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1,1,2,2-Tetrafluoro-2-(fluorosulfonyl)ethyl Benzoate: A Reagent for Fluorosulfonyl Tetrafluoroethoxylation
Shunli Chen1, Long Lu1, Qilong Shen1
1State Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. China.
Abstract:
A stable, scalable fluorosulfonyl tetrafluoroethoxylating reagent 1,1,2,2-tetrafluoro-2-(fluorosulfonyl)ethyl benzoate as a versatile surrogate of tetrafluoroethane β-sultone was developed. This reagent enables the concomitant introduction of a halogen (iodine, bromine, or chlorine) and a fluorosulfonyltetrafluoroethoxy group across the double bond of alkenes, a transformation termed halofluorosulfonyl tetrafluoroethoxylation. Subsequent elimination of the brominated adducts provides efficient access to bifunctional styrenyl fluorosulfonyl tetrafluoroethyl ethers, which are promising monomers for perfluorosulfonic acid (PFSA) ionomers. Its utility is further demonstrated in diverse transformations, including nucleophilic substitutions, alkyne additions, and esterifications, as well as preparation of photoacid generators (PAGs), establishing it as a robust and multifaceted building block for organofluorine chemistry.
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