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2021 , Vol. 41 >Issue 10: 4028 - 4038

DOI: https://doi.org/10.6023/cjoc202104057

研究论文

钴催化2-芳基吲哚氧化去芳构化及与烯酰胺[3+2]环化反应

  • 黄音君 ,
  • 李金山 ,
  • 李珅 ,
  • 马军安
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  • a 天津大学理学院化学系 天津市分子光电科学重点实验室 天津化学化工协同创新中心 天津 300072
    b 天津大学-新加坡国立大学福州联合学院 福州 350207

收稿日期: 2021-04-27

  修回日期: 2021-06-24

  网络出版日期: 2021-07-06

基金资助

国家自然科学基金(21772142); 国家自然科学基金(21961142015); 国家重点研发计划(2019YFA0905100)

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Cobalt-Catalyzed Aerobic Oxidative Dearomatization of 2-Aryl Indoles and in situ [3+2] Annulation with Enamides

  • Yinjun Huang ,
  • Jinshan Li ,
  • Shen Li ,
  • Junan Ma
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  • a Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Collaborative Innovation Center of Chemical Science & Engineering, Department of Chemistry, Tianjin University, Tianjin 300072
    b Joint School of National University of Singapore and Tianjin University, Fuzhou 350207
* Corresponding authors. E-mail: ;

Received date: 2021-04-27

  Revised date: 2021-06-24

  Online published: 2021-07-06

Supported by

National Natural Science Foundation of China(21772142); National Natural Science Foundation of China(21961142015); National Key Research & Development Program of China(2019YFA0905100)

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摘要

在氧气氛围中, 以2-芳基吲哚和N-乙酰基烯胺为原料, 实现了一锅法快速构建三环吲哚啉稠环骨架化合物. 该方法具有原料易得、操作简便、区域和非对映选择性较高以及环境友好等特点. 机理研究表明, 反应首先发生氧化去芳构化, 随后与烯酰胺进行[3+2]环化反应.

关键词： 钴催化; 氧化去芳构化; 环化反应; 吲哚; 烯酰胺

本文引用格式

黄音君 , 李金山 , 李珅 , 马军安 . 钴催化2-芳基吲哚氧化去芳构化及与烯酰胺[3+2]环化反应[J]. 有机化学, 2021 , 41(10) : 4028 -4038 . DOI: 10.6023/cjoc202104057

Abstract

An one-pot reaction for the rapid construction of tricyclic fused indoline frameworks from 2-aryl indoles and N-acetyl enamides under oxygen atmosphere has been developed. The notable features of this method involve easy availability of starting materials, simple manipulation, good regio- and diastereo-selectivity, as well as environmentally friendly conditions. Mechanistic studies indicated that this reaction proceeds via oxidative dearomatization and subsequent [3+2] annulation with enamides.

Key words： cobalt-catalysis; oxidative dearomatization; annulation; indoles; enamides

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