Issue 10, 2023

Sustainable synthesis of azobenzenes, quinolines and quinoxalines via oxidative dehydrogenative couplings catalysed by reusable transition metal oxide–Bi(iii) cooperative catalysts

Abstract

Oxidative dehydrogenative coupling (ODC) is a useful tool for the formation of new C–C, C–O and N[double bond, length as m-dash]N bonds in an atom-economic and sustainable manner. Although this strategy is versatile, it is much less introduced to prepare N-heterocycles. Herein, we report the oxidative dehydrogenative coupling of anilines and 2-aminoanilies with vicinal diols to selectively produce azobenzenes (34–95% yield), quinolines (65–100% yield) and quinoxalines (78–100% yield) utilizing an environmentally friendly synthesis strategy. The reactions were catalysed by cooperative bifunctional catalysts based on transition metal oxides/Bi(III) which allow solvent-, additive-, oxidant- and base-free cyclisations/couplings. In addition, the catalysts were proven to be highly robust and reusable.

Graphical abstract: Sustainable synthesis of azobenzenes, quinolines and quinoxalines via oxidative dehydrogenative couplings catalysed by reusable transition metal oxide–Bi(iii) cooperative catalysts

Supplementary files

Article information

Article type
Paper
Submitted
08 3 2023
Accepted
23 3 2023
First published
20 4 2023
This article is Open Access
Creative Commons BY license

Catal. Sci. Technol., 2023,13, 3069-3083

Sustainable synthesis of azobenzenes, quinolines and quinoxalines via oxidative dehydrogenative couplings catalysed by reusable transition metal oxide–Bi(III) cooperative catalysts

M. Kocsis, K. Baán, S. B. Ötvös, Á. Kukovecz, Z. Kónya, P. Sipos, I. Pálinkó and G. Varga, Catal. Sci. Technol., 2023, 13, 3069 DOI: 10.1039/D3CY00327B

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