C−C Cross‐Couplings from a Cyclometalated Au(III) C∧ N Complex: Mechanistic Insights and Synthetic Developments

In recent years, the reactivity of gold complexes was shown to extend well beyond π‐activation and to hold promises to achieve selective cross‐couplings in several C−C and C−E (E=heteroatom) bond forming reactions. Here, with the aim of exploiting new organometallic species for cross‐coupling reacti...

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Published inChemistry : a European journal Vol. 27; no. 57; pp. 14322 - 14334
Main Authors Bonsignore, Riccardo, Thomas, Sophie R., Rigoulet, Mathilde, Jandl, Christian, Pöthig, Alexander, Bourissou, Didier, Barone, Giampaolo, Casini, Angela
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 13.10.2021
Wiley Subscription Services, Inc
John Wiley and Sons Inc
Subjects
Benzylpyridines
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Coordination
Couplings
Cross coupling
Crystallography
Gold
gold cyclometalated complexes
Intermediates
Magnetic resonance spectroscopy
NMR
NMR spectroscopy
Nuclear magnetic resonance
Nucleophiles
organometallics
Physical Sciences
Reagents
reductive elimination
Science & Technology
Tin
Two dimensional analysis
GOLD(III) COMPLEXES
ORGANIC-SYNTHESIS
PHOTOREDOX
REACTIVITY
BOND FORMATION
OXIDATIVE ADDITION
gold cyclometalated complexes
H ACTIVATION
organometallics
cross-coupling
BASIS-SETS
reductive elimination
NMR spectroscopy
DUAL GOLD
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Abstract In recent years, the reactivity of gold complexes was shown to extend well beyond π‐activation and to hold promises to achieve selective cross‐couplings in several C−C and C−E (E=heteroatom) bond forming reactions. Here, with the aim of exploiting new organometallic species for cross‐coupling reactions, we report on the Au(III)‐mediated C(sp2)−C(sp) occurring upon reaction of the cyclometalated complex [Au(CCH2N)Cl2] (1, CCH2N=2‐benzylpyridine) with AgPhCC. The reaction progress has been monitored by NMR spectroscopy, demonstrating the involvement of a number of key intermediates, whose structures have been unambiguously ascertained through 1D and 2D NMR analyses (1H, 13C, 1H‐1H COSY, 1H‐13C HSQC and 1H‐13C HMBC) as well as by HR‐ESI‐MS and X‐ray diffraction studies. Furthermore, crystallographic studies have serendipitously resulted in the authentication of zwitterionic Au(I) complexes as side‐products arising from cyclization of the coupling product in the coordination sphere of gold. The experimental work has been paralleled and complemented by DFT calculations of the reaction profiles, providing valuable insight into the structure and energetics of the key intermediates and transition states, as well as on the coordination sphere of gold along the whole process. Of note, the broader scope of the cross‐coupling at the Au(III) CCH2N centre has also been demonstrated studying the reaction of 1 with C(sp2)‐based nucleophiles, namely vinyl and heteroaryl tin and zinc reagents. These reactions stand as rare examples of C(sp2)−C(sp2) cross‐couplings at Au(III). The mechanism of C(sp2)−C(sp) coupling templated by the Au(III) cyclometalated complex [Au(CCH2N)Cl2] has been investigated. By tuning the reaction conditions and monitoring its progress by NMR, a number of intermediate species involved in the reductive elimination process could be isolated and characterised by different spectroscopic and analytical methods, including XRD, as well as by DFT studies.
