Continuous In Situ Electrogeneration of o-Benzoquinone in Microreactor: Application to High Yield Reaction with Benzenethiols
Continuous In Situ Electrogeneration of o-Benzoquinone in Microreactor: Application to High Yield Reaction with Benzenethiols
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DOI：
10.1556/jfc-d-12-00019
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发表时间：
2013-03-01
影响因子：
2.7
通讯作者：
Atobe, Mahito
中科院分区：
文献类型：
--
作者：
Kashiwagi, Tsuneo;Amemiya, Fumihiro;Atobe, Mahito
我们已经成功地证明了微流反应器在控制涉及不稳定邻苯二酚的反应中是非常有用的。以邻苯二酚电化学氧化生成的邻苯二酚与苯硫醇的Michael加成反应为模型反应。该反应体系能够使邻苯二酚选择性氧化，避免了苯硫酚的氧化，尽管这些氧化电位彼此接近。对几种反应条件的考察表明，该方法的主要特点是有效地生成邻苯二酚，并在微流控系统中快速用于后续反应而不分解。此外，循环伏安测试表明，邻苯二酚浓度和阳极材料的选择是影响邻苯二酚有效生成的关键因素。
We have successfully demonstrated that a microflow reactor is extremely useful in controlling reactions involving an unstable o-benzoquinone. As a model reaction, Michael addition reaction between o-benzoquinone generated from electrochemical oxidation of catechol and benzenethiols was employed. This reaction system enables selective oxidation of catechol avoiding the oxidation of benzenethiol, although these oxidation potentials are close to each other. The examination of several reaction conditions indicated that the key features of the method are an effective o-benzoquinone generation and its rapid use for the following reaction without decomposition in a microflow system. In addition, cyclic voltammetry measurements elucidated that catechol concentration and selection of anode material were crucial factors for effective o-quinone generation.