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Selective Late‐Stage Oxygenation of Sulfides with Ground‐State Oxygen by Uranyl Photocatalysis
Abstract
Oxygenation is a fundamental transformation in synthesis. Herein, we describe the selective late‐stage oxygenation of sulfur‐containing complex molecules with ground‐state oxygen under ambient conditions. The high oxidation potential of the active uranyl cation (UO 22+) enabled the efficient synthesis of sulfones. The ligand‐to‐metal charge transfer process (LMCT) from O 2p to U 5f within the O=U=O group, which generates a U V center and an oxygen radical, is assumed to be affected by the solvent and additives, and can be tuned to promote selective sulfoxidation. This tunable strategy enabled the batch synthesis of 32 pharmaceuticals and analogues by late‐stage oxygenation in an atom‐ and step‐efficient manner.
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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
Jacob, C. (2006) · Natural Product Reports · doi:10.1039/b609523m · Cited by 373
Cited by
Tay, N. E. S., Lehnherr, D., & Rovis, T. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00384 · Cited by 518
Construction of Thioamide Peptides from Chiral Amino Acids
Liao, Y., Zhang, S., & Jiang, X. (2023) · Angewandte Chemie International Edition · doi:10.1002/anie.202303625 · Cited by 27
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Metadata
- Authors
- Li, Y., Rizvi, S. A., Hu, D., Sun, D., Gao, A., Zhou, Y., Li, J., & Jiang, X.
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2019-08-08
- Volume
- 58
- Issue
- 38
- Pages
- 13499-13506
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2958545013
- Cited by
- 246
- References
- 2
- FWCI
- 11.85
- Type
- journal article
- Language
- en
- Open access
- closed
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- Li, Y., Rizvi, S. A., Hu, D., Sun, D., Gao, A., Zhou, Y., Li, J., & Jiang, X. (2019). Selective Late‐Stage Oxygenation of Sulfides with Ground‐State Oxygen by Uranyl Photocatalysis. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.201906080
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