AbstractList In recent years, the reactivity of gold complexes was shown to extend well beyond π‐activation and to hold promises to achieve selective cross‐couplings in several C−C and C−E (E=heteroatom) bond forming reactions. Here, with the aim of exploiting new organometallic species for cross‐coupling reactions, we report on the Au(III)‐mediated C(sp 2 )−C(sp) occurring upon reaction of the cyclometalated complex [Au(C CH2 N)Cl 2 ] ( 1 , C CH2 N=2‐benzylpyridine) with AgPhCC. The reaction progress has been monitored by NMR spectroscopy, demonstrating the involvement of a number of key intermediates, whose structures have been unambiguously ascertained through 1D and 2D NMR analyses ( 1 H, 13 C, 1 H‐ 1 H COSY, 1 H‐ 13 C HSQC and 1 H‐ 13 C HMBC) as well as by HR‐ESI‐MS and X‐ray diffraction studies. Furthermore, crystallographic studies have serendipitously resulted in the authentication of zwitterionic Au(I) complexes as side‐products arising from cyclization of the coupling product in the coordination sphere of gold. The experimental work has been paralleled and complemented by DFT calculations of the reaction profiles, providing valuable insight into the structure and energetics of the key intermediates and transition states, as well as on the coordination sphere of gold along the whole process. Of note, the broader scope of the cross‐coupling at the Au(III) C CH2 N centre has also been demonstrated studying the reaction of 1 with C(sp 2 )‐based nucleophiles, namely vinyl and heteroaryl tin and zinc reagents. These reactions stand as rare examples of C(sp 2 )−C(sp 2 ) cross‐couplings at Au(III). The mechanism of C(sp 2 )−C(sp) coupling templated by the Au(III) cyclometalated complex [Au(C CH2 N)Cl 2 ] has been investigated. By tuning the reaction conditions and monitoring its progress by NMR, a number of intermediate species involved in the reductive elimination process could be isolated and characterised by different spectroscopic and analytical methods, including XRD, as well as by DFT studies.
In recent years, the reactivity of gold complexes was shown to extend well beyond π‐activation and to hold promises to achieve selective cross‐couplings in several C−C and C−E (E=heteroatom) bond forming reactions. Here, with the aim of exploiting new organometallic species for cross‐coupling reactions, we report on the Au(III)‐mediated C(sp2)−C(sp) occurring upon reaction of the cyclometalated complex [Au(CCH2N)Cl2] (1, CCH2N=2‐benzylpyridine) with AgPhCC. The reaction progress has been monitored by NMR spectroscopy, demonstrating the involvement of a number of key intermediates, whose structures have been unambiguously ascertained through 1D and 2D NMR analyses (1H, 13C, 1H‐1H COSY, 1H‐13C HSQC and 1H‐13C HMBC) as well as by HR‐ESI‐MS and X‐ray diffraction studies. Furthermore, crystallographic studies have serendipitously resulted in the authentication of zwitterionic Au(I) complexes as side‐products arising from cyclization of the coupling product in the coordination sphere of gold. The experimental work has been paralleled and complemented by DFT calculations of the reaction profiles, providing valuable insight into the structure and energetics of the key intermediates and transition states, as well as on the coordination sphere of gold along the whole process. Of note, the broader scope of the cross‐coupling at the Au(III) CCH2N centre has also been demonstrated studying the reaction of 1 with C(sp2)‐based nucleophiles, namely vinyl and heteroaryl tin and zinc reagents. These reactions stand as rare examples of C(sp2)−C(sp2) cross‐couplings at Au(III). The mechanism of C(sp2)−C(sp) coupling templated by the Au(III) cyclometalated complex [Au(CCH2N)Cl2] has been investigated. By tuning the reaction conditions and monitoring its progress by NMR, a number of intermediate species involved in the reductive elimination process could be isolated and characterised by different spectroscopic and analytical methods, including XRD, as well as by DFT studies.
