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Issue 32, 2019
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Oxidative amidation of benzaldehyde using a quinone/DMSO system as the oxidizing agent

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Abstract

An efficient transition-metal-based heterogeneous catalyst free procedure for obtaining the oxidative amidation of benzaldehyde using quinones as oxidizing agents in low molar proportions is described here. Pyrrolylquinones (PQ) proved to be more suitable than DDQ and 2,5-dimethylbenzoquinone to conduct the oxidation process. Although the solvent itself acted as the oxidant with low to moderate yields, PQ/DMSO provided an efficient system for carrying out the reaction under operational simplicity, mild reaction conditions, short reaction times and high yields of the desired product. The scope of the method was evaluated with substituted benzaldehydes and secondary amines. Theoretical foundations are given to explain the participation of quinones as an oxidizing agent in the reaction.

Graphical abstract: Oxidative amidation of benzaldehyde using a quinone/DMSO system as the oxidizing agent

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Supplementary files

Article information


Submitted
17 Apr 2019
Accepted
03 Jun 2019
First published
10 Jun 2019

This article is Open Access

RSC Adv., 2019,9, 18265-18270
Article type
Paper

Oxidative amidation of benzaldehyde using a quinone/DMSO system as the oxidizing agent

I. Mejía-Farfán, M. Solís-Hernández, P. Navarro-Santos, C. A. Contreras-Celedón, C. J. Cortés-García and L. Chacón-García, RSC Adv., 2019, 9, 18265
DOI: 10.1039/C9RA02893E

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