A convenient one-pot, organoaluminum mediated vinylsilane synthesis from non-enolizable ketones via the Peterson protocol

Vinylsilanes serve as convenient vinyl anion equivalents which have gained popularity over decades. A variety of non-enolizable aromatic ketones are converted to the corresponding vinylsilanes in a one-pot procedure involving the addition of (trimethylsilylmethyl)lithium to aromatic ketones followed by addition of diethylaluminum chloride and then small amounts of water. Halide and alkoxide substituents are tolerated, and this trans-stereoselective (broad generalization; the most sterically bulky group on the double bond is trans to the trimethylsilyl group) reaction affords vinylsilanes in good yield.