Stannylation of alkyl chlorides with stannylpotassium

Abstract A stannylpotassium reagent, generated in situ from a readily available silylstannane and t-BuOK, is demonstrated to react smoothly with an alkyl bromide to give an alkylstannane in high yield. The superior nucleophilicity of the stannylpotassium reagent is illustrated in the efficient stannylative substitution of less reactive alkyl chlorides. Mechanistic studies reveal that the reaction proceeds through an ionic, SN2-type pathway.