Synthesis of α‑Vinyltrialkoxysilanes via Nickel-Mediated Cross-Electrophile Coupling Reactions

Vinyltrialkoxysilanes are indispensable for organic synthesis, particularly cross-coupling reactions. Hydrosilylation of alkynes inevitably yields α- and β-isomers of vinyltrialkoxysilanes even with complex ligands and catalysts, limiting its usage in organic synthesis. We report the synthesis of α-vinyltrialkoxysilanes via cross-electrophile C­(sp²)–C­(sp²) coupling of bromoalkenes. The method is quite compatible with functional groups under milder reaction conditions. The gram-scale synthesis of most substrates is impressive. The intermediacy of vinyl iodide and radical escape rebound path are supported by mechanistic studies.