Electrochemically Catalyzed N–N Coupling and Ring Cleavage Reaction of 1H-Pyrazoles

Abstract

The electrocatalyzed N–N coupling and ring cleavage reaction of 3-methyl-, 3,5-dimethyl-, 3-methyl-5-phenyl- and 3,5-diphenyl-1H-pyrazole was investigated and led to the electro-organic synthesis of new heterocyclic compounds. The results revealed that electrochemically produced 1H-pyrazole_ox plays the role of acceptor in a reaction with the starting molecule via a N–N coupling and ring cleavage reaction of pyrazoles. The proposed reaction sequence consists of anodic oxidation, dimerization, rearrangement and reduction. The electrochemically catalyzed reactions were accomplished under constant-current and constant-potential conditions using an undivided electrochemical cell with the advantages of mild reaction conditions, remarkable yields and environmental compatibility.

Key words

electrocatalysis - electrosynthesis - cyclic voltammetry - N–N coupling reaction - pyrazole ring cleavage

Publication History

Received: 29 April 2021

Accepted after revision: 10 June 2021

Article published online:
12 July 2021

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