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Enantioselective N-Heterocyclic Carbene-Catalyzed β-Hydroxylation of Enals Using Nitroarenes: An Atom Transfer Reaction That Proceeds via Single Electron Transfer
Open accessAbstract
A novel oxidative N-heterocyclic carbene-catalyzed reaction pathway has been discovered. Alkyl and aryl enals undergo β-hydroxylation via oxygen atom transfer from electron-deficient nitrobenzenes, followed by trapping of the resultant acyl azolium by the solvent. The proposed mechanism involves a single electron transfer event to initiate the reaction followed by radical recombination. This represents a profound mechanistic departure from the established two-electron disconnects in NHC catalysis.
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Citations
Cites
Reduction potentials of one-electron couples involving free radicals in aqueous solution
Wardman, P. (1989) · Journal of Physical and Chemical Reference Data · doi:10.1063/1.555843 · Cited by 2,123
Cited by
Recent advances in N-heterocyclic carbene-based radical catalysis
Ishii, T., Nagao, K., & Ohmiya, H. (2020) · Chemical Science · doi:10.1039/d0sc01538e · Cited by 394
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
Liu, K., Schwenzer, M., & Studer, A. (2022) · ACS Catalysis · doi:10.1021/acscatal.2c03996 · Cited by 325
Metadata
- Authors
- White, N. A., & Rovis, T.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2014-10-10
- Volume
- 136
- Issue
- 42
- Pages
- 14674-14677
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2043304555
- Cited by
- 217
- References
- 1
- FWCI
- 7.08
- Type
- journal article
- Language
- en
- Open access
- hybrid
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- White, N. A., & Rovis, T. (2014). Enantioselective N-Heterocyclic Carbene-Catalyzed β-Hydroxylation of Enals Using Nitroarenes: An Atom Transfer Reaction That Proceeds via Single Electron Transfer. Journal of the American Chemical Society. https://doi.org/10.1021/ja5080739
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
