Issue 36, 2021

Synthesis of 3-nitroindoles by sequential paired electrolysis

Abstract

3-Nitroindoles are synthetically versatile intermediates but current methods for the preparation hinder their widespread application. Herein, we report that nitroenamines undergo electrochemical cyclisation to 3-nitroindoles in the presence of potassium iodide. Detailed control experiments and cyclic voltammogram studies infer the reaction proceeds via a sequential paired electrolysis process, beginning with anodic oxidation of iodide (I) to the iodine radical (I˙), which facilitates cyclisation of the nitroenamine to give a 3-nitroindolinyl radical. Cathodic reduction and protonation generates a 3-nitroindoline that upon oxidation forms the 3-nitroindole.

Graphical abstract: Synthesis of 3-nitroindoles by sequential paired electrolysis

Supplementary files

Article information

Article type
Paper
Submitted
25 Jul 2021
Accepted
24 Aug 2021
First published
24 Aug 2021

Org. Biomol. Chem., 2021,19, 7903-7913

Synthesis of 3-nitroindoles by sequential paired electrolysis

A. C. Lindsay, P. A. Kilmartin and J. Sperry, Org. Biomol. Chem., 2021, 19, 7903 DOI: 10.1039/D1OB01453F

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