Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (8): 2008-2016.DOI: 10.6023/cjoc201804007 Previous Articles     Next Articles



刘宏, 董慧茹, 安锐, 唐渝, 许开天, 张渊明   

  1. 暨南大学化学与材料学院化学系 广州 510632
  • 收稿日期:2018-04-04 修回日期:2018-05-02 发布日期:2018-05-17
  • 通讯作者: 唐渝, 张渊明;
  • 基金资助:


Synthesis of 1,3-Diaryl or Dialkyl-2H-isoindole-4,7-dione via Barbier-Grignard-Type Reaction

Liu Hong, Dong Huiru, An Rui, Tang Yu, Xu Kaitian, Zhang Yuanming   

  1. Department of Chemistry, College of Chemistry and Materials Science, Jinan University, Guangzhou 510632
  • Received:2018-04-04 Revised:2018-05-02 Published:2018-05-17
  • Contact: 10.6023/cjoc201804007;
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21274083) and the National University Student Innovation and Entrepreneurship Training Program of China (No. 82617055).

A novel, convenient and efficient protocol to N-heterocyclic derivatives of 1,3-diaryl or diaklyl-2H-isoin-dole-4,7-dione has been developed via the Barbier-Grignard-type reaction. Good to excellent yields up to 96% have been achieved by performing the reaction in one pot using Ta2O5 as the catalyst. The protocol displays good tolerance to different aryl and alkyl bromides. Based on some experimental results, a plausible mechanism involving nucleophilic addition and electron transfer has been proposed. The quinone structure in 1,3-diphenyl-2H-isoindole-4,7-dione (3a) makes it coupling with amine to form more complicated structure.

Key words: isoindole, Barbier-Grignard reaction, Ta2O5, oxidative coupling