Mg-promoted reductive coupling of aromatic carbonyl compounds with trimethylsilyl chloride and bis(chlorodimethylsilyl) compounds

Abstract

Mg-promoted reductive coupling of aromatic carbonyl compounds ( 1 ) with chlorosilanes, such as trimethylsilyl chloride (TMSCl: 2 ), 1,2-bis(chlorodimethylsilyl)ethane ( 3 ) and 1,5-dichlorohexamethyltrisiloxane ( 4 ), in N, N-dimethylformamide (DMF) at room temperature brought about selective and facile reductive formation of both of carbon–silicon and oxygen–silicon bonds to give the corresponding α-trimethylsilylalkyl trimethylsilyl ethers ( 5 ) and cyclic siloxanes ( 6 ), ( 7 ) in moderate to good yields, respectively. The present facile and selective coupling may be initiated through electron transfer from Mg metal to aromatic carbonyl compounds ( 1 ).