Deoxygenative silylation of aromatic carbonyl compounds with HSiCl3 in the presence of quaternary phosphonium chloride: A facile route to arylmethyltrichlorosilane

Abstract

Aromatic carbonyl compounds such as aromatic aldehydes and ketones [R1R2CO: R1=H; R2=Ph (1a), 2,4-Cl2Ph (1b), 2,4-Me2Ph (1c): R1=Ph; R2=Ph (1d), 4-ClPh (1e), 4-MePh (2f), 2,4-Me2Ph (1g) undergo the deoxygenative silylation with HSiCl3 in the presence of Bu4PCl at 150°C within 1.0–1.5h to give arylmethyltrichlorosilanes 2 (R1R2CH–SiCl3) in high yields (85–95%). The reactivity of aromatic carbonyl compounds decreases with increasing the electron withdrawing ability of substituent(s) on the benzene-ring. A highly efficient synthetic route to arylmethyltrichlorosilanes has been developed starting from aromatic aldehydes and ketones in this study.