4.5 Article

Arenesulfonyl Fluoride Synthesis via Copper-free Sandmeyer-type Fluorosulfonylation of Arenediazonium Salts

Journal

CHINESE JOURNAL OF CHEMISTRY
Volume 38, Issue 10, Pages 1107-1110

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.202000175

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Funding

  1. National Natural Science Foundation of China [21421002, 201871283, 21737004, 21672239]
  2. Science and Technology Commission of Shanghai Municipality [17ZR1437000]
  3. Foundation of Science and Technology on Sanming Institute of Fluorochemical Industry [FCIT201701BR]

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The limited availability of highly valuable arenesulfonyl fluorides seriously hinders their further application in many research fields including medicinal chemistry and chemical biological, organic synthesis, polymer preparation, etc. We report herein a mild and efficient copper-free Sandmeyer-type fluorosulfonylation reaction of various arenediazonium salts to prepare valuable arenesulfonyl fluorides using K2S2O5 as both a reductant and a practical sulfonyl source in combination with N-fluorobenzenesulfonimide as an effective fluorine source. This methodology provides an attractive route to diverse important arenesulfonyl fluorides given the overall practicality and scope.

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