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Iminyl‐Radicals by Oxidation of α‐Imino‐oxy Acids: Photoredox‐Neutral Alkene Carboimination for the Synthesis of Pyrrolines
Abstract
The visible‐light‐promoted decarboxylation of α‐imino‐oxy propionic acids for the generation of iminyl radicals has been accomplished through the use of Ir(dFCF 3 ppy)2(dtbbpy)PF 6 as a photoredox catalyst. Different from visible‐light‐promoted homolysis and single‐electron reduction of oxime derivatives, this strategy provides a novel catalytic cycle for alkene carboimination through a sequence comprising N‐radical generation, iminyl radical cyclization, intermolecular conjugate addition to a Michael acceptor, and single‐electron reduction to afford various pyrroline derivatives in an overall redox‐neutral process. The indolizidine alkaloid skeleton could be easily constructed from a pyrroline derivative prepared by this synthetic method.
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Prier, C. K., Rankic, D. A., & MacMillan, D. W. C. (2013) · Chemical Reviews · doi:10.1021/cr300503r · Cited by 9,590
Cited by
Pratley, C., Fenner, S., & Murphy, J. A. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00831 · Cited by 422
Kwon, K., Simons, R. T., Nandakumar, M., & Roizen, J. L. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00444 · Cited by 389
Yu, X., Chen, J., Wang, P., Yang, M., Liang, D., & Xiao, W. (2018) · Angewandte Chemie International Edition · doi:10.1002/anie.201710618 · Cited by 344
Hydroxylamine Derivatives as Nitrogen‐Radical Precursors in Visible‐Light Photochemistry
Davies, J., Morcillo, S. P., Douglas, J. J., & Leonori, D. (2018) · Chemistry – A European Journal · doi:10.1002/chem.201801655 · Cited by 312
Direct decarboxylative Giese reactions
Kitcatt, D. M., Nicolle, S., & Lee, A.-L. (2022) · Chemical Society Reviews · doi:10.1039/d1cs01168e · Cited by 257
Metadata
- Authors
- Jiang, H., & Studer, A.
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2017-09-05
- Volume
- 56
- Issue
- 40
- Pages
- 12273-12276
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2744634997
- Cited by
- 231
- References
- 1
- FWCI
- 12.27
- Type
- journal article
- Language
- en
- Open access
- closed
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- Jiang, H., & Studer, A. (2017). Iminyl‐Radicals by Oxidation of α‐Imino‐oxy Acids: Photoredox‐Neutral Alkene Carboimination for the Synthesis of Pyrrolines. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.201706270
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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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