The DOI matches its Crossref record; 47 of the 47 references it cites were found in a registry or an index.
Visible Light-Promoted Metal-Free C–H Activation: Diarylketone-Catalyzed Selective Benzylic Mono- and Difluorination
Open accessAbstract
We report herein an operationally simple method for the direct conversion of benzylic C-H groups to C-F. We show that visible light can activate diarylketones to abstract a benzylic hydrogen atom selectively. Adding a fluorine radical donor yields the benzylic fluoride and regenerates the catalyst. The selective formation of mono- and difluorination products can be achieved by catalyst control. 9-Fluorenone catalyzes benzylic C-H monofluorination, while xanthone catalyzes benzylic C-H difluorination. The scope and efficiency of this new C-H fluorination method are significantly better than those of the existing methods. This is also the first report of selective C-H gem-difluorination.
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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
Monofluorination of Organic Compounds: 10 Years of Innovation
Champagne, P. A., Desroches, J., Hamel, J.-D., Vandamme, M., & Paquin, J.-F. (2015) · Chemical Reviews · doi:10.1021/cr500706a · Cited by 963
Photocatalytic Late-Stage C–H Functionalization
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Photochemical Nickel-Catalyzed C–H Arylation: Synthetic Scope and Mechanistic Investigations
Heitz, D. R., Tellis, J. C., & Molander, G. A. (2016) · Journal of the American Chemical Society · doi:10.1021/jacs.6b04789 · Cited by 518
Contemporary synthetic strategies in organofluorine chemistry
Britton, R., Gouverneur, V., Lin, J.-H., Meanwell, M., Ni, C., Pupo, G., Xiao, J.-C., & Hu, J. (2021) · Nature Reviews Methods Primers · doi:10.1038/s43586-021-00042-1 · Cited by 319
Metadata
- Authors
- Xia, J.-B., Zhu, C., & Chen, C.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2013-11-12
- Volume
- 135
- Issue
- 46
- Pages
- 17494-17500
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2031317139
- Cited by
- 560
- References
- 47
- FWCI
- 21.39
- Type
- journal article
- Language
- en
- Open access
- green
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- Xia, J.-B., Zhu, C., & Chen, C. (2013). Visible Light-Promoted Metal-Free C–H Activation: Diarylketone-Catalyzed Selective Benzylic Mono- and Difluorination. Journal of the American Chemical Society. https://doi.org/10.1021/ja410815u
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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.
