sn 758 9 synthesis synthesis NN cord-276598-tm0yj2sn 758 10 of of IN cord-276598-tm0yj2sn 758 11 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 758 12 . . . cord-276598-tm0yj2sn 759 1 In in IN cord-276598-tm0yj2sn 759 2 a a DT cord-276598-tm0yj2sn 759 3 copper copper NN cord-276598-tm0yj2sn 759 4 - - HYPH cord-276598-tm0yj2sn 759 5 catalyzed catalyze VBN cord-276598-tm0yj2sn 759 6 oxidative oxidative JJ cord-276598-tm0yj2sn 759 7 cross cross JJ cord-276598-tm0yj2sn 759 8 - - JJ cord-276598-tm0yj2sn 759 9 coupling coupling JJ cord-276598-tm0yj2sn 759 10 reaction reaction NN cord-276598-tm0yj2sn 759 11 , , , cord-276598-tm0yj2sn 759 12 Hayes Hayes NNP cord-276598-tm0yj2sn 759 13 et et NNP cord-276598-tm0yj2sn 759 14 al al NNP cord-276598-tm0yj2sn 759 15 . . NNP cord-276598-tm0yj2sn 759 16 proposed propose VBD cord-276598-tm0yj2sn 759 17 a a DT cord-276598-tm0yj2sn 759 18 reaction reaction NN cord-276598-tm0yj2sn 759 19 mechanism mechanism NN cord-276598-tm0yj2sn 759 20 involving involve VBG cord-276598-tm0yj2sn 759 21 single single JJ cord-276598-tm0yj2sn 759 22 - - HYPH cord-276598-tm0yj2sn 759 23 electron electron NN cord-276598-tm0yj2sn 759 24 transfer transfer NN cord-276598-tm0yj2sn 759 25 oxidation oxidation NN cord-276598-tm0yj2sn 759 26 of of IN cord-276598-tm0yj2sn 759 27 the the DT cord-276598-tm0yj2sn 759 28 copper copper NN cord-276598-tm0yj2sn 759 29 catalyst catalyst NN cord-276598-tm0yj2sn 759 30 , , , cord-276598-tm0yj2sn 759 31 which which WDT cord-276598-tm0yj2sn 759 32 favored favor VBD cord-276598-tm0yj2sn 759 33 the the DT cord-276598-tm0yj2sn 759 34 formation formation NN cord-276598-tm0yj2sn 759 35 of of IN cord-276598-tm0yj2sn 759 36 the the DT cord-276598-tm0yj2sn 759 37 Cu(II)-amine Cu(II)-amine NNP cord-276598-tm0yj2sn 759 38 complex complex NN cord-276598-tm0yj2sn 759 39 ( ( -LRB- cord-276598-tm0yj2sn 759 40 Scheme scheme NN cord-276598-tm0yj2sn 759 41 27 27 CD cord-276598-tm0yj2sn 759 42 ) ) -RRB- cord-276598-tm0yj2sn 759 43 [ [ -LRB- cord-276598-tm0yj2sn 759 44 103 103 CD cord-276598-tm0yj2sn 759 45 ] ] -RRB- cord-276598-tm0yj2sn 759 46 . . . cord-276598-tm0yj2sn 760 1 The the DT cord-276598-tm0yj2sn 760 2 Cu(II)-amine Cu(II)-amine NNP cord-276598-tm0yj2sn 760 3 complex complex NN cord-276598-tm0yj2sn 760 4 is be VBZ cord-276598-tm0yj2sn 760 5 further further JJ cord-276598-tm0yj2sn 760 6 Scheme scheme NN cord-276598-tm0yj2sn 760 7 25 25 CD cord-276598-tm0yj2sn 760 8 . . . cord-276598-tm0yj2sn 761 1 Proposed propose VBN cord-276598-tm0yj2sn 761 2 mechanism mechanism NN cord-276598-tm0yj2sn 761 3 for for IN cord-276598-tm0yj2sn 761 4 the the DT cord-276598-tm0yj2sn 761 5 iodine iodine NN cord-276598-tm0yj2sn 761 6 - - HYPH cord-276598-tm0yj2sn 761 7 mediated mediate VBN cord-276598-tm0yj2sn 761 8 synthesis synthesis NN cord-276598-tm0yj2sn 761 9 of of IN cord-276598-tm0yj2sn 761 10 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 761 11 . . . cord-276598-tm0yj2sn 762 1 Scheme scheme NN cord-276598-tm0yj2sn 762 2 24 24 CD cord-276598-tm0yj2sn 762 3 . . . cord-276598-tm0yj2sn 763 1 Proposed propose VBN cord-276598-tm0yj2sn 763 2 mechanism mechanism NN cord-276598-tm0yj2sn 763 3 for for IN cord-276598-tm0yj2sn 763 4 the the DT cord-276598-tm0yj2sn 763 5 iodine iodine NN cord-276598-tm0yj2sn 763 6 - - HYPH cord-276598-tm0yj2sn 763 7 mediated mediate VBN cord-276598-tm0yj2sn 763 8 synthesis synthesis NN cord-276598-tm0yj2sn 763 9 of of IN cord-276598-tm0yj2sn 763 10 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 763 11 . . . cord-276598-tm0yj2sn 764 1 In in IN cord-276598-tm0yj2sn 764 2 a a DT cord-276598-tm0yj2sn 764 3 mechanism mechanism NN cord-276598-tm0yj2sn 764 4 of of IN cord-276598-tm0yj2sn 764 5 the the DT cord-276598-tm0yj2sn 764 6 I2-mediated I2-mediated NNP cord-276598-tm0yj2sn 764 7 P P NNP cord-276598-tm0yj2sn 764 8 - - HYPH cord-276598-tm0yj2sn 764 9 N N NNP cord-276598-tm0yj2sn 764 10 formation formation NN cord-276598-tm0yj2sn 764 11 , , , cord-276598-tm0yj2sn 764 12 according accord VBG cord-276598-tm0yj2sn 764 13 to to IN cord-276598-tm0yj2sn 764 14 Singh Singh NNP cord-276598-tm0yj2sn 764 15 et et NNP cord-276598-tm0yj2sn 764 16 al al NNP cord-276598-tm0yj2sn 764 17 . . NNP cord-276598-tm0yj2sn 764 18 , , , cord-276598-tm0yj2sn 764 19 H H NNP cord-276598-tm0yj2sn 764 20 - - HYPH cord-276598-tm0yj2sn 764 21 P P NNP cord-276598-tm0yj2sn 764 22 reacts react VBZ cord-276598-tm0yj2sn 764 23 with with IN cord-276598-tm0yj2sn 764 24 I2 I2 NNP cord-276598-tm0yj2sn 764 25 to to TO cord-276598-tm0yj2sn 764 26 form form VB cord-276598-tm0yj2sn 764 27 an an DT cord-276598-tm0yj2sn 764 28 intermediate intermediate JJ cord-276598-tm0yj2sn 764 29 , , , cord-276598-tm0yj2sn 764 30 which which WDT cord-276598-tm0yj2sn 764 31 undergoes undergo VBZ cord-276598-tm0yj2sn 764 32 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 764 33 attack attack NN cord-276598-tm0yj2sn 764 34 from from IN cord-276598-tm0yj2sn 764 35 the the DT cord-276598-tm0yj2sn 764 36 amine amine NN cord-276598-tm0yj2sn 764 37 to to TO cord-276598-tm0yj2sn 764 38 generate generate VB cord-276598-tm0yj2sn 764 39 a a DT cord-276598-tm0yj2sn 764 40 hydroxylated hydroxylate VBN cord-276598-tm0yj2sn 764 41 - - HYPH cord-276598-tm0yj2sn 764 42 dialkyl dialkyl NN cord-276598-tm0yj2sn 764 43 phenylphosphoramidate phenylphosphoramidate NN cord-276598-tm0yj2sn 764 44 complex complex NN cord-276598-tm0yj2sn 764 45 with with IN cord-276598-tm0yj2sn 764 46 an an DT cord-276598-tm0yj2sn 764 47 elimination elimination NN cord-276598-tm0yj2sn 764 48 of of IN cord-276598-tm0yj2sn 764 49 I2 I2 NNP cord-276598-tm0yj2sn 764 50 ( ( -LRB- cord-276598-tm0yj2sn 764 51 Scheme scheme NN cord-276598-tm0yj2sn 764 52 25 25 CD cord-276598-tm0yj2sn 764 53 ) ) -RRB- cord-276598-tm0yj2sn 764 54 [ [ -LRB- cord-276598-tm0yj2sn 764 55 101 101 CD cord-276598-tm0yj2sn 764 56 ] ] -RRB- cord-276598-tm0yj2sn 764 57 . . . cord-276598-tm0yj2sn 765 1 The the DT cord-276598-tm0yj2sn 765 2 phosphoramidate phosphoramidate NN cord-276598-tm0yj2sn 765 3 complex complex NN cord-276598-tm0yj2sn 765 4 further further RB cord-276598-tm0yj2sn 765 5 undergoes undergo VBZ cord-276598-tm0yj2sn 765 6 dehydrogenation dehydrogenation NN cord-276598-tm0yj2sn 765 7 to to TO cord-276598-tm0yj2sn 765 8 eliminate eliminate VB cord-276598-tm0yj2sn 765 9 H2 H2 NNP cord-276598-tm0yj2sn 765 10 in in IN cord-276598-tm0yj2sn 765 11 form form NN cord-276598-tm0yj2sn 765 12 of of IN cord-276598-tm0yj2sn 765 13 H2O h2o NN cord-276598-tm0yj2sn 765 14 and and CC cord-276598-tm0yj2sn 765 15 afford afford VB cord-276598-tm0yj2sn 765 16 the the DT cord-276598-tm0yj2sn 765 17 desired desire VBN cord-276598-tm0yj2sn 765 18 products product NNS cord-276598-tm0yj2sn 765 19 . . . cord-276598-tm0yj2sn 766 1 [ [ -LRB- cord-276598-tm0yj2sn 766 2 102 102 CD cord-276598-tm0yj2sn 766 3 ] ] -RRB- cord-276598-tm0yj2sn 766 4 . . . cord-276598-tm0yj2sn 767 1 Then then RB cord-276598-tm0yj2sn 767 2 , , , cord-276598-tm0yj2sn 767 3 the the DT cord-276598-tm0yj2sn 767 4 iodide iodide NN cord-276598-tm0yj2sn 767 5 ion ion NN cord-276598-tm0yj2sn 767 6 is be VBZ cord-276598-tm0yj2sn 767 7 oxidized oxidize VBN cord-276598-tm0yj2sn 767 8 to to IN cord-276598-tm0yj2sn 767 9 active active JJ cord-276598-tm0yj2sn 767 10 catalyst catalyst NN cord-276598-tm0yj2sn 767 11 , , , cord-276598-tm0yj2sn 767 12 hypoiodous hypoiodous JJ cord-276598-tm0yj2sn 767 13 acid acid NN cord-276598-tm0yj2sn 767 14 , , , cord-276598-tm0yj2sn 767 15 in in IN cord-276598-tm0yj2sn 767 16 the the DT cord-276598-tm0yj2sn 767 17 presence presence NN cord-276598-tm0yj2sn 767 18 of of IN cord-276598-tm0yj2sn 767 19 H2O2 H2O2 NNP cord-276598-tm0yj2sn 767 20 . . . cord-276598-tm0yj2sn 768 1 Scheme scheme NN cord-276598-tm0yj2sn 768 2 26 26 CD cord-276598-tm0yj2sn 768 3 . . . cord-276598-tm0yj2sn 769 1 Proposed propose VBN cord-276598-tm0yj2sn 769 2 mechanism mechanism NN cord-276598-tm0yj2sn 769 3 for for IN cord-276598-tm0yj2sn 769 4 the the DT cord-276598-tm0yj2sn 769 5 hypoiodous hypoiodous JJ cord-276598-tm0yj2sn 769 6 acid acid NN cord-276598-tm0yj2sn 769 7 - - HYPH cord-276598-tm0yj2sn 769 8 mediated mediate VBN cord-276598-tm0yj2sn 769 9 synthesis synthesis NN cord-276598-tm0yj2sn 769 10 of of IN cord-276598-tm0yj2sn 769 11 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 769 12 . . . cord-276598-tm0yj2sn 770 1 In in IN cord-276598-tm0yj2sn 770 2 a a DT cord-276598-tm0yj2sn 770 3 copper copper NN cord-276598-tm0yj2sn 770 4 - - HYPH cord-276598-tm0yj2sn 770 5 catalyzed catalyze VBN cord-276598-tm0yj2sn 770 6 oxidative oxidative JJ cord-276598-tm0yj2sn 770 7 cross cross JJ cord-276598-tm0yj2sn 770 8 - - JJ cord-276598-tm0yj2sn 770 9 coupling coupling JJ cord-276598-tm0yj2sn 770 10 reaction reaction NN cord-276598-tm0yj2sn 770 11 , , , cord-276598-tm0yj2sn 770 12 Hayes Hayes NNP cord-276598-tm0yj2sn 770 13 et et NNP cord-276598-tm0yj2sn 770 14 al al NNP cord-276598-tm0yj2sn 770 15 . . NNP cord-276598-tm0yj2sn 770 16 proposed propose VBD cord-276598-tm0yj2sn 770 17 a a DT cord-276598-tm0yj2sn 770 18 reaction reaction NN cord-276598-tm0yj2sn 770 19 mechanism mechanism NN cord-276598-tm0yj2sn 770 20 involving involve VBG cord-276598-tm0yj2sn 770 21 single single JJ cord-276598-tm0yj2sn 770 22 - - HYPH cord-276598-tm0yj2sn 770 23 electron electron NN cord-276598-tm0yj2sn 770 24 transfer transfer NN cord-276598-tm0yj2sn 770 25 oxidation oxidation NN cord-276598-tm0yj2sn 770 26 of of IN cord-276598-tm0yj2sn 770 27 the the DT cord-276598-tm0yj2sn 770 28 copper copper NN cord-276598-tm0yj2sn 770 29 catalyst catalyst NN cord-276598-tm0yj2sn 770 30 , , , cord-276598-tm0yj2sn 770 31 which which WDT cord-276598-tm0yj2sn 770 32 favored favor VBD cord-276598-tm0yj2sn 770 33 the the DT cord-276598-tm0yj2sn 770 34 formation formation NN cord-276598-tm0yj2sn 770 35 of of IN cord-276598-tm0yj2sn 770 36 the the DT cord-276598-tm0yj2sn 770 37 Cu(II)-amine Cu(II)-amine NNP cord-276598-tm0yj2sn 770 38 complex complex NN cord-276598-tm0yj2sn 770 39 ( ( -LRB- cord-276598-tm0yj2sn 770 40 Scheme scheme NN cord-276598-tm0yj2sn 770 41 27 27 CD cord-276598-tm0yj2sn 770 42 ) ) -RRB- cord-276598-tm0yj2sn 770 43 [ [ -LRB- cord-276598-tm0yj2sn 770 44 103 103 CD cord-276598-tm0yj2sn 770 45 ] ] -RRB- cord-276598-tm0yj2sn 770 46 . . . cord-276598-tm0yj2sn 771 1 The the DT cord-276598-tm0yj2sn 771 2 Cu(II)-amine Cu(II)-amine NNP cord-276598-tm0yj2sn 771 3 complex complex NN cord-276598-tm0yj2sn 771 4 is be VBZ cord-276598-tm0yj2sn 771 5 further further JJ cord-276598-tm0yj2sn 771 6 Scheme scheme NN cord-276598-tm0yj2sn 771 7 26 26 CD cord-276598-tm0yj2sn 771 8 . . . cord-276598-tm0yj2sn 772 1 Proposed propose VBN cord-276598-tm0yj2sn 772 2 mechanism mechanism NN cord-276598-tm0yj2sn 772 3 for for IN cord-276598-tm0yj2sn 772 4 the the DT cord-276598-tm0yj2sn 772 5 hypoiodous hypoiodous JJ cord-276598-tm0yj2sn 772 6 acid acid NN cord-276598-tm0yj2sn 772 7 - - HYPH cord-276598-tm0yj2sn 772 8 mediated mediate VBN cord-276598-tm0yj2sn 772 9 synthesis synthesis NN cord-276598-tm0yj2sn 772 10 of of IN cord-276598-tm0yj2sn 772 11 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 772 12 . . . cord-276598-tm0yj2sn 773 1 In in IN cord-276598-tm0yj2sn 773 2 a a DT cord-276598-tm0yj2sn 773 3 copper copper NN cord-276598-tm0yj2sn 773 4 - - HYPH cord-276598-tm0yj2sn 773 5 catalyzed catalyze VBN cord-276598-tm0yj2sn 773 6 oxidative oxidative JJ cord-276598-tm0yj2sn 773 7 cross cross JJ cord-276598-tm0yj2sn 773 8 - - JJ cord-276598-tm0yj2sn 773 9 coupling coupling JJ cord-276598-tm0yj2sn 773 10 reaction reaction NN cord-276598-tm0yj2sn 773 11 , , , cord-276598-tm0yj2sn 773 12 Hayes Hayes NNP cord-276598-tm0yj2sn 773 13 et et NNP cord-276598-tm0yj2sn 773 14 al al NNP cord-276598-tm0yj2sn 773 15 . . NNP cord-276598-tm0yj2sn 773 16 proposed propose VBD cord-276598-tm0yj2sn 773 17 a a DT cord-276598-tm0yj2sn 773 18 reaction reaction NN cord-276598-tm0yj2sn 773 19 mechanism mechanism NN cord-276598-tm0yj2sn 773 20 involving involve VBG cord-276598-tm0yj2sn 773 21 single single JJ cord-276598-tm0yj2sn 773 22 - - HYPH cord-276598-tm0yj2sn 773 23 electron electron NN cord-276598-tm0yj2sn 773 24 transfer transfer NN cord-276598-tm0yj2sn 773 25 oxidation oxidation NN cord-276598-tm0yj2sn 773 26 of of IN cord-276598-tm0yj2sn 773 27 the the DT cord-276598-tm0yj2sn 773 28 copper copper NN cord-276598-tm0yj2sn 773 29 catalyst catalyst NN cord-276598-tm0yj2sn 773 30 , , , cord-276598-tm0yj2sn 773 31 which which WDT cord-276598-tm0yj2sn 773 32 favored favor VBD cord-276598-tm0yj2sn 773 33 the the DT cord-276598-tm0yj2sn 773 34 formation formation NN cord-276598-tm0yj2sn 773 35 of of IN cord-276598-tm0yj2sn 773 36 the the DT cord-276598-tm0yj2sn 773 37 Cu(II)-amine Cu(II)-amine NNP cord-276598-tm0yj2sn 773 38 complex complex NN cord-276598-tm0yj2sn 773 39 ( ( -LRB- cord-276598-tm0yj2sn 773 40 Scheme scheme NN cord-276598-tm0yj2sn 773 41 27 27 CD cord-276598-tm0yj2sn 773 42 ) ) -RRB- cord-276598-tm0yj2sn 773 43 [ [ -LRB- cord-276598-tm0yj2sn 773 44 103 103 CD cord-276598-tm0yj2sn 773 45 ] ] -RRB- cord-276598-tm0yj2sn 773 46 . . . cord-276598-tm0yj2sn 774 1 The the DT cord-276598-tm0yj2sn 774 2 Cu(II)-amine Cu(II)-amine NNP cord-276598-tm0yj2sn 774 3 complex complex NN cord-276598-tm0yj2sn 774 4 is be VBZ cord-276598-tm0yj2sn 774 5 further further RB cord-276598-tm0yj2sn 774 6 oxidized oxidize VBN cord-276598-tm0yj2sn 774 7 to to TO cord-276598-tm0yj2sn 774 8 form form VB cord-276598-tm0yj2sn 774 9 the the DT cord-276598-tm0yj2sn 774 10 Cu(III)-amine Cu(III)-amine NNP cord-276598-tm0yj2sn 774 11 - - HYPH cord-276598-tm0yj2sn 774 12 phosphonate phosphonate JJ cord-276598-tm0yj2sn 774 13 complex complex NN cord-276598-tm0yj2sn 774 14 , , , cord-276598-tm0yj2sn 774 15 which which WDT cord-276598-tm0yj2sn 774 16 undergoes undergo VBZ cord-276598-tm0yj2sn 774 17 reductive reductive JJ cord-276598-tm0yj2sn 774 18 elimination elimination NN cord-276598-tm0yj2sn 774 19 of of IN cord-276598-tm0yj2sn 774 20 the the DT cord-276598-tm0yj2sn 774 21 copper copper NN cord-276598-tm0yj2sn 774 22 catalyst catalyst NN cord-276598-tm0yj2sn 774 23 to to TO cord-276598-tm0yj2sn 774 24 yield yield VB cord-276598-tm0yj2sn 774 25 the the DT cord-276598-tm0yj2sn 774 26 desired desire VBN cord-276598-tm0yj2sn 774 27 P p NN cord-276598-tm0yj2sn 774 28 - - HYPH cord-276598-tm0yj2sn 774 29 N. n. NN cord-276598-tm0yj2sn 775 1 Although although IN cord-276598-tm0yj2sn 775 2 this this DT cord-276598-tm0yj2sn 775 3 mechanism mechanism NN cord-276598-tm0yj2sn 775 4 seems seem VBZ cord-276598-tm0yj2sn 775 5 plausible plausible JJ cord-276598-tm0yj2sn 775 6 , , , cord-276598-tm0yj2sn 775 7 it -PRON- PRP cord-276598-tm0yj2sn 775 8 could could MD cord-276598-tm0yj2sn 775 9 not not RB cord-276598-tm0yj2sn 775 10 easily easily RB cord-276598-tm0yj2sn 775 11 explain explain VB cord-276598-tm0yj2sn 775 12 the the DT cord-276598-tm0yj2sn 775 13 formation formation NN cord-276598-tm0yj2sn 775 14 of of IN cord-276598-tm0yj2sn 775 15 the the DT cord-276598-tm0yj2sn 775 16 side side NN cord-276598-tm0yj2sn 775 17 products product NNS cord-276598-tm0yj2sn 775 18 . . . cord-276598-tm0yj2sn 776 1 Molecules molecule NNS cord-276598-tm0yj2sn 776 2 2020 2020 CD cord-276598-tm0yj2sn 776 3 , , , cord-276598-tm0yj2sn 776 4 25 25 CD cord-276598-tm0yj2sn 776 5 , , , cord-276598-tm0yj2sn 776 6 x x NN cord-276598-tm0yj2sn 776 7 FOR for IN cord-276598-tm0yj2sn 776 8 PEER peer NN cord-276598-tm0yj2sn 776 9 REVIEW REVIEW NNP cord-276598-tm0yj2sn 776 10 23 23 CD cord-276598-tm0yj2sn 776 11 of of IN cord-276598-tm0yj2sn 776 12 37 37 CD cord-276598-tm0yj2sn 776 13 oxidized oxidize VBN cord-276598-tm0yj2sn 776 14 to to TO cord-276598-tm0yj2sn 776 15 form form VB cord-276598-tm0yj2sn 776 16 the the DT cord-276598-tm0yj2sn 776 17 Cu(III)-amine Cu(III)-amine NNP cord-276598-tm0yj2sn 776 18 - - HYPH cord-276598-tm0yj2sn 776 19 phosphonate phosphonate JJ cord-276598-tm0yj2sn 776 20 complex complex NN cord-276598-tm0yj2sn 776 21 , , , cord-276598-tm0yj2sn 776 22 which which WDT cord-276598-tm0yj2sn 776 23 undergoes undergo VBZ cord-276598-tm0yj2sn 776 24 reductive reductive JJ cord-276598-tm0yj2sn 776 25 elimination elimination NN cord-276598-tm0yj2sn 776 26 of of IN cord-276598-tm0yj2sn 776 27 the the DT cord-276598-tm0yj2sn 776 28 copper copper NN cord-276598-tm0yj2sn 776 29 catalyst catalyst NN cord-276598-tm0yj2sn 776 30 to to TO cord-276598-tm0yj2sn 776 31 yield yield VB cord-276598-tm0yj2sn 776 32 the the DT cord-276598-tm0yj2sn 776 33 desired desire VBN cord-276598-tm0yj2sn 776 34 P p NN cord-276598-tm0yj2sn 776 35 - - HYPH cord-276598-tm0yj2sn 776 36 N. n. NN cord-276598-tm0yj2sn 777 1 Although although IN cord-276598-tm0yj2sn 777 2 this this DT cord-276598-tm0yj2sn 777 3 mechanism mechanism NN cord-276598-tm0yj2sn 777 4 seems seem VBZ cord-276598-tm0yj2sn 777 5 plausible plausible JJ cord-276598-tm0yj2sn 777 6 , , , cord-276598-tm0yj2sn 777 7 it -PRON- PRP cord-276598-tm0yj2sn 777 8 could could MD cord-276598-tm0yj2sn 777 9 not not RB cord-276598-tm0yj2sn 777 10 easily easily RB cord-276598-tm0yj2sn 777 11 explain explain VB cord-276598-tm0yj2sn 777 12 the the DT cord-276598-tm0yj2sn 777 13 formation formation NN cord-276598-tm0yj2sn 777 14 of of IN cord-276598-tm0yj2sn 777 15 the the DT cord-276598-tm0yj2sn 777 16 side side NN cord-276598-tm0yj2sn 777 17 products product NNS cord-276598-tm0yj2sn 777 18 . . . cord-276598-tm0yj2sn 778 1 According accord VBG cord-276598-tm0yj2sn 778 2 the the DT cord-276598-tm0yj2sn 778 3 plausible plausible JJ cord-276598-tm0yj2sn 778 4 two two CD cord-276598-tm0yj2sn 778 5 - - HYPH cord-276598-tm0yj2sn 778 6 step step NN cord-276598-tm0yj2sn 778 7 mechanism mechanism NN cord-276598-tm0yj2sn 778 8 for for IN cord-276598-tm0yj2sn 778 9 the the DT cord-276598-tm0yj2sn 778 10 reaction reaction NN cord-276598-tm0yj2sn 778 11 by by IN cord-276598-tm0yj2sn 778 12 Purohit Purohit NNP cord-276598-tm0yj2sn 778 13 et et NNP cord-276598-tm0yj2sn 778 14 al al NNP cord-276598-tm0yj2sn 778 15 . . NNP cord-276598-tm0yj2sn 778 16 , , , cord-276598-tm0yj2sn 778 17 ( ( -LRB- cord-276598-tm0yj2sn 778 18 RO RO NNP cord-276598-tm0yj2sn 778 19 ) ) -RRB- cord-276598-tm0yj2sn 778 20 2 2 CD cord-276598-tm0yj2sn 778 21 P(O)Cl p(o)cl NN cord-276598-tm0yj2sn 778 22 ( ( -LRB- cord-276598-tm0yj2sn 778 23 dACP dACP . cord-276598-tm0yj2sn 779 1 ; ; : cord-276598-tm0yj2sn 779 2 R r NN cord-276598-tm0yj2sn 779 3 = = NN cord-276598-tm0yj2sn 779 4 alkyl alkyl NN cord-276598-tm0yj2sn 779 5 ) ) -RRB- cord-276598-tm0yj2sn 779 6 is be VBZ cord-276598-tm0yj2sn 779 7 first first RB cord-276598-tm0yj2sn 779 8 generated generate VBN cord-276598-tm0yj2sn 779 9 from from IN cord-276598-tm0yj2sn 779 10 the the DT cord-276598-tm0yj2sn 779 11 electrophilic electrophilic JJ cord-276598-tm0yj2sn 779 12 displacement displacement NN cord-276598-tm0yj2sn 779 13 of of IN cord-276598-tm0yj2sn 779 14 hydrogen hydrogen NN cord-276598-tm0yj2sn 779 15 on on IN cord-276598-tm0yj2sn 779 16 the the DT cord-276598-tm0yj2sn 779 17 dialkyl dialkyl NN cord-276598-tm0yj2sn 779 18 H H NNP cord-276598-tm0yj2sn 779 19 - - HYPH cord-276598-tm0yj2sn 779 20 phosphonate phosphonate NNP cord-276598-tm0yj2sn 779 21 ( ( -LRB- cord-276598-tm0yj2sn 779 22 ( ( -LRB- cord-276598-tm0yj2sn 779 23 OR or NN cord-276598-tm0yj2sn 779 24 ) ) -RRB- cord-276598-tm0yj2sn 780 1 2 2 LS cord-276598-tm0yj2sn 781 1 P(O)H p(o)h NN cord-276598-tm0yj2sn 781 2 , , , cord-276598-tm0yj2sn 781 3 R r NN cord-276598-tm0yj2sn 781 4 = = NN cord-276598-tm0yj2sn 781 5 alkyl alkyl NN cord-276598-tm0yj2sn 781 6 ) ) -RRB- cord-276598-tm0yj2sn 781 7 upon upon IN cord-276598-tm0yj2sn 781 8 reacting react VBG cord-276598-tm0yj2sn 781 9 with with IN cord-276598-tm0yj2sn 781 10 CuCl CuCl NNP cord-276598-tm0yj2sn 781 11 2 2 CD cord-276598-tm0yj2sn 781 12 ( ( -LRB- cord-276598-tm0yj2sn 781 13 Scheme scheme NN cord-276598-tm0yj2sn 781 14 29a 29a NNS cord-276598-tm0yj2sn 781 15 ) ) -RRB- cord-276598-tm0yj2sn 782 1 [ [ -LRB- cord-276598-tm0yj2sn 782 2 106 106 CD cord-276598-tm0yj2sn 782 3 ] ] -RRB- cord-276598-tm0yj2sn 782 4 . . . cord-276598-tm0yj2sn 783 1 The the DT cord-276598-tm0yj2sn 783 2 phosphoramidate phosphoramidate NN cord-276598-tm0yj2sn 783 3 is be VBZ cord-276598-tm0yj2sn 783 4 formed form VBN cord-276598-tm0yj2sn 783 5 in in IN cord-276598-tm0yj2sn 783 6 the the DT cord-276598-tm0yj2sn 783 7 second second JJ cord-276598-tm0yj2sn 783 8 step step NN cord-276598-tm0yj2sn 783 9 by by IN cord-276598-tm0yj2sn 783 10 coupling couple VBG cord-276598-tm0yj2sn 783 11 dACP dacp NN cord-276598-tm0yj2sn 783 12 and and CC cord-276598-tm0yj2sn 783 13 amine amine NN cord-276598-tm0yj2sn 783 14 . . . cord-276598-tm0yj2sn 784 1 However however RB cord-276598-tm0yj2sn 784 2 , , , cord-276598-tm0yj2sn 784 3 this this DT cord-276598-tm0yj2sn 784 4 reported report VBN cord-276598-tm0yj2sn 784 5 mechanism mechanism NN cord-276598-tm0yj2sn 784 6 could could MD cord-276598-tm0yj2sn 784 7 not not RB cord-276598-tm0yj2sn 784 8 properly properly RB cord-276598-tm0yj2sn 784 9 explain explain VB cord-276598-tm0yj2sn 784 10 the the DT cord-276598-tm0yj2sn 784 11 role role NN cord-276598-tm0yj2sn 784 12 of of IN cord-276598-tm0yj2sn 784 13 Cs Cs NNP cord-276598-tm0yj2sn 784 14 2 2 CD cord-276598-tm0yj2sn 784 15 CO CO NNP cord-276598-tm0yj2sn 784 16 3 3 CD cord-276598-tm0yj2sn 784 17 in in IN cord-276598-tm0yj2sn 784 18 the the DT cord-276598-tm0yj2sn 784 19 coupling coupling NN cord-276598-tm0yj2sn 784 20 of of IN cord-276598-tm0yj2sn 784 21 alkyl alkyl NNP cord-276598-tm0yj2sn 784 22 chlorophosphate chlorophosphate NN cord-276598-tm0yj2sn 784 23 and and CC cord-276598-tm0yj2sn 784 24 the the DT cord-276598-tm0yj2sn 784 25 amine amine NN cord-276598-tm0yj2sn 784 26 to to TO cord-276598-tm0yj2sn 784 27 give give VB cord-276598-tm0yj2sn 784 28 the the DT cord-276598-tm0yj2sn 784 29 P p NN cord-276598-tm0yj2sn 784 30 - - HYPH cord-276598-tm0yj2sn 784 31 N. n. NN cord-276598-tm0yj2sn 785 1 This this DT cord-276598-tm0yj2sn 785 2 is be VBZ cord-276598-tm0yj2sn 785 3 because because IN cord-276598-tm0yj2sn 785 4 the the DT cord-276598-tm0yj2sn 785 5 coupling coupling NN cord-276598-tm0yj2sn 785 6 reaction reaction NN cord-276598-tm0yj2sn 785 7 was be VBD cord-276598-tm0yj2sn 785 8 expected expect VBN cord-276598-tm0yj2sn 785 9 to to TO cord-276598-tm0yj2sn 785 10 eliminate eliminate VB cord-276598-tm0yj2sn 785 11 other other JJ cord-276598-tm0yj2sn 785 12 products product NNS cord-276598-tm0yj2sn 785 13 along along IN cord-276598-tm0yj2sn 785 14 with with IN cord-276598-tm0yj2sn 785 15 CsCl CsCl NNP cord-276598-tm0yj2sn 785 16 such such JJ cord-276598-tm0yj2sn 785 17 as as IN cord-276598-tm0yj2sn 785 18 a a DT cord-276598-tm0yj2sn 785 19 highly highly RB cord-276598-tm0yj2sn 785 20 reactive reactive JJ cord-276598-tm0yj2sn 785 21 CsH csh NN cord-276598-tm0yj2sn 785 22 and and CC cord-276598-tm0yj2sn 785 23 a a DT cord-276598-tm0yj2sn 785 24 carbonate carbonate NN cord-276598-tm0yj2sn 785 25 . . . cord-276598-tm0yj2sn 786 1 However however RB cord-276598-tm0yj2sn 786 2 , , , cord-276598-tm0yj2sn 786 3 it -PRON- PRP cord-276598-tm0yj2sn 786 4 is be VBZ cord-276598-tm0yj2sn 786 5 to to TO cord-276598-tm0yj2sn 786 6 be be VB cord-276598-tm0yj2sn 786 7 understood understand VBN cord-276598-tm0yj2sn 786 8 that that IN cord-276598-tm0yj2sn 786 9 the the DT cord-276598-tm0yj2sn 786 10 use use NN cord-276598-tm0yj2sn 786 11 of of IN cord-276598-tm0yj2sn 786 12 Cs Cs NNP cord-276598-tm0yj2sn 786 13 2 2 CD cord-276598-tm0yj2sn 786 14 CO CO NNP cord-276598-tm0yj2sn 786 15 3 3 CD cord-276598-tm0yj2sn 786 16 as as IN cord-276598-tm0yj2sn 786 17 the the DT cord-276598-tm0yj2sn 786 18 inorganic inorganic JJ cord-276598-tm0yj2sn 786 19 base base NN cord-276598-tm0yj2sn 786 20 was be VBD cord-276598-tm0yj2sn 786 21 based base VBN cord-276598-tm0yj2sn 786 22 on on IN cord-276598-tm0yj2sn 786 23 the the DT cord-276598-tm0yj2sn 786 24 poorly poorly RB cord-276598-tm0yj2sn 786 25 understood understand VBN cord-276598-tm0yj2sn 786 26 " " `` cord-276598-tm0yj2sn 786 27 caesium caesium NN cord-276598-tm0yj2sn 786 28 effect effect NN cord-276598-tm0yj2sn 786 29 " " '' cord-276598-tm0yj2sn 786 30 in in IN cord-276598-tm0yj2sn 786 31 which which WDT cord-276598-tm0yj2sn 786 32 the the DT cord-276598-tm0yj2sn 786 33 highly highly RB cord-276598-tm0yj2sn 786 34 soluble soluble JJ cord-276598-tm0yj2sn 786 35 caesium caesium NN cord-276598-tm0yj2sn 786 36 base base NN cord-276598-tm0yj2sn 786 37 selectively selectively RB cord-276598-tm0yj2sn 786 38 favors favor VBZ cord-276598-tm0yj2sn 786 39 the the DT cord-276598-tm0yj2sn 786 40 formation formation NN cord-276598-tm0yj2sn 786 41 of of IN cord-276598-tm0yj2sn 786 42 one one CD cord-276598-tm0yj2sn 786 43 functional functional JJ cord-276598-tm0yj2sn 786 44 group group NN cord-276598-tm0yj2sn 786 45 in in IN cord-276598-tm0yj2sn 786 46 preference preference NN cord-276598-tm0yj2sn 786 47 to to IN cord-276598-tm0yj2sn 786 48 another another DT cord-276598-tm0yj2sn 786 49 [ [ -LRB- cord-276598-tm0yj2sn 786 50 122 122 CD cord-276598-tm0yj2sn 786 51 , , , cord-276598-tm0yj2sn 786 52 123 123 CD cord-276598-tm0yj2sn 786 53 ] ] -RRB- cord-276598-tm0yj2sn 786 54 . . . cord-276598-tm0yj2sn 787 1 Molecules molecule NNS cord-276598-tm0yj2sn 787 2 2020 2020 CD cord-276598-tm0yj2sn 787 3 , , , cord-276598-tm0yj2sn 787 4 25 25 CD cord-276598-tm0yj2sn 787 5 , , , cord-276598-tm0yj2sn 787 6 x x NN cord-276598-tm0yj2sn 787 7 FOR for IN cord-276598-tm0yj2sn 787 8 PEER PEER NNP cord-276598-tm0yj2sn 787 9 REVIEW REVIEW NNP cord-276598-tm0yj2sn 787 10 24 24 CD cord-276598-tm0yj2sn 787 11 of of IN cord-276598-tm0yj2sn 787 12 37 37 CD cord-276598-tm0yj2sn 787 13 phosphoramidate phosphoramidate NN cord-276598-tm0yj2sn 787 14 is be VBZ cord-276598-tm0yj2sn 787 15 formed form VBN cord-276598-tm0yj2sn 787 16 in in IN cord-276598-tm0yj2sn 787 17 the the DT cord-276598-tm0yj2sn 787 18 second second JJ cord-276598-tm0yj2sn 787 19 step step NN cord-276598-tm0yj2sn 787 20 by by IN cord-276598-tm0yj2sn 787 21 coupling couple VBG cord-276598-tm0yj2sn 787 22 dACP dacp NN cord-276598-tm0yj2sn 787 23 and and CC cord-276598-tm0yj2sn 787 24 amine amine NN cord-276598-tm0yj2sn 787 25 . . . cord-276598-tm0yj2sn 788 1 However however RB cord-276598-tm0yj2sn 788 2 , , , cord-276598-tm0yj2sn 788 3 this this DT cord-276598-tm0yj2sn 788 4 reported report VBN cord-276598-tm0yj2sn 788 5 mechanism mechanism NN cord-276598-tm0yj2sn 788 6 could could MD cord-276598-tm0yj2sn 788 7 not not RB cord-276598-tm0yj2sn 788 8 properly properly RB cord-276598-tm0yj2sn 788 9 explain explain VB cord-276598-tm0yj2sn 788 10 the the DT cord-276598-tm0yj2sn 788 11 role role NN cord-276598-tm0yj2sn 788 12 of of IN cord-276598-tm0yj2sn 788 13 Cs2CO3 Cs2CO3 NNP cord-276598-tm0yj2sn 788 14 in in IN cord-276598-tm0yj2sn 788 15 the the DT cord-276598-tm0yj2sn 788 16 coupling coupling NN cord-276598-tm0yj2sn 788 17 of of IN cord-276598-tm0yj2sn 788 18 alkyl alkyl NNP cord-276598-tm0yj2sn 788 19 chlorophosphate chlorophosphate NN cord-276598-tm0yj2sn 788 20 and and CC cord-276598-tm0yj2sn 788 21 the the DT cord-276598-tm0yj2sn 788 22 amine amine NN cord-276598-tm0yj2sn 788 23 to to TO cord-276598-tm0yj2sn 788 24 give give VB cord-276598-tm0yj2sn 788 25 the the DT cord-276598-tm0yj2sn 788 26 P p NN cord-276598-tm0yj2sn 788 27 - - HYPH cord-276598-tm0yj2sn 788 28 N. n. NN cord-276598-tm0yj2sn 789 1 This this DT cord-276598-tm0yj2sn 789 2 is be VBZ cord-276598-tm0yj2sn 789 3 because because IN cord-276598-tm0yj2sn 789 4 the the DT cord-276598-tm0yj2sn 789 5 coupling coupling NN cord-276598-tm0yj2sn 789 6 reaction reaction NN cord-276598-tm0yj2sn 789 7 was be VBD cord-276598-tm0yj2sn 789 8 expected expect VBN cord-276598-tm0yj2sn 789 9 to to TO cord-276598-tm0yj2sn 789 10 eliminate eliminate VB cord-276598-tm0yj2sn 789 11 other other JJ cord-276598-tm0yj2sn 789 12 products product NNS cord-276598-tm0yj2sn 789 13 along along IN cord-276598-tm0yj2sn 789 14 with with IN cord-276598-tm0yj2sn 789 15 CsCl CsCl NNP cord-276598-tm0yj2sn 789 16 such such JJ cord-276598-tm0yj2sn 789 17 as as IN cord-276598-tm0yj2sn 789 18 a a DT cord-276598-tm0yj2sn 789 19 highly highly RB cord-276598-tm0yj2sn 789 20 reactive reactive JJ cord-276598-tm0yj2sn 789 21 CsH csh NN cord-276598-tm0yj2sn 789 22 and and CC cord-276598-tm0yj2sn 789 23 a a DT cord-276598-tm0yj2sn 789 24 carbonate carbonate NN cord-276598-tm0yj2sn 789 25 . . . cord-276598-tm0yj2sn 790 1 However however RB cord-276598-tm0yj2sn 790 2 , , , cord-276598-tm0yj2sn 790 3 it -PRON- PRP cord-276598-tm0yj2sn 790 4 is be VBZ cord-276598-tm0yj2sn 790 5 to to TO cord-276598-tm0yj2sn 790 6 be be VB cord-276598-tm0yj2sn 790 7 understood understand VBN cord-276598-tm0yj2sn 790 8 that that IN cord-276598-tm0yj2sn 790 9 the the DT cord-276598-tm0yj2sn 790 10 use use NN cord-276598-tm0yj2sn 790 11 of of IN cord-276598-tm0yj2sn 790 12 Cs2CO3 Cs2CO3 NNP cord-276598-tm0yj2sn 790 13 as as IN cord-276598-tm0yj2sn 790 14 the the DT cord-276598-tm0yj2sn 790 15 inorganic inorganic JJ cord-276598-tm0yj2sn 790 16 base base NN cord-276598-tm0yj2sn 790 17 was be VBD cord-276598-tm0yj2sn 790 18 based base VBN cord-276598-tm0yj2sn 790 19 on on IN cord-276598-tm0yj2sn 790 20 the the DT cord-276598-tm0yj2sn 790 21 poorly poorly RB cord-276598-tm0yj2sn 790 22 understood understand VBN cord-276598-tm0yj2sn 790 23 " " `` cord-276598-tm0yj2sn 790 24 caesium caesium NN cord-276598-tm0yj2sn 790 25 effect effect NN cord-276598-tm0yj2sn 790 26 " " '' cord-276598-tm0yj2sn 790 27 in in IN cord-276598-tm0yj2sn 790 28 which which WDT cord-276598-tm0yj2sn 790 29 the the DT cord-276598-tm0yj2sn 790 30 highly highly RB cord-276598-tm0yj2sn 790 31 soluble soluble JJ cord-276598-tm0yj2sn 790 32 caesium caesium NN cord-276598-tm0yj2sn 790 33 base base NN cord-276598-tm0yj2sn 790 34 selectively selectively RB cord-276598-tm0yj2sn 790 35 favors favor VBZ cord-276598-tm0yj2sn 790 36 the the DT cord-276598-tm0yj2sn 790 37 formation formation NN cord-276598-tm0yj2sn 790 38 of of IN cord-276598-tm0yj2sn 790 39 one one CD cord-276598-tm0yj2sn 790 40 functional functional JJ cord-276598-tm0yj2sn 790 41 group group NN cord-276598-tm0yj2sn 790 42 in in IN cord-276598-tm0yj2sn 790 43 preference preference NN cord-276598-tm0yj2sn 790 44 to to IN cord-276598-tm0yj2sn 790 45 another another DT cord-276598-tm0yj2sn 790 46 [ [ -LRB- cord-276598-tm0yj2sn 790 47 122 122 CD cord-276598-tm0yj2sn 790 48 , , , cord-276598-tm0yj2sn 790 49 123 123 CD cord-276598-tm0yj2sn 790 50 ] ] -RRB- cord-276598-tm0yj2sn 790 51 . . . cord-276598-tm0yj2sn 791 1 Proposed propose VBN cord-276598-tm0yj2sn 791 2 mechanism mechanism NN cord-276598-tm0yj2sn 791 3 for for IN cord-276598-tm0yj2sn 791 4 the the DT cord-276598-tm0yj2sn 791 5 Cu cu NN cord-276598-tm0yj2sn 791 6 - - HYPH cord-276598-tm0yj2sn 791 7 mediated mediate VBN cord-276598-tm0yj2sn 791 8 synthesis synthesis NN cord-276598-tm0yj2sn 791 9 of of IN cord-276598-tm0yj2sn 791 10 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 791 11 . . . cord-276598-tm0yj2sn 792 1 Mizuno Mizuno NNP cord-276598-tm0yj2sn 792 2 et et NNP cord-276598-tm0yj2sn 792 3 al al NNP cord-276598-tm0yj2sn 792 4 . . . cord-276598-tm0yj2sn 793 1 proposed propose VBD cord-276598-tm0yj2sn 793 2 a a DT cord-276598-tm0yj2sn 793 3 mechanism mechanism NN cord-276598-tm0yj2sn 793 4 for for IN cord-276598-tm0yj2sn 793 5 the the DT cord-276598-tm0yj2sn 793 6 reaction reaction NN cord-276598-tm0yj2sn 793 7 in in IN cord-276598-tm0yj2sn 793 8 which which WDT cord-276598-tm0yj2sn 793 9 K2CO3 K2CO3 NNP cord-276598-tm0yj2sn 793 10 first first JJ cord-276598-tm0yj2sn 793 11 deprotonates deprotonate VBZ cord-276598-tm0yj2sn 793 12 the the DT cord-276598-tm0yj2sn 793 13 amide amide NN cord-276598-tm0yj2sn 793 14 , , , cord-276598-tm0yj2sn 793 15 affording afford VBG cord-276598-tm0yj2sn 793 16 unpaired unpaired JJ cord-276598-tm0yj2sn 793 17 electrons electron NNS cord-276598-tm0yj2sn 793 18 on on IN cord-276598-tm0yj2sn 793 19 a a DT cord-276598-tm0yj2sn 793 20 Cu cu NN cord-276598-tm0yj2sn 793 21 - - NN cord-276598-tm0yj2sn 793 22 amide amide NN cord-276598-tm0yj2sn 793 23 complex complex NN cord-276598-tm0yj2sn 793 24 [ [ -LRB- cord-276598-tm0yj2sn 793 25 107 107 CD cord-276598-tm0yj2sn 793 26 ] ] -RRB- cord-276598-tm0yj2sn 793 27 . . . cord-276598-tm0yj2sn 794 1 Furthermore furthermore RB cord-276598-tm0yj2sn 794 2 , , , cord-276598-tm0yj2sn 794 3 it -PRON- PRP cord-276598-tm0yj2sn 794 4 was be VBD cord-276598-tm0yj2sn 794 5 suggested suggest VBN cord-276598-tm0yj2sn 794 6 that that IN cord-276598-tm0yj2sn 794 7 it -PRON- PRP cord-276598-tm0yj2sn 794 8 is be VBZ cord-276598-tm0yj2sn 794 9 possible possible JJ cord-276598-tm0yj2sn 794 10 that that IN cord-276598-tm0yj2sn 794 11 K2CO3 K2CO3 NNP cord-276598-tm0yj2sn 794 12 deprotonates deprotonate NNS cord-276598-tm0yj2sn 794 13 H H NNP cord-276598-tm0yj2sn 794 14 - - HYPH cord-276598-tm0yj2sn 794 15 P P NNP cord-276598-tm0yj2sn 794 16 or or CC cord-276598-tm0yj2sn 794 17 provides provide VBZ cord-276598-tm0yj2sn 794 18 a a DT cord-276598-tm0yj2sn 794 19 medium medium NN cord-276598-tm0yj2sn 794 20 for for IN cord-276598-tm0yj2sn 794 21 the the DT cord-276598-tm0yj2sn 794 22 H H NNP cord-276598-tm0yj2sn 794 23 - - HYPH cord-276598-tm0yj2sn 794 24 P p NN cord-276598-tm0yj2sn 794 25 tautomer tautomer NN cord-276598-tm0yj2sn 794 26 to to IN cord-276598-tm0yj2sn 794 27 further further RB cord-276598-tm0yj2sn 794 28 complex complex JJ cord-276598-tm0yj2sn 794 29 with with IN cord-276598-tm0yj2sn 794 30 the the DT cord-276598-tm0yj2sn 794 31 Cu cu NN cord-276598-tm0yj2sn 794 32 - - HYPH cord-276598-tm0yj2sn 794 33 amide amide NN cord-276598-tm0yj2sn 794 34 complex complex NN cord-276598-tm0yj2sn 794 35 . . . cord-276598-tm0yj2sn 795 1 The the DT cord-276598-tm0yj2sn 795 2 Cu cu NN cord-276598-tm0yj2sn 795 3 - - HYPH cord-276598-tm0yj2sn 795 4 amide amide NN cord-276598-tm0yj2sn 795 5 - - HYPH cord-276598-tm0yj2sn 795 6 phosphite phosphite NN cord-276598-tm0yj2sn 795 7 intermediate intermediate NN cord-276598-tm0yj2sn 795 8 undergoes undergo VBZ cord-276598-tm0yj2sn 795 9 reductive reductive JJ cord-276598-tm0yj2sn 795 10 elimination elimination NN cord-276598-tm0yj2sn 795 11 to to TO cord-276598-tm0yj2sn 795 12 afford afford VB cord-276598-tm0yj2sn 795 13 the the DT cord-276598-tm0yj2sn 795 14 desired desire VBN cord-276598-tm0yj2sn 795 15 product product NN cord-276598-tm0yj2sn 795 16 , , , cord-276598-tm0yj2sn 795 17 while while IN cord-276598-tm0yj2sn 795 18 O2 O2 NNP cord-276598-tm0yj2sn 795 19 re re NNS cord-276598-tm0yj2sn 795 20 - - NN cord-276598-tm0yj2sn 795 21 oxidizes oxidize VBZ cord-276598-tm0yj2sn 795 22 the the DT cord-276598-tm0yj2sn 795 23 reduced reduce VBN cord-276598-tm0yj2sn 795 24 Cu Cu NNP cord-276598-tm0yj2sn 795 25 species specie NNS cord-276598-tm0yj2sn 795 26 to to TO cord-276598-tm0yj2sn 795 27 regenerate regenerate VB cord-276598-tm0yj2sn 795 28 the the DT cord-276598-tm0yj2sn 795 29 active active JJ cord-276598-tm0yj2sn 795 30 catalyst catalyst NN cord-276598-tm0yj2sn 795 31 . . . cord-276598-tm0yj2sn 796 1 Although although IN cord-276598-tm0yj2sn 796 2 the the DT cord-276598-tm0yj2sn 796 3 oxidation oxidation NN cord-276598-tm0yj2sn 796 4 state state NN cord-276598-tm0yj2sn 796 5 of of IN cord-276598-tm0yj2sn 796 6 Cu Cu NNP cord-276598-tm0yj2sn 796 7 in in IN cord-276598-tm0yj2sn 796 8 the the DT cord-276598-tm0yj2sn 796 9 reaction reaction NN cord-276598-tm0yj2sn 796 10 mechanism mechanism NN cord-276598-tm0yj2sn 796 11 was be VBD cord-276598-tm0yj2sn 796 12 not not RB cord-276598-tm0yj2sn 796 13 explained explain VBN cord-276598-tm0yj2sn 796 14 , , , cord-276598-tm0yj2sn 796 15 the the DT cord-276598-tm0yj2sn 796 16 authors author NNS cord-276598-tm0yj2sn 796 17 suggested suggest VBD cord-276598-tm0yj2sn 796 18 that that IN cord-276598-tm0yj2sn 796 19 it -PRON- PRP cord-276598-tm0yj2sn 796 20 could could MD cord-276598-tm0yj2sn 796 21 be be VB cord-276598-tm0yj2sn 796 22 +2 +2 XX cord-276598-tm0yj2sn 796 23 , , , cord-276598-tm0yj2sn 796 24 and and CC cord-276598-tm0yj2sn 796 25 the the DT cord-276598-tm0yj2sn 796 26 fact fact NN cord-276598-tm0yj2sn 796 27 that that IN cord-276598-tm0yj2sn 796 28 the the DT cord-276598-tm0yj2sn 796 29 reaction reaction NN cord-276598-tm0yj2sn 796 30 produced produce VBD cord-276598-tm0yj2sn 796 31 only only RB cord-276598-tm0yj2sn 796 32 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 796 33 amounts amount NNS cord-276598-tm0yj2sn 796 34 of of IN cord-276598-tm0yj2sn 796 35 the the DT cord-276598-tm0yj2sn 796 36 desired desire VBN cord-276598-tm0yj2sn 796 37 product product NN cord-276598-tm0yj2sn 796 38 ( ( -LRB- cord-276598-tm0yj2sn 796 39 relative relative JJ cord-276598-tm0yj2sn 796 40 to to IN cord-276598-tm0yj2sn 796 41 the the DT cord-276598-tm0yj2sn 796 42 Cu Cu NNP cord-276598-tm0yj2sn 796 43 catalyst catalyst NN cord-276598-tm0yj2sn 796 44 ) ) -RRB- cord-276598-tm0yj2sn 796 45 under under IN cord-276598-tm0yj2sn 796 46 an an DT cord-276598-tm0yj2sn 796 47 inert inert JJ cord-276598-tm0yj2sn 796 48 atmosphere atmosphere NN cord-276598-tm0yj2sn 796 49 was be VBD cord-276598-tm0yj2sn 796 50 a a DT cord-276598-tm0yj2sn 796 51 support support NN cord-276598-tm0yj2sn 796 52 to to IN cord-276598-tm0yj2sn 796 53 the the DT cord-276598-tm0yj2sn 796 54 re re NN cord-276598-tm0yj2sn 796 55 - - NN cord-276598-tm0yj2sn 796 56 oxidation oxidation NN cord-276598-tm0yj2sn 796 57 of of IN cord-276598-tm0yj2sn 796 58 the the DT cord-276598-tm0yj2sn 796 59 Cu Cu NNP cord-276598-tm0yj2sn 796 60 species specie NNS cord-276598-tm0yj2sn 796 61 in in IN cord-276598-tm0yj2sn 796 62 air air NN cord-276598-tm0yj2sn 796 63 . . . cord-276598-tm0yj2sn 797 1 From from IN cord-276598-tm0yj2sn 797 2 their -PRON- PRP$ cord-276598-tm0yj2sn 797 3 experimental experimental JJ cord-276598-tm0yj2sn 797 4 observations observation NNS cord-276598-tm0yj2sn 797 5 , , , cord-276598-tm0yj2sn 797 6 Zhou Zhou NNP cord-276598-tm0yj2sn 797 7 et et NNP cord-276598-tm0yj2sn 797 8 al al NNP cord-276598-tm0yj2sn 797 9 . . . cord-276598-tm0yj2sn 798 1 strongly strongly RB cord-276598-tm0yj2sn 798 2 suggested suggest VBD cord-276598-tm0yj2sn 798 3 that that IN cord-276598-tm0yj2sn 798 4 the the DT cord-276598-tm0yj2sn 798 5 oxidative oxidative JJ cord-276598-tm0yj2sn 798 6 dehydrocoupling dehydrocouple VBG cord-276598-tm0yj2sn 798 7 reaction reaction NN cord-276598-tm0yj2sn 798 8 for for IN cord-276598-tm0yj2sn 798 9 P p NN cord-276598-tm0yj2sn 798 10 - - HYPH cord-276598-tm0yj2sn 798 11 N n CD cord-276598-tm0yj2sn 798 12 synthesis synthesis NN cord-276598-tm0yj2sn 798 13 using use VBG cord-276598-tm0yj2sn 798 14 Cu cu NN cord-276598-tm0yj2sn 798 15 - - HYPH cord-276598-tm0yj2sn 798 16 catalysts catalyst NNS cord-276598-tm0yj2sn 798 17 proceeds proceed NNS cord-276598-tm0yj2sn 798 18 stereospecifically stereospecifically RB cord-276598-tm0yj2sn 798 19 through through IN cord-276598-tm0yj2sn 798 20 an an DT cord-276598-tm0yj2sn 798 21 inversion inversion NN cord-276598-tm0yj2sn 798 22 of of IN cord-276598-tm0yj2sn 798 23 the the DT cord-276598-tm0yj2sn 798 24 configuration configuration NN cord-276598-tm0yj2sn 798 25 at at IN cord-276598-tm0yj2sn 798 26 P p NN cord-276598-tm0yj2sn 798 27 [ [ -LRB- cord-276598-tm0yj2sn 798 28 108 108 CD cord-276598-tm0yj2sn 798 29 ] ] -RRB- cord-276598-tm0yj2sn 798 30 . . . cord-276598-tm0yj2sn 799 1 This this DT cord-276598-tm0yj2sn 799 2 stereospecific stereospecific NN cord-276598-tm0yj2sn 799 3 inversion inversion NN cord-276598-tm0yj2sn 799 4 chemistry chemistry NN cord-276598-tm0yj2sn 799 5 was be VBD cord-276598-tm0yj2sn 799 6 used use VBN cord-276598-tm0yj2sn 799 7 as as IN cord-276598-tm0yj2sn 799 8 an an DT cord-276598-tm0yj2sn 799 9 argument argument NN cord-276598-tm0yj2sn 799 10 in in IN cord-276598-tm0yj2sn 799 11 the the DT cord-276598-tm0yj2sn 799 12 proposed propose VBN cord-276598-tm0yj2sn 799 13 mechanism mechanism NN cord-276598-tm0yj2sn 799 14 to to TO cord-276598-tm0yj2sn 799 15 support support VB cord-276598-tm0yj2sn 799 16 a a DT cord-276598-tm0yj2sn 799 17 formation formation NN cord-276598-tm0yj2sn 799 18 of of IN cord-276598-tm0yj2sn 799 19 halogen halogen NN cord-276598-tm0yj2sn 799 20 - - HYPH cord-276598-tm0yj2sn 799 21 phosphate phosphate NN cord-276598-tm0yj2sn 799 22 intermediate intermediate NN cord-276598-tm0yj2sn 799 23 when when WRB cord-276598-tm0yj2sn 799 24 Cu Cu NNP cord-276598-tm0yj2sn 799 25 catalyst catalyst NN cord-276598-tm0yj2sn 799 26 is be VBZ cord-276598-tm0yj2sn 799 27 reacted react VBN cord-276598-tm0yj2sn 799 28 with with IN cord-276598-tm0yj2sn 799 29 H H NNP cord-276598-tm0yj2sn 799 30 - - HYPH cord-276598-tm0yj2sn 799 31 phosphonate phosphonate NNP cord-276598-tm0yj2sn 799 32 ( ( -LRB- cord-276598-tm0yj2sn 799 33 H h NN cord-276598-tm0yj2sn 799 34 - - HYPH cord-276598-tm0yj2sn 799 35 P p NN cord-276598-tm0yj2sn 799 36 ) ) -RRB- cord-276598-tm0yj2sn 799 37 . . . cord-276598-tm0yj2sn 800 1 The the DT cord-276598-tm0yj2sn 800 2 amine amine NN cord-276598-tm0yj2sn 800 3 ( ( -LRB- cord-276598-tm0yj2sn 800 4 as as IN cord-276598-tm0yj2sn 800 5 a a DT cord-276598-tm0yj2sn 800 6 nucleophile nucleophile NN cord-276598-tm0yj2sn 800 7 ) ) -RRB- cord-276598-tm0yj2sn 800 8 subsequently subsequently RB cord-276598-tm0yj2sn 800 9 attacks attack VBZ cord-276598-tm0yj2sn 800 10 the the DT cord-276598-tm0yj2sn 800 11 intermediate intermediate JJ cord-276598-tm0yj2sn 800 12 from from IN cord-276598-tm0yj2sn 800 13 behind behind RB cord-276598-tm0yj2sn 800 14 to to TO cord-276598-tm0yj2sn 800 15 give give VB cord-276598-tm0yj2sn 800 16 the the DT cord-276598-tm0yj2sn 800 17 product product NN cord-276598-tm0yj2sn 800 18 , , , cord-276598-tm0yj2sn 800 19 while while IN cord-276598-tm0yj2sn 800 20 the the DT cord-276598-tm0yj2sn 800 21 Cu(I Cu(I NNP cord-276598-tm0yj2sn 800 22 ) ) -RRB- cord-276598-tm0yj2sn 800 23 catalyst catalyst NN cord-276598-tm0yj2sn 800 24 is be VBZ cord-276598-tm0yj2sn 800 25 then then RB cord-276598-tm0yj2sn 800 26 reoxidized reoxidize VBN cord-276598-tm0yj2sn 800 27 by by IN cord-276598-tm0yj2sn 800 28 O2 O2 NNP cord-276598-tm0yj2sn 800 29 to to IN cord-276598-tm0yj2sn 800 30 Cu(II Cu(II NNP cord-276598-tm0yj2sn 800 31 ) ) -RRB- cord-276598-tm0yj2sn 800 32 in in IN cord-276598-tm0yj2sn 800 33 the the DT cord-276598-tm0yj2sn 800 34 presence presence NN cord-276598-tm0yj2sn 800 35 of of IN cord-276598-tm0yj2sn 800 36 hydrogen hydrogen NN cord-276598-tm0yj2sn 800 37 halide halide NN cord-276598-tm0yj2sn 800 38 formed form VBN cord-276598-tm0yj2sn 800 39 from from IN cord-276598-tm0yj2sn 800 40 the the DT cord-276598-tm0yj2sn 800 41 process process NN cord-276598-tm0yj2sn 800 42 . . . cord-276598-tm0yj2sn 801 1 Water water NN cord-276598-tm0yj2sn 801 2 is be VBZ cord-276598-tm0yj2sn 801 3 also also RB cord-276598-tm0yj2sn 801 4 formed form VBN cord-276598-tm0yj2sn 801 5 as as IN cord-276598-tm0yj2sn 801 6 a a DT cord-276598-tm0yj2sn 801 7 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 801 8 waste waste NN cord-276598-tm0yj2sn 801 9 ( ( -LRB- cord-276598-tm0yj2sn 801 10 Scheme scheme NN cord-276598-tm0yj2sn 801 11 29b 29b CD cord-276598-tm0yj2sn 801 12 ) ) -RRB- cord-276598-tm0yj2sn 801 13 . . . cord-276598-tm0yj2sn 802 1 The the DT cord-276598-tm0yj2sn 802 2 mechanism mechanism NN cord-276598-tm0yj2sn 802 3 as as IN cord-276598-tm0yj2sn 802 4 reported report VBN cord-276598-tm0yj2sn 802 5 by by IN cord-276598-tm0yj2sn 802 6 Dangroo Dangroo NNP cord-276598-tm0yj2sn 802 7 et et NNP cord-276598-tm0yj2sn 802 8 al al NNP cord-276598-tm0yj2sn 802 9 . . . cord-276598-tm0yj2sn 803 1 involved involve VBN cord-276598-tm0yj2sn 803 2 transmetalation transmetalation NN cord-276598-tm0yj2sn 803 3 to to TO cord-276598-tm0yj2sn 803 4 form form VB cord-276598-tm0yj2sn 803 5 an an DT cord-276598-tm0yj2sn 803 6 azidocopper(II azidocopper(II NNP cord-276598-tm0yj2sn 803 7 ) ) -RRB- cord-276598-tm0yj2sn 803 