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Ruthenium(ii)-catalyzed regioselective direct C4-and C5-diamidation of indoles and mechanistic studies

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Title
Ruthenium(ii)-catalyzed regioselective direct C4-and C5-diamidation of indoles and mechanistic studies
Author(s)
Devkota, Shreedhar; Suyeon Kim; Seok Yeol Yoo; Mohandoss, Sonaimuthu; Mu-Hyun Baik; Lee, Yong Rok
Publication Date
2021-09-14
Journal
CHEMICAL SCIENCE, v.12, no.34, pp.11427 - 11437
Publisher
ROYAL SOC CHEMISTRY
Abstract
A ruthenium(ii)-catalyzed regioselective direct diamidation of 3-carbonylindoles at the C4- and C5-positions using various dioxazolones is described. This novel protocol allows for the effective installation of two amide groups on the benzene ring in indole. A remarkably broad substrate scope, excellent functional group tolerance, and mild reaction conditions are notable features of this protocol. Further explorations reveal that benzo[b]thiophene-3-carboxaldehyde is a viable substrate and affords its corresponding diamidation products. The diamido indoles are further converted into various functionalized products and used as sensors for metal ion detection. Density functional theory studies are also conducted to propose a reaction mechanism and provide a detailed understanding of the regioselectivity observed in the reaction.
URI
https://pr.ibs.re.kr/handle/8788114/10274
DOI
10.1039/d1sc02138a
ISSN
2041-6520
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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