Synthesis of 3-nitroindoles by sequential paired electrolysis

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.

Automated summary

A new method for synthesizing 3-nitroindoles was reported in this study, which involves electrochemical cyclisation of nitroenamines in the presence of potassium iodide. Control experiments and cyclic voltammogram studies revealed a sequential paired electrolysis process leading to the formation of 3-nitroindoles.