8 species specie NNS cord-276598-tm0yj2sn 803 9 in in IN cord-276598-tm0yj2sn 803 10 the the DT cord-276598-tm0yj2sn 803 11 first first JJ cord-276598-tm0yj2sn 803 12 step step NN cord-276598-tm0yj2sn 803 13 ( ( -LRB- cord-276598-tm0yj2sn 803 14 Scheme scheme NN cord-276598-tm0yj2sn 803 15 30 30 CD cord-276598-tm0yj2sn 803 16 ) ) -RRB- cord-276598-tm0yj2sn 803 17 [ [ -LRB- cord-276598-tm0yj2sn 803 18 109 109 CD cord-276598-tm0yj2sn 803 19 ] ] -RRB- cord-276598-tm0yj2sn 803 20 . . . cord-276598-tm0yj2sn 804 1 Similar similar JJ cord-276598-tm0yj2sn 804 2 transmetalation transmetalation NN cord-276598-tm0yj2sn 804 3 reactions reaction NNS cord-276598-tm0yj2sn 804 4 involving involve VBG cord-276598-tm0yj2sn 804 5 the the DT cord-276598-tm0yj2sn 804 6 phenylboronic phenylboronic JJ cord-276598-tm0yj2sn 804 7 acid acid NN cord-276598-tm0yj2sn 804 8 - - HYPH cord-276598-tm0yj2sn 804 9 based base VBN cord-276598-tm0yj2sn 804 10 substrates substrate NNS cord-276598-tm0yj2sn 804 11 and and CC cord-276598-tm0yj2sn 804 12 the the DT cord-276598-tm0yj2sn 804 13 azidocopper(II azidocopper(II NNP cord-276598-tm0yj2sn 804 14 ) ) -RRB- cord-276598-tm0yj2sn 804 15 species specie NNS cord-276598-tm0yj2sn 804 16 in in IN cord-276598-tm0yj2sn 804 17 the the DT cord-276598-tm0yj2sn 804 18 second second JJ cord-276598-tm0yj2sn 804 19 Scheme Scheme NNP cord-276598-tm0yj2sn 804 20 29 29 CD cord-276598-tm0yj2sn 804 21 . . . cord-276598-tm0yj2sn 805 1 Proposed propose VBN cord-276598-tm0yj2sn 805 2 mechanism mechanism NN cord-276598-tm0yj2sn 805 3 for for IN cord-276598-tm0yj2sn 805 4 the the DT cord-276598-tm0yj2sn 805 5 Cu cu NN cord-276598-tm0yj2sn 805 6 - - HYPH cord-276598-tm0yj2sn 805 7 mediated mediate VBN cord-276598-tm0yj2sn 805 8 synthesis synthesis NN cord-276598-tm0yj2sn 805 9 of of IN cord-276598-tm0yj2sn 805 10 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 805 11 . . . cord-276598-tm0yj2sn 806 1 Mizuno Mizuno NNP cord-276598-tm0yj2sn 806 2 et et NNP cord-276598-tm0yj2sn 806 3 al al NNP cord-276598-tm0yj2sn 806 4 . . . cord-276598-tm0yj2sn 807 1 proposed propose VBD cord-276598-tm0yj2sn 807 2 a a DT cord-276598-tm0yj2sn 807 3 mechanism mechanism NN cord-276598-tm0yj2sn 807 4 for for IN cord-276598-tm0yj2sn 807 5 the the DT cord-276598-tm0yj2sn 807 6 reaction reaction NN cord-276598-tm0yj2sn 807 7 in in IN cord-276598-tm0yj2sn 807 8 which which WDT cord-276598-tm0yj2sn 807 9 K K NNP cord-276598-tm0yj2sn 807 10 2 2 CD cord-276598-tm0yj2sn 807 11 CO CO NNP cord-276598-tm0yj2sn 807 12 3 3 CD cord-276598-tm0yj2sn 807 13 first first JJ cord-276598-tm0yj2sn 807 14 deprotonates deprotonate NNS cord-276598-tm0yj2sn 807 15 the the DT cord-276598-tm0yj2sn 807 16 amide amide NN cord-276598-tm0yj2sn 807 17 , , , cord-276598-tm0yj2sn 807 18 affording afford VBG cord-276598-tm0yj2sn 807 19 unpaired unpaired JJ cord-276598-tm0yj2sn 807 20 electrons electron NNS cord-276598-tm0yj2sn 807 21 on on IN cord-276598-tm0yj2sn 807 22 a a DT cord-276598-tm0yj2sn 807 23 Cu cu NN cord-276598-tm0yj2sn 807 24 - - NN cord-276598-tm0yj2sn 807 25 amide amide NN cord-276598-tm0yj2sn 807 26 complex complex NN cord-276598-tm0yj2sn 807 27 [ [ -LRB- cord-276598-tm0yj2sn 807 28 107 107 CD cord-276598-tm0yj2sn 807 29 ] ] -RRB- cord-276598-tm0yj2sn 807 30 . . . cord-276598-tm0yj2sn 808 1 Furthermore furthermore RB cord-276598-tm0yj2sn 808 2 , , , cord-276598-tm0yj2sn 808 3 it -PRON- PRP cord-276598-tm0yj2sn 808 4 was be VBD cord-276598-tm0yj2sn 808 5 suggested suggest VBN cord-276598-tm0yj2sn 808 6 that that IN cord-276598-tm0yj2sn 808 7 it -PRON- PRP cord-276598-tm0yj2sn 808 8 is be VBZ cord-276598-tm0yj2sn 808 9 possible possible JJ cord-276598-tm0yj2sn 808 10 that that IN cord-276598-tm0yj2sn 808 11 K K NNP cord-276598-tm0yj2sn 808 12 2 2 CD cord-276598-tm0yj2sn 808 13 CO CO NNP cord-276598-tm0yj2sn 808 14 3 3 CD cord-276598-tm0yj2sn 808 15 deprotonates deprotonate NNS cord-276598-tm0yj2sn 808 16 H h NN cord-276598-tm0yj2sn 808 17 - - HYPH cord-276598-tm0yj2sn 808 18 P p NN cord-276598-tm0yj2sn 808 19 or or CC cord-276598-tm0yj2sn 808 20 provides provide VBZ cord-276598-tm0yj2sn 808 21 a a DT cord-276598-tm0yj2sn 808 22 medium medium NN cord-276598-tm0yj2sn 808 23 for for IN cord-276598-tm0yj2sn 808 24 the the DT cord-276598-tm0yj2sn 808 25 H H NNP cord-276598-tm0yj2sn 808 26 - - HYPH cord-276598-tm0yj2sn 808 27 P p NN cord-276598-tm0yj2sn 808 28 tautomer tautomer NN cord-276598-tm0yj2sn 808 29 to to IN cord-276598-tm0yj2sn 808 30 further further RB cord-276598-tm0yj2sn 808 31 complex complex JJ cord-276598-tm0yj2sn 808 32 with with IN cord-276598-tm0yj2sn 808 33 the the DT cord-276598-tm0yj2sn 808 34 Cu cu NN cord-276598-tm0yj2sn 808 35 - - HYPH cord-276598-tm0yj2sn 808 36 amide amide NN cord-276598-tm0yj2sn 808 37 complex complex NN cord-276598-tm0yj2sn 808 38 . . . cord-276598-tm0yj2sn 809 1 The the DT cord-276598-tm0yj2sn 809 2 Cu cu NN cord-276598-tm0yj2sn 809 3 - - HYPH cord-276598-tm0yj2sn 809 4 amide amide NN cord-276598-tm0yj2sn 809 5 - - HYPH cord-276598-tm0yj2sn 809 6 phosphite phosphite NN cord-276598-tm0yj2sn 809 7 intermediate intermediate NN cord-276598-tm0yj2sn 809 8 undergoes undergo VBZ cord-276598-tm0yj2sn 809 9 reductive reductive JJ cord-276598-tm0yj2sn 809 10 elimination elimination NN cord-276598-tm0yj2sn 809 11 to to TO cord-276598-tm0yj2sn 809 12 afford afford VB cord-276598-tm0yj2sn 809 13 the the DT cord-276598-tm0yj2sn 809 14 desired desire VBN cord-276598-tm0yj2sn 809 15 product product NN cord-276598-tm0yj2sn 809 16 , , , cord-276598-tm0yj2sn 809 17 while while IN cord-276598-tm0yj2sn 809 18 O o NN cord-276598-tm0yj2sn 809 19 2 2 CD cord-276598-tm0yj2sn 809 20 re re NN cord-276598-tm0yj2sn 809 21 - - NN cord-276598-tm0yj2sn 809 22 oxidizes oxidize NNS cord-276598-tm0yj2sn 810 1 the the DT cord-276598-tm0yj2sn 810 2 reduced reduce VBN cord-276598-tm0yj2sn 810 3 Cu Cu NNP cord-276598-tm0yj2sn 810 4 species specie NNS cord-276598-tm0yj2sn 810 5 to to TO cord-276598-tm0yj2sn 810 6 regenerate regenerate VB cord-276598-tm0yj2sn 810 7 the the DT cord-276598-tm0yj2sn 810 8 active active JJ cord-276598-tm0yj2sn 810 9 catalyst catalyst NN cord-276598-tm0yj2sn 810 10 . . . cord-276598-tm0yj2sn 811 1 Although although IN cord-276598-tm0yj2sn 811 2 the the DT cord-276598-tm0yj2sn 811 3 oxidation oxidation NN cord-276598-tm0yj2sn 811 4 state state NN cord-276598-tm0yj2sn 811 5 of of IN cord-276598-tm0yj2sn 811 6 Cu Cu NNP cord-276598-tm0yj2sn 811 7 in in IN cord-276598-tm0yj2sn 811 8 the the DT cord-276598-tm0yj2sn 811 9 reaction reaction NN cord-276598-tm0yj2sn 811 10 mechanism mechanism NN cord-276598-tm0yj2sn 811 11 was be VBD cord-276598-tm0yj2sn 811 12 not not RB cord-276598-tm0yj2sn 811 13 explained explain VBN cord-276598-tm0yj2sn 811 14 , , , cord-276598-tm0yj2sn 811 15 the the DT cord-276598-tm0yj2sn 811 16 authors author NNS cord-276598-tm0yj2sn 811 17 suggested suggest VBD cord-276598-tm0yj2sn 811 18 that that IN cord-276598-tm0yj2sn 811 19 it -PRON- PRP cord-276598-tm0yj2sn 811 20 could could MD cord-276598-tm0yj2sn 811 21 be be VB cord-276598-tm0yj2sn 811 22 +2 +2 XX cord-276598-tm0yj2sn 811 23 , , , cord-276598-tm0yj2sn 811 24 and and CC cord-276598-tm0yj2sn 811 25 the the DT cord-276598-tm0yj2sn 811 26 fact fact NN cord-276598-tm0yj2sn 811 27 that that IN cord-276598-tm0yj2sn 811 28 the the DT cord-276598-tm0yj2sn 811 29 reaction reaction NN cord-276598-tm0yj2sn 811 30 produced produce VBD cord-276598-tm0yj2sn 811 31 only only RB cord-276598-tm0yj2sn 811 32 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 811 33 amounts amount NNS cord-276598-tm0yj2sn 811 34 of of IN cord-276598-tm0yj2sn 811 35 the the DT cord-276598-tm0yj2sn 811 36 desired desire VBN cord-276598-tm0yj2sn 811 37 product product NN cord-276598-tm0yj2sn 811 38 ( ( -LRB- cord-276598-tm0yj2sn 811 39 relative relative JJ cord-276598-tm0yj2sn 811 40 to to IN cord-276598-tm0yj2sn 811 41 the the DT cord-276598-tm0yj2sn 811 42 Cu Cu NNP cord-276598-tm0yj2sn 811 43 catalyst catalyst NN cord-276598-tm0yj2sn 811 44 ) ) -RRB- cord-276598-tm0yj2sn 811 45 under under IN cord-276598-tm0yj2sn 811 46 an an DT cord-276598-tm0yj2sn 811 47 inert inert JJ cord-276598-tm0yj2sn 811 48 atmosphere atmosphere NN cord-276598-tm0yj2sn 811 49 was be VBD cord-276598-tm0yj2sn 811 50 a a DT cord-276598-tm0yj2sn 811 51 support support NN cord-276598-tm0yj2sn 811 52 to to IN cord-276598-tm0yj2sn 811 53 the the DT cord-276598-tm0yj2sn 811 54 re re NN cord-276598-tm0yj2sn 811 55 - - NN cord-276598-tm0yj2sn 811 56 oxidation oxidation NN cord-276598-tm0yj2sn 811 57 of of IN cord-276598-tm0yj2sn 811 58 the the DT cord-276598-tm0yj2sn 811 59 Cu Cu NNP cord-276598-tm0yj2sn 811 60 species specie NNS cord-276598-tm0yj2sn 811 61 in in IN cord-276598-tm0yj2sn 811 62 air air NN cord-276598-tm0yj2sn 811 63 . . . cord-276598-tm0yj2sn 812 1 From from IN cord-276598-tm0yj2sn 812 2 their -PRON- PRP$ cord-276598-tm0yj2sn 812 3 experimental experimental JJ cord-276598-tm0yj2sn 812 4 observations observation NNS cord-276598-tm0yj2sn 812 5 , , , cord-276598-tm0yj2sn 812 6 Zhou Zhou NNP cord-276598-tm0yj2sn 812 7 et et NNP cord-276598-tm0yj2sn 812 8 al al NNP cord-276598-tm0yj2sn 812 9 . . . cord-276598-tm0yj2sn 813 1 strongly strongly RB cord-276598-tm0yj2sn 813 2 suggested suggest VBD cord-276598-tm0yj2sn 813 3 that that IN cord-276598-tm0yj2sn 813 4 the the DT cord-276598-tm0yj2sn 813 5 oxidative oxidative JJ cord-276598-tm0yj2sn 813 6 dehydrocoupling dehydrocouple VBG cord-276598-tm0yj2sn 813 7 reaction reaction NN cord-276598-tm0yj2sn 813 8 for for IN cord-276598-tm0yj2sn 813 9 P p NN cord-276598-tm0yj2sn 813 10 - - HYPH cord-276598-tm0yj2sn 813 11 N n CD cord-276598-tm0yj2sn 813 12 synthesis synthesis NN cord-276598-tm0yj2sn 813 13 using use VBG cord-276598-tm0yj2sn 813 14 Cu cu NN cord-276598-tm0yj2sn 813 15 - - HYPH cord-276598-tm0yj2sn 813 16 catalysts catalyst NNS cord-276598-tm0yj2sn 813 17 proceeds proceed NNS cord-276598-tm0yj2sn 813 18 stereospecifically stereospecifically RB cord-276598-tm0yj2sn 813 19 through through IN cord-276598-tm0yj2sn 813 20 an an DT cord-276598-tm0yj2sn 813 21 inversion inversion NN cord-276598-tm0yj2sn 813 22 of of IN cord-276598-tm0yj2sn 813 23 the the DT cord-276598-tm0yj2sn 813 24 configuration configuration NN cord-276598-tm0yj2sn 813 25 at at IN cord-276598-tm0yj2sn 813 26 P p NN cord-276598-tm0yj2sn 813 27 [ [ -LRB- cord-276598-tm0yj2sn 813 28 108 108 CD cord-276598-tm0yj2sn 813 29 ] ] -RRB- cord-276598-tm0yj2sn 813 30 . . . cord-276598-tm0yj2sn 814 1 This this DT cord-276598-tm0yj2sn 814 2 stereospecific stereospecific NN cord-276598-tm0yj2sn 814 3 inversion inversion NN cord-276598-tm0yj2sn 814 4 chemistry chemistry NN cord-276598-tm0yj2sn 814 5 was be VBD cord-276598-tm0yj2sn 814 6 used use VBN cord-276598-tm0yj2sn 814 7 as as IN cord-276598-tm0yj2sn 814 8 an an DT cord-276598-tm0yj2sn 814 9 argument argument NN cord-276598-tm0yj2sn 814 10 in in IN cord-276598-tm0yj2sn 814 11 the the DT cord-276598-tm0yj2sn 814 12 proposed propose VBN cord-276598-tm0yj2sn 814 13 mechanism mechanism NN cord-276598-tm0yj2sn 814 14 to to TO cord-276598-tm0yj2sn 814 15 support support VB cord-276598-tm0yj2sn 814 16 a a DT cord-276598-tm0yj2sn 814 17 formation formation NN cord-276598-tm0yj2sn 814 18 of of IN cord-276598-tm0yj2sn 814 19 halogen halogen NN cord-276598-tm0yj2sn 814 20 - - HYPH cord-276598-tm0yj2sn 814 21 phosphate phosphate NN cord-276598-tm0yj2sn 814 22 intermediate intermediate NN cord-276598-tm0yj2sn 814 23 when when WRB cord-276598-tm0yj2sn 814 24 Cu Cu NNP cord-276598-tm0yj2sn 814 25 catalyst catalyst NN cord-276598-tm0yj2sn 814 26 is be VBZ cord-276598-tm0yj2sn 814 27 reacted react VBN cord-276598-tm0yj2sn 814 28 with with IN cord-276598-tm0yj2sn 814 29 H H NNP cord-276598-tm0yj2sn 814 30 - - HYPH cord-276598-tm0yj2sn 814 31 phosphonate phosphonate NNP cord-276598-tm0yj2sn 814 32 ( ( -LRB- cord-276598-tm0yj2sn 814 33 H h NN cord-276598-tm0yj2sn 814 34 - - HYPH cord-276598-tm0yj2sn 814 35 P p NN cord-276598-tm0yj2sn 814 36 ) ) -RRB- cord-276598-tm0yj2sn 814 37 . . . cord-276598-tm0yj2sn 815 1 The the DT cord-276598-tm0yj2sn 815 2 amine amine NN cord-276598-tm0yj2sn 815 3 ( ( -LRB- cord-276598-tm0yj2sn 815 4 as as IN cord-276598-tm0yj2sn 815 5 a a DT cord-276598-tm0yj2sn 815 6 nucleophile nucleophile NN cord-276598-tm0yj2sn 815 7 ) ) -RRB- cord-276598-tm0yj2sn 815 8 subsequently subsequently RB cord-276598-tm0yj2sn 815 9 attacks attack VBZ cord-276598-tm0yj2sn 815 10 the the DT cord-276598-tm0yj2sn 815 11 intermediate intermediate JJ cord-276598-tm0yj2sn 815 12 from from IN cord-276598-tm0yj2sn 815 13 behind behind RB cord-276598-tm0yj2sn 815 14 to to TO cord-276598-tm0yj2sn 815 15 give give VB cord-276598-tm0yj2sn 815 16 the the DT cord-276598-tm0yj2sn 815 17 product product NN cord-276598-tm0yj2sn 815 18 , , , cord-276598-tm0yj2sn 815 19 while while IN cord-276598-tm0yj2sn 815 20 the the DT cord-276598-tm0yj2sn 815 21 Cu(I Cu(I NNP cord-276598-tm0yj2sn 815 22 ) ) -RRB- cord-276598-tm0yj2sn 815 23 catalyst catalyst NN cord-276598-tm0yj2sn 815 24 is be VBZ cord-276598-tm0yj2sn 815 25 then then RB cord-276598-tm0yj2sn 815 26 reoxidized reoxidize VBN cord-276598-tm0yj2sn 815 27 by by IN cord-276598-tm0yj2sn 815 28 O o NN cord-276598-tm0yj2sn 815 29 2 2 CD cord-276598-tm0yj2sn 815 30 to to IN cord-276598-tm0yj2sn 815 31 Cu(II cu(ii NN cord-276598-tm0yj2sn 815 32 ) ) -RRB- cord-276598-tm0yj2sn 815 33 in in IN cord-276598-tm0yj2sn 815 34 the the DT cord-276598-tm0yj2sn 815 35 presence presence NN cord-276598-tm0yj2sn 815 36 of of IN cord-276598-tm0yj2sn 815 37 hydrogen hydrogen NN cord-276598-tm0yj2sn 815 38 halide halide NN cord-276598-tm0yj2sn 815 39 formed form VBN cord-276598-tm0yj2sn 815 40 from from IN cord-276598-tm0yj2sn 815 41 the the DT cord-276598-tm0yj2sn 815 42 process process NN cord-276598-tm0yj2sn 815 43 . . . cord-276598-tm0yj2sn 816 1 Water water NN cord-276598-tm0yj2sn 816 2 is be VBZ cord-276598-tm0yj2sn 816 3 also also RB cord-276598-tm0yj2sn 816 4 formed form VBN cord-276598-tm0yj2sn 816 5 as as IN cord-276598-tm0yj2sn 816 6 a a DT cord-276598-tm0yj2sn 816 7 stoichiometric stoichiometric JJ cord-276598-tm0yj2sn 816 8 waste waste NN cord-276598-tm0yj2sn 816 9 ( ( -LRB- cord-276598-tm0yj2sn 816 10 Scheme scheme NN cord-276598-tm0yj2sn 816 11 29b 29b CD cord-276598-tm0yj2sn 816 12 ) ) -RRB- cord-276598-tm0yj2sn 816 13 . . . cord-276598-tm0yj2sn 817 1 The the DT cord-276598-tm0yj2sn 817 2 mechanism mechanism NN cord-276598-tm0yj2sn 817 3 as as IN cord-276598-tm0yj2sn 817 4 reported report VBN cord-276598-tm0yj2sn 817 5 by by IN cord-276598-tm0yj2sn 817 6 Dangroo Dangroo NNP cord-276598-tm0yj2sn 817 7 et et NNP cord-276598-tm0yj2sn 817 8 al al NNP cord-276598-tm0yj2sn 817 9 . . . cord-276598-tm0yj2sn 818 1 involved involve VBN cord-276598-tm0yj2sn 818 2 transmetalation transmetalation NN cord-276598-tm0yj2sn 818 3 to to TO cord-276598-tm0yj2sn 818 4 form form VB cord-276598-tm0yj2sn 818 5 an an DT cord-276598-tm0yj2sn 818 6 azidocopper(II azidocopper(II NNP cord-276598-tm0yj2sn 818 7 ) ) -RRB- cord-276598-tm0yj2sn 818 8 species specie NNS cord-276598-tm0yj2sn 818 9 in in IN cord-276598-tm0yj2sn 818 10 the the DT cord-276598-tm0yj2sn 818 11 first first JJ cord-276598-tm0yj2sn 818 12 step step NN cord-276598-tm0yj2sn 818 13 ( ( -LRB- cord-276598-tm0yj2sn 818 14 Scheme scheme NN cord-276598-tm0yj2sn 818 15 30 30 CD cord-276598-tm0yj2sn 818 16 ) ) -RRB- cord-276598-tm0yj2sn 818 17 [ [ -LRB- cord-276598-tm0yj2sn 818 18 109 109 CD cord-276598-tm0yj2sn 818 19 ] ] -RRB- cord-276598-tm0yj2sn 818 20 . . . cord-276598-tm0yj2sn 819 1 Similar similar JJ cord-276598-tm0yj2sn 819 2 transmetalation transmetalation NN cord-276598-tm0yj2sn 819 3 reactions reaction NNS cord-276598-tm0yj2sn 819 4 involving involve VBG cord-276598-tm0yj2sn 819 5 the the DT cord-276598-tm0yj2sn 819 6 phenylboronic phenylboronic JJ cord-276598-tm0yj2sn 819 7 acid acid NN cord-276598-tm0yj2sn 819 8 - - HYPH cord-276598-tm0yj2sn 819 9 based base VBN cord-276598-tm0yj2sn 819 10 substrates substrate NNS cord-276598-tm0yj2sn 819 11 and and CC cord-276598-tm0yj2sn 819 12 the the DT cord-276598-tm0yj2sn 819 13 azidocopper(II azidocopper(II NNP cord-276598-tm0yj2sn 819 14 ) ) -RRB- cord-276598-tm0yj2sn 819 15 species specie NNS cord-276598-tm0yj2sn 819 16 in in IN cord-276598-tm0yj2sn 819 17 the the DT cord-276598-tm0yj2sn 819 18 second second JJ cord-276598-tm0yj2sn 819 19 step step NN cord-276598-tm0yj2sn 819 20 result result NN cord-276598-tm0yj2sn 819 21 in in IN cord-276598-tm0yj2sn 819 22 the the DT cord-276598-tm0yj2sn 819 23 formation formation NN cord-276598-tm0yj2sn 819 24 of of IN cord-276598-tm0yj2sn 819 25 a a DT cord-276598-tm0yj2sn 819 26 phenyl phenyl NNP cord-276598-tm0yj2sn 819 27 - - HYPH cord-276598-tm0yj2sn 819 28 azidocopper(II azidocopper(II NNP cord-276598-tm0yj2sn 819 29 ) ) -RRB- cord-276598-tm0yj2sn 819 30 complex complex NNP cord-276598-tm0yj2sn 819 31 . . . cord-276598-tm0yj2sn 820 1 The the DT cord-276598-tm0yj2sn 820 2 complex complex NN cord-276598-tm0yj2sn 820 3 is be VBZ cord-276598-tm0yj2sn 820 4 oxidized oxidize VBN cord-276598-tm0yj2sn 820 5 in in IN cord-276598-tm0yj2sn 820 6 the the DT cord-276598-tm0yj2sn 820 7 presence presence NN cord-276598-tm0yj2sn 820 8 of of IN cord-276598-tm0yj2sn 820 9 Cu(II Cu(II NNP cord-276598-tm0yj2sn 820 10 ) ) -RRB- cord-276598-tm0yj2sn 820 11 to to IN cord-276598-tm0yj2sn 820 12 a a DT cord-276598-tm0yj2sn 820 13 phenyl phenyl NN cord-276598-tm0yj2sn 820 14 - - HYPH cord-276598-tm0yj2sn 820 15 azidocopper(III azidocopper(iii CD cord-276598-tm0yj2sn 820 16 ) ) -RRB- cord-276598-tm0yj2sn 820 17 complex complex NN cord-276598-tm0yj2sn 820 18 , , , cord-276598-tm0yj2sn 820 19 which which WDT cord-276598-tm0yj2sn 820 20 results result VBZ cord-276598-tm0yj2sn 820 21 in in IN cord-276598-tm0yj2sn 820 22 the the DT cord-276598-tm0yj2sn 820 23 formation formation NN cord-276598-tm0yj2sn 820 24 of of IN cord-276598-tm0yj2sn 820 25 the the DT cord-276598-tm0yj2sn 820 26 organic organic JJ cord-276598-tm0yj2sn 820 27 azide azide NN cord-276598-tm0yj2sn 820 28 and and CC cord-276598-tm0yj2sn 820 29 forms form VBZ cord-276598-tm0yj2sn 820 30 Cu(I Cu(I NNP cord-276598-tm0yj2sn 820 31 ) ) -RRB- cord-276598-tm0yj2sn 820 32 after after IN cord-276598-tm0yj2sn 820 33 reductive reductive JJ cord-276598-tm0yj2sn 820 34 elimination elimination NN cord-276598-tm0yj2sn 820 35 . . . cord-276598-tm0yj2sn 821 1 From from IN cord-276598-tm0yj2sn 821 2 this this DT cord-276598-tm0yj2sn 821 3 , , , cord-276598-tm0yj2sn 821 4 a a DT cord-276598-tm0yj2sn 821 5 reaction reaction NN cord-276598-tm0yj2sn 821 6 between between IN cord-276598-tm0yj2sn 821 7 the the DT cord-276598-tm0yj2sn 821 8 ( ( -LRB- cord-276598-tm0yj2sn 821 9 RO ro NN cord-276598-tm0yj2sn 821 10 ) ) -RRB- cord-276598-tm0yj2sn 821 11 3 3 CD cord-276598-tm0yj2sn 821 12 P p NN cord-276598-tm0yj2sn 821 13 ( ( -LRB- cord-276598-tm0yj2sn 821 14 R r NN cord-276598-tm0yj2sn 821 15 = = NN cord-276598-tm0yj2sn 821 16 alkyl alkyl NN cord-276598-tm0yj2sn 821 17 ) ) -RRB- cord-276598-tm0yj2sn 821 18 and and CC cord-276598-tm0yj2sn 821 19 the the DT cord-276598-tm0yj2sn 821 20 organic organic JJ cord-276598-tm0yj2sn 821 21 azide azide NN cord-276598-tm0yj2sn 821 22 gives give VBZ cord-276598-tm0yj2sn 821 23 phosphorimidate phosphorimidate NNP cord-276598-tm0yj2sn 821 24 ( ( -LRB- cord-276598-tm0yj2sn 821 25 with with IN cord-276598-tm0yj2sn 821 26 loss loss NN cord-276598-tm0yj2sn 821 27 of of IN cord-276598-tm0yj2sn 821 28 N n CD cord-276598-tm0yj2sn 821 29 2 2 CD cord-276598-tm0yj2sn 821 30 ) ) -RRB- cord-276598-tm0yj2sn 821 31 , , , cord-276598-tm0yj2sn 821 32 which which WDT cord-276598-tm0yj2sn 821 33 undergoes undergo VBZ cord-276598-tm0yj2sn 821 34 hydrolysis hydrolysis NN cord-276598-tm0yj2sn 821 35 to to TO cord-276598-tm0yj2sn 821 36 afford afford VB cord-276598-tm0yj2sn 821 37 the the DT cord-276598-tm0yj2sn 821 38 desired desire VBN cord-276598-tm0yj2sn 821 39 product product NN cord-276598-tm0yj2sn 821 40 , , , cord-276598-tm0yj2sn 821 41 while while IN cord-276598-tm0yj2sn 821 42 the the DT cord-276598-tm0yj2sn 821 43 Cu(I Cu(I NNP cord-276598-tm0yj2sn 821 44 ) ) -RRB- cord-276598-tm0yj2sn 821 45 is be VBZ cord-276598-tm0yj2sn 821 46 reoxidized reoxidize VBN cord-276598-tm0yj2sn 821 47 to to IN cord-276598-tm0yj2sn 821 48 Cu(II Cu(II NNP cord-276598-tm0yj2sn 821 49 ) ) -RRB- cord-276598-tm0yj2sn 821 50 in in IN cord-276598-tm0yj2sn 821 51 the the DT cord-276598-tm0yj2sn 821 52 catalytic catalytic JJ cord-276598-tm0yj2sn 821 53 cycle cycle NN cord-276598-tm0yj2sn 821 54 . . . cord-276598-tm0yj2sn 822 1 Although although IN cord-276598-tm0yj2sn 822 2 the the DT cord-276598-tm0yj2sn 822 3 mechanism mechanism NN cord-276598-tm0yj2sn 822 4 satisfies satisfy VBZ cord-276598-tm0yj2sn 822 5 much much JJ cord-276598-tm0yj2sn 822 6 of of IN cord-276598-tm0yj2sn 822 7 the the DT cord-276598-tm0yj2sn 822 8 observed observed JJ cord-276598-tm0yj2sn 822 9 results result NNS cord-276598-tm0yj2sn 822 10 , , , cord-276598-tm0yj2sn 822 11 the the DT cord-276598-tm0yj2sn 822 12 proposed propose VBN cord-276598-tm0yj2sn 822 13 second second JJ cord-276598-tm0yj2sn 822 14 step step NN cord-276598-tm0yj2sn 822 15 , , , cord-276598-tm0yj2sn 822 16 transmetalation transmetalation NN cord-276598-tm0yj2sn 822 17 , , , cord-276598-tm0yj2sn 822 18 would would MD cord-276598-tm0yj2sn 822 19 have have VB cord-276598-tm0yj2sn 822 20 resulted result VBN cord-276598-tm0yj2sn 822 21 in in IN cord-276598-tm0yj2sn 822 22 borazidic borazidic NN cord-276598-tm0yj2sn 822 23 acid acid NN cord-276598-tm0yj2sn 822 24 ( ( -LRB- cord-276598-tm0yj2sn 822 25 i.e. i.e. FW cord-276598-tm0yj2sn 822 26 , , , cord-276598-tm0yj2sn 822 27 N n NN cord-276598-tm0yj2sn 822 28 3 3 CD cord-276598-tm0yj2sn 822 29 -B(OH -B(OH . cord-276598-tm0yj2sn 822 30 ) ) -RRB- cord-276598-tm0yj2sn 822 31 2 2 CD cord-276598-tm0yj2sn 822 32 ) ) -RRB- cord-276598-tm0yj2sn 822 33 and and CC cord-276598-tm0yj2sn 822 34 Cu(II)-phenyl Cu(II)-phenyl NNP cord-276598-tm0yj2sn 822 35 species specie NNS cord-276598-tm0yj2sn 822 36 or or CC cord-276598-tm0yj2sn 822 37 Cu(OH Cu(OH NNS cord-276598-tm0yj2sn 822 38 ) ) -RRB- cord-276598-tm0yj2sn 822 39 2 2 CD cord-276598-tm0yj2sn 822 40 species specie NNS cord-276598-tm0yj2sn 822 41 when when WRB cord-276598-tm0yj2sn 822 42 the the DT cord-276598-tm0yj2sn 822 43 azidocopper(II azidocopper(II NNP cord-276598-tm0yj2sn 822 44 ) ) -RRB- cord-276598-tm0yj2sn 822 45 species specie NNS cord-276598-tm0yj2sn 822 46 reacted react VBD cord-276598-tm0yj2sn 822 47 with with IN cord-276598-tm0yj2sn 822 48 phenylboronic phenylboronic JJ cord-276598-tm0yj2sn 822 49 acid acid NN cord-276598-tm0yj2sn 822 50 - - HYPH cord-276598-tm0yj2sn 822 51 based base VBN cord-276598-tm0yj2sn 822 52 substrates substrate NNS cord-276598-tm0yj2sn 822 53 , , , cord-276598-tm0yj2sn 822 54 based base VBN cord-276598-tm0yj2sn 822 55 on on IN cord-276598-tm0yj2sn 822 56 the the DT cord-276598-tm0yj2sn 822 57 exchange exchange NN cord-276598-tm0yj2sn 822 58 of of IN cord-276598-tm0yj2sn 822 59 ligands ligand NNS cord-276598-tm0yj2sn 822 60 as as IN cord-276598-tm0yj2sn 822 61 in in IN cord-276598-tm0yj2sn 822 62 the the DT cord-276598-tm0yj2sn 822 63 first first JJ cord-276598-tm0yj2sn 822 64 step step NN cord-276598-tm0yj2sn 822 65 . . . cord-276598-tm0yj2sn 823 1 Molecules molecule NNS cord-276598-tm0yj2sn 823 2 2020 2020 CD cord-276598-tm0yj2sn 823 3 , , , cord-276598-tm0yj2sn 823 4 25 25 CD cord-276598-tm0yj2sn 823 5 , , , cord-276598-tm0yj2sn 823 6 x x NN cord-276598-tm0yj2sn 823 7 FOR for IN cord-276598-tm0yj2sn 823 8 PEER peer NN cord-276598-tm0yj2sn 823 9 REVIEW REVIEW NNP cord-276598-tm0yj2sn 823 10 25 25 CD cord-276598-tm0yj2sn 823 11 of of IN cord-276598-tm0yj2sn 823 12 37 37 CD cord-276598-tm0yj2sn 823 13 Scheme Scheme NNP cord-276598-tm0yj2sn 823 14 30 30 CD cord-276598-tm0yj2sn 823 15 . . . cord-276598-tm0yj2sn 824 1 Proposed propose VBN cord-276598-tm0yj2sn 824 2 mechanism mechanism NN cord-276598-tm0yj2sn 824 3 of of IN cord-276598-tm0yj2sn 824 4 the the DT cord-276598-tm0yj2sn 824 5 Cu cu JJ cord-276598-tm0yj2sn 824 6 - - HYPH cord-276598-tm0yj2sn 824 7 catalyzed catalyzed JJ cord-276598-tm0yj2sn 824 8 synthesis synthesis NN cord-276598-tm0yj2sn 824 9 of of IN cord-276598-tm0yj2sn 824 10 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 824 11 from from IN cord-276598-tm0yj2sn 824 12 phenylboronic phenylboronic NNP cord-276598-tm0yj2sn 824 13 acid acid NNP cord-276598-tm0yj2sn 824 14 / / SYM cord-276598-tm0yj2sn 824 15 ester ester NN cord-276598-tm0yj2sn 824 16 - - HYPH cord-276598-tm0yj2sn 824 17 based base VBN cord-276598-tm0yj2sn 824 18 substrates substrate NNS cord-276598-tm0yj2sn 824 19 and and CC cord-276598-tm0yj2sn 824 20 trialkyl trialkyl NNP cord-276598-tm0yj2sn 824 21 phosphite phosphite NNP cord-276598-tm0yj2sn 824 22 . . . cord-276598-tm0yj2sn 825 1 In in IN cord-276598-tm0yj2sn 825 2 a a DT cord-276598-tm0yj2sn 825 3 suggested suggest VBN cord-276598-tm0yj2sn 825 4 mechanism mechanism NN cord-276598-tm0yj2sn 825 5 for for IN cord-276598-tm0yj2sn 825 6 the the DT cord-276598-tm0yj2sn 825 7 organophotocatalytic organophotocatalytic JJ cord-276598-tm0yj2sn 825 8 synthesis synthesis NN cord-276598-tm0yj2sn 825 9 of of IN cord-276598-tm0yj2sn 825 10 P P NNP cord-276598-tm0yj2sn 825 11 - - HYPH cord-276598-tm0yj2sn 825 12 N N NNP cord-276598-tm0yj2sn 825 13 , , , cord-276598-tm0yj2sn 825 14 a a DT cord-276598-tm0yj2sn 825 15 photon photon NN cord-276598-tm0yj2sn 825 16 from from IN cord-276598-tm0yj2sn 825 17 the the DT cord-276598-tm0yj2sn 825 18 visible visible JJ cord-276598-tm0yj2sn 825 19 light light JJ cord-276598-tm0yj2sn 825 20 source source NN cord-276598-tm0yj2sn 825 21 is be VBZ cord-276598-tm0yj2sn 825 22 absorbed absorb VBN cord-276598-tm0yj2sn 825 23 by by IN cord-276598-tm0yj2sn 825 24 the the DT cord-276598-tm0yj2sn 825 25 organic organic JJ cord-276598-tm0yj2sn 825 26 dye dye NN cord-276598-tm0yj2sn 825 27 to to TO cord-276598-tm0yj2sn 825 28 become become VB cord-276598-tm0yj2sn 825 29 an an DT cord-276598-tm0yj2sn 825 30 excited excited JJ cord-276598-tm0yj2sn 825 31 radical radical JJ cord-276598-tm0yj2sn 825 32 ( ( -LRB- cord-276598-tm0yj2sn 825 33 Scheme scheme NN cord-276598-tm0yj2sn 825 34 31 31 CD cord-276598-tm0yj2sn 825 35 ) ) -RRB- cord-276598-tm0yj2sn 825 36 [ [ -LRB- cord-276598-tm0yj2sn 825 37 110 110 CD cord-276598-tm0yj2sn 825 38 ] ] -RRB- cord-276598-tm0yj2sn 825 39 . . . cord-276598-tm0yj2sn 826 1 By by IN cord-276598-tm0yj2sn 826 2 a a DT cord-276598-tm0yj2sn 826 3 single single JJ cord-276598-tm0yj2sn 826 4 - - HYPH cord-276598-tm0yj2sn 826 5 electron electron NN cord-276598-tm0yj2sn 826 6 transfer transfer NN cord-276598-tm0yj2sn 826 7 process process NN cord-276598-tm0yj2sn 826 8 , , , cord-276598-tm0yj2sn 826 9 the the DT cord-276598-tm0yj2sn 826 10 excited excited JJ cord-276598-tm0yj2sn 826 11 dye dye NN cord-276598-tm0yj2sn 826 12 - - HYPH cord-276598-tm0yj2sn 826 13 radical radical JJ cord-276598-tm0yj2sn 826 14 abstracts abstract NNS cord-276598-tm0yj2sn 826 15 an an DT cord-276598-tm0yj2sn 826 16 electron electron NN cord-276598-tm0yj2sn 826 17 from from IN cord-276598-tm0yj2sn 826 18 the the DT cord-276598-tm0yj2sn 826 19 N n CD cord-276598-tm0yj2sn 826 20 atom atom NN cord-276598-tm0yj2sn 826 21 of of IN cord-276598-tm0yj2sn 826 22 the the DT cord-276598-tm0yj2sn 826 23 amine amine NN cord-276598-tm0yj2sn 826 24 to to TO cord-276598-tm0yj2sn 826 25 form form VB cord-276598-tm0yj2sn 826 26 an an DT cord-276598-tm0yj2sn 826 27 anionic anionic JJ cord-276598-tm0yj2sn 826 28 dye dye NN cord-276598-tm0yj2sn 826 29 radical radical JJ cord-276598-tm0yj2sn 826 30 and and CC cord-276598-tm0yj2sn 826 31 cationic cationic JJ cord-276598-tm0yj2sn 826 32 amine amine NN cord-276598-tm0yj2sn 826 33 radical radical JJ cord-276598-tm0yj2sn 826 34 . . . cord-276598-tm0yj2sn 827 1 In in IN cord-276598-tm0yj2sn 827 2 the the DT cord-276598-tm0yj2sn 827 3 presence presence NN cord-276598-tm0yj2sn 827 4 of of IN cord-276598-tm0yj2sn 827 5 O2 O2 NNP cord-276598-tm0yj2sn 827 6 , , , cord-276598-tm0yj2sn 827 7 the the DT cord-276598-tm0yj2sn 827 8 anionic anionic JJ cord-276598-tm0yj2sn 827 9 dye dye NN cord-276598-tm0yj2sn 827 10 radical radical JJ cord-276598-tm0yj2sn 827 11 is be VBZ cord-276598-tm0yj2sn 827 12 reoxidized reoxidize VBN cord-276598-tm0yj2sn 827 13 to to IN cord-276598-tm0yj2sn 827 14 the the DT cord-276598-tm0yj2sn 827 15 organic organic JJ cord-276598-tm0yj2sn 827 16 dye dye NN cord-276598-tm0yj2sn 827 17 , , , cord-276598-tm0yj2sn 827 18 while while IN cord-276598-tm0yj2sn 827 19 the the DT cord-276598-tm0yj2sn 827 20 anionic anionic JJ cord-276598-tm0yj2sn 827 21 superoxide superoxide NN cord-276598-tm0yj2sn 827 22 that that WDT cord-276598-tm0yj2sn 827 23 is be VBZ cord-276598-tm0yj2sn 827 24 formed form VBN cord-276598-tm0yj2sn 827 25 in in IN cord-276598-tm0yj2sn 827 26 the the DT cord-276598-tm0yj2sn 827 27 process process NN cord-276598-tm0yj2sn 827 28 reacts react VBZ cord-276598-tm0yj2sn 827 29 with with IN cord-276598-tm0yj2sn 827 30 diethyl diethyl NNP cord-276598-tm0yj2sn 827 31 H H NNP cord-276598-tm0yj2sn 827 32 - - HYPH cord-276598-tm0yj2sn 827 33 phosphonate phosphonate NNP cord-276598-tm0yj2sn 827 34 ( ( -LRB- cord-276598-tm0yj2sn 827 35 H h NN cord-276598-tm0yj2sn 827 36 - - HYPH cord-276598-tm0yj2sn 827 37 P p NN cord-276598-tm0yj2sn 827 38 ) ) -RRB- cord-276598-tm0yj2sn 827 39 to to TO cord-276598-tm0yj2sn 827 40 generate generate VB cord-276598-tm0yj2sn 827 41 anionic anionic JJ cord-276598-tm0yj2sn 827 42 hydrogen hydrogen NN cord-276598-tm0yj2sn 827 43 peroxide peroxide NN cord-276598-tm0yj2sn 827 44 and and CC cord-276598-tm0yj2sn 827 45 a a DT cord-276598-tm0yj2sn 827 46 diethyl diethyl NN cord-276598-tm0yj2sn 827 47 phosphoryl phosphoryl NNP cord-276598-tm0yj2sn 827 48 radical radical JJ cord-276598-tm0yj2sn 827 49 . . . cord-276598-tm0yj2sn 828 1 Then then RB cord-276598-tm0yj2sn 828 2 , , , cord-276598-tm0yj2sn 828 3 the the DT cord-276598-tm0yj2sn 828 4 radical radical JJ cord-276598-tm0yj2sn 828 5 reacts react VBZ cord-276598-tm0yj2sn 828 6 with with IN cord-276598-tm0yj2sn 828 7 the the DT cord-276598-tm0yj2sn 828 8 cationic cationic JJ cord-276598-tm0yj2sn 828 9 - - HYPH cord-276598-tm0yj2sn 828 10 amine amine NN cord-276598-tm0yj2sn 828 11 radical radical JJ cord-276598-tm0yj2sn 828 12 to to TO cord-276598-tm0yj2sn 828 13 form form VB cord-276598-tm0yj2sn 828 14 a a DT cord-276598-tm0yj2sn 828 15 protonated protonated JJ cord-276598-tm0yj2sn 828 16 P p NN cord-276598-tm0yj2sn 828 17 - - HYPH cord-276598-tm0yj2sn 828 18 N N NNP cord-276598-tm0yj2sn 828 19 , , , cord-276598-tm0yj2sn 828 20 which which WDT cord-276598-tm0yj2sn 828 21 is be VBZ cord-276598-tm0yj2sn 828 22 then then RB cord-276598-tm0yj2sn 828 23 deprotonated deprotonate VBN cord-276598-tm0yj2sn 828 24 by by IN cord-276598-tm0yj2sn 828 25 the the DT cord-276598-tm0yj2sn 828 26 anionic anionic JJ cord-276598-tm0yj2sn 828 27 hydrogen hydrogen NN cord-276598-tm0yj2sn 828 28 peroxide peroxide NN cord-276598-tm0yj2sn 828 29 . . . cord-276598-tm0yj2sn 829 1 The the DT cord-276598-tm0yj2sn 829 2 authors author NNS cord-276598-tm0yj2sn 829 3 reported report VBD cord-276598-tm0yj2sn 829 4 that that IN cord-276598-tm0yj2sn 829 5 after after IN cord-276598-tm0yj2sn 829 6 an an DT cord-276598-tm0yj2sn 829 7 initial initial JJ cord-276598-tm0yj2sn 829 8 74 74 CD cord-276598-tm0yj2sn 829 9 % % NN cord-276598-tm0yj2sn 829 10 isolated isolated JJ cord-276598-tm0yj2sn 829 11 product product NN cord-276598-tm0yj2sn 829 12 , , , cord-276598-tm0yj2sn 829 13 the the DT cord-276598-tm0yj2sn 829 14 organic organic JJ cord-276598-tm0yj2sn 829 15 dye dye NN cord-276598-tm0yj2sn 829 16 catalyst catalyst NN cord-276598-tm0yj2sn 829 17 was be VBD cord-276598-tm0yj2sn 829 18 recycled recycle VBN cord-276598-tm0yj2sn 829 19 a a DT cord-276598-tm0yj2sn 829 20 second second JJ cord-276598-tm0yj2sn 829 21 time time NN cord-276598-tm0yj2sn 829 22 using use VBG cord-276598-tm0yj2sn 829 23 an an DT cord-276598-tm0yj2sn 829 24 acid acid NN cord-276598-tm0yj2sn 829 25 - - HYPH cord-276598-tm0yj2sn 829 26 base base NN cord-276598-tm0yj2sn 829 27 extraction extraction NN cord-276598-tm0yj2sn 829 28 , , , cord-276598-tm0yj2sn 829 29 and and CC cord-276598-tm0yj2sn 829 30 67 67 CD cord-276598-tm0yj2sn 829 31 % % NN cord-276598-tm0yj2sn 829 32 isolated isolated JJ cord-276598-tm0yj2sn 829 33 product product NN cord-276598-tm0yj2sn 829 34 was be VBD cord-276598-tm0yj2sn 829 35 obtained obtain VBN cord-276598-tm0yj2sn 829 36 the the DT cord-276598-tm0yj2sn 829 37 second second JJ cord-276598-tm0yj2sn 829 38 time time NN cord-276598-tm0yj2sn 829 39 . . . cord-276598-tm0yj2sn 830 1 Scheme scheme NN cord-276598-tm0yj2sn 830 2 30 30 CD cord-276598-tm0yj2sn 830 3 . . . cord-276598-tm0yj2sn 831 1 Proposed propose VBN cord-276598-tm0yj2sn 831 2 mechanism mechanism NN cord-276598-tm0yj2sn 831 3 of of IN cord-276598-tm0yj2sn 831 4 the the DT cord-276598-tm0yj2sn 831 5 Cu cu JJ cord-276598-tm0yj2sn 831 6 - - HYPH cord-276598-tm0yj2sn 831 7 catalyzed catalyzed JJ cord-276598-tm0yj2sn 831 8 synthesis synthesis NN cord-276598-tm0yj2sn 831 9 of of IN cord-276598-tm0yj2sn 831 10 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 831 11 from from IN cord-276598-tm0yj2sn 831 12 phenylboronic phenylboronic NNP cord-276598-tm0yj2sn 831 13 acid acid NNP cord-276598-tm0yj2sn 831 14 / / SYM cord-276598-tm0yj2sn 831 15 ester ester NN cord-276598-tm0yj2sn 831 16 - - HYPH cord-276598-tm0yj2sn 831 17 based base VBN cord-276598-tm0yj2sn 831 18 substrates substrate NNS cord-276598-tm0yj2sn 831 19 and and CC cord-276598-tm0yj2sn 831 20 trialkyl trialkyl NNP cord-276598-tm0yj2sn 831 21 phosphite phosphite NNP cord-276598-tm0yj2sn 831 22 . . . cord-276598-tm0yj2sn 832 1 In in IN cord-276598-tm0yj2sn 832 2 a a DT cord-276598-tm0yj2sn 832 3 suggested suggest VBN cord-276598-tm0yj2sn 832 4 mechanism mechanism NN cord-276598-tm0yj2sn 832 5 for for IN cord-276598-tm0yj2sn 832 6 the the DT cord-276598-tm0yj2sn 832 7 organophotocatalytic organophotocatalytic JJ cord-276598-tm0yj2sn 832 8 synthesis synthesis NN cord-276598-tm0yj2sn 832 9 of of IN cord-276598-tm0yj2sn 832 10 P P NNP cord-276598-tm0yj2sn 832 11 - - HYPH cord-276598-tm0yj2sn 832 12 N N NNP cord-276598-tm0yj2sn 832 13 , , , cord-276598-tm0yj2sn 832 14 a a DT cord-276598-tm0yj2sn 832 15 photon photon NN cord-276598-tm0yj2sn 832 16 from from IN cord-276598-tm0yj2sn 832 17 the the DT cord-276598-tm0yj2sn 832 18 visible visible JJ cord-276598-tm0yj2sn 832 19 light light JJ cord-276598-tm0yj2sn 832 20 source source NN cord-276598-tm0yj2sn 832 21 is be VBZ cord-276598-tm0yj2sn 832 22 absorbed absorb VBN cord-276598-tm0yj2sn 832 23 by by IN cord-276598-tm0yj2sn 832 24 the the DT cord-276598-tm0yj2sn 832 25 organic organic JJ cord-276598-tm0yj2sn 832 26 dye dye NN cord-276598-tm0yj2sn 832 27 to to TO cord-276598-tm0yj2sn 832 28 become become VB cord-276598-tm0yj2sn 832 29 an an DT cord-276598-tm0yj2sn 832 30 excited excited JJ cord-276598-tm0yj2sn 832 31 radical radical JJ cord-276598-tm0yj2sn 832 32 ( ( -LRB- cord-276598-tm0yj2sn 832 33 Scheme scheme NN cord-276598-tm0yj2sn 832 34 31 31 CD cord-276598-tm0yj2sn 832 35 ) ) -RRB- cord-276598-tm0yj2sn 832 36 [ [ -LRB- cord-276598-tm0yj2sn 832 37 110 110 CD cord-276598-tm0yj2sn 832 38 ] ] -RRB- cord-276598-tm0yj2sn 832 39 . . . cord-276598-tm0yj2sn 833 1 By by IN cord-276598-tm0yj2sn 833 2 a a DT cord-276598-tm0yj2sn 833 3 single single JJ cord-276598-tm0yj2sn 833 4 - - HYPH cord-276598-tm0yj2sn 833 5 electron electron NN cord-276598-tm0yj2sn 833 6 transfer transfer NN cord-276598-tm0yj2sn 833 7 process process NN cord-276598-tm0yj2sn 833 8 , , , cord-276598-tm0yj2sn 833 9 the the DT cord-276598-tm0yj2sn 833 10 excited excited JJ cord-276598-tm0yj2sn 833 11 dye dye NN cord-276598-tm0yj2sn 833 12 - - HYPH cord-276598-tm0yj2sn 833 13 radical radical JJ cord-276598-tm0yj2sn 833 14 abstracts abstract NNS cord-276598-tm0yj2sn 833 15 an an DT cord-276598-tm0yj2sn 833 16 electron electron NN cord-276598-tm0yj2sn 833 17 from from IN cord-276598-tm0yj2sn 833 18 the the DT cord-276598-tm0yj2sn 833 19 N n CD cord-276598-tm0yj2sn 833 20 atom atom NN cord-276598-tm0yj2sn 833 21 of of IN cord-276598-tm0yj2sn 833 22 the the DT cord-276598-tm0yj2sn 833 23 amine amine NN cord-276598-tm0yj2sn 833 24 to to TO cord-276598-tm0yj2sn 833 25 form form VB cord-276598-tm0yj2sn 833 26 an an DT cord-276598-tm0yj2sn 833 27 anionic anionic JJ cord-276598-tm0yj2sn 833 28 dye dye NN cord-276598-tm0yj2sn 833 29 radical radical JJ cord-276598-tm0yj2sn 833 30 and and CC cord-276598-tm0yj2sn 833 31 cationic cationic JJ cord-276598-tm0yj2sn 833 32 amine amine NN cord-276598-tm0yj2sn 833 33 radical radical JJ cord-276598-tm0yj2sn 833 34 . . . cord-276598-tm0yj2sn 834 1 In in IN cord-276598-tm0yj2sn 834 2 the the DT cord-276598-tm0yj2sn 834 3 presence presence NN cord-276598-tm0yj2sn 834 4 of of IN cord-276598-tm0yj2sn 834 5 O o NN cord-276598-tm0yj2sn 834 6 2 2 CD cord-276598-tm0yj2sn 834 7 , , , cord-276598-tm0yj2sn 834 8 the the DT cord-276598-tm0yj2sn 834 9 anionic anionic JJ cord-276598-tm0yj2sn 834 10 dye dye NN cord-276598-tm0yj2sn 834 11 radical radical JJ cord-276598-tm0yj2sn 834 12 is be VBZ cord-276598-tm0yj2sn 834 13 reoxidized reoxidize VBN cord-276598-tm0yj2sn 834 14 to to IN cord-276598-tm0yj2sn 834 15 the the DT cord-276598-tm0yj2sn 834 16 organic organic JJ cord-276598-tm0yj2sn 834 17 dye dye NN cord-276598-tm0yj2sn 834 18 , , , cord-276598-tm0yj2sn 834 19 while while IN cord-276598-tm0yj2sn 834 20 the the DT cord-276598-tm0yj2sn 834 21 anionic anionic JJ cord-276598-tm0yj2sn 834 22 superoxide superoxide NN cord-276598-tm0yj2sn 834 23 that that WDT cord-276598-tm0yj2sn 834 24 is be VBZ cord-276598-tm0yj2sn 834 25 formed form VBN cord-276598-tm0yj2sn 834 26 in in IN cord-276598-tm0yj2sn 834 27 the the DT cord-276598-tm0yj2sn 834 28 process process NN cord-276598-tm0yj2sn 834 29 reacts react VBZ cord-276598-tm0yj2sn 834 30 with with IN cord-276598-tm0yj2sn 834 31 diethyl diethyl NNP cord-276598-tm0yj2sn 834 32 H H NNP cord-276598-tm0yj2sn 834 33 - - HYPH cord-276598-tm0yj2sn 834 34 phosphonate phosphonate NNP cord-276598-tm0yj2sn 834 35 ( ( -LRB- cord-276598-tm0yj2sn 834 36 H h NN cord-276598-tm0yj2sn 834 37 - - HYPH cord-276598-tm0yj2sn 834 38 P p NN cord-276598-tm0yj2sn 834 39 ) ) -RRB- cord-276598-tm0yj2sn 834 40 to to TO cord-276598-tm0yj2sn 834 41 generate generate VB cord-276598-tm0yj2sn 834 42 anionic anionic JJ cord-276598-tm0yj2sn 834 43 hydrogen hydrogen NN cord-276598-tm0yj2sn 834 44 peroxide peroxide NN cord-276598-tm0yj2sn 834 45 and and CC cord-276598-tm0yj2sn 834 46 a a DT cord-276598-tm0yj2sn 834 47 diethyl diethyl NN cord-276598-tm0yj2sn 834 48 phosphoryl phosphoryl NNP cord-276598-tm0yj2sn 834 49 radical radical JJ cord-276598-tm0yj2sn 834 50 . . . cord-276598-tm0yj2sn 835 1 Then then RB cord-276598-tm0yj2sn 835 2 , , , cord-276598-tm0yj2sn 835 3 the the DT cord-276598-tm0yj2sn 835 4 radical radical JJ cord-276598-tm0yj2sn 835 5 reacts react VBZ cord-276598-tm0yj2sn 835 6 with with IN cord-276598-tm0yj2sn 835 7 the the DT cord-276598-tm0yj2sn 835 8 cationic cationic JJ cord-276598-tm0yj2sn 835 9 - - HYPH cord-276598-tm0yj2sn 835 10 amine amine NN cord-276598-tm0yj2sn 835 11 radical radical JJ cord-276598-tm0yj2sn 835 12 to to TO cord-276598-tm0yj2sn 835 13 form form VB cord-276598-tm0yj2sn 835 14 a a DT cord-276598-tm0yj2sn 835 15 protonated protonated JJ cord-276598-tm0yj2sn 835 16 P p NN cord-276598-tm0yj2sn 835 17 - - HYPH cord-276598-tm0yj2sn 835 18 N N NNP cord-276598-tm0yj2sn 835 19 , , , cord-276598-tm0yj2sn 835 20 which which WDT cord-276598-tm0yj2sn 835 21 is be VBZ cord-276598-tm0yj2sn 835 22 then then RB cord-276598-tm0yj2sn 835 23 deprotonated deprotonate VBN cord-276598-tm0yj2sn 835 24 by by IN cord-276598-tm0yj2sn 835 25 the the DT cord-276598-tm0yj2sn 835 26 anionic anionic JJ cord-276598-tm0yj2sn 835 27 hydrogen hydrogen NN cord-276598-tm0yj2sn 835 28 peroxide peroxide NN cord-276598-tm0yj2sn 835 29 . . . cord-276598-tm0yj2sn 836 1 The the DT cord-276598-tm0yj2sn 836 2 authors author NNS cord-276598-tm0yj2sn 836 3 reported report VBD cord-276598-tm0yj2sn 836 4 that that IN cord-276598-tm0yj2sn 836 5 after after IN cord-276598-tm0yj2sn 836 6 an an DT cord-276598-tm0yj2sn 836 7 initial initial JJ cord-276598-tm0yj2sn 836 8 74 74 CD cord-276598-tm0yj2sn 836 9 % % NN cord-276598-tm0yj2sn 836 10 isolated isolated JJ cord-276598-tm0yj2sn 836 11 product product NN cord-276598-tm0yj2sn 836 12 , , , cord-276598-tm0yj2sn 836 13 the the DT cord-276598-tm0yj2sn 836 14 organic organic JJ cord-276598-tm0yj2sn 836 15 dye dye NN cord-276598-tm0yj2sn 836 16 catalyst catalyst NN cord-276598-tm0yj2sn 836 17 was be VBD cord-276598-tm0yj2sn 836 18 recycled recycle VBN cord-276598-tm0yj2sn 836 19 a a DT cord-276598-tm0yj2sn 836 20 second second JJ cord-276598-tm0yj2sn 836 21 time time NN cord-276598-tm0yj2sn 836 22 using use VBG cord-276598-tm0yj2sn 836 23 an an DT cord-276598-tm0yj2sn 836 24 acid acid NN cord-276598-tm0yj2sn 836 25 - - HYPH cord-276598-tm0yj2sn 836 26 base base NN cord-276598-tm0yj2sn 836 27 extraction extraction NN cord-276598-tm0yj2sn 836 28 , , , cord-276598-tm0yj2sn 836 29 and and CC cord-276598-tm0yj2sn 836 30 67 67 CD cord-276598-tm0yj2sn 836 31 % % NN cord-276598-tm0yj2sn 836 32 isolated isolated JJ cord-276598-tm0yj2sn 836 33 product product NN cord-276598-tm0yj2sn 836 34 was be VBD cord-276598-tm0yj2sn 836 35 obtained obtain VBN cord-276598-tm0yj2sn 836 36 the the DT cord-276598-tm0yj2sn 836 37 second second JJ cord-276598-tm0yj2sn 836 38 time time NN cord-276598-tm0yj2sn 836 39 . . . cord-276598-tm0yj2sn 837 1 the the DT cord-276598-tm0yj2sn 837 2 amine amine NN cord-276598-tm0yj2sn 837 3 to to TO cord-276598-tm0yj2sn 837 4 form form VB cord-276598-tm0yj2sn 837 5 an an DT cord-276598-tm0yj2sn 837 6 anionic anionic JJ cord-276598-tm0yj2sn 837 7 dye dye NN cord-276598-tm0yj2sn 837 8 radical radical JJ cord-276598-tm0yj2sn 837 9 and and CC cord-276598-tm0yj2sn 837 10 cationic cationic JJ cord-276598-tm0yj2sn 837 11 amine amine NN cord-276598-tm0yj2sn 837 12 radical radical JJ cord-276598-tm0yj2sn 837 13 . . . cord-276598-tm0yj2sn 838 1 In in IN cord-276598-tm0yj2sn 838 2 the the DT cord-276598-tm0yj2sn 838 3 presence presence NN cord-276598-tm0yj2sn 838 4 of of IN cord-276598-tm0yj2sn 838 5 O2 O2 NNP cord-276598-tm0yj2sn 838 6 , , , cord-276598-tm0yj2sn 838 7 the the DT cord-276598-tm0yj2sn 838 8 anionic anionic JJ cord-276598-tm0yj2sn 838 9 dye dye NN cord-276598-tm0yj2sn 838 10 radical radical JJ cord-276598-tm0yj2sn 838 11 is be VBZ cord-276598-tm0yj2sn 838 12 reoxidized reoxidize VBN cord-276598-tm0yj2sn 838 13 to to IN cord-276598-tm0yj2sn 838 14 the the DT cord-276598-tm0yj2sn 838 15 organic organic JJ cord-276598-tm0yj2sn 838 16 dye dye NN cord-276598-tm0yj2sn 838 17 , , , cord-276598-tm0yj2sn 838 18 while while IN cord-276598-tm0yj2sn 838 19 the the DT cord-276598-tm0yj2sn 838 20 anionic anionic JJ cord-276598-tm0yj2sn 838 21 superoxide superoxide NN cord-276598-tm0yj2sn 838 22 that that WDT cord-276598-tm0yj2sn 838 23 is be VBZ cord-276598-tm0yj2sn 838 24 formed form VBN cord-276598-tm0yj2sn 838 25 in in IN cord-276598-tm0yj2sn 838 26 the the DT cord-276598-tm0yj2sn 838 27 process process NN cord-276598-tm0yj2sn 838 28 reacts react VBZ cord-276598-tm0yj2sn 838 29 with with IN cord-276598-tm0yj2sn 838 30 diethyl diethyl NNP cord-276598-tm0yj2sn 838 31 H H NNP cord-276598-tm0yj2sn 838 32 - - HYPH cord-276598-tm0yj2sn 838 33 phosphonate phosphonate NNP cord-276598-tm0yj2sn 838 34 ( ( -LRB- cord-276598-tm0yj2sn 838 35 H h NN cord-276598-tm0yj2sn 838 36 - - HYPH cord-276598-tm0yj2sn 838 37 P p NN cord-276598-tm0yj2sn 838 38 ) ) -RRB- cord-276598-tm0yj2sn 838 39 to to TO cord-276598-tm0yj2sn 838 40 generate generate VB cord-276598-tm0yj2sn 838 41 anionic anionic JJ cord-276598-tm0yj2sn 838 42 hydrogen hydrogen NN cord-276598-tm0yj2sn 838 43 peroxide peroxide NN cord-276598-tm0yj2sn 838 44 and and CC cord-276598-tm0yj2sn 838 45 a a DT cord-276598-tm0yj2sn 838 46 diethyl diethyl NN cord-276598-tm0yj2sn 838 47 phosphoryl phosphoryl NNP cord-276598-tm0yj2sn 838 48 radical radical JJ cord-276598-tm0yj2sn 838 49 . . . cord-276598-tm0yj2sn 839 1 Then then RB cord-276598-tm0yj2sn 839 2 , , , cord-276598-tm0yj2sn 839 3 the the DT cord-276598-tm0yj2sn 839 4 radical radical JJ cord-276598-tm0yj2sn 839 5 reacts react VBZ cord-276598-tm0yj2sn 839 6 with with IN cord-276598-tm0yj2sn 839 7 the the DT cord-276598-tm0yj2sn 839 8 cationic cationic JJ cord-276598-tm0yj2sn 839 9 - - HYPH cord-276598-tm0yj2sn 839 10 amine amine NN cord-276598-tm0yj2sn 839 11 radical radical JJ cord-276598-tm0yj2sn 839 12 to to TO cord-276598-tm0yj2sn 839 13 form form VB cord-276598-tm0yj2sn 839 14 a a DT cord-276598-tm0yj2sn 839 15 protonated protonated JJ cord-276598-tm0yj2sn 839 16 P p NN cord-276598-tm0yj2sn 839 17 - - HYPH cord-276598-tm0yj2sn 839 18 N N NNP cord-276598-tm0yj2sn 839 19 , , , cord-276598-tm0yj2sn 839 20 which which WDT cord-276598-tm0yj2sn 839 21 is be VBZ cord-276598-tm0yj2sn 839 22 then then RB cord-276598-tm0yj2sn 839 23 deprotonated deprotonate VBN cord-276598-tm0yj2sn 839 24 by by IN cord-276598-tm0yj2sn 839 25 the the DT cord-276598-tm0yj2sn 839 26 anionic anionic JJ cord-276598-tm0yj2sn 839 27 hydrogen hydrogen NN cord-276598-tm0yj2sn 839 28 peroxide peroxide NN cord-276598-tm0yj2sn 839 29 . . . cord-276598-tm0yj2sn 840 1 The the DT cord-276598-tm0yj2sn 840 2 authors author NNS cord-276598-tm0yj2sn 840 3 reported report VBD cord-276598-tm0yj2sn 840 4 that that IN cord-276598-tm0yj2sn 840 5 after after IN cord-276598-tm0yj2sn 840 6 an an DT cord-276598-tm0yj2sn 840 7 initial initial JJ cord-276598-tm0yj2sn 840 8 74 74 CD cord-276598-tm0yj2sn 840 9 % % NN cord-276598-tm0yj2sn 840 10 isolated isolated JJ cord-276598-tm0yj2sn 840 11 product product NN cord-276598-tm0yj2sn 840 12 , , , cord-276598-tm0yj2sn 840 13 the the DT cord-276598-tm0yj2sn 840 14 organic organic JJ cord-276598-tm0yj2sn 840 15 dye dye NN cord-276598-tm0yj2sn 840 16 catalyst catalyst NN cord-276598-tm0yj2sn 840 17 was be VBD cord-276598-tm0yj2sn 840 18 recycled recycle VBN cord-276598-tm0yj2sn 840 19 a a DT cord-276598-tm0yj2sn 840 20 second second JJ cord-276598-tm0yj2sn 840 21 time time NN cord-276598-tm0yj2sn 840 22 using use VBG cord-276598-tm0yj2sn 840 23 an an DT cord-276598-tm0yj2sn 840 24 acid acid NN cord-276598-tm0yj2sn 840 25 - - HYPH cord-276598-tm0yj2sn 840 26 base base NN cord-276598-tm0yj2sn 840 27 extraction extraction NN cord-276598-tm0yj2sn 840 28 , , , cord-276598-tm0yj2sn 840 29 and and CC cord-276598-tm0yj2sn 840 30 67 67 CD cord-276598-tm0yj2sn 840 31 % % NN cord-276598-tm0yj2sn 840 32 isolated isolated JJ cord-276598-tm0yj2sn 840 33 product product NN cord-276598-tm0yj2sn 840 34 was be VBD cord-276598-tm0yj2sn 840 35 obtained obtain VBN cord-276598-tm0yj2sn 840 36 the the DT cord-276598-tm0yj2sn 840 37 second second JJ cord-276598-tm0yj2sn 840 38 time time NN cord-276598-tm0yj2sn 840 39 . . . cord-276598-tm0yj2sn 841 1 Proposed propose VBN cord-276598-tm0yj2sn 841 2 mechanism mechanism NN cord-276598-tm0yj2sn 841 3 for for IN cord-276598-tm0yj2sn 841 4 the the DT cord-276598-tm0yj2sn 841 5 visible visible JJ cord-276598-tm0yj2sn 841 6 light light NN cord-276598-tm0yj2sn 841 7 and and CC cord-276598-tm0yj2sn 841 8 organic organic JJ cord-276598-tm0yj2sn 841 9 dye dye NN cord-276598-tm0yj2sn 841 10 - - HYPH cord-276598-tm0yj2sn 841 11 catalyzed catalyze VBN cord-276598-tm0yj2sn 841 12 synthesis synthesis NN cord-276598-tm0yj2sn 841 13 of of IN cord-276598-tm0yj2sn 841 14 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 841 15 . . . cord-276598-tm0yj2sn 842 1 Proposed propose VBN cord-276598-tm0yj2sn 842 2 mechanism mechanism NN cord-276598-tm0yj2sn 842 3 for for IN cord-276598-tm0yj2sn 842 4 the the DT cord-276598-tm0yj2sn 842 5 visible visible JJ cord-276598-tm0yj2sn 842 6 light light NN cord-276598-tm0yj2sn 842 7 and and CC cord-276598-tm0yj2sn 842 8 organic organic JJ cord-276598-tm0yj2sn 842 9 dye dye NN cord-276598-tm0yj2sn 842 10 - - HYPH cord-276598-tm0yj2sn 842 11 catalyzed catalyze VBN cord-276598-tm0yj2sn 842 12 synthesis synthesis NN cord-276598-tm0yj2sn 842 13 of of IN cord-276598-tm0yj2sn 842 14 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 842 15 . . . cord-276598-tm0yj2sn 843 1 In in IN cord-276598-tm0yj2sn 843 2 the the DT cord-276598-tm0yj2sn 843 3 overall overall JJ cord-276598-tm0yj2sn 843 4 mechanism mechanism NN cord-276598-tm0yj2sn 843 5 suggested suggest VBN cord-276598-tm0yj2sn 843 6 for for IN cord-276598-tm0yj2sn 843 7 the the DT cord-276598-tm0yj2sn 843 8 alkali alkali NN cord-276598-tm0yj2sn 843 9 - - HYPH cord-276598-tm0yj2sn 843 10 metal metal NN cord-276598-tm0yj2sn 843 11 catalyzed catalyze VBN cord-276598-tm0yj2sn 843 12 oxidative oxidative JJ cord-276598-tm0yj2sn 843 13 cross cross JJ cord-276598-tm0yj2sn 843 14 - - JJ cord-276598-tm0yj2sn 843 15 coupling coupling JJ cord-276598-tm0yj2sn 843 16 reaction reaction NN cord-276598-tm0yj2sn 843 17 , , , cord-276598-tm0yj2sn 843 18 a a DT cord-276598-tm0yj2sn 843 19 phosphoryl phosphoryl NN cord-276598-tm0yj2sn 843 20 iodide iodide NN cord-276598-tm0yj2sn 843 21 intermediate intermediate JJ cord-276598-tm0yj2sn 843 22 and and CC cord-276598-tm0yj2sn 843 23 LiOH LiOH NNP cord-276598-tm0yj2sn 843 24 are be VBP cord-276598-tm0yj2sn 843 25 generated generate VBN cord-276598-tm0yj2sn 843 26 in in IN cord-276598-tm0yj2sn 843 27 the the DT cord-276598-tm0yj2sn 843 28 first first JJ cord-276598-tm0yj2sn 843 29 step step NN cord-276598-tm0yj2sn 843 30 from from IN cord-276598-tm0yj2sn 843 31 a a DT cord-276598-tm0yj2sn 843 32 reaction reaction NN cord-276598-tm0yj2sn 843 33 of of IN cord-276598-tm0yj2sn 843 34 LiI lii NN cord-276598-tm0yj2sn 843 35 and and CC cord-276598-tm0yj2sn 843 36 the the DT cord-276598-tm0yj2sn 843 37 H H NNP cord-276598-tm0yj2sn 843 38 - - HYPH cord-276598-tm0yj2sn 843 39 phosphonate phosphonate NNP cord-276598-tm0yj2sn 843 40 ( ( -LRB- cord-276598-tm0yj2sn 843 41 H h NN cord-276598-tm0yj2sn 843 42 - - HYPH cord-276598-tm0yj2sn 843 43 P P NNP cord-276598-tm0yj2sn 843 44 ) ) -RRB- cord-276598-tm0yj2sn 843 45 in in IN cord-276598-tm0yj2sn 843 46 the the DT cord-276598-tm0yj2sn 843 47 presence presence NN cord-276598-tm0yj2sn 843 48 of of IN cord-276598-tm0yj2sn 843 49 aq aq NNP cord-276598-tm0yj2sn 843 50 . . . cord-276598-tm0yj2sn 844 1 TBHP TBHP NNP cord-276598-tm0yj2sn 845 1 ( ( -LRB- cord-276598-tm0yj2sn 845 2 Scheme scheme NN cord-276598-tm0yj2sn 845 3 32 32 CD cord-276598-tm0yj2sn 845 4 ) ) -RRB- cord-276598-tm0yj2sn 845 5 [ [ -LRB- cord-276598-tm0yj2sn 845 6 111 111 CD cord-276598-tm0yj2sn 845 7 ] ] -RRB- cord-276598-tm0yj2sn 845 8 . . . cord-276598-tm0yj2sn 846 1 The the DT cord-276598-tm0yj2sn 846 2 second second JJ cord-276598-tm0yj2sn 846 3 step step NN cord-276598-tm0yj2sn 846 4 involves involve VBZ cord-276598-tm0yj2sn 846 5 the the DT cord-276598-tm0yj2sn 846 6 removal removal NN cord-276598-tm0yj2sn 846 7 of of IN cord-276598-tm0yj2sn 846 8 a a DT cord-276598-tm0yj2sn 846 9 proton proton NN cord-276598-tm0yj2sn 846 10 from from IN cord-276598-tm0yj2sn 846 11 the the DT cord-276598-tm0yj2sn 846 12 amine amine NN cord-276598-tm0yj2sn 846 13 by by IN cord-276598-tm0yj2sn 846 14 the the DT cord-276598-tm0yj2sn 846 15 LiOH lioh NN cord-276598-tm0yj2sn 846 16 to to TO cord-276598-tm0yj2sn 846 17 form form VB cord-276598-tm0yj2sn 846 18 lithium lithium NN cord-276598-tm0yj2sn 846 19 amide amide NN cord-276598-tm0yj2sn 846 20 and and CC cord-276598-tm0yj2sn 846 21 H h NN cord-276598-tm0yj2sn 846 22 2 2 CD cord-276598-tm0yj2sn 846 23 O o NN cord-276598-tm0yj2sn 846 24 , , , cord-276598-tm0yj2sn 846 25 and and CC cord-276598-tm0yj2sn 846 26 the the DT cord-276598-tm0yj2sn 846 27 desired desire VBN cord-276598-tm0yj2sn 846 28 product product NN cord-276598-tm0yj2sn 846 29 is be VBZ cord-276598-tm0yj2sn 846 30 formed form VBN cord-276598-tm0yj2sn 846 31 in in IN cord-276598-tm0yj2sn 846 32 the the DT cord-276598-tm0yj2sn 846 33 final final JJ cord-276598-tm0yj2sn 846 34 step step NN cord-276598-tm0yj2sn 846 35 from from IN cord-276598-tm0yj2sn 846 36 the the DT cord-276598-tm0yj2sn 846 37 reaction reaction NN cord-276598-tm0yj2sn 846 38 of of IN cord-276598-tm0yj2sn 846 39 phosphoryl phosphoryl NN cord-276598-tm0yj2sn 846 40 iodide iodide NN cord-276598-tm0yj2sn 846 41 and and CC cord-276598-tm0yj2sn 846 42 lithium lithium NN cord-276598-tm0yj2sn 846 43 amide amide NN cord-276598-tm0yj2sn 846 44 . . . cord-276598-tm0yj2sn 846 45 _SP cord-276598-tm0yj2sn 847 1 In in IN cord-276598-tm0yj2sn 847 2 the the DT cord-276598-tm0yj2sn 847 3 overall overall JJ cord-276598-tm0yj2sn 847 4 mechanism mechanism NN cord-276598-tm0yj2sn 847 5 suggested suggest VBN cord-276598-tm0yj2sn 847 6 for for IN cord-276598-tm0yj2sn 847 7 the the DT cord-276598-tm0yj2sn 847 8 alkali alkali NN cord-276598-tm0yj2sn 847 9 - - HYPH cord-276598-tm0yj2sn 847 10 metal metal NN cord-276598-tm0yj2sn 847 11 catalyzed catalyze VBN cord-276598-tm0yj2sn 847 12 oxidative oxidative JJ cord-276598-tm0yj2sn 847 13 cross cross JJ cord-276598-tm0yj2sn 847 14 - - JJ cord-276598-tm0yj2sn 847 15 coupling coupling JJ cord-276598-tm0yj2sn 847 16 reaction reaction NN cord-276598-tm0yj2sn 847 17 , , , cord-276598-tm0yj2sn 847 18 a a DT cord-276598-tm0yj2sn 847 19 phosphoryl phosphoryl NN cord-276598-tm0yj2sn 847 20 iodide iodide NN cord-276598-tm0yj2sn 847 21 intermediate intermediate JJ cord-276598-tm0yj2sn 847 22 and and CC cord-276598-tm0yj2sn 847 23 LiOH LiOH NNP cord-276598-tm0yj2sn 847 24 are be VBP cord-276598-tm0yj2sn 847 25 generated generate VBN cord-276598-tm0yj2sn 847 26 in in IN cord-276598-tm0yj2sn 847 27 the the DT cord-276598-tm0yj2sn 847 28 first first JJ cord-276598-tm0yj2sn 847 29 step step NN cord-276598-tm0yj2sn 847 30 from from IN cord-276598-tm0yj2sn 847 31 a a DT cord-276598-tm0yj2sn 847 32 reaction reaction NN cord-276598-tm0yj2sn 847 33 of of IN cord-276598-tm0yj2sn 847 34 LiI lii NN cord-276598-tm0yj2sn 847 35 and and CC cord-276598-tm0yj2sn 847 36 the the DT cord-276598-tm0yj2sn 847 37 H H NNP cord-276598-tm0yj2sn 847 38 - - HYPH cord-276598-tm0yj2sn 847 39 phosphonate phosphonate NNP cord-276598-tm0yj2sn 847 40 ( ( -LRB- cord-276598-tm0yj2sn 847 41 H h NN cord-276598-tm0yj2sn 847 42 - - HYPH cord-276598-tm0yj2sn 847 43 P P NNP cord-276598-tm0yj2sn 847 44 ) ) -RRB- cord-276598-tm0yj2sn 847 45 in in IN cord-276598-tm0yj2sn 847 46 the the DT cord-276598-tm0yj2sn 847 47 presence presence NN cord-276598-tm0yj2sn 847 48 of of IN cord-276598-tm0yj2sn 847 49 aq aq NNP cord-276598-tm0yj2sn 847 50 . . . cord-276598-tm0yj2sn 848 1 TBHP TBHP NNP cord-276598-tm0yj2sn 849 1 ( ( -LRB- cord-276598-tm0yj2sn 849 2 Scheme scheme NN cord-276598-tm0yj2sn 849 3 32 32 CD cord-276598-tm0yj2sn 849 4 ) ) -RRB- cord-276598-tm0yj2sn 849 5 [ [ -LRB- cord-276598-tm0yj2sn 849 6 111 111 CD cord-276598-tm0yj2sn 849 7 ] ] -RRB- cord-276598-tm0yj2sn 849 8 . . . cord-276598-tm0yj2sn 850 1 The the DT cord-276598-tm0yj2sn 850 2 second second JJ cord-276598-tm0yj2sn 850 3 step step NN cord-276598-tm0yj2sn 850 4 involves involve VBZ cord-276598-tm0yj2sn 850 5 the the DT cord-276598-tm0yj2sn 850 6 removal removal NN cord-276598-tm0yj2sn 850 7 of of IN cord-276598-tm0yj2sn 850 8 a a DT cord-276598-tm0yj2sn 850 9 proton proton NN cord-276598-tm0yj2sn 850 10 from from IN cord-276598-tm0yj2sn 850 11 the the DT cord-276598-tm0yj2sn 850 12 amine amine NN cord-276598-tm0yj2sn 850 13 by by IN cord-276598-tm0yj2sn 850 14 the the DT cord-276598-tm0yj2sn 850 15 LiOH lioh NN cord-276598-tm0yj2sn 850 16 to to TO cord-276598-tm0yj2sn 850 17 form form VB cord-276598-tm0yj2sn 850 18 lithium lithium NN cord-276598-tm0yj2sn 850 19 amide amide NN cord-276598-tm0yj2sn 850 20 and and CC cord-276598-tm0yj2sn 850 21 H2O h2o NN cord-276598-tm0yj2sn 850 22 , , , cord-276598-tm0yj2sn 850 23 and and CC cord-276598-tm0yj2sn 850 24 the the DT cord-276598-tm0yj2sn 850 25 desired desire VBN cord-276598-tm0yj2sn 850 26 product product NN cord-276598-tm0yj2sn 850 27 is be VBZ cord-276598-tm0yj2sn 850 28 formed form VBN cord-276598-tm0yj2sn 850 29 in in IN cord-276598-tm0yj2sn 850 30 the the DT cord-276598-tm0yj2sn 850 31 final final JJ cord-276598-tm0yj2sn 850 32 step step NN cord-276598-tm0yj2sn 850 33 from from IN cord-276598-tm0yj2sn 850 34 the the DT cord-276598-tm0yj2sn 850 35 reaction reaction NN cord-276598-tm0yj2sn 850 36 of of IN cord-276598-tm0yj2sn 850 37 phosphoryl phosphoryl NN cord-276598-tm0yj2sn 850 38 iodide iodide NN cord-276598-tm0yj2sn 850 39 and and CC cord-276598-tm0yj2sn 850 40 lithium lithium NN cord-276598-tm0yj2sn 850 41 amide amide NN cord-276598-tm0yj2sn 850 42 . . . cord-276598-tm0yj2sn 851 1 Scheme scheme NN cord-276598-tm0yj2sn 851 2 32 32 CD cord-276598-tm0yj2sn 851 3 . . . cord-276598-tm0yj2sn 852 1 Proposed propose VBN cord-276598-tm0yj2sn 852 2 mechanism mechanism NN cord-276598-tm0yj2sn 852 3 for for IN cord-276598-tm0yj2sn 852 4 the the DT cord-276598-tm0yj2sn 852 5 synthesis synthesis NN cord-276598-tm0yj2sn 852 6 of of IN cord-276598-tm0yj2sn 852 7 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 852 8 using use VBG cord-276598-tm0yj2sn 852 9 alkali alkali NN cord-276598-tm0yj2sn 852 10 - - HYPH cord-276598-tm0yj2sn 852 11 metal metal NN cord-276598-tm0yj2sn 852 12 catalyst catalyst NN cord-276598-tm0yj2sn 852 13 . . . cord-276598-tm0yj2sn 853 1 The the DT cord-276598-tm0yj2sn 853 2 mechanism mechanism NN cord-276598-tm0yj2sn 853 3 of of IN cord-276598-tm0yj2sn 853 4 the the DT cord-276598-tm0yj2sn 853 5 reaction reaction NN cord-276598-tm0yj2sn 853 6 of of IN cord-276598-tm0yj2sn 853 7 nitrene nitrene JJ cord-276598-tm0yj2sn 853 8 insertion insertion NN cord-276598-tm0yj2sn 853 9 according accord VBG cord-276598-tm0yj2sn 853 10 to to IN cord-276598-tm0yj2sn 853 11 Chang Chang NNP cord-276598-tm0yj2sn 853 12 , , , cord-276598-tm0yj2sn 853 13 Kim Kim NNP cord-276598-tm0yj2sn 853 14 , , , cord-276598-tm0yj2sn 853 15 and and CC cord-276598-tm0yj2sn 853 16 coworkers coworker NNS cord-276598-tm0yj2sn 853 17 follows follow VBZ cord-276598-tm0yj2sn 853 18 activation activation NN cord-276598-tm0yj2sn 853 19 of of IN cord-276598-tm0yj2sn 853 20 the the DT cord-276598-tm0yj2sn 853 21 C C NNP cord-276598-tm0yj2sn 853 22 - - HYPH cord-276598-tm0yj2sn 853 23 H h NN cord-276598-tm0yj2sn 853 24 bond bond NN cord-276598-tm0yj2sn 853 25 cleavage cleavage NN cord-276598-tm0yj2sn 853 26 on on IN cord-276598-tm0yj2sn 853 27 the the DT cord-276598-tm0yj2sn 853 28 amide amide NN cord-276598-tm0yj2sn 853 29 or or CC cord-276598-tm0yj2sn 853 30 ketone ketone NN cord-276598-tm0yj2sn 853 31 substrate substrate NN cord-276598-tm0yj2sn 853 32 by by IN cord-276598-tm0yj2sn 853 33 the the DT cord-276598-tm0yj2sn 853 34 Ir Ir NNP cord-276598-tm0yj2sn 853 35 ( ( -LRB- cord-276598-tm0yj2sn 853 36 III III NNP cord-276598-tm0yj2sn 853 37 ) ) -RRB- cord-276598-tm0yj2sn 853 38 -based -based JJ cord-276598-tm0yj2sn 853 39 catalyst catalyst NN cord-276598-tm0yj2sn 853 40 to to TO cord-276598-tm0yj2sn 853 41 generate generate VB cord-276598-tm0yj2sn 853 42 an an DT cord-276598-tm0yj2sn 853 43 iridacyclic iridacyclic JJ cord-276598-tm0yj2sn 853 44 intermediate intermediate NN cord-276598-tm0yj2sn 853 45 , , , cord-276598-tm0yj2sn 853 46 which which WDT cord-276598-tm0yj2sn 853 47 then then RB cord-276598-tm0yj2sn 853 48 reacts react VBZ cord-276598-tm0yj2sn 853 49 with with IN cord-276598-tm0yj2sn 853 50 the the DT cord-276598-tm0yj2sn 853 51 phosphoryl phosphoryl NNS cord-276598-tm0yj2sn 853 52 azide azide NN cord-276598-tm0yj2sn 853 53 to to TO cord-276598-tm0yj2sn 853 54 produce produce VB cord-276598-tm0yj2sn 853 55 a a DT cord-276598-tm0yj2sn 853 56 coordinated coordinated JJ cord-276598-tm0yj2sn 853 57 phosphoryl phosphoryl NN cord-276598-tm0yj2sn 853 58 azide azide NN cord-276598-tm0yj2sn 853 59 - - HYPH cord-276598-tm0yj2sn 853 60 iridacyclic iridacyclic JJ cord-276598-tm0yj2sn 853 61 adduct adduct NN cord-276598-tm0yj2sn 853 62 ( ( -LRB- cord-276598-tm0yj2sn 853 63 Scheme Scheme NNP cord-276598-tm0yj2sn 853 64 33 33 CD cord-276598-tm0yj2sn 853 65 ) ) -RRB- cord-276598-tm0yj2sn 853 66 [ [ -LRB- cord-276598-tm0yj2sn 853 67 112 112 CD cord-276598-tm0yj2sn 853 68 ] ] -RRB- cord-276598-tm0yj2sn 853 69 . . . cord-276598-tm0yj2sn 854 1 By by IN cord-276598-tm0yj2sn 854 2 intramolecular intramolecular JJ cord-276598-tm0yj2sn 854 3 migratory migratory JJ cord-276598-tm0yj2sn 854 4 insertion insertion NN cord-276598-tm0yj2sn 854 5 of of IN cord-276598-tm0yj2sn 854 6 C C NNP cord-276598-tm0yj2sn 854 7 - - HYPH cord-276598-tm0yj2sn 854 8 N N NNP cord-276598-tm0yj2sn 854 9 into into IN cord-276598-tm0yj2sn 854 10 the the DT cord-276598-tm0yj2sn 854 11 Ir Ir NNP cord-276598-tm0yj2sn 854 12 - - HYPH cord-276598-tm0yj2sn 854 13 C C NNP cord-276598-tm0yj2sn 854 14 bond bond NN cord-276598-tm0yj2sn 854 15 , , , cord-276598-tm0yj2sn 854 16 with with IN cord-276598-tm0yj2sn 854 17 removal removal NN cord-276598-tm0yj2sn 854 18 of of IN cord-276598-tm0yj2sn 854 19 N2 N2 NNP cord-276598-tm0yj2sn 854 20 , , , cord-276598-tm0yj2sn 854 21 or or CC cord-276598-tm0yj2sn 854 22 by by IN cord-276598-tm0yj2sn 854 23 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 854 24 attack attack NN cord-276598-tm0yj2sn 854 25 from from IN cord-276598-tm0yj2sn 854 26 the the DT cord-276598-tm0yj2sn 854 27 azide azide NN cord-276598-tm0yj2sn 854 28 group group NN cord-276598-tm0yj2sn 854 29 on on IN cord-276598-tm0yj2sn 854 30 the the DT cord-276598-tm0yj2sn 854 31 Ir Ir NNP cord-276598-tm0yj2sn 854 32 - - HYPH cord-276598-tm0yj2sn 854 33 C C NNP cord-276598-tm0yj2sn 854 34 bond bond NN cord-276598-tm0yj2sn 854 35 to to TO cord-276598-tm0yj2sn 854 36 form form VB cord-276598-tm0yj2sn 854 37 the the DT cord-276598-tm0yj2sn 854 38 C C NNP cord-276598-tm0yj2sn 854 39 - - HYPH cord-276598-tm0yj2sn 854 40 N N NNP cord-276598-tm0yj2sn 854 41 bond bond NN cord-276598-tm0yj2sn 854 42 with with IN cord-276598-tm0yj2sn 854 43 the the DT cord-276598-tm0yj2sn 854 44 elimination elimination NN cord-276598-tm0yj2sn 854 45 of of IN cord-276598-tm0yj2sn 854 46 N2 N2 NNP cord-276598-tm0yj2sn 854 47 , , , cord-276598-tm0yj2sn 854 48 a a DT cord-276598-tm0yj2sn 854 49 complex complex NN cord-276598-tm0yj2sn 854 50 of of IN cord-276598-tm0yj2sn 854 51 Ir Ir NNP cord-276598-tm0yj2sn 854 52 - - HYPH cord-276598-tm0yj2sn 854 53 N N NNP cord-276598-tm0yj2sn 854 54 - - HYPH cord-276598-tm0yj2sn 854 55 C C NNP cord-276598-tm0yj2sn 854 56 bond bond NN cord-276598-tm0yj2sn 854 57 is be VBZ cord-276598-tm0yj2sn 854 58 formed form VBN cord-276598-tm0yj2sn 854 59 . . . cord-276598-tm0yj2sn 855 1 Proto proto NN cord-276598-tm0yj2sn 855 2 - - HYPH cord-276598-tm0yj2sn 855 3 demetallation demetallation NN cord-276598-tm0yj2sn 855 4 of of IN cord-276598-tm0yj2sn 855 5 the the DT cord-276598-tm0yj2sn 855 6 Ir Ir NNP cord-276598-tm0yj2sn 855 7 ( ( -LRB- cord-276598-tm0yj2sn 855 8 III III NNP cord-276598-tm0yj2sn 855 9 ) ) -RRB- cord-276598-tm0yj2sn 856 1 -based -based JJ cord-276598-tm0yj2sn 856 2 catalyst catalyst NN cord-276598-tm0yj2sn 856 3 affords afford VBZ cord-276598-tm0yj2sn 856 4 the the DT cord-276598-tm0yj2sn 856 5 desired desire VBN cord-276598-tm0yj2sn 856 6 product product NN cord-276598-tm0yj2sn 856 7 while while IN cord-276598-tm0yj2sn 856 8 Scheme Scheme NNP cord-276598-tm0yj2sn 856 9 32 32 CD cord-276598-tm0yj2sn 856 10 . . . cord-276598-tm0yj2sn 857 1 Proposed propose VBN cord-276598-tm0yj2sn 857 2 mechanism mechanism NN cord-276598-tm0yj2sn 857 3 for for IN cord-276598-tm0yj2sn 857 4 the the DT cord-276598-tm0yj2sn 857 5 synthesis synthesis NN cord-276598-tm0yj2sn 857 6 of of IN cord-276598-tm0yj2sn 857 7 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 857 8 using use VBG cord-276598-tm0yj2sn 857 9 alkali alkali NN cord-276598-tm0yj2sn 857 10 - - HYPH cord-276598-tm0yj2sn 857 11 metal metal NN cord-276598-tm0yj2sn 857 12 catalyst catalyst NN cord-276598-tm0yj2sn 857 13 . . . cord-276598-tm0yj2sn 858 1 The the DT cord-276598-tm0yj2sn 858 2 mechanism mechanism NN cord-276598-tm0yj2sn 858 3 of of IN cord-276598-tm0yj2sn 858 4 the the DT cord-276598-tm0yj2sn 858 5 reaction reaction NN cord-276598-tm0yj2sn 858 6 of of IN cord-276598-tm0yj2sn 858 7 nitrene nitrene JJ cord-276598-tm0yj2sn 858 8 insertion insertion NN cord-276598-tm0yj2sn 858 9 according accord VBG cord-276598-tm0yj2sn 858 10 to to IN cord-276598-tm0yj2sn 858 11 Chang Chang NNP cord-276598-tm0yj2sn 858 12 , , , cord-276598-tm0yj2sn 858 13 Kim Kim NNP cord-276598-tm0yj2sn 858 14 , , , cord-276598-tm0yj2sn 858 15 and and CC cord-276598-tm0yj2sn 858 16 coworkers coworker NNS cord-276598-tm0yj2sn 858 17 follows follow VBZ cord-276598-tm0yj2sn 858 18 activation activation NN cord-276598-tm0yj2sn 858 19 of of IN cord-276598-tm0yj2sn 858 20 the the DT cord-276598-tm0yj2sn 858 21 C C NNP cord-276598-tm0yj2sn 858 22 - - HYPH cord-276598-tm0yj2sn 858 23 H h NN cord-276598-tm0yj2sn 858 24 bond bond NN cord-276598-tm0yj2sn 858 25 cleavage cleavage NN cord-276598-tm0yj2sn 858 26 on on IN cord-276598-tm0yj2sn 858 27 the the DT cord-276598-tm0yj2sn 858 28 amide amide NN cord-276598-tm0yj2sn 858 29 or or CC cord-276598-tm0yj2sn 858 30 ketone ketone NN cord-276598-tm0yj2sn 858 31 substrate substrate NN cord-276598-tm0yj2sn 858 32 by by IN cord-276598-tm0yj2sn 858 33 the the DT cord-276598-tm0yj2sn 858 34 Ir Ir NNP cord-276598-tm0yj2sn 858 35 ( ( -LRB- cord-276598-tm0yj2sn 858 36 III III NNP cord-276598-tm0yj2sn 858 37 ) ) -RRB- cord-276598-tm0yj2sn 858 38 -based -based JJ cord-276598-tm0yj2sn 858 39 catalyst catalyst NN cord-276598-tm0yj2sn 858 40 to to TO cord-276598-tm0yj2sn 858 41 generate generate VB cord-276598-tm0yj2sn 858 42 an an DT cord-276598-tm0yj2sn 858 43 iridacyclic iridacyclic JJ cord-276598-tm0yj2sn 858 44 intermediate intermediate NN cord-276598-tm0yj2sn 858 45 , , , cord-276598-tm0yj2sn 858 46 which which WDT cord-276598-tm0yj2sn 858 47 then then RB cord-276598-tm0yj2sn 858 48 reacts react VBZ cord-276598-tm0yj2sn 858 49 with with IN cord-276598-tm0yj2sn 858 50 the the DT cord-276598-tm0yj2sn 858 51 phosphoryl phosphoryl NNS cord-276598-tm0yj2sn 858 52 azide azide NN cord-276598-tm0yj2sn 858 53 to to TO cord-276598-tm0yj2sn 858 54 produce produce VB cord-276598-tm0yj2sn 858 55 a a DT cord-276598-tm0yj2sn 858 56 coordinated coordinated JJ cord-276598-tm0yj2sn 858 57 phosphoryl phosphoryl NN cord-276598-tm0yj2sn 858 58 azide azide NN cord-276598-tm0yj2sn 858 59 - - HYPH cord-276598-tm0yj2sn 858 60 iridacyclic iridacyclic JJ cord-276598-tm0yj2sn 858 61 adduct adduct NN cord-276598-tm0yj2sn 858 62 ( ( -LRB- cord-276598-tm0yj2sn 858 63 Scheme Scheme NNP cord-276598-tm0yj2sn 858 64 33 33 CD cord-276598-tm0yj2sn 858 65 ) ) -RRB- cord-276598-tm0yj2sn 858 66 [ [ -LRB- cord-276598-tm0yj2sn 858 67 112 112 CD cord-276598-tm0yj2sn 858 68 ] ] -RRB- cord-276598-tm0yj2sn 858 69 . . . cord-276598-tm0yj2sn 859 1 By by IN cord-276598-tm0yj2sn 859 2 intramolecular intramolecular JJ cord-276598-tm0yj2sn 859 3 migratory migratory JJ cord-276598-tm0yj2sn 859 4 insertion insertion NN cord-276598-tm0yj2sn 859 5 of of IN cord-276598-tm0yj2sn 859 6 C C NNP cord-276598-tm0yj2sn 859 7 - - HYPH cord-276598-tm0yj2sn 859 8 N N NNP cord-276598-tm0yj2sn 859 9 into into IN cord-276598-tm0yj2sn 859 10 the the DT cord-276598-tm0yj2sn 859 11 Ir Ir NNP cord-276598-tm0yj2sn 859 12 - - HYPH cord-276598-tm0yj2sn 859 13 C C NNP cord-276598-tm0yj2sn 859 14 bond bond NN cord-276598-tm0yj2sn 859 15 , , , cord-276598-tm0yj2sn 859 16 with with IN cord-276598-tm0yj2sn 859 17 removal removal NN cord-276598-tm0yj2sn 859 18 of of IN cord-276598-tm0yj2sn 859 19 N n CD cord-276598-tm0yj2sn 859 20 2 2 CD cord-276598-tm0yj2sn 859 21 , , , cord-276598-tm0yj2sn 859 22 or or CC cord-276598-tm0yj2sn 859 23 by by IN cord-276598-tm0yj2sn 859 24 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 859 25 attack attack NN cord-276598-tm0yj2sn 859 26 from from IN cord-276598-tm0yj2sn 859 27 the the DT cord-276598-tm0yj2sn 859 28 azide azide NN cord-276598-tm0yj2sn 859 29 group group NN cord-276598-tm0yj2sn 859 30 on on IN cord-276598-tm0yj2sn 859 31 the the DT cord-276598-tm0yj2sn 859 32 Ir Ir NNP cord-276598-tm0yj2sn 859 33 - - HYPH cord-276598-tm0yj2sn 859 34 C C NNP cord-276598-tm0yj2sn 859 35 bond bond NN cord-276598-tm0yj2sn 859 36 to to TO cord-276598-tm0yj2sn 859 37 form form VB cord-276598-tm0yj2sn 859 38 the the DT cord-276598-tm0yj2sn 859 39 C C NNP cord-276598-tm0yj2sn 859 40 - - HYPH cord-276598-tm0yj2sn 859 41 N N NNP cord-276598-tm0yj2sn 859 42 bond bond NN cord-276598-tm0yj2sn 859 43 with with IN cord-276598-tm0yj2sn 859 44 the the DT cord-276598-tm0yj2sn 859 45 elimination elimination NN cord-276598-tm0yj2sn 859 46 of of IN cord-276598-tm0yj2sn 859 47 N n CD cord-276598-tm0yj2sn 859 48 2 2 CD cord-276598-tm0yj2sn 859 49 , , , cord-276598-tm0yj2sn 859 50 a a DT cord-276598-tm0yj2sn 859 51 complex complex NN cord-276598-tm0yj2sn 859 52 of of IN cord-276598-tm0yj2sn 859 53 Ir Ir NNP cord-276598-tm0yj2sn 859 54 - - HYPH cord-276598-tm0yj2sn 859 55 N N NNP cord-276598-tm0yj2sn 859 56 - - HYPH cord-276598-tm0yj2sn 859 57 C C NNP cord-276598-tm0yj2sn 859 58 bond bond NN cord-276598-tm0yj2sn 859 59 is be VBZ cord-276598-tm0yj2sn 859 60 formed form VBN cord-276598-tm0yj2sn 859 61 . . . cord-276598-tm0yj2sn 860 1 Proto proto NN cord-276598-tm0yj2sn 860 2 - - HYPH cord-276598-tm0yj2sn 860 3 demetallation demetallation NN cord-276598-tm0yj2sn 860 4 of of IN cord-276598-tm0yj2sn 860 5 the the DT cord-276598-tm0yj2sn 860 6 Ir Ir NNP cord-276598-tm0yj2sn 860 7 ( ( -LRB- cord-276598-tm0yj2sn 860 8 III III NNP cord-276598-tm0yj2sn 860 9 ) ) -RRB- cord-276598-tm0yj2sn 861 1 -based -based JJ cord-276598-tm0yj2sn 861 2 catalyst catalyst NN cord-276598-tm0yj2sn 861 3 affords afford VBZ cord-276598-tm0yj2sn 861 4 the the DT cord-276598-tm0yj2sn 861 5 desired desire VBN cord-276598-tm0yj2sn 861 6 product product NN cord-276598-tm0yj2sn 861 7 while while IN cord-276598-tm0yj2sn 861 8 regenerating regenerate VBG cord-276598-tm0yj2sn 861 9 the the DT cord-276598-tm0yj2sn 861 10 catalyst catalyst NN cord-276598-tm0yj2sn 861 11 . . . cord-276598-tm0yj2sn 862 1 According accord VBG cord-276598-tm0yj2sn 862 2 to to IN cord-276598-tm0yj2sn 862 3 Zhu Zhu NNP cord-276598-tm0yj2sn 862 4 et et FW cord-276598-tm0yj2sn 862 5 al al NNP cord-276598-tm0yj2sn 862 6 . . NNP cord-276598-tm0yj2sn 862 7 , , , cord-276598-tm0yj2sn 862 8 the the DT cord-276598-tm0yj2sn 862 9 mechanistic mechanistic JJ cord-276598-tm0yj2sn 862 10 steps step NNS cord-276598-tm0yj2sn 862 11 involve involve VBP cord-276598-tm0yj2sn 862 12 activation activation NN cord-276598-tm0yj2sn 862 13 of of IN cord-276598-tm0yj2sn 862 14 the the DT cord-276598-tm0yj2sn 862 15 Ir Ir NNP cord-276598-tm0yj2sn 862 16 ( ( -LRB- cord-276598-tm0yj2sn 862 17 III III NNP cord-276598-tm0yj2sn 862 18 ) ) -RRB- cord-276598-tm0yj2sn 862 19 -based -based JJ cord-276598-tm0yj2sn 862 20 catalyst catalyst NN cord-276598-tm0yj2sn 862 21 in in IN cord-276598-tm0yj2sn 862 22 the the DT cord-276598-tm0yj2sn 862 23 presence presence NN cord-276598-tm0yj2sn 862 24 of of IN cord-276598-tm0yj2sn 862 25 AgOAc AgOAc NNS cord-276598-tm0yj2sn 862 26 and and CC cord-276598-tm0yj2sn 862 27 AgSbF AgSbF NNP cord-276598-tm0yj2sn 862 28 6 6 CD cord-276598-tm0yj2sn 862 29 , , , cord-276598-tm0yj2sn 862 30 which which WDT cord-276598-tm0yj2sn 862 31 abstracts abstract VBZ cord-276598-tm0yj2sn 862 32 an an DT cord-276598-tm0yj2sn 862 33 H h NN cord-276598-tm0yj2sn 862 34 atom atom NN cord-276598-tm0yj2sn 862 35 from from IN cord-276598-tm0yj2sn 862 36 the the DT cord-276598-tm0yj2sn 862 37 2-phenylpyridine 2-phenylpyridine CD cord-276598-tm0yj2sn 862 38 derivative derivative JJ cord-276598-tm0yj2sn 862 39 to to IN cord-276598-tm0yj2sn 862 40 cyclo-(2-phenylpyridine)iridium(III cyclo-(2-phenylpyridine)iridium(iii PRP cord-276598-tm0yj2sn 862 41 ) ) -RRB- cord-276598-tm0yj2sn 862 42 complex complex JJ cord-276598-tm0yj2sn 862 43 [ [ -LRB- cord-276598-tm0yj2sn 862 44 114 114 CD cord-276598-tm0yj2sn 862 45 ] ] -RRB- cord-276598-tm0yj2sn 862 46 . . . cord-276598-tm0yj2sn 863 1 The the DT cord-276598-tm0yj2sn 863 2 complex complex JJ cord-276598-tm0yj2sn 863 3 further further RB cord-276598-tm0yj2sn 863 4 coordinates coordinate VBZ cord-276598-tm0yj2sn 863 5 with with IN cord-276598-tm0yj2sn 863 6 phosphoryl phosphoryl NNS cord-276598-tm0yj2sn 863 7 azide azide NN cord-276598-tm0yj2sn 863 8 to to TO cord-276598-tm0yj2sn 863 9 form form VB cord-276598-tm0yj2sn 863 10 a a DT cord-276598-tm0yj2sn 863 11 cyclo-(2-phenylpyridine)iridium(III)-phosphoryl cyclo-(2-phenylpyridine)iridium(iii)-phosphoryl NN cord-276598-tm0yj2sn 863 12 azide azide NN cord-276598-tm0yj2sn 863 13 complex complex NN cord-276598-tm0yj2sn 863 14 , , , cord-276598-tm0yj2sn 863 15 which which WDT cord-276598-tm0yj2sn 863 16 undergoes undergo VBZ cord-276598-tm0yj2sn 863 17 migratory migratory JJ cord-276598-tm0yj2sn 863 18 insertion insertion NN cord-276598-tm0yj2sn 863 19 to to TO cord-276598-tm0yj2sn 863 20 give give VB cord-276598-tm0yj2sn 863 21 a a DT cord-276598-tm0yj2sn 863 22 complex complex NN cord-276598-tm0yj2sn 863 23 containing contain VBG cord-276598-tm0yj2sn 863 24 a a DT cord-276598-tm0yj2sn 863 25 C C NNP cord-276598-tm0yj2sn 863 26 - - HYPH cord-276598-tm0yj2sn 863 27 N N NNP cord-276598-tm0yj2sn 863 28 - - HYPH cord-276598-tm0yj2sn 863 29 Ir Ir NNP cord-276598-tm0yj2sn 863 30 ( ( -LRB- cord-276598-tm0yj2sn 863 31 III III NNP cord-276598-tm0yj2sn 863 32 ) ) -RRB- cord-276598-tm0yj2sn 863 33 bond bond NN cord-276598-tm0yj2sn 863 34 , , , cord-276598-tm0yj2sn 863 35 releasing release VBG cord-276598-tm0yj2sn 863 36 N n CD cord-276598-tm0yj2sn 863 37 2 2 CD cord-276598-tm0yj2sn 863 38 . . . cord-276598-tm0yj2sn 864 1 The the DT cord-276598-tm0yj2sn 864 2 Ir Ir NNP cord-276598-tm0yj2sn 864 3 ( ( -LRB- cord-276598-tm0yj2sn 864 4 III III NNP cord-276598-tm0yj2sn 864 5 ) ) -RRB- cord-276598-tm0yj2sn 865 1 -based -based JJ cord-276598-tm0yj2sn 865 2 catalyst catalyst NN cord-276598-tm0yj2sn 865 3 is be VBZ cord-276598-tm0yj2sn 865 4 released release VBN cord-276598-tm0yj2sn 865 5 through through IN cord-276598-tm0yj2sn 865 6 proto proto NN cord-276598-tm0yj2sn 865 7 - - HYPH cord-276598-tm0yj2sn 865 8 demetallation demetallation NN cord-276598-tm0yj2sn 865 9 to to TO cord-276598-tm0yj2sn 865 10 generate generate VB cord-276598-tm0yj2sn 865 11 the the DT cord-276598-tm0yj2sn 865 12 desired desire VBN cord-276598-tm0yj2sn 865 13 product product NN cord-276598-tm0yj2sn 865 14 . . . cord-276598-tm0yj2sn 866 1 For for IN cord-276598-tm0yj2sn 866 2 the the DT cord-276598-tm0yj2sn 866 3 nitrene nitrene JJ cord-276598-tm0yj2sn 866 4 insertion insertion NN cord-276598-tm0yj2sn 866 5 using use VBG cord-276598-tm0yj2sn 866 6 Ru Ru NNP cord-276598-tm0yj2sn 866 7 IV IV NNP cord-276598-tm0yj2sn 866 8 -porphyrin -porphyrin : cord-276598-tm0yj2sn 866 9 - - HYPH cord-276598-tm0yj2sn 866 10 based base VBN cord-276598-tm0yj2sn 866 11 catalyst catalyst NN cord-276598-tm0yj2sn 866 12 , , , cord-276598-tm0yj2sn 866 13 Che Che NNP cord-276598-tm0yj2sn 866 14 and and CC cord-276598-tm0yj2sn 866 15 coworkers coworker NNS cord-276598-tm0yj2sn 866 16 proposed propose VBD cord-276598-tm0yj2sn 866 17 that that IN cord-276598-tm0yj2sn 866 18 a a DT cord-276598-tm0yj2sn 866 19 reactive reactive JJ cord-276598-tm0yj2sn 866 20 intermediate intermediate JJ cord-276598-tm0yj2sn 866 21 Ru Ru NNP cord-276598-tm0yj2sn 866 22 IV IV NNP cord-276598-tm0yj2sn 866 23 -porphyrin -porphyrin NN cord-276598-tm0yj2sn 866 24 - - HYPH cord-276598-tm0yj2sn 866 25 phosphorylimide phosphorylimide NN cord-276598-tm0yj2sn 866 26 species species NN cord-276598-tm0yj2sn 866 27 is be VBZ cord-276598-tm0yj2sn 866 28 first first RB cord-276598-tm0yj2sn 866 29 formed form VBN cord-276598-tm0yj2sn 866 30 from from IN cord-276598-tm0yj2sn 866 31 the the DT cord-276598-tm0yj2sn 866 32 interaction interaction NN cord-276598-tm0yj2sn 866 33 of of IN cord-276598-tm0yj2sn 866 34 phosphoryl phosphoryl NNS cord-276598-tm0yj2sn 866 35 azide azide NN cord-276598-tm0yj2sn 866 36 and and CC cord-276598-tm0yj2sn 866 37 the the DT cord-276598-tm0yj2sn 866 38 Ru Ru NNP cord-276598-tm0yj2sn 866 39 IV IV NNP cord-276598-tm0yj2sn 866 40 -porphyrin -porphyrin HYPH cord-276598-tm0yj2sn 866 41 catalyst catalyst NN cord-276598-tm0yj2sn 866 42 [ [ -LRB- cord-276598-tm0yj2sn 866 43 113 113 CD cord-276598-tm0yj2sn 866 44 ] ] -RRB- cord-276598-tm0yj2sn 866 45 . . . cord-276598-tm0yj2sn 867 1 Then then RB cord-276598-tm0yj2sn 867 2 , , , cord-276598-tm0yj2sn 867 3 the the DT cord-276598-tm0yj2sn 867 4 intermediate intermediate NN cord-276598-tm0yj2sn 867 5 reacts react VBZ cord-276598-tm0yj2sn 867 6 with with IN cord-276598-tm0yj2sn 867 7 the the DT cord-276598-tm0yj2sn 867 8 aldehyde aldehyde NN cord-276598-tm0yj2sn 867 9 C C NNP cord-276598-tm0yj2sn 867 10 - - HYPH cord-276598-tm0yj2sn 867 11 H H NNP cord-276598-tm0yj2sn 867 12 bond bond NN cord-276598-tm0yj2sn 867 13 through through IN cord-276598-tm0yj2sn 867 14 nitrene nitrene JJ cord-276598-tm0yj2sn 867 15 insertion insertion NN cord-276598-tm0yj2sn 867 16 to to TO cord-276598-tm0yj2sn 867 17 form form VB cord-276598-tm0yj2sn 867 18 a a DT cord-276598-tm0yj2sn 867 19 C C NNP cord-276598-tm0yj2sn 867 20 - - HYPH cord-276598-tm0yj2sn 867 21 N n NN cord-276598-tm0yj2sn 867 22 bonded bond VBN cord-276598-tm0yj2sn 867 23 Ru Ru NNP cord-276598-tm0yj2sn 867 24 IV IV NNP cord-276598-tm0yj2sn 867 25 -porphyrin -porphyrin : cord-276598-tm0yj2sn 867 26 - - HYPH cord-276598-tm0yj2sn 867 27 phosphorylimide phosphorylimide NN cord-276598-tm0yj2sn 867 28 - - HYPH cord-276598-tm0yj2sn 867 29 aldehyde aldehyde NN cord-276598-tm0yj2sn 867 30 complex complex NN cord-276598-tm0yj2sn 867 31 with with IN cord-276598-tm0yj2sn 867 32 the the DT cord-276598-tm0yj2sn 867 33 removal removal NN cord-276598-tm0yj2sn 867 34 of of IN cord-276598-tm0yj2sn 867 35 N n CD cord-276598-tm0yj2sn 867 36 2 2 CD cord-276598-tm0yj2sn 867 37 . . . cord-276598-tm0yj2sn 868 1 The the DT cord-276598-tm0yj2sn 868 2 desired desire VBN cord-276598-tm0yj2sn 868 3 N n NN cord-276598-tm0yj2sn 868 4 - - HYPH cord-276598-tm0yj2sn 868 5 acylphosphoramidates acylphosphoramidates NNP cord-276598-tm0yj2sn 868 6 ( ( -LRB- cord-276598-tm0yj2sn 868 7 AcP AcP NNP cord-276598-tm0yj2sn 868 8 - - HYPH cord-276598-tm0yj2sn 868 9 N N NNP cord-276598-tm0yj2sn 868 10 ) ) -RRB- cord-276598-tm0yj2sn 868 11 product product NN cord-276598-tm0yj2sn 868 12 is be VBZ cord-276598-tm0yj2sn 868 13 formed form VBN cord-276598-tm0yj2sn 868 14 after after IN cord-276598-tm0yj2sn 868 15 proto proto NN cord-276598-tm0yj2sn 868 16 - - HYPH cord-276598-tm0yj2sn 868 17 demetallation demetallation NN cord-276598-tm0yj2sn 868 18 of of IN cord-276598-tm0yj2sn 868 19 the the DT cord-276598-tm0yj2sn 868 20 Ru Ru NNP cord-276598-tm0yj2sn 868 21 IV IV NNP cord-276598-tm0yj2sn 868 22 -porphyrin -porphyrin HYPH cord-276598-tm0yj2sn 868 23 catalyst catalyst NN cord-276598-tm0yj2sn 868 24 , , , cord-276598-tm0yj2sn 868 25 and and CC cord-276598-tm0yj2sn 868 26 the the DT cord-276598-tm0yj2sn 868 27 catalyst catalyst NN cord-276598-tm0yj2sn 868 28 is be VBZ cord-276598-tm0yj2sn 868 29 regenerated regenerate VBN cord-276598-tm0yj2sn 868 30 in in IN cord-276598-tm0yj2sn 868 31 the the DT cord-276598-tm0yj2sn 868 32 process process NN cord-276598-tm0yj2sn 868 33 . . . cord-276598-tm0yj2sn 869 1 Molecules molecule NNS cord-276598-tm0yj2sn 869 2 2020 2020 CD cord-276598-tm0yj2sn 869 3 , , , cord-276598-tm0yj2sn 869 4 25 25 CD cord-276598-tm0yj2sn 870 1 For for IN cord-276598-tm0yj2sn 870 2 the the DT cord-276598-tm0yj2sn 870 3 nitrene nitrene JJ cord-276598-tm0yj2sn 870 4 insertion insertion NN cord-276598-tm0yj2sn 870 5 using use VBG cord-276598-tm0yj2sn 870 6 Ru Ru NNP cord-276598-tm0yj2sn 870 7 IV IV NNP cord-276598-tm0yj2sn 870 8 -porphyrin -porphyrin : cord-276598-tm0yj2sn 870 9 - - HYPH cord-276598-tm0yj2sn 870 10 based base VBN cord-276598-tm0yj2sn 870 11 catalyst catalyst NN cord-276598-tm0yj2sn 870 12 , , , cord-276598-tm0yj2sn 870 13 Che Che NNP cord-276598-tm0yj2sn 870 14 and and CC cord-276598-tm0yj2sn 870 15 coworkers coworker NNS cord-276598-tm0yj2sn 870 16 proposed propose VBD cord-276598-tm0yj2sn 870 17 that that IN cord-276598-tm0yj2sn 870 18 a a DT cord-276598-tm0yj2sn 870 19 reactive reactive JJ cord-276598-tm0yj2sn 870 20 intermediate intermediate JJ cord-276598-tm0yj2sn 870 21 Ru Ru NNP cord-276598-tm0yj2sn 870 22 IV IV NNP cord-276598-tm0yj2sn 870 23 -porphyrin -porphyrin NN cord-276598-tm0yj2sn 870 24 - - HYPH cord-276598-tm0yj2sn 870 25 phosphorylimide phosphorylimide NN cord-276598-tm0yj2sn 870 26 species species NN cord-276598-tm0yj2sn 870 27 is be VBZ cord-276598-tm0yj2sn 870 28 first first RB cord-276598-tm0yj2sn 870 29 formed form VBN cord-276598-tm0yj2sn 870 30 from from IN cord-276598-tm0yj2sn 870 31 the the DT cord-276598-tm0yj2sn 870 32 interaction interaction NN cord-276598-tm0yj2sn 870 33 of of IN cord-276598-tm0yj2sn 870 34 phosphoryl phosphoryl NNS cord-276598-tm0yj2sn 870 35 azide azide NN cord-276598-tm0yj2sn 870 36 and and CC cord-276598-tm0yj2sn 870 37 the the DT cord-276598-tm0yj2sn 870 38 Ru Ru NNP cord-276598-tm0yj2sn 870 39 IV IV NNP cord-276598-tm0yj2sn 870 40 -porphyrin -porphyrin HYPH cord-276598-tm0yj2sn 870 41 catalyst catalyst NN cord-276598-tm0yj2sn 870 42 [ [ -LRB- cord-276598-tm0yj2sn 870 43 113 113 CD cord-276598-tm0yj2sn 870 44 ] ] -RRB- cord-276598-tm0yj2sn 870 45 . . . cord-276598-tm0yj2sn 871 1 Then then RB cord-276598-tm0yj2sn 871 2 , , , cord-276598-tm0yj2sn 871 3 the the DT cord-276598-tm0yj2sn 871 4 intermediate intermediate NN cord-276598-tm0yj2sn 871 5 reacts react VBZ cord-276598-tm0yj2sn 871 6 with with IN cord-276598-tm0yj2sn 871 7 the the DT cord-276598-tm0yj2sn 871 8 aldehyde aldehyde NN cord-276598-tm0yj2sn 871 9 C C NNP cord-276598-tm0yj2sn 871 10 - - HYPH cord-276598-tm0yj2sn 871 11 H H NNP cord-276598-tm0yj2sn 871 12 bond bond NN cord-276598-tm0yj2sn 871 13 through through IN cord-276598-tm0yj2sn 871 14 nitrene nitrene JJ cord-276598-tm0yj2sn 871 15 insertion insertion NN cord-276598-tm0yj2sn 871 16 to to TO cord-276598-tm0yj2sn 871 17 form form VB cord-276598-tm0yj2sn 871 18 a a DT cord-276598-tm0yj2sn 871 19 C C NNP cord-276598-tm0yj2sn 871 20 - - HYPH cord-276598-tm0yj2sn 871 21 N n NN cord-276598-tm0yj2sn 871 22 bonded bond VBN cord-276598-tm0yj2sn 871 23 Ru Ru NNP cord-276598-tm0yj2sn 871 24 IV IV NNP cord-276598-tm0yj2sn 871 25 -porphyrin -porphyrin : cord-276598-tm0yj2sn 871 26 - - HYPH cord-276598-tm0yj2sn 871 27 phosphorylimide phosphorylimide NN cord-276598-tm0yj2sn 871 28 - - HYPH cord-276598-tm0yj2sn 871 29 aldehyde aldehyde NN cord-276598-tm0yj2sn 871 30 complex complex NN cord-276598-tm0yj2sn 871 31 with with IN cord-276598-tm0yj2sn 871 32 the the DT cord-276598-tm0yj2sn 871 33 removal removal NN cord-276598-tm0yj2sn 871 34 of of IN cord-276598-tm0yj2sn 871 35 N2 N2 NNP cord-276598-tm0yj2sn 871 36 . . . cord-276598-tm0yj2sn 872 1 The the DT cord-276598-tm0yj2sn 872 2 desired desire VBN cord-276598-tm0yj2sn 872 3 Scheme Scheme NNP cord-276598-tm0yj2sn 872 4 33 33 CD cord-276598-tm0yj2sn 872 5 . . . cord-276598-tm0yj2sn 873 1 Proposed propose VBN cord-276598-tm0yj2sn 873 2 mechanism mechanism NN cord-276598-tm0yj2sn 873 3 for for IN cord-276598-tm0yj2sn 873 4 the the DT cord-276598-tm0yj2sn 873 5 Ir Ir NNP cord-276598-tm0yj2sn 873 6 - - HYPH cord-276598-tm0yj2sn 873 7 catalyzed catalyze VBN cord-276598-tm0yj2sn 873 8 synthesis synthesis NN cord-276598-tm0yj2sn 873 9 of of IN cord-276598-tm0yj2sn 873 10 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 873 11 . . . cord-276598-tm0yj2sn 874 1 In in IN cord-276598-tm0yj2sn 874 2 the the DT cord-276598-tm0yj2sn 874 3 reported report VBN cord-276598-tm0yj2sn 874 4 mechanisms mechanism NNS cord-276598-tm0yj2sn 874 5 of of IN cord-276598-tm0yj2sn 874 6 the the DT cord-276598-tm0yj2sn 874 7 reaction reaction NN cord-276598-tm0yj2sn 874 8 for for IN cord-276598-tm0yj2sn 874 9 P p NN cord-276598-tm0yj2sn 874 10 - - HYPH cord-276598-tm0yj2sn 874 11 N n CD cord-276598-tm0yj2sn 874 12 synthesis synthesis NN cord-276598-tm0yj2sn 874 13 via via IN cord-276598-tm0yj2sn 874 14 azide azide NN cord-276598-tm0yj2sn 874 15 generation generation NN cord-276598-tm0yj2sn 874 16 , , , cord-276598-tm0yj2sn 874 17 organic organic JJ cord-276598-tm0yj2sn 874 18 azide azide NN cord-276598-tm0yj2sn 874 19 is be VBZ cord-276598-tm0yj2sn 874 20 formed form VBN cord-276598-tm0yj2sn 874 21 in in IN cord-276598-tm0yj2sn 874 22 the the DT cord-276598-tm0yj2sn 874 23 first first JJ cord-276598-tm0yj2sn 874 24 step step NN cord-276598-tm0yj2sn 874 25 from from IN cord-276598-tm0yj2sn 874 26 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 874 27 substitution substitution NN cord-276598-tm0yj2sn 874 28 of of IN cord-276598-tm0yj2sn 874 29 the the DT cord-276598-tm0yj2sn 874 30 organic organic JJ cord-276598-tm0yj2sn 874 31 halide halide NN cord-276598-tm0yj2sn 874 32 with with IN cord-276598-tm0yj2sn 874 33 the the DT cord-276598-tm0yj2sn 874 34 elimination elimination NN cord-276598-tm0yj2sn 874 35 of of IN cord-276598-tm0yj2sn 874 36 N n CD cord-276598-tm0yj2sn 874 37 2 2 CD cord-276598-tm0yj2sn 874 38 gas gas NN cord-276598-tm0yj2sn 874 39 . . . cord-276598-tm0yj2sn 875 1 In in IN cord-276598-tm0yj2sn 875 2 the the DT cord-276598-tm0yj2sn 875 3 second second JJ cord-276598-tm0yj2sn 875 4 step step NN cord-276598-tm0yj2sn 875 5 , , , cord-276598-tm0yj2sn 875 6 the the DT cord-276598-tm0yj2sn 875 7 organic organic JJ cord-276598-tm0yj2sn 875 8 azide azide NN cord-276598-tm0yj2sn 875 9 reacts react VBZ cord-276598-tm0yj2sn 875 10 with with IN cord-276598-tm0yj2sn 875 11 ( ( -LRB- cord-276598-tm0yj2sn 875 12 RO ro NN cord-276598-tm0yj2sn 875 13 ) ) -RRB- cord-276598-tm0yj2sn 875 14 3 3 CD cord-276598-tm0yj2sn 875 15 P p NN cord-276598-tm0yj2sn 875 16 ( ( -LRB- cord-276598-tm0yj2sn 875 17 R r NN cord-276598-tm0yj2sn 875 18 = = NN cord-276598-tm0yj2sn 875 19 alkyl alkyl NN cord-276598-tm0yj2sn 875 20 ) ) -RRB- cord-276598-tm0yj2sn 875 21 to to TO cord-276598-tm0yj2sn 875 22 form form VB cord-276598-tm0yj2sn 875 23 the the DT cord-276598-tm0yj2sn 875 24 P P NNP cord-276598-tm0yj2sn 875 25 - - HYPH cord-276598-tm0yj2sn 875 26 N N NNP cord-276598-tm0yj2sn 875 27 compound compound NN cord-276598-tm0yj2sn 875 28 after after IN cord-276598-tm0yj2sn 875 29 rearrangement rearrangement NN cord-276598-tm0yj2sn 875 30 or or CC cord-276598-tm0yj2sn 875 31 hydrolysis hydrolysis NN cord-276598-tm0yj2sn 875 32 ( ( -LRB- cord-276598-tm0yj2sn 875 33 Scheme scheme NN cord-276598-tm0yj2sn 875 34 34 34 CD cord-276598-tm0yj2sn 875 35 ) ) -RRB- cord-276598-tm0yj2sn 875 36 [ [ -LRB- cord-276598-tm0yj2sn 875 37 93 93 CD cord-276598-tm0yj2sn 875 38 , , , cord-276598-tm0yj2sn 875 39 115 115 CD cord-276598-tm0yj2sn 875 40 , , , cord-276598-tm0yj2sn 875 41 116 116 CD cord-276598-tm0yj2sn 875 42 ] ] -RRB- cord-276598-tm0yj2sn 875 43 . . . cord-276598-tm0yj2sn 876 1 interaction interaction NN cord-276598-tm0yj2sn 876 2 of of IN cord-276598-tm0yj2sn 876 3 phosphoryl phosphoryl NNP cord-276598-tm0yj2sn 876 4 azide azide NN cord-276598-tm0yj2sn 876 5 and and CC cord-276598-tm0yj2sn 876 6 the the DT cord-276598-tm0yj2sn 876 7 Ru Ru NNP cord-276598-tm0yj2sn 876 8 IV IV NNP cord-276598-tm0yj2sn 876 9 -porphyrin -porphyrin HYPH cord-276598-tm0yj2sn 876 10 catalyst catalyst NN cord-276598-tm0yj2sn 876 11 [ [ -LRB- cord-276598-tm0yj2sn 876 12 113 113 CD cord-276598-tm0yj2sn 876 13 ] ] -RRB- cord-276598-tm0yj2sn 876 14 . . . cord-276598-tm0yj2sn 877 1 Then then RB cord-276598-tm0yj2sn 877 2 , , , cord-276598-tm0yj2sn 877 3 the the DT cord-276598-tm0yj2sn 877 4 intermediate intermediate NN cord-276598-tm0yj2sn 877 5 reacts react