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- Title
A 2,2‐Difluoroimidazolidine Derivative for Deoxyfluorination Reactions: Mechanistic Insights by Experimental and Computational Studies.
- Authors
Herbstritt, Domenique; Tomar, Pooja; Müller, Robert; Kaupp, Martin; Braun, Thomas
- Abstract
A N‐heterocyclic deoxyfluorinating agent SIMesF2 was synthesized by nucleophilic fluorination of N,N‐1,3‐dimesityl‐2‐chloroimidazolidinium chloride (3) at room temperature. SIMesF2 was applied to deoxyfluorinate carboxylic acids and alcohols and convert benzaldehyde into difluorotoluene. Mechanistic studies by NMR spectroscopy suggest reaction pathways of the carboxylic acid to acyl fluoride via outer‐sphere fluorinations at an imidazolidinium ion by polyfluoride. DFT studies give further insight by exploring mechanistic details which distinguish the fluorination of aldehydes from that of carboxylic acids. Furthermore, a consecutive reaction sequence for the oxidation of an aldehyde followed by in situ fluorination of the generated carboxylic acid was developed.
- Subjects
CARBOXYLIC acids; NUCLEAR magnetic resonance spectroscopy; FLUORINATION; ALDEHYDES
- Publication
Chemistry - A European Journal, 2023, Vol 29, Issue 58, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202301556