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DOI: https://doi.org/10.6023/cjoc202602022

研究论文

钯催化吲哚-3-羧酸酯和三亚甲基甲烷的环加成去芳构化反应

  • 张青霞 ,
  • 谢佳豪 ,
  • 顾庆 ,
  • 游书力
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  • 中国科学院上海有机化学研究所金属有机化学全国重点实验室 新基石实验室 上海 200032

收稿日期: 2026-02-27

  修回日期: 2026-03-21

  网络出版日期: 2026-04-17

基金资助

国家自然科学基金(No. 22393890、上海市科学技术委员会(23JC1404500)和上海市基础研究先行区计划资助项目.

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Pd-catalyzed [3+2] Cycloaddition/Dearomatization of Indole-3-carboxylates with Trimethylenemethane

  • Qing-Xia Zhang ,
  • Jia-Hao Xie ,
  • Qing Gu ,
  • Shu-Li You
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  • New Cornerstone Science Laboratory, State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Received date: 2026-02-27

  Revised date: 2026-03-21

  Online published: 2026-04-17

Supported by

NSFC (22393890), Science and Technology Commission of Shanghai Municipality (23JC1404500) and Shanghai Pilot Program for Basic Research. S.-L.Y. acknowledges the support from New Cornerstone Science Foundation.

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摘要

本文发展了钯催化吲哚-3-羧酸酯和三亚甲基甲烷（TMM）给体的[3+2]环加成反应。该反应经过钯催化的去芳构化过程,高效构建了一系列取代的2,3-环戊烷并吲哚啉（产率最高达99%）。在标准反应条件下,该反应对吲哚衍生物具有良好的官能团兼容性。值得注意的是,产物可进行酯水解、N-Ts基团脱除、Sonogashira偶联反应以及酯和卤素的还原等系列衍生化转化,充分证实了该合成方法的实用性和应用潜力。

关键词： 环加成; 去芳构化; 吲哚; 钯催化; 三亚甲基甲烷

本文引用格式

张青霞 , 谢佳豪 , 顾庆 , 游书力 . 钯催化吲哚-3-羧酸酯和三亚甲基甲烷的环加成去芳构化反应[J]. 有机化学, 0 : 202602022 -202602022 . DOI: 10.6023/cjoc202602022

Abstract

A formal [3+2] cycloaddition between indole-3-carboxylate derivatives and trimethylenemethane (TMM) donor is disclosed. The reaction proceeds smoothly in toluene at ambient conditions via a Pd-catalyzed dearomatization process, delivering a series of substituted 2,3-fused cyclopentannulated indolines (up to 99% yield). The reaction exhibits high functional group tolerance for indole derivatives under the standard conditions. Remarkably, the synthetic utility of this method was demonstrated by transformation of the products such as hydrolysis of ester, removal of Ts group, Sonogashira coupling reaction and reduction of ester and halogen.

Key words： cycloaddition; dearomatization; indole; palladium catalysis; trimethylenemethane

参考文献

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