In recent years, the reactivity of gold complexes was shown to extend well beyond π‐activation and to hold promises to achieve selective cross‐couplings in several C−C and C−E (E=heteroatom) bond forming reactions. Here, with the aim of exploiting new organometallic species for cross‐coupling reactions, we report on the Au(III)‐mediated C(sp2)−C(sp) occurring upon reaction of the cyclometalated complex [Au(CCH2N)Cl2] (1, CCH2N=2‐benzylpyridine) with AgPhCC. The reaction progress has been monitored by NMR spectroscopy, demonstrating the involvement of a number of key intermediates, whose structures have been unambiguously ascertained through 1D and 2D NMR analyses (1H, 13C, 1H‐1H COSY, 1H‐13C HSQC and 1H‐13C HMBC) as well as by HR‐ESI‐MS and X‐ray diffraction studies. Furthermore, crystallographic studies have serendipitously resulted in the authentication of zwitterionic Au(I) complexes as side‐products arising from cyclization of the coupling product in the coordination sphere of gold. The experimental work has been paralleled and complemented by DFT calculations of the reaction profiles, providing valuable insight into the structure and energetics of the key intermediates and transition states, as well as on the coordination sphere of gold along the whole process. Of note, the broader scope of the cross‐coupling at the Au(III) CCH2N centre has also been demonstrated studying the reaction of 1 with C(sp2)‐based nucleophiles, namely vinyl and heteroaryl tin and zinc reagents. These reactions stand as rare examples of C(sp2)−C(sp2) cross‐couplings at Au(III).
In recent years, the reactivity of gold complexes was shown to extend well beyond pi-activation and to hold promises to achieve selective cross-couplings in several C-C and C-E (E=heteroatom) bond forming reactions. Here, with the aim of exploiting new organometallic species for cross-coupling reactions, we report on the Au(III)-mediated C(sp(2))-C(sp) occurring upon reaction of the cyclometalated complex [Au((CN)-N-CH2)Cl-2] (1, (CN)-N-CH2=2-benzylpyridine) with AgPhCC. The reaction progress has been monitored by NMR spectroscopy, demonstrating the involvement of a number of key intermediates, whose structures have been unambiguously ascertained through 1D and 2D NMR analyses (H-1, C-13, H-1-H-1 COSY, H-1-C-13 HSQC and H-1-C-13 HMBC) as well as by HR-ESI-MS and X-ray diffraction studies. Furthermore, crystallographic studies have serendipitously resulted in the authentication of zwitterionic Au(I) complexes as side-products arising from cyclization of the coupling product in the coordination sphere of gold. The experimental work has been paralleled and complemented by DFT calculations of the reaction profiles, providing valuable insight into the structure and energetics of the key intermediates and transition states, as well as on the coordination sphere of gold along the whole process. Of note, the broader scope of the cross-coupling at the Au(III) (CN)-N-CH2 centre has also been demonstrated studying the reaction of 1 with C(sp(2))-based nucleophiles, namely vinyl and heteroaryl tin and zinc reagents. These reactions stand as rare examples of C(sp(2))-C(sp(2)) cross-couplings at Au(III).
In recent years, the reactivity of gold complexes was shown to extend well beyond π-activation and to hold promises to achieve selective cross-couplings in several C-C and C-E (E=heteroatom) bond forming reactions. Here, with the aim of exploiting new organometallic species for cross-coupling reactions, we report on the Au(III)-mediated C(sp2 )-C(sp) occurring upon reaction of the cyclometalated complex [Au(CCH2 N)Cl2 ] (1, CCH2 N=2-benzylpyridine) with AgPhCC. The reaction progress has been monitored by NMR spectroscopy, demonstrating the involvement of a number of key intermediates, whose structures have been unambiguously ascertained through 1D and 2D NMR analyses (1 H, 13 C, 1 H-1 H COSY, 1 H-13 C HSQC and 1 H-13 C HMBC) as well as by HR-ESI-MS and X-ray diffraction studies. Furthermore, crystallographic studies have serendipitously resulted in the authentication of zwitterionic Au(I) complexes as side-products arising from cyclization of the coupling product in the coordination sphere of gold. The experimental work has been paralleled and complemented by DFT calculations of the reaction profiles, providing valuable insight into the structure and energetics of the key intermediates and transition states, as well as on the coordination sphere of gold along the whole process. Of note, the broader scope of the cross-coupling at the Au(III) CCH2 N centre has also been demonstrated studying the reaction of 1 with C(sp2 )-based nucleophiles, namely vinyl and heteroaryl tin and zinc reagents. These reactions stand as rare examples of C(sp2 )-C(sp2 ) cross-couplings at Au(III).
