Highly Regioselective Dichalcogenation of Alkenyl Sulfonium Salts to Access 1,1-Dichalcogenalkenes

作者：Jie Zhu, Yun Ye, Yifei Yan, Jinghui Sun, Yinhua Huang · 发表于：Organic Letters · 年份：2023 · DOI：10.1021/acs.orglett.3c01886 · 被引用次数：39 · 研究领域：Sulfur-Based Synthesis Techniques、Fluorine in Organic Chemistry、Synthesis and Catalytic Reactions

An unprecedented geminal olefinic dichalcogenation of alkenyl sulfonium salts with dichalcogenides ArYYAr (Y = S, Se, Te) is reported, providing various trisubstituted 1,1-dichalcogenalkenes [Ar 1 CH = C(YAr 2 ) 2 ] in a highly selective manner under mild and catalyst-free conditions. The key process involves the formation of two geminal olefinic C–Y bonds via sequential C–Y cross-coupling and C–H chalcogenation. A mechanistic rationale is further supported by control experiments and density functional theory calculations.