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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.

DOI:10.1039/d5ra04342e
PMID:40895735
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12394842/
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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本文引用的文献

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Efficient Synthesis of C3-Alkylated and Alkenylated Indoles via Manganese-Catalyzed Dehydrogenation.锰催化脱氢法高效合成 C3-烷基化和烯基化吲哚
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Manganese-Catalyzed Regioselective Dehydrogenative C- versus N-Alkylation Enabled by a Solvent Switch: Experiment and Computation.通过溶剂转换实现的锰催化区域选择性脱氢C-与N-烷基化:实验与计算
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Iridium-Catalyzed α-Methylation of α-Aryl Esters Using Methanol as the C1 Source.铱催化的 α-芳基酯的 α-甲基化反应,使用甲醇作为 C1 源。
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Direct Conversion of Alcohols into Alkenes by Dehydrogenative Coupling with Hydrazine/Hydrazone Catalyzed by Manganese.锰催化肼/腙脱氢偶联实现醇向烯烃的直接转化
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