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Open Access Publications from the University of California

A catalytic fluoride-rebound mechanism for C(sp3)-CF3 bond formation.

  • Author(s): Levin, Mark D
  • Chen, Tiffany Q
  • Neubig, Megan E
  • Hong, Cynthia M
  • Theulier, Cyril A
  • Kobylianskii, Ilia J
  • Janabi, Mustafa
  • O'Neil, James P
  • Toste, F Dean
  • et al.

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)-CF3 reductive 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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