Reaction of Tplr(C2H4)(2) (Tp = tris-pyrazolylborate) with various chelating phosphine ligands has been explored. Reaction with bis-diphenylphosphinoethane leads to complete displacement of the Tp ligand. With bisdiphenylphosphinomethane, an intramolecular proton transfer from the methylene bridge to the iridium center occurs to give an iridium hydride complex formally resulting from oxidative C-H bond activation. Reaction with 2,2-bis(diphenylphosphino)propane (dppip) affords an Ir(I) complex formulated as kappa(2)-Tplr(dppip). Protonation of this Ir(I) complex gives a six coordinate Ir(III) hydride species.