Fluoride ion induced reactions of organosilanes: the preparation of mono- and dicarbonyl compounds from beta-ketosilanes

Beta-Ketosilanes react with a variety of C electrophiles in the presence of CsF to give mono- and dicarbonyl derivs. in reasonably good yields. Thus, 20.75 g dry CsF in 3 mL of dry THF was added dropwise, a soln. of BzCH2SiMe3 (1 g) and PhCH2Br (0.89 g) in 3 mL THF to give 0.76 g BzCH2CH2Ph. Among the nine compds. prepd. were BzCH:CHPh, Bz2(CH2)n (n = 1, 2), and 2-(benzoylvinyl)furan.