Electrophotocatalytic Radical Cascade Reaction for the Synthesis of Trifluoromethylated Spirocyclobutyl Oxindoles

Abstract

We report an electrophotocatalytic strategy for the radical fluoroalkylation and spirocyclization of bicyclo[1.1.0]butanes. This synergistic method leverages the energy of electricity and light to generate fluoroalkyl radicals from inexpensive Langlois’ reagents under mild, metal-free conditions. Overcoming the limitations of conventional electrochemistry and photoredox catalysis, this protocol provides efficient access to a diverse array of valuable spirocyclobutyl oxindoles bearing CF 3, CF 2 H, and long-chain perfluoroalkyl groups with high functional group tolerance. Mechanistic studies confirm the radical cascade pathway and the essential role of the electrophotocatalytic system.

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