Additions of Aldehyde-Derived Radicals and Nucleophilic <i>N</i>-Alkylindoles to Styrenes by Photoredox Catalysis
Marcel Lux, Martin Klußmann
Abstract
-alkylindole nucleophiles to styrenes was established, as well as some additional radical-nucleophile combinations. Both aryl and aliphatic aldehydes give reasonable yields. The reaction proceeds best for α-substituted styrenes, effectively creating a quaternary all-carbon center. Some iridium-based photoredox systems are catalytically active; furthermore, a base is needed in this transformation. Radicals are formed by reductive perester cleavage and hydrogen atom transfer.
Topics & Concepts
ChemistryRadicalNucleophileAldehydeCatalysisPhotoredox catalysisPhotochemistryNucleophilic additionOrganic chemistryPhotocatalysisRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods