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Visible-Light Photoredox Catalysis: Aza-Henry Reactions via C−H Functionalization
Abstract
We report the application of visible-light photoredox catalysis for the formation of C-C bonds between tertiary N-arylamines and nitroalkanes via an oxidative aza-Henry reaction. In the presence of 1 mol % Ir(ppy)(2)(dtbbpy)PF(6), efficient coupling of nitroalkanes with in situ-generated iminium ions provides the desired products in up to 96% yield. Mechanistic studies suggest that reductive quenching of the Ir(3+) excited state by the tertiary amine leads to the ammonium radical cation, with subsequent catalyst turnover (Ir(2+) --> Ir(3+)) likely effected by atmospheric oxygen.
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Citations
Cited by
Prier, C. K., Rankic, D. A., & MacMillan, D. W. C. (2013) · Chemical Reviews · doi:10.1021/cr300503r · Cited by 9,590
You, Y., & Nam, W. (2012) · Chemical Society Reviews · doi:10.1039/c2cs35171d · Cited by 668
Zou, Y., Lu, L., Fu, L., Chang, N., Rong, J., Chen, J., & Xiao, W. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201102306 · Cited by 435
Metadata
- Authors
- Condie, A. G., González-Gómez, J. C., & Stephenson, C. R. J.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2010-01-13
- Volume
- 132
- Issue
- 5
- Pages
- 1464-1465
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1999031172
- Cited by
- 822
- References
- 0
- FWCI
- 34.57
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Visible-Light Photoredox Catalysis: Aza-Henry Reactions via C−H Functionalization. https://app.cochat.ai/papers/10.1021/ja909145y
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- Condie, A. G., González-Gómez, J. C., & Stephenson, C. R. J. (2010). Visible-Light Photoredox Catalysis: Aza-Henry Reactions via C−H Functionalization. Journal of the American Chemical Society. https://doi.org/10.1021/ja909145y
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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.
