Pincer ligands have become a reliable class of ligands in organometallic chemistry due to their ability to bind a metal center at three coordination sites, providing structural and electronic support to the metal complex. This dissertation describes the synthesis of late transition metal complexes containing a new PNP ligand comprised of a central pyrrole unit and di-iso-propylphosphine donors, bis[(dimethylamino)methyl]pyrrole, ((PNpyrP)H), 1.With this ligand, multiple transmetallation reagents including [(PNpyrP)Li]2 (7), (PNpyrP)Tl (8), and [(PNpyrP)Ag]2 (12) were synthesized in order to afford group 10 metal complexes of the form (PNpyrP)MCl (M = Ni (2), Pd (3), Pt (4)) as well as (PNpyrP)Ir(COD) (6) and (PNpyrP)Ru(PPh3)Cl (12). Compounds 2, 6, and 12 were the platform from which a library of transition metal (PNpyrP) complexes were generated and studied in stoichiometric and catalytic H-H and C-H bond activation reactions. The ability for the (PNpyrP) framework on late transition metals to engage in metal-ligand cooperation was assessed. We determined that nickel, iridium, and ruthenium complexes containing this ligand exhibit reversible structural changes of the backbone depending on the reaction environment (i.e. acid/base, atmosphere). Upon addition of HCl or Brookhart's acid ([H-(Et2O)2][BAr4F]), protonation of the ß-pyrrole position induces formation of an imine in the PNP backbone and a change in coordination mode of the N-donor from anionic to dative. An analogous rearrangement is observed upon addition of a hydride abstracting reagent ([Ph3C][PF6]) to 2 or 12 in which electrophilic aromatic addition to the ß-pyrrole position of the (PNpyrP) backbone occurs. Further, complex 12 was found to activate H2 at room temperature to afford (PNpyrP)HRu(PPh3)(H)Cl (44), a Ru(II) hydride compound containing the protonated pyrrole backbone. Overall, the ability of late transition metal complexes containing the (PNpyrP) ligand to undergo reversible structural changes was investigated as a means to leverage metal-ligand cooperation for the activation of small molecules and typically inert bonds.