Indole Synthesis by Cobalt-Catalyzed Intramolecular Amidation via the Oxidatively Induced Reductive Elimination Pathway
Aleksandrs Čižikovs, Emils E. Basens, Paula A. Zagorska, Artis Kinēns, Liene Grigorjeva
Abstract
C–H bond activation and functionalization using high-valent cobalt catalysis typically involves a Co(III)/Co(I) catalytic cycle. Because of the lack of evidence and challenges associated with the high reactivity and instability of Co(IV) intermediates, reports on the C–H functionalization mechanism investigation involving Co(IV) intermediacy are still underexplored. Herein, we report an efficient synthesis of indole-2-carboxylic esters via intramolecular amidation of α-amidoacrylates and experimental and computational studies of the reaction mechanism, which involves oxidatively induced reductive elimination from Co(IV) species.
Topics & Concepts
Intramolecular forceReductive eliminationChemistryCatalysisIndole testReactivity (psychology)CobaltCatalytic cycleSurface modificationCombinatorial chemistryReaction mechanismMedicinal chemistryStereochemistryOrganic chemistryPathologyMedicinePhysical chemistryAlternative medicineCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsRadical Photochemical Reactions