Regioselective electrochemical radical cascade cyclization of internal alkynes to selenated and trifluoromethylated dihydropyran

Abstract

Dihydropyran (DHP) compounds are not only found in natural products and bioactive molecules, but also serve as important precursors in organic synthesis. Nonetheless, traditional methods for the construction of such compounds are usually limited to disubstituted DHPs. To address this synthetic challenge, reported here is an efficient electrochemical strategy toward the selenated and trifluoromethylated DHP compounds. The reaction proceeded smoothly under mild electrolysis conditions. The broad substrate scope (>50 examples) and scalable synthesis demonstrated the complexity-building potential of the strategy. Initial mechanistic studies reveal that cyclization may involve a radical process. This protocol may promote the further development of diversified synthesis of multi-substituted dihydropyran.