Indole Synthesis by Cobalt-Catalyzed Intramolecular Amidation via the Oxidatively Induced Reductive Elimination Pathway

ACS Catalysis 2024
Aleksandrs Čižikovs, Emīls E Basens, paula Amanda Zagorska, Artis Kinēns, Liene Grigorjeva

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.

Keywords
cobalt | C−H functionalization | indoles | intramolecular amidation | oxidatively induced reductive elimination
DOI
10.1021/acscatal.3c05706
Hyperlink
https://pubs.acs.org/doi/10.1021/acscatal.3c05706

Čižikovs, A., Basens, E., Zagorska, P., Kinēns, A., Grigorjeva, L. Indole Synthesis by Cobalt-Catalyzed Intramolecular Amidation via the Oxidatively Induced Reductive Elimination Pathway. ACS Catalysis, 2024, Vol. 14, No. 3, pp.1690-1698. ISSN 2155-5435. Available from: doi:10.1021/acscatal.3c05706

Publication language
English (en)