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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 4: 950 - 958

DOI: https://doi.org/10.6023/cjoc201909040

Synthesis of Carbazolequinones by Pd-Catalyzed Double Arylation Process

  • Li Xue ,
  • Song Zirui ,
  • Chen Xin ,
  • Cai Yichao ,
  • Liu Yajie ,
  • Chen Chunxia ,
  • Peng Jinsong
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  • 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 date: 2019-09-28

  Revised date: 2019-11-28

  Online 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).

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Abstract

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

Cite this article

Li Xue , Song Zirui , Chen Xin , Cai Yichao , Liu Yajie , Chen Chunxia , Peng Jinsong . Synthesis of Carbazolequinones by Pd-Catalyzed Double Arylation Process[J]. Chinese Journal of Organic Chemistry, 2020 , 40(4) : 950 -958 . DOI: 10.6023/cjoc201909040

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