4.8 Article

Arenesulfonyl Fluoride Synthesis via Copper-Catalyzed Fluorosulfonylation of Arenediazonium Salts

Journal

ORGANIC LETTERS
Volume 22, Issue 6, Pages 2281-2286

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c00484

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Funding

  1. National Natural Science Foundation of China [21421002, 21871283, 21737004, 21672239]
  2. Science and Technology Commission of Shanghai Municipality [17ZR1437000]
  3. Henan Province Science and Technology Open Cooperation Program [18210600017]

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We report herein a general and practical copper-catalyzed fluorosulfonylation reaction of a wide range of abundant arenediazonium salts to smoothly prepare various arenesulfonyl fluorides using the 1,4-diazabicyclo[2.2.2]octane-bis(sulfur dioxide) adduct as a convenient sulfonyl source in combination with KHF2 as an ideal fluorine source and without the need for additional oxidants. Interestingly, the electronic character of the arene ring in the starting arenediazonium salts has a significant impact on the reaction mechanistic pathway.

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