Photoredox Catalysis toward 2-Sulfenylindole Synthesis through a Radical Cascade Process
Marilia S Santos1, Hugo L I Betim1, Camila M Kisukuri1
1Center of Excellence for Research in Sustainable Chemistry (CERSusChem), Department of Chemistry, Federal University of São Carlos, Rodovia Washington Luís, km 235, São Carlos, SP 13565-905, Brazil.
Abstract:
A radical cascade process initiated through visible-light induced thiyl radical coupling with ortho-substituted arylisocianides followed by an intramolecular cyclization and subsequent aromatization to access 2-sulfenylindoles is described. The key thiyl radicals are promptly generated via a hydrogen atom transfer event. The redox-neutral protocol features broad substrate scope, excellent functional group tolerance, and mild reaction conditions. Furthermore, the implementation of a continuous flow variant allows smooth scalability with a short residence time through process intensification.
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