Organic semiconductor photocatalyst can bifunctionalize arenes and heteroarenes
Organic semiconductor photocatalyst can bifunctionalize arenes and heteroarenes
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DOI：
10.1126/science.aaw3254
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发表时间：
2019-07-26
期刊：
影响因子：
56.9
通讯作者：
Koenig, Burkhard
中科院分区：
文献类型：
--
作者：
Ghosh, Indrajit;Khamrai, Jagadish;Koenig, Burkhard
半导体表面上的光激发电子-空穴对可以与两种不同的基底进行氧化还原反应。与常规电合成类似，主要氧化还原中间体仅提供单独的氧化产物和还原产物，或者更罕见地，联合收割机组合成一种加成产物。在这里，我们报告说，一个稳定的有机半导体材料，介孔石墨氮化碳（mpg-CN），可以作为一个可见光的光氧化还原催化剂，协调氧化和还原界面电子转移到两个不同的基板在两个或三个组件系统的芳烃和杂芳烃的直接双重碳氢官能化。mpg-CN催化剂耐受反应性自由基和强亲核试剂，通过反应混合物的简单离心可直接回收，并且可重复用于具有保守活性的至少四种催化转化。
Photoexcited electron-hole pairs on a semiconductor surface can engage in redox reactions with two different substrates. Similar to conventional electrosynthesis, the primary redox intermediates afford only separate oxidized and reduced products or, more rarely, combine to one addition product. Here, we report that a stable organic semiconductor material, mesoporous graphitic carbon nitride (mpg-CN), can act as a visible-light photoredox catalyst to orchestrate oxidative and reductive interfacial electron transfers to two different substrates in a two-or three-component system for direct twofold carbon-hydrogen functionalization of arenes and heteroarenes. The mpg-CN catalyst tolerates reactive radicals and strong nucleophiles, is straightforwardly recoverable by simple centrifugation of reaction mixtures, and is reusable for at least four catalytic transformations with conserved activity.