VBZ cord-276598-tm0yj2sn 877 6 with with IN cord-276598-tm0yj2sn 877 7 the the DT cord-276598-tm0yj2sn 877 8 aldehyde aldehyde NN cord-276598-tm0yj2sn 877 9 C C NNP cord-276598-tm0yj2sn 877 10 - - HYPH cord-276598-tm0yj2sn 877 11 H H NNP cord-276598-tm0yj2sn 877 12 bond bond NN cord-276598-tm0yj2sn 877 13 through through IN cord-276598-tm0yj2sn 877 14 nitrene nitrene JJ cord-276598-tm0yj2sn 877 15 insertion insertion NN cord-276598-tm0yj2sn 877 16 to to TO cord-276598-tm0yj2sn 877 17 form form VB cord-276598-tm0yj2sn 877 18 a a DT cord-276598-tm0yj2sn 877 19 C C NNP cord-276598-tm0yj2sn 877 20 - - HYPH cord-276598-tm0yj2sn 877 21 N n NN cord-276598-tm0yj2sn 877 22 bonded bond VBN cord-276598-tm0yj2sn 877 23 Ru Ru NNP cord-276598-tm0yj2sn 877 24 IV IV NNP cord-276598-tm0yj2sn 877 25 -porphyrin -porphyrin : cord-276598-tm0yj2sn 877 26 - - HYPH cord-276598-tm0yj2sn 877 27 phosphorylimide phosphorylimide NN cord-276598-tm0yj2sn 877 28 - - HYPH cord-276598-tm0yj2sn 877 29 aldehyde aldehyde NN cord-276598-tm0yj2sn 877 30 complex complex NN cord-276598-tm0yj2sn 877 31 with with IN cord-276598-tm0yj2sn 877 32 the the DT cord-276598-tm0yj2sn 877 33 removal removal NN cord-276598-tm0yj2sn 877 34 of of IN cord-276598-tm0yj2sn 877 35 N2 N2 NNP cord-276598-tm0yj2sn 877 36 . . . cord-276598-tm0yj2sn 878 1 The the DT cord-276598-tm0yj2sn 878 2 desired desire VBN cord-276598-tm0yj2sn 878 3 N n NN cord-276598-tm0yj2sn 878 4 - - HYPH cord-276598-tm0yj2sn 878 5 acylphosphoramidates acylphosphoramidates NNP cord-276598-tm0yj2sn 878 6 ( ( -LRB- cord-276598-tm0yj2sn 878 7 AcP AcP NNP cord-276598-tm0yj2sn 878 8 - - HYPH cord-276598-tm0yj2sn 878 9 N N NNP cord-276598-tm0yj2sn 878 10 ) ) -RRB- cord-276598-tm0yj2sn 878 11 product product NN cord-276598-tm0yj2sn 878 12 is be VBZ cord-276598-tm0yj2sn 878 13 formed form VBN cord-276598-tm0yj2sn 878 14 after after IN cord-276598-tm0yj2sn 878 15 proto proto NN cord-276598-tm0yj2sn 878 16 - - HYPH cord-276598-tm0yj2sn 878 17 demetallation demetallation NN cord-276598-tm0yj2sn 878 18 of of IN cord-276598-tm0yj2sn 878 19 the the DT cord-276598-tm0yj2sn 878 20 Ru Ru NNP cord-276598-tm0yj2sn 878 21 IV IV NNP cord-276598-tm0yj2sn 878 22 -porphyrin -porphyrin HYPH cord-276598-tm0yj2sn 878 23 catalyst catalyst NN cord-276598-tm0yj2sn 878 24 , , , cord-276598-tm0yj2sn 878 25 and and CC cord-276598-tm0yj2sn 878 26 the the DT cord-276598-tm0yj2sn 878 27 catalyst catalyst NN cord-276598-tm0yj2sn 878 28 is be VBZ cord-276598-tm0yj2sn 878 29 regenerated regenerate VBN cord-276598-tm0yj2sn 878 30 in in IN cord-276598-tm0yj2sn 878 31 the the DT cord-276598-tm0yj2sn 878 32 process process NN cord-276598-tm0yj2sn 878 33 . . . cord-276598-tm0yj2sn 879 1 In in IN cord-276598-tm0yj2sn 879 2 the the DT cord-276598-tm0yj2sn 879 3 reported report VBN cord-276598-tm0yj2sn 879 4 mechanisms mechanism NNS cord-276598-tm0yj2sn 879 5 of of IN cord-276598-tm0yj2sn 879 6 the the DT cord-276598-tm0yj2sn 879 7 reaction reaction NN cord-276598-tm0yj2sn 879 8 for for IN cord-276598-tm0yj2sn 879 9 P p NN cord-276598-tm0yj2sn 879 10 - - HYPH cord-276598-tm0yj2sn 879 11 N n CD cord-276598-tm0yj2sn 879 12 synthesis synthesis NN cord-276598-tm0yj2sn 879 13 via via IN cord-276598-tm0yj2sn 879 14 azide azide NN cord-276598-tm0yj2sn 879 15 generation generation NN cord-276598-tm0yj2sn 879 16 , , , cord-276598-tm0yj2sn 879 17 organic organic JJ cord-276598-tm0yj2sn 879 18 azide azide NN cord-276598-tm0yj2sn 879 19 is be VBZ cord-276598-tm0yj2sn 879 20 formed form VBN cord-276598-tm0yj2sn 879 21 in in IN cord-276598-tm0yj2sn 879 22 the the DT cord-276598-tm0yj2sn 879 23 first first JJ cord-276598-tm0yj2sn 879 24 step step NN cord-276598-tm0yj2sn 879 25 from from IN cord-276598-tm0yj2sn 879 26 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 879 27 substitution substitution NN cord-276598-tm0yj2sn 879 28 of of IN cord-276598-tm0yj2sn 879 29 the the DT cord-276598-tm0yj2sn 879 30 organic organic JJ cord-276598-tm0yj2sn 879 31 halide halide NN cord-276598-tm0yj2sn 879 32 with with IN cord-276598-tm0yj2sn 879 33 the the DT cord-276598-tm0yj2sn 879 34 elimination elimination NN cord-276598-tm0yj2sn 879 35 of of IN cord-276598-tm0yj2sn 879 36 N2 N2 NNP cord-276598-tm0yj2sn 879 37 gas gas NN cord-276598-tm0yj2sn 879 38 . . . cord-276598-tm0yj2sn 880 1 In in IN cord-276598-tm0yj2sn 880 2 the the DT cord-276598-tm0yj2sn 880 3 second second JJ cord-276598-tm0yj2sn 880 4 step step NN cord-276598-tm0yj2sn 880 5 , , , cord-276598-tm0yj2sn 880 6 the the DT cord-276598-tm0yj2sn 880 7 organic organic JJ cord-276598-tm0yj2sn 880 8 azide azide NN cord-276598-tm0yj2sn 880 9 reacts react VBZ cord-276598-tm0yj2sn 880 10 with with IN cord-276598-tm0yj2sn 880 11 ( ( -LRB- cord-276598-tm0yj2sn 880 12 RO)3P RO)3P NNP cord-276598-tm0yj2sn 880 13 ( ( -LRB- cord-276598-tm0yj2sn 880 14 R r NN cord-276598-tm0yj2sn 880 15 = = NN cord-276598-tm0yj2sn 880 16 alkyl alkyl NN cord-276598-tm0yj2sn 880 17 ) ) -RRB- cord-276598-tm0yj2sn 880 18 to to TO cord-276598-tm0yj2sn 880 19 form form VB cord-276598-tm0yj2sn 880 20 the the DT cord-276598-tm0yj2sn 880 21 P P NNP cord-276598-tm0yj2sn 880 22 - - HYPH cord-276598-tm0yj2sn 880 23 N N NNP cord-276598-tm0yj2sn 880 24 compound compound NN cord-276598-tm0yj2sn 880 25 after after IN cord-276598-tm0yj2sn 880 26 rearrangement rearrangement NN cord-276598-tm0yj2sn 880 27 or or CC cord-276598-tm0yj2sn 880 28 hydrolysis hydrolysis NN cord-276598-tm0yj2sn 880 29 ( ( -LRB- cord-276598-tm0yj2sn 880 30 Scheme scheme NN cord-276598-tm0yj2sn 880 31 34 34 CD cord-276598-tm0yj2sn 880 32 ) ) -RRB- cord-276598-tm0yj2sn 880 33 [ [ -LRB- cord-276598-tm0yj2sn 880 34 93 93 CD cord-276598-tm0yj2sn 880 35 , , , cord-276598-tm0yj2sn 880 36 115 115 CD cord-276598-tm0yj2sn 880 37 , , , cord-276598-tm0yj2sn 880 38 116 116 CD cord-276598-tm0yj2sn 880 39 ] ] -RRB- cord-276598-tm0yj2sn 880 40 . . . cord-276598-tm0yj2sn 881 1 Scheme scheme NN cord-276598-tm0yj2sn 881 2 34 34 CD cord-276598-tm0yj2sn 881 3 . . . cord-276598-tm0yj2sn 882 1 Proposed propose VBN cord-276598-tm0yj2sn 882 2 mechanism mechanism NN cord-276598-tm0yj2sn 882 3 to to IN cord-276598-tm0yj2sn 882 4 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 882 5 via via IN cord-276598-tm0yj2sn 882 6 azide azide NN cord-276598-tm0yj2sn 882 7 generation generation NN cord-276598-tm0yj2sn 882 8 . . . cord-276598-tm0yj2sn 883 1 According accord VBG cord-276598-tm0yj2sn 883 2 to to IN cord-276598-tm0yj2sn 883 3 the the DT cord-276598-tm0yj2sn 883 4 mechanism mechanism NN cord-276598-tm0yj2sn 883 5 suggested suggest VBN cord-276598-tm0yj2sn 883 6 by by IN cord-276598-tm0yj2sn 883 7 Chen Chen NNP cord-276598-tm0yj2sn 883 8 et et NNP cord-276598-tm0yj2sn 883 9 al al NNP cord-276598-tm0yj2sn 883 10 . . NNP cord-276598-tm0yj2sn 883 11 , , , cord-276598-tm0yj2sn 883 12 the the DT cord-276598-tm0yj2sn 883 13 amine amine NN cord-276598-tm0yj2sn 883 14 reacts react VBZ cord-276598-tm0yj2sn 883 15 with with IN cord-276598-tm0yj2sn 883 16 phosphoryl phosphoryl NNS cord-276598-tm0yj2sn 883 17 azide azide NN cord-276598-tm0yj2sn 883 18 through through IN cord-276598-tm0yj2sn 883 19 a a DT cord-276598-tm0yj2sn 883 20 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 883 21 substitution substitution NN cord-276598-tm0yj2sn 883 22 reaction reaction NN cord-276598-tm0yj2sn 883 23 to to TO cord-276598-tm0yj2sn 883 24 generate generate VB cord-276598-tm0yj2sn 883 25 an an DT cord-276598-tm0yj2sn 883 26 azido azido NN cord-276598-tm0yj2sn 883 27 ( ( -LRB- cord-276598-tm0yj2sn 883 28 hydroxy)-phosphanamine hydroxy)-phosphanamine JJ cord-276598-tm0yj2sn 883 29 complex complex JJ cord-276598-tm0yj2sn 883 30 intermediate intermediate JJ cord-276598-tm0yj2sn 883 31 in in IN cord-276598-tm0yj2sn 883 32 the the DT cord-276598-tm0yj2sn 883 33 first first JJ cord-276598-tm0yj2sn 883 34 step step NN cord-276598-tm0yj2sn 883 35 [ [ -LRB- cord-276598-tm0yj2sn 883 36 117 117 CD cord-276598-tm0yj2sn 883 37 ] ] -RRB- cord-276598-tm0yj2sn 883 38 . . . cord-276598-tm0yj2sn 884 1 In in IN cord-276598-tm0yj2sn 884 2 the the DT cord-276598-tm0yj2sn 884 3 second second JJ cord-276598-tm0yj2sn 884 4 step step NN cord-276598-tm0yj2sn 884 5 , , , cord-276598-tm0yj2sn 884 6 the the DT cord-276598-tm0yj2sn 884 7 azide azide NN cord-276598-tm0yj2sn 884 8 anion anion NN cord-276598-tm0yj2sn 884 9 departs depart VBZ cord-276598-tm0yj2sn 884 10 as as IN cord-276598-tm0yj2sn 884 11 the the DT cord-276598-tm0yj2sn 884 12 leaving leave VBG cord-276598-tm0yj2sn 884 13 group group NN cord-276598-tm0yj2sn 884 14 to to TO cord-276598-tm0yj2sn 884 15 give give VB cord-276598-tm0yj2sn 884 16 a a DT cord-276598-tm0yj2sn 884 17 stable stable JJ cord-276598-tm0yj2sn 884 18 P p NN cord-276598-tm0yj2sn 884 19 - - HYPH cord-276598-tm0yj2sn 884 20 N n CD cord-276598-tm0yj2sn 884 21 product product NN cord-276598-tm0yj2sn 884 22 ( ( -LRB- cord-276598-tm0yj2sn 884 23 Scheme scheme NN cord-276598-tm0yj2sn 884 24 35 35 CD cord-276598-tm0yj2sn 884 25 ) ) -RRB- cord-276598-tm0yj2sn 884 26 . . . cord-276598-tm0yj2sn 885 1 Although although IN cord-276598-tm0yj2sn 885 2 the the DT cord-276598-tm0yj2sn 885 3 mechanism mechanism NN cord-276598-tm0yj2sn 885 4 looks look VBZ cord-276598-tm0yj2sn 885 5 highly highly RB cord-276598-tm0yj2sn 885 6 plausible plausible JJ cord-276598-tm0yj2sn 885 7 , , , cord-276598-tm0yj2sn 885 8 it -PRON- PRP cord-276598-tm0yj2sn 885 9 is be VBZ cord-276598-tm0yj2sn 885 10 noteworthy noteworthy JJ cord-276598-tm0yj2sn 885 11 that that IN cord-276598-tm0yj2sn 885 12 N3 n3 NN cord-276598-tm0yj2sn 885 13 is be VBZ cord-276598-tm0yj2sn 885 14 highly highly RB cord-276598-tm0yj2sn 885 15 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 885 16 because because IN cord-276598-tm0yj2sn 885 17 in in IN cord-276598-tm0yj2sn 885 18 its -PRON- PRP$ cord-276598-tm0yj2sn 885 19 canonical canonical JJ cord-276598-tm0yj2sn 885 20 structure structure NN cord-276598-tm0yj2sn 885 21 , , , cord-276598-tm0yj2sn 885 22 one one CD cord-276598-tm0yj2sn 885 23 of of IN cord-276598-tm0yj2sn 885 24 the the DT cord-276598-tm0yj2sn 885 25 nitrogen nitrogen NN cord-276598-tm0yj2sn 885 26 atoms atom NNS cord-276598-tm0yj2sn 885 27 carries carry VBZ cord-276598-tm0yj2sn 885 28 a a DT cord-276598-tm0yj2sn 885 29 double double JJ cord-276598-tm0yj2sn 885 30 negative negative JJ cord-276598-tm0yj2sn 885 31 charge charge NN cord-276598-tm0yj2sn 885 32 ( ( -LRB- cord-276598-tm0yj2sn 885 33 N≡N n≡n NN cord-276598-tm0yj2sn 885 34 + + SYM cord-276598-tm0yj2sn 885 35 − − NN cord-276598-tm0yj2sn 885 36 N n CD cord-276598-tm0yj2sn 885 37 2− 2− CD cord-276598-tm0yj2sn 885 38 ) ) -RRB- cord-276598-tm0yj2sn 885 39 [ [ -LRB- cord-276598-tm0yj2sn 885 40 124 124 CD cord-276598-tm0yj2sn 885 41 ] ] -RRB- cord-276598-tm0yj2sn 885 42 , , , cord-276598-tm0yj2sn 885 43 which which WDT cord-276598-tm0yj2sn 885 44 makes make VBZ cord-276598-tm0yj2sn 885 45 it -PRON- PRP cord-276598-tm0yj2sn 885 46 stable stable JJ cord-276598-tm0yj2sn 885 47 and and CC cord-276598-tm0yj2sn 885 48 a a DT cord-276598-tm0yj2sn 885 49 poor poor JJ cord-276598-tm0yj2sn 885 50 leaving leave VBG cord-276598-tm0yj2sn 885 51 group group NN cord-276598-tm0yj2sn 885 52 as as IN cord-276598-tm0yj2sn 885 53 N3 n3 NN cord-276598-tm0yj2sn 885 54 in in IN cord-276598-tm0yj2sn 885 55 the the DT cord-276598-tm0yj2sn 885 56 presence presence NN cord-276598-tm0yj2sn 885 57 of of IN cord-276598-tm0yj2sn 885 58 amine amine NN cord-276598-tm0yj2sn 885 59 [ [ -LRB- cord-276598-tm0yj2sn 885 60 125 125 CD cord-276598-tm0yj2sn 885 61 ] ] -RRB- cord-276598-tm0yj2sn 885 62 . . . cord-276598-tm0yj2sn 886 1 In in IN cord-276598-tm0yj2sn 886 2 addition addition NN cord-276598-tm0yj2sn 886 3 , , , cord-276598-tm0yj2sn 886 4 the the DT cord-276598-tm0yj2sn 886 5 mechanism mechanism NN cord-276598-tm0yj2sn 886 6 does do VBZ cord-276598-tm0yj2sn 886 7 account account VB cord-276598-tm0yj2sn 886 8 for for IN cord-276598-tm0yj2sn 886 9 the the DT cord-276598-tm0yj2sn 886 10 potentially potentially RB cord-276598-tm0yj2sn 886 11 explosive explosive JJ cord-276598-tm0yj2sn 886 12 HN3 hn3 NN cord-276598-tm0yj2sn 886 13 in in IN cord-276598-tm0yj2sn 886 14 a a DT cord-276598-tm0yj2sn 886 15 closed closed JJ cord-276598-tm0yj2sn 886 16 flask flask NN cord-276598-tm0yj2sn 886 17 at at IN cord-276598-tm0yj2sn 886 18 120 120 CD cord-276598-tm0yj2sn 886 19 ° ° NN cord-276598-tm0yj2sn 886 20 C c NN cord-276598-tm0yj2sn 886 21 . . . cord-276598-tm0yj2sn 887 1 However however RB cord-276598-tm0yj2sn 887 2 , , , cord-276598-tm0yj2sn 887 3 it -PRON- PRP cord-276598-tm0yj2sn 887 4 is be VBZ cord-276598-tm0yj2sn 887 5 possible possible JJ cord-276598-tm0yj2sn 887 6 that that IN cord-276598-tm0yj2sn 887 7 in in IN cord-276598-tm0yj2sn 887 8 the the DT cord-276598-tm0yj2sn 887 9 reaction reaction NN cord-276598-tm0yj2sn 887 10 process process NN cord-276598-tm0yj2sn 887 11 , , , cord-276598-tm0yj2sn 887 12 the the DT cord-276598-tm0yj2sn 887 13 azide azide NN cord-276598-tm0yj2sn 887 14 is be VBZ cord-276598-tm0yj2sn 887 15 first first RB cord-276598-tm0yj2sn 887 16 reduced reduce VBN cord-276598-tm0yj2sn 887 17 or or CC cord-276598-tm0yj2sn 887 18 decomposed decompose VBN cord-276598-tm0yj2sn 887 19 to to IN cord-276598-tm0yj2sn 887 20 a a DT cord-276598-tm0yj2sn 887 21 nitrene nitrene JJ cord-276598-tm0yj2sn 887 22 phosphonate phosphonate NNP cord-276598-tm0yj2sn 887 23 radical radical JJ cord-276598-tm0yj2sn 887 24 ( ( -LRB- cord-276598-tm0yj2sn 887 25 ( ( -LRB- cord-276598-tm0yj2sn 887 26 RO)2P(O)N RO)2P(O)N VBG cord-276598-tm0yj2sn 887 27 ; ; : cord-276598-tm0yj2sn 887 28 R r NN cord-276598-tm0yj2sn 887 29 = = SYM cord-276598-tm0yj2sn 887 30 Scheme scheme NN cord-276598-tm0yj2sn 887 31 34 34 CD cord-276598-tm0yj2sn 887 32 . . . cord-276598-tm0yj2sn 888 1 Proposed propose VBN cord-276598-tm0yj2sn 888 2 mechanism mechanism NN cord-276598-tm0yj2sn 888 3 to to IN cord-276598-tm0yj2sn 888 4 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 888 5 via via IN cord-276598-tm0yj2sn 888 6 azide azide NN cord-276598-tm0yj2sn 888 7 generation generation NN cord-276598-tm0yj2sn 888 8 . . . cord-276598-tm0yj2sn 889 1 According accord VBG cord-276598-tm0yj2sn 889 2 to to IN cord-276598-tm0yj2sn 889 3 the the DT cord-276598-tm0yj2sn 889 4 mechanism mechanism NN cord-276598-tm0yj2sn 889 5 suggested suggest VBN cord-276598-tm0yj2sn 889 6 by by IN cord-276598-tm0yj2sn 889 7 Chen Chen NNP cord-276598-tm0yj2sn 889 8 et et NNP cord-276598-tm0yj2sn 889 9 al al NNP cord-276598-tm0yj2sn 889 10 . . NNP cord-276598-tm0yj2sn 889 11 , , , cord-276598-tm0yj2sn 889 12 the the DT cord-276598-tm0yj2sn 889 13 amine amine NN cord-276598-tm0yj2sn 889 14 reacts react VBZ cord-276598-tm0yj2sn 889 15 with with IN cord-276598-tm0yj2sn 889 16 phosphoryl phosphoryl NNS cord-276598-tm0yj2sn 889 17 azide azide NN cord-276598-tm0yj2sn 889 18 through through IN cord-276598-tm0yj2sn 889 19 a a DT cord-276598-tm0yj2sn 889 20 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 889 21 substitution substitution NN cord-276598-tm0yj2sn 889 22 reaction reaction NN cord-276598-tm0yj2sn 889 23 to to TO cord-276598-tm0yj2sn 889 24 generate generate VB cord-276598-tm0yj2sn 889 25 an an DT cord-276598-tm0yj2sn 889 26 azido azido NN cord-276598-tm0yj2sn 889 27 ( ( -LRB- cord-276598-tm0yj2sn 889 28 hydroxy)-phosphanamine hydroxy)-phosphanamine JJ cord-276598-tm0yj2sn 889 29 complex complex JJ cord-276598-tm0yj2sn 889 30 intermediate intermediate JJ cord-276598-tm0yj2sn 889 31 in in IN cord-276598-tm0yj2sn 889 32 the the DT cord-276598-tm0yj2sn 889 33 first first JJ cord-276598-tm0yj2sn 889 34 step step NN cord-276598-tm0yj2sn 889 35 [ [ -LRB- cord-276598-tm0yj2sn 889 36 117 117 CD cord-276598-tm0yj2sn 889 37 ] ] -RRB- cord-276598-tm0yj2sn 889 38 . . . cord-276598-tm0yj2sn 890 1 In in IN cord-276598-tm0yj2sn 890 2 the the DT cord-276598-tm0yj2sn 890 3 second second JJ cord-276598-tm0yj2sn 890 4 step step NN cord-276598-tm0yj2sn 890 5 , , , cord-276598-tm0yj2sn 890 6 the the DT cord-276598-tm0yj2sn 890 7 azide azide NN cord-276598-tm0yj2sn 890 8 anion anion NN cord-276598-tm0yj2sn 890 9 departs depart VBZ cord-276598-tm0yj2sn 890 10 as as IN cord-276598-tm0yj2sn 890 11 the the DT cord-276598-tm0yj2sn 890 12 leaving leave VBG cord-276598-tm0yj2sn 890 13 group group NN cord-276598-tm0yj2sn 890 14 to to TO cord-276598-tm0yj2sn 890 15 give give VB cord-276598-tm0yj2sn 890 16 a a DT cord-276598-tm0yj2sn 890 17 stable stable JJ cord-276598-tm0yj2sn 890 18 P p NN cord-276598-tm0yj2sn 890 19 - - HYPH cord-276598-tm0yj2sn 890 20 N n CD cord-276598-tm0yj2sn 890 21 product product NN cord-276598-tm0yj2sn 890 22 ( ( -LRB- cord-276598-tm0yj2sn 890 23 Scheme scheme NN cord-276598-tm0yj2sn 890 24 35 35 CD cord-276598-tm0yj2sn 890 25 ) ) -RRB- cord-276598-tm0yj2sn 890 26 . . . cord-276598-tm0yj2sn 891 1 Although although IN cord-276598-tm0yj2sn 891 2 the the DT cord-276598-tm0yj2sn 891 3 mechanism mechanism NN cord-276598-tm0yj2sn 891 4 looks look VBZ cord-276598-tm0yj2sn 891 5 highly highly RB cord-276598-tm0yj2sn 891 6 plausible plausible JJ cord-276598-tm0yj2sn 891 7 , , , cord-276598-tm0yj2sn 891 8 it -PRON- PRP cord-276598-tm0yj2sn 891 9 is be VBZ cord-276598-tm0yj2sn 891 10 noteworthy noteworthy JJ cord-276598-tm0yj2sn 891 11 that that IN cord-276598-tm0yj2sn 891 12 N n NN cord-276598-tm0yj2sn 891 13 3 3 CD cord-276598-tm0yj2sn 891 14 is be VBZ cord-276598-tm0yj2sn 891 15 highly highly RB cord-276598-tm0yj2sn 891 16 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 891 17 because because IN cord-276598-tm0yj2sn 891 18 in in IN cord-276598-tm0yj2sn 891 19 its -PRON- PRP$ cord-276598-tm0yj2sn 891 20 canonical canonical JJ cord-276598-tm0yj2sn 891 21 structure structure NN cord-276598-tm0yj2sn 891 22 , , , cord-276598-tm0yj2sn 891 23 one one CD cord-276598-tm0yj2sn 891 24 of of IN cord-276598-tm0yj2sn 891 25 the the DT cord-276598-tm0yj2sn 891 26 nitrogen nitrogen NN cord-276598-tm0yj2sn 891 27 atoms atom NNS cord-276598-tm0yj2sn 891 28 carries carry VBZ cord-276598-tm0yj2sn 891 29 a a DT cord-276598-tm0yj2sn 891 30 double double JJ cord-276598-tm0yj2sn 891 31 negative negative JJ cord-276598-tm0yj2sn 891 32 charge charge NN cord-276598-tm0yj2sn 891 33 ( ( -LRB- cord-276598-tm0yj2sn 891 34 N≡N n≡n NN cord-276598-tm0yj2sn 891 35 + + SYM cord-276598-tm0yj2sn 891 36 − − NN cord-276598-tm0yj2sn 891 37 N n CD cord-276598-tm0yj2sn 891 38 2− 2− CD cord-276598-tm0yj2sn 891 39 ) ) -RRB- cord-276598-tm0yj2sn 891 40 [ [ -LRB- cord-276598-tm0yj2sn 891 41 124 124 CD cord-276598-tm0yj2sn 891 42 ] ] -RRB- cord-276598-tm0yj2sn 891 43 , , , cord-276598-tm0yj2sn 891 44 which which WDT cord-276598-tm0yj2sn 891 45 makes make VBZ cord-276598-tm0yj2sn 891 46 it -PRON- PRP cord-276598-tm0yj2sn 891 47 stable stable JJ cord-276598-tm0yj2sn 891 48 and and CC cord-276598-tm0yj2sn 891 49 a a DT cord-276598-tm0yj2sn 891 50 poor poor JJ cord-276598-tm0yj2sn 891 51 leaving leave VBG cord-276598-tm0yj2sn 891 52 group group NN cord-276598-tm0yj2sn 891 53 as as IN cord-276598-tm0yj2sn 891 54 N n CD cord-276598-tm0yj2sn 891 55 3 3 CD cord-276598-tm0yj2sn 891 56 in in IN cord-276598-tm0yj2sn 891 57 the the DT cord-276598-tm0yj2sn 891 58 presence presence NN cord-276598-tm0yj2sn 891 59 of of IN cord-276598-tm0yj2sn 891 60 amine amine NN cord-276598-tm0yj2sn 891 61 [ [ -LRB- cord-276598-tm0yj2sn 891 62 125 125 CD cord-276598-tm0yj2sn 891 63 ] ] -RRB- cord-276598-tm0yj2sn 891 64 . . . cord-276598-tm0yj2sn 892 1 In in IN cord-276598-tm0yj2sn 892 2 addition addition NN cord-276598-tm0yj2sn 892 3 , , , cord-276598-tm0yj2sn 892 4 the the DT cord-276598-tm0yj2sn 892 5 mechanism mechanism NN cord-276598-tm0yj2sn 892 6 does do VBZ cord-276598-tm0yj2sn 892 7 account account VB cord-276598-tm0yj2sn 892 8 for for IN cord-276598-tm0yj2sn 892 9 the the DT cord-276598-tm0yj2sn 892 10 potentially potentially RB cord-276598-tm0yj2sn 892 11 explosive explosive JJ cord-276598-tm0yj2sn 892 12 HN HN NNP cord-276598-tm0yj2sn 892 13 3 3 CD cord-276598-tm0yj2sn 892 14 in in IN cord-276598-tm0yj2sn 892 15 a a DT cord-276598-tm0yj2sn 892 16 closed closed JJ cord-276598-tm0yj2sn 892 17 flask flask NN cord-276598-tm0yj2sn 892 18 at at IN cord-276598-tm0yj2sn 892 19 120 120 CD cord-276598-tm0yj2sn 892 20 • • NNS cord-276598-tm0yj2sn 892 21 C. c. NN cord-276598-tm0yj2sn 893 1 However however RB cord-276598-tm0yj2sn 893 2 , , , cord-276598-tm0yj2sn 893 3 it -PRON- PRP cord-276598-tm0yj2sn 893 4 is be VBZ cord-276598-tm0yj2sn 893 5 possible possible JJ cord-276598-tm0yj2sn 893 6 that that IN cord-276598-tm0yj2sn 893 7 in in IN cord-276598-tm0yj2sn 893 8 the the DT cord-276598-tm0yj2sn 893 9 reaction reaction NN cord-276598-tm0yj2sn 893 10 process process NN cord-276598-tm0yj2sn 893 11 , , , cord-276598-tm0yj2sn 893 12 the the DT cord-276598-tm0yj2sn 893 13 azide azide NN cord-276598-tm0yj2sn 893 14 is be VBZ cord-276598-tm0yj2sn 893 15 first first RB cord-276598-tm0yj2sn 893 16 reduced reduce VBN cord-276598-tm0yj2sn 893 17 or or CC cord-276598-tm0yj2sn 893 18 decomposed decompose VBN cord-276598-tm0yj2sn 893 19 to to IN cord-276598-tm0yj2sn 893 20 a a DT cord-276598-tm0yj2sn 893 21 nitrene nitrene JJ cord-276598-tm0yj2sn 893 22 phosphonate phosphonate NNP cord-276598-tm0yj2sn 893 23 radical radical JJ cord-276598-tm0yj2sn 893 24 ( ( -LRB- cord-276598-tm0yj2sn 893 25 ( ( -LRB- cord-276598-tm0yj2sn 893 26 RO RO NNP cord-276598-tm0yj2sn 893 27 ) ) -RRB- cord-276598-tm0yj2sn 893 28 2 2 CD cord-276598-tm0yj2sn 893 29 P(O)N P(O)N NNP cord-276598-tm0yj2sn 893 30 ; ; : cord-276598-tm0yj2sn 893 31 R r NN cord-276598-tm0yj2sn 893 32 = = NN cord-276598-tm0yj2sn 893 33 alkyl alkyl NN cord-276598-tm0yj2sn 893 34 , , , cord-276598-tm0yj2sn 893 35 Ph Ph NNP cord-276598-tm0yj2sn 893 36 ) ) -RRB- cord-276598-tm0yj2sn 893 37 , , , cord-276598-tm0yj2sn 893 38 while while IN cord-276598-tm0yj2sn 893 39 N n CD cord-276598-tm0yj2sn 893 40 2 2 CD cord-276598-tm0yj2sn 893 41 is be VBZ cord-276598-tm0yj2sn 893 42 liberated liberate VBN cord-276598-tm0yj2sn 893 43 . . . cord-276598-tm0yj2sn 894 1 In in IN cord-276598-tm0yj2sn 894 2 the the DT cord-276598-tm0yj2sn 894 3 second second JJ cord-276598-tm0yj2sn 894 4 step step NN cord-276598-tm0yj2sn 894 5 , , , cord-276598-tm0yj2sn 894 6 the the DT cord-276598-tm0yj2sn 894 7 electrophilic electrophilic JJ cord-276598-tm0yj2sn 894 8 nitrene nitrene NNP cord-276598-tm0yj2sn 894 9 phosphonate phosphonate NNP cord-276598-tm0yj2sn 894 10 radical radical NNP cord-276598-tm0yj2sn 894 11 reacts react VBZ cord-276598-tm0yj2sn 894 12 with with IN cord-276598-tm0yj2sn 894 13 or or CC cord-276598-tm0yj2sn 894 14 is be VBZ cord-276598-tm0yj2sn 894 15 substituted substitute VBN cord-276598-tm0yj2sn 894 16 by by IN cord-276598-tm0yj2sn 894 17 the the DT cord-276598-tm0yj2sn 894 18 nucleophile nucleophile JJ cord-276598-tm0yj2sn 894 19 amine amine NN cord-276598-tm0yj2sn 894 20 to to TO cord-276598-tm0yj2sn 894 21 give give VB cord-276598-tm0yj2sn 894 22 the the DT cord-276598-tm0yj2sn 894 23 product product NN cord-276598-tm0yj2sn 894 24 . . . cord-276598-tm0yj2sn 895 1 Molecules molecule NNS cord-276598-tm0yj2sn 895 2 2020 2020 CD cord-276598-tm0yj2sn 895 3 , , , cord-276598-tm0yj2sn 895 4 25 25 CD cord-276598-tm0yj2sn 895 5 , , , cord-276598-tm0yj2sn 895 6 x x NN cord-276598-tm0yj2sn 895 7 FOR for IN cord-276598-tm0yj2sn 895 8 PEER peer NN cord-276598-tm0yj2sn 895 9 REVIEW REVIEW NNP cord-276598-tm0yj2sn 895 10 28 28 CD cord-276598-tm0yj2sn 895 11 of of IN cord-276598-tm0yj2sn 895 12 37 37 CD cord-276598-tm0yj2sn 895 13 alkyl alkyl NN cord-276598-tm0yj2sn 895 14 , , , cord-276598-tm0yj2sn 895 15 Ph Ph NNP cord-276598-tm0yj2sn 895 16 ) ) -RRB- cord-276598-tm0yj2sn 895 17 , , , cord-276598-tm0yj2sn 895 18 while while IN cord-276598-tm0yj2sn 895 19 N2 N2 NNP cord-276598-tm0yj2sn 895 20 is be VBZ cord-276598-tm0yj2sn 895 21 liberated liberate VBN cord-276598-tm0yj2sn 895 22 . . . cord-276598-tm0yj2sn 896 1 In in IN cord-276598-tm0yj2sn 896 2 the the DT cord-276598-tm0yj2sn 896 3 second second JJ cord-276598-tm0yj2sn 896 4 step step NN cord-276598-tm0yj2sn 896 5 , , , cord-276598-tm0yj2sn 896 6 the the DT cord-276598-tm0yj2sn 896 7 electrophilic electrophilic JJ cord-276598-tm0yj2sn 896 8 nitrene nitrene NNP cord-276598-tm0yj2sn 896 9 phosphonate phosphonate NNP cord-276598-tm0yj2sn 896 10 radical radical NNP cord-276598-tm0yj2sn 896 11 reacts react VBZ cord-276598-tm0yj2sn 896 12 with with IN cord-276598-tm0yj2sn 896 13 or or CC cord-276598-tm0yj2sn 896 14 is be VBZ cord-276598-tm0yj2sn 896 15 substituted substitute VBN cord-276598-tm0yj2sn 896 16 by by IN cord-276598-tm0yj2sn 896 17 the the DT cord-276598-tm0yj2sn 896 18 nucleophile nucleophile JJ cord-276598-tm0yj2sn 896 19 amine amine NN cord-276598-tm0yj2sn 896 20 to to TO cord-276598-tm0yj2sn 896 21 give give VB cord-276598-tm0yj2sn 896 22 the the DT cord-276598-tm0yj2sn 896 23 product product NN cord-276598-tm0yj2sn 896 24 . . . cord-276598-tm0yj2sn 897 1 Proposed propose VBN cord-276598-tm0yj2sn 897 2 mechanism mechanism NN cord-276598-tm0yj2sn 897 3 for for IN cord-276598-tm0yj2sn 897 4 an an DT cord-276598-tm0yj2sn 897 5 organic organic JJ cord-276598-tm0yj2sn 897 6 azide azide NN cord-276598-tm0yj2sn 897 7 route route NN cord-276598-tm0yj2sn 897 8 to to IN cord-276598-tm0yj2sn 897 9 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 897 10 . . . cord-276598-tm0yj2sn 898 1 The the DT cord-276598-tm0yj2sn 898 2 proposed propose VBN cord-276598-tm0yj2sn 898 3 mechanism mechanism NN cord-276598-tm0yj2sn 898 4 of of IN cord-276598-tm0yj2sn 898 5 the the DT cord-276598-tm0yj2sn 898 6 reaction reaction NN cord-276598-tm0yj2sn 898 7 for for IN cord-276598-tm0yj2sn 898 8 the the DT cord-276598-tm0yj2sn 898 9 nitro nitro NN cord-276598-tm0yj2sn 898 10 - - HYPH cord-276598-tm0yj2sn 898 11 group group NN cord-276598-tm0yj2sn 898 12 reduction reduction NN cord-276598-tm0yj2sn 898 13 route route NN cord-276598-tm0yj2sn 898 14 involves involve VBZ cord-276598-tm0yj2sn 898 15 the the DT cord-276598-tm0yj2sn 898 16 reduction reduction NN cord-276598-tm0yj2sn 898 17 of of IN cord-276598-tm0yj2sn 898 18 nitrobenzene nitrobenzene NN cord-276598-tm0yj2sn 898 19 in in IN cord-276598-tm0yj2sn 898 20 the the DT cord-276598-tm0yj2sn 898 21 presence presence NN cord-276598-tm0yj2sn 898 22 of of IN cord-276598-tm0yj2sn 898 23 ( ( -LRB- cord-276598-tm0yj2sn 898 24 RO)3P RO)3P NNP cord-276598-tm0yj2sn 898 25 ( ( -LRB- cord-276598-tm0yj2sn 898 26 R r NN cord-276598-tm0yj2sn 898 27 = = NN cord-276598-tm0yj2sn 898 28 alkyl alkyl NN cord-276598-tm0yj2sn 898 29 ) ) -RRB- cord-276598-tm0yj2sn 898 30 to to TO cord-276598-tm0yj2sn 898 31 give give VB cord-276598-tm0yj2sn 898 32 nitrosobenzene nitrosobenzene NN cord-276598-tm0yj2sn 898 33 with with IN cord-276598-tm0yj2sn 898 34 a a DT cord-276598-tm0yj2sn 898 35 phosphate phosphate NN cord-276598-tm0yj2sn 898 36 side side NN cord-276598-tm0yj2sn 898 37 product product NN cord-276598-tm0yj2sn 898 38 ( ( -LRB- cord-276598-tm0yj2sn 898 39 Scheme scheme NN cord-276598-tm0yj2sn 898 40 36 36 CD cord-276598-tm0yj2sn 898 41 ) ) -RRB- cord-276598-tm0yj2sn 898 42 [ [ -LRB- cord-276598-tm0yj2sn 898 43 118 118 CD cord-276598-tm0yj2sn 898 44 ] ] -RRB- cord-276598-tm0yj2sn 898 45 . . . cord-276598-tm0yj2sn 899 1 In in IN cord-276598-tm0yj2sn 899 2 the the DT cord-276598-tm0yj2sn 899 3 second second JJ cord-276598-tm0yj2sn 899 4 step step NN cord-276598-tm0yj2sn 899 5 , , , cord-276598-tm0yj2sn 899 6 the the DT cord-276598-tm0yj2sn 899 7 nitrosobenzene nitrosobenzene NN cord-276598-tm0yj2sn 899 8 is be VBZ cord-276598-tm0yj2sn 899 9 reduced reduce VBN cord-276598-tm0yj2sn 899 10 further further RB cord-276598-tm0yj2sn 899 11 in in IN cord-276598-tm0yj2sn 899 12 the the DT cord-276598-tm0yj2sn 899 13 presence presence NN cord-276598-tm0yj2sn 899 14 of of IN cord-276598-tm0yj2sn 899 15 another another DT cord-276598-tm0yj2sn 899 16 equivalent equivalent NN cord-276598-tm0yj2sn 899 17 of of IN cord-276598-tm0yj2sn 899 18 ( ( -LRB- cord-276598-tm0yj2sn 899 19 RO)3P RO)3P NNP cord-276598-tm0yj2sn 899 20 , , , cord-276598-tm0yj2sn 899 21 generating generate VBG cord-276598-tm0yj2sn 899 22 phenylnitride phenylnitride NN cord-276598-tm0yj2sn 899 23 with with IN cord-276598-tm0yj2sn 899 24 another another DT cord-276598-tm0yj2sn 899 25 phosphate phosphate NN cord-276598-tm0yj2sn 899 26 side side NN cord-276598-tm0yj2sn 899 27 product product NN cord-276598-tm0yj2sn 899 28 . . . cord-276598-tm0yj2sn 900 1 A a DT cord-276598-tm0yj2sn 900 2 further further JJ cord-276598-tm0yj2sn 900 3 reaction reaction NN cord-276598-tm0yj2sn 900 4 of of IN cord-276598-tm0yj2sn 900 5 ( ( -LRB- cord-276598-tm0yj2sn 900 6 RO)3P RO)3P NNP cord-276598-tm0yj2sn 900 7 ( ( -LRB- cord-276598-tm0yj2sn 900 8 R r NN cord-276598-tm0yj2sn 900 9 = = NN cord-276598-tm0yj2sn 900 10 alkyl alkyl NN cord-276598-tm0yj2sn 900 11 ) ) -RRB- cord-276598-tm0yj2sn 901 1 with with IN cord-276598-tm0yj2sn 901 2 the the DT cord-276598-tm0yj2sn 901 3 basic basic JJ cord-276598-tm0yj2sn 901 4 phenylnitride phenylnitride NN cord-276598-tm0yj2sn 901 5 generates generate VBZ cord-276598-tm0yj2sn 901 6 a a DT cord-276598-tm0yj2sn 901 7 trialkyl trialkyl JJ cord-276598-tm0yj2sn 901 8 phenylphosphorimidate phenylphosphorimidate JJ cord-276598-tm0yj2sn 901 9 intermediate intermediate NN cord-276598-tm0yj2sn 901 10 , , , cord-276598-tm0yj2sn 901 11 which which WDT cord-276598-tm0yj2sn 901 12 undergoes undergo VBZ cord-276598-tm0yj2sn 901 13 hydrolysis hydrolysis NN cord-276598-tm0yj2sn 901 14 to to TO cord-276598-tm0yj2sn 901 15 give give VB cord-276598-tm0yj2sn 901 16 the the DT cord-276598-tm0yj2sn 901 17 desired desire VBN cord-276598-tm0yj2sn 901 18 N N NNP cord-276598-tm0yj2sn 901 19 - - HYPH cord-276598-tm0yj2sn 901 20 arylphosphoramidate arylphosphoramidate JJ cord-276598-tm0yj2sn 901 21 product product NN cord-276598-tm0yj2sn 901 22 . . . cord-276598-tm0yj2sn 902 1 Experiments experiment NNS cord-276598-tm0yj2sn 902 2 to to TO cord-276598-tm0yj2sn 902 3 verify verify VB cord-276598-tm0yj2sn 902 4 the the DT cord-276598-tm0yj2sn 902 5 proposed propose VBN cord-276598-tm0yj2sn 902 6 mechanism mechanism NN cord-276598-tm0yj2sn 902 7 using use VBG cord-276598-tm0yj2sn 902 8 aniline aniline NN cord-276598-tm0yj2sn 902 9 in in IN cord-276598-tm0yj2sn 902 10 the the DT cord-276598-tm0yj2sn 902 11 presence presence NN cord-276598-tm0yj2sn 902 12 of of IN cord-276598-tm0yj2sn 902 13 excess excess JJ cord-276598-tm0yj2sn 902 14 triethyl triethyl NNP cord-276598-tm0yj2sn 902 15 phosphite phosphite NNP cord-276598-tm0yj2sn 902 16 or or CC cord-276598-tm0yj2sn 902 17 triethyl triethyl NNP cord-276598-tm0yj2sn 902 18 phosphate phosphate NN cord-276598-tm0yj2sn 902 19 did do VBD cord-276598-tm0yj2sn 902 20 not not RB cord-276598-tm0yj2sn 902 21 yield yield VB cord-276598-tm0yj2sn 902 22 the the DT cord-276598-tm0yj2sn 902 23 desired desire VBN cord-276598-tm0yj2sn 902 24 product product NN cord-276598-tm0yj2sn 902 25 under under IN cord-276598-tm0yj2sn 902 26 the the DT cord-276598-tm0yj2sn 902 27 optimized optimize VBN cord-276598-tm0yj2sn 902 28 conditions condition NNS cord-276598-tm0yj2sn 902 29 , , , cord-276598-tm0yj2sn 902 30 suggesting suggest VBG cord-276598-tm0yj2sn 902 31 that that IN cord-276598-tm0yj2sn 902 32 the the DT cord-276598-tm0yj2sn 902 33 reaction reaction NN cord-276598-tm0yj2sn 902 34 proceeds proceed VBZ cord-276598-tm0yj2sn 902 35 via via IN cord-276598-tm0yj2sn 902 36 reduction reduction NN cord-276598-tm0yj2sn 902 37 of of IN cord-276598-tm0yj2sn 902 38 the the DT cord-276598-tm0yj2sn 902 39 nitro nitro NN cord-276598-tm0yj2sn 902 40 group group NN cord-276598-tm0yj2sn 902 41 to to IN cord-276598-tm0yj2sn 902 42 N n CD cord-276598-tm0yj2sn 902 43 2− 2− CD cord-276598-tm0yj2sn 902 44 and and CC cord-276598-tm0yj2sn 902 45 that that IN cord-276598-tm0yj2sn 902 46 the the DT cord-276598-tm0yj2sn 902 47 product product NN cord-276598-tm0yj2sn 902 48 is be VBZ cord-276598-tm0yj2sn 902 49 not not RB cord-276598-tm0yj2sn 902 50 formed form VBN cord-276598-tm0yj2sn 902 51 from from IN cord-276598-tm0yj2sn 902 52 phosphate phosphate NN cord-276598-tm0yj2sn 902 53 . . . cord-276598-tm0yj2sn 903 1 Scheme scheme NN cord-276598-tm0yj2sn 903 2 36 36 CD cord-276598-tm0yj2sn 903 3 . . . cord-276598-tm0yj2sn 904 1 Proposed propose VBN cord-276598-tm0yj2sn 904 2 mechanism mechanism NN cord-276598-tm0yj2sn 904 3 for for IN cord-276598-tm0yj2sn 904 4 reduction reduction NN cord-276598-tm0yj2sn 904 5 of of IN cord-276598-tm0yj2sn 904 6 the the DT cord-276598-tm0yj2sn 904 7 nitro nitro NN cord-276598-tm0yj2sn 904 8 - - HYPH cord-276598-tm0yj2sn 904 9 group group NN cord-276598-tm0yj2sn 904 10 route route NN cord-276598-tm0yj2sn 904 11 to to IN cord-276598-tm0yj2sn 904 12 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 904 13 . . . cord-276598-tm0yj2sn 905 1 The the DT cord-276598-tm0yj2sn 905 2 plausible plausible JJ cord-276598-tm0yj2sn 905 3 two two CD cord-276598-tm0yj2sn 905 4 - - HYPH cord-276598-tm0yj2sn 905 5 step step NN cord-276598-tm0yj2sn 905 6 mechanistic mechanistic JJ cord-276598-tm0yj2sn 905 7 process process NN cord-276598-tm0yj2sn 905 8 suggested suggest VBN cord-276598-tm0yj2sn 905 9 by by IN cord-276598-tm0yj2sn 905 10 Hackenberger Hackenberger NNP cord-276598-tm0yj2sn 905 11 's 's POS cord-276598-tm0yj2sn 905 12 group group NN cord-276598-tm0yj2sn 905 13 for for IN cord-276598-tm0yj2sn 905 14 the the DT cord-276598-tm0yj2sn 905 15 Scheme Scheme NNP cord-276598-tm0yj2sn 905 16 35 35 CD cord-276598-tm0yj2sn 905 17 . . . cord-276598-tm0yj2sn 906 1 Proposed propose VBN cord-276598-tm0yj2sn 906 2 mechanism mechanism NN cord-276598-tm0yj2sn 906 3 for for IN cord-276598-tm0yj2sn 906 4 an an DT cord-276598-tm0yj2sn 906 5 organic organic JJ cord-276598-tm0yj2sn 906 6 azide azide NN cord-276598-tm0yj2sn 906 7 route route NN cord-276598-tm0yj2sn 906 8 to to IN cord-276598-tm0yj2sn 906 9 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 906 10 . . . cord-276598-tm0yj2sn 907 1 The the DT cord-276598-tm0yj2sn 907 2 proposed propose VBN cord-276598-tm0yj2sn 907 3 mechanism mechanism NN cord-276598-tm0yj2sn 907 4 of of IN cord-276598-tm0yj2sn 907 5 the the DT cord-276598-tm0yj2sn 907 6 reaction reaction NN cord-276598-tm0yj2sn 907 7 for for IN cord-276598-tm0yj2sn 907 8 the the DT cord-276598-tm0yj2sn 907 9 nitro nitro NN cord-276598-tm0yj2sn 907 10 - - HYPH cord-276598-tm0yj2sn 907 11 group group NN cord-276598-tm0yj2sn 907 12 reduction reduction NN cord-276598-tm0yj2sn 907 13 route route NN cord-276598-tm0yj2sn 907 14 involves involve VBZ cord-276598-tm0yj2sn 907 15 the the DT cord-276598-tm0yj2sn 907 16 reduction reduction NN cord-276598-tm0yj2sn 907 17 of of IN cord-276598-tm0yj2sn 907 18 nitrobenzene nitrobenzene NN cord-276598-tm0yj2sn 907 19 in in IN cord-276598-tm0yj2sn 907 20 the the DT cord-276598-tm0yj2sn 907 21 presence presence NN cord-276598-tm0yj2sn 907 22 of of IN cord-276598-tm0yj2sn 907 23 ( ( -LRB- cord-276598-tm0yj2sn 907 24 RO ro NN cord-276598-tm0yj2sn 907 25 ) ) -RRB- cord-276598-tm0yj2sn 907 26 3 3 CD cord-276598-tm0yj2sn 907 27 P p NN cord-276598-tm0yj2sn 907 28 ( ( -LRB- cord-276598-tm0yj2sn 907 29 R r NN cord-276598-tm0yj2sn 907 30 = = NN cord-276598-tm0yj2sn 907 31 alkyl alkyl NN cord-276598-tm0yj2sn 907 32 ) ) -RRB- cord-276598-tm0yj2sn 907 33 to to TO cord-276598-tm0yj2sn 907 34 give give VB cord-276598-tm0yj2sn 907 35 nitrosobenzene nitrosobenzene NN cord-276598-tm0yj2sn 907 36 with with IN cord-276598-tm0yj2sn 907 37 a a DT cord-276598-tm0yj2sn 907 38 phosphate phosphate NN cord-276598-tm0yj2sn 907 39 side side NN cord-276598-tm0yj2sn 907 40 product product NN cord-276598-tm0yj2sn 907 41 ( ( -LRB- cord-276598-tm0yj2sn 907 42 Scheme scheme NN cord-276598-tm0yj2sn 907 43 36 36 CD cord-276598-tm0yj2sn 907 44 ) ) -RRB- cord-276598-tm0yj2sn 907 45 [ [ -LRB- cord-276598-tm0yj2sn 907 46 118 118 CD cord-276598-tm0yj2sn 907 47 ] ] -RRB- cord-276598-tm0yj2sn 907 48 . . . cord-276598-tm0yj2sn 908 1 In in IN cord-276598-tm0yj2sn 908 2 the the DT cord-276598-tm0yj2sn 908 3 second second JJ cord-276598-tm0yj2sn 908 4 step step NN cord-276598-tm0yj2sn 908 5 , , , cord-276598-tm0yj2sn 908 6 the the DT cord-276598-tm0yj2sn 908 7 nitrosobenzene nitrosobenzene NN cord-276598-tm0yj2sn 908 8 is be VBZ cord-276598-tm0yj2sn 908 9 reduced reduce VBN cord-276598-tm0yj2sn 908 10 further further RB cord-276598-tm0yj2sn 908 11 in in IN cord-276598-tm0yj2sn 908 12 the the DT cord-276598-tm0yj2sn 908 13 presence presence NN cord-276598-tm0yj2sn 908 14 of of IN cord-276598-tm0yj2sn 908 15 another another DT cord-276598-tm0yj2sn 908 16 equivalent equivalent NN cord-276598-tm0yj2sn 908 17 of of IN cord-276598-tm0yj2sn 908 18 ( ( -LRB- cord-276598-tm0yj2sn 908 19 RO ro NN cord-276598-tm0yj2sn 908 20 ) ) -RRB- cord-276598-tm0yj2sn 908 21 3 3 CD cord-276598-tm0yj2sn 908 22 P p NN cord-276598-tm0yj2sn 908 23 , , , cord-276598-tm0yj2sn 908 24 generating generate VBG cord-276598-tm0yj2sn 908 25 phenylnitride phenylnitride NN cord-276598-tm0yj2sn 908 26 with with IN cord-276598-tm0yj2sn 908 27 another another DT cord-276598-tm0yj2sn 908 28 phosphate phosphate NN cord-276598-tm0yj2sn 908 29 side side NN cord-276598-tm0yj2sn 908 30 product product NN cord-276598-tm0yj2sn 908 31 . . . cord-276598-tm0yj2sn 909 1 A a DT cord-276598-tm0yj2sn 909 2 further further JJ cord-276598-tm0yj2sn 909 3 reaction reaction NN cord-276598-tm0yj2sn 909 4 of of IN cord-276598-tm0yj2sn 909 5 ( ( -LRB- cord-276598-tm0yj2sn 909 6 RO ro NN cord-276598-tm0yj2sn 909 7 ) ) -RRB- cord-276598-tm0yj2sn 909 8 3 3 CD cord-276598-tm0yj2sn 909 9 P p NN cord-276598-tm0yj2sn 909 10 ( ( -LRB- cord-276598-tm0yj2sn 909 11 R r NN cord-276598-tm0yj2sn 909 12 = = NN cord-276598-tm0yj2sn 909 13 alkyl alkyl NN cord-276598-tm0yj2sn 909 14 ) ) -RRB- cord-276598-tm0yj2sn 909 15 with with IN cord-276598-tm0yj2sn 909 16 the the DT cord-276598-tm0yj2sn 909 17 basic basic JJ cord-276598-tm0yj2sn 909 18 phenylnitride phenylnitride NN cord-276598-tm0yj2sn 909 19 generates generate VBZ cord-276598-tm0yj2sn 909 20 a a DT cord-276598-tm0yj2sn 909 21 trialkyl trialkyl JJ cord-276598-tm0yj2sn 909 22 phenylphosphorimidate phenylphosphorimidate JJ cord-276598-tm0yj2sn 909 23 intermediate intermediate NN cord-276598-tm0yj2sn 909 24 , , , cord-276598-tm0yj2sn 909 25 which which WDT cord-276598-tm0yj2sn 909 26 undergoes undergo VBZ cord-276598-tm0yj2sn 909 27 hydrolysis hydrolysis NN cord-276598-tm0yj2sn 909 28 to to TO cord-276598-tm0yj2sn 909 29 give give VB cord-276598-tm0yj2sn 909 30 the the DT cord-276598-tm0yj2sn 909 31 desired desire VBN cord-276598-tm0yj2sn 909 32 N N NNP cord-276598-tm0yj2sn 909 33 - - HYPH cord-276598-tm0yj2sn 909 34 arylphosphoramidate arylphosphoramidate JJ cord-276598-tm0yj2sn 909 35 product product NN cord-276598-tm0yj2sn 909 36 . . . cord-276598-tm0yj2sn 910 1 Experiments experiment NNS cord-276598-tm0yj2sn 910 2 to to TO cord-276598-tm0yj2sn 910 3 verify verify VB cord-276598-tm0yj2sn 910 4 the the DT cord-276598-tm0yj2sn 910 5 proposed propose VBN cord-276598-tm0yj2sn 910 6 mechanism mechanism NN cord-276598-tm0yj2sn 910 7 using use VBG cord-276598-tm0yj2sn 910 8 aniline aniline NN cord-276598-tm0yj2sn 910 9 in in IN cord-276598-tm0yj2sn 910 10 the the DT cord-276598-tm0yj2sn 910 11 presence presence NN cord-276598-tm0yj2sn 910 12 of of IN cord-276598-tm0yj2sn 910 13 excess excess JJ cord-276598-tm0yj2sn 910 14 triethyl triethyl NNP cord-276598-tm0yj2sn 910 15 phosphite phosphite NNP cord-276598-tm0yj2sn 910 16 or or CC cord-276598-tm0yj2sn 910 17 triethyl triethyl NNP cord-276598-tm0yj2sn 910 18 phosphate phosphate NN cord-276598-tm0yj2sn 910 19 did do VBD cord-276598-tm0yj2sn 910 20 not not RB cord-276598-tm0yj2sn 910 21 yield yield VB cord-276598-tm0yj2sn 910 22 the the DT cord-276598-tm0yj2sn 910 23 desired desire VBN cord-276598-tm0yj2sn 910 24 product product NN cord-276598-tm0yj2sn 910 25 under under IN cord-276598-tm0yj2sn 910 26 the the DT cord-276598-tm0yj2sn 910 27 optimized optimize VBN cord-276598-tm0yj2sn 910 28 conditions condition NNS cord-276598-tm0yj2sn 910 29 , , , cord-276598-tm0yj2sn 910 30 suggesting suggest VBG cord-276598-tm0yj2sn 910 31 that that IN cord-276598-tm0yj2sn 910 32 the the DT cord-276598-tm0yj2sn 910 33 reaction reaction NN cord-276598-tm0yj2sn 910 34 proceeds proceed VBZ cord-276598-tm0yj2sn 910 35 via via IN cord-276598-tm0yj2sn 910 36 reduction reduction NN cord-276598-tm0yj2sn 910 37 of of IN cord-276598-tm0yj2sn 910 38 the the DT cord-276598-tm0yj2sn 910 39 nitro nitro NN cord-276598-tm0yj2sn 910 40 group group NN cord-276598-tm0yj2sn 910 41 to to IN cord-276598-tm0yj2sn 910 42 N n CD cord-276598-tm0yj2sn 910 43 2− 2− CD cord-276598-tm0yj2sn 910 44 and and CC cord-276598-tm0yj2sn 910 45 that that IN cord-276598-tm0yj2sn 910 46 the the DT cord-276598-tm0yj2sn 910 47 product product NN cord-276598-tm0yj2sn 910 48 is be VBZ cord-276598-tm0yj2sn 910 49 not not RB cord-276598-tm0yj2sn 910 50 formed form VBN cord-276598-tm0yj2sn 910 51 from from IN cord-276598-tm0yj2sn 910 52 phosphate phosphate NN cord-276598-tm0yj2sn 910 53 . . . cord-276598-tm0yj2sn 911 1 in in IN cord-276598-tm0yj2sn 911 2 the the DT cord-276598-tm0yj2sn 911 3 presence presence NN cord-276598-tm0yj2sn 911 4 of of IN cord-276598-tm0yj2sn 911 5 another another DT cord-276598-tm0yj2sn 911 6 equivalent equivalent NN cord-276598-tm0yj2sn 911 7 of of IN cord-276598-tm0yj2sn 911 8 ( ( -LRB- cord-276598-tm0yj2sn 911 9 RO)3P RO)3P NNP cord-276598-tm0yj2sn 911 10 , , , cord-276598-tm0yj2sn 911 11 generating generate VBG cord-276598-tm0yj2sn 911 12 phenylnitride phenylnitride NN cord-276598-tm0yj2sn 911 13 with with IN cord-276598-tm0yj2sn 911 14 another another DT cord-276598-tm0yj2sn 911 15 phosphate phosphate NN cord-276598-tm0yj2sn 911 16 side side NN cord-276598-tm0yj2sn 911 17 product product NN cord-276598-tm0yj2sn 911 18 . . . cord-276598-tm0yj2sn 912 1 A a DT cord-276598-tm0yj2sn 912 2 further further JJ cord-276598-tm0yj2sn 912 3 reaction reaction NN cord-276598-tm0yj2sn 912 4 of of IN cord-276598-tm0yj2sn 912 5 ( ( -LRB- cord-276598-tm0yj2sn 912 6 RO)3P RO)3P NNP cord-276598-tm0yj2sn 912 7 ( ( -LRB- cord-276598-tm0yj2sn 912 8 R r NN cord-276598-tm0yj2sn 912 9 = = NN cord-276598-tm0yj2sn 912 10 alkyl alkyl NN cord-276598-tm0yj2sn 912 11 ) ) -RRB- cord-276598-tm0yj2sn 913 1 with with IN cord-276598-tm0yj2sn 913 2 the the DT cord-276598-tm0yj2sn 913 3 basic basic JJ cord-276598-tm0yj2sn 913 4 phenylnitride phenylnitride NN cord-276598-tm0yj2sn 913 5 generates generate VBZ cord-276598-tm0yj2sn 913 6 a a DT cord-276598-tm0yj2sn 913 7 trialkyl trialkyl JJ cord-276598-tm0yj2sn 913 8 phenylphosphorimidate phenylphosphorimidate JJ cord-276598-tm0yj2sn 913 9 intermediate intermediate NN cord-276598-tm0yj2sn 913 10 , , , cord-276598-tm0yj2sn 913 11 which which WDT cord-276598-tm0yj2sn 913 12 undergoes undergo VBZ cord-276598-tm0yj2sn 913 13 hydrolysis hydrolysis NN cord-276598-tm0yj2sn 913 14 to to TO cord-276598-tm0yj2sn 913 15 give give VB cord-276598-tm0yj2sn 913 16 the the DT cord-276598-tm0yj2sn 913 17 desired desire VBN cord-276598-tm0yj2sn 913 18 N N NNP cord-276598-tm0yj2sn 913 19 - - HYPH cord-276598-tm0yj2sn 913 20 arylphosphoramidate arylphosphoramidate JJ cord-276598-tm0yj2sn 913 21 product product NN cord-276598-tm0yj2sn 913 22 . . . cord-276598-tm0yj2sn 914 1 Experiments experiment NNS cord-276598-tm0yj2sn 914 2 to to TO cord-276598-tm0yj2sn 914 3 verify verify VB cord-276598-tm0yj2sn 914 4 the the DT cord-276598-tm0yj2sn 914 5 proposed propose VBN cord-276598-tm0yj2sn 914 6 mechanism mechanism NN cord-276598-tm0yj2sn 914 7 using use VBG cord-276598-tm0yj2sn 914 8 aniline aniline NN cord-276598-tm0yj2sn 914 9 in in IN cord-276598-tm0yj2sn 914 10 the the DT cord-276598-tm0yj2sn 914 11 presence presence NN cord-276598-tm0yj2sn 914 12 of of IN cord-276598-tm0yj2sn 914 13 excess excess JJ cord-276598-tm0yj2sn 914 14 triethyl triethyl NNP cord-276598-tm0yj2sn 914 15 phosphite phosphite NNP cord-276598-tm0yj2sn 