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Published on: May 21, 2019
Photoredox Fe-Catalyzed Truce-Smiles Rearrangement of N-Arylsulfonyl Acrylamides with Aliphatic Carboxylic Acids
Ruoli Huang1,2, Depeng Duan1,2, Niankai Fu3
1State Key Laboratory of Bioinspired Interfacial Materials Science, Bioinspired Science Innovation Center, Hangzhou International Innovation Institute, Beihang University, Hangzhou 311115, China.
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 CF2H-containing arylethylamines. The catalytic system is amenable to gram-scale synthesis, and mechanistic investigations support a radical-mediated mechanism involving intramolecular aryl migration.
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