Skip to main content

Research Repository

Advanced Search

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

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


Authors

Patrick J. Morgan

Magnus W.D. Hanson-Heine

Hayden P. Thomas

Graham C. Saunders

Andrew C. Marr



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 Mar 29, 2024
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

Files

Pet Licence C-F Bond Activation (3.1 Mb)
PDF

Copyright Statement
Published under ACS Author Choice Licence




You might also like



Downloadable Citations