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A Family of Thiazolium Salt Derived N‐Heterocyclic Carbenes (NHCs) for Organocatalysis: Synthesis, Investigation and Application in Cross‐Benzoin Condensation
Abstract
A family of thiazolium salt derived N‐heterocyclic carbenes (NHCs) bearing sterically demanding aryl substituents on the nitrogen and with varying backbone substitution patterns have been synthesized. Investigation of the catalytic activity of these NHCs in a number of benzoin‐type coupling reactions revealed markedly different levels of reactivity and selectivity. To elucidate the underlying factors leading to differences in reactivity, a study of the electronic and steric properties of these NHC catalysts was conducted. By using the best catalyst in this study, the intermolecular cross‐benzoin condensation reaction was explored in more detail.
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Cites
Pyruvate Ferredoxin Oxidoreductase and Its Radical Intermediate
Ragsdale, S. W. (2003) · Chemical Reviews · doi:10.1021/cr020423e · Cited by 259
Cited by
Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes
Flanigan, D. M., Romanov-Michailidis, F., White, N. A., & Rovis, T. (2015) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00060 · Cited by 2,045
N-Heterocyclic Carbene-Catalyzed Decarboxylative Alkylation of Aldehydes
Ishii, T., Kakeno, Y., Nagao, K., & Ohmiya, H. (2019) · Journal of the American Chemical Society · doi:10.1021/jacs.9b00880 · Cited by 336
Determining the Ligand Properties of N‐Heterocyclic Carbenes from 77Se NMR Parameters
Verlinden, K., Buhl, H., Frank, W., & Ganter, C. (2015) · European Journal of Inorganic Chemistry · doi:10.1002/ejic.201500174 · Cited by 270
Metadata
- Authors
- Piel, I., Pawelczyk, M. D., Hirano, K., Fröhlich, R., & Glorius, F.
- Venue
- European Journal of Organic Chemistry
- Publisher
- Wiley
- Published
- 2011-08-22
- Volume
- 2011
- Issue
- 28
- Pages
- 5475-5484
- ISSN
- 1099-0690 (ISSN-L)
- 1434-193X
- OpenAlex
- W2063677648
- Cited by
- 166
- References
- 1
- FWCI
- 6.28
- Type
- journal article
- Language
- en
- Open access
- closed
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- Piel, I., Pawelczyk, M. D., Hirano, K., Fröhlich, R., & Glorius, F. (2011). A Family of Thiazolium Salt Derived N‐Heterocyclic Carbenes (NHCs) for Organocatalysis: Synthesis, Investigation and Application in Cross‐Benzoin Condensation. European Journal of Organic Chemistry. https://doi.org/10.1002/ejoc.201100870
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