Modular Counter-Fischer–Indole Synthesis through Radical-Enolate Coupling
Hyunho Chung, Jeongyun Kim, Gisela A. González‐Montiel, Paul Ha‐Yeon Cheong, Hong Geun Lee
Abstract
A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.
Topics & Concepts
ChemistryRegioselectivityIndole testDensity functional theorySubstrate (aquarium)KetoneRadical cyclizationFunctional groupModular designCombinatorial chemistryStereochemistryComputational chemistryOrganic chemistryCatalysisOperating systemOceanographyGeologyPolymerComputer scienceCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsRadical Photochemical Reactions