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Mechanism of C−F Reductive Elimination from Palladium(IV) Fluorides
Open accessAbstract
The first systematic mechanism study of C-F reductive elimination from a transition metal complex is described. C-F bond formation from three different Pd(IV) fluoride complexes was mechanistically evaluated. The experimental data suggest that reductive elimination occurs from cationic Pd(IV) fluoride complexes via a dissociative mechanism. The ancillary pyridyl-sulfonamide ligand plays a crucial role for C-F reductive elimination, likely due to a kappa(3) coordination mode, in which an oxygen atom of the sulfonyl group coordinates to Pd. The pyridyl-sulfonamide can support Pd(IV) and has the appropriate geometry and electronic structure to induce reductive elimination.
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Cites
Asymmetric autocatalysis and amplification of enantiomeric excess of a chiral molecule
Soai, K., Shibata, T., Morioka, H., & Choji, K. (1995) · Nature · doi:10.1038/378767a0 · Cited by 1,085
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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
Nickel-Mediated Oxidative Fluorination for PET with Aqueous [18F] Fluoride
Lee, E., Hooker, J. M., & Ritter, T. (2012) · Journal of the American Chemical Society · doi:10.1021/ja3084797 · Cited by 286
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Metadata
- Authors
- Furuya, T., Benitez, D., Tkatchouk, E., Strom, A. E., Tang, P., Goddard, W. A., & Ritter, T.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2010-03-02
- Volume
- 132
- Issue
- 11
- Pages
- 3793-3807
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2119203509
- Cited by
- 293
- References
- 1
- FWCI
- 19.26
- Type
- journal article
- Language
- en
- Open access
- green
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- Furuya, T., Benitez, D., Tkatchouk, E., Strom, A. E., Tang, P., Goddard, W. A., & Ritter, T. (2010). Mechanism of C−F Reductive Elimination from Palladium(IV) Fluorides. Journal of the American Chemical Society. https://doi.org/10.1021/ja909371t
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