Single and Twofold Metal- and Reagent-Free Anodic C-C Cross-Coupling of Phenols with Thiophenes.
Single and Twofold Metal- and Reagent-Free Anodic C-C Cross-Coupling of Phenols with Thiophenes.
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DOI：
10.1002/anie.201708946
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发表时间：
2017-11
影响因子：
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通讯作者：
A. Wiebe;S. Lips;D. Schollmeyer;R. Franke;S. Waldvogel
中科院分区：
文献类型：
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作者：
A. Wiebe;S. Lips;D. Schollmeyer;R. Franke;S. Waldvogel
首次实现了噻吩与苯酚的电化学还原C-C交叉偶联反应。这种可持续且非常简单的阳极偶联反应使得能够获得两类重要化合物。电化学碳氢活化交叉偶联反应的范围扩大到硫杂环。以前，只有各种苯并芳香族体系可以被转化，而杂环化合物的应用在电化学C-H活化交叉偶联反应中并不成功。在这里，无试剂和无金属的反应条件提供了一个可持续的电化学途径，提供了一个有吸引力的合成方法，以各种各样的双和三元产物的基础上噻吩和苯酚。该方法易于在未分隔的单元中进行，可扩展，并且本质上是安全的。所得产物可用于电子材料或作为[OSO]2-钳型配体。
The first electrochemical dehydrogenative C-C cross-coupling of thiophenes with phenols has been realized. This sustainable and very simple to perform anodic coupling reaction enables access to two classes of compounds of significant interest. The scope for electrochemical C-H-activating cross-coupling reactions was expanded to sulfur heterocycles. Previously, only various benzoid aromatic systems could be converted, while the application of heterocycles was not successful in the electrochemical C-H-activating cross-coupling reaction. Here, reagent- and metal-free reaction conditions offer a sustainable electrochemical pathway that provides an attractive synthetic method to a broad variety of bi- and terarylic products based on thiophenes and phenols. This method is easy to conduct in an undivided cell, is scalable, and is inherently safe. The resulting products offer applications in electronic materials or as [OSO]2- pincer-type ligands.