Highly Regioselective Dichalcogenation of Alkenyl Sulfonium Salts to Access 1,1-Dichalcogenalkenes
Jie Zhu, Yun Ye, Yifei Yan, Jinghui Sun, Yinhua Huang
Abstract
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.
Topics & Concepts
SulfoniumRegioselectivityChemistryCombinatorial chemistryMedicinal chemistryStereochemistryOrganic chemistrySalt (chemistry)CatalysisSulfur-Based Synthesis TechniquesFluorine in Organic ChemistrySynthesis and Catalytic Reactions