{"title":"Electrochemical Bromination of Arenes in a 200% Cell.","authors":"Sara Torabi,Mahdi Jamshidi,Gerhard Hilt","doi":"10.1021/acs.joc.4c01086","DOIUrl":null,"url":null,"abstract":"Herein, we describe the investigation of electrochemical bromination of electron-rich arenes in a 200% cell. For this application, at first, the influence of an excess of supporting electrolyte (Bu4NBr) on chemical bromination was investigated. The application of >4.0 equiv of Bu4NBr proved to enhance the regioselectivity of the bromination process for O- and N-substituted arenes considerably. The linear paired electrolysis was then optimized upon these insights, and a number of electron-rich arenes could be brominated in high yields with excellent regioselectivity. The use of O2 as a sacrificial starting material in combination with 2-ethylanthraquinone as a catalyst leads to the enhanced formation of H2O2 at the cathode, resulting in current efficiencies >150% for a considerable number of examples.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c01086","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, we describe the investigation of electrochemical bromination of electron-rich arenes in a 200% cell. For this application, at first, the influence of an excess of supporting electrolyte (Bu4NBr) on chemical bromination was investigated. The application of >4.0 equiv of Bu4NBr proved to enhance the regioselectivity of the bromination process for O- and N-substituted arenes considerably. The linear paired electrolysis was then optimized upon these insights, and a number of electron-rich arenes could be brominated in high yields with excellent regioselectivity. The use of O2 as a sacrificial starting material in combination with 2-ethylanthraquinone as a catalyst leads to the enhanced formation of H2O2 at the cathode, resulting in current efficiencies >150% for a considerable number of examples.
期刊介绍:
The 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.