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2022 , Vol. 42 >Issue 11: 3816 - 3823

DOI: https://doi.org/10.6023/cjoc202205039

研究论文

铑催化的邻苯二甲酸酐与环状2-重氮-1,3-二酮和甲醇的串联C—H活化/跨环偶联/环化反应合成酯基官能化的并环异香豆素类化合物的研究

  • 商铭洲 ,
  • 张兰兰 ,
  • 陈淼淼 ,
  • 胡汪成 ,
  • 何心伟 ,
  • 陆红健
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  • a南京大学化学化工学院 南京 210093
    b安徽师范大学化学与材料科学学院 安徽芜湖 241002

收稿日期: 2022-05-22

  修回日期: 2022-07-03

  网络出版日期: 2022-07-14

基金资助

国家自然科学基金(21772001); 国家自然科学基金(22071100); 大学生创新创业训练计划(202110370035)

收起

Synthesis of Esterified/Fused Isocoumarins via Rh-Catalyzed C—H Activation/Transannulative Coupling/Annulation of Phthalic Anhydrides with Cyclic 2-Diazo-1,3-diketones and Methanol

  • Mingzhou Shang ,
  • Lanlan Zhang ,
  • Miaomiao Chen ,
  • Wangcheng Hu ,
  • Xinwei He ,
  • Hongjian Lu
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  • aSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093
    bCollege of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000
*E-mail:

Received date: 2022-05-22

  Revised date: 2022-07-03

  Online published: 2022-07-14

Supported by

National Natural Science Foundation of China(21772001); National Natural Science Foundation of China(22071100); National Undergraduate Training Program for Innovation and Entrepreneurship(202110370035)

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摘要

报道了一种铑(III)催化的基于邻苯二价酸酐与环状2-重氮-1,3-二酮和甲醇的串联反应构建酯基官能化环己烯酮并异香豆素衍生物的方法. 该反应经由C—H键活化、跨环偶联及随后的环化反应实现一个C—C键和两个C—O键的构筑. 该反应体系中无需加入任何添加剂或碱, 并能在空气氛围下很好地进行, 且具有良好的官能团容忍性和底物普适性.

关键词： 环化反应; C—H键活化; 重氮化合物; 异香豆素; 邻苯二甲酸酐

本文引用格式

商铭洲 , 张兰兰 , 陈淼淼 , 胡汪成 , 何心伟 , 陆红健 . 铑催化的邻苯二甲酸酐与环状2-重氮-1,3-二酮和甲醇的串联C—H活化/跨环偶联/环化反应合成酯基官能化的并环异香豆素类化合物的研究[J]. 有机化学, 2022 , 42(11) : 3816 -3823 . DOI: 10.6023/cjoc202205039

Abstract

A rhodium(III)-catalyzed cascade reaction of phthalic anhydrides with cyclic 2-diazo-1,3-diketones and methanol for modular access to esterified cyclohexenone-fused isocoumarins has been developed. This strategy involves the process of one C—C and two C—O bonds formation through C—H activation, transannulative coupling and subsequent annulation process. Furthermore, no additive and base are needed in this transformation, and interestingly, the reaction could proceed well under air atmosphere with broad substrate and good functional groups tolerance.

Key words： annulation; C—H activation; diazo compound; isocoumarin; phthalic anhydride

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