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2025 , Vol. 45 >Issue 4: 1342 - 1351

DOI: https://doi.org/10.6023/cjoc202407029

研究论文

钯催化多米诺Heck/分子间偶联反应合成3-烷基取代茚衍生物

  • 姚团利 ,
  • 王琳琳 ,
  • 李涛
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  • 陕西科技大学化学与化工学院 西安 710021

收稿日期: 2024-07-15

  修回日期: 2024-08-30

  网络出版日期: 2024-10-11

基金资助

国家重点研发计划(2023YFD1802603)

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Palladium-Catalyzed Domino Heck/Intermolecular Cross Coupling Reaction for the Synthesis of 3-Alkyl Substituted Indene Derivatives

  • Tuanli Yao ,
  • Linlin Wang ,
  • Tao Li
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  • College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi'an 710021
* E-mail:

Received date: 2024-07-15

  Revised date: 2024-08-30

  Online published: 2024-10-11

Supported by

National Key Research and Development Program(2023YFD1802603)

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摘要

茚衍生物是多种天然产物及药物的核心骨架之一, 在医药、材料等领域具有广泛的应用前景. 开发简单、高效地合成茚衍生物的方法具有重要意义. 本工作以邻位链接非活化烯烃的碘苯为原料, 在钯催化下经分子内Heck反应生成烷基钯(II)中间体, 该中间体诱导2-(2-苯乙炔基)苯基丙二酸二乙酯发生分子内亲核环化, 合成了多种3-烷基取代茚衍生物. 该方法具有条件温和、操作简单、产率高、底物适用性广等优点, 为合成茚衍生物提供了一种新策略.

关键词： 钯催化; 茚衍生物; Heck反应

本文引用格式

姚团利 , 王琳琳 , 李涛 . 钯催化多米诺Heck/分子间偶联反应合成3-烷基取代茚衍生物[J]. 有机化学, 2025 , 45(4) : 1342 -1351 . DOI: 10.6023/cjoc202407029

Abstract

Indene derivatives are one of the core skeletons of many natural products and drugs, and are widely used in medicine, materials and other fields. It is of great significance to develop a simple and efficient method for the synthesis of indene derivatives. In this work, iodobenzenes with proximity linking unactivated olefins undergo palladium-catalyzed intramolecular Heck reaction to generate alkylpalladium(II) intermediates, which induce the intramolecular nucleophilic cyclization of 2-(2-phenylethynyl)phenylmalonate diethyl ester to afford a series of 3-alkyl substituted indene derivatives. The reaction has the advantages of mild conditions, simple operation, high yield and wide applicability of substrates, which provides a new strategy for the synthesis of indene derivatives.

Key words： palladium catalysis; indene derivatives; Heck reaction

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