Steric Promotion of Aromatic C–H Bond Activation in Primary Benzylamines

Abstract

ortho-Palladation of a sterically crowded primary benzylamine, α-phenylneopentylamine, was accomplished in a moderate yield of 50% in the reaction with the weakest of palladation agents (Li2PdCl4) under very mild conditions, due to a steric promotion of an aromatic C–H bond activation. The structure of dimer 1a thus formed and the palladacycle conformation were established on the basis of 1H-NMR spectroscopy of its mononuclear derivatives with [D5]pyridine (3a) and triphenylphosphane (4a), and an X-ray investi-gation of the latter.