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Generation of aryl radicals by redox processes. Recent progress in the arylation methodology
Russian Chemical Reviews ( IF 7.0 ) Pub Date : 2021-02-02 , DOI: 10.1070/rcr4959
Dmitry Ivanovich Bugaenko , A A Volkov , Alexander Vakhtangovich Karchava , Marina Abramovna Yurovskaya

Arylation methods based on the generation and use of aryl radicals have been a rapidly growing field of research in recent years and currently represent a powerful strategy for carbon – carbon and carbon – heteroatom bond formation. The progress in this field is related to advances in the methods for generation of aryl radicals. The currently used aryl radical precursors include aryl halides, aryldiazonium and diaryliodonium salts, arylcarboxylic acids and their derivatives, arylboronic acids, arylhydrazines, organosulfur(II, VI) compounds and some other compounds. Aryl radicals are generated under mild conditions by single electron reduction or oxidation of precursors induced by conventional reagents, visible light or electric current. A crucial role in the development of the radical arylation methodology belongs to photoredox processes either catalyzed by transition metal complexes or organic dyes or proceeding without catalysts. Unlike the conventional transition metal-catalyzed arylation methods, radical arylation reactions proceed very often at room temperature and have high functional group tolerance. Without claiming to be exhaustive, this review covers the most important advances of the current decade in the generation and synthetic applications of (het)aryl radicals. Examples of reactions are given and mechanistic insights are highlighted.

The bibliography includes 341 references.



中文翻译:

通过氧化还原过程产生芳基自由基。芳基化方法的最新进展

近年来,基于芳基自由基的产生和使用的芳基化方法已成为一个快速发展的研究领域,目前代表了碳-碳和碳-杂原子键形成的强大策略。该领域的进展与芳基自由基生成方法的进步有关。目前使用的芳基自由基前体包括芳基卤化物、芳基重氮盐和二芳基碘盐、芳基羧酸及其衍生物、芳基硼酸、芳基肼、有机硫(II,VI)化合物和一些其他化合物。芳基自由基是在温和条件下通过常规试剂、可见光或电流诱导的前体的单电子还原或氧化产生的。自由基芳基化方法发展中的一个关键作用属于光氧化还原过程,要么由过渡金属配合物或有机染料催化,要么在没有催化剂的情况下进行。与传统的过渡金属催化的芳基化方法不同,自由基芳基化反应经常在室温下进行,并且具有很高的官能团耐受性。在不要求详尽无遗的情况下,本综述涵盖了当前十年在(杂)芳基自由基的产生和合成应用方面最重要的进展。给出了反应的例子,并强调了机械方面的见解。自由基芳基化反应经常在室温下进行,并且具有很高的官能团耐受性。在不要求详尽无遗的情况下,本综述涵盖了当前十年在(杂)芳基自由基的产生和合成应用方面最重要的进展。给出了反应的例子,并强调了机械方面的见解。自由基芳基化反应经常在室温下进行,并且具有很高的官能团耐受性。在不要求详尽无遗的情况下,本综述涵盖了当前十年在(杂)芳基自由基的产生和合成应用方面最重要的进展。给出了反应的例子,并强调了机械方面的见解。

参考书目包括 341 篇参考文献。

更新日期:2021-02-02
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