Cell Voltage-Dependent Structural Dichotomy: Electrochemical C-H Acyloxylation and N-Acylation of 2 H-Indazoles

Org Lett. 2023 Jul 28;25(29):5421-5425. doi: 10.1021/acs.orglett.3c01649. Epub 2023 Jul 14.

Abstract

A simple and efficient electrochemical method that utilizes modulation of the cell voltage to cause structural alterations in 2H-indazole is introduced. This method enables the C-3 acyloxylation of 2H-indazole and promotes the transfer of the acyl group from C-3 to N-1, allowing the N-acylation of 2H-indazoles. Additionally, the application of the μ-electro flow reactor was demonstrated, showcasing its effectiveness in achieving gram-scale production of 3x within a short residence time.