A 2,2-Difluoroimidazolidine Derivative for Deoxyfluorination Reactions: Mechanistic Insights by Experimental and
Domenique Herbstritt1, Pooja Tomar1, Robert Müller2
1Department of Chemistry, Humboldt-Universität zu Berlin, Brook-Taylor-Str. 2, 12489, Berlin, Germany.
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.
More Related Videos
08:43Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
08:46Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
Published on: July 26, 2018
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
