{"title":"Electrochemical Trifluoromethylation/Cyclization of N′-Arylidene-N-acryloyltosylhydrazides for the Synthesis of CF3-Substituted Pyrazolones","authors":"Yu Xia*, , , Wenlong Xu, , , Xinquan Wu, , , Tingting Yin, , , Shaofeng Wu, , , Ziren Chen, , , Bin Wang, , , Yonghong Zhang, , and , Chenjiang Liu*, ","doi":"10.1021/acs.joc.5c01197","DOIUrl":null,"url":null,"abstract":"<p >Herein, a mild and efficient synthesis of pyrazolones is disclosed through a sustainable electrochemical method. This electrolysis relied on cascade trifluoromethylation/cyclization by using CF<sub>3</sub>SO<sub>2</sub>Na as a trifluoromethyl source, which occurred directly at the anode. Two C–C bonds were formed to afford a series of novel trifluoromethyl-containing pyrazolone scaffolds without the addition of metals and redox reagents. Further mechanistic results showed that the reaction process may undergo a radical pathway.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 41","pages":"14429–14438"},"PeriodicalIF":3.6000,"publicationDate":"2025-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.joc.5c01197","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Herein, a mild and efficient synthesis of pyrazolones is disclosed through a sustainable electrochemical method. This electrolysis relied on cascade trifluoromethylation/cyclization by using CF3SO2Na as a trifluoromethyl source, which occurred directly at the anode. Two C–C bonds were formed to afford a series of novel trifluoromethyl-containing pyrazolone scaffolds without the addition of metals and redox reagents. Further mechanistic results showed that the reaction process may undergo a radical pathway.
期刊介绍:
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.