- Author
- Andreas Simoens (UGent) , Thomas Scattolin (UGent) , Thibault Cauwenbergh, Nikolaos Tzouras, Gianmarco Pisanò (UGent) , Catherine Cazin (UGent) , Steven Nolan (UGent) and Christian Stevens (UGent)
- Organization
- Abstract
- N-Heterocyclic carbenes (NHCs) have proven themselves to be a popular and versatile ligand family for the synthesis of organometallic compounds. With interesting use cases in catalysis, medicinal chemistry and material sciences, the widespread use of this novel class of ligands has been a driving force for the development of a sustainable, efficient, and user-friendly route towards their synthesis. So far, the most commonly used synthetic strategy leading to NHC complexes, has involved the generation of free NHC by deprotonation of the corresponding azolium salt with a strong base (e.g.NaH, KOtBu) and subsequent coordination to a metal or chalcogen. However, this approach presents several drawbacks such as the need for strictly anhydrous conditions and incompatibility with the use of metal precursors which are sensitive to strong bases. Alternatively, the use of weak bases and mild conditions is currently the most sustainable and attractive synthetic approach for the preparation of Late-Transition Metal-NHC complexes. In our recent pieces of work, we have translated the latter method to a continuous flow system. This technology provides superior mass and heat transfer rates and allows for the use of small volumes of reagents and in turn enables easy and safe handling of hazardous reagents. Using this setup, complete conversion of cuprate, aurate or palladate species was achieved, yielding the targeted Cu(I), Au(I) and Pd(II)-NHC complexes in excellent yield, without the need for further purification. The scalability of the process was exemplified in the multigram-scale synthesis of [Cu(IPr)Cl]. Additionally, this simplistic reactor design also proved capable of synthesizing Sulfur‐ and Selenium‐NHC Compounds in similarly mild conditions, as well as the further arylation of the metal centre in a telescoped setup. All reactions examined proceed under extremely mild conditions and make use of technical grade acetone as solvent.
- Keywords
- Flow Chemistry, N-Heterocyclic carbenes
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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-01H6BTVR6EQYFJC9W398777MX8
- MLA
- Simoens, Andreas, et al. “NHC Complexes in Flow (NHC = N‐heterocyclic Carbene).” CRF-ChemCYS 2022, Abstracts, 2022.
- APA
- Simoens, A., Scattolin, T., Cauwenbergh, T., Tzouras, N., Pisanò, G., Cazin, C., … Stevens, C. (2022). NHC complexes in flow (NHC = N‐heterocyclic carbene). CRF-ChemCYS 2022, Abstracts. Presented at the Chemical Research in Flanders - Chemistry Conference for Young Scientists 2022 (CRF-ChemCYS 2022), Blankenberge, Belgium.
- Chicago author-date
- Simoens, Andreas, Thomas Scattolin, Thibault Cauwenbergh, Nikolaos Tzouras, Gianmarco Pisanò, Catherine Cazin, Steven Nolan, and Christian Stevens. 2022. “NHC Complexes in Flow (NHC = N‐heterocyclic Carbene).” In CRF-ChemCYS 2022, Abstracts.
- Chicago author-date (all authors)
- Simoens, Andreas, Thomas Scattolin, Thibault Cauwenbergh, Nikolaos Tzouras, Gianmarco Pisanò, Catherine Cazin, Steven Nolan, and Christian Stevens. 2022. “NHC Complexes in Flow (NHC = N‐heterocyclic Carbene).” In CRF-ChemCYS 2022, Abstracts.
- Vancouver
- 1.Simoens A, Scattolin T, Cauwenbergh T, Tzouras N, Pisanò G, Cazin C, et al. NHC complexes in flow (NHC = N‐heterocyclic carbene). In: CRF-ChemCYS 2022, Abstracts. 2022.
- IEEE
- [1]A. Simoens et al., “NHC complexes in flow (NHC = N‐heterocyclic carbene),” in CRF-ChemCYS 2022, Abstracts, Blankenberge, Belgium, 2022.
@inproceedings{01H6BTVR6EQYFJC9W398777MX8, abstract = {{N-Heterocyclic carbenes (NHCs) have proven themselves to be a popular and versatile ligand family for the synthesis of organometallic compounds. With interesting use cases in catalysis, medicinal chemistry and material sciences, the widespread use of this novel class of ligands has been a driving force for the development of a sustainable, efficient, and user-friendly route towards their synthesis. So far, the most commonly used synthetic strategy leading to NHC complexes, has involved the generation of free NHC by deprotonation of the corresponding azolium salt with a strong base (e.g.NaH, KOtBu) and subsequent coordination to a metal or chalcogen. However, this approach presents several drawbacks such as the need for strictly anhydrous conditions and incompatibility with the use of metal precursors which are sensitive to strong bases. Alternatively, the use of weak bases and mild conditions is currently the most sustainable and attractive synthetic approach for the preparation of Late-Transition Metal-NHC complexes. In our recent pieces of work, we have translated the latter method to a continuous flow system. This technology provides superior mass and heat transfer rates and allows for the use of small volumes of reagents and in turn enables easy and safe handling of hazardous reagents. Using this setup, complete conversion of cuprate, aurate or palladate species was achieved, yielding the targeted Cu(I), Au(I) and Pd(II)-NHC complexes in excellent yield, without the need for further purification. The scalability of the process was exemplified in the multigram-scale synthesis of [Cu(IPr)Cl]. Additionally, this simplistic reactor design also proved capable of synthesizing Sulfur‐ and Selenium‐NHC Compounds in similarly mild conditions, as well as the further arylation of the metal centre in a telescoped setup. All reactions examined proceed under extremely mild conditions and make use of technical grade acetone as solvent.}}, author = {{Simoens, Andreas and Scattolin, Thomas and Cauwenbergh, Thibault and Tzouras, Nikolaos and Pisanò, Gianmarco and Cazin, Catherine and Nolan, Steven and Stevens, Christian}}, booktitle = {{CRF-ChemCYS 2022, Abstracts}}, keywords = {{Flow Chemistry,N-Heterocyclic carbenes}}, language = {{eng}}, location = {{Blankenberge, Belgium}}, title = {{NHC complexes in flow (NHC = N‐heterocyclic carbene)}}, year = {{2022}}, }