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Hydrodefluorination of Perfluoroalkyl Groups Using Silylium-Carborane Catalysts
Abstract
Carbon-fluorine bonds are among the most unreactive functionalities in chemistry. Interest in their activation arises in part from the high global warming potentials of anthropogenic polyfluoroorganic compounds. Conversion to carbon-hydrogen bonds (hydrodefluorination) is the simplest modification of carbon-fluorine bonds, but efficient catalytic hydrodefluorination of perfluoroalkyl groups has been an unmet challenge. We report a class of carborane-supported, highly electrophilic silylium compounds that act as long-lived catalysts for hydrodefluorination of trifluoromethyl and nonafluorobutyl groups by widely accessible silanes under mild conditions. The reactions are completely selective for aliphatic carbon-fluorine bonds in preference to aromatic carbon-fluorine bonds.
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Cited by
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Stahl, T., Klare, H. F. T., & Oestreich, M. (2013) · ACS Catalysis · doi:10.1021/cs4003244 · Cited by 470
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Chan, P. W. Y., Yakunin, A. F., Edwards, E. A., & Pai, E. F. (2011) · Journal of the American Chemical Society · doi:10.1021/ja200277d · Cited by 107
Decomposition kinetics of perfluorinated sulfonic acids
Khan, M. Y., So, S., & da Silva, G. (2020) · Chemosphere · doi:10.1016/j.chemosphere.2019.124615 · Cited by 101
Khusnutdinova, A. N., Batyrova, K. A., Brown, G., Fedorchuk, T., Chai, Y. S., Skarina, T., Flick, R., Petit, A., Savchenko, A., Stogios, P., et al. (2023) · The FEBS Journal · doi:10.1111/febs.16903 · Cited by 40
Unraveling the nature of the catalytic power of fluoroacetate dehalogenase
Miranda‐Rojas, S., Fernández, I., Kästner, J., Toro‐Labbé, A., & Mendizábal, F. (2018) · ChemCatChem · doi:10.1002/cctc.201701517 · Cited by 23
Metadata
- Authors
- Douvris, C., & Ozerov, O. V.
- Venue
- Science
- Published
- 2008-08-29
- Volume
- 321
- Issue
- 5893
- Pages
- 1188-1190
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- OpenAlex
- W1992124690
- Cited by
- 580
- References
- 0
- FWCI
- 20.50
- Type
- journal article
- Language
- en
- Open access
- closed
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- Douvris, C., & Ozerov, O. V. (2008). Hydrodefluorination of Perfluoroalkyl Groups Using Silylium-Carborane Catalysts. Science. https://doi.org/10.1126/science.1159979
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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.
