Site-selective C–H functionalization to access the arene backbone of indoles and quinolines,Chemical Society Reviews

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Site-selective C–H functionalization to access the arene backbone of indoles and quinolines
Chemical Society Reviews ( IF 40.4 ) Pub Date : 2021-09-06 , DOI: 10.1039/d0cs00334d
B Prabagar ₁ , Youqing Yang ₁ , Zhuangzhi Shi ₁

Affiliation

The site-selective C–H bond functionalization of heteroarenes can eventually provide chemists with great techniques for editing and building complex molecular scaffolds. During the past decade, benzo-fused N-heterocycles such as indoles and quinolines have been among the most widely investigated organic templates. Early developments have led to site-selective C–H bond functionalization on the pyrrole and pyridine cores of indoles and quinolines; however, C–H functionalization on the benzenoid ring has remained a great challenge in catalysis. In this review, we elaborate on recent developments in the highly challenging functionalization of C–H bonds on the less-reactive benzenoid core of indoles and quinolines. These findings are mainly described as selective directing group assisted strategies, remote C–H functionalization techniques and their reaction mechanisms. The underlying principle in each strategy is elucidated, which aims to facilitate the design of a more advanced structure of heterocycles based on bioactive molecules, synthetic drugs, and material aspects. Moreover, the challenges and perspectives for catalytic C–H functionalization to access the arene backbone of indoles and quinolines are also proposed in the conclusion section.

中文翻译：

位点选择性 C-H 功能化以访问吲哚和喹啉的芳烃骨架

杂芳烃的位点选择性 C-H 键功能化最终可以为化学家提供用于编辑和构建复杂分子支架的伟大技术。在过去的十年中，苯并稠合的 N-杂环如吲哚和喹啉一直是研究最广泛的有机模板。早期的发展导致吲哚和喹啉的吡咯和吡啶核上的位点选择性 C-H 键功能化；然而，苯环上的 C-H 官能化仍然是催化中的一个巨大挑战。在这篇综述中，我们详细阐述了在吲哚和喹啉的反应性较低的苯类核心上的 C-H 键功能化方面的最新进展。这些发现主要被描述为选择性指导小组辅助策略，远程 C-H 功能化技术及其反应机制。阐明了每个策略的基本原理，旨在促进基于生物活性分子、合成药物和材料方面的更先进的杂环结构的设计。此外，结论部分还提出了催化 C-H 官能化以获取吲哚和喹啉的芳烃骨架的挑战和前景。

更新日期：2021-09-06

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