Stereospecific Dehydroxytrifluoromethylthiolation of Alcohols Promoted by a Combination of Hypervalent Trifluoromethylthio-iodine(III) Reagent and N-Heterocyclic Carbene
Xiaoguang Yang, Junjie Li, Feng‐Huan Du, Yu-Xin Cheng, Chi Zhang
Abstract
S-containing compounds. Herein, we report a method for dehydroxytrifluoromethylthiolation of alcohols by using the combination of hypervalent iodine(III) reagent TFTI and N-heterocyclic carbenes. This method shows excellent stereospecificity and chemoselectivity to give a product with clean inversion of the configuration of hydroxyl groups as well as can be used for late-stage modification of structurally complex alcohols. The reaction mechanism is proposed with experimental and computational evidence.
Topics & Concepts
Hypervalent moleculeChemistryReagentStereospecificityIodineChemoselectivityCarbeneCombinatorial chemistryOrganic chemistryCatalysisFluorine in Organic ChemistrySulfur-Based Synthesis TechniquesInorganic Fluorides and Related Compounds