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Synthesis of 1H-indazoles by an electrochemical radical Csp2–H/N–H cyclization of arylhydrazones†
Hao Wan,Dongting Li,Huadan Xia,Liwen Yang,Hesham Alhumade,Hong Yi
Chemical Communications Pub Date : 12/04/2021 00:00:00 , DOI:10.1039/D1CC04656J
Abstract

The development of efficient and sustainable C–N bond-forming reactions to N-heterocyclic frameworks has been a long-standing interest in organic synthesis. In this work, we develop an electrochemical radical Csp2–H/N–H cyclization of arylhydrazones to 1H-indazoles. The electrochemical anodic oxidation approach was adopted to synthesize a variety of 1H-indazole derivatives in moderate to good yields. HFIP was not only employed as a solvent or the proton donor, but also can promote the formation of N free radicals. This synthetic methodology is operationally simple, and less expensive electrodes would be suitable for this chemistry.

Graphical abstract: Synthesis of 1H-indazoles by an electrochemical radical Csp2–H/N–H cyclization of arylhydrazones
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