Photoredox-Catalyzed Intermolecular Remote C-H and C-C Vinylation via Iminyl Radicals

A unified strategy for intermolecular remote C(sp(3))-H and C-C vinylation of O-acyl oximes with vinyl boronic acids has been achieved. This strategy is enabled by photoreductive generation of iminyl radicals from O-aryl oximes under irradiation by visible light. The translocated carbon-centered radicals, which are generated from the iminyl radicals through 1,5-hydrogen atom transfer or C-C cleavage, can be vinylated with vinyl boronic acids. This strategy opens up a new approach to remote functionalization via C(sp(3))-H and C-C cleavage and provides an efficient and versatile solution to the synthesis of gamma-vinylation of ketones and nitriles.