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Umpolung of Michael Acceptors Catalyzed by N-Heterocyclic Carbenes
Open accessAbstract
N-Heterocyclic carbenes can catalyze beta-alkylations of a range of alpha,beta-unsaturated esters, amides, and nitriles that bear pendant leaving groups to form a variety of ring sizes. In this process, the nucleophilic catalyst transiently transforms the normally electrophilic beta carbon into a nucleophilic site through an unanticipated addition-tautomerization sequence.
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Citations
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
Complexes with Poly(N-heterocyclic carbene) Ligands: Structural Features and Catalytic Applications
Poyatos, M., Mata, J. A., & Peris, E. (2009) · Chemical Reviews · doi:10.1021/cr800501s · Cited by 848
N‐heterocyclische Carbene als Organokatalysatoren
Marion, N., Díez‐González, S., & Nolan, S. P. (2007) · Angewandte Chemie · doi:10.1002/ange.200603380 · Cited by 428
Chen, X.-Y., Gao, Z.-H., & Ye, S. (2020) · Accounts of Chemical Research · doi:10.1021/acs.accounts.9b00635 · Cited by 386
Organocatalysis in biorefining for biomass conversion and upgrading
Liu, D. (. J. )., & Chen, E. Y.-X. (2014) · Green Chem. · doi:10.1039/c3gc41934g · Cited by 101
Metadata
- Authors
- Fischer, C., Smith, S. W., Powell, D. A., & Fu, G. C.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-01-17
- Volume
- 128
- Issue
- 5
- Pages
- 1472-1473
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2084555382
- Cited by
- 273
- References
- 0
- FWCI
- 8.38
- Type
- journal article
- Language
- en
- Open access
- green
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- Fischer, C., Smith, S. W., Powell, D. A., & Fu, G. C. (2006). Umpolung of Michael Acceptors Catalyzed by N-Heterocyclic Carbenes. Journal of the American Chemical Society. https://doi.org/10.1021/ja058222q
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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.
