Issue 20, 2023

Electrochemical C3 acyloxylation reactions of 2H-indazoles with carboxylic acids via C(sp2)–O coupling

Abstract

A green and practical electrooxidation protocol for C3 acyloxylation of 2H-indazoles with carboxylic acids in the presence of potassium carbonate has been developed by intermolecular cross-dehydrogenative C(sp2)–O coupling. It is sustainable without the use of transition-metal catalysts, stoichiometric oxidants, and even extra supporting electrolytes. Potassium carbonate plays a key role in the reaction, and reacts with carboxylic acids to form carboxylates. Mechanistic studies by cyclic voltammetry and control experiments reveal that the reaction proceeds via an ECE mechanism. In addition, various carboxylic acids and 2H-indazoles are suitable in this system and provide a series of novel desired products at room temperature in an undivided cell.

Graphical abstract: Electrochemical C3 acyloxylation reactions of 2H-indazoles with carboxylic acids via C(sp2)–O coupling

Supplementary files

Article information

Article type
Paper
Submitted
18 Jun 2023
Accepted
22 Aug 2023
First published
29 Aug 2023

Green Chem., 2023,25, 8117-8123

Electrochemical C3 acyloxylation reactions of 2H-indazoles with carboxylic acids via C(sp2)–O coupling

X. Liu, Y. Hu, Y. She, M. Li and Z. Shen, Green Chem., 2023, 25, 8117 DOI: 10.1039/D3GC02175K

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