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A catalytic fluoride-rebound mechanism for C(sp3)-CF3bond formation

  • Author(s): Levin, MD
  • Chen, TQ
  • Neubig, ME
  • Hong, CM
  • Theulier, CA
  • Kobylianskii, IJ
  • Janabi, M
  • O'Neil, JP
  • Toste, FD
  • et al.
Abstract

© The Authors, some rights reserved. The biological properties of trifluoromethyl compounds have led to their ubiquity in pharmaceuticals, yet their chemical properties have made their preparation a substantial challenge, necessitating innovative chemical solutions. We report the serendipitous discovery of a borane-catalyzed formal C(sp3)-CF3reductive elimination from Au(III) that accesses these compounds by a distinct mechanism proceeding via fluoride abstraction, migratory insertion, and C-F reductive elimination to achieve a net C-C bond construction. The parent bis(trifluoromethyl)Au(III) complexes tolerate a surprising breadth of synthetic protocols, enabling the synthesis of complex organic derivatives without cleavage of the Au-C bond. This feature, combined with the "fluoride-rebound" mechanism, was translated into a protocol for the synthesis of 18F-radiolabeled aliphatic CF3-containing compounds, enabling the preparation of potential tracers for use in positron emission tomography.

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