Elemental Sulfur-Mediated Transformation of Carboxylic Acids to Acyl Fluorides by Electrophilic Fluorinating Reagent, Selectfluor
Elsayed M. Mahmoud, Soichiro Mori, Yuji Sumii, Norio Shibata
Abstract
The elemental sulfur-mediated synthesis of acyl fluorides from carboxylic acids is achieved using Selectfluor. A broad range of acyl fluorides are accessible from carboxylic acids while avoiding the formation of acid anhydrides. 19 F NMR spectra suggest that S 8 -fluoro-sulfonium cation A and neutral S 8 -difluoride A′ generated in situ are the reactive species in this deoxyfluorination reaction.
Topics & Concepts
ChemistrySelectfluorSulfoniumElectrophileReagentSulfurCarboxylic acidElectrophilic fluorinationOrganic chemistryHalogenSalt (chemistry)CatalysisAlkylFluorine in Organic ChemistrySulfur-Based Synthesis TechniquesCarbohydrate Chemistry and Synthesis