Sulfonium Salt-Mediated Bisthiolation of Terminal Alkynes to Access Symmetrical and Nonsymmetrical <i>Z-</i> 1,2 <i>-</i> Dithioalkenes
Sha Peng, Xiang-Qin Xu, Ding Luo, Limei Duan, Li‐Hua Yang, Long‐Yong Xie
Abstract
In this study, we report an efficient one-pot bisthiolation reaction of terminal alkynes, which enables the regio- and stereoselective synthesis of diverse symmetrical and nonsymmetrical ( Z )-1,2-dithioalkenes with wide substrate scope and excellent functional group compatibility. Mechanistic investigations reveal that the reaction is initiated by in situ-generated alkynyl sulfonium salts, formed from terminal alkynes, sulfoxides, and triflic anhydride (Tf 2 O). Gram-scale synthesis and late-stage functionalization further underscore the application of this method in organic synthesis.
Topics & Concepts
SulfoniumChemistryTerminal (telecommunication)StereoselectivitySubstrate (aquarium)Combinatorial chemistrySurface modificationChemoselectivityFunctional groupStereochemistryScope (computer science)Reaction conditionsHalideGroup (periodic table)Polymer chemistryDensity functional theoryElectrophileAlkyneMoleculeReagentStereoisomerismCatalysisSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsSynthesis of heterocyclic compounds