Stereoselective one-pot synthesis of vinylsilanes from aromatic aldehydes

Vinylsilanes serve as convenient vinyl anion equivalents, but procedures for their stereoselective synthesis from aldehydes are scarce. A variety of aromatic aldehydes are converted to the corresponding vinylsilanes in a one-pot procedure involving the addition of (trimethylsilylmethyl)lithium to the aldehyde followed by treatment with Cp2TiCH2·AlMe2Cl (‘Tebbeʹs reagent’). Halide and alkoxide substituents are tolerated, and (E)-vinylsilanes are formed exclusively in good yield.