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Ryu, Ho
분자활성 촉매반응 연구단
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Oxidatively induced reactivity in Rh(iii)-catalyzed 7-azaindole synthesis: insights into the role of the silver additive

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Title
Oxidatively induced reactivity in Rh(iii)-catalyzed 7-azaindole synthesis: insights into the role of the silver additive
Author(s)
Ho Ryu; Bimal Pudasaini; Dasol Cho; Sungwoo Hong; Mu-Hyun Baik
Publication Date
2022-09
Journal
CHEMICAL SCIENCE, v.13, no.36, pp.10707 - 10714
Publisher
ROYAL SOC CHEMISTRY
Abstract
A typical synthetic protocol for preparing 7-azaindoles involves the coupling of 2-aminopyridine and alkyne substrates using a Rh(iii)-catalyst. The catalysis requires the assistance of an external Ag+ oxidant that is thought to regenerate the catalyst and increase the turnover efficiency. Density functional theory (DFT) simulations confirm that Ag+ can oxidize various neutral Rh(iii) intermediates encountered at different stages of the catalysis. Among them, the catalytically relevant species is a cationic Rh(iii)-pyridyl(+) complex (2A), which undergoes C-H activation of pyridine and couples an internal alkyne substrate into the pyridyl ligand to form the desired 7-azaindole product. Computations reveal that the oxidation also accelerates the reaction steps, including C-H activation via concerted metalation deprotonation (CMD), 1,2-alkyne insertion, and reductive elimination, thus highlighting the role of Ag+ as a catalytic promoter for the oxidatively induced reactivity of the Rh-catalyst in 7-azaindole synthesis. DFT calculations show that the catalysis is inefficient without invoking an oxidatively induced reaction pathway.
URI
https://pr.ibs.re.kr/handle/8788114/12353
DOI
10.1039/d2sc01650h
ISSN
2041-6520
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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