Selective Functionalization of Styrenes with Oxygen Using Different Electrode Materials: Olefin Cleavage and Synthesis of Tetrahydrofuran Derivatives
Selective Functionalization of Styrenes with Oxygen Using Different Electrode Materials: Olefin Cleavage and Synthesis of Tetrahydrofuran Derivatives
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DOI：
10.1002/anie.201809454
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发表时间：
2019-01-02
影响因子：
16.6
通讯作者：
Chiba, Kazuhiro
中科院分区：
文献类型：
--
作者：
Imada, Yasushi;Okada, Yohei;Chiba, Kazuhiro
电极材料可以对电解反应的过程具有显著影响。特别令人感兴趣的是，不同的电极可以从相同的基底产生不同的产物。报道了苯乙烯衍生物与分子氧的电极材料选择性转化。铂电极通过烯烃的裂解提供羰基产物，而碳电极实现四氢呋喃的形成。各种不同的苯乙烯可用于两种反应。电解允许直接和温和的化学转化，不含金属和氧化剂。电化学测量阐明了铂和碳电极对苯乙烯的不同影响。不同反应的关键可能是碳电极上的底物的氧化电位比铂电极上的低（更高的HOMO能量）。底物在碳电极上的吸附也可以促进四氢呋喃的形成。
Electrode materials can have a significant impact on the course of an electrolysis reaction. Of particular interest is that different electrodes can generate different products from the same substrate. The electrode-material-selective transformations of styrene derivatives with molecular oxygen are reported. Platinum electrodes afford carbonyl products via cleavage of olefins, whereas tetrahydrofuran formation is achieved with carbon electrodes. A variety of different styrenes are available for both reactions. Electrolysis allows straightforward and mild chemical conversions that are metal- and oxidant-free. Electrochemical measurements illuminate the different effects of platinum and carbon electrodes on styrenes. The key to the differing reactions is probably that the oxidation potentials of the substrates are lower (higher HOMO energy) on carbon electrodes than on platinum electrodes. The adsorption of the substrates on carbon electrodes can also promote tetrahydrofuran formation.