Harnessing the Reactivity of Nitroarene Radical Anions to Create Quinoline N-oxides by Electrochemical Reductive Cyclization

21 August 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Electrochemical reduction of 2-allyl-substituted nitroarenes using a simple, undivided electrochemical cell with non-precious electrodes to generate nitroarene radical anions was developed. The reactivity of ArNO2 radical anion can be controlled to participate in 1,5-HAT reactions to construct quinoline N-oxides bearing aryl-, heteroaryl-, alkenyl-, benzyl-, sulfonyl-, or carboxyl groups.

Keywords

electrosynthesis
N-heterocycles
single electron reduction

Supplementary materials

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Supporting Information
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Experimental procedures, spectroscopic and analytical data
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