TBAF-initiated vinylation of aldehydes with trimethyl[(Z)-2-(phenylsulfanyl)-1-(trifluoromethyl)vinyl]silane

• We prepared trimethyl[( Z )−2-( phenylsulfanyl )−1-( trifluoromethyl ) vinyl ]silane as a useful CF 3 -containing building block in a simple and convenient manner. • The TBAF-initiated vinylation of aldehydes with the above silane afforded the corresponding 2-(trifluoromethyl)allyl alcohol derivatives in moderate to good yields. • This is the first practical demonstration of CF 3 -vinyl silane as an vinyl anion equivalent. The titular compound trifluromethylated vinylsilane was readily prepared in 84% yield from stereodefined ( Z )-2‑bromo-2-(trifluoromethyl)vinyl phenyl sulfide and chlorotrimethylsilane in the presence of magnesium under Barbier-type reaction conditions. The TBAF-initiated reaction of the vinylsilane and various aldehydes proceeded smoothly to give the corresponding 2-(trifluoromethyl)allyl alcohol derivatives in moderate to good yields.