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Published on: July 28, 2018

Active trifluoromethylating agents from well-defined Copper(I)-CF3 complexes.

Galyna G Dubinina1, Hideki Furutachi, David A Vicic

  • 1Department of Chemistry, University of Hawaii, 2545 McCarthy Mall, Honolulu, Hawaii 96822, USA.

Journal of the American Chemical Society
|June 12, 2008
PubMed
Summary

Researchers report the first isolable copper(I) trifluoromethyl (CF3) complexes. These novel N-heterocyclic carbene-supported copper complexes efficiently transfer CF3 groups to organic halides.

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Area of Science:

  • Organometallic Chemistry
  • Fluorine Chemistry
  • Catalysis

Background:

  • Copper complexes are versatile catalysts.
  • Trifluoromethyl (CF3) groups are important in pharmaceuticals and materials.
  • Isolable Cu(I)-CF3 complexes are challenging to synthesize.

Purpose of the Study:

  • To synthesize and characterize novel isolable copper(I) trifluoromethyl (CF3) complexes.
  • To investigate the structural characteristics of these complexes.
  • To evaluate their utility in trifluoromethylation reactions.

Main Methods:

  • Reaction of N-heterocyclic carbene (NHC)-supported copper tert-butoxide complexes with Me3Si-CF3.
  • Structural characterization using X-ray crystallography.
  • In situ generation of copper trifluoromethyl complexes for transfer reactions.

Main Results:

  • First examples of isolable and structurally characterized Cu(I)-CF3 complexes are reported.
  • Complex structures depend on the saturation of the NHC ring.
  • In situ generated (SIiPr)Cu-CF3 efficiently transferred the CF3 group to organic halides under mild conditions.

Conclusions:

  • Novel NHC-supported Cu(I)-CF3 complexes have been synthesized and characterized.
  • These complexes offer a new platform for trifluoromethylation chemistry.
  • The developed methodology provides a mild and efficient route for introducing CF3 groups into organic molecules.