The DOI matches its Crossref record.
Visible Light-Mediated Intermolecular C−H Functionalization of Electron-Rich Heterocycles with Malonates
Abstract
The photoredox-mediated direct intermolecular C-H functionalization of substituted indoles, pyrroles, and furans with diethyl bromomalonate is described, utilizing the visible light-induced reductive quenching pathway of Ru(bpy)(3)Cl(2). An analysis of reductive quenchers and mechanistic considerations has led to an optimized protocol for the heteroaromatic alkylations, providing products in good yields and regioselectivities, as well as successfully eliminating previously observed competitive side reactions. This methodology is highlighted by its neutral conditions, activity at ambient temperatures, low catalyst loading, functional group tolerance, and chemoselectivity.
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Cited by
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Self-citationPhotoredox-Catalyzed C–H Functionalization Reactions
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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
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Illuminating Photoredox Catalysis
McAtee, R. C., McClain, E. J., & Stephenson, C. R. J. (2019) · Trends in Chemistry · doi:10.1016/j.trechm.2019.01.008 · Cited by 473
Self-citationZou, Y., Lu, L., Fu, L., Chang, N., Rong, J., Chen, J., & Xiao, W. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201102306 · Cited by 435
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Total Synthesis of (+)‐Gliocladin C Enabled by Visible‐Light Photoredox Catalysis
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Metadata
- Authors
- Furst, L., Matsuura, B. S., Narayanam, J. M. R., Tucker, J. W., & Stephenson, C. R. J.
- Venue
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2010-06-02
- Volume
- 12
- Issue
- 13
- Pages
- 3104-3107
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- OpenAlex
- W2079822650
- Cited by
- 363
- References
- 0
- FWCI
- 17.21
- Type
- journal article
- Language
- en
- Open access
- closed
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