C7-Indole Amidations and Alkenylations by Ruthenium(II) Catalysis.,Angewandte Chemie International Edition

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C7-Indole Amidations and Alkenylations by Ruthenium(II) Catalysis.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-06-02 , DOI: 10.1002/anie.202006164
Isaac Choi ₁ , Antonis M Messinis ₁ , Lutz Ackermann ₁

Affiliation

C7−H‐functionalized indoles are ubiquitous structural units of biological and pharmaceutical compounds for numerous antiviral agents against SARS‐CoV or HIV‐1. Thus, achieving site‐selective functionalizations of the C7−H position of indoles, while discriminating among other bonds, is in high demand. Herein, we disclose site‐selective C7−H activations of indoles by ruthenium(II) biscarboxylate catalysis under mild conditions. Base‐assisted internal electrophilic‐type substitution C−H ruthenation by weak O‐coordination enabled the C7−H functionalization of indoles and offered a broad scope, including C−N and C−C bond formation. The versatile ruthenium‐catalyzed C7−H activations were characterized by gram‐scale syntheses and the traceless removal of the directing group, thus providing easy access to pharmaceutically relevant scaffolds. Detailed mechanistic studies through spectroscopic and spectrometric analyses shed light on the unique nature of the robust ruthenium catalysis for the functionalization of the C7−H position of indoles.

中文翻译：

钌 (II) 催化下的 C7-吲哚酰胺化和烯基化。

C7-H-功能化吲哚是生物和药物化合物中普遍存在的结构单元，可用于多种针对 SARS-CoV 或 HIV-1 的抗病毒药物。因此，迫切需要实现吲哚 C7−H 位置的位点选择性功能化，同时区分其他键。在此，我们公开了在温和条件下通过二羧酸钌(II)催化对吲哚进行位点选择性C7-H活化。通过弱O配位的碱辅助内部亲电型取代C-H钌化使得吲哚的C7-H功能化，并提供了广泛的范围，包括C-N和C-C键的形成。多功能钌催化的 C7−H 活化的特点是克级合成和导向基团的无痕去除，从而可以轻松获得药物相关的支架。通过光谱和光谱分析进行的详细机理研究揭示了钌催化吲哚 C7−H 位置功能化的独特性质。

更新日期：2020-07-13

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