4.6 Article

Mild and Soft Catalyzed Trifluoromethylthiolation of Boronic Acids: The Crucial Role of Water

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 42, Pages 14694-14698

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201502338

Keywords

boronic acid; cross-coupling; fluorine; trifluoromethanesulfenamide; trifluoromethylthiolation

Funding

  1. CNRS
  2. French Ministry of Research
  3. French Fluorine Network

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The most reactive 2nd generation of trifluoromethanesulfenamides undergoes a copper-catalyzed cross-coupling reaction with boronic acids to afford CF3S-molecules. Contrary to the previous methods in the literature, no base addition, no heating, and no large excess of reagents are required to obtain good results. Furthermore, a crucial role of a small amount of water to favor this reaction has been demonstrated. This constitutes the mildest described conditions for such a reaction.

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