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Electrochemical Synthesis of 3,5-Disubstituted Pyrazoles from Ynone Hydrazones via Diselenide-Catalyzed Cyclization Strategy

Zhouting ZengCollege of Chemistry and Chemical EngineeringFeng ZhaoHunan Provincial Key Laboratory for Synthetic Biology of Traditional Chinese Medicine, School of Pharmaceutical SciencesHuimei ZhongCollege of Chemistry and Chemical EngineeringZi YangChangsha Medical UniversityHuaixin WeiSuzhou University of Science and TechnologyShan JiCollege of Chemistry and Chemical EngineeringMingming YuSchool of Chemistry and Chemical EngineeringJinhui CaiCollege of Chemistry and Chemical Engineering
2025en
ABI

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Given the existing limitations of traditional methods for the synthesis of pyrazole derivatives, developing new, mild, and efficient approach toward pyrazole skeletons is necessary. Herein, we report an electrochemically driven diselenide-catalyzed cyclization of 1,3-disubstituted prop-2-yn-1-one hydrazones that realize the rapid synthesis of 3,5-disubstituted pyrazoles under metal-free, oxidant-free, and base-free conditions. The practical utility of this method is underscored by its wide substrate scope, high tolerance toward various functional groups, high efficiency, mild conditions, gram-scale synthesis, and diverse derivatizations. Furthermore, the preliminary mechanistic experiments indicate that this reaction possibly proceeds via a cationic pathway.

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