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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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Citations
Cited by
Prier, C. K., Rankic, D. A., & MacMillan, D. W. C. (2013) · Chemical Reviews · doi:10.1021/cr300503r · Cited by 9,590
Tay, N. E. S., Lehnherr, D., & Rovis, T. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00384 · Cited by 518
Zou, 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
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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- CoChat. (2026). Citation check: Visible Light-Mediated Intermolecular C−H Functionalization of Electron-Rich Heterocycles with Malonates. https://app.cochat.ai/papers/10.1021/ol101146f
- The paper
- Furst, L., Matsuura, B. S., Narayanam, J. M. R., Tucker, J. W., & Stephenson, C. R. J. (2010). Visible Light-Mediated Intermolecular C−H Functionalization of Electron-Rich Heterocycles with Malonates. Organic Letters. https://doi.org/10.1021/ol101146f
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
