Catalyst-Free and Solvent-Controlled Reductive Coupling of Activated Vinyl Triflates with Chlorotrimethylsilane by Magnesium Metal and Its Synthetic Application.

Vinylsilanes were directly prepared from the corresponding vinyl triflates under magnesium-promoted reductive conditions in THF with no transition metal catalyst, and gem-bis-silylated compounds were obtained in NMP. Investigation of the redox potential of starting materials and products suggested that reductive coupling reactions of vinyl triflates might be controlled by the reduction potential. A variety of gem-bis-silylated compounds and 3-silyladipic acid esters were easily synthesized in only two steps from vinyl triflates in high yields.