Photoredox Catalysis toward 2-Sulfenylindole Synthesis through a Radical Cascade Process
Marília S. Santos, Hugo L. I. Betim, Camila M. Kisukuri, José A. C. Delgado, Arlene G. Corrêa, Márcio W. Paixão
Abstract
-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.
Topics & Concepts
ChemistryAromatizationIntramolecular forceRadicalCatalysisCascadePhotochemistryFunctional groupSubstrate (aquarium)Combinatorial chemistryHydrogen atomGroup (periodic table)StereochemistryOrganic chemistryOceanographyChromatographyGeologyPolymerRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods