Issue 27, 2022

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

Abstract

The use of electricity as a traceless oxidant enables a sustainable and novel approach to N,N′-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.

Graphical abstract: Electrochemical synthesis of N,N′-disubstituted indazolin-3-ones via an intramolecular anodic dehydrogenative N–N coupling reaction

Supplementary files

Article information

Article type
Edge Article
Submitted
30 Mar 2022
Accepted
10 Jun 2022
First published
13 Jun 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022,13, 8180-8186

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

J. C. Bieniek, M. Grünewald, J. Winter, D. Schollmeyer and S. R. Waldvogel, Chem. Sci., 2022, 13, 8180 DOI: 10.1039/D2SC01827F

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