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 [R 1 R 2 C O: R 1  = H; R 2  = Ph ( 1a ), 2,4-Cl 2 Ph ( 1b ), 2,4-Me 2 Ph ( 1c ): R 1  = Ph; R 2  = Ph ( 1d ), 4-ClPh ( 1e ), 4-MePh ( 2f ), 2,4-Me 2 Ph ( 1g ) undergo the deoxygenative silylation with HSiCl 3 in the presence of Bu 4 PCl at 150 °C within 1.0–1.5 h to give arylmethyltrichlorosilanes 2 (R 1 R 2 CH–SiCl 3 ) 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.