4.6 Article

Synthesis of Gold(I)-Trifluoromethyl Complexes and their Role in Generating Spectroscopic Evidence for a Gold(I)-Difluorocarbene Species

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 33, Pages 8461-8467

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202100195

Keywords

difluorocarbenes; fluoride abstraction; gold(I); N-heterocyclic carbenes; trifluoromethyl

Funding

  1. Ghent University (IoF)
  2. Special Research Fund (BOF)
  3. Research Foundation Flanders (FWO)

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Readily prepared and bench-stable [Au(CF3)(NHC)] compounds were synthesized using new methods, and the mechanism of their formation was investigated. A straightforward strategy for the selective cleavage of a single carbon/fluorine bond from [Au(CF3)(NHC)] complexes was attempted, leading to the unprecedented spectroscopic observation of a gold(I)-NHC difluorocarbene species.
Readily prepared and bench-stable [Au(CF3)(NHC)] compounds were synthesized by using new methods, starting from [Au(OH)(NHC)], [Au(Cl)(NHC)] or [Au(L)(NHC)]HF2 precursors (NHC=N-heterocyclic carbene). The mechanism of formation of these species was investigated. Consequently, a new and straightforward strategy for the mild and selective cleavage of a single carbon/fluorine bond from [Au(CF3)(NHC)] complexes was attempted and found to be reversible in the presence of an additional nucleophilic fluoride source. This straightforward technique has led to the unprecedented spectroscopic observation of a gold(I)-NHC difluorocarbene species.

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