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Nucleophilic Aryl Fluorination and Aryl Halide Exchange Mediated by a CuI/CuIII Catalytic Cycle
Abstract
Copper-catalyzed halide exchange reactions under very mild reaction conditions are described for the first time using a family of model aryl halide substrates. All combinations of halide exchange (I, Br, Cl, F) are observed using catalytic amounts of Cu(I). Strikingly, quantitative fluorination of aryl-X substrates is also achieved catalytically at room temperature, using common F(-) sources, via the intermediacy of aryl-Cu(III)-X species. Experimental and computational data support a redox Cu(I)/Cu(III) catalytic cycle involving aryl-X oxidative addition at the Cu(I) center, followed by halide exchange and reductive elimination steps. Additionally, defluorination of the aryl-F model system can be also achieved with Cu(I) at room temperature operating under a Cu(I)/Cu(III) redox pair.
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Cited by
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Chen, Z., Wang, B., Zhang, J., Yu, W., Liu, Z., & Zhang, Y. (2015) · Organic Chemistry Frontiers · doi:10.1039/c5qo00004a · Cited by 1,533
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
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Beletskaya, I. P., & Cheprakov, A. V. (2012) · Organometallics · doi:10.1021/om300683c · Cited by 454
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
Taylor, S. J., Stauber, J., Bohorquez, O., Tatsumi, G., Kumari, R., Chakraborty, J., Bartholdy, B. A., Schwenger, E., Sundaravel, S., Farahat, A. A., et al. (2024) · Nature Genetics · doi:10.1038/s41588-024-01911-7 · Cited by 22
Metadata
- Authors
- Casitas, A., Canta, M., Solà, M., Costas, M., & Ribas, X.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2011-11-14
- Volume
- 133
- Issue
- 48
- Pages
- 19386-19392
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2324385177
- Cited by
- 262
- References
- 0
- FWCI
- 12.39
- Type
- journal article
- Language
- en
- Open access
- closed
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- Casitas, A., Canta, M., Solà, M., Costas, M., & Ribas, X. (2011). Nucleophilic Aryl Fluorination and Aryl Halide Exchange Mediated by a CuI/CuIII Catalytic Cycle. Journal of the American Chemical Society. https://doi.org/10.1021/ja2058567
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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