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

Steven Patrick Nolan; 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

doi:10.1002/chem.202100195

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

Steven Patrick Nolan, 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

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

7 Scopus citations

Abstract

Readily-prepared and bench-stable [Au(CF 3 )(NHC)] compounds were synthesized using new methodologies, 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 (US)
Journal	Chemistry (Weinheim an der Bergstrasse, Germany)
DOIs	https://doi.org/10.1002/chem.202100195
State	Published - Apr 6 2021

Bibliographical note

KAUST Repository Item: Exported on 2021-04-10
Acknowledgements: 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. DFT calculations of the mechanism in this manuscript were performed using the Archie-WEST High Performance Computer at the University of Strathclyde.

ASJC Scopus subject areas

General Chemistry

Access to Document

10.1002/chem.202100195

https://repository.kaust.edu.sa/bitstream/10754/668599/1/Synthesis%20of_chem.202100195.pdf

Cite this

Nolan, S. P., 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. (2021). Synthesis of gold(I)-trifluoromethyl complexes and their role in generating spectroscopic evidence for a gold(I)-difluorocarbene species. Chemistry (Weinheim an der Bergstrasse, Germany). https://doi.org/10.1002/chem.202100195

@article{a5c79ab47ef940a7b7d8878b92c9e991,

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 using new methodologies, 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.",

author = "Nolan, {Steven Patrick} and {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}",

note = "KAUST Repository Item: Exported on 2021-04-10 Acknowledgements: 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. DFT calculations of the mechanism in this manuscript were performed using the Archie-WEST High Performance Computer at the University of Strathclyde.",

year = "2021",

month = apr,

day = "6",

doi = "10.1002/chem.202100195",

language = "English (US)",

journal = "Chemistry (Weinheim an der Bergstrasse, Germany)",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

}

Nolan, SP, Vanden Broeck, SMP, Nelson, DJ, Collado, A, Falivene, L, Cavallo, L, Cordes, DB, Slawin, AMZ, Van Hecke, K, Nahra, F & Cazin, CSJ 2021, 'Synthesis of gold(I)-trifluoromethyl complexes and their role in generating spectroscopic evidence for a gold(I)-difluorocarbene species.', Chemistry (Weinheim an der Bergstrasse, Germany). 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 - Nolan, Steven Patrick

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

N1 - KAUST Repository Item: Exported on 2021-04-10 Acknowledgements: 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. DFT calculations of the mechanism in this manuscript were performed using the Archie-WEST High Performance Computer at the University of Strathclyde.

PY - 2021/4/6

Y1 - 2021/4/6

N2 - Readily-prepared and bench-stable [Au(CF 3 )(NHC)] compounds were synthesized using new methodologies, 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 using new methodologies, 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.

UR - http://hdl.handle.net/10754/668599

UR - https://onlinelibrary.wiley.com/doi/10.1002/chem.202100195

U2 - 10.1002/chem.202100195

DO - 10.1002/chem.202100195

M3 - Article

C2 - 33822412

SN - 0947-6539

JO - Chemistry (Weinheim an der Bergstrasse, Germany)

JF - Chemistry (Weinheim an der Bergstrasse, Germany)

ER -

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

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

CCDC 2023146: Experimental Crystal Structure Determination : (1,3-bis[2,6-bis(propan-2-yl)phenyl]-4,5-dimethylimidazol-2-ylidene)-(trifluoromethyl)-gold

CCDC 2023145: Experimental Crystal Structure Determination : (1,3-bis[2,6-bis(diphenylmethyl)-4-methylphenyl]imidazol-2-ylidene)-(trifluoromethyl)-gold tetrahydrofuran solvate

CCDC 2023147: Experimental Crystal Structure Determination : (4,5-dichloro-1,3-bis[2,6-bis(propan-2-yl)phenyl]imidazol-2-ylidene)-(trifluoromethyl)-gold

Cite this

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

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 2023146: Experimental Crystal Structure Determination : (1,3-bis[2,6-bis(propan-2-yl)phenyl]-4,5-dimethylimidazol-2-ylidene)-(trifluoromethyl)-gold

CCDC 2023145: Experimental Crystal Structure Determination : (1,3-bis[2,6-bis(diphenylmethyl)-4-methylphenyl]imidazol-2-ylidene)-(trifluoromethyl)-gold tetrahydrofuran solvate

CCDC 2023147: Experimental Crystal Structure Determination : (4,5-dichloro-1,3-bis[2,6-bis(propan-2-yl)phenyl]imidazol-2-ylidene)-(trifluoromethyl)-gold

Cite this