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Visible-Light-Promoted Remote C(sp3)–H Amidation and Chlorination
Abstract
A visible-light-promoted C(sp(3))-H amidation and chlorination of N-chlorosulfonamides (NCSs) is reported. This remote C(sp(3))-H functionalization can be achieved in weak basic solution at room temperature with as little as 0.1 mol % of a photocatalyst. A variety of nitrogen-containing heterocycles (up to 94% yield) and chlorides (up to 93% yield) are prepared from NCSs. Late-stage C(sp(3))-H functionalization of complex and biologically important (-)-cis-myrtanylamine and (+)-dehydroabietylamine derivatives can also be achieved with excellent yields and regioselectivity.
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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
Teegardin, K., Day, J. I., Chan, J., & Weaver, J. (2016) · Organic Process Research & Development · doi:10.1021/acs.oprd.6b00101 · Cited by 593
Tay, N. E. S., Lehnherr, D., & Rovis, T. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00384 · Cited by 518
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
- Qin, Q., & Yu, S.
- Venue
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2015-04-08
- Volume
- 17
- Issue
- 8
- Pages
- 1894-1897
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- OpenAlex
- W2313590131
- Cited by
- 213
- References
- 1
- FWCI
- 13.04
- Type
- journal article
- Language
- en
- Open access
- closed
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- Qin, Q., & Yu, S. (2015). Visible-Light-Promoted Remote C(sp3)–H Amidation and Chlorination. Organic Letters. https://doi.org/10.1021/acs.orglett.5b00582
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