914 16 or or CC cord-276598-tm0yj2sn 914 17 triethyl triethyl NNP cord-276598-tm0yj2sn 914 18 phosphate phosphate NN cord-276598-tm0yj2sn 914 19 did do VBD cord-276598-tm0yj2sn 914 20 not not RB cord-276598-tm0yj2sn 914 21 yield yield VB cord-276598-tm0yj2sn 914 22 the the DT cord-276598-tm0yj2sn 914 23 desired desire VBN cord-276598-tm0yj2sn 914 24 product product NN cord-276598-tm0yj2sn 914 25 under under IN cord-276598-tm0yj2sn 914 26 the the DT cord-276598-tm0yj2sn 914 27 optimized optimize VBN cord-276598-tm0yj2sn 914 28 conditions condition NNS cord-276598-tm0yj2sn 914 29 , , , cord-276598-tm0yj2sn 914 30 suggesting suggest VBG cord-276598-tm0yj2sn 914 31 that that IN cord-276598-tm0yj2sn 914 32 the the DT cord-276598-tm0yj2sn 914 33 reaction reaction NN cord-276598-tm0yj2sn 914 34 proceeds proceed VBZ cord-276598-tm0yj2sn 914 35 via via IN cord-276598-tm0yj2sn 914 36 reduction reduction NN cord-276598-tm0yj2sn 914 37 of of IN cord-276598-tm0yj2sn 914 38 the the DT cord-276598-tm0yj2sn 914 39 nitro nitro NN cord-276598-tm0yj2sn 914 40 group group NN cord-276598-tm0yj2sn 914 41 to to IN cord-276598-tm0yj2sn 914 42 N n CD cord-276598-tm0yj2sn 914 43 2− 2− CD cord-276598-tm0yj2sn 914 44 and and CC cord-276598-tm0yj2sn 914 45 that that IN cord-276598-tm0yj2sn 914 46 the the DT cord-276598-tm0yj2sn 914 47 product product NN cord-276598-tm0yj2sn 914 48 is be VBZ cord-276598-tm0yj2sn 914 49 not not RB cord-276598-tm0yj2sn 914 50 formed form VBN cord-276598-tm0yj2sn 914 51 from from IN cord-276598-tm0yj2sn 914 52 phosphate phosphate NN cord-276598-tm0yj2sn 914 53 . . . cord-276598-tm0yj2sn 915 1 Scheme scheme NN cord-276598-tm0yj2sn 915 2 36 36 CD cord-276598-tm0yj2sn 915 3 . . . cord-276598-tm0yj2sn 916 1 Proposed propose VBN cord-276598-tm0yj2sn 916 2 mechanism mechanism NN cord-276598-tm0yj2sn 916 3 for for IN cord-276598-tm0yj2sn 916 4 reduction reduction NN cord-276598-tm0yj2sn 916 5 of of IN cord-276598-tm0yj2sn 916 6 the the DT cord-276598-tm0yj2sn 916 7 nitro nitro NN cord-276598-tm0yj2sn 916 8 - - HYPH cord-276598-tm0yj2sn 916 9 group group NN cord-276598-tm0yj2sn 916 10 route route NN cord-276598-tm0yj2sn 916 11 to to IN cord-276598-tm0yj2sn 916 12 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 916 13 . . . cord-276598-tm0yj2sn 917 1 The the DT cord-276598-tm0yj2sn 917 2 plausible plausible JJ cord-276598-tm0yj2sn 917 3 two two CD cord-276598-tm0yj2sn 917 4 - - HYPH cord-276598-tm0yj2sn 917 5 step step NN cord-276598-tm0yj2sn 917 6 mechanistic mechanistic JJ cord-276598-tm0yj2sn 917 7 process process NN cord-276598-tm0yj2sn 917 8 suggested suggest VBN cord-276598-tm0yj2sn 917 9 by by IN cord-276598-tm0yj2sn 917 10 Hackenberger Hackenberger NNP cord-276598-tm0yj2sn 917 11 's 's POS cord-276598-tm0yj2sn 917 12 group group NN cord-276598-tm0yj2sn 917 13 for for IN cord-276598-tm0yj2sn 917 14 the the DT cord-276598-tm0yj2sn 917 15 synthesis synthesis NN cord-276598-tm0yj2sn 917 16 involves involve VBZ cord-276598-tm0yj2sn 917 17 the the DT cord-276598-tm0yj2sn 917 18 formation formation NN cord-276598-tm0yj2sn 917 19 of of IN cord-276598-tm0yj2sn 917 20 phosphorimidate phosphorimidate NNP cord-276598-tm0yj2sn 917 21 from from IN cord-276598-tm0yj2sn 917 22 the the DT cord-276598-tm0yj2sn 917 23 reduction reduction NN cord-276598-tm0yj2sn 917 24 of of IN cord-276598-tm0yj2sn 917 25 azide azide NN cord-276598-tm0yj2sn 917 26 in in IN cord-276598-tm0yj2sn 917 27 the the DT cord-276598-tm0yj2sn 917 28 presence presence NN cord-276598-tm0yj2sn 917 29 of of IN cord-276598-tm0yj2sn 917 30 ( ( -LRB- cord-276598-tm0yj2sn 917 31 RO)3P RO)3P NNP cord-276598-tm0yj2sn 917 32 ( ( -LRB- cord-276598-tm0yj2sn 917 33 R r NN cord-276598-tm0yj2sn 917 34 = = NN cord-276598-tm0yj2sn 917 35 alkyl alkyl NN cord-276598-tm0yj2sn 917 36 ) ) -RRB- cord-276598-tm0yj2sn 917 37 , , , cord-276598-tm0yj2sn 917 38 eliminating eliminate VBG cord-276598-tm0yj2sn 917 39 N2 N2 NNP cord-276598-tm0yj2sn 917 40 , , , cord-276598-tm0yj2sn 917 41 in in IN cord-276598-tm0yj2sn 917 42 the the DT cord-276598-tm0yj2sn 917 43 first first JJ cord-276598-tm0yj2sn 917 44 step step NN cord-276598-tm0yj2sn 917 45 ( ( -LRB- cord-276598-tm0yj2sn 917 46 Scheme scheme NN cord-276598-tm0yj2sn 917 47 37 37 CD cord-276598-tm0yj2sn 917 48 ) ) -RRB- cord-276598-tm0yj2sn 917 49 [ [ -LRB- cord-276598-tm0yj2sn 917 50 119 119 CD cord-276598-tm0yj2sn 917 51 ] ] -RRB- cord-276598-tm0yj2sn 917 52 . . . cord-276598-tm0yj2sn 918 1 In in IN cord-276598-tm0yj2sn 918 2 the the DT cord-276598-tm0yj2sn 918 3 second second JJ cord-276598-tm0yj2sn 918 4 step step NN cord-276598-tm0yj2sn 918 5 , , , cord-276598-tm0yj2sn 918 6 BF3 BF3 NNP cord-276598-tm0yj2sn 918 7 activates activate VBZ cord-276598-tm0yj2sn 918 8 the the DT cord-276598-tm0yj2sn 918 9 nitrogen nitrogen NN cord-276598-tm0yj2sn 918 10 site site NN cord-276598-tm0yj2sn 918 11 of of IN cord-276598-tm0yj2sn 918 12 the the DT cord-276598-tm0yj2sn 918 13 phosphorimidate phosphorimidate NN cord-276598-tm0yj2sn 918 14 by by IN cord-276598-tm0yj2sn 918 15 forming form VBG cord-276598-tm0yj2sn 918 16 a a DT cord-276598-tm0yj2sn 918 17 coordinated coordinated JJ cord-276598-tm0yj2sn 918 18 complex complex NN cord-276598-tm0yj2sn 918 19 . . . cord-276598-tm0yj2sn 919 1 Electrophilic Electrophilic NNP cord-276598-tm0yj2sn 919 2 attack attack NN cord-276598-tm0yj2sn 919 3 by by IN cord-276598-tm0yj2sn 919 4 a a DT cord-276598-tm0yj2sn 919 5 neighbouring neighbouring JJ cord-276598-tm0yj2sn 919 6 alkyl alkyl NN cord-276598-tm0yj2sn 919 7 group group NN cord-276598-tm0yj2sn 919 8 of of IN cord-276598-tm0yj2sn 919 9 phosphorimidate phosphorimidate NNP cord-276598-tm0yj2sn 919 10 on on IN cord-276598-tm0yj2sn 919 11 the the DT cord-276598-tm0yj2sn 919 12 negatively negatively RB cord-276598-tm0yj2sn 919 13 charged charge VBN cord-276598-tm0yj2sn 919 14 N n CD cord-276598-tm0yj2sn 919 15 atom atom NN cord-276598-tm0yj2sn 919 16 of of IN cord-276598-tm0yj2sn 919 17 the the DT cord-276598-tm0yj2sn 919 18 phosphorimidate phosphorimidate NNP cord-276598-tm0yj2sn 919 19 - - HYPH cord-276598-tm0yj2sn 919 20 BF3 BF3 NNP cord-276598-tm0yj2sn 919 21 complex complex JJ cord-276598-tm0yj2sn 919 22 results result NNS cord-276598-tm0yj2sn 919 23 in in IN cord-276598-tm0yj2sn 919 24 an an DT cord-276598-tm0yj2sn 919 25 ( ( -LRB- cord-276598-tm0yj2sn 919 26 ( ( -LRB- cord-276598-tm0yj2sn 919 27 alkyl)amino)trialkoxyphosphonium alkyl)amino)trialkoxyphosphonium CD cord-276598-tm0yj2sn 919 28 complex complex NN cord-276598-tm0yj2sn 919 29 , , , cord-276598-tm0yj2sn 919 30 cleaving cleave VBG cord-276598-tm0yj2sn 919 31 off off RP cord-276598-tm0yj2sn 919 32 BF3 BF3 NNP cord-276598-tm0yj2sn 919 33 . . . cord-276598-tm0yj2sn 920 1 Nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 920 2 attack attack NN cord-276598-tm0yj2sn 920 3 on on IN cord-276598-tm0yj2sn 920 4 the the DT cord-276598-tm0yj2sn 920 5 trialkoxyphosphonium trialkoxyphosphonium NN cord-276598-tm0yj2sn 920 6 complex complex NN cord-276598-tm0yj2sn 920 7 from from IN cord-276598-tm0yj2sn 920 8 a a DT cord-276598-tm0yj2sn 920 9 neighboring neighbor VBG cord-276598-tm0yj2sn 920 10 phosphorimidate phosphorimidate NN cord-276598-tm0yj2sn 920 11 completes complete VBZ cord-276598-tm0yj2sn 920 12 the the DT cord-276598-tm0yj2sn 920 13 catalytic catalytic JJ cord-276598-tm0yj2sn 920 14 cycle cycle NN cord-276598-tm0yj2sn 920 15 , , , cord-276598-tm0yj2sn 920 16 affording afford VBG cord-276598-tm0yj2sn 920 17 a a DT cord-276598-tm0yj2sn 920 18 P p NN cord-276598-tm0yj2sn 920 19 = = SYM cord-276598-tm0yj2sn 920 20 O o NN cord-276598-tm0yj2sn 920 21 bond bond NN cord-276598-tm0yj2sn 920 22 of of IN cord-276598-tm0yj2sn 920 23 the the DT cord-276598-tm0yj2sn 920 24 desired desire VBN cord-276598-tm0yj2sn 920 25 P P NNP cord-276598-tm0yj2sn 920 26 - - HYPH cord-276598-tm0yj2sn 920 27 N n CD cord-276598-tm0yj2sn 920 28 product product NN cord-276598-tm0yj2sn 920 29 . . . cord-276598-tm0yj2sn 921 1 Scheme scheme NN cord-276598-tm0yj2sn 921 2 36 36 CD cord-276598-tm0yj2sn 921 3 . . . cord-276598-tm0yj2sn 922 1 Proposed propose VBN cord-276598-tm0yj2sn 922 2 mechanism mechanism NN cord-276598-tm0yj2sn 922 3 for for IN cord-276598-tm0yj2sn 922 4 reduction reduction NN cord-276598-tm0yj2sn 922 5 of of IN cord-276598-tm0yj2sn 922 6 the the DT cord-276598-tm0yj2sn 922 7 nitro nitro NN cord-276598-tm0yj2sn 922 8 - - HYPH cord-276598-tm0yj2sn 922 9 group group NN cord-276598-tm0yj2sn 922 10 route route NN cord-276598-tm0yj2sn 922 11 to to IN cord-276598-tm0yj2sn 922 12 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 922 13 . . . cord-276598-tm0yj2sn 923 1 The the DT cord-276598-tm0yj2sn 923 2 plausible plausible JJ cord-276598-tm0yj2sn 923 3 two two CD cord-276598-tm0yj2sn 923 4 - - HYPH cord-276598-tm0yj2sn 923 5 step step NN cord-276598-tm0yj2sn 923 6 mechanistic mechanistic JJ cord-276598-tm0yj2sn 923 7 process process NN cord-276598-tm0yj2sn 923 8 suggested suggest VBN cord-276598-tm0yj2sn 923 9 by by IN cord-276598-tm0yj2sn 923 10 Hackenberger Hackenberger NNP cord-276598-tm0yj2sn 923 11 's 's POS cord-276598-tm0yj2sn 923 12 group group NN cord-276598-tm0yj2sn 923 13 for for IN cord-276598-tm0yj2sn 923 14 the the DT cord-276598-tm0yj2sn 923 15 synthesis synthesis NN cord-276598-tm0yj2sn 923 16 involves involve VBZ cord-276598-tm0yj2sn 923 17 the the DT cord-276598-tm0yj2sn 923 18 formation formation NN cord-276598-tm0yj2sn 923 19 of of IN cord-276598-tm0yj2sn 923 20 phosphorimidate phosphorimidate NNP cord-276598-tm0yj2sn 923 21 from from IN cord-276598-tm0yj2sn 923 22 the the DT cord-276598-tm0yj2sn 923 23 reduction reduction NN cord-276598-tm0yj2sn 923 24 of of IN cord-276598-tm0yj2sn 923 25 azide azide NN cord-276598-tm0yj2sn 923 26 in in IN cord-276598-tm0yj2sn 923 27 the the DT cord-276598-tm0yj2sn 923 28 presence presence NN cord-276598-tm0yj2sn 923 29 of of IN cord-276598-tm0yj2sn 923 30 ( ( -LRB- cord-276598-tm0yj2sn 923 31 RO ro NN cord-276598-tm0yj2sn 923 32 ) ) -RRB- cord-276598-tm0yj2sn 923 33 3 3 CD cord-276598-tm0yj2sn 923 34 P p NN cord-276598-tm0yj2sn 923 35 ( ( -LRB- cord-276598-tm0yj2sn 923 36 R r NN cord-276598-tm0yj2sn 923 37 = = NN cord-276598-tm0yj2sn 923 38 alkyl alkyl NN cord-276598-tm0yj2sn 923 39 ) ) -RRB- cord-276598-tm0yj2sn 923 40 , , , cord-276598-tm0yj2sn 923 41 eliminating eliminate VBG cord-276598-tm0yj2sn 923 42 N n CD cord-276598-tm0yj2sn 923 43 2 2 CD cord-276598-tm0yj2sn 923 44 , , , cord-276598-tm0yj2sn 923 45 in in IN cord-276598-tm0yj2sn 923 46 the the DT cord-276598-tm0yj2sn 923 47 first first JJ cord-276598-tm0yj2sn 923 48 step step NN cord-276598-tm0yj2sn 923 49 ( ( -LRB- cord-276598-tm0yj2sn 923 50 Scheme scheme NN cord-276598-tm0yj2sn 923 51 37 37 CD cord-276598-tm0yj2sn 923 52 ) ) -RRB- cord-276598-tm0yj2sn 923 53 [ [ -LRB- cord-276598-tm0yj2sn 923 54 119 119 CD cord-276598-tm0yj2sn 923 55 ] ] -RRB- cord-276598-tm0yj2sn 923 56 . . . cord-276598-tm0yj2sn 924 1 In in IN cord-276598-tm0yj2sn 924 2 the the DT cord-276598-tm0yj2sn 924 3 second second JJ cord-276598-tm0yj2sn 924 4 step step NN cord-276598-tm0yj2sn 924 5 , , , cord-276598-tm0yj2sn 924 6 BF BF NNP cord-276598-tm0yj2sn 924 7 3 3 CD cord-276598-tm0yj2sn 924 8 activates activate VBZ cord-276598-tm0yj2sn 924 9 the the DT cord-276598-tm0yj2sn 924 10 nitrogen nitrogen NN cord-276598-tm0yj2sn 924 11 site site NN cord-276598-tm0yj2sn 924 12 of of IN cord-276598-tm0yj2sn 924 13 the the DT cord-276598-tm0yj2sn 924 14 phosphorimidate phosphorimidate NN cord-276598-tm0yj2sn 924 15 by by IN cord-276598-tm0yj2sn 924 16 forming form VBG cord-276598-tm0yj2sn 924 17 a a DT cord-276598-tm0yj2sn 924 18 coordinated coordinated JJ cord-276598-tm0yj2sn 924 19 complex complex NN cord-276598-tm0yj2sn 924 20 . . . cord-276598-tm0yj2sn 925 1 Electrophilic Electrophilic NNP cord-276598-tm0yj2sn 925 2 attack attack NN cord-276598-tm0yj2sn 925 3 by by IN cord-276598-tm0yj2sn 925 4 a a DT cord-276598-tm0yj2sn 925 5 neighbouring neighbouring JJ cord-276598-tm0yj2sn 925 6 alkyl alkyl NN cord-276598-tm0yj2sn 925 7 group group NN cord-276598-tm0yj2sn 925 8 of of IN cord-276598-tm0yj2sn 925 9 phosphorimidate phosphorimidate NNP cord-276598-tm0yj2sn 925 10 on on IN cord-276598-tm0yj2sn 925 11 the the DT cord-276598-tm0yj2sn 925 12 negatively negatively RB cord-276598-tm0yj2sn 925 13 charged charge VBN cord-276598-tm0yj2sn 925 14 N n CD cord-276598-tm0yj2sn 925 15 atom atom NN cord-276598-tm0yj2sn 925 16 of of IN cord-276598-tm0yj2sn 925 17 the the DT cord-276598-tm0yj2sn 925 18 phosphorimidate phosphorimidate NN cord-276598-tm0yj2sn 925 19 - - HYPH cord-276598-tm0yj2sn 925 20 BF BF NNP cord-276598-tm0yj2sn 925 21 3 3 CD cord-276598-tm0yj2sn 925 22 complex complex JJ cord-276598-tm0yj2sn 925 23 results result NNS cord-276598-tm0yj2sn 925 24 in in IN cord-276598-tm0yj2sn 925 25 an an DT cord-276598-tm0yj2sn 925 26 ( ( -LRB- cord-276598-tm0yj2sn 925 27 ( ( -LRB- cord-276598-tm0yj2sn 925 28 alkyl)amino)trialkoxyphosphonium alkyl)amino)trialkoxyphosphonium CD cord-276598-tm0yj2sn 925 29 complex complex NN cord-276598-tm0yj2sn 925 30 , , , cord-276598-tm0yj2sn 925 31 cleaving cleave VBG cord-276598-tm0yj2sn 925 32 off off RP cord-276598-tm0yj2sn 925 33 BF BF NNP cord-276598-tm0yj2sn 925 34 3 3 CD cord-276598-tm0yj2sn 925 35 . . . cord-276598-tm0yj2sn 926 1 Nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 926 2 attack attack NN cord-276598-tm0yj2sn 926 3 on on IN cord-276598-tm0yj2sn 926 4 the the DT cord-276598-tm0yj2sn 926 5 trialkoxyphosphonium trialkoxyphosphonium NN cord-276598-tm0yj2sn 926 6 complex complex NN cord-276598-tm0yj2sn 926 7 from from IN cord-276598-tm0yj2sn 926 8 a a DT cord-276598-tm0yj2sn 926 9 neighboring neighbor VBG cord-276598-tm0yj2sn 926 10 phosphorimidate phosphorimidate NN cord-276598-tm0yj2sn 926 11 completes complete VBZ cord-276598-tm0yj2sn 926 12 the the DT cord-276598-tm0yj2sn 926 13 catalytic catalytic JJ cord-276598-tm0yj2sn 926 14 cycle cycle NN cord-276598-tm0yj2sn 926 15 , , , cord-276598-tm0yj2sn 926 16 affording afford VBG cord-276598-tm0yj2sn 926 17 a a DT cord-276598-tm0yj2sn 926 18 P p NN cord-276598-tm0yj2sn 926 19 = = SYM cord-276598-tm0yj2sn 926 20 O o NN cord-276598-tm0yj2sn 926 21 bond bond NN cord-276598-tm0yj2sn 926 22 of of IN cord-276598-tm0yj2sn 926 23 the the DT cord-276598-tm0yj2sn 926 24 desired desire VBN cord-276598-tm0yj2sn 926 25 P P NNP cord-276598-tm0yj2sn 926 26 - - HYPH cord-276598-tm0yj2sn 926 27 N n CD cord-276598-tm0yj2sn 926 28 product product NN cord-276598-tm0yj2sn 926 29 . . . cord-276598-tm0yj2sn 927 1 Molecules molecule NNS cord-276598-tm0yj2sn 927 2 2020 2020 CD cord-276598-tm0yj2sn 927 3 , , , cord-276598-tm0yj2sn 927 4 25 25 CD cord-276598-tm0yj2sn 927 5 , , , cord-276598-tm0yj2sn 927 6 x x NN cord-276598-tm0yj2sn 927 7 FOR for IN cord-276598-tm0yj2sn 927 8 PEER PEER NNP cord-276598-tm0yj2sn 927 9 REVIEW REVIEW NNP cord-276598-tm0yj2sn 927 10 29 29 CD cord-276598-tm0yj2sn 927 11 of of IN cord-276598-tm0yj2sn 927 12 37 37 CD cord-276598-tm0yj2sn 927 13 Scheme Scheme NNP cord-276598-tm0yj2sn 927 14 37 37 CD cord-276598-tm0yj2sn 927 15 . . . cord-276598-tm0yj2sn 928 1 Proposed propose VBN cord-276598-tm0yj2sn 928 2 mechanism mechanism NN cord-276598-tm0yj2sn 928 3 for for IN cord-276598-tm0yj2sn 928 4 the the DT cord-276598-tm0yj2sn 928 5 catalyst catalyst NN cord-276598-tm0yj2sn 928 6 - - HYPH cord-276598-tm0yj2sn 928 7 free free JJ cord-276598-tm0yj2sn 928 8 Staudinger Staudinger NNP cord-276598-tm0yj2sn 928 9 reduction reduction NN cord-276598-tm0yj2sn 928 10 and and CC cord-276598-tm0yj2sn 928 11 Lewis Lewis NNP cord-276598-tm0yj2sn 928 12 - - HYPH cord-276598-tm0yj2sn 928 13 acid acid NN cord-276598-tm0yj2sn 928 14 catalyzed catalyze VBN cord-276598-tm0yj2sn 928 15 rearrangement rearrangement NN cord-276598-tm0yj2sn 928 16 route route NN cord-276598-tm0yj2sn 928 17 to to IN cord-276598-tm0yj2sn 928 18 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 928 19 . . . cord-276598-tm0yj2sn 929 1 For for IN cord-276598-tm0yj2sn 929 2 the the DT cord-276598-tm0yj2sn 929 3 hydrophosphinylation hydrophosphinylation NN cord-276598-tm0yj2sn 929 4 route route NN cord-276598-tm0yj2sn 929 5 to to IN cord-276598-tm0yj2sn 929 6 P P NNP cord-276598-tm0yj2sn 929 7 - - HYPH cord-276598-tm0yj2sn 929 8 Ns Ns NNP cord-276598-tm0yj2sn 929 9 , , , cord-276598-tm0yj2sn 929 10 Zimin Zimin NNP cord-276598-tm0yj2sn 929 11 et et NNP cord-276598-tm0yj2sn 929 12 al al NNP cord-276598-tm0yj2sn 929 13 . . NNP cord-276598-tm0yj2sn 929 14 proposed propose VBD cord-276598-tm0yj2sn 929 15 that that IN cord-276598-tm0yj2sn 929 16 in in IN cord-276598-tm0yj2sn 929 17 the the DT cord-276598-tm0yj2sn 929 18 first first JJ cord-276598-tm0yj2sn 929 19 step step NN cord-276598-tm0yj2sn 929 20 , , , cord-276598-tm0yj2sn 929 21 sodium sodium NNP cord-276598-tm0yj2sn 929 22 dialkyl dialkyl NNP cord-276598-tm0yj2sn 929 23 phosphite phosphite NNP cord-276598-tm0yj2sn 929 24 ( ( -LRB- cord-276598-tm0yj2sn 929 25 ( ( -LRB- cord-276598-tm0yj2sn 929 26 RO)2PONa RO)2PONa NNP cord-276598-tm0yj2sn 929 27 , , , cord-276598-tm0yj2sn 929 28 R r NN cord-276598-tm0yj2sn 929 29 = = FW cord-276598-tm0yj2sn 929 30 Et Et NNP cord-276598-tm0yj2sn 929 31 , , , cord-276598-tm0yj2sn 929 32 Ph Ph NNP cord-276598-tm0yj2sn 929 33 ) ) -RRB- cord-276598-tm0yj2sn 929 34 reacts react VBZ cord-276598-tm0yj2sn 929 35 with with IN cord-276598-tm0yj2sn 929 36 alkyl alkyl JJ cord-276598-tm0yj2sn 929 37 nitrile nitrile NN cord-276598-tm0yj2sn 929 38 to to TO cord-276598-tm0yj2sn 929 39 form form VB cord-276598-tm0yj2sn 929 40 an an DT cord-276598-tm0yj2sn 929 41 imine imine NN cord-276598-tm0yj2sn 929 42 ( ( -LRB- cord-276598-tm0yj2sn 929 43 C c NN cord-276598-tm0yj2sn 929 44 = = SYM cord-276598-tm0yj2sn 929 45 N N NNP cord-276598-tm0yj2sn 929 46 ) ) -RRB- cord-276598-tm0yj2sn 929 47 , , , cord-276598-tm0yj2sn 929 48 which which WDT cord-276598-tm0yj2sn 929 49 reacts react VBZ cord-276598-tm0yj2sn 929 50 further further RB cord-276598-tm0yj2sn 929 51 with with IN cord-276598-tm0yj2sn 929 52 a a DT cord-276598-tm0yj2sn 929 53 second second JJ cord-276598-tm0yj2sn 929 54 equivalent equivalent NN cord-276598-tm0yj2sn 929 55 of of IN cord-276598-tm0yj2sn 929 56 ( ( -LRB- cord-276598-tm0yj2sn 929 57 RO)2PONa ro)2pona NN cord-276598-tm0yj2sn 929 58 to to TO cord-276598-tm0yj2sn 929 59 form form VB cord-276598-tm0yj2sn 929 60 the the DT cord-276598-tm0yj2sn 929 61 1,1-addition 1,1-addition CD cord-276598-tm0yj2sn 929 62 product product NN cord-276598-tm0yj2sn 929 63 , , , cord-276598-tm0yj2sn 929 64 sodium sodium NN cord-276598-tm0yj2sn 929 65 ( ( -LRB- cord-276598-tm0yj2sn 929 66 1,1-bis(dialkoxyphosphoryl)alkyl)amide 1,1-bis(dialkoxyphosphoryl)alkyl)amide NNP cord-276598-tm0yj2sn 929 67 ( ( -LRB- cord-276598-tm0yj2sn 929 68 Scheme scheme NN cord-276598-tm0yj2sn 929 69 38 38 CD cord-276598-tm0yj2sn 929 70 ) ) -RRB- cord-276598-tm0yj2sn 929 71 [ [ -LRB- cord-276598-tm0yj2sn 929 72 120 120 CD cord-276598-tm0yj2sn 929 73 ] ] -RRB- cord-276598-tm0yj2sn 929 74 . . . cord-276598-tm0yj2sn 930 1 In in IN cord-276598-tm0yj2sn 930 2 the the DT cord-276598-tm0yj2sn 930 3 second second JJ cord-276598-tm0yj2sn 930 4 step step NN cord-276598-tm0yj2sn 930 5 , , , cord-276598-tm0yj2sn 930 6 sodium sodium NN cord-276598-tm0yj2sn 930 7 ( ( -LRB- cord-276598-tm0yj2sn 930 8 1,1-bis(dialkyoxyphosphoryl)alkyl)amide 1,1-bis(dialkyoxyphosphoryl)alkyl)amide NNP cord-276598-tm0yj2sn 930 9 undergoes undergo VBZ cord-276598-tm0yj2sn 930 10 hydrolysis hydrolysis NN cord-276598-tm0yj2sn 930 11 and and CC cord-276598-tm0yj2sn 930 12 isomerization isomerization NN cord-276598-tm0yj2sn 930 13 to to TO cord-276598-tm0yj2sn 930 14 give give VB cord-276598-tm0yj2sn 930 15 the the DT cord-276598-tm0yj2sn 930 16 1,2-addition 1,2-addition CD cord-276598-tm0yj2sn 930 17 phosphoramidate phosphoramidate NN cord-276598-tm0yj2sn 930 18 product product NN cord-276598-tm0yj2sn 930 19 containing contain VBG cord-276598-tm0yj2sn 930 20 a a DT cord-276598-tm0yj2sn 930 21 P p NN cord-276598-tm0yj2sn 930 22 - - HYPH cord-276598-tm0yj2sn 930 23 C C NNP cord-276598-tm0yj2sn 930 24 - - HYPH cord-276598-tm0yj2sn 930 25 N N NNP cord-276598-tm0yj2sn 930 26 - - HYPH cord-276598-tm0yj2sn 930 27 P p NN cord-276598-tm0yj2sn 930 28 bond bond NN cord-276598-tm0yj2sn 930 29 , , , cord-276598-tm0yj2sn 930 30 eliminating eliminate VBG cord-276598-tm0yj2sn 930 31 a a DT cord-276598-tm0yj2sn 930 32 sodium sodium NN cord-276598-tm0yj2sn 930 33 cation cation NN cord-276598-tm0yj2sn 930 34 in in IN cord-276598-tm0yj2sn 930 35 the the DT cord-276598-tm0yj2sn 930 36 process process NN cord-276598-tm0yj2sn 930 37 . . . cord-276598-tm0yj2sn 931 1 Scheme scheme NN cord-276598-tm0yj2sn 931 2 37 37 CD cord-276598-tm0yj2sn 931 3 . . . cord-276598-tm0yj2sn 932 1 Proposed propose VBN cord-276598-tm0yj2sn 932 2 mechanism mechanism NN cord-276598-tm0yj2sn 932 3 for for IN cord-276598-tm0yj2sn 932 4 the the DT cord-276598-tm0yj2sn 932 5 catalyst catalyst NN cord-276598-tm0yj2sn 932 6 - - HYPH cord-276598-tm0yj2sn 932 7 free free JJ cord-276598-tm0yj2sn 932 8 Staudinger Staudinger NNP cord-276598-tm0yj2sn 932 9 reduction reduction NN cord-276598-tm0yj2sn 932 10 and and CC cord-276598-tm0yj2sn 932 11 Lewis Lewis NNP cord-276598-tm0yj2sn 932 12 - - HYPH cord-276598-tm0yj2sn 932 13 acid acid NN cord-276598-tm0yj2sn 932 14 catalyzed catalyze VBN cord-276598-tm0yj2sn 932 15 rearrangement rearrangement NN cord-276598-tm0yj2sn 932 16 route route NN cord-276598-tm0yj2sn 932 17 to to IN cord-276598-tm0yj2sn 932 18 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 932 19 . . . cord-276598-tm0yj2sn 933 1 For for IN cord-276598-tm0yj2sn 933 2 the the DT cord-276598-tm0yj2sn 933 3 hydrophosphinylation hydrophosphinylation NN cord-276598-tm0yj2sn 933 4 route route NN cord-276598-tm0yj2sn 933 5 to to IN cord-276598-tm0yj2sn 933 6 P P NNP cord-276598-tm0yj2sn 933 7 - - HYPH cord-276598-tm0yj2sn 933 8 Ns Ns NNP cord-276598-tm0yj2sn 933 9 , , , cord-276598-tm0yj2sn 933 10 Zimin Zimin NNP cord-276598-tm0yj2sn 933 11 et et NNP cord-276598-tm0yj2sn 933 12 al al NNP cord-276598-tm0yj2sn 933 13 . . NNP cord-276598-tm0yj2sn 933 14 proposed propose VBD cord-276598-tm0yj2sn 933 15 that that IN cord-276598-tm0yj2sn 933 16 in in IN cord-276598-tm0yj2sn 933 17 the the DT cord-276598-tm0yj2sn 933 18 first first JJ cord-276598-tm0yj2sn 933 19 step step NN cord-276598-tm0yj2sn 933 20 , , , cord-276598-tm0yj2sn 933 21 sodium sodium NNP cord-276598-tm0yj2sn 933 22 dialkyl dialkyl NNP cord-276598-tm0yj2sn 933 23 phosphite phosphite NNP cord-276598-tm0yj2sn 933 24 ( ( -LRB- cord-276598-tm0yj2sn 933 25 ( ( -LRB- cord-276598-tm0yj2sn 933 26 RO RO NNP cord-276598-tm0yj2sn 933 27 ) ) -RRB- cord-276598-tm0yj2sn 933 28 2 2 CD cord-276598-tm0yj2sn 933 29 PONa PONa NNS cord-276598-tm0yj2sn 933 30 , , , cord-276598-tm0yj2sn 933 31 R r NN cord-276598-tm0yj2sn 933 32 = = NN cord-276598-tm0yj2sn 933 33 Et Et NNP cord-276598-tm0yj2sn 933 34 , , , cord-276598-tm0yj2sn 933 35 Ph Ph NNP cord-276598-tm0yj2sn 933 36 ) ) -RRB- cord-276598-tm0yj2sn 933 37 reacts react VBZ cord-276598-tm0yj2sn 933 38 with with IN cord-276598-tm0yj2sn 933 39 alkyl alkyl JJ cord-276598-tm0yj2sn 933 40 nitrile nitrile NN cord-276598-tm0yj2sn 933 41 to to TO cord-276598-tm0yj2sn 933 42 form form VB cord-276598-tm0yj2sn 933 43 an an DT cord-276598-tm0yj2sn 933 44 imine imine NN cord-276598-tm0yj2sn 933 45 ( ( -LRB- cord-276598-tm0yj2sn 933 46 C c NN cord-276598-tm0yj2sn 933 47 = = SYM cord-276598-tm0yj2sn 933 48 N N NNP cord-276598-tm0yj2sn 933 49 ) ) -RRB- cord-276598-tm0yj2sn 933 50 , , , cord-276598-tm0yj2sn 933 51 which which WDT cord-276598-tm0yj2sn 933 52 reacts react VBZ cord-276598-tm0yj2sn 933 53 further further RB cord-276598-tm0yj2sn 933 54 with with IN cord-276598-tm0yj2sn 933 55 a a DT cord-276598-tm0yj2sn 933 56 second second JJ cord-276598-tm0yj2sn 933 57 equivalent equivalent NN cord-276598-tm0yj2sn 933 58 of of IN cord-276598-tm0yj2sn 933 59 ( ( -LRB- cord-276598-tm0yj2sn 933 60 RO RO NNP cord-276598-tm0yj2sn 933 61 ) ) -RRB- cord-276598-tm0yj2sn 933 62 2 2 CD cord-276598-tm0yj2sn 933 63 PONa PONa NNS cord-276598-tm0yj2sn 933 64 to to TO cord-276598-tm0yj2sn 933 65 form form VB cord-276598-tm0yj2sn 933 66 the the DT cord-276598-tm0yj2sn 933 67 1,1-addition 1,1-addition CD cord-276598-tm0yj2sn 933 68 product product NN cord-276598-tm0yj2sn 933 69 , , , cord-276598-tm0yj2sn 933 70 sodium sodium NN cord-276598-tm0yj2sn 933 71 ( ( -LRB- cord-276598-tm0yj2sn 933 72 1,1-bis(dialkoxyphosphoryl)alkyl)amide 1,1-bis(dialkoxyphosphoryl)alkyl)amide NNP cord-276598-tm0yj2sn 933 73 ( ( -LRB- cord-276598-tm0yj2sn 933 74 Scheme scheme NN cord-276598-tm0yj2sn 933 75 38 38 CD cord-276598-tm0yj2sn 933 76 ) ) -RRB- cord-276598-tm0yj2sn 933 77 [ [ -LRB- cord-276598-tm0yj2sn 933 78 120 120 CD cord-276598-tm0yj2sn 933 79 ] ] -RRB- cord-276598-tm0yj2sn 933 80 . . . cord-276598-tm0yj2sn 934 1 In in IN cord-276598-tm0yj2sn 934 2 the the DT cord-276598-tm0yj2sn 934 3 second second JJ cord-276598-tm0yj2sn 934 4 step step NN cord-276598-tm0yj2sn 934 5 , , , cord-276598-tm0yj2sn 934 6 sodium sodium NN cord-276598-tm0yj2sn 934 7 ( ( -LRB- cord-276598-tm0yj2sn 934 8 1,1-bis(dialkyoxyphosphoryl)alkyl)amide 1,1-bis(dialkyoxyphosphoryl)alkyl)amide NNP cord-276598-tm0yj2sn 934 9 undergoes undergo VBZ cord-276598-tm0yj2sn 934 10 hydrolysis hydrolysis NN cord-276598-tm0yj2sn 934 11 and and CC cord-276598-tm0yj2sn 934 12 isomerization isomerization NN cord-276598-tm0yj2sn 934 13 to to TO cord-276598-tm0yj2sn 934 14 give give VB cord-276598-tm0yj2sn 934 15 the the DT cord-276598-tm0yj2sn 934 16 1,2-addition 1,2-addition CD cord-276598-tm0yj2sn 934 17 phosphoramidate phosphoramidate NN cord-276598-tm0yj2sn 934 18 product product NN cord-276598-tm0yj2sn 934 19 containing contain VBG cord-276598-tm0yj2sn 934 20 a a DT cord-276598-tm0yj2sn 934 21 P p NN cord-276598-tm0yj2sn 934 22 - - HYPH cord-276598-tm0yj2sn 934 23 C C NNP cord-276598-tm0yj2sn 934 24 - - HYPH cord-276598-tm0yj2sn 934 25 N N NNP cord-276598-tm0yj2sn 934 26 - - HYPH cord-276598-tm0yj2sn 934 27 P p NN cord-276598-tm0yj2sn 934 28 bond bond NN cord-276598-tm0yj2sn 934 29 , , , cord-276598-tm0yj2sn 934 30 eliminating eliminate VBG cord-276598-tm0yj2sn 934 31 a a DT cord-276598-tm0yj2sn 934 32 sodium sodium NN cord-276598-tm0yj2sn 934 33 cation cation NN cord-276598-tm0yj2sn 934 34 in in IN cord-276598-tm0yj2sn 934 35 the the DT cord-276598-tm0yj2sn 934 36 process process NN cord-276598-tm0yj2sn 934 37 . . . cord-276598-tm0yj2sn 935 1 For for IN cord-276598-tm0yj2sn 935 2 the the DT cord-276598-tm0yj2sn 935 3 hydrophosphinylation hydrophosphinylation NN cord-276598-tm0yj2sn 935 4 route route NN cord-276598-tm0yj2sn 935 5 to to IN cord-276598-tm0yj2sn 935 6 P P NNP cord-276598-tm0yj2sn 935 7 - - HYPH cord-276598-tm0yj2sn 935 8 Ns Ns NNP cord-276598-tm0yj2sn 935 9 , , , cord-276598-tm0yj2sn 935 10 Zimin Zimin NNP cord-276598-tm0yj2sn 935 11 et et NNP cord-276598-tm0yj2sn 935 12 al al NNP cord-276598-tm0yj2sn 935 13 . . NNP cord-276598-tm0yj2sn 935 14 proposed propose VBD cord-276598-tm0yj2sn 935 15 that that IN cord-276598-tm0yj2sn 935 16 in in IN cord-276598-tm0yj2sn 935 17 the the DT cord-276598-tm0yj2sn 935 18 first first JJ cord-276598-tm0yj2sn 935 19 step step NN cord-276598-tm0yj2sn 935 20 , , , cord-276598-tm0yj2sn 935 21 sodium sodium NNP cord-276598-tm0yj2sn 935 22 dialkyl dialkyl NNP cord-276598-tm0yj2sn 935 23 phosphite phosphite NNP cord-276598-tm0yj2sn 935 24 ( ( -LRB- cord-276598-tm0yj2sn 935 25 ( ( -LRB- cord-276598-tm0yj2sn 935 26 RO)2PONa RO)2PONa NNP cord-276598-tm0yj2sn 935 27 , , , cord-276598-tm0yj2sn 935 28 R r NN cord-276598-tm0yj2sn 935 29 = = FW cord-276598-tm0yj2sn 935 30 Et Et NNP cord-276598-tm0yj2sn 935 31 , , , cord-276598-tm0yj2sn 935 32 Ph Ph NNP cord-276598-tm0yj2sn 935 33 ) ) -RRB- cord-276598-tm0yj2sn 935 34 reacts react VBZ cord-276598-tm0yj2sn 935 35 with with IN cord-276598-tm0yj2sn 935 36 alkyl alkyl JJ cord-276598-tm0yj2sn 935 37 nitrile nitrile NN cord-276598-tm0yj2sn 935 38 to to TO cord-276598-tm0yj2sn 935 39 form form VB cord-276598-tm0yj2sn 935 40 an an DT cord-276598-tm0yj2sn 935 41 imine imine NN cord-276598-tm0yj2sn 935 42 ( ( -LRB- cord-276598-tm0yj2sn 935 43 C c NN cord-276598-tm0yj2sn 935 44 = = SYM cord-276598-tm0yj2sn 935 45 N N NNP cord-276598-tm0yj2sn 935 46 ) ) -RRB- cord-276598-tm0yj2sn 935 47 , , , cord-276598-tm0yj2sn 935 48 which which WDT cord-276598-tm0yj2sn 935 49 reacts react VBZ cord-276598-tm0yj2sn 935 50 further further RB cord-276598-tm0yj2sn 935 51 with with IN cord-276598-tm0yj2sn 935 52 a a DT cord-276598-tm0yj2sn 935 53 second second JJ cord-276598-tm0yj2sn 935 54 equivalent equivalent NN cord-276598-tm0yj2sn 935 55 of of IN cord-276598-tm0yj2sn 935 56 ( ( -LRB- cord-276598-tm0yj2sn 935 57 RO)2PONa ro)2pona NN cord-276598-tm0yj2sn 935 58 to to TO cord-276598-tm0yj2sn 935 59 form form VB cord-276598-tm0yj2sn 935 60 the the DT cord-276598-tm0yj2sn 935 61 1,1-addition 1,1-addition CD cord-276598-tm0yj2sn 935 62 product product NN cord-276598-tm0yj2sn 935 63 , , , cord-276598-tm0yj2sn 935 64 sodium sodium NN cord-276598-tm0yj2sn 935 65 ( ( -LRB- cord-276598-tm0yj2sn 935 66 1,1-bis(dialkoxyphosphoryl)alkyl)amide 1,1-bis(dialkoxyphosphoryl)alkyl)amide NNP cord-276598-tm0yj2sn 935 67 ( ( -LRB- cord-276598-tm0yj2sn 935 68 Scheme scheme NN cord-276598-tm0yj2sn 935 69 38 38 CD cord-276598-tm0yj2sn 935 70 ) ) -RRB- cord-276598-tm0yj2sn 935 71 [ [ -LRB- cord-276598-tm0yj2sn 935 72 120 120 CD cord-276598-tm0yj2sn 935 73 ] ] -RRB- cord-276598-tm0yj2sn 935 74 . . . cord-276598-tm0yj2sn 936 1 In in IN cord-276598-tm0yj2sn 936 2 the the DT cord-276598-tm0yj2sn 936 3 second second JJ cord-276598-tm0yj2sn 936 4 step step NN cord-276598-tm0yj2sn 936 5 , , , cord-276598-tm0yj2sn 936 6 sodium sodium NN cord-276598-tm0yj2sn 936 7 ( ( -LRB- cord-276598-tm0yj2sn 936 8 1,1-bis(dialkyoxyphosphoryl)alkyl)amide 1,1-bis(dialkyoxyphosphoryl)alkyl)amide NNP cord-276598-tm0yj2sn 936 9 undergoes undergo VBZ cord-276598-tm0yj2sn 936 10 hydrolysis hydrolysis NN cord-276598-tm0yj2sn 936 11 and and CC cord-276598-tm0yj2sn 936 12 isomerization isomerization NN cord-276598-tm0yj2sn 936 13 to to TO cord-276598-tm0yj2sn 936 14 give give VB cord-276598-tm0yj2sn 936 15 the the DT cord-276598-tm0yj2sn 936 16 1,2-addition 1,2-addition CD cord-276598-tm0yj2sn 936 17 phosphoramidate phosphoramidate NN cord-276598-tm0yj2sn 936 18 product product NN cord-276598-tm0yj2sn 936 19 containing contain VBG cord-276598-tm0yj2sn 936 20 a a DT cord-276598-tm0yj2sn 936 21 P p NN cord-276598-tm0yj2sn 936 22 - - HYPH cord-276598-tm0yj2sn 936 23 C C NNP cord-276598-tm0yj2sn 936 24 - - HYPH cord-276598-tm0yj2sn 936 25 N N NNP cord-276598-tm0yj2sn 936 26 - - HYPH cord-276598-tm0yj2sn 936 27 P p NN cord-276598-tm0yj2sn 936 28 bond bond NN cord-276598-tm0yj2sn 936 29 , , , cord-276598-tm0yj2sn 936 30 eliminating eliminate VBG cord-276598-tm0yj2sn 936 31 a a DT cord-276598-tm0yj2sn 936 32 sodium sodium NN cord-276598-tm0yj2sn 936 33 cation cation NN cord-276598-tm0yj2sn 936 34 in in IN cord-276598-tm0yj2sn 936 35 the the DT cord-276598-tm0yj2sn 936 36 process process NN cord-276598-tm0yj2sn 936 37 . . . cord-276598-tm0yj2sn 937 1 Scheme scheme NN cord-276598-tm0yj2sn 937 2 38 38 CD cord-276598-tm0yj2sn 937 3 . . . cord-276598-tm0yj2sn 938 1 Proposed propose VBN cord-276598-tm0yj2sn 938 2 mechanism mechanism NN cord-276598-tm0yj2sn 938 3 for for IN cord-276598-tm0yj2sn 938 4 hydrophosphinylation hydrophosphinylation NNP cord-276598-tm0yj2sn 938 5 route route NN cord-276598-tm0yj2sn 938 6 to to IN cord-276598-tm0yj2sn 938 7 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 938 8 . . . cord-276598-tm0yj2sn 939 1 Chabour Chabour NNP cord-276598-tm0yj2sn 939 2 et et FW cord-276598-tm0yj2sn 939 3 al al NNP cord-276598-tm0yj2sn 939 4 . . . cord-276598-tm0yj2sn 940 1 proposed propose VBD cord-276598-tm0yj2sn 940 2 a a DT cord-276598-tm0yj2sn 940 3 mechanism mechanism NN cord-276598-tm0yj2sn 940 4 of of IN cord-276598-tm0yj2sn 940 5 the the DT cord-276598-tm0yj2sn 940 6 reaction reaction NN cord-276598-tm0yj2sn 940 7 in in IN cord-276598-tm0yj2sn 940 8 which which WDT cord-276598-tm0yj2sn 940 9 ( ( -LRB- cord-276598-tm0yj2sn 940 10 EtO)2P(O)NH2 eto)2p(o)nh2 RB cord-276598-tm0yj2sn 940 11 reacts react VBZ cord-276598-tm0yj2sn 940 12 with with IN cord-276598-tm0yj2sn 940 13 ( ( -LRB- cord-276598-tm0yj2sn 940 14 or or CC cord-276598-tm0yj2sn 940 15 is be VBZ cord-276598-tm0yj2sn 940 16 activated activate VBN cord-276598-tm0yj2sn 940 17 by by IN cord-276598-tm0yj2sn 940 18 ) ) -RRB- cord-276598-tm0yj2sn 941 1 acetic acetic JJ cord-276598-tm0yj2sn 941 2 anhydride anhydride NN cord-276598-tm0yj2sn 941 3 to to TO cord-276598-tm0yj2sn 941 4 form form VB cord-276598-tm0yj2sn 941 5 diethyl diethyl JJ cord-276598-tm0yj2sn 941 6 acetylphosphoramidate acetylphosphoramidate NN cord-276598-tm0yj2sn 941 7 and and CC cord-276598-tm0yj2sn 941 8 acetic acetic JJ cord-276598-tm0yj2sn 941 9 acid acid NN cord-276598-tm0yj2sn 941 10 ( ( -LRB- cord-276598-tm0yj2sn 941 11 Scheme scheme NN cord-276598-tm0yj2sn 941 12 39 39 CD cord-276598-tm0yj2sn 941 13 ) ) -RRB- cord-276598-tm0yj2sn 942 1 [ [ -LRB- cord-276598-tm0yj2sn 942 2 1 1 CD cord-276598-tm0yj2sn 942 3 ] ] -RRB- cord-276598-tm0yj2sn 942 4 . . . cord-276598-tm0yj2sn 943 1 Meanwhile meanwhile RB cord-276598-tm0yj2sn 943 2 , , , cord-276598-tm0yj2sn 943 3 the the DT cord-276598-tm0yj2sn 943 4 aldehyde aldehyde NN cord-276598-tm0yj2sn 943 5 protonated protonate VBN cord-276598-tm0yj2sn 943 6 in in IN cord-276598-tm0yj2sn 943 7 the the DT cord-276598-tm0yj2sn 943 8 presence presence NN cord-276598-tm0yj2sn 943 9 of of IN cord-276598-tm0yj2sn 943 10 an an DT cord-276598-tm0yj2sn 943 11 acid acid NN cord-276598-tm0yj2sn 943 12 catalyst catalyst NN cord-276598-tm0yj2sn 943 13 , , , cord-276598-tm0yj2sn 943 14 TsOH TsOH NNP cord-276598-tm0yj2sn 943 15 , , , cord-276598-tm0yj2sn 943 16 reacts react VBZ cord-276598-tm0yj2sn 943 17 with with IN cord-276598-tm0yj2sn 943 18 the the DT cord-276598-tm0yj2sn 943 19 diethyl diethyl NNP cord-276598-tm0yj2sn 943 20 acetylphosphoramidate acetylphosphoramidate NNP cord-276598-tm0yj2sn 943 21 complex complex JJ cord-276598-tm0yj2sn 943 22 to to TO cord-276598-tm0yj2sn 943 23 give give VB cord-276598-tm0yj2sn 943 24 the the DT cord-276598-tm0yj2sn 943 25 cationic cationic JJ cord-276598-tm0yj2sn 943 26 diethyl diethyl NN cord-276598-tm0yj2sn 943 27 ( ( -LRB- cord-276598-tm0yj2sn 943 28 alkene alkene NN cord-276598-tm0yj2sn 943 29 - - HYPH cord-276598-tm0yj2sn 943 30 acetamido)phosphonate acetamido)phosphonate NNP cord-276598-tm0yj2sn 943 31 complex complex JJ cord-276598-tm0yj2sn 943 32 intermediate intermediate NN cord-276598-tm0yj2sn 943 33 . . . cord-276598-tm0yj2sn 944 1 The the DT cord-276598-tm0yj2sn 944 2 unstable unstable JJ cord-276598-tm0yj2sn 944 3 cationic cationic JJ cord-276598-tm0yj2sn 944 4 complex complex NN cord-276598-tm0yj2sn 944 5 undergoes undergo VBZ cord-276598-tm0yj2sn 944 6 rearrangement rearrangement NN cord-276598-tm0yj2sn 944 7 with with IN cord-276598-tm0yj2sn 944 8 a a DT cord-276598-tm0yj2sn 944 9 hydride hydride NN cord-276598-tm0yj2sn 944 10 shift shift NN cord-276598-tm0yj2sn 944 11 and and CC cord-276598-tm0yj2sn 944 12 deprotonation deprotonation NN cord-276598-tm0yj2sn 944 13 in in IN cord-276598-tm0yj2sn 944 14 presence presence NN cord-276598-tm0yj2sn 944 15 of of IN cord-276598-tm0yj2sn 944 16 TsO TsO NNP cord-276598-tm0yj2sn 944 17 − − NNP cord-276598-tm0yj2sn 944 18 to to TO cord-276598-tm0yj2sn 944 19 give give VB cord-276598-tm0yj2sn 944 20 a a DT cord-276598-tm0yj2sn 944 21 more more RBR cord-276598-tm0yj2sn 944 22 stable stable JJ cord-276598-tm0yj2sn 944 23 diethyl diethyl NN cord-276598-tm0yj2sn 944 24 acetyl(alk-1,3-diene)phosphoramidate acetyl(alk-1,3-diene)phosphoramidate RB cord-276598-tm0yj2sn 944 25 . . . cord-276598-tm0yj2sn 945 1 The the DT cord-276598-tm0yj2sn 945 2 subsequent subsequent JJ cord-276598-tm0yj2sn 945 3 direct direct JJ cord-276598-tm0yj2sn 945 4 addition addition NN cord-276598-tm0yj2sn 945 5 of of IN cord-276598-tm0yj2sn 945 6 the the DT cord-276598-tm0yj2sn 945 7 maleimide maleimide JJ cord-276598-tm0yj2sn 945 8 derivative derivative JJ cord-276598-tm0yj2sn 945 9 results result NNS cord-276598-tm0yj2sn 945 10 in in IN cord-276598-tm0yj2sn 945 11 a a DT cord-276598-tm0yj2sn 945 12 P P NNP cord-276598-tm0yj2sn 945 13 - - HYPH cord-276598-tm0yj2sn 945 14 N n CD cord-276598-tm0yj2sn 945 15 adduct adduct NN cord-276598-tm0yj2sn 945 16 intermediate intermediate NN cord-276598-tm0yj2sn 945 17 , , , cord-276598-tm0yj2sn 945 18 which which WDT cord-276598-tm0yj2sn 945 19 is be VBZ cord-276598-tm0yj2sn 945 20 deacetylated deacetylate VBN cord-276598-tm0yj2sn 945 21 in in IN cord-276598-tm0yj2sn 945 22 the the DT cord-276598-tm0yj2sn 945 23 presence presence NN cord-276598-tm0yj2sn 945 24 of of IN cord-276598-tm0yj2sn 945 25 acetic acetic JJ cord-276598-tm0yj2sn 945 26 acid acid NN cord-276598-tm0yj2sn 945 27 to to TO cord-276598-tm0yj2sn 945 28 afford afford VB cord-276598-tm0yj2sn 945 29 the the DT cord-276598-tm0yj2sn 945 30 desired desire VBN cord-276598-tm0yj2sn 945 31 product product NN cord-276598-tm0yj2sn 945 32 . . . cord-276598-tm0yj2sn 946 1 Scheme scheme NN cord-276598-tm0yj2sn 946 2 38 38 CD cord-276598-tm0yj2sn 946 3 . . . cord-276598-tm0yj2sn 947 1 Proposed propose VBN cord-276598-tm0yj2sn 947 2 mechanism mechanism NN cord-276598-tm0yj2sn 947 3 for for IN cord-276598-tm0yj2sn 947 4 hydrophosphinylation hydrophosphinylation NNP cord-276598-tm0yj2sn 947 5 route route NN cord-276598-tm0yj2sn 947 6 to to IN cord-276598-tm0yj2sn 947 7 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 947 8 . . . cord-276598-tm0yj2sn 948 1 Chabour Chabour NNP cord-276598-tm0yj2sn 948 2 et et FW cord-276598-tm0yj2sn 948 3 al al NNP cord-276598-tm0yj2sn 948 4 . . . cord-276598-tm0yj2sn 949 1 proposed propose VBD cord-276598-tm0yj2sn 949 2 a a DT cord-276598-tm0yj2sn 949 3 mechanism mechanism NN cord-276598-tm0yj2sn 949 4 of of IN cord-276598-tm0yj2sn 949 5 the the DT cord-276598-tm0yj2sn 949 6 reaction reaction NN cord-276598-tm0yj2sn 949 7 in in IN cord-276598-tm0yj2sn 949 8 which which WDT cord-276598-tm0yj2sn 949 9 ( ( -LRB- cord-276598-tm0yj2sn 949 10 EtO EtO NNP cord-276598-tm0yj2sn 949 11 ) ) -RRB- cord-276598-tm0yj2sn 949 12 2 2 CD cord-276598-tm0yj2sn 949 13 P(O)NH P(O)NH NNP cord-276598-tm0yj2sn 949 14 2 2 CD cord-276598-tm0yj2sn 949 15 reacts react VBZ cord-276598-tm0yj2sn 949 16 with with IN cord-276598-tm0yj2sn 949 17 ( ( -LRB- cord-276598-tm0yj2sn 949 18 or or CC cord-276598-tm0yj2sn 949 19 is be VBZ cord-276598-tm0yj2sn 949 20 activated activate VBN cord-276598-tm0yj2sn 949 21 by by IN cord-276598-tm0yj2sn 949 22 ) ) -RRB- cord-276598-tm0yj2sn 950 1 acetic acetic JJ cord-276598-tm0yj2sn 950 2 anhydride anhydride NN cord-276598-tm0yj2sn 950 3 to to TO cord-276598-tm0yj2sn 950 4 form form VB cord-276598-tm0yj2sn 950 5 diethyl diethyl JJ cord-276598-tm0yj2sn 950 6 acetylphosphoramidate acetylphosphoramidate NN cord-276598-tm0yj2sn 950 7 and and CC cord-276598-tm0yj2sn 950 8 acetic acetic JJ cord-276598-tm0yj2sn 950 9 acid acid NN cord-276598-tm0yj2sn 950 10 ( ( -LRB- cord-276598-tm0yj2sn 950 11 Scheme scheme NN cord-276598-tm0yj2sn 950 12 39 39 CD cord-276598-tm0yj2sn 950 13 ) ) -RRB- cord-276598-tm0yj2sn 951 1 [ [ -LRB- cord-276598-tm0yj2sn 951 2 1 1 CD cord-276598-tm0yj2sn 951 3 ] ] -RRB- cord-276598-tm0yj2sn 951 4 . . . cord-276598-tm0yj2sn 952 1 Meanwhile meanwhile RB cord-276598-tm0yj2sn 952 2 , , , cord-276598-tm0yj2sn 952 3 the the DT cord-276598-tm0yj2sn 952 4 aldehyde aldehyde NN cord-276598-tm0yj2sn 952 5 protonated protonate VBN cord-276598-tm0yj2sn 952 6 in in IN cord-276598-tm0yj2sn 952 7 the the DT cord-276598-tm0yj2sn 952 8 presence presence NN cord-276598-tm0yj2sn 952 9 of of IN cord-276598-tm0yj2sn 952 10 an an DT cord-276598-tm0yj2sn 952 11 acid acid NN cord-276598-tm0yj2sn 952 12 catalyst catalyst NN cord-276598-tm0yj2sn 952 13 , , , cord-276598-tm0yj2sn 952 14 TsOH TsOH NNP cord-276598-tm0yj2sn 952 15 , , , cord-276598-tm0yj2sn 952 16 reacts react VBZ cord-276598-tm0yj2sn 952 17 with with IN cord-276598-tm0yj2sn 952 18 the the DT cord-276598-tm0yj2sn 952 19 diethyl diethyl NNP cord-276598-tm0yj2sn 952 20 acetylphosphoramidate acetylphosphoramidate NNP cord-276598-tm0yj2sn 952 21 complex complex JJ cord-276598-tm0yj2sn 952 22 to to TO cord-276598-tm0yj2sn 952 23 give give VB cord-276598-tm0yj2sn 952 24 the the DT cord-276598-tm0yj2sn 952 25 cationic cationic JJ cord-276598-tm0yj2sn 952 26 diethyl diethyl NN cord-276598-tm0yj2sn 952 27 ( ( -LRB- cord-276598-tm0yj2sn 952 28 alkene alkene NN cord-276598-tm0yj2sn 952 29 - - HYPH cord-276598-tm0yj2sn 952 30 acetamido)phosphonate acetamido)phosphonate NNP cord-276598-tm0yj2sn 952 31 complex complex JJ cord-276598-tm0yj2sn 952 32 intermediate intermediate NN cord-276598-tm0yj2sn 952 33 . . . cord-276598-tm0yj2sn 953 1 The the DT cord-276598-tm0yj2sn 953 2 unstable unstable JJ cord-276598-tm0yj2sn 953 3 cationic cationic JJ cord-276598-tm0yj2sn 953 4 complex complex NN cord-276598-tm0yj2sn 953 5 undergoes undergo VBZ cord-276598-tm0yj2sn 953 6 rearrangement rearrangement NN cord-276598-tm0yj2sn 953 7 with with IN cord-276598-tm0yj2sn 953 8 a a DT cord-276598-tm0yj2sn 953 9 hydride hydride NN cord-276598-tm0yj2sn 953 10 shift shift NN cord-276598-tm0yj2sn 953 11 and and CC cord-276598-tm0yj2sn 953 12 deprotonation deprotonation NN cord-276598-tm0yj2sn 953 13 in in IN cord-276598-tm0yj2sn 953 14 presence presence NN cord-276598-tm0yj2sn 953 15 of of IN cord-276598-tm0yj2sn 953 16 TsO TsO NNP cord-276598-tm0yj2sn 953 17 − − NNP cord-276598-tm0yj2sn 953 18 to to TO cord-276598-tm0yj2sn 953 19 give give VB cord-276598-tm0yj2sn 953 20 a a DT cord-276598-tm0yj2sn 953 21 more more RBR cord-276598-tm0yj2sn 953 22 stable stable JJ cord-276598-tm0yj2sn 953 23 diethyl diethyl NN cord-276598-tm0yj2sn 953 24 acetyl(alk-1,3-diene)phosphoramidate acetyl(alk-1,3-diene)phosphoramidate RB cord-276598-tm0yj2sn 953 25 . . . cord-276598-tm0yj2sn 954 1 The the DT cord-276598-tm0yj2sn 954 2 subsequent subsequent JJ cord-276598-tm0yj2sn 954 3 direct direct JJ cord-276598-tm0yj2sn 954 4 addition addition NN cord-276598-tm0yj2sn 954 5 of of IN cord-276598-tm0yj2sn 954 6 the the DT cord-276598-tm0yj2sn 954 7 maleimide maleimide JJ cord-276598-tm0yj2sn 954 8 derivative derivative JJ cord-276598-tm0yj2sn 954 9 results result NNS cord-276598-tm0yj2sn 954 10 in in IN cord-276598-tm0yj2sn 954 11 a a DT cord-276598-tm0yj2sn 954 12 P P NNP cord-276598-tm0yj2sn 954 13 - - HYPH cord-276598-tm0yj2sn 954 14 N n CD cord-276598-tm0yj2sn 954 15 adduct adduct NN cord-276598-tm0yj2sn 954 16 intermediate intermediate NN cord-276598-tm0yj2sn 954 17 , , , cord-276598-tm0yj2sn 954 18 which which WDT cord-276598-tm0yj2sn 954 19 is be VBZ cord-276598-tm0yj2sn 954 20 deacetylated deacetylate VBN cord-276598-tm0yj2sn 954 21 in in IN cord-276598-tm0yj2sn 954 22 the the DT cord-276598-tm0yj2sn 954 23 presence presence NN cord-276598-tm0yj2sn 954 24 of of IN cord-276598-tm0yj2sn 954 25 acetic acetic JJ cord-276598-tm0yj2sn 954 26 acid acid NN cord-276598-tm0yj2sn 954 27 to to TO cord-276598-tm0yj2sn 954 28 afford afford VB cord-276598-tm0yj2sn 954 29 the the DT cord-276598-tm0yj2sn 954 30 desired desire VBN cord-276598-tm0yj2sn 954 31 product product NN cord-276598-tm0yj2sn 954 32 . . . cord-276598-tm0yj2sn 954 33 _SP cord-276598-tm0yj2sn 955 1 In in IN cord-276598-tm0yj2sn 955 2 this this DT cord-276598-tm0yj2sn 955 3 review review NN cord-276598-tm0yj2sn 955 4 , , , cord-276598-tm0yj2sn 955 5 the the DT cord-276598-tm0yj2sn 955 6 applications application NNS cord-276598-tm0yj2sn 955 7 , , , cord-276598-tm0yj2sn 955 8 syntheses synthesis NNS cord-276598-tm0yj2sn 955 9 , , , cord-276598-tm0yj2sn 955 10 and and CC cord-276598-tm0yj2sn 955 11 corresponding correspond VBG cord-276598-tm0yj2sn 955 12 mechanisms mechanism NNS