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Electron Transfer Photoredox Catalysis: Intramolecular Radical Addition to Indoles and Pyrroles
Abstract
The utilization of the photoredox catalyst, tris(2,2'-bipyridyl)ruthenium dichloride, and a household light bulb to effect radical cyclizations onto indoles and pyrroles at room temperature is reported. A reactive free radical intermediate is generated via the reduction of an activated C-Br bond by the single electron reductant, Ru(I), generated in a visible light induced photocatalytic cycle. This system represents an expansion of the application of photoredox catalysis in conventional free radical processes.
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Citations
Cited by
Prier, C. K., Rankic, D. A., & MacMillan, D. W. C. (2013) · Chemical Reviews · doi:10.1021/cr300503r · Cited by 9,590
Visible light photocatalysis as a greener approach to photochemical synthesis
Yoon, T. P., Ischay, M. A., & Du, J. (2010) · Nature Chemistry · doi:10.1038/nchem.687 · Cited by 2,657
Photoredox-Catalyzed C–H Functionalization Reactions
Holmberg-Douglas, N., & Nicewicz, D. A. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00311 · Cited by 989
Nguyen, J. D., Tucker, J. W., Konieczynska, M. D., & Stephenson, C. R. J. (2011) · Journal of the American Chemical Society · doi:10.1021/ja108560e · Cited by 772
Self-citationSynthetic applications of photoredox catalysis with visible light
Xi, Y., Yi, H., & Lei, A. (2013) · Organic & Biomolecular Chemistry · doi:10.1039/c3ob40137e · Cited by 658
Metadata
- Authors
- Tucker, J. W., Narayanam, J. M. R., Krabbe, S. W., & Stephenson, C. R. J.
- Venue
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2009-12-16
- Volume
- 12
- Issue
- 2
- Pages
- 368-371
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- OpenAlex
- W2085712428
- Cited by
- 331
- References
- 0
- FWCI
- 15.80
- Type
- journal article
- Language
- en
- Open access
- closed
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- Tucker, J. W., Narayanam, J. M. R., Krabbe, S. W., & Stephenson, C. R. J. (2010). Electron Transfer Photoredox Catalysis: Intramolecular Radical Addition to Indoles and Pyrroles. Organic Letters. https://doi.org/10.1021/ol902703k
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