Carbosulfenylation of Alkenes with Organozinc Reagents and Dimethyl(methylthio)sulfonium Trifluoromethanesulfonate
Meizhong Tang, Shuxiong Han, Shenglan Huang, Shenlin Huang, Lan‐Gui Xie
Abstract
The electrophilic alkylthiolation of alkenes, initiated by dimethyl(methylthio)sulfonium salts and the subsequent addition of various heteronucleophilies has been well-established. Regarding the use of carbon nucleophiles, however, only carefully designed sp-type carbon sources have been successfully applied. We herein present our findings on the methylthiolation of alkenes with dimethyl(methylthio)sulfonium trifluoromethanesulfonate, followed by carbon-carbon bond formation in the presence of organozinc reagents, thus achieving a catalyst-free protocol toward to the carbosulfenylation of alkenes.
Topics & Concepts
SulfoniumChemistryTrifluoromethanesulfonateReagentNucleophileElectrophileTrimethylsilyl trifluoromethanesulfonateOrganic chemistryCatalysisCarbon fibersCombinatorial chemistryMedicinal chemistrySalt (chemistry)Composite materialMaterials scienceComposite numberSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsChemical Synthesis and Reactions