C−C Cross‐Couplings from a Cyclometalated Au(III) CN 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 in | Chemistry : a European journal Vol. 27; no. 57; pp. 14322 - 14334 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Wiley-VCH Verlag
13.10.2021
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| Subjects | |
| Online Access | Get full text |
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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(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). |
|---|---|
| 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). 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). |
| Author | Rigoulet, Mathilde Casini, Angela Pöthig, Alexander Barone, Giampaolo Bourissou, Didier Bonsignore, Riccardo Thomas, Sophie R. Jandl, Christian |
| Author_xml | – sequence: 1 givenname: Riccardo orcidid: 0000-0003-2699-4384 surname: Bonsignore fullname: Bonsignore, Riccardo organization: Chair of Medicinal and Bioinorganic Chemistry Department of Chemistry Technical University of Munich Lichtenbergstr. 4 85748 Garching b. München Germany – sequence: 2 givenname: Sophie R. orcidid: 0000-0003-1110-430X surname: Thomas fullname: Thomas, Sophie R. organization: Chair of Medicinal and Bioinorganic Chemistry Department of Chemistry Technical University of Munich Lichtenbergstr. 4 85748 Garching b. München Germany, School of Chemistry Cardiff University Main Building Park Place CF10 3AT Cardiff UK – sequence: 3 givenname: Mathilde surname: Rigoulet fullname: Rigoulet, Mathilde organization: CNRS/Université Paul Sabatier Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA, UMR 5069) 118 Route de Narbonne 31062 Toulouse Cedex 09 France – sequence: 4 givenname: Christian surname: Jandl fullname: Jandl, Christian organization: Catalysis Research Center & Department of Chemistry Technical University of Munich Ernst-Otto-Fischer Str. 1 85748 Garching b. München Germany – sequence: 5 givenname: Alexander surname: Pöthig fullname: Pöthig, Alexander organization: Catalysis Research Center & Department of Chemistry Technical University of Munich Ernst-Otto-Fischer Str. 1 85748 Garching b. München Germany – sequence: 6 givenname: Didier orcidid: 0000-0002-0249-1769 surname: Bourissou fullname: Bourissou, Didier organization: CNRS/Université Paul Sabatier Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA, UMR 5069) 118 Route de Narbonne 31062 Toulouse Cedex 09 France – sequence: 7 givenname: Giampaolo orcidid: 0000-0001-8773-2359 surname: Barone fullname: Barone, Giampaolo organization: Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche Università degli Studi di Palermo Viale delle Scienze, Edificio 17 90128 Palermo Italy – sequence: 8 givenname: Angela orcidid: 0000-0003-1599-9542 surname: Casini fullname: Casini, Angela organization: Chair of Medicinal and Bioinorganic Chemistry Department of Chemistry Technical University of Munich Lichtenbergstr. 4 85748 Garching b. München Germany |
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| CitedBy_id | crossref_primary_10_3390_inorganics11030100 crossref_primary_10_1002_chem_202202110 crossref_primary_10_1021_acs_inorgchem_2c04166 crossref_primary_10_1021_jacs_3c01974 crossref_primary_10_1002_chem_202304050 crossref_primary_10_1021_acs_inorgchem_3c02066 crossref_primary_10_1016_j_jorganchem_2023_122868 |
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| Title | C−C Cross‐Couplings from a Cyclometalated Au(III) CN Complex: Mechanistic Insights and Synthetic Developments |
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