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 jul 2024
Accepted
04 sep 2024
First published
06 sep 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

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