{"title":"Electrochemical synthesis of biaryls via CH/CH homocoupling of methoxyarenes","authors":"Babak Kaboudin , Sepideh Sadighi , Fahimeh Varmaghani , Leila Behrouzi","doi":"10.1016/j.jelechem.2024.118739","DOIUrl":null,"url":null,"abstract":"<div><div>A direct and one-pot electrosynthesis method for the regioselective synthesis of bis methoxybiarenes <em>via</em> homocoupling of methoxyarenes has been studied in undivided cells in the transition-metal and oxidant-free conditions. The effect of various parameters, such as electrodes, electrolytes, and solvents has been studied and evaluated. To gain detailed mechanistic insight into the reaction, cyclic voltammetric (CV) studies of methoxyarenes were performed, and a radical pathway has been suggested. The reaction begins with an anodic oxidation of anisole to an anisyl cation radical followed by reaction with another anisole may form a new bisanisyl cation radical. The formed intermediate undergoes a hydrogen abstraction, followed by anodic oxidation gave bisanisyl cation and the bisanisole was obtained by abstraction of second hydrogen.</div></div>","PeriodicalId":355,"journal":{"name":"Journal of Electroanalytical Chemistry","volume":"974 ","pages":"Article 118739"},"PeriodicalIF":4.1000,"publicationDate":"2024-10-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Electroanalytical Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S1572665724007173","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ANALYTICAL","Score":null,"Total":0}
引用次数: 0
Abstract
A direct and one-pot electrosynthesis method for the regioselective synthesis of bis methoxybiarenes via homocoupling of methoxyarenes has been studied in undivided cells in the transition-metal and oxidant-free conditions. The effect of various parameters, such as electrodes, electrolytes, and solvents has been studied and evaluated. To gain detailed mechanistic insight into the reaction, cyclic voltammetric (CV) studies of methoxyarenes were performed, and a radical pathway has been suggested. The reaction begins with an anodic oxidation of anisole to an anisyl cation radical followed by reaction with another anisole may form a new bisanisyl cation radical. The formed intermediate undergoes a hydrogen abstraction, followed by anodic oxidation gave bisanisyl cation and the bisanisole was obtained by abstraction of second hydrogen.
期刊介绍：
The Journal of Electroanalytical Chemistry is the foremost international journal devoted to the interdisciplinary subject of electrochemistry in all its aspects, theoretical as well as applied.
Electrochemistry is a wide ranging area that is in a state of continuous evolution. Rather than compiling a long list of topics covered by the Journal, the editors would like to draw particular attention to the key issues of novelty, topicality and quality. Papers should present new and interesting electrochemical science in a way that is accessible to the reader. The presentation and discussion should be at a level that is consistent with the international status of the Journal. Reports describing the application of well-established techniques to problems that are essentially technical will not be accepted. Similarly, papers that report observations but fail to provide adequate interpretation will be rejected by the Editors. Papers dealing with technical electrochemistry should be submitted to other specialist journals unless the authors can show that their work provides substantially new insights into electrochemical processes.
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