Electrochemically controlled dearomative 2,3-difunctionalization of indoles to synthesize oxoindoline derivatives,Organic Chemistry Frontiers

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Electrochemically controlled dearomative 2,3-difunctionalization of indoles to synthesize oxoindoline derivatives
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2022-05-23 , DOI: 10.1039/d2qo00670g
Xichao Peng ₁ , Linzi Wen ₁ , Zuozhou Ning ₁ , Zhicheng Zhang ₁ , Chengbo Sun ₁ , Yu Tang ₁ , Pengju Feng ₁

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A general and practical protocol for an electrochemically controlled dearomative 2,3-difunctionalization of indoles via electrochemical anode-selective oxidative cross-coupling has been demonstrated. The reaction runs under metal-, oxidant- and catalyst-free conditions, allowing tunable access to a wide variety of synthetically useful oxindole derivatives, such as 3,3-diaryl-2-oxindole, 3-hydroxy-2-oxindole and 2-hydroxy-3-oxindole derivatives. Finally, a preliminary mechanistic study indicated that the indole radical cation could undergo two different pathways via switching the anode materials under the same reaction conditions to deliver various products.

中文翻译：

吲哚的电化学控制去芳烃 2,3-双官能化合成氧代二氢吲哚衍生物

已经证明了通过电化学阳极选择性氧化交叉偶联对吲哚进行电化学控制的去芳烃 2,3-双官能化的通用和实用方案。该反应在无金属、无氧化剂和无催化剂的条件下进行，可调节获得多种合成有用的羟吲哚衍生物，例如 3,3-二芳基-2-羟吲哚、3-羟基-2-羟吲哚和 2-羟基-3-羟吲哚衍生物。最后，初步机理研究表明，吲哚自由基阳离子可以通过在相同反应条件下切换负极材料，通过两种不同的途径产生不同的产物。

更新日期：2022-05-23

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