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Oxidative Aliphatic C-H Fluorination with Fluoride Ion Catalyzed by a Manganese Porphyrin
Abstract
Fluorine's Smooth Introduction: Carbon-fluorine bonds are emerging as increasingly versatile constituents of drugs, agrochemicals, and positron emission tomography tracers. Elemental F 2 gas is in principle an efficient reagent for their preparation, but its extreme reactivity requires special handling precautions. Substantial research has therefore focused on promoting selective reactivity of more conveniently handled fluoride ion salts. Liu et al. (p. 1322 ) present a manganese catalyst that transfers fluoride to a range of hydrocarbons in conjunction with a hypervalent iodine-based oxidant. Mechanistic studies implicate a manganese difluoride intermediate that reacts with alkyl radicals generated by a preceding manganese oxo.
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Cites
Lee, C., Yang, W., & Parr, R. G. (1988) · Physical Review B · doi:10.1103/physrevb.37.785 · Cited by 100,874
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A new mixing of Hartree–Fock and local density-functional theories
Becke, A. D. (1993) · The Journal of Chemical Physics · doi:10.1063/1.464304 · Cited by 16,515
Reactive oxygen species have a causal role in multiple forms of insulin resistance
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Herceptin acts as an anti-angiogenic cocktail
Izumi, Y., Xu, L., di Tomaso, E., Fukumura, D., & Jain, R. K. (2002) · Nature · doi:10.1038/416279b · Cited by 623
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Synthetic Applications of Proton-Coupled Electron Transfer
Gentry, E. C., & Knowles, R. R. (2016) · Accounts of Chemical Research · doi:10.1021/acs.accounts.6b00272 · Cited by 773
Transition‐Metal‐Catalyzed Selective Functionalization of C(sp3)−H Bonds in Natural Products
Karimov, R. R., & Hartwig, J. F. (2018) · Angewandte Chemie International Edition · doi:10.1002/anie.201710330 · Cited by 341
Metadata
- Authors
- Liu, W., Huang, X., Cheng, M.-J., Nielsen, R. J., Goddard, W. A., & Groves, J. T.
- Venue
- Science
- Published
- 2012-09-14
- Volume
- 337
- Issue
- 6100
- Pages
- 1322-1325
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- OpenAlex
- W1977262764
- Cited by
- 566
- References
- 5
- FWCI
- 28.74
- Type
- journal article
- Language
- en
- Open access
- closed
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- Liu, W., Huang, X., Cheng, M.-J., Nielsen, R. J., Goddard, W. A., & Groves, J. T. (2012). Oxidative Aliphatic C-H Fluorination with Fluoride Ion Catalyzed by a Manganese Porphyrin. Science. https://doi.org/10.1126/science.1222327
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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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