Reactions of a N-acyliminium ion pool with benzylsilanes.: Implication of a radical/cation/radical cation chain mechanism involving oxidative C-Si bond cleavage

The reaction of a N-acyliminium ion pool with benzylsilane proceeds by a chain mechanism involving oxidative C-Si bond cleavage. A radical/cation/radical cation crossover mechanism involving single electron transfer has been proposed. The effective binary system consisting of a stoichiometric amount of a benzylsilane and a catalytic amount of a more easily oxidized benzylstannane has been developed.