Nucleophilic Fluorination Catalyzed by a Cyclometallated Rhodium Complex

Patrick J. Morgan, Graham C. Saunders, Stuart A. Macgregor, Andrew C. Marr, Peter Licence*

*Corresponding author for this work

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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.

Original languageEnglish
Pages (from-to)883–891
Number of pages9
JournalOrganometallics
Volume41
Issue number7
Early online date31 Mar 2022
DOIs
Publication statusPublished - 11 Apr 2022

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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