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

Abstract

A ruthenium(II)-catalyzed regioselective direct diamidation of 3-carbonylindoles at the C4- and C5- position 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 diamidation 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.

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Article information


Submitted
16 Apr 2021
Accepted
20 Jul 2021
First published
21 Jul 2021

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2021, Accepted Manuscript
Article type
Edge Article

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

S. Devkota, S. Kim, S. Y. Yoo, S. Mohandoss, M. Baik and Y. R. Lee, Chem. Sci., 2021, Accepted Manuscript , DOI: 10.1039/D1SC02138A

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