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有机化学
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有机化学 ›› 2024, Vol. 44 ›› Issue (11): 3505-3517.DOI: 10.6023/cjoc202405016 上一篇    下一篇

研究论文

Rh(III)催化烯烃与重氮化物氨基烷基化反应构筑异吲哚啉酮

刘玉英†,a,b,c,d, 符展维†,a,b,c,d, 杨超d, 罗木鹏d,*(), 班树荣a,b,c,*(), 王守国d,*()   

  1. a 山西医科大学药学院 太原 030001
    b 山西医科大学 慢性肾脏病教育部医药基础研究创新中心 太原 030001
    c 山西医科大学 药物合成与制剂新技术山西省重点实验室 太原 030001
    d 中国科学院深圳先进技术研究院 深圳 518055
  • 收稿日期:2024-05-13 修回日期:2024-05-22 发布日期:2024-05-30
  • 作者简介:
    †共同第一作者
  • 基金资助:
    山西省自然科学基金(202303021221131); 山西省特色药物研制工程研究中心和深圳市科技创新委员会(JCYJ20210324101810028); 山西省特色药物研制工程研究中心和深圳市科技创新委员会(JCYJ-20220818101601004); 山西省特色药物研制工程研究中心和深圳市科技创新委员会(JCYJ20220818095801004)

Rh(III)-Catalyzed Aminoalkylation of Alkenes with Diazo Compounds toward Functionalized Isoindolinones

Yuying Liu†,a,b,c,d, Zhanwei Fu†,a,b,c,d, Chao Yangd, Mupeng Luod,*(), Shurong Bana,b,c,*(), Shouguo Wangd,*()   

  1. a School of Pharmacy, Shanxi Medical University, Taiyuan 030001
    b Medicinal Basic Research Innovation Center of Chronic Kidney Disease, Ministry of Education, Shanxi Medical University, Taiyuan 030001
    c Shanxi Provincial Key Laboratory of Drug Synthesis and Novel Pharmaceutical Preparation Technology, Shanxi Medical University, Taiyuan 030001
    d Shenzhen Institute of Advanced Technology, Chinese Academy of Sciences, Shenzhen 518055
  • Received:2024-05-13 Revised:2024-05-22 Published:2024-05-30
  • Contact: *E-mail:shouguo.wang@siat.ac.cn;shurongban@sxmu.edu.cn;mp.luo@siat.ac.cn
  • About author:
    †These authors contributed equally to this work.
  • Supported by:
    Natural Science Foundation of Shanxi Province(202303021221131); Project of Shanxi Engineering Research Center of Characteristic Drug Development, and the Shenzhen Science and Technology Innovation Committee(JCYJ20210324101810028); Project of Shanxi Engineering Research Center of Characteristic Drug Development, and the Shenzhen Science and Technology Innovation Committee(JCYJ-20220818101601004); Project of Shanxi Engineering Research Center of Characteristic Drug Development, and the Shenzhen Science and Technology Innovation Committee(JCYJ20220818095801004)

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报道了[Cp*RhCl2]2催化的烯烃与重氮化合物的氨基烷基化串联环化反应, 实现了一系列3,3-双取代异吲哚啉酮的高效、快速构建. 该反应具有反应条件温和、反应选择性好以及底物适用范围广等优点, 为一系列具有应用价值的异吲哚啉酮骨架化合物的合成提供了一种原子经济性方法.

关键词: 氨基烷基化反应, 环化反应, 异吲哚啉酮, 铑(III)催化, 重氮化合物

A [Cp*RhCl2]2-catalyzed intramolecular annulation reaction via aminoalkylation of alkenes with diazo compounds has been developed to construct highly-functionalized isoindolinones. This approach exhibits step economy, mild reaction conditions, and good functional group tolerance, facilitating access to a wide range of highly-valuable functionalized isoindolinones with high level of yields (up to 99% yield).

Key words: aminoalkylation reaction, annulation reaction, isoindolinone, Rh(Ⅲ)-catalysis, diazo compounds