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Simple synthetic routes to N‐heterocyclic carbene gold(I)-aryl complexes : expanded scope and reactivity

Nikolaos Tzouras (UGent) , Marina Saab (UGent) , Wim Janssens, Thibault Cauwenbergh, Kristof Van Hecke (UGent) , Fady Nahra (UGent) and Steven Nolan (UGent)
(2020) CHEMISTRY-A EUROPEAN JOURNAL. 26(24). p.5541-5551
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Abstract
The discovery of sustainable and scalable synthetic protocols leading to gold-aryl compounds bearing N-heterocyclic carbene (NHC) ligands sparked an investigation of their reactivity and potential utility as organometallic synthons. The use of a mild base and green solvents provide access to these compounds, starting from widely available boronic acids and various [Au(NHC)Cl] complexes, with reactions taking place under air, at room temperature and leading to high yields with unprecedented ease. One compound, (N,N '-bis[2,6-(di-isopropyl)phenyl]imidazol-2-ylidene)(4-methoxyphenyl)gold, ([Au(IPr)(4-MeOC6H4)]), was synthesized on a multigram scale and used to gauge the reactivity of this class of compounds towards C-H/N-H bonds and with various acids, revealing simple pathways to gold-based species that possess attractive properties as materials, reagents and/or catalysts.
Keywords
General Chemistry, Catalysts, Gold Synthon, N-heterocyclic Carbenes, Sustainability, Synthetic Methodology, GOLD BOND FORMATION, STRUCTURAL-CHARACTERIZATION, ORGANOGOLD COMPOUNDS, COUPLING REACTIONS, TRANSMETALATION, PALLADIUM, ALKOXYLATION, COUNTERION, CATALYSIS, NHC

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Citation

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MLA
Tzouras, Nikolaos, et al. “Simple Synthetic Routes to N‐heterocyclic Carbene Gold(I)-Aryl Complexes : Expanded Scope and Reactivity.” CHEMISTRY-A EUROPEAN JOURNAL, vol. 26, no. 24, 2020, pp. 5541–51, doi:10.1002/chem.202000876.
APA
Tzouras, N., Saab, M., Janssens, W., Cauwenbergh, T., Van Hecke, K., Nahra, F., & Nolan, S. (2020). Simple synthetic routes to N‐heterocyclic carbene gold(I)-aryl complexes : expanded scope and reactivity. CHEMISTRY-A EUROPEAN JOURNAL, 26(24), 5541–5551. https://doi.org/10.1002/chem.202000876
Chicago author-date
Tzouras, Nikolaos, Marina Saab, Wim Janssens, Thibault Cauwenbergh, Kristof Van Hecke, Fady Nahra, and Steven Nolan. 2020. “Simple Synthetic Routes to N‐heterocyclic Carbene Gold(I)-Aryl Complexes : Expanded Scope and Reactivity.” CHEMISTRY-A EUROPEAN JOURNAL 26 (24): 5541–51. https://doi.org/10.1002/chem.202000876.
Chicago author-date (all authors)
Tzouras, Nikolaos, Marina Saab, Wim Janssens, Thibault Cauwenbergh, Kristof Van Hecke, Fady Nahra, and Steven Nolan. 2020. “Simple Synthetic Routes to N‐heterocyclic Carbene Gold(I)-Aryl Complexes : Expanded Scope and Reactivity.” CHEMISTRY-A EUROPEAN JOURNAL 26 (24): 5541–5551. doi:10.1002/chem.202000876.
Vancouver
1.
Tzouras N, Saab M, Janssens W, Cauwenbergh T, Van Hecke K, Nahra F, et al. Simple synthetic routes to N‐heterocyclic carbene gold(I)-aryl complexes : expanded scope and reactivity. CHEMISTRY-A EUROPEAN JOURNAL. 2020;26(24):5541–51.
IEEE
[1]
N. Tzouras et al., “Simple synthetic routes to N‐heterocyclic carbene gold(I)-aryl complexes : expanded scope and reactivity,” CHEMISTRY-A EUROPEAN JOURNAL, vol. 26, no. 24, pp. 5541–5551, 2020.
@article{8661463,
  abstract     = {{The discovery of sustainable and scalable synthetic protocols leading to gold-aryl compounds bearing N-heterocyclic carbene (NHC) ligands sparked an investigation of their reactivity and potential utility as organometallic synthons. The use of a mild base and green solvents provide access to these compounds, starting from widely available boronic acids and various [Au(NHC)Cl] complexes, with reactions taking place under air, at room temperature and leading to high yields with unprecedented ease. One compound, (N,N '-bis[2,6-(di-isopropyl)phenyl]imidazol-2-ylidene)(4-methoxyphenyl)gold, ([Au(IPr)(4-MeOC6H4)]), was synthesized on a multigram scale and used to gauge the reactivity of this class of compounds towards C-H/N-H bonds and with various acids, revealing simple pathways to gold-based species that possess attractive properties as materials, reagents and/or catalysts.}},
  author       = {{Tzouras, Nikolaos and Saab, Marina and Janssens, Wim and Cauwenbergh, Thibault and Van Hecke, Kristof and Nahra, Fady and Nolan, Steven}},
  issn         = {{0947-6539}},
  journal      = {{CHEMISTRY-A EUROPEAN JOURNAL}},
  keywords     = {{General Chemistry,Catalysts,Gold Synthon,N-heterocyclic Carbenes,Sustainability,Synthetic Methodology,GOLD BOND FORMATION,STRUCTURAL-CHARACTERIZATION,ORGANOGOLD COMPOUNDS,COUPLING REACTIONS,TRANSMETALATION,PALLADIUM,ALKOXYLATION,COUNTERION,CATALYSIS,NHC}},
  language     = {{eng}},
  number       = {{24}},
  pages        = {{5541--5551}},
  title        = {{Simple synthetic routes to N‐heterocyclic carbene gold(I)-aryl complexes : expanded scope and reactivity}},
  url          = {{http://dx.doi.org/10.1002/chem.202000876}},
  volume       = {{26}},
  year         = {{2020}},
}
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