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Isolable Analogues of the Breslow Intermediate Derived from Chiral Triazolylidene Carbenes
Open accessAbstract
Since Breslow's initial report on the thiamine mode of action, the study of catalytic acyl carbanion processes has been an area of immense interest. With the advent of azolylidene catalysis, a plethora of reactivtiy has been harnessed, but the crucial nucleophilic intermediate proposed by Breslow had never been isolated or fully characterized. Herein, we report the isolation and full characterization of nitrogen analogues of the Breslow intermediate. Both stable and catalytically relevant, these species provide a model system for the study of acyl carbanion and homoenolate processes catalyzed by triazolylidene carbenes.
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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
Self-citationDiRocco, D. A., & Rovis, T. (2012) · Journal of the American Chemical Society · doi:10.1021/ja3030164 · Cited by 573
Self-citationOrganocatalysis 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
- DiRocco, D. A., Oberg, K. M., & Rovis, T.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2012-03-28
- Volume
- 134
- Issue
- 14
- Pages
- 6143-6145
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1968887784
- Cited by
- 167
- References
- 0
- FWCI
- 8.89
- Type
- journal article
- Language
- en
- Open access
- green
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- DiRocco, D. A., Oberg, K. M., & Rovis, T. (2012). Isolable Analogues of the Breslow Intermediate Derived from Chiral Triazolylidene Carbenes. Journal of the American Chemical Society. https://doi.org/10.1021/ja302031v
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