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Biomimetic Carbene‐Catalyzed Oxidations of Aldehydes Using TEMPO
Abstract
Transition-metal-free organocatalytic oxidations of various aldehydes proceed with the TEMPO radical as a mild organic oxidant; the resulting TEMPO esters are formed in moderate to excellent yields (see scheme). N-Heterocyclic carbenes (NHCs) are efficient catalysts and activate aldehydes for electron-transfer reactions. The TEMPO esters are readily hydrolyzed and the nitroxide can be regenerated by aerobic oxidation.
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Citations
Cites
Pyruvate Ferredoxin Oxidoreductase and Its Radical Intermediate
Ragsdale, S. W. (2003) · Chemical Reviews · doi:10.1021/cr020423e · Cited by 259
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
Metadata
- Authors
- Guin, J., De Sarkar, S., Grimme, S., & Studer, A.
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2008-10-21
- Volume
- 47
- Issue
- 45
- Pages
- 8727-8730
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2083357654
- Cited by
- 421
- References
- 1
- FWCI
- 8.75
- Type
- journal article
- Language
- en
- Open access
- closed
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- Guin, J., De Sarkar, S., Grimme, S., & Studer, A. (2008). Biomimetic Carbene‐Catalyzed Oxidations of Aldehydes Using TEMPO. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.200802735
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