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Visible-Light Photo-Arbuzov Reaction of Aryl Bromides and Trialkyl Phosphites Yielding Aryl Phosphonates
Abstract
Aryl phosphonates are functional groups frequently found in pharmaceutical and crop protection agents. For their synthesis via C–P bond formation typically transition-metal-catalyzed reactions are used. We report a visible-light photo-Arbuzov reaction as an efficient, mild, and metal-free alternative. Rhodamine 6G (Rh.6G) is used as the photocatalyst, generating aryl radicals under blue light. Coupling of the radicals with a wide range of trivalent phosphites gives aryl phosphonates in good to very good isolated yields. The mild reaction conditions allow the introduction of a phosphonate group into complex and sensitive pharmaceutically active molecules such as benzodiazepams and nicergoline by the activation of a carbon–halogen bond.
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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
Speckmeier, E., Fischer, T. G., & Zeitler, K. (2018) · Journal of the American Chemical Society · doi:10.1021/jacs.8b08933 · Cited by 771
Stache, E. E., Ertel, A. B., Rovis, T., & Doyle, A. G. (2018) · ACS Catalysis · doi:10.1021/acscatal.8b03592 · Cited by 366
Zafar, Z., Yi, S., Li, J., Li, C., Zhu, Y., Zada, A., Yao, W., Liu, Z., & Yue, X. (2022) · ENERGY & ENVIRONMENTAL MATERIALS · doi:10.1002/eem2.12171 · Cited by 284
Xu, J., Cao, J., Wu, X., Wang, H., Yang, X., Tang, X., Toh, R. W., Zhou, R., Yeow, E. K. L., & Wu, J. (2021) · Journal of the American Chemical Society · doi:10.1021/jacs.1c05994 · Cited by 280
Metadata
- Authors
- Shaikh, R. S., Düsel, S. J. S., & König, B.
- Venue
- ACS Catalysis
- Publisher
- American Chemical Society (ACS)
- Published
- 2016-11-21
- Volume
- 6
- Issue
- 12
- Pages
- 8410-8414
- ISSN
- 2155-5435 (ISSN-L)
- OpenAlex
- W2550192427
- Cited by
- 188
- References
- 1
- FWCI
- 8.32
- Type
- journal article
- Language
- en
- Open access
- closed
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- Shaikh, R. S., Düsel, S. J. S., & König, B. (2016). Visible-Light Photo-Arbuzov Reaction of Aryl Bromides and Trialkyl Phosphites Yielding Aryl Phosphonates. ACS Catalysis. https://doi.org/10.1021/acscatal.6b02591
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