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Photoinduced Remote Functionalization of Amides and Amines Using Electrophilic Nitrogen Radicals
Open accessAbstract
The selective functionalization of C(sp 3)−H bonds at distal positions to functional groups is a challenging task in synthetic chemistry. Reported here is a photoinduced radical cascade strategy for the divergent functionalization of amides and protected amines. The process is based on the oxidative generation of electrophilic amidyl radicals and their subsequent transposition by 1,5‐H‐atom transfer, resulting in remote fluorination, chlorination and, for the first time, thioetherification, cyanation, and alkynylation. The process is tolerant of most common functional groups and delivers useful building blocks that can be further elaborated. The utility of this strategy is demonstrated through the late‐stage functionalization of amino acids and a dipeptide.
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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
Photoredox-Catalyzed C–H Functionalization Reactions
Holmberg-Douglas, N., & Nicewicz, D. A. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00311 · Cited by 989
Speckmeier, E., Fischer, T. G., & Zeitler, K. (2018) · Journal of the American Chemical Society · doi:10.1021/jacs.8b08933 · Cited by 771
Photocatalytic Late-Stage C–H Functionalization
Bellotti, P., Huang, H.-M., Faber, T., & Glorius, F. (2023) · Chemical Reviews · doi:10.1021/acs.chemrev.2c00478 · Cited by 623
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
- Morcillo, S. P., Dauncey, E. M., Kim, J. H., Douglas, J. J., Sheikh, N. S., & Leonori, D.
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2018-08-29
- Volume
- 57
- Issue
- 39
- Pages
- 12945-12949
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2887102484
- Cited by
- 273
- References
- 1
- FWCI
- 14.46
- Type
- journal article
- Language
- en
- Open access
- hybrid
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- Morcillo, S. P., Dauncey, E. M., Kim, J. H., Douglas, J. J., Sheikh, N. S., & Leonori, D. (2018). Photoinduced Remote Functionalization of Amides and Amines Using Electrophilic Nitrogen Radicals. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.201807941
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