Lewis base-promoted carbon–carbon sp3–sp3 coupling reactions of α-silyl silylethers

Abstract

A Lewis base-promoted addition of α-silyl silylethers to primary halides has been developed. This new carbon–carbon sp3–sp3 bond-forming process accesses an unconventional reactivity pattern (d1 synthon) from easily accessible precursors. The strategy accommodates a variety of primary alkyl, allylic and benzylic electrophiles and α-silyl silylethers. These d1 synthons have also been used in the synthesis of cross pinacol and benzil products. Mechanistic studies indicate significant intermolecular silyl group exchange during the reaction.