Palladium-Catalyzed Reductive Coupling of Styrenes and Organostannanes under Aerobic Conditions

Abstract

We report a highly regioselective PdII-catalyzed reductive coupling of an alkene with an organostannane using a tandem alcohol oxidation under aerobic conditions. Both aryl- and vinylstannanes are competent coupling partners with a variety of styrene derivatives. Mechanistic experiments support a tandem alcohol oxidation/alkene functionalization process. The ability to trap a palladium hydride derived from alcohol oxidation with an alkene provides a fundamentally different approach to cross-coupling reactions.