Electrochemical Synthesis of Organosilicon Compounds

Article abstract of DOI:10.1021/jo00371a016

Electrochemical reduction of allyl, aryl, and vinyl halides in the presence of a silylating agent (Me3SiCl, HMe2SiCl, and PhMe2SiCl) in a solution of tetraethylammonium tosylate in dimethylformamide (DMF) gave the corresponding organosilicon compounds.The regioselectivity of the reaction of allylic halides depends on the nature of the silylating agent.Trimethylsilyl and dimethylphenylsilyl groups were introduced to the less substituted end of the allyl group, whereas the dimethylsilyl group was introduced to both ends of the allyl group.High chemoselectivity of the present approach was demonstrated by selectivity monosilylations of p-bromoiodobenzene and p-bromocinnamyl chloride to obtain (p-bromophenyl)trimethylsilane and (p-bromocinnamyl)trimethylsilane, respectively.A mechanism involving a carbanion intermediate is suggested.