4.5 Article

Copper-Mediated Di- and Monofluoromethanesulfonylation of Arenediazonium Tetrafluoroborates: Probing the Fluorine Effect

Journal

CHINESE JOURNAL OF CHEMISTRY
Volume 36, Issue 3, Pages 206-212

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.201700748

Keywords

difluoromethanesulfonylation; fluoromethanesulfonylation; arenediazonium; sodium sulfinate; fluorine effect

Funding

  1. National Key Research and Development Program of China [2015CB931900, 2016YFB0101200]
  2. National Natural Science Foundation of China [21632009, 21421002, 21472221, 21372246, 21302206]
  3. Key Programs of the Chinese Academy of Sciences [KGZD-EW-T08]
  4. Key Research Program of Frontier Sciences of CAS [QYZDJ-SSW-SLH049]
  5. Shanghai Science and Technology program [15XD1504400]
  6. Youth Innovation Promotion Association CAS [2014231]

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A copper-mediated di- and monofluoromethanesulfonylation of arenediazonium tetrafluoroborates using di- and monofluoromethanesulfinate reagents provides aryl difluoromethyl (or monofluoromethyl) sulfones in good yields. It was found that the relative reactivity of these sodium fluoroalkanesulfinates in the present reactions decreases in the following order: CH2FSO2Na > CF2HSO2Na > CF3SO2Na.

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