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N-Heterocyclic Carbene-Catalyzed Decarboxylative Alkylation of Aldehydes
Abstract
We found that N-heterocyclic carbene catalysis promoted the unprecedented decarboxylative coupling of aryl aldehydes and tertiary or secondary alkyl carboxylic acid-derived redox-active esters to produce aryl alkyl ketones. The mild and transition-metal-free reaction conditions are attractive features of this method. The power of this protocol was demonstrated by the functionalization of pharmaceutical drugs and natural product. A reaction pathway involving single electron transfer from an enolate form of Breslow intermediate to a redox ester followed by recombination of the resultant radical pair to form a carbon-carbon bond is proposed.
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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
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Metadata
- Authors
- Ishii, T., Kakeno, Y., Nagao, K., & Ohmiya, H.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2019-02-20
- Volume
- 141
- Issue
- 9
- Pages
- 3854-3858
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2915743380
- Cited by
- 336
- References
- 1
- FWCI
- 15.03
- Type
- journal article
- Language
- en
- Open access
- closed
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- Ishii, T., Kakeno, Y., Nagao, K., & Ohmiya, H. (2019). N-Heterocyclic Carbene-Catalyzed Decarboxylative Alkylation of Aldehydes. Journal of the American Chemical Society. https://doi.org/10.1021/jacs.9b00880
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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