cord-276598-tm0yj2sn 955 13 of of IN cord-276598-tm0yj2sn 955 14 phosphoramidates phosphoramidate NNS cord-276598-tm0yj2sn 955 15 have have VBP cord-276598-tm0yj2sn 955 16 been be VBN cord-276598-tm0yj2sn 955 17 discussed discuss VBN cord-276598-tm0yj2sn 955 18 in in IN cord-276598-tm0yj2sn 955 19 depth depth NN cord-276598-tm0yj2sn 955 20 . . . cord-276598-tm0yj2sn 956 1 As as IN cord-276598-tm0yj2sn 956 2 demonstrated demonstrate VBN cord-276598-tm0yj2sn 956 3 from from IN cord-276598-tm0yj2sn 956 4 the the DT cord-276598-tm0yj2sn 956 5 many many JJ cord-276598-tm0yj2sn 956 6 categories category NNS cord-276598-tm0yj2sn 956 7 for for IN cord-276598-tm0yj2sn 956 8 the the DT cord-276598-tm0yj2sn 956 9 uses use NNS cord-276598-tm0yj2sn 956 10 of of IN cord-276598-tm0yj2sn 956 11 synthetic synthetic JJ cord-276598-tm0yj2sn 956 12 P p NN cord-276598-tm0yj2sn 956 13 - - HYPH cord-276598-tm0yj2sn 956 14 Ns Ns NNP cord-276598-tm0yj2sn 956 15 , , , cord-276598-tm0yj2sn 956 16 it -PRON- PRP cord-276598-tm0yj2sn 956 17 is be VBZ cord-276598-tm0yj2sn 956 18 clear clear JJ cord-276598-tm0yj2sn 956 19 that that IN cord-276598-tm0yj2sn 956 20 the the DT cord-276598-tm0yj2sn 956 21 P P NNP cord-276598-tm0yj2sn 956 22 - - HYPH cord-276598-tm0yj2sn 956 23 N n CD cord-276598-tm0yj2sn 956 24 bond bond NN cord-276598-tm0yj2sn 956 25 motif motif NN cord-276598-tm0yj2sn 956 26 has have VBZ cord-276598-tm0yj2sn 956 27 structural structural JJ cord-276598-tm0yj2sn 956 28 importance importance NN cord-276598-tm0yj2sn 956 29 in in IN cord-276598-tm0yj2sn 956 30 diverse diverse JJ cord-276598-tm0yj2sn 956 31 fields field NNS cord-276598-tm0yj2sn 956 32 . . . cord-276598-tm0yj2sn 957 1 Early early JJ cord-276598-tm0yj2sn 957 2 synthetic synthetic JJ cord-276598-tm0yj2sn 957 3 routes route NNS cord-276598-tm0yj2sn 957 4 to to IN cord-276598-tm0yj2sn 957 5 P p NN cord-276598-tm0yj2sn 957 6 - - HYPH cord-276598-tm0yj2sn 957 7 Ns Ns NNP cord-276598-tm0yj2sn 957 8 are be VBP cord-276598-tm0yj2sn 957 9 limited limit VBN cord-276598-tm0yj2sn 957 10 due due IN cord-276598-tm0yj2sn 957 11 to to IN cord-276598-tm0yj2sn 957 12 harsh harsh JJ cord-276598-tm0yj2sn 957 13 reaction reaction NN cord-276598-tm0yj2sn 957 14 conditions condition NNS cord-276598-tm0yj2sn 957 15 , , , cord-276598-tm0yj2sn 957 16 air air NN cord-276598-tm0yj2sn 957 17 and and CC cord-276598-tm0yj2sn 957 18 Scheme scheme NN cord-276598-tm0yj2sn 957 19 39 39 CD cord-276598-tm0yj2sn 957 20 . . . cord-276598-tm0yj2sn 958 1 Proposed propose VBN cord-276598-tm0yj2sn 958 2 mechanism mechanism NN cord-276598-tm0yj2sn 958 3 for for IN cord-276598-tm0yj2sn 958 4 the the DT cord-276598-tm0yj2sn 958 5 synthesis synthesis NN cord-276598-tm0yj2sn 958 6 of of IN cord-276598-tm0yj2sn 958 7 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 958 8 via via IN cord-276598-tm0yj2sn 958 9 the the DT cord-276598-tm0yj2sn 958 10 phosphoamidatealdehyde phosphoamidatealdehyde NNP cord-276598-tm0yj2sn 958 11 - - HYPH cord-276598-tm0yj2sn 958 12 dienophile dienophile NNP cord-276598-tm0yj2sn 958 13 ( ( -LRB- cord-276598-tm0yj2sn 958 14 PAD pad NN cord-276598-tm0yj2sn 958 15 ) ) -RRB- cord-276598-tm0yj2sn 958 16 route route NN cord-276598-tm0yj2sn 958 17 . . . cord-276598-tm0yj2sn 959 1 In in IN cord-276598-tm0yj2sn 959 2 this this DT cord-276598-tm0yj2sn 959 3 review review NN cord-276598-tm0yj2sn 959 4 , , , cord-276598-tm0yj2sn 959 5 the the DT cord-276598-tm0yj2sn 959 6 applications application NNS cord-276598-tm0yj2sn 959 7 , , , cord-276598-tm0yj2sn 959 8 syntheses synthesis NNS cord-276598-tm0yj2sn 959 9 , , , cord-276598-tm0yj2sn 959 10 and and CC cord-276598-tm0yj2sn 959 11 corresponding correspond VBG cord-276598-tm0yj2sn 959 12 mechanisms mechanism NNS cord-276598-tm0yj2sn 959 13 of of IN cord-276598-tm0yj2sn 959 14 phosphoramidates phosphoramidate NNS cord-276598-tm0yj2sn 959 15 have have VBP cord-276598-tm0yj2sn 959 16 been be VBN cord-276598-tm0yj2sn 959 17 discussed discuss VBN cord-276598-tm0yj2sn 959 18 in in IN cord-276598-tm0yj2sn 959 19 depth depth NN cord-276598-tm0yj2sn 959 20 . . . cord-276598-tm0yj2sn 960 1 As as IN cord-276598-tm0yj2sn 960 2 demonstrated demonstrate VBN cord-276598-tm0yj2sn 960 3 from from IN cord-276598-tm0yj2sn 960 4 the the DT cord-276598-tm0yj2sn 960 5 many many JJ cord-276598-tm0yj2sn 960 6 categories category NNS cord-276598-tm0yj2sn 960 7 for for IN cord-276598-tm0yj2sn 960 8 the the DT cord-276598-tm0yj2sn 960 9 uses use NNS cord-276598-tm0yj2sn 960 10 of of IN cord-276598-tm0yj2sn 960 11 synthetic synthetic JJ cord-276598-tm0yj2sn 960 12 P p NN cord-276598-tm0yj2sn 960 13 - - HYPH cord-276598-tm0yj2sn 960 14 Ns Ns NNP cord-276598-tm0yj2sn 960 15 , , , cord-276598-tm0yj2sn 960 16 it -PRON- PRP cord-276598-tm0yj2sn 960 17 is be VBZ cord-276598-tm0yj2sn 960 18 clear clear JJ cord-276598-tm0yj2sn 960 19 that that IN cord-276598-tm0yj2sn 960 20 the the DT cord-276598-tm0yj2sn 960 21 P P NNP cord-276598-tm0yj2sn 960 22 - - HYPH cord-276598-tm0yj2sn 960 23 N n CD cord-276598-tm0yj2sn 960 24 bond bond NN cord-276598-tm0yj2sn 960 25 motif motif NN cord-276598-tm0yj2sn 960 26 has have VBZ cord-276598-tm0yj2sn 960 27 structural structural JJ cord-276598-tm0yj2sn 960 28 importance importance NN cord-276598-tm0yj2sn 960 29 in in IN cord-276598-tm0yj2sn 960 30 diverse diverse JJ cord-276598-tm0yj2sn 960 31 fields field NNS cord-276598-tm0yj2sn 960 32 . . . cord-276598-tm0yj2sn 961 1 Early early JJ cord-276598-tm0yj2sn 961 2 synthetic synthetic JJ cord-276598-tm0yj2sn 961 3 routes route NNS cord-276598-tm0yj2sn 961 4 to to IN cord-276598-tm0yj2sn 961 5 P p NN cord-276598-tm0yj2sn 961 6 - - HYPH cord-276598-tm0yj2sn 961 7 Ns Ns NNP cord-276598-tm0yj2sn 961 8 are be VBP cord-276598-tm0yj2sn 961 9 limited limit VBN cord-276598-tm0yj2sn 961 10 due due IN cord-276598-tm0yj2sn 961 11 to to IN cord-276598-tm0yj2sn 961 12 harsh harsh JJ cord-276598-tm0yj2sn 961 13 reaction reaction NN cord-276598-tm0yj2sn 961 14 conditions condition NNS cord-276598-tm0yj2sn 961 15 , , , cord-276598-tm0yj2sn 961 16 air air NN cord-276598-tm0yj2sn 961 17 and and CC cord-276598-tm0yj2sn 961 18 moisture moisture NN cord-276598-tm0yj2sn 961 19 - - HYPH cord-276598-tm0yj2sn 961 20 sensitive sensitive JJ cord-276598-tm0yj2sn 961 21 reagents reagent NNS cord-276598-tm0yj2sn 961 22 , , , cord-276598-tm0yj2sn 961 23 multi multi JJ cord-276598-tm0yj2sn 961 24 - - JJ cord-276598-tm0yj2sn 961 25 step step JJ cord-276598-tm0yj2sn 961 26 synthesis synthesis NN cord-276598-tm0yj2sn 961 27 , , , cord-276598-tm0yj2sn 961 28 and and CC cord-276598-tm0yj2sn 961 29 undesirable undesirable JJ cord-276598-tm0yj2sn 961 30 side side NN cord-276598-tm0yj2sn 961 31 reactions reaction NNS cord-276598-tm0yj2sn 961 32 . . . cord-276598-tm0yj2sn 962 1 The the DT cord-276598-tm0yj2sn 962 2 separation separation NN cord-276598-tm0yj2sn 962 3 and and CC cord-276598-tm0yj2sn 962 4 purification purification NN cord-276598-tm0yj2sn 962 5 of of IN cord-276598-tm0yj2sn 962 6 P p NN cord-276598-tm0yj2sn 962 7 - - HYPH cord-276598-tm0yj2sn 962 8 Ns Ns NNP cord-276598-tm0yj2sn 962 9 is be VBZ cord-276598-tm0yj2sn 962 10 also also RB cord-276598-tm0yj2sn 962 11 a a DT cord-276598-tm0yj2sn 962 12 challenge challenge NN cord-276598-tm0yj2sn 962 13 . . . cord-276598-tm0yj2sn 963 1 In in IN cord-276598-tm0yj2sn 963 2 particular particular JJ cord-276598-tm0yj2sn 963 3 , , , cord-276598-tm0yj2sn 963 4 most most JJS cord-276598-tm0yj2sn 963 5 of of IN cord-276598-tm0yj2sn 963 6 the the DT cord-276598-tm0yj2sn 963 7 synthetic synthetic JJ cord-276598-tm0yj2sn 963 8 strategies strategy NNS cord-276598-tm0yj2sn 963 9 involve involve VBP cord-276598-tm0yj2sn 963 10 extraction extraction NN cord-276598-tm0yj2sn 963 11 and/or and/or CC cord-276598-tm0yj2sn 963 12 column column NN cord-276598-tm0yj2sn 963 13 chromatography chromatography NN cord-276598-tm0yj2sn 963 14 , , , cord-276598-tm0yj2sn 963 15 which which WDT cord-276598-tm0yj2sn 963 16 not not RB cord-276598-tm0yj2sn 963 17 only only RB cord-276598-tm0yj2sn 963 18 requires require VBZ cord-276598-tm0yj2sn 963 19 large large JJ cord-276598-tm0yj2sn 963 20 amounts amount NNS cord-276598-tm0yj2sn 963 21 of of IN cord-276598-tm0yj2sn 963 22 solvent solvent NN cord-276598-tm0yj2sn 963 23 , , , cord-276598-tm0yj2sn 963 24 but but CC cord-276598-tm0yj2sn 963 25 also also RB cord-276598-tm0yj2sn 963 26 takes take VBZ cord-276598-tm0yj2sn 963 27 a a DT cord-276598-tm0yj2sn 963 28 significant significant JJ cord-276598-tm0yj2sn 963 29 amount amount NN cord-276598-tm0yj2sn 963 30 of of IN cord-276598-tm0yj2sn 963 31 time time NN cord-276598-tm0yj2sn 963 32 . . . cord-276598-tm0yj2sn 964 1 Therefore therefore RB cord-276598-tm0yj2sn 964 2 , , , cord-276598-tm0yj2sn 964 3 unsurprisingly unsurprisingly RB cord-276598-tm0yj2sn 964 4 , , , cord-276598-tm0yj2sn 964 5 extensive extensive JJ cord-276598-tm0yj2sn 964 6 studies study NNS cord-276598-tm0yj2sn 964 7 have have VBP cord-276598-tm0yj2sn 964 8 been be VBN cord-276598-tm0yj2sn 964 9 undertaken undertake VBN cord-276598-tm0yj2sn 964 10 ( ( -LRB- cord-276598-tm0yj2sn 964 11 with with IN cord-276598-tm0yj2sn 964 12 more more JJR cord-276598-tm0yj2sn 964 13 to to TO cord-276598-tm0yj2sn 964 14 come come VB cord-276598-tm0yj2sn 964 15 in in IN cord-276598-tm0yj2sn 964 16 the the DT cord-276598-tm0yj2sn 964 17 future future NN cord-276598-tm0yj2sn 964 18 ) ) -RRB- cord-276598-tm0yj2sn 964 19 for for IN cord-276598-tm0yj2sn 964 20 more more RBR cord-276598-tm0yj2sn 964 21 sustainable sustainable JJ cord-276598-tm0yj2sn 964 22 , , , cord-276598-tm0yj2sn 964 23 efficient efficient JJ cord-276598-tm0yj2sn 964 24 , , , cord-276598-tm0yj2sn 964 25 atom atom NN cord-276598-tm0yj2sn 964 26 economic economic JJ cord-276598-tm0yj2sn 964 27 , , , cord-276598-tm0yj2sn 964 28 selective selective JJ cord-276598-tm0yj2sn 964 29 , , , cord-276598-tm0yj2sn 964 30 and and CC cord-276598-tm0yj2sn 964 31 milder mild JJR cord-276598-tm0yj2sn 964 32 synthetic synthetic JJ cord-276598-tm0yj2sn 964 33 procedures procedure NNS cord-276598-tm0yj2sn 964 34 toward toward IN cord-276598-tm0yj2sn 964 35 P p NN cord-276598-tm0yj2sn 964 36 - - HYPH cord-276598-tm0yj2sn 964 37 Ns Ns NNP cord-276598-tm0yj2sn 964 38 . . . cord-276598-tm0yj2sn 965 1 In in IN cord-276598-tm0yj2sn 965 2 addition addition NN cord-276598-tm0yj2sn 965 3 , , , cord-276598-tm0yj2sn 965 4 the the DT cord-276598-tm0yj2sn 965 5 discussed discuss VBN cord-276598-tm0yj2sn 965 6 mechanisms mechanism NNS cord-276598-tm0yj2sn 965 7 require require VBP cord-276598-tm0yj2sn 965 8 a a DT cord-276598-tm0yj2sn 965 9 deeper deep JJR cord-276598-tm0yj2sn 965 10 understanding understanding NN cord-276598-tm0yj2sn 965 11 of of IN cord-276598-tm0yj2sn 965 12 the the DT cord-276598-tm0yj2sn 965 13 associated associate VBN cord-276598-tm0yj2sn 965 14 phosphorus phosphorus NN cord-276598-tm0yj2sn 965 15 chemistry chemistry NN cord-276598-tm0yj2sn 965 16 in in IN cord-276598-tm0yj2sn 965 17 order order NN cord-276598-tm0yj2sn 965 18 to to TO cord-276598-tm0yj2sn 965 19 have have VB cord-276598-tm0yj2sn 965 20 better well JJR cord-276598-tm0yj2sn 965 21 synthetic synthetic JJ cord-276598-tm0yj2sn 965 22 control control NN cord-276598-tm0yj2sn 965 23 and and CC cord-276598-tm0yj2sn 965 24 to to TO cord-276598-tm0yj2sn 965 25 optimize optimize VB cord-276598-tm0yj2sn 965 26 the the DT cord-276598-tm0yj2sn 965 27 yield yield NN cord-276598-tm0yj2sn 965 28 and and CC cord-276598-tm0yj2sn 965 29 selectivity selectivity NN cord-276598-tm0yj2sn 965 30 toward toward IN cord-276598-tm0yj2sn 965 31 P P NNP cord-276598-tm0yj2sn 965 32 - - HYPH cord-276598-tm0yj2sn 965 33 N n CD cord-276598-tm0yj2sn 965 34 products product NNS cord-276598-tm0yj2sn 965 35 . . . cord-276598-tm0yj2sn 966 1 To to TO cord-276598-tm0yj2sn 966 2 overcome overcome VB cord-276598-tm0yj2sn 966 3 these these DT cord-276598-tm0yj2sn 966 4 challenges challenge NNS cord-276598-tm0yj2sn 966 5 , , , cord-276598-tm0yj2sn 966 6 it -PRON- PRP cord-276598-tm0yj2sn 966 7 is be VBZ cord-276598-tm0yj2sn 966 8 predicted predict VBN cord-276598-tm0yj2sn 966 9 that that IN cord-276598-tm0yj2sn 966 10 better well JJR cord-276598-tm0yj2sn 966 11 catalysts catalyst NNS cord-276598-tm0yj2sn 966 12 , , , cord-276598-tm0yj2sn 966 13 improved improve VBN cord-276598-tm0yj2sn 966 14 reaction reaction NN cord-276598-tm0yj2sn 966 15 conditions condition NNS cord-276598-tm0yj2sn 966 16 , , , cord-276598-tm0yj2sn 966 17 and and CC cord-276598-tm0yj2sn 966 18 new new JJ cord-276598-tm0yj2sn 966 19 solvent solvent NN cord-276598-tm0yj2sn 966 20 solutions solution NNS cord-276598-tm0yj2sn 966 21 for for IN cord-276598-tm0yj2sn 966 22 separating separate VBG cord-276598-tm0yj2sn 966 23 the the DT cord-276598-tm0yj2sn 966 24 product product NN cord-276598-tm0yj2sn 966 25 from from IN cord-276598-tm0yj2sn 966 26 the the DT cord-276598-tm0yj2sn 966 27 by by NN cord-276598-tm0yj2sn 966 28 - - HYPH cord-276598-tm0yj2sn 966 29 products product NNS cord-276598-tm0yj2sn 966 30 and and CC cord-276598-tm0yj2sn 966 31 potentially potentially RB cord-276598-tm0yj2sn 966 32 improving improve VBG cord-276598-tm0yj2sn 966 33 selectivity selectivity NN cord-276598-tm0yj2sn 966 34 are be VBP cord-276598-tm0yj2sn 966 35 in in IN cord-276598-tm0yj2sn 966 36 the the DT cord-276598-tm0yj2sn 966 37 forecast forecast NN cord-276598-tm0yj2sn 966 38 . . . cord-276598-tm0yj2sn 967 1 For for IN cord-276598-tm0yj2sn 967 2 example example NN cord-276598-tm0yj2sn 967 3 , , , cord-276598-tm0yj2sn 967 4 there there EX cord-276598-tm0yj2sn 967 5 is be VBZ cord-276598-tm0yj2sn 967 6 a a DT cord-276598-tm0yj2sn 967 7 sharp sharp JJ cord-276598-tm0yj2sn 967 8 rise rise NN cord-276598-tm0yj2sn 967 9 into into IN cord-276598-tm0yj2sn 967 10 synthetic synthetic JJ cord-276598-tm0yj2sn 967 11 research research NN cord-276598-tm0yj2sn 967 12 under under IN cord-276598-tm0yj2sn 967 13 solvent solvent NN cord-276598-tm0yj2sn 967 14 - - HYPH cord-276598-tm0yj2sn 967 15 free free JJ cord-276598-tm0yj2sn 967 16 conditions condition NNS cord-276598-tm0yj2sn 967 17 or or CC cord-276598-tm0yj2sn 967 18 using use VBG cord-276598-tm0yj2sn 967 19 ionic ionic JJ cord-276598-tm0yj2sn 967 20 liquids liquid NNS cord-276598-tm0yj2sn 967 21 ( ( -LRB- cord-276598-tm0yj2sn 967 22 ILs ILs NNP cord-276598-tm0yj2sn 967 23 ) ) -RRB- cord-276598-tm0yj2sn 967 24 and and CC cord-276598-tm0yj2sn 967 25 deep deep JJ cord-276598-tm0yj2sn 967 26 eutectic eutectic JJ cord-276598-tm0yj2sn 967 27 solvents solvent NNS cord-276598-tm0yj2sn 967 28 ( ( -LRB- cord-276598-tm0yj2sn 967 29 DES DES NNP cord-276598-tm0yj2sn 967 30 ) ) -RRB- cord-276598-tm0yj2sn 967 31 . . . cord-276598-tm0yj2sn 968 1 These these DT cord-276598-tm0yj2sn 968 2 can can MD cord-276598-tm0yj2sn 968 3 be be VB cord-276598-tm0yj2sn 968 4 environmentally environmentally RB cord-276598-tm0yj2sn 968 5 benign benign JJ cord-276598-tm0yj2sn 968 6 , , , cord-276598-tm0yj2sn 968 7 highly highly RB cord-276598-tm0yj2sn 968 8 versatile versatile JJ cord-276598-tm0yj2sn 968 9 , , , cord-276598-tm0yj2sn 968 10 selective selective JJ cord-276598-tm0yj2sn 968 11 , , , cord-276598-tm0yj2sn 968 12 and and CC cord-276598-tm0yj2sn 968 13 recoverable recoverable JJ cord-276598-tm0yj2sn 968 14 solvents solvent NNS cord-276598-tm0yj2sn 968 15 for for IN cord-276598-tm0yj2sn 968 16 use use NN cord-276598-tm0yj2sn 968 17 in in IN cord-276598-tm0yj2sn 968 18 catalysis catalysis NN cord-276598-tm0yj2sn 968 19 . . . cord-276598-tm0yj2sn 968 20 _SP cord-276598-tm0yj2sn 969 1 Diastereoselective diastereoselective JJ cord-276598-tm0yj2sn 969 2 multicomponent multicomponent NN cord-276598-tm0yj2sn 969 3 phosphoramidate phosphoramidate NN cord-276598-tm0yj2sn 969 4 - - HYPH cord-276598-tm0yj2sn 969 5 aldehydedienophile aldehydedienophile NNP cord-276598-tm0yj2sn 969 6 ( ( -LRB- cord-276598-tm0yj2sn 969 7 PAD pad NN cord-276598-tm0yj2sn 969 8 ) ) -RRB- cord-276598-tm0yj2sn 969 9 process process NN cord-276598-tm0yj2sn 969 10 for for IN cord-276598-tm0yj2sn 969 11 the the DT cord-276598-tm0yj2sn 969 12 synthesis synthesis NN cord-276598-tm0yj2sn 969 13 of of IN cord-276598-tm0yj2sn 969 14 polysubstituted polysubstituted NNP cord-276598-tm0yj2sn 969 15 cyclohex-2-enyl cyclohex-2-enyl NN cord-276598-tm0yj2sn 969 16 - - HYPH cord-276598-tm0yj2sn 969 17 amine amine NN cord-276598-tm0yj2sn 969 18 derivatives derivative NNS cord-276598-tm0yj2sn 969 19 Total Total NNP cord-276598-tm0yj2sn 969 20 Synthesis Synthesis NNP cord-276598-tm0yj2sn 969 21 of of IN cord-276598-tm0yj2sn 969 22 Agrocin Agrocin NNP cord-276598-tm0yj2sn 969 23 84 84 CD cord-276598-tm0yj2sn 969 24 and and CC cord-276598-tm0yj2sn 969 25 Phosmidosine Phosmidosine NNP cord-276598-tm0yj2sn 969 26 as as IN cord-276598-tm0yj2sn 969 27 Naturally naturally RB cord-276598-tm0yj2sn 970 1 Occurring occur VBG cord-276598-tm0yj2sn 970 2 Nucleotidic Nucleotidic NNP cord-276598-tm0yj2sn 970 3 Antibiotics Antibiotics NNPS cord-276598-tm0yj2sn 971 1 Having have VBG cord-276598-tm0yj2sn 972 1 P p NN cord-276598-tm0yj2sn 972 2 - - HYPH cord-276598-tm0yj2sn 972 3 N N NNP cord-276598-tm0yj2sn 972 4 Bond Bond NNP cord-276598-tm0yj2sn 972 5 Linkages Linkages NNP cord-276598-tm0yj2sn 972 6 Natural Natural NNP cord-276598-tm0yj2sn 972 7 Products Products NNPS cord-276598-tm0yj2sn 972 8 Containing contain VBG cord-276598-tm0yj2sn 972 9 ' ' `` cord-276598-tm0yj2sn 972 10 Rare Rare NNP cord-276598-tm0yj2sn 972 11 ' ' '' cord-276598-tm0yj2sn 972 12 Organophosphorus Organophosphorus NNP cord-276598-tm0yj2sn 972 13 Functional Functional NNP cord-276598-tm0yj2sn 972 14 Groups Groups NNPS cord-276598-tm0yj2sn 972 15 Chemical Chemical NNP cord-276598-tm0yj2sn 972 16 Structure Structure NNP cord-276598-tm0yj2sn 972 17 and and CC cord-276598-tm0yj2sn 972 18 Translation Translation NNP cord-276598-tm0yj2sn 972 19 Inhibition Inhibition NNP cord-276598-tm0yj2sn 972 20 Studies Studies NNPS cord-276598-tm0yj2sn 972 21 of of IN cord-276598-tm0yj2sn 972 22 the the DT cord-276598-tm0yj2sn 972 23 Antibiotic Antibiotic NNP cord-276598-tm0yj2sn 972 24 Microcin Microcin NNP cord-276598-tm0yj2sn 972 25 C7 C7 NNP cord-276598-tm0yj2sn 972 26 Properties Properties NNPS cord-276598-tm0yj2sn 972 27 of of IN cord-276598-tm0yj2sn 972 28 a a DT cord-276598-tm0yj2sn 972 29 toxic toxic JJ cord-276598-tm0yj2sn 972 30 phospholipid phospholipid NN cord-276598-tm0yj2sn 972 31 in in IN cord-276598-tm0yj2sn 972 32 the the DT cord-276598-tm0yj2sn 972 33 northern northern JJ cord-276598-tm0yj2sn 972 34 blenny blenny NN cord-276598-tm0yj2sn 972 35 roe roe NNP cord-276598-tm0yj2sn 972 36 Focus Focus NNP cord-276598-tm0yj2sn 972 37 on on IN cord-276598-tm0yj2sn 972 38 Phosphoarginine Phosphoarginine NNP cord-276598-tm0yj2sn 972 39 and and CC cord-276598-tm0yj2sn 972 40 Phospholysine Phospholysine NNP cord-276598-tm0yj2sn 972 41 Encyclopedia Encyclopedia NNP cord-276598-tm0yj2sn 972 42 of of IN cord-276598-tm0yj2sn 972 43 Metalloproteins Metalloproteins NNP cord-276598-tm0yj2sn 972 44 Chapter Chapter NNP cord-276598-tm0yj2sn 972 45 111-Thermolysin 111-Thermolysin NNP cord-276598-tm0yj2sn 972 46 and and CC cord-276598-tm0yj2sn 972 47 Related related JJ cord-276598-tm0yj2sn 972 48 Bacillus Bacillus NNP cord-276598-tm0yj2sn 972 49 Metallopeptidases Metallopeptidases NNP cord-276598-tm0yj2sn 972 50 Synthesis Synthesis NNP cord-276598-tm0yj2sn 972 51 of of IN cord-276598-tm0yj2sn 972 52 nucleotide nucleotide JJ cord-276598-tm0yj2sn 972 53 antibiotics antibiotic NNS cord-276598-tm0yj2sn 973 1 having have VBG cord-276598-tm0yj2sn 973 2 N n CD cord-276598-tm0yj2sn 973 3 - - HYPH cord-276598-tm0yj2sn 973 4 acyl acyl NN cord-276598-tm0yj2sn 973 5 phosphoramidate phosphoramidate NNP cord-276598-tm0yj2sn 973 6 linkages linkage NNS cord-276598-tm0yj2sn 973 7 Structure Structure NNP cord-276598-tm0yj2sn 973 8 of of IN cord-276598-tm0yj2sn 973 9 the the DT cord-276598-tm0yj2sn 973 10 antifungal antifungal JJ cord-276598-tm0yj2sn 973 11 nucleotide nucleotide NN cord-276598-tm0yj2sn 973 12 antibiotic antibiotic JJ cord-276598-tm0yj2sn 973 13 phosmidosine phosmidosine NNP cord-276598-tm0yj2sn 974 1 The the DT cord-276598-tm0yj2sn 974 2 diverse diverse JJ cord-276598-tm0yj2sn 974 3 pharmacology pharmacology NN cord-276598-tm0yj2sn 974 4 and and CC cord-276598-tm0yj2sn 974 5 medicinal medicinal JJ cord-276598-tm0yj2sn 974 6 chemistry chemistry NN cord-276598-tm0yj2sn 974 7 of of IN cord-276598-tm0yj2sn 974 8 phosphoramidates phosphoramidates NN cord-276598-tm0yj2sn 974 9 - - HYPH cord-276598-tm0yj2sn 974 10 A a DT cord-276598-tm0yj2sn 974 11 review review NN cord-276598-tm0yj2sn 974 12 Remdesivir Remdesivir NNP cord-276598-tm0yj2sn 974 13 for for IN cord-276598-tm0yj2sn 974 14 severe severe JJ cord-276598-tm0yj2sn 974 15 acute acute JJ cord-276598-tm0yj2sn 974 16 respiratory respiratory JJ cord-276598-tm0yj2sn 974 17 syndrome syndrome NN cord-276598-tm0yj2sn 974 18 coronavirus coronavirus NN cord-276598-tm0yj2sn 974 19 2 2 CD cord-276598-tm0yj2sn 974 20 causing cause VBG cord-276598-tm0yj2sn 974 21 COVID-19 covid-19 CD cord-276598-tm0yj2sn 974 22 : : : cord-276598-tm0yj2sn 975 1 An an DT cord-276598-tm0yj2sn 975 2 evaluation evaluation NN cord-276598-tm0yj2sn 975 3 of of IN cord-276598-tm0yj2sn 975 4 the the DT cord-276598-tm0yj2sn 975 5 evidence evidence NN cord-276598-tm0yj2sn 975 6 N n NN cord-276598-tm0yj2sn 975 7 - - HYPH cord-276598-tm0yj2sn 975 8 phosphorylation phosphorylation NN cord-276598-tm0yj2sn 975 9 labeling labeling NN cord-276598-tm0yj2sn 975 10 for for IN cord-276598-tm0yj2sn 975 11 analysis analysis NN cord-276598-tm0yj2sn 975 12 of of IN cord-276598-tm0yj2sn 975 13 twenty twenty CD cord-276598-tm0yj2sn 975 14 natural natural JJ cord-276598-tm0yj2sn 975 15 amino amino NN cord-276598-tm0yj2sn 975 16 acids acid NNS cord-276598-tm0yj2sn 975 17 and and CC cord-276598-tm0yj2sn 975 18 small small JJ cord-276598-tm0yj2sn 975 19 peptides peptide NNS cord-276598-tm0yj2sn 975 20 by by IN cord-276598-tm0yj2sn 975 21 using use VBG cord-276598-tm0yj2sn 975 22 matrix matrix NN cord-276598-tm0yj2sn 975 23 - - HYPH cord-276598-tm0yj2sn 975 24 assisted assist VBN cord-276598-tm0yj2sn 975 25 laser laser NN cord-276598-tm0yj2sn 975 26 desorption desorption NN cord-276598-tm0yj2sn 975 27 / / SYM cord-276598-tm0yj2sn 975 28 ionization ionization NN cord-276598-tm0yj2sn 975 29 time time NN cord-276598-tm0yj2sn 975 30 - - HYPH cord-276598-tm0yj2sn 975 31 of of IN cord-276598-tm0yj2sn 975 32 - - HYPH cord-276598-tm0yj2sn 975 33 flight flight NN cord-276598-tm0yj2sn 975 34 mass mass NN cord-276598-tm0yj2sn 975 35 spectrometry spectrometry NN cord-276598-tm0yj2sn 975 36 Structural Structural NNP cord-276598-tm0yj2sn 975 37 Effect effect NN cord-276598-tm0yj2sn 975 38 of of IN cord-276598-tm0yj2sn 975 39 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 975 40 Derivatives Derivatives NNPS cord-276598-tm0yj2sn 975 41 on on IN cord-276598-tm0yj2sn 975 42 the the DT cord-276598-tm0yj2sn 975 43 Thermal Thermal NNP cord-276598-tm0yj2sn 975 44 and and CC cord-276598-tm0yj2sn 975 45 Flame Flame NNP cord-276598-tm0yj2sn 975 46 Retardant Retardant NNP cord-276598-tm0yj2sn 975 47 Behaviors Behaviors NNPS cord-276598-tm0yj2sn 975 48 of of IN cord-276598-tm0yj2sn 975 49 Treated treat VBN cord-276598-tm0yj2sn 975 50 Cotton Cotton NNP cord-276598-tm0yj2sn 975 51 Cellulose Cellulose NNP cord-276598-tm0yj2sn 975 52 Electrochemical electrochemical JJ cord-276598-tm0yj2sn 975 53 determination determination NN cord-276598-tm0yj2sn 975 54 of of IN cord-276598-tm0yj2sn 975 55 the the DT cord-276598-tm0yj2sn 975 56 organophosphate organophosphate NN cord-276598-tm0yj2sn 975 57 compound compound NN cord-276598-tm0yj2sn 975 58 Fenamiphos Fenamiphos NNP cord-276598-tm0yj2sn 975 59 and and CC cord-276598-tm0yj2sn 975 60 its -PRON- PRP$ cord-276598-tm0yj2sn 975 61 main main JJ cord-276598-tm0yj2sn 975 62 metabolite metabolite NN cord-276598-tm0yj2sn 975 63 , , , cord-276598-tm0yj2sn 975 64 Fenamiphos Fenamiphos NNP cord-276598-tm0yj2sn 975 65 sulfoxide sulfoxide NN cord-276598-tm0yj2sn 975 66 New New NNP cord-276598-tm0yj2sn 975 67 o o NN cord-276598-tm0yj2sn 975 68 - - HYPH cord-276598-tm0yj2sn 975 69 substituted substitute VBN cord-276598-tm0yj2sn 975 70 diphenylphosphinic diphenylphosphinic JJ cord-276598-tm0yj2sn 975 71 amide amide NN cord-276598-tm0yj2sn 975 72 ligands ligand NNS cord-276598-tm0yj2sn 975 73 : : : cord-276598-tm0yj2sn 975 74 Synthesis synthesis NN cord-276598-tm0yj2sn 975 75 , , , cord-276598-tm0yj2sn 975 76 characterization characterization NN cord-276598-tm0yj2sn 975 77 and and CC cord-276598-tm0yj2sn 975 78 complexation complexation NN cord-276598-tm0yj2sn 975 79 with with IN cord-276598-tm0yj2sn 975 80 Zn Zn NNP cord-276598-tm0yj2sn 975 81 2 2 CD cord-276598-tm0yj2sn 976 1 + + CC cord-276598-tm0yj2sn 977 1 , , , cord-276598-tm0yj2sn 977 2 Cu Cu NNP cord-276598-tm0yj2sn 977 3 2 2 CD cord-276598-tm0yj2sn 977 4 + + CC cord-276598-tm0yj2sn 977 5 and and CC cord-276598-tm0yj2sn 977 6 Y Y NNP cord-276598-tm0yj2sn 977 7 3 3 CD cord-276598-tm0yj2sn 978 1 + + CC cord-276598-tm0yj2sn 979 1 Significant significant JJ cord-276598-tm0yj2sn 979 2 enhanced enhance VBN cord-276598-tm0yj2sn 979 3 uranyl uranyl NN cord-276598-tm0yj2sn 979 4 ions ion NNS cord-276598-tm0yj2sn 979 5 extraction extraction NN cord-276598-tm0yj2sn 979 6 efficiency efficiency NN cord-276598-tm0yj2sn 979 7 with with IN cord-276598-tm0yj2sn 979 8 phosphoramidate phosphoramidate NN cord-276598-tm0yj2sn 979 9 - - HYPH cord-276598-tm0yj2sn 979 10 functionalized functionalize VBN cord-276598-tm0yj2sn 979 11 ionic ionic JJ cord-276598-tm0yj2sn 979 12 liquids liquid NNS cord-276598-tm0yj2sn 979 13 via via IN cord-276598-tm0yj2sn 979 14 synergistic synergistic JJ cord-276598-tm0yj2sn 979 15 effect effect NN cord-276598-tm0yj2sn 979 16 of of IN cord-276598-tm0yj2sn 979 17 coordination coordination NN cord-276598-tm0yj2sn 979 18 and and CC cord-276598-tm0yj2sn 979 19 hydrogen hydrogen NN cord-276598-tm0yj2sn 979 20 bond bond NN cord-276598-tm0yj2sn 980 1 The the DT cord-276598-tm0yj2sn 980 2 tribochemical tribochemical JJ cord-276598-tm0yj2sn 980 3 study study NN cord-276598-tm0yj2sn 980 4 of of IN cord-276598-tm0yj2sn 980 5 novel novel JJ cord-276598-tm0yj2sn 980 6 phosphorous phosphorous NN cord-276598-tm0yj2sn 980 7 - - HYPH cord-276598-tm0yj2sn 980 8 nitrogen nitrogen NN cord-276598-tm0yj2sn 980 9 ( ( -LRB- cord-276598-tm0yj2sn 980 10 P P NNP cord-276598-tm0yj2sn 980 11 - - HYPH cord-276598-tm0yj2sn 980 12 N N NNP cord-276598-tm0yj2sn 980 13 ) ) -RRB- cord-276598-tm0yj2sn 980 14 type type NN cord-276598-tm0yj2sn 980 15 phosphoramidate phosphoramidate NN cord-276598-tm0yj2sn 980 16 additives additive NNS cord-276598-tm0yj2sn 980 17 in in IN cord-276598-tm0yj2sn 980 18 water water NN cord-276598-tm0yj2sn 981 1 The the DT cord-276598-tm0yj2sn 982 1 Organophosphate Organophosphate NNP cord-276598-tm0yj2sn 982 2 Pesticides Pesticides NNP cord-276598-tm0yj2sn 982 3 Synthesis Synthesis NNP cord-276598-tm0yj2sn 982 4 and and CC cord-276598-tm0yj2sn 982 5 insecticidal insecticidal JJ cord-276598-tm0yj2sn 982 6 activity activity NN cord-276598-tm0yj2sn 982 7 of of IN cord-276598-tm0yj2sn 982 8 new new JJ cord-276598-tm0yj2sn 982 9 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 982 10 Organophosphorus Organophosphorus NNP cord-276598-tm0yj2sn 982 11 pesticides pesticide NNS cord-276598-tm0yj2sn 982 12 as as IN cord-276598-tm0yj2sn 982 13 food food NN cord-276598-tm0yj2sn 982 14 chain chain NN cord-276598-tm0yj2sn 982 15 contaminants contaminant NNS cord-276598-tm0yj2sn 982 16 and and CC cord-276598-tm0yj2sn 982 17 type type NN cord-276598-tm0yj2sn 982 18 2 2 CD cord-276598-tm0yj2sn 982 19 diabetes diabetes NN cord-276598-tm0yj2sn 982 20 : : : cord-276598-tm0yj2sn 982 21 A a DT cord-276598-tm0yj2sn 982 22 review review NN cord-276598-tm0yj2sn 982 23 Current current JJ cord-276598-tm0yj2sn 982 24 issues issue NNS cord-276598-tm0yj2sn 982 25 in in IN cord-276598-tm0yj2sn 982 26 organophosphate organophosphate NN cord-276598-tm0yj2sn 982 27 toxicology toxicology NN cord-276598-tm0yj2sn 982 28 Saligenin Saligenin NNP cord-276598-tm0yj2sn 982 29 Cyclic Cyclic NNP cord-276598-tm0yj2sn 982 30 Phosphoramidates Phosphoramidates NNPS cord-276598-tm0yj2sn 982 31 and and CC cord-276598-tm0yj2sn 982 32 Phosphoramidothionates Phosphoramidothionates NNPS cord-276598-tm0yj2sn 982 33 as as IN cord-276598-tm0yj2sn 982 34 Pesticides pesticide NNS cord-276598-tm0yj2sn 982 35 Synthesis Synthesis NNP cord-276598-tm0yj2sn 982 36 and and CC cord-276598-tm0yj2sn 982 37 insecticidal insecticidal JJ cord-276598-tm0yj2sn 982 38 activity activity NN cord-276598-tm0yj2sn 982 39 of of IN cord-276598-tm0yj2sn 982 40 new new JJ cord-276598-tm0yj2sn 982 41 3-benzylfuran-2-yl 3-benzylfuran-2-yl CD cord-276598-tm0yj2sn 982 42 N N NNP cord-276598-tm0yj2sn 982 43 , , , cord-276598-tm0yj2sn 982 44 N N NNP cord-276598-tm0yj2sn 982 45 , , , cord-276598-tm0yj2sn 982 46 N N NNP cord-276598-tm0yj2sn 982 47 , , , cord-276598-tm0yj2sn 982 48 N n CD cord-276598-tm0yj2sn 982 49 -tetraethyldiamidophosphate -tetraethyldiamidophosphate NN cord-276598-tm0yj2sn 982 50 derivatives derivative NNS cord-276598-tm0yj2sn 982 51 Negatively negatively RB cord-276598-tm0yj2sn 982 52 Correlated Correlated NNP cord-276598-tm0yj2sn 982 53 Cross Cross NNP cord-276598-tm0yj2sn 982 54 - - NN cord-276598-tm0yj2sn 982 55 resistance resistance NN cord-276598-tm0yj2sn 982 56 and and CC cord-276598-tm0yj2sn 982 57 Synergism synergism NN cord-276598-tm0yj2sn 982 58 between between IN cord-276598-tm0yj2sn 982 59 Phosphoramidates Phosphoramidates NNP cord-276598-tm0yj2sn 982 60 and and CC cord-276598-tm0yj2sn 982 61 Phosphorothiolates Phosphorothiolates NNPS cord-276598-tm0yj2sn 982 62 in in IN cord-276598-tm0yj2sn 982 63 Their -PRON- PRP$ cord-276598-tm0yj2sn 982 64 Fungicidal Fungicidal NNP cord-276598-tm0yj2sn 982 65 Actions Actions NNPS cord-276598-tm0yj2sn 982 66 on on IN cord-276598-tm0yj2sn 982 67 Rice Rice NNP cord-276598-tm0yj2sn 982 68 Blast Blast NNP cord-276598-tm0yj2sn 982 69 Fungi Fungi NNP cord-276598-tm0yj2sn 983 1 A a DT cord-276598-tm0yj2sn 983 2 minireview minireview NN cord-276598-tm0yj2sn 983 3 on on IN cord-276598-tm0yj2sn 983 4 what what WP cord-276598-tm0yj2sn 983 5 we -PRON- PRP cord-276598-tm0yj2sn 983 6 have have VBP cord-276598-tm0yj2sn 983 7 learned learn VBN cord-276598-tm0yj2sn 983 8 about about IN cord-276598-tm0yj2sn 983 9 urease urease NN cord-276598-tm0yj2sn 983 10 inhibitors inhibitor NNS cord-276598-tm0yj2sn 983 11 of of IN cord-276598-tm0yj2sn 983 12 agricultural agricultural JJ cord-276598-tm0yj2sn 983 13 interest interest NN cord-276598-tm0yj2sn 983 14 since since IN cord-276598-tm0yj2sn 983 15 mid-2000s mid-2000s NNP cord-276598-tm0yj2sn 983 16 Design Design NNP cord-276598-tm0yj2sn 983 17 , , , cord-276598-tm0yj2sn 983 18 Synthesis Synthesis NNP cord-276598-tm0yj2sn 983 19 , , , cord-276598-tm0yj2sn 983 20 and and CC cord-276598-tm0yj2sn 983 21 Biological Biological NNP cord-276598-tm0yj2sn 983 22 Evaluation Evaluation NNP cord-276598-tm0yj2sn 983 23 of of IN cord-276598-tm0yj2sn 983 24 Phosphoramide Phosphoramide NNP cord-276598-tm0yj2sn 983 25 Derivatives Derivatives NNP cord-276598-tm0yj2sn 983 26 as as IN cord-276598-tm0yj2sn 983 27 Urease Urease NNP cord-276598-tm0yj2sn 983 28 Inhibitors Inhibitors NNP cord-276598-tm0yj2sn 984 1 Recent recent JJ cord-276598-tm0yj2sn 984 2 advances advance NNS cord-276598-tm0yj2sn 984 3 in in IN cord-276598-tm0yj2sn 984 4 design design NN cord-276598-tm0yj2sn 984 5 of of IN cord-276598-tm0yj2sn 984 6 new new JJ cord-276598-tm0yj2sn 984 7 urease urease NN cord-276598-tm0yj2sn 984 8 inhibitors inhibitor NNS cord-276598-tm0yj2sn 984 9 : : : cord-276598-tm0yj2sn 985 1 A a DT cord-276598-tm0yj2sn 985 2 review review NN cord-276598-tm0yj2sn 986 1 A a DT cord-276598-tm0yj2sn 986 2 review review NN cord-276598-tm0yj2sn 986 3 on on IN cord-276598-tm0yj2sn 986 4 the the DT cord-276598-tm0yj2sn 986 5 development development NN cord-276598-tm0yj2sn 986 6 of of IN cord-276598-tm0yj2sn 986 7 urease urease NN cord-276598-tm0yj2sn 986 8 inhibitors inhibitor NNS cord-276598-tm0yj2sn 986 9 as as IN cord-276598-tm0yj2sn 986 10 antimicrobial antimicrobial JJ cord-276598-tm0yj2sn 986 11 agents agent NNS cord-276598-tm0yj2sn 986 12 against against IN cord-276598-tm0yj2sn 986 13 pathogenic pathogenic JJ cord-276598-tm0yj2sn 986 14 bacteria bacteria NNS cord-276598-tm0yj2sn 987 1 The the DT cord-276598-tm0yj2sn 987 2 tribological tribological JJ cord-276598-tm0yj2sn 987 3 study study NN cord-276598-tm0yj2sn 987 4 of of IN cord-276598-tm0yj2sn 987 5 novel novel JJ cord-276598-tm0yj2sn 987 6 phosphorous phosphorous NN cord-276598-tm0yj2sn 987 7 - - HYPH cord-276598-tm0yj2sn 987 8 nitrogen nitrogen NN cord-276598-tm0yj2sn 987 9 type type NN cord-276598-tm0yj2sn 987 10 phosphoramidate phosphoramidate NN cord-276598-tm0yj2sn 987 11 additives additive NNS cord-276598-tm0yj2sn 987 12 in in IN cord-276598-tm0yj2sn 987 13 rapeseed rapeseed NN cord-276598-tm0yj2sn 987 14 oil oil NN cord-276598-tm0yj2sn 987 15 Halogenated halogenate VBN cord-276598-tm0yj2sn 987 16 flame flame NN cord-276598-tm0yj2sn 987 17 retardants retardant NNS cord-276598-tm0yj2sn 987 18 : : : cord-276598-tm0yj2sn 987 19 Do do VB cord-276598-tm0yj2sn 987 20 the the DT cord-276598-tm0yj2sn 987 21 fire fire NN cord-276598-tm0yj2sn 987 22 safety safety NN cord-276598-tm0yj2sn 987 23 benefits benefit NNS cord-276598-tm0yj2sn 987 24 justify justify VBP cord-276598-tm0yj2sn 987 25 the the DT cord-276598-tm0yj2sn 987 26 risks risk NNS cord-276598-tm0yj2sn 987 27 ? ? . cord-276598-tm0yj2sn 988 1 Thermal thermal JJ cord-276598-tm0yj2sn 988 2 degradation degradation NN cord-276598-tm0yj2sn 988 3 of of IN cord-276598-tm0yj2sn 988 4 cellulose cellulose NN cord-276598-tm0yj2sn 988 5 acetate acetate NN cord-276598-tm0yj2sn 988 6 in in IN cord-276598-tm0yj2sn 988 7 presence presence NN cord-276598-tm0yj2sn 988 8 of of IN cord-276598-tm0yj2sn 988 9 bis bis NNP cord-276598-tm0yj2sn 988 10 - - HYPH cord-276598-tm0yj2sn 988 11 phosphoramidates phosphoramidates JJ cord-276598-tm0yj2sn 988 12 Multiparameter Multiparameter NNP cord-276598-tm0yj2sn 988 13 toxicity toxicity NN cord-276598-tm0yj2sn 988 14 assessment assessment NN cord-276598-tm0yj2sn 988 15 of of IN cord-276598-tm0yj2sn 988 16 novel novel JJ cord-276598-tm0yj2sn 988 17 DOPO DOPO NNP cord-276598-tm0yj2sn 988 18 - - HYPH cord-276598-tm0yj2sn 988 19 derived derive VBN cord-276598-tm0yj2sn 988 20 organophosphorus organophosphorus JJ cord-276598-tm0yj2sn 988 21 flame flame NN cord-276598-tm0yj2sn 988 22 retardants retardant NNS cord-276598-tm0yj2sn 989 1 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 989 2 - - HYPH cord-276598-tm0yj2sn 989 3 Containing contain VBG cord-276598-tm0yj2sn 989 4 Flame Flame NNP cord-276598-tm0yj2sn 989 5 - - HYPH cord-276598-tm0yj2sn 989 6 Retardant Retardant NNP cord-276598-tm0yj2sn 989 7 Flexible Flexible NNP cord-276598-tm0yj2sn 989 8 Polyurethane Polyurethane NNP cord-276598-tm0yj2sn 990 1 Foams Foams NNP cord-276598-tm0yj2sn 990 2 Recent Recent NNP cord-276598-tm0yj2sn 990 3 Advances Advances NNPS cord-276598-tm0yj2sn 990 4 for for IN cord-276598-tm0yj2sn 990 5 Flame Flame NNP cord-276598-tm0yj2sn 990 6 Retardancy Retardancy NNP cord-276598-tm0yj2sn 990 7 of of IN cord-276598-tm0yj2sn 990 8 Textiles Textiles NNPS cord-276598-tm0yj2sn 990 9 Based base VBN cord-276598-tm0yj2sn 990 10 on on IN cord-276598-tm0yj2sn 990 11 Phosphorus Phosphorus NNP cord-276598-tm0yj2sn 991 1 Chemistry Chemistry NNP cord-276598-tm0yj2sn 991 2 Microwave Microwave NNP cord-276598-tm0yj2sn 991 3 Assisted Assisted NNP cord-276598-tm0yj2sn 991 4 Preparation Preparation NNP cord-276598-tm0yj2sn 991 5 of of IN cord-276598-tm0yj2sn 991 6 Self Self NNP cord-276598-tm0yj2sn 991 7 - - HYPH cord-276598-tm0yj2sn 991 8 Extinguishing extinguish VBG cord-276598-tm0yj2sn 991 9 Cotton Cotton NNP cord-276598-tm0yj2sn 991 10 Fabrics Fabrics NNPS cord-276598-tm0yj2sn 991 11 by by IN cord-276598-tm0yj2sn 991 12 Small Small NNP cord-276598-tm0yj2sn 991 13 Molecules Molecules NNPS cord-276598-tm0yj2sn 991 14 Containing contain VBG cord-276598-tm0yj2sn 991 15 Phosphorous Phosphorous NNP cord-276598-tm0yj2sn 991 16 and and CC cord-276598-tm0yj2sn 991 17 Nitrogen Nitrogen NNP cord-276598-tm0yj2sn 991 18 Molecular Molecular NNP cord-276598-tm0yj2sn 991 19 Firefighting Firefighting NNP cord-276598-tm0yj2sn 992 1 -How -How : cord-276598-tm0yj2sn 992 2 Modern modern JJ cord-276598-tm0yj2sn 992 3 Phosphorus phosphorus NN cord-276598-tm0yj2sn 992 4 Chemistry Chemistry NNP cord-276598-tm0yj2sn 992 5 Can Can MD cord-276598-tm0yj2sn 992 6 Help help VB cord-276598-tm0yj2sn 992 7 Solve solve VB cord-276598-tm0yj2sn 992 8 the the DT cord-276598-tm0yj2sn 992 9 Challenge Challenge NNP cord-276598-tm0yj2sn 992 10 of of IN cord-276598-tm0yj2sn 992 11 Flame Flame NNP cord-276598-tm0yj2sn 992 12 Retardancy Retardancy NNP cord-276598-tm0yj2sn 992 13 El El NNP cord-276598-tm0yj2sn 992 14 - - HYPH cord-276598-tm0yj2sn 992 15 Shafei Shafei NNP cord-276598-tm0yj2sn 992 16 , , , cord-276598-tm0yj2sn 992 17 A. A. NNP cord-276598-tm0yj2sn 992 18 Preparation Preparation NNP cord-276598-tm0yj2sn 992 19 , , , cord-276598-tm0yj2sn 992 20 Polymerization Polymerization NNP cord-276598-tm0yj2sn 992 21 , , , cord-276598-tm0yj2sn 992 22 and and CC cord-276598-tm0yj2sn 992 23 Performance Performance NNP cord-276598-tm0yj2sn 992 24 Evaluation Evaluation NNP cord-276598-tm0yj2sn 992 25 of of IN cord-276598-tm0yj2sn 992 26 Halogen Halogen NNP cord-276598-tm0yj2sn 992 27 - - HYPH cord-276598-tm0yj2sn 992 28 Free Free NNP cord-276598-tm0yj2sn 992 29 Radiation Radiation NNP cord-276598-tm0yj2sn 992 30 Curable Curable NNP cord-276598-tm0yj2sn 992 31 Flame Flame NNP cord-276598-tm0yj2sn 992 32 Retardant Retardant NNP cord-276598-tm0yj2sn 992 33 Monomers Monomers NNPS cord-276598-tm0yj2sn 992 34 for for IN cord-276598-tm0yj2sn 992 35 Cotton cotton NN cord-276598-tm0yj2sn 992 36 Substrates Substrates NNPS cord-276598-tm0yj2sn 992 37 Systematically systematically RB cord-276598-tm0yj2sn 992 38 Controlled control VBN cord-276598-tm0yj2sn 992 39 Decomposition Decomposition NNP cord-276598-tm0yj2sn 992 40 Mechanism Mechanism NNP cord-276598-tm0yj2sn 992 41 in in IN cord-276598-tm0yj2sn 992 42 Phosphorus Phosphorus NNP cord-276598-tm0yj2sn 992 43 Flame Flame NNP cord-276598-tm0yj2sn 992 44 Retardants Retardants NNPS cord-276598-tm0yj2sn 992 45 by by IN cord-276598-tm0yj2sn 992 46 Precise Precise NNP cord-276598-tm0yj2sn 992 47 Molecular Molecular NNP cord-276598-tm0yj2sn 992 48 Architecture Architecture NNP cord-276598-tm0yj2sn 992 49 : : : cord-276598-tm0yj2sn 993 1 P p NN cord-276598-tm0yj2sn 993 2 - - HYPH cord-276598-tm0yj2sn 993 3 O o NN cord-276598-tm0yj2sn 994 1 vs vs IN cord-276598-tm0yj2sn 994 2 P P NNP cord-276598-tm0yj2sn 994 3 - - HYPH cord-276598-tm0yj2sn 994 4 N N NNP cord-276598-tm0yj2sn 994 5 Characterization characterization NN cord-276598-tm0yj2sn 994 6 of of IN cord-276598-tm0yj2sn 994 7 chars char NNS cord-276598-tm0yj2sn 994 8 obtained obtain VBN cord-276598-tm0yj2sn 994 9 from from IN cord-276598-tm0yj2sn 994 10 cellulose cellulose NN cord-276598-tm0yj2sn 994 11 treated treat VBN cord-276598-tm0yj2sn 994 12 with with IN cord-276598-tm0yj2sn 994 13 phosphoramidate phosphoramidate NN cord-276598-tm0yj2sn 994 14 flame flame NN cord-276598-tm0yj2sn 994 15 retardants retardant NNS cord-276598-tm0yj2sn 994 16 Novel novel JJ cord-276598-tm0yj2sn 994 17 intumescent intumescent NN cord-276598-tm0yj2sn 994 18 flame flame NN cord-276598-tm0yj2sn 994 19 retardants retardant NNS cord-276598-tm0yj2sn 994 20 : : : cord-276598-tm0yj2sn 994 21 Synthesis synthesis NN cord-276598-tm0yj2sn 994 22 and and CC cord-276598-tm0yj2sn 994 23 application application NN cord-276598-tm0yj2sn 994 24 in in IN cord-276598-tm0yj2sn 994 25 polycarbonate polycarbonate NNP cord-276598-tm0yj2sn 994 26 A a DT cord-276598-tm0yj2sn 994 27 Method Method NNP cord-276598-tm0yj2sn 994 28 for for IN cord-276598-tm0yj2sn 994 29 the the DT cord-276598-tm0yj2sn 994 30 Analysis Analysis NNP cord-276598-tm0yj2sn 994 31 of of IN cord-276598-tm0yj2sn 994 32 Low Low NNP cord-276598-tm0yj2sn 994 33 - - HYPH cord-276598-tm0yj2sn 994 34 Mass Mass NNP cord-276598-tm0yj2sn 994 35 Molecules Molecules NNPS cord-276598-tm0yj2sn 994 36 by by IN cord-276598-tm0yj2sn 994 37 MALDI MALDI NNP cord-276598-tm0yj2sn 994 38 - - HYPH cord-276598-tm0yj2sn 994 39 TOF TOF NNP cord-276598-tm0yj2sn 994 40 Mass Mass NNP cord-276598-tm0yj2sn 994 41 Spectrometry Spectrometry NNP cord-276598-tm0yj2sn 994 42 Suppression Suppression NNP cord-276598-tm0yj2sn 994 43 of of IN cord-276598-tm0yj2sn 994 44 matrix matrix NN cord-276598-tm0yj2sn 994 45 ions ion NNS cord-276598-tm0yj2sn 994 46 by by IN cord-276598-tm0yj2sn 994 47 N n NN cord-276598-tm0yj2sn 994 48 - - HYPH cord-276598-tm0yj2sn 994 49 phosphorylation phosphorylation NN cord-276598-tm0yj2sn 994 50 labeling labeling NN cord-276598-tm0yj2sn 994 51 using use VBG cord-276598-tm0yj2sn 994 52 matrix matrix NN cord-276598-tm0yj2sn 994 53 - - HYPH cord-276598-tm0yj2sn 994 54 assisted assist VBN cord-276598-tm0yj2sn 994 55 laser laser NN cord-276598-tm0yj2sn 994 56 desorption desorption NN cord-276598-tm0yj2sn 994 57 - - HYPH cord-276598-tm0yj2sn 994 58 ionization ionization NN cord-276598-tm0yj2sn 994 59 time time NN cord-276598-tm0yj2sn 994 60 - - HYPH cord-276598-tm0yj2sn 994 61 of of IN cord-276598-tm0yj2sn 994 62 - - HYPH cord-276598-tm0yj2sn 994 63 flight flight NN cord-276598-tm0yj2sn 994 64 mass mass NN cord-276598-tm0yj2sn 994 65 spectrometry spectrometry NN cord-276598-tm0yj2sn 994 66 Selective Selective NNP cord-276598-tm0yj2sn 994 67 Liquid Liquid NNP cord-276598-tm0yj2sn 994 68 - - HYPH cord-276598-tm0yj2sn 994 69 Liquid liquid NN cord-276598-tm0yj2sn 994 70 Extraction extraction NN cord-276598-tm0yj2sn 994 71 of of IN cord-276598-tm0yj2sn 994 72 Uranium Uranium NNP cord-276598-tm0yj2sn 994 73 by by IN cord-276598-tm0yj2sn 994 74 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 994 75 - - HYPH cord-276598-tm0yj2sn 994 76 Group Group NNP cord-276598-tm0yj2sn 994 77 Bearing Bearing NNP cord-276598-tm0yj2sn 994 78 Ionic Ionic NNP cord-276598-tm0yj2sn 994 79 Liquid Liquid NNP cord-276598-tm0yj2sn 994 80 Selective selective JJ cord-276598-tm0yj2sn 994 81 Micellar micellar JJ cord-276598-tm0yj2sn 994 82 Extraction extraction NN cord-276598-tm0yj2sn 994 83 of of IN cord-276598-tm0yj2sn 994 84 Ultratrace Ultratrace NNP cord-276598-tm0yj2sn 994 85 Levels Levels NNP cord-276598-tm0yj2sn 994 86 of of IN cord-276598-tm0yj2sn 994 87 Uranium Uranium NNP cord-276598-tm0yj2sn 994 88 in in IN cord-276598-tm0yj2sn 994 89 Aqueous Aqueous NNP cord-276598-tm0yj2sn 994 90 Samples Samples NNPS cord-276598-tm0yj2sn 994 91 by by IN cord-276598-tm0yj2sn 994 92 Task Task NNP cord-276598-tm0yj2sn 994 93 Specific specific JJ cord-276598-tm0yj2sn 994 94 Ionic Ionic NNP cord-276598-tm0yj2sn 994 95 Liquid Liquid NNP cord-276598-tm0yj2sn 994 96 Followed follow VBN cord-276598-tm0yj2sn 994 97 by by IN cord-276598-tm0yj2sn 994 98 Its -PRON- PRP$ cord-276598-tm0yj2sn 994 99 Detection detection NN cord-276598-tm0yj2sn 994 100 Employing employ VBG cord-276598-tm0yj2sn 994 101 Total total JJ cord-276598-tm0yj2sn 994 102 Reflection Reflection NNP cord-276598-tm0yj2sn 994 103 X x NN cord-276598-tm0yj2sn 994 104 - - NN cord-276598-tm0yj2sn 994 105 ray ray NN cord-276598-tm0yj2sn 994 106 Fluorescence fluorescence NN cord-276598-tm0yj2sn 994 107 Spectrometry Spectrometry NNP cord-276598-tm0yj2sn 994 108 C(sp3)-H c(sp3)-h NN cord-276598-tm0yj2sn 994 109 Bond Bond NNP cord-276598-tm0yj2sn 994 110 Activation activation NN cord-276598-tm0yj2sn 994 111 Induced induce VBN cord-276598-tm0yj2sn 994 112 by by IN cord-276598-tm0yj2sn 994 113 Monohydroborane Monohydroborane NNP cord-276598-tm0yj2sn 994 114 Coordination Coordination NNP cord-276598-tm0yj2sn 994 115 at