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EDA-Driven Radical Relay Strategy for the Strain-Release Functionalization of Bicyclobutanes
Jatin Patra1, Kousik Saha1, Chandra M R Volla1
1Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai400076, India.
Abstract:
Herein, we unveil a catalyst-free, visible-light-driven radical sulfonylation of bicyclobutanes (BCBs) enabled by an in situ-generated electron donor-acceptor (EDA) complex, providing efficient access to lactam-spirocyclobutyl oxindole sulfones through a cascade of radical cyclization, SO2 incorporation, and strain-release ring opening of BCBs. Comprehensive mechanistic studies, including UV-vis, fluorescence quenching, Job's plot analysis, and EPR spectroscopy, support the formation of EDA complex and light-driven radical intermediacy. The protocol shows broad substrate compatibility and is further extended to an arylsulfonylative cyclization of bicyclobutanes engaging aryl diazonium salts under Ru-photoredox catalysis.
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