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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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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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