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Stereospecific Dehydroxytrifluoromethylthiolation of Alcohols Promoted by a Combination of Hypervalent Trifluoromethylthio-iodine(III) Reagent and N-Heterocyclic Carbene

Xiao-Guang Yang, Jun-Jie Li, Feng-Huan Du, Yu-Xin Cheng and Chi Zhang*

*The Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China, Email:

X.-G. Yang, J.-J. Li, F.-H. Du, Y.-X. Cheng, C. Zhang, Org. Lett., 2023, 25, 2964-2969.

DOI: 10.1021/acs.orglett.3c00641


A N-heterocyclic carbene mediates a direct dehydroxytrifluoromethylthiolation of alcohols with a hypervalent iodine(III) reagent to provide CF3S-containing compounds. This method shows excellent stereospecificity and chemoselectivity to give a product with clean inversion of the stereochemical configuration.

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ID: J54-Y2023