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Dual Photoredox/Copper Catalysis for the Remote C(sp3)−H Functionalization of Alcohols and Alkyl Halides by N‐Alkoxypyridinium Salts
Open accessAbstract
Under mild dual photoredox/copper catalysis, the reaction of N‐alkoxypyridinium salts with readily available silyl reagents (TMSN 3, TMSCN, TMSNCS) afforded δ‐azido, δ‐cyano, and δ‐thiocyanato alcohols in high yields. The reaction went through a domino process involving alkoxy radical generation, 1,5‐hydrogen atom transfer (1,5‐HAT) and copper‐catalyzed functionalization of the resulting C‐centered radical. Conditions for catalytic enantioselective δ‐C(sp 3)−H cyanation were also documented.
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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
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Metadata
- Authors
- Bao, X., Wang, Q., & Zhu, J.
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2019-01-18
- Volume
- 58
- Issue
- 7
- Pages
- 2139-2143
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2907318300
- Cited by
- 215
- References
- 1
- FWCI
- 9.38
- Type
- journal article
- Language
- en
- Open access
- green
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- Bao, X., Wang, Q., & Zhu, J. (2019). Dual Photoredox/Copper Catalysis for the Remote C(sp3)−H Functionalization of Alcohols and Alkyl Halides by N‐Alkoxypyridinium Salts. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.201813356
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