at IN cord-276598-tm0yj2sn 994 116 an an DT cord-276598-tm0yj2sn 994 117 Iridium(III)-Phosphoramidate iridium(iii)-phosphoramidate NN cord-276598-tm0yj2sn 994 118 Complex Complex NNP cord-276598-tm0yj2sn 994 119 Toward toward IN cord-276598-tm0yj2sn 994 120 anti anti JJ cord-276598-tm0yj2sn 994 121 - - JJ cord-276598-tm0yj2sn 994 122 Markovnikov markovnikov JJ cord-276598-tm0yj2sn 994 123 1-Alkyne 1-Alkyne NNP cord-276598-tm0yj2sn 994 124 O O NNP cord-276598-tm0yj2sn 994 125 - - HYPH cord-276598-tm0yj2sn 994 126 Phosphoramidation phosphoramidation NN cord-276598-tm0yj2sn 994 127 : : : cord-276598-tm0yj2sn 995 1 Exploiting exploit VBG cord-276598-tm0yj2sn 995 2 Metal Metal NNP cord-276598-tm0yj2sn 995 3 - - HYPH cord-276598-tm0yj2sn 995 4 Ligand Ligand NNP cord-276598-tm0yj2sn 995 5 Cooperativity Cooperativity NNP cord-276598-tm0yj2sn 995 6 in in IN cord-276598-tm0yj2sn 995 7 a a DT cord-276598-tm0yj2sn 995 8 1,3-N 1,3-n CD cord-276598-tm0yj2sn 995 9 , , , cord-276598-tm0yj2sn 995 10 O o UH cord-276598-tm0yj2sn 995 11 - - HYPH cord-276598-tm0yj2sn 995 12 Chelated chelated JJ cord-276598-tm0yj2sn 995 13 Cp*Ir(III Cp*Ir(III NNS cord-276598-tm0yj2sn 995 14 ) ) -RRB- cord-276598-tm0yj2sn 996 1 Complex complex JJ cord-276598-tm0yj2sn 996 2 1,3-N 1,3-n CD cord-276598-tm0yj2sn 996 3 , , , cord-276598-tm0yj2sn 996 4 O O NNP cord-276598-tm0yj2sn 996 5 - - HYPH cord-276598-tm0yj2sn 996 6 Complexes Complexes NNPS cord-276598-tm0yj2sn 996 7 of of IN cord-276598-tm0yj2sn 996 8 late late JJ cord-276598-tm0yj2sn 996 9 transition transition NN cord-276598-tm0yj2sn 996 10 metals metal NNS cord-276598-tm0yj2sn 996 11 . . . cord-276598-tm0yj2sn 997 1 Ligands ligand NNS cord-276598-tm0yj2sn 997 2 with with IN cord-276598-tm0yj2sn 997 3 flexible flexible JJ cord-276598-tm0yj2sn 997 4 bonding bonding NN cord-276598-tm0yj2sn 997 5 modes mode NNS cord-276598-tm0yj2sn 997 6 and and CC cord-276598-tm0yj2sn 997 7 reaction reaction NN cord-276598-tm0yj2sn 997 8 profiles profile NNS cord-276598-tm0yj2sn 997 9 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 997 10 tantalum tantalum NN cord-276598-tm0yj2sn 997 11 complexes complex NNS cord-276598-tm0yj2sn 997 12 for for IN cord-276598-tm0yj2sn 997 13 room room NN cord-276598-tm0yj2sn 997 14 - - HYPH cord-276598-tm0yj2sn 997 15 temperature temperature NN cord-276598-tm0yj2sn 997 16 C c NN cord-276598-tm0yj2sn 997 17 - - HYPH cord-276598-tm0yj2sn 997 18 H h NN cord-276598-tm0yj2sn 997 19 functionalization functionalization NN cord-276598-tm0yj2sn 997 20 : : : cord-276598-tm0yj2sn 998 1 Hydroaminoalkylation Hydroaminoalkylation NNP cord-276598-tm0yj2sn 998 2 catalysis catalysis NN cord-276598-tm0yj2sn 998 3 Copper Copper NNP cord-276598-tm0yj2sn 998 4 - - HYPH cord-276598-tm0yj2sn 998 5 Catalyzed Catalyzed NNP cord-276598-tm0yj2sn 998 6 Synthesis Synthesis NNP cord-276598-tm0yj2sn 998 7 of of IN cord-276598-tm0yj2sn 998 8 Medium Medium NNP cord-276598-tm0yj2sn 998 9 - - : cord-276598-tm0yj2sn 998 10 and and CC cord-276598-tm0yj2sn 998 11 Large large JJ cord-276598-tm0yj2sn 998 12 - - HYPH cord-276598-tm0yj2sn 998 13 Sized Sized NNP cord-276598-tm0yj2sn 998 14 Nitrogen Nitrogen NNP cord-276598-tm0yj2sn 998 15 Heterocycles Heterocycles NNP cord-276598-tm0yj2sn 998 16 via via IN cord-276598-tm0yj2sn 998 17 N n CD cord-276598-tm0yj2sn 998 18 - - HYPH cord-276598-tm0yj2sn 998 19 Arylation Arylation NNP cord-276598-tm0yj2sn 998 20 of of IN cord-276598-tm0yj2sn 998 21 Phosphoramidates Phosphoramidates NNPS cord-276598-tm0yj2sn 998 22 and and CC cord-276598-tm0yj2sn 998 23 Carbamates Carbamates NNP cord-276598-tm0yj2sn 998 24 Palladium Palladium NNP cord-276598-tm0yj2sn 998 25 - - HYPH cord-276598-tm0yj2sn 998 26 Catalyzed Catalyzed NNP cord-276598-tm0yj2sn 998 27 C C NNP cord-276598-tm0yj2sn 998 28 - - HYPH cord-276598-tm0yj2sn 998 29 H H NNP cord-276598-tm0yj2sn 998 30 Arylation Arylation NNP cord-276598-tm0yj2sn 998 31 Using use VBG cord-276598-tm0yj2sn 998 32 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 998 33 as as IN cord-276598-tm0yj2sn 998 34 a a DT cord-276598-tm0yj2sn 998 35 Directing Directing NNP cord-276598-tm0yj2sn 998 36 Group Group NNP cord-276598-tm0yj2sn 998 37 at at IN cord-276598-tm0yj2sn 998 38 Room room NN cord-276598-tm0yj2sn 998 39 Temperature Temperature NNP cord-276598-tm0yj2sn 999 1 2-(Benzo[d]thiazol-2-yl 2-(benzo[d]thiazol-2-yl LS cord-276598-tm0yj2sn 999 2 ) ) -RRB- cord-276598-tm0yj2sn 1000 1 phenyl-4-nitrophenyl phenyl-4-nitrophenyl NNP cord-276598-tm0yj2sn 1000 2 alkyl alkyl NNP cord-276598-tm0yj2sn 1000 3 / / SYM cord-276598-tm0yj2sn 1000 4 aryl aryl NN cord-276598-tm0yj2sn 1000 5 substituted substitute VBN cord-276598-tm0yj2sn 1000 6 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 1000 7 : : : cord-276598-tm0yj2sn 1001 1 Synthesis synthesis NN cord-276598-tm0yj2sn 1001 2 , , , cord-276598-tm0yj2sn 1001 3 characterization characterization NN cord-276598-tm0yj2sn 1001 4 and and CC cord-276598-tm0yj2sn 1001 5 antimicrobial antimicrobial JJ cord-276598-tm0yj2sn 1001 6 activity activity NN cord-276598-tm0yj2sn 1001 7 evaluation evaluation NN cord-276598-tm0yj2sn 1001 8 Synthesis synthesis NN cord-276598-tm0yj2sn 1001 9 and and CC cord-276598-tm0yj2sn 1001 10 biological biological JJ cord-276598-tm0yj2sn 1001 11 evaluation evaluation NN cord-276598-tm0yj2sn 1001 12 of of IN cord-276598-tm0yj2sn 1001 13 novel novel JJ cord-276598-tm0yj2sn 1001 14 phosphoramidate phosphoramidate NN cord-276598-tm0yj2sn 1001 15 derivatives derivative NNS cord-276598-tm0yj2sn 1001 16 of of IN cord-276598-tm0yj2sn 1001 17 coumarin coumarin NN cord-276598-tm0yj2sn 1001 18 as as IN cord-276598-tm0yj2sn 1001 19 chitin chitin NN cord-276598-tm0yj2sn 1001 20 synthase synthase NN cord-276598-tm0yj2sn 1001 21 inhibitors inhibitor NNS cord-276598-tm0yj2sn 1001 22 and and CC cord-276598-tm0yj2sn 1001 23 antifungal antifungal JJ cord-276598-tm0yj2sn 1001 24 agents agent NNS cord-276598-tm0yj2sn 1002 1 Convenient convenient JJ cord-276598-tm0yj2sn 1002 2 one one CD cord-276598-tm0yj2sn 1002 3 - - HYPH cord-276598-tm0yj2sn 1002 4 pot pot NN cord-276598-tm0yj2sn 1002 5 synthesis synthesis NN cord-276598-tm0yj2sn 1002 6 and and CC cord-276598-tm0yj2sn 1002 7 biological biological JJ cord-276598-tm0yj2sn 1002 8 evaluation evaluation NN cord-276598-tm0yj2sn 1002 9 of of IN cord-276598-tm0yj2sn 1002 10 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 1002 11 and and CC cord-276598-tm0yj2sn 1002 12 phosphonates phosphonates NNP cord-276598-tm0yj2sn 1002 13 containing contain VBG cord-276598-tm0yj2sn 1002 14 heterocycles heterocycles NNP cord-276598-tm0yj2sn 1002 15 Synthesis Synthesis NNP cord-276598-tm0yj2sn 1002 16 , , , cord-276598-tm0yj2sn 1002 17 spectral spectral JJ cord-276598-tm0yj2sn 1002 18 characterization characterization NN cord-276598-tm0yj2sn 1002 19 , , , cord-276598-tm0yj2sn 1002 20 and and CC cord-276598-tm0yj2sn 1002 21 proand proand NN cord-276598-tm0yj2sn 1002 22 antioxidant antioxidant JJ cord-276598-tm0yj2sn 1002 23 activity activity NN cord-276598-tm0yj2sn 1002 24 of of IN cord-276598-tm0yj2sn 1002 25 phosphorylated phosphorylated JJ cord-276598-tm0yj2sn 1002 26 derivatives derivative NNS cord-276598-tm0yj2sn 1002 27 of of IN cord-276598-tm0yj2sn 1002 28 cis cis NNP cord-276598-tm0yj2sn 1002 29 - - HYPH cord-276598-tm0yj2sn 1002 30 tramadol tramadol NNP cord-276598-tm0yj2sn 1002 31 . . . cord-276598-tm0yj2sn 1003 1 Phosphorus Phosphorus NNP cord-276598-tm0yj2sn 1003 2 Sulfur Sulfur NNP cord-276598-tm0yj2sn 1003 3 Silicon Silicon NNP cord-276598-tm0yj2sn 1004 1 Relat Relat NNP cord-276598-tm0yj2sn 1004 2 Anti Anti NNP cord-276598-tm0yj2sn 1004 3 - - JJ cord-276598-tm0yj2sn 1004 4 cancer cancer NN cord-276598-tm0yj2sn 1005 1 ProTides ProTides NNPS cord-276598-tm0yj2sn 1005 2 : : : cord-276598-tm0yj2sn 1006 1 Tuning tune VBG cord-276598-tm0yj2sn 1006 2 the the DT cord-276598-tm0yj2sn 1006 3 activity activity NN cord-276598-tm0yj2sn 1006 4 of of IN cord-276598-tm0yj2sn 1006 5 BVDU BVDU NNP cord-276598-tm0yj2sn 1006 6 phosphoramidates phosphoramidates NN cord-276598-tm0yj2sn 1006 7 related relate VBN cord-276598-tm0yj2sn 1006 8 to to IN cord-276598-tm0yj2sn 1006 9 thymectacin thymectacin NNP cord-276598-tm0yj2sn 1006 10 Synthesis Synthesis NNP cord-276598-tm0yj2sn 1006 11 and and CC cord-276598-tm0yj2sn 1006 12 evaluation evaluation NN cord-276598-tm0yj2sn 1006 13 of of IN cord-276598-tm0yj2sn 1006 14 phosphoramidate phosphoramidate NNP cord-276598-tm0yj2sn 1006 15 and and CC cord-276598-tm0yj2sn 1006 16 phosphorothioamidate phosphorothioamidate NNP cord-276598-tm0yj2sn 1006 17 analogues analogue NNS cord-276598-tm0yj2sn 1006 18 of of IN cord-276598-tm0yj2sn 1006 19 amiprophos amiprophos NN cord-276598-tm0yj2sn 1006 20 methyl methyl NN cord-276598-tm0yj2sn 1006 21 as as IN cord-276598-tm0yj2sn 1006 22 potential potential JJ cord-276598-tm0yj2sn 1006 23 antimalarial antimalarial JJ cord-276598-tm0yj2sn 1006 24 agents agent NNS cord-276598-tm0yj2sn 1006 25 Phosphoramidates Phosphoramidates NNPS cord-276598-tm0yj2sn 1006 26 and and CC cord-276598-tm0yj2sn 1006 27 phosphonamidates phosphonamidates NNP cord-276598-tm0yj2sn 1006 28 ( ( -LRB- cord-276598-tm0yj2sn 1006 29 ProTides ProTides NNP cord-276598-tm0yj2sn 1006 30 ) ) -RRB- cord-276598-tm0yj2sn 1006 31 with with IN cord-276598-tm0yj2sn 1006 32 antiviral antiviral JJ cord-276598-tm0yj2sn 1006 33 activity activity NN cord-276598-tm0yj2sn 1006 34 Anchimerically Anchimerically NNP cord-276598-tm0yj2sn 1007 1 Activatable Activatable NNP cord-276598-tm0yj2sn 1007 2 Antiviral Antiviral NNP cord-276598-tm0yj2sn 1008 1 ProTides ProTides NNPS cord-276598-tm0yj2sn 1008 2 New New NNP cord-276598-tm0yj2sn 1008 3 and and CC cord-276598-tm0yj2sn 1008 4 Efficient efficient JJ cord-276598-tm0yj2sn 1008 5 Approach Approach NNP cord-276598-tm0yj2sn 1008 6 to to IN cord-276598-tm0yj2sn 1008 7 Aryl Aryl NNP cord-276598-tm0yj2sn 1008 8 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 1008 9 Derivatives Derivatives NNPS cord-276598-tm0yj2sn 1008 10 of of IN cord-276598-tm0yj2sn 1008 11 AZT AZT NNP cord-276598-tm0yj2sn 1008 12 / / SYM cord-276598-tm0yj2sn 1008 13 d4 d4 NNP cord-276598-tm0yj2sn 1008 14 T T NNP cord-276598-tm0yj2sn 1008 15 as as IN cord-276598-tm0yj2sn 1008 16 Anti Anti NNP cord-276598-tm0yj2sn 1008 17 - - JJ cord-276598-tm0yj2sn 1008 18 HIV HIV NNP cord-276598-tm0yj2sn 1009 1 Prodrugs Prodrugs NNP cord-276598-tm0yj2sn 1009 2 Aryloxy Aryloxy NNP cord-276598-tm0yj2sn 1009 3 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 1009 4 Triesters Triesters NNPS cord-276598-tm0yj2sn 1009 5 : : : cord-276598-tm0yj2sn 1009 6 A a DT cord-276598-tm0yj2sn 1009 7 Technology technology NN cord-276598-tm0yj2sn 1009 8 for for IN cord-276598-tm0yj2sn 1009 9 Delivering deliver VBG cord-276598-tm0yj2sn 1009 10 Monophosphorylated Monophosphorylated NNP cord-276598-tm0yj2sn 1009 11 Nucleosides Nucleosides NNP cord-276598-tm0yj2sn 1009 12 and and CC cord-276598-tm0yj2sn 1009 13 Sugars sugar NNS cord-276598-tm0yj2sn 1009 14 into into IN cord-276598-tm0yj2sn 1009 15 Cells cell NNS cord-276598-tm0yj2sn 1010 1 The the DT cord-276598-tm0yj2sn 1010 2 ProTide ProTide NNP cord-276598-tm0yj2sn 1010 3 Prodrug Prodrug NNP cord-276598-tm0yj2sn 1010 4 Technology Technology NNP cord-276598-tm0yj2sn 1010 5 : : : cord-276598-tm0yj2sn 1010 6 From from IN cord-276598-tm0yj2sn 1010 7 the the DT cord-276598-tm0yj2sn 1010 8 Concept Concept NNP cord-276598-tm0yj2sn 1010 9 to to IN cord-276598-tm0yj2sn 1010 10 the the DT cord-276598-tm0yj2sn 1010 11 Clinic Clinic NNP cord-276598-tm0yj2sn 1010 12 Current current JJ cord-276598-tm0yj2sn 1010 13 knowledge knowledge NN cord-276598-tm0yj2sn 1010 14 about about IN cord-276598-tm0yj2sn 1010 15 the the DT cord-276598-tm0yj2sn 1010 16 antivirals antiviral NNS cord-276598-tm0yj2sn 1010 17 remdesivir remdesivir NNP cord-276598-tm0yj2sn 1010 18 ( ( -LRB- cord-276598-tm0yj2sn 1010 19 GS-5734 GS-5734 NNP cord-276598-tm0yj2sn 1010 20 ) ) -RRB- cord-276598-tm0yj2sn 1011 1 and and CC cord-276598-tm0yj2sn 1011 2 GS-441524 GS-441524 NNP cord-276598-tm0yj2sn 1011 3 as as IN cord-276598-tm0yj2sn 1011 4 therapeutic therapeutic JJ cord-276598-tm0yj2sn 1011 5 options option NNS cord-276598-tm0yj2sn 1011 6 for for IN cord-276598-tm0yj2sn 1011 7 coronaviruses coronaviruse NNS cord-276598-tm0yj2sn 1011 8 . . . cord-276598-tm0yj2sn 1012 1 One one CD cord-276598-tm0yj2sn 1012 2 Health Health NNP cord-276598-tm0yj2sn 1012 3 Polyphosphoramidate Polyphosphoramidate NNP cord-276598-tm0yj2sn 1012 4 gene gene NN cord-276598-tm0yj2sn 1012 5 carriers carrier NNS cord-276598-tm0yj2sn 1012 6 : : : cord-276598-tm0yj2sn 1012 7 Effect effect NN cord-276598-tm0yj2sn 1012 8 of of IN cord-276598-tm0yj2sn 1012 9 charge charge NN cord-276598-tm0yj2sn 1012 10 group group NN cord-276598-tm0yj2sn 1012 11 on on IN cord-276598-tm0yj2sn 1012 12 gene gene NN cord-276598-tm0yj2sn 1012 13 transfer transfer NN cord-276598-tm0yj2sn 1012 14 efficiency efficiency NN cord-276598-tm0yj2sn 1012 15 Ternary Ternary NNP cord-276598-tm0yj2sn 1012 16 Complexes Complexes NNPS cord-276598-tm0yj2sn 1013 1 Comprising comprise VBG cord-276598-tm0yj2sn 1013 2 Polyphosphoramidate Polyphosphoramidate NNP cord-276598-tm0yj2sn 1013 3 Gene Gene NNP cord-276598-tm0yj2sn 1013 4 Carriers Carriers NNP cord-276598-tm0yj2sn 1013 5 with with IN cord-276598-tm0yj2sn 1013 6 Different different JJ cord-276598-tm0yj2sn 1013 7 Types type NNS cord-276598-tm0yj2sn 1013 8 of of IN cord-276598-tm0yj2sn 1013 9 Charge Charge NNP cord-276598-tm0yj2sn 1013 10 Groups Groups NNPS cord-276598-tm0yj2sn 1014 1 Improve improve VB cord-276598-tm0yj2sn 1014 2 Transfection Transfection NNP cord-276598-tm0yj2sn 1014 3 Efficiency Efficiency NNP cord-276598-tm0yj2sn 1014 4 Discovery Discovery NNP cord-276598-tm0yj2sn 1014 5 and and CC cord-276598-tm0yj2sn 1014 6 Synthesis Synthesis NNP cord-276598-tm0yj2sn 1014 7 of of IN cord-276598-tm0yj2sn 1014 8 a a DT cord-276598-tm0yj2sn 1014 9 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 1014 10 Prodrug Prodrug NNP cord-276598-tm0yj2sn 1014 11 of of IN cord-276598-tm0yj2sn 1014 12 a a DT cord-276598-tm0yj2sn 1014 13 Pyrrolo Pyrrolo NNP cord-276598-tm0yj2sn 1014 14 GS-5734 GS-5734 NNS cord-276598-tm0yj2sn 1014 15 ) ) -RRB- cord-276598-tm0yj2sn 1015 1 for for IN cord-276598-tm0yj2sn 1015 2 the the DT cord-276598-tm0yj2sn 1015 3 Treatment Treatment NNP cord-276598-tm0yj2sn 1015 4 of of IN cord-276598-tm0yj2sn 1015 5 Ebola Ebola NNP cord-276598-tm0yj2sn 1015 6 and and CC cord-276598-tm0yj2sn 1015 7 Emerging Emerging NNP cord-276598-tm0yj2sn 1015 8 Viruses Viruses NNPS cord-276598-tm0yj2sn 1015 9 Structure structure NN cord-276598-tm0yj2sn 1015 10 - - HYPH cord-276598-tm0yj2sn 1015 11 reactivity reactivity NN cord-276598-tm0yj2sn 1015 12 correlation correlation NN cord-276598-tm0yj2sn 1015 13 for for IN cord-276598-tm0yj2sn 1015 14 the the DT cord-276598-tm0yj2sn 1015 15 hydrolysis hydrolysis NN cord-276598-tm0yj2sn 1015 16 of of IN cord-276598-tm0yj2sn 1015 17 phosphoramidate phosphoramidate NN cord-276598-tm0yj2sn 1015 18 monoanions monoanion NNS cord-276598-tm0yj2sn 1015 19 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 1015 20 solvolysis solvolysis NN cord-276598-tm0yj2sn 1015 21 Tunable Tunable NNP cord-276598-tm0yj2sn 1015 22 pH pH NNP cord-276598-tm0yj2sn 1015 23 - - HYPH cord-276598-tm0yj2sn 1015 24 Sensitive sensitive JJ cord-276598-tm0yj2sn 1015 25 Linker Linker NNP cord-276598-tm0yj2sn 1015 26 for for IN cord-276598-tm0yj2sn 1015 27 Controlled Controlled NNP cord-276598-tm0yj2sn 1015 28 Release Release NNP cord-276598-tm0yj2sn 1015 29 Second Second NNP cord-276598-tm0yj2sn 1015 30 - - HYPH cord-276598-tm0yj2sn 1015 31 Generation generation NN cord-276598-tm0yj2sn 1015 32 Tunable Tunable NNP cord-276598-tm0yj2sn 1015 33 pH ph NN cord-276598-tm0yj2sn 1015 34 - - HYPH cord-276598-tm0yj2sn 1015 35 Sensitive Sensitive NNP cord-276598-tm0yj2sn 1015 36 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 1015 37 - - HYPH cord-276598-tm0yj2sn 1015 38 Based Based NNP cord-276598-tm0yj2sn 1015 39 Linkers Linkers NNP cord-276598-tm0yj2sn 1015 40 for for IN cord-276598-tm0yj2sn 1015 41 Controlled Controlled NNP cord-276598-tm0yj2sn 1015 42 Release Release NNP cord-276598-tm0yj2sn 1015 43 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 1015 44 derivates derivate NNS cord-276598-tm0yj2sn 1015 45 as as IN cord-276598-tm0yj2sn 1015 46 controlled control VBN cord-276598-tm0yj2sn 1015 47 - - HYPH cord-276598-tm0yj2sn 1015 48 release release NN cord-276598-tm0yj2sn 1015 49 prodrugs prodrug NNS cord-276598-tm0yj2sn 1015 50 of of IN cord-276598-tm0yj2sn 1015 51 l l NN cord-276598-tm0yj2sn 1015 52 - - HYPH cord-276598-tm0yj2sn 1015 53 Dopa Dopa NNP cord-276598-tm0yj2sn 1015 54 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 1015 55 derivatives derivative NNS cord-276598-tm0yj2sn 1015 56 of of IN cord-276598-tm0yj2sn 1015 57 acyclovir acyclovir NN cord-276598-tm0yj2sn 1015 58 : : : cord-276598-tm0yj2sn 1015 59 Synthesis synthesis NN cord-276598-tm0yj2sn 1015 60 and and CC cord-276598-tm0yj2sn 1015 61 antiviral antiviral JJ cord-276598-tm0yj2sn 1015 62 activity activity NN cord-276598-tm0yj2sn 1015 63 in in IN cord-276598-tm0yj2sn 1015 64 HIV-1 HIV-1 NNP cord-276598-tm0yj2sn 1015 65 and and CC cord-276598-tm0yj2sn 1015 66 HSV-1 HSV-1 NNP cord-276598-tm0yj2sn 1015 67 models model NNS cord-276598-tm0yj2sn 1015 68 in in IN cord-276598-tm0yj2sn 1015 69 vitro vitro FW cord-276598-tm0yj2sn 1015 70 The the DT cord-276598-tm0yj2sn 1015 71 nature nature NN cord-276598-tm0yj2sn 1015 72 of of IN cord-276598-tm0yj2sn 1015 73 the the DT cord-276598-tm0yj2sn 1015 74 " " `` cord-276598-tm0yj2sn 1015 75 inorganic inorganic JJ cord-276598-tm0yj2sn 1015 76 phosphate phosphate NN cord-276598-tm0yj2sn 1015 77 " " '' cord-276598-tm0yj2sn 1015 78 in in IN cord-276598-tm0yj2sn 1015 79 voluntary voluntary JJ cord-276598-tm0yj2sn 1015 80 muscle muscle NN cord-276598-tm0yj2sn 1015 81 Phosphorus phosphorus NN cord-276598-tm0yj2sn 1015 82 compounds compound NNS cord-276598-tm0yj2sn 1015 83 of of IN cord-276598-tm0yj2sn 1015 84 muscle muscle NN cord-276598-tm0yj2sn 1015 85 and and CC cord-276598-tm0yj2sn 1015 86 liver liver NN cord-276598-tm0yj2sn 1016 1 The the DT cord-276598-tm0yj2sn 1016 2 Aquo Aquo NNP cord-276598-tm0yj2sn 1016 3 Ammono Ammono NNP cord-276598-tm0yj2sn 1016 4 Phosphoric Phosphoric NNP cord-276598-tm0yj2sn 1016 5 Acids Acids NNPS cord-276598-tm0yj2sn 1016 6 . . . cord-276598-tm0yj2sn 1017 1 I. I. NNP cord-276598-tm0yj2sn 1017 2 Preparation preparation NN cord-276598-tm0yj2sn 1017 3 of of IN cord-276598-tm0yj2sn 1017 4 Phenyl Phenyl NNP cord-276598-tm0yj2sn 1017 5 Esters Esters NNPS cord-276598-tm0yj2sn 1017 6 of of IN cord-276598-tm0yj2sn 1017 7 Amidoand Amidoand NNP cord-276598-tm0yj2sn 1017 8 Diamidophosphoric Diamidophosphoric NNP cord-276598-tm0yj2sn 1017 9 Acids Acids NNPS cord-276598-tm0yj2sn 1018 1 The the DT cord-276598-tm0yj2sn 1018 2 Aquo Aquo NNP cord-276598-tm0yj2sn 1018 3 Ammono Ammono NNP cord-276598-tm0yj2sn 1018 4 Phosphoric Phosphoric NNP cord-276598-tm0yj2sn 1018 5 Acids Acids NNPS cord-276598-tm0yj2sn 1018 6 . . . cord-276598-tm0yj2sn 1019 1 II II NNP cord-276598-tm0yj2sn 1019 2 . . . cord-276598-tm0yj2sn 1020 1 Preparation preparation NN cord-276598-tm0yj2sn 1020 2 of of IN cord-276598-tm0yj2sn 1020 3 N N NNP cord-276598-tm0yj2sn 1020 4 - - HYPH cord-276598-tm0yj2sn 1020 5 Substituted Substituted NNP cord-276598-tm0yj2sn 1020 6 Derivatives Derivatives NNPS cord-276598-tm0yj2sn 1020 7 of of IN cord-276598-tm0yj2sn 1020 8 the the DT cord-276598-tm0yj2sn 1020 9 Phenyl Phenyl NNP cord-276598-tm0yj2sn 1020 10 Esters Esters NNPS cord-276598-tm0yj2sn 1020 11 of of IN cord-276598-tm0yj2sn 1020 12 Amido Amido NNP cord-276598-tm0yj2sn 1020 13 - - : cord-276598-tm0yj2sn 1020 14 and and CC cord-276598-tm0yj2sn 1020 15 Diamidophosphoric Diamidophosphoric NNP cord-276598-tm0yj2sn 1020 16 Acids Acids NNPS cord-276598-tm0yj2sn 1020 17 174 174 CD cord-276598-tm0yj2sn 1020 18 . . . cord-276598-tm0yj2sn 1021 1 Studies study NNS cord-276598-tm0yj2sn 1021 2 on on IN cord-276598-tm0yj2sn 1021 3 phosphorylation phosphorylation NN cord-276598-tm0yj2sn 1021 4 . . . cord-276598-tm0yj2sn 1022 1 Part Part NNP cord-276598-tm0yj2sn 1022 2 II II NNP cord-276598-tm0yj2sn 1022 3 . . . cord-276598-tm0yj2sn 1023 1 The the DT cord-276598-tm0yj2sn 1023 2 reaction reaction NN cord-276598-tm0yj2sn 1023 3 of of IN cord-276598-tm0yj2sn 1023 4 dialkyl dialkyl NNP cord-276598-tm0yj2sn 1023 5 phosphites phosphites NNP cord-276598-tm0yj2sn 1023 6 with with IN cord-276598-tm0yj2sn 1023 7 polyhalogen polyhalogen NNP cord-276598-tm0yj2sn 1023 8 compounds compound NNS cord-276598-tm0yj2sn 1023 9 in in IN cord-276598-tm0yj2sn 1023 10 presence presence NN cord-276598-tm0yj2sn 1023 11 of of IN cord-276598-tm0yj2sn 1023 12 bases basis NNS cord-276598-tm0yj2sn 1023 13 . . . cord-276598-tm0yj2sn 1024 1 A a DT cord-276598-tm0yj2sn 1024 2 new new JJ cord-276598-tm0yj2sn 1024 3 method method NN cord-276598-tm0yj2sn 1024 4 for for IN cord-276598-tm0yj2sn 1024 5 the the DT cord-276598-tm0yj2sn 1024 6 phosphorylation phosphorylation NN cord-276598-tm0yj2sn 1024 7 of of IN cord-276598-tm0yj2sn 1024 8 amines amine NNS cord-276598-tm0yj2sn 1024 9 129 129 CD cord-276598-tm0yj2sn 1024 10 . . . cord-276598-tm0yj2sn 1025 1 Studies study NNS cord-276598-tm0yj2sn 1025 2 on on IN cord-276598-tm0yj2sn 1025 3 phosphorylation phosphorylation NN cord-276598-tm0yj2sn 1025 4 . . . cord-276598-tm0yj2sn 1026 1 Part part NN cord-276598-tm0yj2sn 1026 2 III III NNP cord-276598-tm0yj2sn 1026 3 . . . cord-276598-tm0yj2sn 1027 1 Further further JJ cord-276598-tm0yj2sn 1027 2 observations observation NNS cord-276598-tm0yj2sn 1027 3 on on IN cord-276598-tm0yj2sn 1027 4 the the DT cord-276598-tm0yj2sn 1027 5 reaction reaction NN cord-276598-tm0yj2sn 1027 6 of of IN cord-276598-tm0yj2sn 1027 7 phosphites phosphites NNP cord-276598-tm0yj2sn 1027 8 with with IN cord-276598-tm0yj2sn 1027 9 polyhalogen polyhalogen NNP cord-276598-tm0yj2sn 1027 10 compounds compound NNS cord-276598-tm0yj2sn 1027 11 in in IN cord-276598-tm0yj2sn 1027 12 presence presence NN cord-276598-tm0yj2sn 1027 13 of of IN cord-276598-tm0yj2sn 1027 14 bases basis NNS cord-276598-tm0yj2sn 1027 15 and and CC cord-276598-tm0yj2sn 1027 16 its -PRON- PRP$ cord-276598-tm0yj2sn 1027 17 application application NN cord-276598-tm0yj2sn 1027 18 to to IN cord-276598-tm0yj2sn 1027 19 the the DT cord-276598-tm0yj2sn 1027 20 phosphorylation phosphorylation NN cord-276598-tm0yj2sn 1027 21 of of IN cord-276598-tm0yj2sn 1027 22 alcohols alcohol NNS cord-276598-tm0yj2sn 1027 23 220 220 CD cord-276598-tm0yj2sn 1027 24 . . . cord-276598-tm0yj2sn 1028 1 Studies study NNS cord-276598-tm0yj2sn 1028 2 on on IN cord-276598-tm0yj2sn 1028 3 phosphorylation phosphorylation NN cord-276598-tm0yj2sn 1028 4 . . . cord-276598-tm0yj2sn 1029 1 Part Part NNP cord-276598-tm0yj2sn 1029 2 IV IV NNP cord-276598-tm0yj2sn 1029 3 . . . cord-276598-tm0yj2sn 1030 1 Further further JJ cord-276598-tm0yj2sn 1030 2 studies study NNS cord-276598-tm0yj2sn 1030 3 on on IN cord-276598-tm0yj2sn 1030 4 the the DT cord-276598-tm0yj2sn 1030 5 use use NN cord-276598-tm0yj2sn 1030 6 of of IN cord-276598-tm0yj2sn 1030 7 dibenzyl dibenzyl NNP cord-276598-tm0yj2sn 1030 8 chlorophosphonate chlorophosphonate NNP cord-276598-tm0yj2sn 1030 9 and and CC cord-276598-tm0yj2sn 1030 10 the the DT cord-276598-tm0yj2sn 1030 11 examination examination NN cord-276598-tm0yj2sn 1030 12 of of IN cord-276598-tm0yj2sn 1030 13 certain certain JJ cord-276598-tm0yj2sn 1030 14 alternative alternative JJ cord-276598-tm0yj2sn 1030 15 phosphorylation phosphorylation NN cord-276598-tm0yj2sn 1030 16 methods method NNS cord-276598-tm0yj2sn 1031 1 The the DT cord-276598-tm0yj2sn 1031 2 Reaction reaction NN cord-276598-tm0yj2sn 1031 3 of of IN cord-276598-tm0yj2sn 1031 4 Phosphorus Phosphorus NNP cord-276598-tm0yj2sn 1031 5 - - HYPH cord-276598-tm0yj2sn 1031 6 containing contain VBG cord-276598-tm0yj2sn 1031 7 Enzyme Enzyme NNP cord-276598-tm0yj2sn 1031 8 Inhibitors Inhibitors NNP cord-276598-tm0yj2sn 1031 9 with with IN cord-276598-tm0yj2sn 1031 10 Amines Amines NNPS cord-276598-tm0yj2sn 1031 11 and and CC cord-276598-tm0yj2sn 1031 12 Amino amino NN cord-276598-tm0yj2sn 1031 13 Acid acid NN cord-276598-tm0yj2sn 1031 14 Derivatives1 Derivatives1 NNP cord-276598-tm0yj2sn 1032 1 The the DT cord-276598-tm0yj2sn 1032 2 Formation Formation NNP cord-276598-tm0yj2sn 1032 3 of of IN cord-276598-tm0yj2sn 1032 4 P P NNP cord-276598-tm0yj2sn 1032 5 - - HYPH cord-276598-tm0yj2sn 1032 6 N N NNP cord-276598-tm0yj2sn 1032 7 and and CC cord-276598-tm0yj2sn 1032 8 P P NNP cord-276598-tm0yj2sn 1032 9 - - HYPH cord-276598-tm0yj2sn 1032 10 N N NNP cord-276598-tm0yj2sn 1032 11 - - HYPH cord-276598-tm0yj2sn 1032 12 P P NNP cord-276598-tm0yj2sn 1032 13 Bonds Bonds NNPS cord-276598-tm0yj2sn 1032 14 by by IN cord-276598-tm0yj2sn 1032 15 Elimination Elimination NNP cord-276598-tm0yj2sn 1032 16 of of IN cord-276598-tm0yj2sn 1032 17 Phenol Phenol NNP cord-276598-tm0yj2sn 1032 18 in in IN cord-276598-tm0yj2sn 1032 19 a a DT cord-276598-tm0yj2sn 1032 20 Basic basic JJ cord-276598-tm0yj2sn 1032 21 Condensation Condensation NNP cord-276598-tm0yj2sn 1032 22 Deoxygenation Deoxygenation NNP cord-276598-tm0yj2sn 1032 23 of of IN cord-276598-tm0yj2sn 1032 24 Nitro Nitro NNP cord-276598-tm0yj2sn 1032 25 Groups Groups NNPS cord-276598-tm0yj2sn 1032 26 by by IN cord-276598-tm0yj2sn 1032 27 Trivalent Trivalent NNP cord-276598-tm0yj2sn 1032 28 Phosphorus Phosphorus NNP cord-276598-tm0yj2sn 1032 29 . . . cord-276598-tm0yj2sn 1033 1 Indoles Indoles NNP cord-276598-tm0yj2sn 1033 2 from from IN cord-276598-tm0yj2sn 1033 3 o o NN cord-276598-tm0yj2sn 1033 4 - - HYPH cord-276598-tm0yj2sn 1033 5 Nitrostyrenes Nitrostyrenes NNPS cord-276598-tm0yj2sn 1034 1 The the DT cord-276598-tm0yj2sn 1034 2 Reactivity Reactivity NNP cord-276598-tm0yj2sn 1034 3 of of IN cord-276598-tm0yj2sn 1034 4 Organophosphorus Organophosphorus NNP cord-276598-tm0yj2sn 1034 5 Compounds Compounds NNPS cord-276598-tm0yj2sn 1034 6 . . . cord-276598-tm0yj2sn 1035 1 Part part NN cord-276598-tm0yj2sn 1035 2 XX1 XX1 NNP cord-276598-tm0yj2sn 1035 3 . . . cord-276598-tm0yj2sn 1036 1 P= p= NN cord-276598-tm0yj2sn 1037 1 O o UH cord-276598-tm0yj2sn 1037 2 Nucleophilicity Nucleophilicity NNP cord-276598-tm0yj2sn 1037 3 in in IN cord-276598-tm0yj2sn 1037 4 Phosphonates Phosphonates NNP cord-276598-tm0yj2sn 1037 5 and and CC cord-276598-tm0yj2sn 1037 6 Phosphoramidates Phosphoramidates NNP cord-276598-tm0yj2sn 1037 7 Reduction Reduction NNP cord-276598-tm0yj2sn 1037 8 of of IN cord-276598-tm0yj2sn 1037 9 nitro nitro NN cord-276598-tm0yj2sn 1037 10 - - HYPH cord-276598-tm0yj2sn 1037 11 and and CC cord-276598-tm0yj2sn 1037 12 nitroso nitroso NNS cord-276598-tm0yj2sn 1037 13 - - HYPH cord-276598-tm0yj2sn 1037 14 compounds compound NNS cord-276598-tm0yj2sn 1037 15 by by IN cord-276598-tm0yj2sn 1037 16 tervalent tervalent NN cord-276598-tm0yj2sn 1037 17 phosphorus phosphorus NN cord-276598-tm0yj2sn 1037 18 reagents reagent NNS cord-276598-tm0yj2sn 1037 19 . . . cord-276598-tm0yj2sn 1038 1 Part part NN cord-276598-tm0yj2sn 1038 2 V. V. NNP cord-276598-tm0yj2sn 1038 3 Reduction Reduction NNP cord-276598-tm0yj2sn 1038 4 of of IN cord-276598-tm0yj2sn 1038 5 alkyl alkyl NN cord-276598-tm0yj2sn 1038 6 - - : cord-276598-tm0yj2sn 1038 7 and and CC cord-276598-tm0yj2sn 1038 8 methoxy methoxy NNS cord-276598-tm0yj2sn 1038 9 - - HYPH cord-276598-tm0yj2sn 1038 10 nitrobenzenes nitrobenzene NNS cord-276598-tm0yj2sn 1038 11 , , , cord-276598-tm0yj2sn 1038 12 and and CC cord-276598-tm0yj2sn 1038 13 nitrobenzene nitrobenzene NN cord-276598-tm0yj2sn 1038 14 by by IN cord-276598-tm0yj2sn 1038 15 trialkyl trialkyl NNP cord-276598-tm0yj2sn 1038 16 phosphites phosphites NNP cord-276598-tm0yj2sn 1038 17 Phase Phase NNP cord-276598-tm0yj2sn 1038 18 - - HYPH cord-276598-tm0yj2sn 1038 19 Transfer Transfer NNP cord-276598-tm0yj2sn 1038 20 - - HYPH cord-276598-tm0yj2sn 1038 21 Catalysed Catalysed NNP cord-276598-tm0yj2sn 1038 22 Phosphorylation Phosphorylation NNP cord-276598-tm0yj2sn 1038 23 of of IN cord-276598-tm0yj2sn 1038 24 Amines Amines NNPS cord-276598-tm0yj2sn 1038 25 in in IN cord-276598-tm0yj2sn 1038 26 an an DT cord-276598-tm0yj2sn 1038 27 Aqueous Aqueous NNP cord-276598-tm0yj2sn 1038 28 System System NNP cord-276598-tm0yj2sn 1038 29 Selective Selective NNP cord-276598-tm0yj2sn 1038 30 N n CD cord-276598-tm0yj2sn 1038 31 - - HYPH cord-276598-tm0yj2sn 1038 32 Alkylation alkylation NN cord-276598-tm0yj2sn 1038 33 of of IN cord-276598-tm0yj2sn 1038 34 Diethyl Diethyl NNP cord-276598-tm0yj2sn 1038 35 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 1038 36 : : : cord-276598-tm0yj2sn 1038 37 Tetrabutylaminium Tetrabutylaminium NNP cord-276598-tm0yj2sn 1038 38 Bromide Bromide NNP cord-276598-tm0yj2sn 1038 39 as as IN cord-276598-tm0yj2sn 1038 40 Catalyst Catalyst NNP cord-276598-tm0yj2sn 1038 41 for for IN cord-276598-tm0yj2sn 1038 42 Nucleophilic Nucleophilic NNP cord-276598-tm0yj2sn 1038 43 Substitution Substitution NNP cord-276598-tm0yj2sn 1038 44 in in IN cord-276598-tm0yj2sn 1038 45 a a DT cord-276598-tm0yj2sn 1038 46 Homogeneous Homogeneous NNP cord-276598-tm0yj2sn 1038 47 Medium Medium NNP cord-276598-tm0yj2sn 1038 48 A A NNP cord-276598-tm0yj2sn 1038 49 Convenient convenient JJ cord-276598-tm0yj2sn 1038 50 Method method NN cord-276598-tm0yj2sn 1038 51 for for IN cord-276598-tm0yj2sn 1038 52 the the DT cord-276598-tm0yj2sn 1038 53 Protection Protection NNP cord-276598-tm0yj2sn 1038 54 of of IN cord-276598-tm0yj2sn 1038 55 Amino Amino NNP cord-276598-tm0yj2sn 1038 56 Groups Groups NNPS cord-276598-tm0yj2sn 1038 57 as as IN cord-276598-tm0yj2sn 1038 58 Diethyl Diethyl NNP cord-276598-tm0yj2sn 1038 59 Phosphoramidates Phosphoramidates NNP cord-276598-tm0yj2sn 1038 60 Direct direct JJ cord-276598-tm0yj2sn 1038 61 conversion conversion NN cord-276598-tm0yj2sn 1038 62 of of IN cord-276598-tm0yj2sn 1038 63 diethyl diethyl JJ cord-276598-tm0yj2sn 1038 64 hydrogen hydrogen NN cord-276598-tm0yj2sn 1038 65 phosphate phosphate NN cord-276598-tm0yj2sn 1038 66 into into IN cord-276598-tm0yj2sn 1038 67 diethyl diethyl NN cord-276598-tm0yj2sn 1038 68 phosphoramides phosphoramides NNP cord-276598-tm0yj2sn 1038 69 Zur Zur NNP cord-276598-tm0yj2sn 1038 70 Umsetzung Umsetzung NNP cord-276598-tm0yj2sn 1038 71 des des NNP cord-276598-tm0yj2sn 1039 1 Zweikomponentensystems Zweikomponentensystems NNP cord-276598-tm0yj2sn 1039 2 Trialkylphosphit/ trialkylphosphit/ CD cord-276598-tm0yj2sn 1040 1 Tetrachlorkohlenstoff Tetrachlorkohlenstoff NNP cord-276598-tm0yj2sn 1040 2 mit mit VBP cord-276598-tm0yj2sn 1040 3 wasserstoffhaltigen wasserstoffhaltigen NNP cord-276598-tm0yj2sn 1040 4 Nucleophilen Nucleophilen NNP cord-276598-tm0yj2sn 1040 5 2 2 CD cord-276598-tm0yj2sn 1040 6 . . . cord-276598-tm0yj2sn 1041 1 Die die VB cord-276598-tm0yj2sn 1041 2 Reaktion Reaktion NNP cord-276598-tm0yj2sn 1041 3 mit mit NNP cord-276598-tm0yj2sn 1041 4 Ammoniak Ammoniak NNP cord-276598-tm0yj2sn 1041 5 und und IN cord-276598-tm0yj2sn 1042 1 Aminen Aminen NNP cord-276598-tm0yj2sn 1042 2 Directed Directed NNP cord-276598-tm0yj2sn 1042 3 Arbuzov Arbuzov NNP cord-276598-tm0yj2sn 1042 4 - - HYPH cord-276598-tm0yj2sn 1042 5 type type NN cord-276598-tm0yj2sn 1042 6 reactions reaction NNS cord-276598-tm0yj2sn 1042 7 of of IN cord-276598-tm0yj2sn 1042 8 2-cyano-1,1-dimethylethyl 2-cyano-1,1-dimethylethyl NNP cord-276598-tm0yj2sn 1042 9 deoxynucleoside deoxynucleoside NNP cord-276598-tm0yj2sn 1042 10 phosphites phosphites NNP cord-276598-tm0yj2sn 1042 11 A a DT cord-276598-tm0yj2sn 1042 12 facile facile JJ cord-276598-tm0yj2sn 1042 13 one one CD cord-276598-tm0yj2sn 1042 14 - - HYPH cord-276598-tm0yj2sn 1042 15 pot pot NN cord-276598-tm0yj2sn 1042 16 transformation transformation NN cord-276598-tm0yj2sn 1042 17 of of IN cord-276598-tm0yj2sn 1042 18 alkyl alkyl JJ cord-276598-tm0yj2sn 1042 19 bromides bromide NNS cord-276598-tm0yj2sn 1042 20 into into IN cord-276598-tm0yj2sn 1042 21 Diethyl Diethyl NNP cord-276598-tm0yj2sn 1042 22 N N NNP cord-276598-tm0yj2sn 1042 23 - - HYPH cord-276598-tm0yj2sn 1042 24 Alkylphosphoroamidates Alkylphosphoroamidates NNP cord-276598-tm0yj2sn 1042 25 Preparation Preparation NNP cord-276598-tm0yj2sn 1042 26 of of IN cord-276598-tm0yj2sn 1042 27 sterically sterically RB cord-276598-tm0yj2sn 1042 28 hindered hinder VBN cord-276598-tm0yj2sn 1042 29 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 1042 30 A a DT cord-276598-tm0yj2sn 1042 31 phosphoryl phosphoryl NN cord-276598-tm0yj2sn 1042 32 radical radical RB cord-276598-tm0yj2sn 1042 33 - - HYPH cord-276598-tm0yj2sn 1042 34 initiated initiate VBN cord-276598-tm0yj2sn 1042 35 Atherton Atherton NNP cord-276598-tm0yj2sn 1042 36 - - HYPH cord-276598-tm0yj2sn 1042 37 Todd Todd NNP cord-276598-tm0yj2sn 1042 38 - - HYPH cord-276598-tm0yj2sn 1042 39 type type NN cord-276598-tm0yj2sn 1042 40 reaction reaction NN cord-276598-tm0yj2sn 1042 41 under under IN cord-276598-tm0yj2sn 1042 42 open open JJ cord-276598-tm0yj2sn 1042 43 air air NN cord-276598-tm0yj2sn 1042 44 A a DT cord-276598-tm0yj2sn 1042 45 New New NNP cord-276598-tm0yj2sn 1042 46 Approach Approach NNP cord-276598-tm0yj2sn 1042 47 to to IN cord-276598-tm0yj2sn 1042 48 the the DT cord-276598-tm0yj2sn 1042 49 Atherton Atherton NNP cord-276598-tm0yj2sn 1042 50 - - HYPH cord-276598-tm0yj2sn 1042 51 Todd Todd NNP cord-276598-tm0yj2sn 1042 52 Reaction Reaction NNP cord-276598-tm0yj2sn 1042 53 Efficient Efficient NNP cord-276598-tm0yj2sn 1042 54 and and CC cord-276598-tm0yj2sn 1042 55 Convenient convenient JJ cord-276598-tm0yj2sn 1042 56 One one CD cord-276598-tm0yj2sn 1042 57 - - HYPH cord-276598-tm0yj2sn 1042 58 Pot Pot NNP cord-276598-tm0yj2sn 1042 59 Synthesis Synthesis NNP cord-276598-tm0yj2sn 1042 60 of of IN cord-276598-tm0yj2sn 1042 61 Phosphoramidates Phosphoramidates NNPS cord-276598-tm0yj2sn 1042 62 and and CC cord-276598-tm0yj2sn 1042 63 Phosphates Phosphates NNPS cord-276598-tm0yj2sn 1042 64 Trichloroisocyanuric Trichloroisocyanuric NNP cord-276598-tm0yj2sn 1042 65 Acid Acid NNP cord-276598-tm0yj2sn 1042 66 as as IN cord-276598-tm0yj2sn 1042 67 an an DT cord-276598-tm0yj2sn 1042 68 Efficient Efficient NNP cord-276598-tm0yj2sn 1042 69 Reagent reagent NN cord-276598-tm0yj2sn 1042 70 for for IN cord-276598-tm0yj2sn 1042 71 the the DT cord-276598-tm0yj2sn 1042 72 Synthesis Synthesis NNP cord-276598-tm0yj2sn 1042 73 of of IN cord-276598-tm0yj2sn 1042 74 Phosphoroamidates Phosphoroamidates NNP cord-276598-tm0yj2sn 1042 75 via via IN cord-276598-tm0yj2sn 1042 76 Atherton Atherton NNP cord-276598-tm0yj2sn 1042 77 - - HYPH cord-276598-tm0yj2sn 1042 78 Todd Todd NNP cord-276598-tm0yj2sn 1042 79 Reaction Reaction NNP cord-276598-tm0yj2sn 1042 80 under under IN cord-276598-tm0yj2sn 1042 81 Base Base NNP cord-276598-tm0yj2sn 1042 82 - - HYPH cord-276598-tm0yj2sn 1042 83 Free Free NNP cord-276598-tm0yj2sn 1042 84 Conditions condition NNS cord-276598-tm0yj2sn 1042 85 Efficient efficient JJ cord-276598-tm0yj2sn 1042 86 Amidation Amidation NNP cord-276598-tm0yj2sn 1042 87 and and CC cord-276598-tm0yj2sn 1042 88 Esterification Esterification NNP cord-276598-tm0yj2sn 1042 89 of of IN cord-276598-tm0yj2sn 1042 90 Phosphoric Phosphoric NNP cord-276598-tm0yj2sn 1042 91 Acid acid NN cord-276598-tm0yj2sn 1043 1 Using use VBG cord-276598-tm0yj2sn 1043 2 Cl3CCN/ cl3ccn/ PRP cord-276598-tm0yj2sn 1044 1 Ph3P Ph3P NNP cord-276598-tm0yj2sn 1045 1 Neues Neues NNP cord-276598-tm0yj2sn 1045 2 Verfahren Verfahren NNP cord-276598-tm0yj2sn 1045 3 zur zur NNP cord-276598-tm0yj2sn 1045 4 Darstellung Darstellung NNP cord-276598-tm0yj2sn 1045 5 von von NNP cord-276598-tm0yj2sn 1045 6 Phosphorsäureesteramiden Phosphorsäureesteramiden NNP cord-276598-tm0yj2sn 1045 7 , , , cord-276598-tm0yj2sn 1045 8 Phosphinsäureamiden Phosphinsäureamiden NNP cord-276598-tm0yj2sn 1045 9 , , , cord-276598-tm0yj2sn 1045 10 Phosphinsäureestern Phosphinsäureestern NNP cord-276598-tm0yj2sn 1045 11 und und IN cord-276598-tm0yj2sn 1045 12 gemischt gemischt NNP cord-276598-tm0yj2sn 1045 13 substituierten substituierten NNP cord-276598-tm0yj2sn 1046 1 Phosphorsäuretriestern Phosphorsäuretriestern NNP cord-276598-tm0yj2sn 1046 2 Reinvestigation Reinvestigation NNP cord-276598-tm0yj2sn 1046 3 of of IN cord-276598-tm0yj2sn 1046 4 the the DT cord-276598-tm0yj2sn 1046 5 iodine iodine NN cord-276598-tm0yj2sn 1046 6 - - HYPH cord-276598-tm0yj2sn 1046 7 mediated mediate VBN cord-276598-tm0yj2sn 1046 8 phosphoramidation phosphoramidation NN cord-276598-tm0yj2sn 1046 9 reaction reaction NN cord-276598-tm0yj2sn 1046 10 of of IN cord-276598-tm0yj2sn 1046 11 amines amine NNS cord-276598-tm0yj2sn 1046 12 and and CC cord-276598-tm0yj2sn 1046 13 P(OR)3 p(or)3 CD cord-276598-tm0yj2sn 1046 14 and and CC cord-276598-tm0yj2sn 1046 15 its -PRON- PRP$ cord-276598-tm0yj2sn 1046 16 synthetic synthetic JJ cord-276598-tm0yj2sn 1046 17 applications application NNS cord-276598-tm0yj2sn 1046 18 Iodine iodine NN cord-276598-tm0yj2sn 1046 19 catalyzed catalyze VBN cord-276598-tm0yj2sn 1046 20 solvent solvent NN cord-276598-tm0yj2sn 1046 21 - - HYPH cord-276598-tm0yj2sn 1046 22 free free JJ cord-276598-tm0yj2sn 1046 23 cross cross JJ cord-276598-tm0yj2sn 1046 24 - - JJ cord-276598-tm0yj2sn 1046 25 dehydrogenative dehydrogenative JJ cord-276598-tm0yj2sn 1046 26 coupling coupling NN cord-276598-tm0yj2sn 1046 27 of of IN cord-276598-tm0yj2sn 1046 28 arylamines arylamine NNS cord-276598-tm0yj2sn 1046 29 and and CC cord-276598-tm0yj2sn 1046 30 H H NNP cord-276598-tm0yj2sn 1046 31 - - HYPH cord-276598-tm0yj2sn 1046 32 phosphonates phosphonate NNS cord-276598-tm0yj2sn 1046 33 for for IN cord-276598-tm0yj2sn 1046 34 the the DT cord-276598-tm0yj2sn 1046 35 synthesis synthesis NN cord-276598-tm0yj2sn 1046 36 of of IN cord-276598-tm0yj2sn 1046 37 N n NN cord-276598-tm0yj2sn 1046 38 - - HYPH cord-276598-tm0yj2sn 1046 39 arylphosphoramidates arylphosphoramidate NNS cord-276598-tm0yj2sn 1046 40 under under IN cord-276598-tm0yj2sn 1046 41 atmospheric atmospheric JJ cord-276598-tm0yj2sn 1046 42 conditions condition NNS cord-276598-tm0yj2sn 1046 43 Cross Cross NNP cord-276598-tm0yj2sn 1046 44 - - HYPH cord-276598-tm0yj2sn 1046 45 Hetero Hetero NNP cord-276598-tm0yj2sn 1046 46 - - HYPH cord-276598-tm0yj2sn 1046 47 Dehydrogenative Dehydrogenative NNP cord-276598-tm0yj2sn 1046 48 Coupling Coupling NNP cord-276598-tm0yj2sn 1046 49 Reaction reaction NN cord-276598-tm0yj2sn 1046 50 of of IN cord-276598-tm0yj2sn 1046 51 Phosphites Phosphites NNP cord-276598-tm0yj2sn 1046 52 : : : cord-276598-tm0yj2sn 1046 53 A a DT cord-276598-tm0yj2sn 1046 54 Catalytic Catalytic NNP cord-276598-tm0yj2sn 1046 55 Metal metal NN cord-276598-tm0yj2sn 1046 56 - - HYPH cord-276598-tm0yj2sn 1046 57 Free Free NNP cord-276598-tm0yj2sn 1046 58 Phosphorylation Phosphorylation NNP cord-276598-tm0yj2sn 1046 59 of of IN cord-276598-tm0yj2sn 1046 60 Amines Amines NNPS cord-276598-tm0yj2sn 1046 61 and and CC cord-276598-tm0yj2sn 1046 62 Alcohols Alcohols NNP cord-276598-tm0yj2sn 1046 63 Phosphoramidate Phosphoramidate NNP cord-276598-tm0yj2sn 1046 64 synthesis synthesis NN cord-276598-tm0yj2sn 1046 65 via via IN cord-276598-tm0yj2sn 1046 66 copper copper NN cord-276598-tm0yj2sn 1046 67 - - HYPH cord-276598-tm0yj2sn 1046 68 catalysed catalyse VBN cord-276598-tm0yj2sn 1046 69 aerobic aerobic JJ cord-276598-tm0yj2sn 1046 70 oxidative oxidative JJ cord-276598-tm0yj2sn 1046 71 coupling coupling NN cord-276598-tm0yj2sn 1046 72 of of IN cord-276598-tm0yj2sn 1046 73 amines amine NNS cord-276598-tm0yj2sn 1046 74 and and CC cord-276598-tm0yj2sn 1046 75 H H NNP cord-276598-tm0yj2sn 1046 76 - - HYPH cord-276598-tm0yj2sn 1046 77 phosphonates phosphonates NNP cord-276598-tm0yj2sn 1046 78 Copper copper NN cord-276598-tm0yj2sn 1046 79 - - HYPH cord-276598-tm0yj2sn 1046 80 catalyzed catalyze VBN cord-276598-tm0yj2sn 1046 81 aerobic aerobic JJ cord-276598-tm0yj2sn 1046 82 oxidative oxidative JJ cord-276598-tm0yj2sn 1046 83 cross cross NN cord-276598-tm0yj2sn 1046 84 - - NN cord-276598-tm0yj2sn 1046 85 coupling coupling NN cord-276598-tm0yj2sn 1046 86 of of IN cord-276598-tm0yj2sn 1046 87 arylamines arylamine NNS cord-276598-tm0yj2sn 1046 88 and and CC cord-276598-tm0yj2sn 1046 89 dialkylphosphites dialkylphosphite NNS cord-276598-tm0yj2sn 1046 90 leading lead VBG cord-276598-tm0yj2sn 1046 91 to to IN cord-276598-tm0yj2sn 1046 92 N N NNP cord-276598-tm0yj2sn 1046 93 - - HYPH cord-276598-tm0yj2sn 1046 94 arylphosphoramidates arylphosphoramidate NNS cord-276598-tm0yj2sn 1046 95 Fe Fe NNP cord-276598-tm0yj2sn 1046 96 3 3 CD cord-276598-tm0yj2sn 1046 97 O o NN cord-276598-tm0yj2sn 1046 98 4 4 CD cord-276598-tm0yj2sn 1046 99 @MgO @MgO NNS cord-276598-tm0yj2sn 1046 100 nanoparticles nanoparticle NNS cord-276598-tm0yj2sn 1046 101 as as IN cord-276598-tm0yj2sn 1046 102 an an DT cord-276598-tm0yj2sn 1046 103 efficient efficient JJ cord-276598-tm0yj2sn 1046 104 recyclable recyclable JJ cord-276598-tm0yj2sn 1046 105 catalyst catalyst NN cord-276598-tm0yj2sn 1046 106 for for IN cord-276598-tm0yj2sn 1046 107 the the DT cord-276598-tm0yj2sn 1046 108 synthesis synthesis NN cord-276598-tm0yj2sn 1046 109 of of IN cord-276598-tm0yj2sn 1046 110 phosphoroamidates phosphoroamidate NNS cord-276598-tm0yj2sn 1046 111 via via IN cord-276598-tm0yj2sn 1046 112 the the DT cord-276598-tm0yj2sn 1046 113 Atherton Atherton NNP cord-276598-tm0yj2sn 1046 114 - - HYPH cord-276598-tm0yj2sn 1046 115 Todd Todd NNP cord-276598-tm0yj2sn 1046 116 reaction reaction NN cord-276598-tm0yj2sn 1047 1 A a DT cord-276598-tm0yj2sn 1047 2 single single JJ cord-276598-tm0yj2sn 1047 3 - - HYPH cord-276598-tm0yj2sn 1047 4 step step NN cord-276598-tm0yj2sn 1047 5 one one CD cord-276598-tm0yj2sn 1047 6 pot pot NN cord-276598-tm0yj2sn 1047 7 synthesis synthesis NN cord-276598-tm0yj2sn 1047 8 of of IN cord-276598-tm0yj2sn 1047 9 O o NN cord-276598-tm0yj2sn 1047 10 , , , cord-276598-tm0yj2sn 1047 11 O o UH cord-276598-tm0yj2sn 1047 12 -dialkyl -dialkyl NNP cord-276598-tm0yj2sn 1047 13 N N NNP cord-276598-tm0yj2sn 1047 14 , , , cord-276598-tm0yj2sn 1047 15 N N NNP cord-276598-tm0yj2sn 1047 16 - - HYPH cord-276598-tm0yj2sn 1047 17 dialkylphosphoramidates dialkylphosphoramidate NNS cord-276598-tm0yj2sn 1047 18 from from IN cord-276598-tm0yj2sn 1047 19 dialkylphosphites dialkylphosphites NNP cord-276598-tm0yj2sn 1047 20 Copper Copper NNP cord-276598-tm0yj2sn 1047 21 - - HYPH cord-276598-tm0yj2sn 1047 22 Catalyzed Catalyzed NNP cord-276598-tm0yj2sn 1047 23 Oxidative Oxidative NNP cord-276598-tm0yj2sn 1047 24 Cross Cross NNP cord-276598-tm0yj2sn 1047 25 - - HYPH cord-276598-tm0yj2sn 1047 26 Coupling Coupling NNP cord-276598-tm0yj2sn 1047 27 of of IN cord-276598-tm0yj2sn 1047 28 H H NNP cord-276598-tm0yj2sn 1047 29 - - HYPH cord-276598-tm0yj2sn 1047 30 Phosphonates Phosphonates NNPS cord-276598-tm0yj2sn 1047 31 and and CC cord-276598-tm0yj2sn 1047 32 Amides Amides NNPS cord-276598-tm0yj2sn 1047 33 to to IN cord-276598-tm0yj2sn 1047 34 N N NNP cord-276598-tm0yj2sn 1047 35 - - HYPH cord-276598-tm0yj2sn 1047 36 Acylphosphoramidates Acylphosphoramidates NNP cord-276598-tm0yj2sn 1047 37 Stereospecific Stereospecific NNP cord-276598-tm0yj2sn 1047 38 Aerobic Aerobic NNP cord-276598-tm0yj2sn 1047 39 Oxidative Oxidative NNP cord-276598-tm0yj2sn 1047 40 Dehydrocoupling Dehydrocoupling NNP cord-276598-tm0yj2sn 1047 41 of of IN cord-276598-tm0yj2sn 1047 42 P(O)-H P(O)-H NNP cord-276598-tm0yj2sn 1047 43 Bonds Bonds NNP cord-276598-tm0yj2sn 1047 44 with with IN cord-276598-tm0yj2sn 1047 45 Amines amine NNS cord-276598-tm0yj2sn 1047 46 Catalyzed catalyze VBN cord-276598-tm0yj2sn 1047 47 by by IN cord-276598-tm0yj2sn 1047 48 Copper Copper NNP cord-276598-tm0yj2sn 1047 49 Copper Copper NNP cord-276598-tm0yj2sn 1047 50 catalyzed catalyze VBN cord-276598-tm0yj2sn 1047 51 tandem tandem NN cord-276598-tm0yj2sn 1047 52 Chan Chan NNP cord-276598-tm0yj2sn 1047 53 - - HYPH cord-276598-tm0yj2sn 1047 54 Lam Lam NNP cord-276598-tm0yj2sn 1047 55 type type NN cord-276598-tm0yj2sn 1047 56 C C NNP cord-276598-tm0yj2sn 1047 57 - - HYPH cord-276598-tm0yj2sn 1047 58 N N NNP cord-276598-tm0yj2sn 1047 59 and and CC cord-276598-tm0yj2sn 1047 60 Staudinger Staudinger NNP cord-276598-tm0yj2sn 1047 61 - - HYPH cord-276598-tm0yj2sn 1047 62 phosphite phosphite NNP cord-276598-tm0yj2sn 1047 63 N N NNP cord-276598-tm0yj2sn 1047 64 - - HYPH cord-276598-tm0yj2sn 1047 65 P p NN cord-276598-tm0yj2sn 1047 66 coupling coupling NN cord-276598-tm0yj2sn 1047 67 for for IN cord-276598-tm0yj2sn 1047 68 the the DT cord-276598-tm0yj2sn 1047 69 synthesis synthesis NN cord-276598-tm0yj2sn 1047 70 of of IN cord-276598-tm0yj2sn 1047 71 N N NNP cord-276598-tm0yj2sn 1047 72 - - HYPH cord-276598-tm0yj2sn 1047 73 arylphosphoramidates arylphosphoramidate NNS cord-276598-tm0yj2sn 1047 74 Organophotocatalytic Organophotocatalytic NNP cord-276598-tm0yj2sn 1047 75 Synthesis Synthesis NNP cord-276598-tm0yj2sn 1047 76 of of IN cord-276598-tm0yj2sn 1047 77 Phosphoramidates Phosphoramidates NNP cord-276598-tm0yj2sn 1047 78 LiI lii NN cord-276598-tm0yj2sn 1047 79 / / SYM cord-276598-tm0yj2sn 1047 80 TBHP tbhp RB cord-276598-tm0yj2sn 1048 1 Mediated Mediated NNP cord-276598-tm0yj2sn 1048 2 Oxidative Oxidative NNP cord-276598-tm0yj2sn 1048 3 Cross Cross NNP cord-276598-tm0yj2sn 1048 4 - - HYPH cord-276598-tm0yj2sn 1048 5 Coupling Coupling NNP cord-276598-tm0yj2sn 1048 6 of of IN cord-276598-tm0yj2sn 1048 7 P(O)-H P(O)-H NNP cord-276598-tm0yj2sn 1048 8 Compounds compound NNS cord-276598-tm0yj2sn 1048 9 with with IN cord-276598-tm0yj2sn 1048 10 Phenols Phenols NNPS cord-276598-tm0yj2sn 1048 11 and and CC cord-276598-tm0yj2sn 1048 12 Various various JJ cord-276598-tm0yj2sn 1048 13 Nucleophiles Nucleophiles NNPS cord-276598-tm0yj2sn 1048 14 : : : cord-276598-tm0yj2sn 1049 1 Direct Direct NNP cord-276598-tm0yj2sn 1049 2 Access Access NNP cord-276598-tm0yj2sn 1049 3 to to IN cord-276598-tm0yj2sn 1049 4 the the DT cord-276598-tm0yj2sn 1049 5 Synthesis Synthesis NNP cord-276598-tm0yj2sn 1049 6 of of IN cord-276598-tm0yj2sn 1049 7 Organophosphates Organophosphates NNP cord-276598-tm0yj2sn 1049 8 Synthesis Synthesis NNP cord-276598-tm0yj2sn 1049 9 of of IN cord-276598-tm0yj2sn 1049 10 Phosphoramidates Phosphoramidates NNPS cord-276598-tm0yj2sn 1049 11 : : : cord-276598-tm0yj2sn 1050 1 A a DT cord-276598-tm0yj2sn 1050 2 Facile facile JJ cord-276598-tm0yj2sn 1050 3 Approach approach NN cord-276598-tm0yj2sn 1051 1 Based base VBN cord-276598-tm0yj2sn 1051 2 on on IN cord-276598-tm0yj2sn 1051 3 the the DT cord-276598-tm0yj2sn 1051 4 C C NNP cord-276598-tm0yj2sn 1051 5 - - HYPH cord-276598-tm0yj2sn 1051 6 N N NNP cord-276598-tm0yj2sn 1051 7 Bond Bond NNP cord-276598-tm0yj2sn 1051 8 Formation Formation NNP cord-276598-tm0yj2sn 1051 9 via via IN cord-276598-tm0yj2sn 1051 10 Ir Ir NNP cord-276598-tm0yj2sn 1051 11 - - HYPH cord-276598-tm0yj2sn 1051 12 Catalyzed Catalyzed NNP cord-276598-tm0yj2sn 1051 13 Direct Direct NNP cord-276598-tm0yj2sn 1051 14 C c NN cord-276598-tm0yj2sn 1051 15 - - HYPH cord-276598-tm0yj2sn 1051 16 H h NN cord-276598-tm0yj2sn 1051 17 Amidation Amidation NNP cord-276598-tm0yj2sn 1051 18 Ruthenium(iv Ruthenium(iv NNP cord-276598-tm0yj2sn 1051 19 ) ) -RRB- cord-276598-tm0yj2sn 1051 20 porphyrin porphyrin NN cord-276598-tm0yj2sn 1051 21 catalyzed catalyze VBD cord-276598-tm0yj2sn 1051 22 phosphoramidation phosphoramidation NN cord-276598-tm0yj2sn 1051 23 of of IN cord-276598-tm0yj2sn 1051 24 aldehydes aldehyde NNS cord-276598-tm0yj2sn 1051 25 with with IN cord-276598-tm0yj2sn 1051 26 phosphoryl phosphoryl NNP cord-276598-tm0yj2sn 1051 27 azides azides NNP cord-276598-tm0yj2sn 1051 28 as as IN cord-276598-tm0yj2sn 1051 29 a a DT cord-276598-tm0yj2sn 1051 30 nitrene nitrene JJ cord-276598-tm0yj2sn 1051 31 source source NN cord-276598-tm0yj2sn 1051 32 Iridium Iridium NNP cord-276598-tm0yj2sn 1051 33 - - HYPH cord-276598-tm0yj2sn 1051 34 Catalyzed Catalyzed NNP cord-276598-tm0yj2sn 1051 35 Phosphoramidation Phosphoramidation NNP cord-276598-tm0yj2sn 1051 36 of of IN cord-276598-tm0yj2sn 1051 37 Arene Arene NNP cord-276598-tm0yj2sn 1051 38 C C NNP cord-276598-tm0yj2sn 1051 39 - - HYPH cord-276598-tm0yj2sn 1051 40 H H NNP cord-276598-tm0yj2sn 1051 41 Bonds Bonds NNP cord-276598-tm0yj2sn 1051 42 with with IN cord-276598-tm0yj2sn 1051 43 Phosphoryl Phosphoryl NNP cord-276598-tm0yj2sn 1051 44 Azide Azide NNP cord-276598-tm0yj2sn 1051 45 Catalyst Catalyst NNP cord-276598-tm0yj2sn 1052 1 free free JJ cord-276598-tm0yj2sn 1052 2 , , , cord-276598-tm0yj2sn 1052 3 one one CD cord-276598-tm0yj2sn 1052 4 pot pot NN cord-276598-tm0yj2sn 1052 5 synthesis synthesis NN cord-276598-tm0yj2sn 1052 6 of of IN cord-276598-tm0yj2sn 1052 7 phosphoramidates phosphoramidate NNS cord-276598-tm0yj2sn 1052 8 under under IN cord-276598-tm0yj2sn 1052 9 environment environment NN cord-276598-tm0yj2sn 1052 10 friendly friendly JJ cord-276598-tm0yj2sn 1052 11 conditions condition NNS cord-276598-tm0yj2sn 1053 1 An an DT cord-276598-tm0yj2sn 1053 2 efficient efficient JJ cord-276598-tm0yj2sn 1053 3 synthesis synthesis NN cord-276598-tm0yj2sn 1053 4 of of IN cord-276598-tm0yj2sn 1053 5 phosphoramidates phosphoramidate NNS cord-276598-tm0yj2sn 1053 6 from from IN cord-276598-tm0yj2sn 1053 7 halides halide NNS cord-276598-tm0yj2sn 1053 8 in in IN cord-276598-tm0yj2sn 1053 9 aqueous aqueous JJ cord-276598-tm0yj2sn 1053 10 ethanol ethanol NN cord-276598-tm0yj2sn 1053 11 Transition transition NN cord-276598-tm0yj2sn 1053 12 - - HYPH cord-276598-tm0yj2sn 1053 13 metal metal NN cord-276598-tm0yj2sn 1053 14 - - HYPH cord-276598-tm0yj2sn 1053 15 free free JJ cord-276598-tm0yj2sn 1053 16 amination amination NN cord-276598-tm0yj2sn 1053 17 phosphoryl phosphoryl NNS cord-276598-tm0yj2sn 1053 18 azide azide NN cord-276598-tm0yj2sn 1053 19 for for IN cord-276598-tm0yj2sn 1053 20 the the DT cord-276598-tm0yj2sn 1053 21 synthesis synthesis NN cord-276598-tm0yj2sn 1053 22 of of IN cord-276598-tm0yj2sn 1053 23 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 1053 24 Practical Practical NNP cord-276598-tm0yj2sn 1053 25 and and CC cord-276598-tm0yj2sn 1053 26 reliable reliable JJ cord-276598-tm0yj2sn 1053 27 synthesis synthesis NN cord-276598-tm0yj2sn 1053 28 of of IN cord-276598-tm0yj2sn 1053 29 dialkyl dialkyl NNP cord-276598-tm0yj2sn 1053 30 N N NNP cord-276598-tm0yj2sn 1053 31 - - HYPH cord-276598-tm0yj2sn 1053 32 arylphosphoramidates arylphosphoramidate NNS cord-276598-tm0yj2sn 1053 33 with with IN cord-276598-tm0yj2sn 1053 34 nitroarenes nitroarene NNS cord-276598-tm0yj2sn 1053 35 as as IN cord-276598-tm0yj2sn 1053 36 substrates substrate NNS cord-276598-tm0yj2sn 1053 37 Synthesis Synthesis NNP cord-276598-tm0yj2sn 1053 38 of of IN cord-276598-tm0yj2sn 1053 39 N N NNP cord-276598-tm0yj2sn 1053 40 , , , cord-276598-tm0yj2sn 1053 41 N N NNP cord-276598-tm0yj2sn 1053 42 - - HYPH cord-276598-tm0yj2sn 1053 43 disubstituted disubstitute VBN cord-276598-tm0yj2sn 1053 44 phosphoramidatesvia phosphoramidatesvia NNP cord-276598-tm0yj2sn 1053 45 a a DT cord-276598-tm0yj2sn 1053 46 Lewis Lewis NNP cord-276598-tm0yj2sn 1053 47 acid acid NN cord-276598-tm0yj2sn 1053 48 - - HYPH cord-276598-tm0yj2sn 1053 49 catalyzed catalyze VBN cord-276598-tm0yj2sn 1053 50 phosphorimidate phosphorimidate NN cord-276598-tm0yj2sn 1053 51 rearrangement rearrangement NN cord-276598-tm0yj2sn 1053 52 Reaction reaction NN cord-276598-tm0yj2sn 1053 53 of of IN cord-276598-tm0yj2sn 1053 54 sodium sodium NN cord-276598-tm0yj2sn 1053 55 salts salt NNS cord-276598-tm0yj2sn 1053 56 of of IN cord-276598-tm0yj2sn 1053 57 dialkylphosphorous dialkylphosphorous JJ cord-276598-tm0yj2sn 1053 58 acids acid NNS cord-276598-tm0yj2sn 1053 59 with with IN cord-276598-tm0yj2sn 1053 60 carboxylic carboxylic JJ cord-276598-tm0yj2sn 1053 61 acid acid NN cord-276598-tm0yj2sn 1053 62 nitriles nitrile NNS cord-276598-tm0yj2sn 1053 63 Study Study NNP cord-276598-tm0yj2sn 1053 64 on on IN cord-276598-tm0yj2sn 1053 65 the the DT cord-276598-tm0yj2sn 1053 66 Atherton Atherton NNP cord-276598-tm0yj2sn 1053 67 - - HYPH cord-276598-tm0yj2sn 1053 68 Todd Todd NNP cord-276598-tm0yj2sn 1053 69 reaction reaction NN cord-276598-tm0yj2sn 1053 70 mechanism mechanism NN cord-276598-tm0yj2sn 1053 71 Cesium cesium NN cord-276598-tm0yj2sn 1053 72 Effect effect NN cord-276598-tm0yj2sn 1053 73 : : : cord-276598-tm0yj2sn 1053 74 High high JJ cord-276598-tm0yj2sn 1053 75 Chemoselectivity Chemoselectivity NNP cord-276598-tm0yj2sn 1053 76 in in IN cord-276598-tm0yj2sn 1053 77 Direct Direct NNP cord-276598-tm0yj2sn 1053 78 N N NNP cord-276598-tm0yj2sn 1053 79 - - HYPH cord-276598-tm0yj2sn 1053 80 Alkylation alkylation NN cord-276598-tm0yj2sn 1053 81 of of IN cord-276598-tm0yj2sn 1053 82 Amines Amines NNPS cord-276598-tm0yj2sn 1053 83 Improved Improved NNP cord-276598-tm0yj2sn 1053 84 Cs Cs NNP cord-276598-tm0yj2sn 1053 85 2 2 CD cord-276598-tm0yj2sn 1053 86 CO CO NNP cord-276598-tm0yj2sn 1053 87 3 3 CD cord-276598-tm0yj2sn 1053 88 Promoted promote VBN cord-276598-tm0yj2sn 1053 89 O o NN cord-276598-tm0yj2sn 1053 90 - - HYPH cord-276598-tm0yj2sn 1053 91 Alkylation alkylation NN cord-276598-tm0yj2sn 1053 92 of of IN cord-276598-tm0yj2sn 1053 93 Acids acid NNS cord-276598-tm0yj2sn 1053 94 Abnormally abnormally RB cord-276598-tm0yj2sn 1053 95 high high JJ cord-276598-tm0yj2sn 1053 96 nucleophilicity nucleophilicity NN cord-276598-tm0yj2sn 1053 97 of of IN cord-276598-tm0yj2sn 1053 98 micellar micellar NN cord-276598-tm0yj2sn 1053 99 - - HYPH cord-276598-tm0yj2sn 1053 100 bound bind VBN cord-276598-tm0yj2sn 1053 101 azide azide NN cord-276598-tm0yj2sn 1053 102 ion ion NN cord-276598-tm0yj2sn 1053 103 One one CD cord-276598-tm0yj2sn 1053 104 - - HYPH cord-276598-tm0yj2sn 1053 105 Pot pot NN cord-276598-tm0yj2sn 1053 106 Procedure Procedure NNP cord-276598-tm0yj2sn 1053 107 for for IN cord-276598-tm0yj2sn 1053 108 Diazo Diazo NNP cord-276598-tm0yj2sn 1053 109 Transfer Transfer NNP cord-276598-tm0yj2sn 1053 110 and and CC cord-276598-tm0yj2sn 1053 111 Azide−Alkyne Azide−Alkyne NNP cord-276598-tm0yj2sn 1053 112 Cycloaddition Cycloaddition NNP cord-276598-tm0yj2sn 1053 113 : : : cord-276598-tm0yj2sn 1053 114 Triazole Triazole NNP cord-276598-tm0yj2sn 1053 115 Linkages Linkages NNP cord-276598-tm0yj2sn 1053 116 from from IN cord-276598-tm0yj2sn 1053 117 Amines amine NNS cord-276598-tm0yj2sn 1053 118 We -PRON- PRP cord-276598-tm0yj2sn 1054 1 gratefully gratefully RB cord-276598-tm0yj2sn 1054 2 acknowledge acknowledge VB cord-276598-tm0yj2sn 1054 3 Ebonyi Ebonyi NNP cord-276598-tm0yj2sn 1054 4 State State NNP cord-276598-tm0yj2sn 1054 5 University University NNP cord-276598-tm0yj2sn 1054 6 Abakaliki Abakaliki NNP cord-276598-tm0yj2sn 1054 7 and and CC cord-276598-tm0yj2sn 1054 8 Tertiary Tertiary NNP cord-276598-tm0yj2sn 1054 9 Education Education NNP cord-276598-tm0yj2sn 1054 10 Trust Trust NNP cord-276598-tm0yj2sn 1054 11 Fund Fund NNP cord-276598-tm0yj2sn 1054 12 ( ( -LRB- cord-276598-tm0yj2sn 1054 13 TETFund TETFund NNP cord-276598-tm0yj2sn 1054 14 ) ) -RRB- cord-276598-tm0yj2sn 1054 15 Nigeria Nigeria NNP cord-276598-tm0yj2sn 1054 16 for for IN cord-276598-tm0yj2sn 1054 17 E.J.I E.J.I NNP cord-276598-tm0yj2sn 1054 18 's 's POS cord-276598-tm0yj2sn 1054 19 PhD phd NN cord-276598-tm0yj2sn 1054 20 Scholarship Scholarship NNP cord-276598-tm0yj2sn 1054 21 and and CC cord-276598-tm0yj2sn 1054 22 The the DT cord-276598-tm0yj2sn 1054 23 MacDiarmid MacDiarmid NNP cord-276598-tm0yj2sn 1054 24 Institute Institute NNP cord-276598-tm0yj2sn 1054 25 for for IN cord-276598-tm0yj2sn 1054 26 Advanced Advanced NNP cord-276598-tm0yj2sn 1054 27 Materials Materials NNPS cord-276598-tm0yj2sn 1054 28 and and CC cord-276598-tm0yj2sn 1054 29 Nanotechnology Nanotechnology NNP cord-276598-tm0yj2sn 1054 30 , , , cord-276598-tm0yj2sn 1054 31 Wellington Wellington NNP cord-276598-tm0yj2sn 1054 32 , , , cord-276598-tm0yj2sn 1054 33 New New NNP cord-276598-tm0yj2sn 1054 34 Zealand Zealand NNP cord-276598-tm0yj2sn 1054 35 for for IN cord-276598-tm0yj2sn 1054 36 financial financial JJ cord-276598-tm0yj2sn 1054 37 support support NN cord-276598-tm0yj2sn 1054 38 . . . cord-276598-tm0yj2sn 1055 1 The the DT cord-276598-tm0yj2sn 1055 2 authors author NNS cord-276598-tm0yj2sn 1055 3 declare declare VBP cord-276598-tm0yj2sn 1055 4 no no DT cord-276598-tm0yj2sn 1055 5 conflict conflict NN cord-276598-tm0yj2sn 1055 6 of of IN cord-276598-tm0yj2sn 1055 7 interest interest NN cord-276598-tm0yj2sn 1055 8 . . . cord-276598-tm0yj2sn 1056 1 Dialkyl Dialkyl NNP cord-276598-tm0yj2sn 1056 2 chlorophosphate chlorophosphate NNP cord-276598-tm0yj2sn 1056 3 ( ( -LRB- cord-276598-tm0yj2sn 1056 4 dACP dACP NNP cord-276598-tm0yj2sn 1056 5 ) ) -RRB- cord-276598-tm0yj2sn 1056 6 , , , cord-276598-tm0yj2sn 1056 7 dialkyl dialkyl NNP cord-276598-tm0yj2sn 1056 8 phosphoriodidate phosphoriodidate NNP cord-276598-tm0yj2sn 1056 9 ( ( -LRB- cord-276598-tm0yj2sn 1056 10 dAPPI dappi NN cord-276598-tm0yj2sn 1056 11 ) ) -RRB- cord-276598-tm0yj2sn 1056 12 , , , cord-276598-tm0yj2sn 1056 13 H h NN cord-276598-tm0yj2sn 1056 14 - - HYPH cord-276598-tm0yj2sn 1056 15 phosphonate phosphonate NNP cord-276598-tm0yj2sn 1056 16 ( ( -LRB- cord-276598-tm0yj2sn 1056 17 H h NN cord-276598-tm0yj2sn 1056 18 - - HYPH cord-276598-tm0yj2sn 1056 19 P P NNP cord-276598-tm0yj2sn 1056 20 ) ) -RRB- cord-276598-tm0yj2sn 1056 21 , , , cord-276598-tm0yj2sn 1056 22 phosphoramidate phosphoramidate NNP cord-276598-tm0yj2sn 1056 23 ( ( -LRB- cord-276598-tm0yj2sn 1056 24 P P NNP cord-276598-tm0yj2sn 1056 25 - - HYPH cord-276598-tm0yj2sn 1056 26 N N NNP cord-276598-tm0yj2sn 1056 27 ) ) -RRB- cord-276598-tm0yj2sn 1056 28 , , , cord-276598-tm0yj2sn 1056 29 trichloroisocyanuric trichloroisocyanuric NN cord-276598-tm0yj2sn 1056 30 acid acid NN cord-276598-tm0yj2sn 1056 31 ( ( -LRB- cord-276598-tm0yj2sn 1056 32 tCiC tCiC NNP cord-276598-tm0yj2sn 1056 33 - - HYPH cord-276598-tm0yj2sn 1056 34 A a NN cord-276598-tm0yj2sn 1056 35 ) ) -RRB- cord-276598-tm0yj2sn 1056 36 , , , cord-276598-tm0yj2sn 1056 37 1,3,5-triazinane-2,4,6-trione 1,3,5-triazinane-2,4,6-trione CD cord-276598-tm0yj2sn 1056 38 ( ( -LRB- cord-276598-tm0yj2sn 1056 39 tAtO tAtO NNP cord-276598-tm0yj2sn 1056 40 ) ) -RRB- cord-276598-tm0yj2sn 1056 41 , , , cord-276598-tm0yj2sn 1056 42 N N NNP cord-276598-tm0yj2sn 1056 43 - - HYPH cord-276598-tm0yj2sn 1056 44 acylphosphoramidates acylphosphoramidates NNP cord-276598-tm0yj2sn 1057 1 ( ( -LRB- cord-276598-tm0yj2sn 1057 2 AcP AcP NNP cord-276598-tm0yj2sn 1057 3 - - HYPH cord-276598-tm0yj2sn 1057 4 N N NNP cord-276598-tm0yj2sn 1057 5 ) ) -RRB- cord-276598-tm0yj2sn 1057 6 , , , cord-276598-tm0yj2sn 1057 7 diphenylphosphine diphenylphosphine JJ cord-276598-tm0yj2sn 1057 8 oxide oxide NN cord-276598-tm0yj2sn 1057 9 ( ( -LRB- cord-276598-tm0yj2sn 1057 10 dPPO dPPO NNP cord-276598-tm0yj2sn 1057 11 ) ) -RRB- cord-276598-tm0yj2sn 1057 12 , , , cord-276598-tm0yj2sn 1057 13 phosphonic phosphonic NNP cord-276598-tm0yj2sn 1057 14 acid acid NN cord-276598-tm0yj2sn 1057 15 ( ( -LRB- cord-276598-tm0yj2sn 1057 16 PP PP NNP cord-276598-tm0yj2sn 1057 17 - - HYPH cord-276598-tm0yj2sn 1057 18 A A NNP cord-276598-tm0yj2sn 1057 19 ) ) -RRB- cord-276598-tm0yj2sn 1057 20 , , . cord-276598-tm0yj2sn 1058 1 N n NN cord-276598-tm0yj2sn 1058 2 - - HYPH cord-276598-tm0yj2sn 1058 3 bromosuccinimide bromosuccinimide NNP cord-276598-tm0yj2sn 1058 4 ( ( -LRB- cord-276598-tm0yj2sn 1058 5 NBS NBS NNP cord-276598-tm0yj2sn 1058 6 ) ) -RRB- cord-276598-tm0yj2sn 1058 7 , , , cord-276598-tm0yj2sn 1058 8 diphenyl diphenyl NNP cord-276598-tm0yj2sn 1058 9 phosphoric phosphoric JJ cord-276598-tm0yj2sn 1058 10 acid acid NN cord-276598-tm0yj2sn 1058 11 ( ( -LRB- cord-276598-tm0yj2sn 1058 12 dPPA dPPA NNP cord-276598-tm0yj2sn 1058 13 ) ) -RRB- cord-276598-tm0yj2sn 1058 14 , , , cord-276598-tm0yj2sn 1058 15 triphenylphosphine triphenylphosphine NNP cord-276598-tm0yj2sn 1058 16 ( ( -LRB- cord-276598-tm0yj2sn 1058 17 tPP tPP NNP cord-276598-tm0yj2sn 1058 18 ) ) -RRB- cord-276598-tm0yj2sn 1058 19 , , , cord-276598-tm0yj2sn 1058 20 diisopropylchlorophosphate diisopropylchlorophosphate NNP cord-276598-tm0yj2sn 1058 21 ( ( -LRB- cord-276598-tm0yj2sn 1058 22 dPrCP dPrCP NNP cord-276598-tm0yj2sn 1058 23 ) ) -RRB- cord-276598-tm0yj2sn 1058 24 , , , cord-276598-tm0yj2sn 1058 25 tetraethylpyrophosphate tetraethylpyrophosphate NNP cord-276598-tm0yj2sn 1058 26 ( ( -LRB- cord-276598-tm0yj2sn 1058 27 tEPyP tEPyP NNP cord-276598-tm0yj2sn 1058 28 ) ) -RRB- cord-276598-tm0yj2sn 1058 29 , , , cord-276598-tm0yj2sn 1058 30 triphenylphosphate triphenylphosphate NNP cord-276598-tm0yj2sn 1058 31 ( ( -LRB- cord-276598-tm0yj2sn 1058 32 tPPO tPPO NNP cord-276598-tm0yj2sn 1058 33 ) ) -RRB- cord-276598-tm0yj2sn 1058 34 , , , cord-276598-tm0yj2sn 1058 35 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine CD cord-276598-tm0yj2sn 1058 36 ( ( -LRB- cord-276598-tm0yj2sn 1058 37 DBU DBU NNP cord-276598-tm0yj2sn 1058 38 ) ) -RRB- cord-276598-tm0yj2sn 1058 39 , , . cord-276598-tm0yj2sn 1059 1 matrix matrix NN cord-276598-tm0yj2sn 1059 2 - - HYPH cord-276598-tm0yj2sn 1059 3 assisted assist VBN cord-276598-tm0yj2sn 1059 4 laser laser NN cord-276598-tm0yj2sn 1059 5 desorption desorption NN cord-276598-tm0yj2sn 1059 6 - - HYPH cord-276598-tm0yj2sn 1059 7 ionization ionization NN cord-276598-tm0yj2sn 1059 8 time time NN cord-276598-tm0yj2sn 1059 9 - - HYPH cord-276598-tm0yj2sn 1059 10 of of IN cord-276598-tm0yj2sn 1059 11 - - HYPH cord-276598-tm0yj2sn 1059 12 flight flight NN cord-276598-tm0yj2sn 1059 13 mass mass NN cord-276598-tm0yj2sn 1059 14 spectrometry spectrometry NN cord-276598-tm0yj2sn 1059 15 ( ( -LRB- cord-276598-tm0yj2sn 1059 16 MALDI MALDI NNP cord-276598-tm0yj2sn 1059 17 - - HYPH cord-276598-tm0yj2sn 1059 18 TOF TOF NNP cord-276598-tm0yj2sn 1059 19 MS MS NNP cord-276598-tm0yj2sn 1059 20 ) ) -RRB- cord-276598-tm0yj2sn 1059 21 , , , cord-276598-tm0yj2sn 1059 22 task task NN cord-276598-tm0yj2sn 1059 23 specific specific JJ cord-276598-tm0yj2sn 1059 24 ionic ionic JJ cord-276598-tm0yj2sn 1059 25 liquid liquid NN cord-276598-tm0yj2sn 1059 26 ( ( -LRB- cord-276598-tm0yj2sn 1059 27 TSIL TSIL NNP cord-276598-tm0yj2sn 1059 28 ) ) -RRB- cord-276598-tm0yj2sn 1059 29 , , , cord-276598-tm0yj2sn 1059 30 phosphorodiamidate phosphorodiamidate NNP cord-276598-tm0yj2sn 1059 31 ( ( -LRB- cord-276598-tm0yj2sn 1059 32 N N NNP cord-276598-tm0yj2sn 1059 33 - - HYPH cord-276598-tm0yj2sn 1059 34 P P NNP cord-276598-tm0yj2sn 1059 35 - - HYPH cord-276598-tm0yj2sn 1059 36 N N NNP cord-276598-tm0yj2sn 1059 37 ) ) -RRB- cord-276598-tm0yj2sn 1059 38 , , , cord-276598-tm0yj2sn 1059 39 phenyl phenyl NNP cord-276598-tm0yj2sn 1059 40 dichlorophosphate dichlorophosphate VBP cord-276598-tm0yj2sn 1059 41 ( ( -LRB- cord-276598-tm0yj2sn 1059 42 PdCP PdCP NNP cord-276598-tm0yj2sn 1059 43 ) ) -RRB- cord-276598-tm0yj2sn 1059 44 , , , cord-276598-tm0yj2sn 1059 45 diphenylchlorophosphate diphenylchlorophosphate NNP cord-276598-tm0yj2sn 1059 46 ( ( -LRB- cord-276598-tm0yj2sn 1060 1 dPCP dPCP NNP cord-276598-tm0yj2sn 1060 2 ) ) -RRB- cord-276598-tm0yj2sn 1060 3 , , , cord-276598-tm0yj2sn 1060 4 tert tert NN cord-276598-tm0yj2sn 1060 5 - - HYPH cord-276598-tm0yj2sn 1060 6 butyl butyl NN cord-276598-tm0yj2sn 1060 7 hydroperoxide hydroperoxide NN cord-276598-tm0yj2sn 1060 8 ( ( -LRB- cord-276598-tm0yj2sn 1060 9 TBHP TBHP NNP cord-276598-tm0yj2sn 1060 10 ) ) -RRB- cord-276598-tm0yj2sn 1060 11 . . . cord-276598-tm0yj2sn 1061 1 There there EX cord-276598-tm0yj2sn 1061 2 were be VBD cord-276598-tm0yj2sn 1061 3 no no DT cord-276598-tm0yj2sn 1061 4 suggested suggest VBN cord-276598-tm0yj2sn 1061 5 mechanisms mechanism NNS cord-276598-tm0yj2sn 1061 6 for for IN cord-276598-tm0yj2sn 1061 7 the the DT cord-276598-tm0yj2sn 1061 8 reaction reaction NN cord-276598-tm0yj2sn 1061 9 in in IN cord-276598-tm0yj2sn 1061 10 the the DT cord-276598-tm0yj2sn 1061 11 report report NN cord-276598-tm0yj2sn 1061 12 by by IN cord-276598-tm0yj2sn 1061 13 Wang Wang NNP cord-276598-tm0yj2sn 1061 14 et et NNP cord-276598-tm0yj2sn 1061 15 al al NNP cord-276598-tm0yj2sn 1061 16 . . . cord-276598-tm0yj2sn 1062 1 [ [ -LRB- cord-276598-tm0yj2sn 1062 2 104 104 CD cord-276598-tm0yj2sn 1062 3 ] ] -RRB- cord-276598-tm0yj2sn 1062 4 . . . cord-276598-tm0yj2sn 1063 1 However however RB cord-276598-tm0yj2sn 1063 2 , , , cord-276598-tm0yj2sn 1063 3 the the DT cord-276598-tm0yj2sn 1063 4 results result NNS cord-276598-tm0yj2sn 1063 5 of of IN cord-276598-tm0yj2sn 1063 6 the the DT cord-276598-tm0yj2sn 1063 7 reagent reagent NN cord-276598-tm0yj2sn 1063 8 screening screening NN cord-276598-tm0yj2sn 1063 9 for for IN cord-276598-tm0yj2sn 1063 10 the the DT cord-276598-tm0yj2sn 1063 11 reaction reaction NN cord-276598-tm0yj2sn 1063 12 had have VBD cord-276598-tm0yj2sn 1063 13 suggested suggest VBN cord-276598-tm0yj2sn 1063 14 that that IN cord-276598-tm0yj2sn 1063 15 other other JJ cord-276598-tm0yj2sn 1063 16 transition transition NN cord-276598-tm0yj2sn 1063 17 metal metal NN cord-276598-tm0yj2sn 1063 18 catalysts catalyst NNS cord-276598-tm0yj2sn 1063 19 ( ( -LRB- cord-276598-tm0yj2sn 1063 20 e.g. e.g. RB cord-276598-tm0yj2sn 1063 21 , , , cord-276598-tm0yj2sn 1063 22 CoBr2 CoBr2 NNS cord-276598-tm0yj2sn 1063 23 ) ) -RRB- cord-276598-tm0yj2sn 1063 24 and and CC cord-276598-tm0yj2sn 1063 25 other other JJ cord-276598-tm0yj2sn 1063 26 Cu Cu NNP cord-276598-tm0yj2sn 1063 27 catalysts catalyst NNS cord-276598-tm0yj2sn 1063 28 ( ( -LRB- cord-276598-tm0yj2sn 1063 29 e.g. e.g. RB cord-276598-tm0yj2sn 1063 30 , , , cord-276598-tm0yj2sn 1063 31 Cu(OAc)2·H2O Cu(OAc)2·H2O NNP cord-276598-tm0yj2sn 1063 32 ) ) -RRB- cord-276598-tm0yj2sn 1063 33 were be VBD cord-276598-tm0yj2sn 1063 34 inactive inactive JJ cord-276598-tm0yj2sn 1063 35 or or CC cord-276598-tm0yj2sn 1063 36 inefficient inefficient JJ cord-276598-tm0yj2sn 1063 37 for for IN cord-276598-tm0yj2sn 1063 38 the the DT cord-276598-tm0yj2sn 1063 39 catalysis catalysis NN cord-276598-tm0yj2sn 1063 40 . . . cord-276598-tm0yj2sn 1064 1 It -PRON- PRP cord-276598-tm0yj2sn 1064 2 was be VBD cord-276598-tm0yj2sn 1064 3 further further RB cord-276598-tm0yj2sn 1064 4 suggested suggest VBN cord-276598-tm0yj2sn 1064 5 that that IN cord-276598-tm0yj2sn 1064 6 although although IN cord-276598-tm0yj2sn 1064 7 a a DT cord-276598-tm0yj2sn 1064 8 CuCl CuCl NNP cord-276598-tm0yj2sn 1064 9 catalyst catalyst NN cord-276598-tm0yj2sn 1064 10 enabled enable VBD cord-276598-tm0yj2sn 1064 11 reaction reaction NN cord-276598-tm0yj2sn 1064 12 , , , cord-276598-tm0yj2sn 1064 13 it -PRON- PRP cord-276598-tm0yj2sn 1064 14 was be VBD cord-276598-tm0yj2sn 1064 15 not not RB cord-276598-tm0yj2sn 1064 16 as as RB cord-276598-tm0yj2sn 1064 17 effective effective JJ cord-276598-tm0yj2sn 1064 18 as as IN cord-276598-tm0yj2sn 1064 19 CuBr CuBr NNP cord-276598-tm0yj2sn 1064 20 and and CC cord-276598-tm0yj2sn 1064 21 conducting conduct VBG cord-276598-tm0yj2sn 1064 22 the the DT cord-276598-tm0yj2sn 1064 23 reaction reaction NN cord-276598-tm0yj2sn 1064 24 under under IN cord-276598-tm0yj2sn 1064 25 anaerobic anaerobic JJ cord-276598-tm0yj2sn 1064 26 conditions condition NNS cord-276598-tm0yj2sn 1064 27 ( ( -LRB- cord-276598-tm0yj2sn 1064 28 e.g. e.g. RB cord-276598-tm0yj2sn 1064 29 , , , cord-276598-tm0yj2sn 1064 30 under under IN cord-276598-tm0yj2sn 1064 31 N2 N2 NNP cord-276598-tm0yj2sn 1064 32 ) ) -RRB- cord-276598-tm0yj2sn 1064 33 did do VBD cord-276598-tm0yj2sn 1064 34 not not RB cord-276598-tm0yj2sn 1064 35 lead lead VB cord-276598-tm0yj2sn 1064 36 to to IN cord-276598-tm0yj2sn 1064 37 the the DT cord-276598-tm0yj2sn 1064 38 desired desire VBN cord-276598-tm0yj2sn 1064 39 product product NN cord-276598-tm0yj2sn 1064 40 . . . cord-276598-tm0yj2sn 1065 1 In in IN cord-276598-tm0yj2sn 1065 2 the the DT cord-276598-tm0yj2sn 1065 3 Fe3O4@MgO Fe3O4@MgO NNP cord-276598-tm0yj2sn 1065 4 nanoparticle nanoparticle NN cord-276598-tm0yj2sn 1065 5 - - HYPH cord-276598-tm0yj2sn 1065 6 mediated mediate VBN cord-276598-tm0yj2sn 1065 7 synthesis synthesis NN cord-276598-tm0yj2sn 1065 8 of of IN cord-276598-tm0yj2sn 1065 9 P p NN cord-276598-tm0yj2sn 1065 10 - - HYPH cord-276598-tm0yj2sn 1065 11 Ns Ns NNP cord-276598-tm0yj2sn 1065 12 as as IN cord-276598-tm0yj2sn 1065 13 per per IN cord-276598-tm0yj2sn 1065 14 the the DT cord-276598-tm0yj2sn 1065 15 procedure procedure NN cord-276598-tm0yj2sn 1065 16 reported report VBN cord-276598-tm0yj2sn 1065 17 by by IN cord-276598-tm0yj2sn 1065 18 Habibi Habibi NNP cord-276598-tm0yj2sn 1065 19 et et NNP cord-276598-tm0yj2sn 1065 20 al al NNP cord-276598-tm0yj2sn 1065 21 . . . cord-276598-tm0yj2sn 1066 1 [ [ -LRB- cord-276598-tm0yj2sn 1066 2 105 105 CD cord-276598-tm0yj2sn 1066 3 ] ] -RRB- cord-276598-tm0yj2sn 1066 4 , , , cord-276598-tm0yj2sn 1066 5 the the DT cord-276598-tm0yj2sn 1066 6 mechanism mechanism NN cord-276598-tm0yj2sn 1066 7 involves involve VBZ cord-276598-tm0yj2sn 1066 8 the the DT cord-276598-tm0yj2sn 1066 9 formation formation NN cord-276598-tm0yj2sn 1066 10 of of IN cord-276598-tm0yj2sn 1066 11 the the DT cord-276598-tm0yj2sn 1067 1 ( ( -LRB- cord-276598-tm0yj2sn 1067 2 RO)2P(O)Cl RO)2P(O)Cl NNP cord-276598-tm0yj2sn 1067 3 ( ( -LRB- cord-276598-tm0yj2sn 1067 4 dACP dacp NN cord-276598-tm0yj2sn 1067 5 ; ; : cord-276598-tm0yj2sn 1067 6 R r NN cord-276598-tm0yj2sn 1067 7 = = NN cord-276598-tm0yj2sn 1067 8 alkyl alkyl NN cord-276598-tm0yj2sn 1067 9 ) ) -RRB- cord-276598-tm0yj2sn 1068 1 intermediate intermediate JJ cord-276598-tm0yj2sn 1068 2 from from IN cord-276598-tm0yj2sn 1068 3 the the DT cord-276598-tm0yj2sn 1068 4 reaction reaction NN cord-276598-tm0yj2sn 1068 5 of of IN cord-276598-tm0yj2sn 1068 6 dialkyl dialkyl NNP cord-276598-tm0yj2sn 1068 7 H H NNP cord-276598-tm0yj2sn 1068 8 - - HYPH cord-276598-tm0yj2sn 1068 9 phosphonate phosphonate NNP cord-276598-tm0yj2sn 1068 10 ( ( -LRB- cord-276598-tm0yj2sn 1068 11 ( ( -LRB- cord-276598-tm0yj2sn 1068 12 OR)2P(O)H or)2p(o)h CD cord-276598-tm0yj2sn 1068 13 , , , cord-276598-tm0yj2sn 1068 14 R r NN cord-276598-tm0yj2sn 1068 15 = = NN cord-276598-tm0yj2sn 1068 16 alkyl alkyl NN cord-276598-tm0yj2sn 1068 17 ) ) -RRB- cord-276598-tm0yj2sn 1068 18 with with IN cord-276598-tm0yj2sn 1068 19 CCl4 CCl4 NNP cord-276598-tm0yj2sn 1068 20 ( ( -LRB- cord-276598-tm0yj2sn 1068 21 Scheme scheme NN cord-276598-tm0yj2sn 1068 22 28 28 CD cord-276598-tm0yj2sn 1068 23 ) ) -RRB- cord-276598-tm0yj2sn 1068 24 . . . cord-276598-tm0yj2sn 1069 1 Following follow VBG cord-276598-tm0yj2sn 1069 2 , , , cord-276598-tm0yj2sn 1069 3 the the DT cord-276598-tm0yj2sn 1069 4 amine amine NN cord-276598-tm0yj2sn 1069 5 in in IN cord-276598-tm0yj2sn 1069 6 the the DT cord-276598-tm0yj2sn 1069 7 presence presence NN cord-276598-tm0yj2sn 1069 8 of of IN cord-276598-tm0yj2sn 1069 9 Fe3O4@MgO Fe3O4@MgO NNP cord-276598-tm0yj2sn 1069 10 nanoparticles nanoparticle NNS cord-276598-tm0yj2sn 1069 11 couples couple NNS cord-276598-tm0yj2sn 1069 12 with with IN cord-276598-tm0yj2sn 1069 13 the the DT cord-276598-tm0yj2sn 1069 14 dACP dacp NN cord-276598-tm0yj2sn 1069 15 by by IN cord-276598-tm0yj2sn 1069 16 nucleophilic nucleophilic JJ cord-276598-tm0yj2sn 1069 17 substitution substitution NN cord-276598-tm0yj2sn 1069 18 to to TO cord-276598-tm0yj2sn 1069 19 give give VB cord-276598-tm0yj2sn 1069 20 the the DT cord-276598-tm0yj2sn 1069 21 P P NNP cord-276598-tm0yj2sn 1069 22 - - HYPH cord-276598-tm0yj2sn 1069 23 N n CD cord-276598-tm0yj2sn 1069 24 product product NN cord-276598-tm0yj2sn 1069 25 , , , cord-276598-tm0yj2sn 1069 26 eliminating eliminate VBG cord-276598-tm0yj2sn 1069 27 HCl HCl NNP cord-276598-tm0yj2sn 1069 28 . . . cord-276598-tm0yj2sn 1070 1 Scheme scheme NN cord-276598-tm0yj2sn 1070 2 28 28 CD cord-276598-tm0yj2sn 1070 3 . . . cord-276598-tm0yj2sn 1071 1 Proposed propose VBN cord-276598-tm0yj2sn 1071 2 mechanism mechanism NN cord-276598-tm0yj2sn 1071 3 for for IN cord-276598-tm0yj2sn 1071 4 the the DT cord-276598-tm0yj2sn 1071 5 Fe3O4@MgO Fe3O4@MgO NNP cord-276598-tm0yj2sn 1071 6 nanoparticle nanoparticle NN cord-276598-tm0yj2sn 1071 7 - - HYPH cord-276598-tm0yj2sn 1071 8 mediated mediate VBN cord-276598-tm0yj2sn 1071 9 synthesis synthesis NN cord-276598-tm0yj2sn 1071 10 of of IN cord-276598-tm0yj2sn 1071 11 phosphoramidates phosphoramidates NNP cord-276598-tm0yj2sn 1071 12 . . . cord-276598-tm0yj2sn 1072 1 Proposed propose VBN cord-276598-tm0yj2sn 1072 2 mechanism mechanism NN cord-276598-tm0yj2sn 1072 3 for for IN cord-276598-tm0yj2sn 1072 4 the the DT cord-276598-tm0yj2sn 1072 5 copper copper NN cord-276598-tm0yj2sn 1072 6 catalyzed catalyze VBN cord-276598-tm0yj2sn 1072 7 oxidative oxidative JJ cord-276598-tm0yj2sn 1072 8 cross cross NN cord-276598-tm0yj2sn 1072 9 - - NN cord-276598-tm0yj2sn 1072 10 coupling coupling NN cord-276598-tm0yj2sn 1072 11 of of IN cord-276598-tm0yj2sn 1072 12 disubstituted disubstituted JJ cord-276598-tm0yj2sn 1072 13 H h NN cord-276598-tm0yj2sn 1072 14 - - HYPH cord-276598-tm0yj2sn 1072 15 phosphonates phosphonate NNS cord-276598-tm0yj2sn 1072 16 and and CC cord-276598-tm0yj2sn 1072 17 amines amine NNS cord-276598-tm0yj2sn 1072 18 to to TO cord-276598-tm0yj2sn 1072 19 produce produce VB cord-276598-tm0yj2sn 1072 20 phosphoramidates phosphoramidate NNS cord-276598-tm0yj2sn 1072 21 . . . cord-276598-tm0yj2sn 1073 1 There there EX cord-276598-tm0yj2sn 1073 2 were be VBD cord-276598-tm0yj2sn 1073 3 no no DT cord-276598-tm0yj2sn 1073 4 suggested suggest VBN cord-276598-tm0yj2sn 1073 5 mechanisms mechanism NNS cord-276598-tm0yj2sn 1073 6 for for IN cord-276598-tm0yj2sn 1073 7 the the DT cord-276598-tm0yj2sn 1073 8 reaction reaction NN cord-276598-tm0yj2sn 1073 9 in in IN cord-276598-tm0yj2sn 1073 10 the the DT cord-276598-tm0yj2sn 1073 11 report report NN cord-276598-tm0yj2sn 1073 12 by by IN cord-276598-tm0yj2sn 1073 13 Wang Wang NNP cord-276598-tm0yj2sn 1073 14 et et NNP cord-276598-tm0yj2sn 1073 15 al al NNP cord-276598-tm0yj2sn 1073 16 . . . cord-276598-tm0yj2sn 1074 1 [ [ -LRB- cord-276598-tm0yj2sn 1074 2 104 104 CD cord-276598-tm0yj2sn 1074 3 ] ] -RRB- cord-276598-tm0yj2sn 1074 4 . . . cord-276598-tm0yj2sn 1075 1 However however RB cord-276598-tm0yj2sn 1075 2 , , , cord-276598-tm0yj2sn 1075 3 the the DT cord-276598-tm0yj2sn 1075 4 results result NNS cord-276598-tm0yj2sn 1075 5 of of IN cord-276598-tm0yj2sn 1075 6 the the DT cord-276598-tm0yj2sn 1075 7 reagent reagent NN cord-276598-tm0yj2sn 1075 8 screening screening NN cord-276598-tm0yj2sn 1075 9 for for IN cord-276598-tm0yj2sn 1075 10 the the DT cord-276598-tm0yj2sn 1075 11 reaction reaction NN cord-276598-tm0yj2sn 1075 12 had have VBD cord-276598-tm0yj2sn 1075 13 suggested suggest VBN cord-276598-tm0yj2sn 1075 14 that that IN cord-276598-tm0yj2sn 1075 15 other other JJ cord-276598-tm0yj2sn 1075 16 transition transition NN cord-276598-tm0yj2sn 1075 17 metal metal NN cord-276598-tm0yj2sn 1075 18 catalysts catalyst NNS cord-276598-tm0yj2sn 1075 19 ( ( -LRB- cord-276598-tm0yj2sn 1075 20 e.g. e.g. RB cord-276598-tm0yj2sn 1075 21 , , , cord-276598-tm0yj2sn 1075 22 CoBr CoBr NNP cord-276598-tm0yj2sn 1075 23 2 2 CD cord-276598-tm0yj2sn 1075 24 ) ) -RRB- cord-276598-tm0yj2sn 1075 25 and and CC cord-276598-tm0yj2sn 1075 26 other other JJ cord-276598-tm0yj2sn 1075 27 Cu Cu NNP cord-276598-tm0yj2sn 1075 28 catalysts catalyst NNS cord-276598-tm0yj2sn 1075 29 ( ( -LRB- cord-276598-tm0yj2sn 1075 30 e.g. e.g. RB cord-276598-tm0yj2sn 1075 31 , , , cord-276598-tm0yj2sn 1075 32 Cu(OAc Cu(OAc NNS cord-276598-tm0yj2sn 1075 33 ) ) -RRB- cord-276598-tm0yj2sn 1075 34 2 2 CD cord-276598-tm0yj2sn 1075 35 · · NFP cord-276598-tm0yj2sn 1075 36 H h NN cord-276598-tm0yj2sn 1075 37 2 2 CD cord-276598-tm0yj2sn 1075 38 O o NN cord-276598-tm0yj2sn 1075 39 ) ) -RRB- cord-276598-tm0yj2sn 1075 40 were be VBD cord-276598-tm0yj2sn 1075 41 inactive inactive JJ cord-276598-tm0yj2sn 1075 42 or or CC cord-276598-tm0yj2sn 1075 43 inefficient inefficient JJ cord-276598-tm0yj2sn 1075 44 for for IN cord-276598-tm0yj2sn 1075 45 the the DT cord-276598-tm0yj2sn 1075 46 catalysis catalysis NN cord-276598-tm0yj2sn 1075 47 . . . cord-276598-tm0yj2sn 1076 1 It -PRON- PRP cord-276598-tm0yj2sn 1076 2 was be VBD cord-276598-tm0yj2sn 1076 3 further further RB cord-276598-tm0yj2sn 1076 4 suggested suggest VBN cord-276598-tm0yj2sn 1076 5 that that IN cord-276598-tm0yj2sn 1076 6 although although IN cord-276598-tm0yj2sn 1076 7 a a DT cord-276598-tm0yj2sn 1076 8 CuCl CuCl NNP cord-276598-tm0yj2sn 1076 9 catalyst catalyst NN cord-276598-tm0yj2sn 1076 10 enabled enable VBD cord-276598-tm0yj2sn 1076 11 reaction reaction NN cord-276598-tm0yj2sn 1076 12 , , , cord-276598-tm0yj2sn 1076 13 it -PRON- PRP cord-276598-tm0yj2sn 1076 14 was be VBD cord-276598-tm0yj2sn 1076 15 not not RB cord-276598-tm0yj2sn 1076 16 as as RB cord-276598-tm0yj2sn 1076 17 effective effective JJ cord-276598-tm0yj2sn 1076 18 as as IN cord-276598-tm0yj2sn 1076 19 CuBr CuBr NNP cord-276598-tm0yj2sn 1076 20 and and CC cord-276598-tm0yj2sn 1076 21 conducting conduct VBG cord-276598-tm0yj2sn 1076 22 the the DT cord-276598-tm0yj2sn 1076 23 reaction reaction NN cord-276598-tm0yj2sn 1076 24 under under IN cord-276598-tm0yj2sn 1076 25 anaerobic anaerobic JJ cord-276598-tm0yj2sn 1076 26 conditions condition NNS cord-276598-tm0yj2sn 1076 27 ( ( -LRB- cord-276598-tm0yj2sn 1076 28 e.g. e.g. RB cord-276598-tm0yj2sn 1076 29 , , , cord-276598-tm0yj2sn 1076 30 under under IN cord-276598-tm0yj2sn 1076 31 N n CD cord-276598-tm0yj2sn 1076 32 2 2 CD cord-276598-tm0yj2sn 1076 33 ) ) -RRB- cord-276598-tm0yj2sn 1076 34 did do VBD cord-276598-tm0yj2sn 1076 35 not not RB cord-276598-tm0yj2sn 1076 36 lead lead VB cord-276598-tm0yj2sn 1076 37 to to IN cord-276598-tm0yj2sn 1076 38 the the DT cord-276598-tm0yj2sn 1076 39 desired desire VBN cord-276598-tm0yj2sn 1076 40 product product NN cord-276598-tm0yj2sn 1076 41 . . . cord-276598-tm0yj2sn 1077 1 In in IN cord-276598-tm0yj2sn 1077 2 the the DT cord-276598-tm0yj2sn 1077 3 Fe Fe NNP cord-276598-tm0yj2sn 1077 4 3 3 CD cord-276598-tm0yj2sn 1077 5 O o NN cord-276598-tm0yj2sn 1077 6 4 4 CD cord-276598-tm0yj2sn 1077 7 @MgO @mgo NN cord-276598-tm0yj2sn 1077 8 nanoparticle nanoparticle NN cord-276598-tm0yj2sn 1077 9 - - HYPH cord-276598-tm0yj2sn 1077 10 mediated mediate VBN cord-276598-tm0yj2sn 1077 11 synthesis synthesis NN cord-276598-tm0yj2sn 1077 12 of of IN cord-276598-tm0yj2sn 1077 13 P p NN cord-276598-tm0yj2sn 1077 14 - - HYPH cord-276598-tm0yj2sn 1077 15 Ns Ns NNP cord-276598-tm0yj2sn 1077 16 as as IN cord-276598-tm0yj2sn 1077 17 per per IN cord-276598-tm0yj2sn 1077 18 the the DT cord-276598-tm0yj2sn 1077 19 procedure procedure NN cord-276598-tm0yj2sn 1077 20 reported report VBN cord-276598-tm0yj2sn 1077 21 by by IN cord-276598-tm0yj2sn 1077 22 Habibi Habibi NNP cord-276598-tm0yj2sn 1077 23 et et NNP cord-276598-tm0yj2sn 1077 24 al al NNP cord-276598-tm0yj2sn 1077 25 . . . cord-276598-tm0yj2sn 1078 1 [ [ -LRB- cord-276598-tm0yj2sn 1078 2 105 105 CD cord-276598-tm0yj2sn 1078 3 ] ] -RRB- cord-276598-tm0yj2sn 1078 4 , , , cord-276598-tm0yj2sn 1078 5 the the DT cord-276598-tm0yj2sn 1078 6 mechanism mechanism NN cord-276598-tm0yj2sn 1078 7 involves involve VBZ cord-276598-tm0yj2sn 1078 8 the the DT cord-276598-tm0yj2sn 1078 9 formation formation NN cord-276598-tm0yj2sn 1078 10 of of IN cord-276598-tm0yj2sn 1078 11 the the DT cord-276598-tm0yj2sn 1078 12 ( ( -LRB- cord-276598-tm0yj2sn 1078 13 RO ro NN cord-276598-tm0yj2sn 1078 14 ) ) -RRB- cord-276598-tm0yj2sn 1078 15 2 2 CD cord-276598-tm0yj2sn 1078 16 oxidized oxidize VBN cord-276598-tm0yj2sn 1078 17 to to TO cord-276598-tm0yj2sn 1078 18 form form VB cord-276598-tm0yj2sn 1078 19 the the DT cord-276598-tm0yj2sn 1078 20 Cu(III)-amine Cu(III)-amine NNP cord-276598-tm0yj2sn 1078 21 - - HYPH cord-276598-tm0yj2sn 1078 22 phosphonate phosphonate JJ cord-276598-tm0yj2sn 1078 23 complex complex NN cord-276598-tm0yj2sn 1078 24 , , , cord-276598-tm0yj2sn 1078 25 which which WDT cord-276598-tm0yj2sn 1078 26 undergoes undergo VBZ cord-276598-tm0yj2sn 1078 27 reductive reductive JJ cord-276598-tm0yj2sn 1078 28 elimination elimination NN cord-276598-tm0yj2sn 1078 29 of of IN cord-276598-tm0yj2sn 1078 30 the the DT cord-276598-tm0yj2sn 1078 31 copper copper NN cord-276598-tm0yj2sn 1078 32 catalyst catalyst NN cord-276598-tm0yj2sn 1078 33 to to TO cord-276598-tm0yj2sn 1078 34 yield yield VB cord-276598-tm0yj2sn 1078 35 the the DT cord-276598-tm0yj2sn 1078 36 desired desire VBN cord-276598-tm0yj2sn 1078 37 P p NN cord-276598-tm0yj2sn 1078 38 - - HYPH cord-276598-tm0yj2sn 1078 39 N. n. NN cord-276598-tm0yj2sn 1079 1 Although although IN cord-276598-tm0yj2sn 1079 2 this this DT cord-276598-tm0yj2sn 1079 3 mechanism mechanism NN cord-276598-tm0yj2sn 1079 4 seems seem VBZ cord-276598-tm0yj2sn 1079 5 plausible plausible JJ cord-276598-tm0yj2sn 1079 6 , , , cord-276598-tm0yj2sn 1079 7 it -PRON- PRP cord-276598-tm0yj2sn 1079 8 could could MD cord-276598-tm0yj2sn 1079 9 not not RB cord-276598-tm0yj2sn 1079 10 easily easily RB cord-276598-tm0yj2sn 1079 11 explain explain VB cord-276598-tm0yj2sn 1079 12 the the DT cord-276598-tm0yj2sn 1079 13 formation formation NN cord-276598-tm0yj2sn 1079 14 of of IN cord-276598-tm0yj2sn 1079 15 the the DT cord-276598-tm0yj2sn 1079 16 side side NN cord-276598-tm0yj2sn 1079 17 products product NNS cord-276598-tm0yj2sn 1079 18 . . . cord-276598-tm0yj2sn 1080 1 Proposed propose VBN cord-276598-tm0yj2sn 1080 2 mechanism mechanism NN cord-276598-tm0yj2sn 1080 3 for for IN cord-276598-tm0yj2sn 1080 4 the the DT cord-276598-tm0yj2sn 1080 5 copper copper NN cord-276598-tm0yj2sn 1080 6 catalyzed catalyze VBN cord-276598-tm0yj2sn 1080 7 oxidative oxidative JJ cord-276598-tm0yj2sn 1080 8 cross cross NN cord-276598-tm0yj2sn 1080 9 - - NN cord-276598-tm0yj2sn 1080 10 coupling coupling NN cord-276598-tm0yj2sn 1080 11 of of IN cord-276598-tm0yj2sn 1080 12 disubstituted disubstituted JJ cord-276598-tm0yj2sn 1080 13 H h NN cord-276598-tm0yj2sn 1080 14 - - HYPH cord-276598-tm0yj2sn 1080 15 phosphonates phosphonate NNS cord-276598-tm0yj2sn 1080 16 and and CC cord-276598-tm0yj2sn 1080 17 amines amine NNS cord-276598-tm0yj2sn 1080 18 to to TO cord-276598-tm0yj2sn 1080 19 produce produce VB cord-276598-tm0yj2sn 1080 20 phosphoramidates phosphoramidate NNS cord-276598-tm0yj2sn 1080 21 . . . cord-276598-tm0yj2sn 1081 1 There there EX cord-276598-tm0yj2sn 1081 2 were be VBD cord-276598-tm0yj2sn 1081 3 no no DT cord-276598-tm0yj2sn 1081 4 suggested suggest VBN cord-276598-tm0yj2sn 1081 5 mechanisms mechanism NNS cord-276598-tm0yj2sn 1081 6 for for IN cord-276598-tm0yj2sn 1081 7 the the DT cord-276598-tm0yj2sn 1081 8 reaction reaction NN cord-276598-tm0yj2sn 1081 9 in in IN cord-276598-tm0yj2sn 1081 10 the the DT cord-276598-tm0yj2sn 1081 11 report report NN cord-276598-tm0yj2sn 1081 12 by by IN cord-276598-tm0yj2sn 1081 13 Wang Wang NNP cord-276598-tm0yj2sn 1081 14 et et NNP cord-276598-tm0yj2sn 1081 15 al al NNP cord-276598-tm0yj2sn 1081 16 . . . cord-276598-tm0yj2sn 1082 1 [ [ -LRB- cord-276598-tm0yj2sn 1082 2 104 104 CD cord-276598-tm0yj2sn 1082 3 ] ] -RRB- cord-276598-tm0yj2sn 1082 4 . . . cord-276598-tm0yj2sn 1083 1 However however RB cord-276598-tm0yj2sn 1083 2 , , , cord-276598-tm0yj2sn 1083 3 the the DT cord-276598-tm0yj2sn 1083 4 results result NNS cord-276598-tm0yj2sn 1083 5 of of IN cord-276598-tm0yj2sn 1083 6 the the DT cord-276598-tm0yj2sn 1083 7 reagent reagent NN cord-276598-tm0yj2sn 1083 8 screening screening NN cord-276598-tm0yj2sn 1083 9 for for IN cord-276598-tm0yj2sn 1083 10 the the DT cord-276598-tm0yj2sn 1083 11 reaction reaction NN cord-276598-tm0yj2sn 1083 12 had have VBD cord-276598-tm0yj2sn 1083 13 suggested suggest VBN cord-276598-tm0yj2sn 1083 14 that that IN cord-276598-tm0yj2sn 1083 15 other other JJ cord-276598-tm0yj2sn 1083 16 transition transition NN cord-276598-tm0yj2sn 1083 17 metal metal NN cord-276598-tm0yj2sn 1083 18 catalysts catalyst NNS cord-276598-tm0yj2sn 1083 19 ( ( -LRB- cord-276598-tm0yj2sn 1083 20 e.g. e.g. RB cord-276598-tm0yj2sn 1083 21 , , , cord-276598-tm0yj2sn 1083 22 CoBr2 CoBr2 NNS cord-276598-tm0yj2sn 1083 23 ) ) -RRB- cord-276598-tm0yj2sn 1083 24 and and CC cord-276598-tm0yj2sn 1083 25 other other JJ cord-276598-tm0yj2sn 1083 26 Cu Cu NNP cord-276598-tm0yj2sn 1083 27 catalysts catalyst NNS cord-276598-tm0yj2sn 1083 28 ( ( -LRB- cord-276598-tm0yj2sn 1083 29 e.g. e.g. RB cord-276598-tm0yj2sn 1083 30 , , , cord-276598-tm0yj2sn 1083 31 Cu(OAc)2·H2O Cu(OAc)2·H2O NNP cord-276598-tm0yj2sn 1083 32 ) ) -RRB- cord-276598-tm0yj2sn 1083 33 were be VBD cord-276598-tm0yj2sn 1083 34 inactive inactive JJ cord-276598-tm0yj2sn 1083 35 or or CC cord-276598-tm0yj2sn 1083 36 inefficient inefficient JJ cord-276598-tm0yj2sn 1083 37 for for IN cord-276598-tm0yj2sn 1083 38 the the DT cord-276598-tm0yj2sn 1083 39 catalysis catalysis NN cord-276598-tm0yj2sn 1083 40 . . . cord-276598-tm0yj2sn 1084 1 It -PRON- PRP cord-276598-tm0yj2sn 1084 2 was be VBD cord-276598-tm0yj2sn 1084 3 further further RB cord-276598-tm0yj2sn 1084 4 suggested suggest VBN cord-276598-tm0yj2sn 1084 5 that that IN cord-276598-tm0yj2sn 1084 6 although although IN cord-276598-tm0yj2sn 1084 7 a a DT cord-276598-tm0yj2sn 1084 8 CuCl CuCl NNP cord-276598-tm0yj2sn 1084 9 catalyst catalyst NN cord-276598-tm0yj2sn 1084 10 enabled enable VBD cord-276598-tm0yj2sn 1084 11 reaction reaction NN cord-276598-tm0yj2sn 1084 12 , , , cord-276598-tm0yj2sn 1084 13 it -PRON- PRP cord-276598-tm0yj2sn 1084 14 was be VBD cord-276598-tm0yj2sn 1084 15 not not RB cord-276598-tm0yj2sn 1084 16 as as RB cord-276598-tm0yj2sn 1084 17 effective effective JJ cord-276598-tm0yj2sn 1084 18 as as IN cord-276598-tm0yj2sn 1084 19 CuBr CuBr NNP cord-276598-tm0yj2sn 1084 20 and and CC cord-276598-tm0yj2sn 1084 21 conducting conduct VBG cord-276598-tm0yj2sn 1084 22 the the DT cord-276598-tm0yj2sn 1084 23 reaction reaction NN cord-276598-tm0yj2sn 1084 24 under under IN cord-276598-tm0yj2sn 1084 25 anaerobic anaerobic JJ cord-276598-tm0yj2sn 1084 26 conditions condition NNS cord-276598-tm0yj2sn 1084 27 ( ( -LRB- cord-276598-tm0yj2sn 1084 28 e.g. e.g. RB cord-276598-tm0yj2sn 1084 29 , , , cord-276598-tm0yj2sn 1084 30 under under IN cord-276598-tm0yj2sn 1084 31 N2 N2 NNP cord-276598-tm0yj2sn 1084 32 ) ) -RRB- cord-276598-tm0yj2sn 1084 33 did do VBD cord-276598-tm0yj2sn 1084 34 not not RB cord-276598-tm0yj2sn 1084 35 lead lead VB cord-276598-tm0yj2sn 1084 36 to to IN cord-276598-tm0yj2sn 1084 37 the the DT cord-276598-tm0yj2sn 1084 38 desired desire VBN cord-276598-tm0yj2sn 1084 39 product product NN cord-276598-tm0yj2sn 1084 40 . . . cord-276598-tm0yj2sn 1085 1 In in IN cord-276598-tm0yj2sn 1085 2 the the DT cord-276598-tm0yj2sn 1085 3 Fe3O4@MgO Fe3O4@MgO NNP cord-276598-tm0yj2sn 1085 4 nanoparticle nanoparticle NN cord-276598-tm0yj2sn 1085 5 - - HYPH cord-276598-tm0yj2sn 1085 6 mediated mediate VBN cord-276598-tm0yj2sn 1085 7 synthesis synthesis NN cord-276598-tm0yj2sn 1085 8 of of IN cord-276598-tm0yj2sn 1085 9 P p NN cord-276598-tm0yj2sn 1085 10 - - HYPH cord-276598-tm0yj2sn 1085 11 Ns Ns NNP cord-276598-tm0yj2sn 1085 12 as as IN cord-276598-tm0yj2sn 1085 13 per per IN cord-276598-tm0yj2sn 1085 14 the the DT cord-276598-tm0yj2sn 1085 15 procedure procedure NN cord-276598-tm0yj2sn 1085 16 reported report VBN cord-276598-tm0yj2sn 1085 17 by by IN cord-276598-tm0yj2sn 1085 18 Habibi Habibi NNP cord-276598-tm0yj2sn 1085 19 et et NNP cord-276598-tm0yj2sn 1085 20 al al NNP cord-276598-tm0yj2sn 1085 21 . . . cord-276598-tm0yj2sn 1086 1 [ [ -LRB- cord-276598-tm0yj2sn 1086 2 105 105 CD cord-276598-tm0yj2sn 1086 3 ] ] -RRB- cord-276598-tm0yj2sn 1086 4 , , , cord-276598-tm0yj2sn 1086 5 the the DT cord-276598-tm0yj2sn 1086 6 mechanism mechanism NN cord-276598-tm0yj2sn 1086 7 involves involve VBZ cord-276598-tm0yj2sn 1086 8 the the DT cord-276598-tm0yj2sn 1086 9 formation formation NN cord-276598-tm0yj2sn 1086 10 of of IN cord-276598-tm0yj2sn 1086 11 the the DT cord-276598-tm0yj2sn 1086 12 _SP