Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55128, Mainz, Germany.
Max Planck Graduate Center, Mainz, Germany.
Angew Chem Int Ed Engl. 2017 Nov 13;56(46):14727-14731. doi: 10.1002/anie.201708946. Epub 2017 Oct 20.
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] pincer-type ligands.
首次实现了噻吩与酚类化合物的电化学脱氢 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可以得到两类具有重要意义的化合物。电化学 C-H 活化交叉偶联反应的范围扩大到了硫杂环化合物。以前，只能转化各种苯并芳体系，而电化学 C-H 活化交叉偶联反应中杂环的应用并不成功。在这里，无需试剂和金属的反应条件提供了一种可持续的电化学途径，为基于噻吩和酚类化合物的各种双芳基和三芳基产物提供了一种有吸引力的合成方法。该方法在未分隔的电池中易于进行，可规模化，并具有内在的安全性。所得产物可用于电子材料或作为 [OSO] 夹持型配体。
