Direct electrophilic N-trifluoromethylation of azoles by a hypervalent iodine reagent

Angew Chem Int Ed Engl. 2012 Jun 25;51(26):6511-5. doi: 10.1002/anie.201201572. Epub 2012 May 22.


Effective CF(3) transfer: Various electron-rich nitrogen heterocycles (pyrazoles, triazoles, and tetrazoles) can be directly N-trifluoromethylated by a hypervalent iodine reagent in an efficient manner. The optimized procedure, which includes an in situ silylation of the substrate followed by an acid-catalyzed CF(3) transfer, provides ready access to a series of new and previously challenging or inaccessible NCF(3) compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azoles / chemistry*
  • Catalysis
  • Electrons*
  • Fluorine Compounds / chemistry*
  • Iodine / chemistry*
  • Methylation
  • Models, Molecular
  • Molecular Structure


  • Azoles
  • Fluorine Compounds
  • Iodine