Synthesis of gold(I)-trifluoromethyl complexes and their role in generating spectroscopic evidence for a gold(I)-difluorocarbene species

Sofie M. P. Vanden Broeck; David J. Nelson; Alba Collado; Laura Falivene; Luigi Cavallo; David B. Cordes; Alexandra M. Z. Slawin; Kristof van Hecke; Fady Nahra; Catherine S. J. Cazin; Steven P. Nolan

doi:10.1002/chem.202100195

Synthesis of gold(I)-trifluoromethyl complexes and their role in generating spectroscopic evidence for a gold(I)-difluorocarbene species

Sofie M. P. Vanden Broeck, David J. Nelson, Alba Collado, Laura Falivene, Luigi Cavallo, David B. Cordes, Alexandra M. Z. Slawin, Kristof van Hecke, Fady Nahra, Catherine S. J. Cazin, Steven P. Nolan

Pure And Applied Chemistry

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Abstract

Readily prepared and bench-stable [Au(CF ₃)(NHC)] compounds were synthesized by using new methods, starting from [Au(OH)(NHC)], [Au(Cl)(NHC)] or [Au(L)(NHC)]HF ₂ 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(CF ₃)(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.

Original language	English
Pages (from-to)	8461-8467
Number of pages	7
Journal	Chemistry - A European Journal
Volume	27
Issue number	33
Early online date	6 Apr 2021
DOIs	https://doi.org/10.1002/chem.202100195
Publication status	Published - 10 Jun 2021

Keywords

difluorocarbene
trifluoromethyl
N-heterocyclic carbene
gold(I)
fluoride abstraction

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Vanden Broeck, S. M. P., Nelson, D. J., Collado, A., Falivene, L., Cavallo, L., Cordes, D. B., Slawin, A. M. Z., van Hecke, K., Nahra, F., Cazin, C. S. J., & Nolan, S. P. (2021). Synthesis of gold(I)-trifluoromethyl complexes and their role in generating spectroscopic evidence for a gold(I)-difluorocarbene species. Chemistry - A European Journal, 27(33), 8461-8467. https://doi.org/10.1002/chem.202100195

Vanden Broeck, Sofie M. P. ; Nelson, David J. ; Collado, Alba ; Falivene, Laura ; Cavallo, Luigi ; Cordes, David B. ; Slawin, Alexandra M. Z. ; van Hecke, Kristof ; Nahra, Fady ; Cazin, Catherine S. J. ; Nolan, Steven P. / Synthesis of gold(I)-trifluoromethyl complexes and their role in generating spectroscopic evidence for a gold(I)-difluorocarbene species. In: Chemistry - A European Journal. 2021 ; Vol. 27, No. 33. pp. 8461-8467.

@article{b588d2e0c30041f1b0c118274f927b2f,

title = "Synthesis of gold(I)-trifluoromethyl complexes and their role in generating spectroscopic evidence for a gold(I)-difluorocarbene species",

abstract = "Readily prepared and bench-stable [Au(CF 3)(NHC)] compounds were synthesized by using new methods, starting from [Au(OH)(NHC)], [Au(Cl)(NHC)] or [Au(L)(NHC)]HF 2 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(CF 3)(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. ",

keywords = "difluorocarbene, trifluoromethyl, N-heterocyclic carbene, gold(I), fluoride abstraction",

author = "{Vanden Broeck}, {Sofie M. P.} and Nelson, {David J.} and Alba Collado and Laura Falivene and Luigi Cavallo and Cordes, {David B.} and Slawin, {Alexandra M. Z.} and {van Hecke}, Kristof and Fady Nahra and Cazin, {Catherine S. J.} and Nolan, {Steven P.}",

year = "2021",

month = jun,

day = "10",

doi = "10.1002/chem.202100195",

language = "English",

volume = "27",

pages = "8461--8467",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

number = "33",

}

Vanden Broeck, SMP, Nelson, DJ, Collado, A, Falivene, L, Cavallo, L, Cordes, DB, Slawin, AMZ, van Hecke, K, Nahra, F, Cazin, CSJ & Nolan, SP 2021, 'Synthesis of gold(I)-trifluoromethyl complexes and their role in generating spectroscopic evidence for a gold(I)-difluorocarbene species', Chemistry - A European Journal, vol. 27, no. 33, pp. 8461-8467. https://doi.org/10.1002/chem.202100195

Synthesis of gold(I)-trifluoromethyl complexes and their role in generating spectroscopic evidence for a gold(I)-difluorocarbene species. / Vanden Broeck, Sofie M. P.; Nelson, David J.; Collado, Alba; Falivene, Laura; Cavallo, Luigi; Cordes, David B.; Slawin, Alexandra M. Z.; van Hecke, Kristof; Nahra, Fady; Cazin, Catherine S. J.; Nolan, Steven P.

In: Chemistry - A European Journal, Vol. 27, No. 33, 10.06.2021, p. 8461-8467.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Synthesis of gold(I)-trifluoromethyl complexes and their role in generating spectroscopic evidence for a gold(I)-difluorocarbene species

AU - Vanden Broeck, Sofie M. P.

AU - Nelson, David J.

AU - Collado, Alba

AU - Falivene, Laura

AU - Cavallo, Luigi

AU - Cordes, David B.

AU - Slawin, Alexandra M. Z.

AU - van Hecke, Kristof

AU - Nahra, Fady

AU - Cazin, Catherine S. J.

AU - Nolan, Steven P.

PY - 2021/6/10

Y1 - 2021/6/10

N2 - Readily prepared and bench-stable [Au(CF 3)(NHC)] compounds were synthesized by using new methods, starting from [Au(OH)(NHC)], [Au(Cl)(NHC)] or [Au(L)(NHC)]HF 2 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(CF 3)(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.

AB - Readily prepared and bench-stable [Au(CF 3)(NHC)] compounds were synthesized by using new methods, starting from [Au(OH)(NHC)], [Au(Cl)(NHC)] or [Au(L)(NHC)]HF 2 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(CF 3)(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.

KW - difluorocarbene

KW - trifluoromethyl

KW - N-heterocyclic carbene

KW - gold(I)

KW - fluoride abstraction

U2 - 10.1002/chem.202100195

DO - 10.1002/chem.202100195

M3 - Article

VL - 27

SP - 8461

EP - 8467

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 33

ER -

Synthesis of gold(I)-trifluoromethyl complexes and their role in generating spectroscopic evidence for a gold(I)-difluorocarbene species

Abstract

Keywords

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