Issue 79, 2024

Carbene and photocatalyst-catalyzed 3-acylation of indoles for facile access to indole-3-yl aryl ketones

Abstract

3-Acyl indoles play important roles in both organic synthesis and diverse types of functional molecules. Herein, a facile nitrogen heterocyclic carbene (NHC) and photocatalyst cooperatively-catalyzed 3-acylation of indoles was disclosed. The reaction proceeded via radical cross-coupling of indole-based aryl radical cations with NHC-bound ketyl radical species, which are less explored in radical NHC catalysis. The reaction exhibits mild reaction conditions, broad substrate scope, and good functional group tolerance. Mechanistic studies support our proposed reaction pathway. The synthesis of structurally diverse analogs of an aldose reductase inhibitor and antibacterial activity investigation further demonstrated the utility of the current acylation reaction.

Graphical abstract: Carbene and photocatalyst-catalyzed 3-acylation of indoles for facile access to indole-3-yl aryl ketones

Supplementary files

Article information

Article type
Communication
Submitted
02 Шіл. 2024
Accepted
04 Қыр. 2024
First published
06 Қыр. 2024

Chem. Commun., 2024,60, 11088-11091

Carbene and photocatalyst-catalyzed 3-acylation of indoles for facile access to indole-3-yl aryl ketones

T. Tu, G. Nie, T. Zhang, C. Hu, S. Ren, H. Xia and Y. R. Chi, Chem. Commun., 2024, 60, 11088 DOI: 10.1039/D4CC03257H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements