Visible Light-Induced Pd-Catalyzed Alkyl-Heck Reaction of Oximes

A visible light-induced palladium-catalyzed oxidative C–H alkylation of oximes has been developed. This mild protocol allows for an efficient atom economical C–C bond construction of alkyl-substituted oximes. A broad range of primary, secondary, and tertiary alkyl bromides and iodides, as well as a range of different formaldoximes, can efficiently undergo this transformation. The method features visible light-induced generation of nucleophilic hybrid alkyl Pd radical intermediates, which upon radical addition at the imine moiety and a subsequent β-hydrogen elimination deliver substituted imines.