Deoxygenation of ClSOCFCOOMe with Triphenylphosphine for the Metal-Free Direct Electrophilic Difluoroalkylthiolation of Various Heterocycles.

J Org Chem

Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

Published: June 2023

A direct electrophilic difluoroalkylthiolation reaction of indole derivatives and other electron-rich heterocycles using methyl 2,2-difluoro-2-(chlorsulfonyl)acetate (ClSOCFCOOMe) derived from Chen's reagent (FSOCFCOOMe) is described. The ester group in the product can be further utilized in subsequent versatile transformations. The reactions provide good yields of the corresponding difluoroalkylthiolation products and exhibit high functional group compatibility. It is expected to serve as an alternative and practical protocol for difluoroalkylthiolation of various heterocycles.

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http://dx.doi.org/10.1021/acs.joc.3c00342DOI Listing

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