Allylic C-H bond oxidative addition reactions, mediated by tris(oxazolinyl)borato rhodium(I) and iridium(I) species, provide the first step in a hydrocarbon functionalization sequence. The bond activation products To M MH(h 3 -C 8 H 13 ) (M = Rh (1), Ir (2)), To M MH(h 3 -C 3 H 5 ) (M = Rh (3), Ir (4)), and To M RhH(h 3 -C 3 H 4 Ph) (5) (To M = tris(4,4-dimethyl-2-oxazolinyl)phenylborate) are synthesized by reaction of Tl[To M ] and the corresponding metal olefin chloride dimers. Characterization of these group 9 allyl hydride complexes includes 1 H-15 N heteronuclear correlation NMR experiments that reveal through-metal magnetization transfer between metal hydride and the trans-coordinated oxazoline nitrogen. Furthermore, the oxazoline 15 N NMR chemical shifts are affected by the trans ligand, with the resonances for the group trans to hydride typically downfield of those trans to h 3 -allyl and tosylamide. These group 9 oxazolinylborate compounds have been studied to develop approaches for allylic functionalization. However, this possibility is generally limited by the tendency of the allyl hydride compounds to undergo olefin reductive elimination. Reductive elimination products are formed upon addition of ligands such as CO and CN t Bu.