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Updated: Jul 7, 2025

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Published on: July 28, 2018

An Organocopper(III) Fluoride Triggering C-CF₃ Bond Formation.

Daniel Joven-Sancho¹, Andrea Echeverri², Nathalie Saffon-Merceron³

¹Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA), Université Paul Sabatier, CNRS, 118 Route de Narbonne, 31062, Toulouse, France.

Angewandte Chemie (International Ed. in English)

|December 26, 2023

Summary

Stable copper(III) fluoride complexes were synthesized and characterized. These copper(III) intermediates enable the formation of carbon-trifluoromethyl bonds, yielding valuable trifluoromethylated alkynes for drug discovery and agrochemistry.

Keywords:

2e− Redox Sequences Fluorine High-Valent Copper Reaction Mechanisms Trifluoromethylation

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Published on: October 10, 2013

Area of Science:

Organometallic Chemistry
Fluorine Chemistry
Catalysis

Background:

Copper(III) intermediates are crucial for cross-coupling reactions but are typically unstable.
Stable copper(III) fluoride complexes are needed to explore their catalytic potential.

Purpose of the Study:

To synthesize and characterize the first stable copper(III) fluoride complex.
To investigate the utility of copper(III) fluoride in forging carbon-trifluoromethyl bonds.
To elucidate the mechanism of trifluoromethylation.

Main Methods:

Synthesis of copper(III) complexes via chloride addition and silver fluoride treatment.
Characterization using nuclear magnetic resonance (NMR) spectroscopy, single crystal X-ray diffraction (Sc-XRD), and elemental analysis (EA).
Mechanistic studies involving probes, theoretical calculations, intermediate trapping, and radical tests.

Main Results:

The first stable copper(III) fluoride, [PPh4][CuIII(CF3)3F] (2), was successfully synthesized.
Complex 2 effectively formed C-CF3 bonds using silyl-capped alkynes.
Mechanistic studies revealed the formation of copper(III) acetylides that undergo reductive elimination to yield trifluoromethylated alkynes.

Conclusions:

Stable copper(III) fluoride complexes can be synthesized and characterized.
These complexes are effective catalysts for synthesizing trifluoromethylated alkynes.
The mechanism involves copper(III) acetylide intermediates and reductive elimination, providing access to valuable synthons for drug discovery and agrochemistry.