4.7 Article

Electrochemical Minisci-type trifluoromethylation of electron-deficient heterocycles mediated by bromide ions

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 6, Issue 14, Pages 2392-2397

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c9qo00552h

Keywords

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Funding

  1. National Key Technology RD Program [2017YFB0307502]
  2. National Natural Science Foundation of China [21871019]

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An electrochemical methodology for the Minisci-type trifluoromethylation of electron-deficient heterocycles mediated by cheap and easily available bromide ions has been developed. By virtue of the in situ generated sulfonyl hypobromite intermediate, the CF3 radical can be regulated and controlled at a low concentration, thereby improving the reaction efficiency over direct electrolysis. Also, this indirect electrochemical process is performed in a beaker-type undivided cell under galvanostatic conditions, without using external expensive supporting electrolytes. This protocol provides an alternative electrochemical trifluoromethylation methodology for the late-stage functionalization of biologically important molecules.

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