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  Patrick 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 Patrick Nolan

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Abstract

Readily-prepared and bench-stable [Au(CF₃)(NHC)] compounds were synthesized using new methodologies, 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.

Original language	English
Journal	Chemistry - A European Journal
Volume	Early View
Early online date	14 May 2021
DOIs	https://doi.org/10.1002/chem.202100195
Publication status	E-pub ahead of print - 14 May 2021

Keywords

Difluorocarbene
Trifluoromethyl
N-heterocyclic carbene
Gold(I)
Fluoride abstraction

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10.1002/chem.202100195

Broeck_2021_CEJ_synthesis-gold_AAM
Copyright © 2021 Wiley‐VCH GmbH. This work has been made available online in accordance with publisher policies or with permission. Permission for further reuse of this content should be sought from the publisher or the rights holder. This is the author created accepted manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1002/chem.202100195
Accepted author manuscript, 1.36 MB

CCDC 2023143 - 2023147: Experimental Crystal Structure Determination
Broeck, S. M. P. V. (Contributor), Nelson, D. J. (Contributor), Collado, A. (Contributor), Falivene, L. (Contributor), Cavallo, L. (Contributor), Cordes, D. B. (Contributor), Slawin, A. M. Z. (Contributor), Van Hecke, K. (Contributor), Nahra, F. (Contributor), Cazin, C. S. J. (Contributor) & Nolan, S. P. (Contributor), The Cambridge Structural Database, 13 Aug 2020
DOI: 10.5517/ccdc.csd.cc25x7p1, https://dx.doi.org/10.5517/ccdc.csd.cc25x7q2 and 3 more links, https://dx.doi.org/10.5517/ccdc.csd.cc25x7r3, https://dx.doi.org/10.5517/ccdc.csd.cc25x7s4, https://dx.doi.org/10.5517/ccdc.csd.cc25x7t5 (show fewer)
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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, Early View. Advance online publication. https://doi.org/10.1002/chem.202100195

@article{ff1cc0a4f73549b882bf2a19efb02923,

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(CF3)(NHC)] compounds were synthesized using new methodologies, 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.",

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 Patrick}",

note = "We thank the Ghent University (IoF), the Special Research Fund (BOF) starting (SPN, CSJC) and advanced (SPN, KVH) grants and Research Foundation Flanders (FWO) (fellowship to SVB and grant to CSJC and KVH) for funding. ",

year = "2021",

month = may,

day = "14",

doi = "10.1002/chem.202100195",

language = "English",

volume = "Early View",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley & Sons, Ltd",

}

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. Early View. https://doi.org/10.1002/chem.202100195

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 Patrick

N1 - We thank the Ghent University (IoF), the Special Research Fund (BOF) starting (SPN, CSJC) and advanced (SPN, KVH) grants and Research Foundation Flanders (FWO) (fellowship to SVB and grant to CSJC and KVH) for funding.

PY - 2021/5/14

Y1 - 2021/5/14

N2 - Readily-prepared and bench-stable [Au(CF3)(NHC)] compounds were synthesized using new methodologies, 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.

AB - Readily-prepared and bench-stable [Au(CF3)(NHC)] compounds were synthesized using new methodologies, 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.

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

SN - 0947-6539

VL - Early View

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

ER -

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

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Keywords

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CCDC 2023143 - 2023147: Experimental Crystal Structure Determination

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