Issue 21, 2023

Transition-metal-free, oxidative C(sp3)–H arylation of amides with zeolite catalysts

Abstract

The oxidative coupling of amides and heteroarenes would allow for joining two of the most privileged scaffolds in medicinal chemistry. Here, we show that zeolite catalysts in combination with tert-butylperoxy ethylhexyl carbonate (TBEC) as oxidant can improve the formation of heterocoupled products. The exceptional selectivity and high yields are attributed to a pathway proceeding by a 2-electron oxidation of the amide to an N-acyliminium cation, followed by an electrophilic attack on the heterocycle.

Graphical abstract: Transition-metal-free, oxidative C(sp3)–H arylation of amides with zeolite catalysts

Supplementary files

Article information

Article type
Paper
Submitted
27 Jun 2023
Accepted
08 Sep 2023
First published
20 Sep 2023
This article is Open Access
Creative Commons BY-NC license

Catal. Sci. Technol., 2023,13, 6274-6280

Transition-metal-free, oxidative C(sp3)–H arylation of amides with zeolite catalysts

J. Vercammen, B. Krasniqi and D. De Vos, Catal. Sci. Technol., 2023, 13, 6274 DOI: 10.1039/D3CY00880K

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