Nucleophilic Fluorination Catalyzed by a Cyclometallated Rhodium Complex

Morgan, Patrick J., Saunders, Graham C., Macgregor, Stuart A., Marr, Andrew C. and Licence, Peter ORCID: https://orcid.org/0000-0003-2992-0153 (2022) Nucleophilic Fluorination Catalyzed by a Cyclometallated Rhodium Complex. Organometallics, 41 (7). pp. 883-891. ISSN 0276-7333

[thumbnail of om2c00052]
Preview
PDF (om2c00052) - Published Version
Available under License Creative Commons Attribution.

Download (3MB) | Preview

Abstract

Quantitative catalytic nucleophilic fluorination of a range of acyl chlorides to acyl fluorides was promoted by a cyclometallated rhodium complex [(η5,κ2C-C5Me4CH2C6F5CH2NC3H2NMe)- RhCl] (1). 1 can be prepared in high yields from commercially available starting materials using a one-pot method. The catalyst could be separated, regenerated, and reused. Rapid quantitative fluorination generated the fluoride analogue of the active pharmaceutical ingredient probenecid. Infrared in situ monitoring verified the clean conversion of the substrates to products. VTNA graphical kinetic analysis and DFT calculations lead to a postulated reaction mechanism involving a nucleophilic Rh-F bond.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry, Pharmacy and Pharmacology
Related URLs:
Depositing User: LivePure Connector
Date Deposited: 07 Oct 2026 08:51
Last Modified: 11 Oct 2026 05:27
URI: https://ueaeprints.uea.ac.uk/id/eprint/104743
DOI: 10.1021/acs.organomet.2c00052

Downloads

Downloads per month over past year

Actions (login required)

View Item View Item