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锰催化的烯丙醇与吲哚的交叉偶联反应:一条合成γ-羟基吲哚的精妙途径。

Manganese catalyzed cross-coupling of allylic alcohols and indoles: an elegant route for access to γ-hydroxyindole.

作者信息

Shen Yanyan, Hu Fangyuan, Chen Yuhua, Song Dingguo, Ling Fei, Zhong Weihui

机构信息

Zhejiang Institute of Economics and Trade Hangzhou 310018 P. R. China.

College of Pharmaceutical Sciences, Zhejiang University of Technology Hangzhou 310014 P. R. China

出版信息

RSC Adv. 2025 Aug 27;15(37):30622-30626. doi: 10.1039/d5ra04342e. eCollection 2025 Aug 22.

Abstract

Alcohol and indole derivatives are widely recognized as versatile building blocks in both chemical and biochemical synthesis. The formal conjugate addition between these two classes of compounds provides a powerful and sustainable strategy for constructing γ-hydroxyindoles, owing to the reaction's 100% atom economy and the ready availability of starting materials. In this study, we report a redox-neutral cross-coupling reaction between indoles and allylic alcohols, catalyzed by a manganese(i) pincer complex, which enables the efficient synthesis of a broad range of γ-hydroxyindoles under mild conditions. The reaction featured broad substrate scope with good functional tolerance under simple conditions (24 examples, 60-83% yields).

摘要

醇和吲哚衍生物在化学合成与生物化学合成中均被广泛视为通用的结构单元。这两类化合物之间的形式共轭加成反应为构建γ-羟基吲哚提供了一种强大且可持续的策略,这得益于该反应100%的原子经济性以及起始原料的易于获取。在本研究中,我们报道了一种由锰(I)钳形配合物催化的吲哚与烯丙醇之间的氧化还原中性交叉偶联反应,该反应能够在温和条件下高效合成多种γ-羟基吲哚。该反应具有广泛的底物范围,在简单条件下具有良好的官能团耐受性(24个实例,产率60 - 83%)。

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