Electrochemical synthesis of biaryls via CH/CH homocoupling of methoxyarenes

IF 4.1 3区化学 Q1 CHEMISTRY, ANALYTICAL

Journal of Electroanalytical Chemistry Pub Date : 2024-10-28 DOI:10.1016/j.jelechem.2024.118739

Babak Kaboudin , Sepideh Sadighi , Fahimeh Varmaghani , Leila Behrouzi

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.

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通过甲氧基烯烃的 CH/CH 同偶联反应电化学合成双芳基化合物

在过渡金属和无氧化剂条件下，研究人员在非分裂电池中研究了通过甲氧基烯烃的同偶联反应直接和一锅电合成双甲氧基噻吩的方法。对电极、电解质和溶剂等各种参数的影响进行了研究和评估。为了深入了解反应的机理，对甲氧基烯烃进行了循环伏安（CV）研究，并提出了一种自由基途径。反应开始时，苯甲醚被阳极氧化成苯甲酰基阳离子自由基，然后与另一个苯甲醚反应，形成新的双苯甲酰基阳离子自由基。形成的中间体发生氢抽取反应，然后阳极氧化生成联苯甲酰阳离子，通过抽取第二个氢得到联苯甲醚。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Electroanalytical Chemistry 化学-电化学

CiteScore

7.80

自引率

6.70%

发文量

912

审稿时长

2.4 months

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.