C-F bond activation of a perfluorinated ligand leading to nucleophilic fluorination of an organic electrophile

Morgan, Patrick J.; Hanson-Heine, Magnus W.D.; Thomas, Hayden P.; Saunders, Graham C.; Marr, Andrew C.; Licence, Peter

Abstract

We report a fluorine transfer reaction in which fluorine from a perfluorinated ligand undergoes C-F bond activation and transfer to an electrophile, resulting in the formation of a new fluorinated product and dimerization of the mono-defluorinated complex. Treatment of [(?5,?2C-C5Me4CH2C6F5CH2NC3H2NMe)- RhCl] with the organic electrophile, toluoyl chloride, resulted in the formation of a rhodium (III) metallocycle via C-F bond activation assisted defluorinative coupling. Fission of the C-F bond liberated nucleophilic fluoride, which converted acyl chloride to acyl fluoride. The overall reaction was monitored using a multivariant analysis approach in real time.

Citation

Morgan, P. J., Hanson-Heine, M. W., Thomas, H. P., Saunders, G. C., Marr, A. C., & Licence, P. (2020). C-F bond activation of a perfluorinated ligand leading to nucleophilic fluorination of an organic electrophile. Organometallics, 39(11), 2116–2124. https://doi.org/10.1021/acs.organomet.0c00176

• Journal Article Type: Article
• Acceptance Date: Apr 16, 2020
• Online Publication Date: Apr 27, 2020
• Publication Date: Apr 27, 2020
• Deposit Date: Apr 20, 2020
• Publicly Available Date: Apr 28, 2021
• Journal: Organometallics
• Print ISSN: 0276-7333
• Electronic ISSN: 1520-6041
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 39
• Issue: 11
• Pages: 2116–2124
• DOI: https://doi.org/10.1021/acs.organomet.0c00176
• Keywords: Physical and Theoretical Chemistry; Inorganic Chemistry; Organic Chemistry
• Public URL: https://nottingham-repository.worktribe.com/output/4318006
• Publisher URL: https://pubs.acs.org/doi/abs/10.1021/acs.organomet.0c00176