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α‐Aminoxy‐Acid‐Auxiliary‐Enabled Intermolecular Radical γ‐C(sp3)−H Functionalization of Ketones
Abstract
A method for site‐specific intermolecular γ‐C(sp 3)−H functionalization of ketones has been developed using an α‐aminoxy acid auxiliary applying photoredox catalysis. Regioselective activation of an inert C−H bond is achieved by 1,5‐hydrogen atom abstraction by an oxidatively generated iminyl radical. Tertiary and secondary C‐radicals thus formed at the γ‐position of the imine functionality undergo radical conjugate addition to various Michael acceptors to provide, after reduction and imine hydrolysis, the corresponding γ‐functionalized ketones.
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Cites
Prier, C. K., Rankic, D. A., & MacMillan, D. W. C. (2013) · Chemical Reviews · doi:10.1021/cr300503r · Cited by 9,590
Cited by
Photoredox-Catalyzed C–H Functionalization Reactions
Holmberg-Douglas, N., & Nicewicz, D. A. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00311 · Cited by 989
Guo, W., Wang, Q., & Zhu, J. (2021) · Chemical Society Reviews · doi:10.1039/d0cs00774a · Cited by 423
Kwon, K., Simons, R. T., Nandakumar, M., & Roizen, J. L. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00444 · Cited by 389
Metadata
- Authors
- Jiang, H., & Studer, A.
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2018-01-15
- Volume
- 57
- Issue
- 6
- Pages
- 1692-1696
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2776372515
- Cited by
- 174
- References
- 1
- FWCI
- 10.17
- Type
- journal article
- Language
- en
- Open access
- closed
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- Jiang, H., & Studer, A. (2018). α‐Aminoxy‐Acid‐Auxiliary‐Enabled Intermolecular Radical γ‐C(sp3)−H Functionalization of Ketones. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.201712066
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Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.