Electrochemical synthesis of <i>N</i>,<i>N</i>′-disubstituted indazolin-3-ones <i>via</i> an intramolecular anodic dehydrogenative N–N coupling reaction

Abstract

'-disubstituted indazolin-3-ones by an intramolecular anodic dehydrogenative N-N coupling reaction. This method is characterized by mild reaction conditions, an easy experimental setup, excellent scalability, and a high atom economy. It was used to synthesize various indazolin-3-one derivatives in yields up to 78%, applying inexpensive and sustainable electrode materials and a low supporting electrolyte concentration. Mechanistic studies, based on cyclic voltammetry experiments, revealed a biradical pathway. Furthermore, the access to single 2-aryl substituted indazolin-3-ones by cleavage of the protecting group could be demonstrated.

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