Photoredox Fe-Catalyzed Truce–Smiles Rearrangement of <i>N</i> -Arylsulfonyl Acrylamides with Aliphatic Carboxylic Acids
Ruoli Huang, Depeng Duan, Niankai Fu, Song Lu
Abstract
Herein, we report a photoredox Fe-catalyzed, redox-neutral Truce–Smiles rearrangement of N -arylsulfonyl acrylamides using readily available aliphatic carboxylic acids as radical precursors. This method accommodates a broad range of alkyl carboxylic acids, including difluoroacetic acid, enabling efficient access to functionalized amides that can be readily transformed into valuable CF 2 H-containing arylethylamines. The catalytic system is amenable to gram-scale synthesis, and mechanistic investigations support a radical-mediated mechanism involving intramolecular aryl migration.
Topics & Concepts
ChemistryIntramolecular forceArylAlkylCarboxylic acidCatalysisPhotoredox catalysisOrganic chemistryCombinatorial chemistryReaction conditionsIntramolecular reactionReaction mechanismAliphatic compoundPrimary (astronomy)Mechanism (biology)Radical Photochemical ReactionsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions