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

作　　者：Mingming Yu Tiantian Huang Lin Zhang Muhammad Shabbir Yuhan Gao Yi-Hung Chen Hong Yi Aiwen Lei 

机构地区：[1]The Institute for Advanced Studies(IAS),Wuhan University,Wuhan 430072,China [2]National Research Center for Carbohydrate Synthesis,Jiangxi Normal University,Nanchang 330022,China

出　　处：《Science China Chemistry》2023年第11期3178-3185,共8页中国科学（化学英文版）

基　　金：supported by the National Key R&D Program of China(2022YFA1505100,2021YFA1500100);the National Natural Science Foundation of China(22031008);the Fundamental Research Funds for the Central Universities(2042022rc0030,2042023kf0108,2042023kf1002);the Science Foundation of Wuhan(2020010601012192)。

摘　　要：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.

关 键 词：electrochemical organic synthesis DIHYDROPYRAN cascade cyclization selenylation TRIFLUOROMETHYLATION 

分 类 号：O626[理学—有机化学]