Selective base-promoted synthesis of substituted selenophenes by carbocyclization of (Z)-benzylselenoenynes

Abstract

We herein described the synthesis of several 3-benzyl-2,5-diarylselenophene derivatives in moderate to good yields using (Z)-benzylselenoenynes as starting material in carbocyclization reactions. The reactions were carried out under mild conditions using only t-BuOK as base, in the complete absence of transition metals or additives. The cyclized 3-benzyl-2,5-diarylselenophenes obtained in the current protocol appear highly promising and attractive intermediates for the synthesis of polysubstituted selenophenes. For instance, 3-benzyl-2,5-diphenylselenophene was treated with Br₂ provided the corresponding 3-benzyl-4-bromo-2,5-diphenylselenophene in high yield. 4-Bromoselenophene derivative was applied as substrate in the palladium catalyzed cross-coupling reactions with boronic acids to give the Suzuki type products in excellent yields.