Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (4): 950-958.DOI: 10.6023/cjoc201909040 Previous Articles     Next Articles


李雪a,b, 宋子锐a, 陈鑫a,b, 蔡轶超a, 刘雅婕a, 陈春霞a,b, 彭进松a   

  1. a 东北林业大学 化学化工与资源利用学院 哈尔滨 150040;
    b 东北林业大学 材料科学与工程学院 哈尔滨 150040
  • 收稿日期:2019-09-28 修回日期:2019-11-28 发布日期:2019-12-19
  • 通讯作者: 陈春霞, 彭进松;
  • 基金资助:

Synthesis of Carbazolequinones by Pd-Catalyzed Double Arylation Process

Li Xuea,b, Song Ziruia, Chen Xina,b, Cai Yichaoa, Liu Yajiea, Chen Chunxiaa,b, Peng Jinsonga   

  1. a College of Chemistry, Chemical Engineering and Resource Utilization, Northeast Forestry University, Harbin 150040;
    b Material Science and Engineering College, Northeast Forestry University, Harbin 150040
  • Received:2019-09-28 Revised:2019-11-28 Published:2019-12-19
  • Supported by:
    Received September 28, 2019; revised November 28, 2019; published online December 19, 2019. Project supported by the Fundamental Research Funds for the Central Universities (No. 2572017AB25) and the National Innovation Experiment Program for University Students (No. 201810225098).

Starting from 2-aminonaphthalene-1,4-dione and o-dibromoarene, palladium-catalyzed one-pot synthesis of carbazolequinone was examined in detail. With PdCl2 as the catalyst, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (Xphos) as ligand and K2CO3 as base in N,N-dimethylformamide (DMF) at 160℃ for 72 h, the annulation reaction afforded the corresponding product by N-H/C-H double arylation process in 81% yield. With different o-dihaloarenes, a series of carbazolequinone derivatives were synthesized to examine the scope and limitation of the above method, and the structure of products was characterized by 1H NMR and 13C NMR spectra.

Key words: palladium-catalyzed, carbazolequinones, amination, arylation, tandem reaction