4.3 Article

Arenesulfonyl fluoride synthesis via one-pot copper-free Sandmeyer-type three-component reaction of aryl amine, K2S2O5, and NFSI

Journal

JOURNAL OF FLUORINE CHEMISTRY
Volume 254, Issue -, Pages -

Publisher

ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2022.109948

Keywords

Fluorosulfonylation; Arylamine; Sulfur dioxide insertion fluorination; Copper-free; Radical

Funding

  1. National Natural Science Foundation of China [21871283]
  2. project of Science and Technology Commission of Shanghai Munici-pality in China [21010503800]
  3. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
  4. Shanghai Engineering Research Center of Green Fluo-ropharmaceutical Technology
  5. Science Research Foundation of Shanghai Institute of Technology

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A one-pot procedure for the direct introduction of sulfonyl fluoride groups into arenes from arylamines is developed using K2S2O5 and NFSI as the sulfur dioxide surrogate and fluorine source. It features mild and practical conditions and good functional group tolerance.
A one-pot procedure for the synthesis of arenesulfonyl fluorides from arylamine is developed with K2S2O5 and Nfluorobenzenesulfonimide (NFSI) as the sulfur dioxide surrogate and fluorine source, respectively. This method realizes the direct introduction of sulfonyl fluoride groups into arenes from abundant arylamines under transition-metal-free catalysis conditions, and features its mild and practical conditions and good functional group tolerance.

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