Issue 11, 2021

Chemoselective electrochemical reduction of nitroarenes with gaseous ammonia

Abstract

Valuable aromatic nitrogen compounds can be synthesized by reduction of nitroarenes. Herein, we report electrochemical reduction of nitroarenes by a protocol that uses inert graphite felt as electrodes and ammonia as a reductant. Depending on the cell voltage and the solvent, the protocol can be used to obtain aromatic azoxy, azo, and hydrazo compounds, as well as aniline derivatives with high chemoselectivities. The protocol can be readily scaled up to >10 g with no decrease in yield, demonstrating its potential synthetic utility. A stepwise cathodic reduction pathway was proposed to account for the generations of products in turn.

Graphical abstract: Chemoselective electrochemical reduction of nitroarenes with gaseous ammonia

Supplementary files

Article information

Article type
Paper
Submitted
14 Qun 2021
Accepted
23 Nah 2021
First published
23 Nah 2021

Org. Biomol. Chem., 2021,19, 2468-2472

Chemoselective electrochemical reduction of nitroarenes with gaseous ammonia

L. Chang, J. Li, N. Wu and X. Cheng, Org. Biomol. Chem., 2021, 19, 2468 DOI: 10.1039/D1OB00077B

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