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Regio- and Stereoselective Synthesis of β-Methylthio Vinyl Triflates

Meizhong Tang, Yongjiao Wei, Shenlin Huang, Lan‐Gui Xie

2022Organic Letters21 citationsDOI

Abstract

Vinyl triflates are commonly employed as electrophilic vinyl sources in complex synthesis. The triflation of enolates is commonly required for the preparation of vinyl triflates, generally under strongly basic conditions. Herein, the reaction between alkynes and dimethyl(methylthio)sulfonium trifluoromethanesulfonate is presented, which leads to the development of a facile synthesis of β-methylthio vinyl triflates in a chemo-, regio-, and stereoselective manner under neutral and extremely simple conditions.

Topics & Concepts

SulfoniumChemistryStereoselectivityTrifluoromethanesulfonateElectrophileCombinatorial chemistryOrganic chemistryCatalysisSalt (chemistry)Sulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions
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