Preparation of substituted benzoyltrimethylsilanes and -germanes by the reaction of benzoyl chlorides with hexamethyldisilane or -digermane in the presence of palladium complexes as catalysts

Article abstract of DOI:10.1021/om00148a014

Benzoyltrimethylsilanes are prepared in moderate to good yields (24-81%) from the novel reaction of hexamethyldisilane with benzoyl chlorides, catalyzed by dichloro(η³-allyl)dipalladium(II) (1) and triethyl phosphite. The reaction tolerates a wide variety of meta and para substituents on the phenyl ring. Hexamethyldigermane and several bimetallic silicon-germaniums were also used in the reaction; the relative rates of group transfer from competitive benzoylation reactions are PhMe₂Ge > Me₃Ge > PhMe₂Si > Me₃Si. Ortho-substituted benzoyl chlorides and aliphatic acid chlorides gave lower yields of the corresponding acyltrimethylsilanes under the same reaction conditions.