Author Rigoulet, Mathilde
Casini, Angela
Pöthig, Alexander
Barone, Giampaolo
Bourissou, Didier
Bonsignore, Riccardo
Thomas, Sophie R.
Jandl, Christian
AuthorAffiliation 2 School of Chemistry Cardiff University Main Building Park Place CF10 3AT Cardiff UK
4 Catalysis Research Center & Department of Chemistry Technical University of Munich Ernst-Otto-Fischer Str. 1 85748 Garching b. München Germany
5 Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche Università degli Studi di Palermo Viale delle Scienze, Edificio 17 90128 Palermo Italy
1 Chair of Medicinal and Bioinorganic Chemistry Department of Chemistry Technical University of Munich Lichtenbergstr. 4 85748 Garching b. München Germany
3 CNRS/Université Paul Sabatier Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA, UMR 5069) 118 Route de Narbonne 31062 Toulouse Cedex 09 France
AuthorAffiliation_xml – name: 5 Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche Università degli Studi di Palermo Viale delle Scienze, Edificio 17 90128 Palermo Italy
– name: 2 School of Chemistry Cardiff University Main Building Park Place CF10 3AT Cardiff UK
– name: 3 CNRS/Université Paul Sabatier Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA, UMR 5069) 118 Route de Narbonne 31062 Toulouse Cedex 09 France
– name: 1 Chair of Medicinal and Bioinorganic Chemistry Department of Chemistry Technical University of Munich Lichtenbergstr. 4 85748 Garching b. München Germany
– name: 4 Catalysis Research Center & Department of Chemistry Technical University of Munich Ernst-Otto-Fischer Str. 1 85748 Garching b. München Germany
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Issue 57
Keywords GOLD(III) COMPLEXES
ORGANIC-SYNTHESIS
PHOTOREDOX
REACTIVITY
BOND FORMATION
OXIDATIVE ADDITION
gold cyclometalated complexes
H ACTIVATION
organometallics
cross-coupling
BASIS-SETS
reductive elimination
NMR spectroscopy
DUAL GOLD
Language English
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This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
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Notes These authors contributed equally to this manuscript.
Agence Nationale de la Recherche (ANR)
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PublicationDecade 2020
PublicationPlace WEINHEIM
PublicationPlace_xml – name: WEINHEIM
– name: Weinheim
– name: Hoboken
PublicationSubtitle A European Journal
PublicationTitle Chemistry : a European journal
PublicationTitleAbbrev CHEM-EUR J
PublicationYear 2021
Publisher Wiley
Wiley Subscription Services, Inc
John Wiley and Sons Inc
Publisher_xml – name: Wiley
– name: Wiley Subscription Services, Inc
– name: John Wiley and Sons Inc
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Snippet In recent years, the reactivity of gold complexes was shown to extend well beyond π‐activation and to hold promises to achieve selective cross‐couplings in...
In recent years, the reactivity of gold complexes was shown to extend well beyond pi-activation and to hold promises to achieve selective cross-couplings in...
In recent years, the reactivity of gold complexes was shown to extend well beyond π-activation and to hold promises to achieve selective cross-couplings in...
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StartPage 14322
SubjectTerms Benzylpyridines
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Coordination
Couplings
Cross coupling
Crystallography
Gold
gold cyclometalated complexes
Intermediates
Magnetic resonance spectroscopy
NMR
NMR spectroscopy
Nuclear magnetic resonance
Nucleophiles
organometallics
Physical Sciences
Reagents
reductive elimination
Science & Technology
Tin
Two dimensional analysis
Title C−C Cross‐Couplings from a Cyclometalated Au(III) C∧ N Complex: Mechanistic Insights and Synthetic Developments
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fchem.202102668
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https://www.proquest.com/docview/2581195468
https://search.proquest.com/docview/2555637302
https://pubmed.ncbi.nlm.nih.gov/PMC8597034
Volume 27
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