有机化学 ›› 2022, Vol. 42 ›› Issue (7): 2222-2228.DOI: 10.6023/cjoc202201030 上一篇    下一篇

研究论文

1,3-二氢-3-亚烷基-吲哚-2-酮的膦催化合成研究

李婧婕, 王宇豪, 孟甜甜, 黄毅勇*()   

  1. 武汉理工大学化学化工与生命科学学院 武汉 430070
  • 收稿日期:2022-01-19 修回日期:2022-03-16 发布日期:2022-08-09
  • 通讯作者: 黄毅勇
  • 基金资助:
    国家自然科学基金(21772151); 国家自然科学基金(22072111)

Phosphine-Catalyzed Synthesis of 1,3-Dihydro-3-alkylidene-2H-indol-2-ones

Jingjie Li, Yuhao Wang, Tiantian Meng, Yiyong Huang()   

  1. School of Chemistry, Chemical Engineering and Life Sciences, Wuhan University of Technology, Wuhan 430070
  • Received:2022-01-19 Revised:2022-03-16 Published:2022-08-09
  • Contact: Yiyong Huang
  • Supported by:
    National Natural Science Foundation of China(21772151); National Natural Science Foundation of China(22072111)

报道了一类三(4-甲氧基苯基)膦催化联烯酰亚胺与吲哚-2-酮之间的迈克尔加成/双键移位串联反应. 该反应条件温和, 操作简单, 产物收率较高, 具有较好的底物适应性和化学选择性, 为1,3-二氢-3-亚烷基-吲哚-2-酮骨架的构建提供了一种有效的新方法, 最后, 还提出了可能的反应历程.

关键词: 吲哚-2-酮, 联烯, 膦催化, 迈克尔加成反应, 双键移位

A P(4-OMe-C6H4)3-catalyzed Michael addition/double bond migration tandem reaction between allenyl imide and indol-2-ones was developed. This synthetic strategy for diverse 1,3-dihydro-3-alkylidene-2H-indol-2-ones features operationally simple, good substrate scope, high chemoselectivity and mild reaction conditions. The proposed reaction mechanism is also provided.

Key words: indol-2-one, allene, phosphine catalysis, Michael addition, double bond migration