Citation: 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 shu

Synthesis of Carbazolequinones by Pd-Catalyzed Double Arylation Process

Li Xue ^a,b,† ,
Song Zirui ^a,† ,
Chen Xin ^a,b ,
Cai Yichao ^a ,
Liu Yajie ^a ,
Chen Chunxia ^a,b,, ,
Peng Jinsong ^a,,

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

Corresponding author: Chen Chunxia, ccx0109@nefu.edu.cn Peng Jinsong, jspeng1998@nefu.edu.cn
Received Date: 28 September 2019
Revised Date: 28 November 2019
Available Online: 25 April 2020
Fund Project: Project supported by the Fundamental Research Funds for the Central Universities (No. 2572017AB25) and the National Innovation Experiment Program for University Students (No. 201810225098)the National Innovation Experiment Program for University Students 201810225098the Fundamental Research Funds for the Central Universities 2572017AB25

Figures(4)

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.
- palladium-catalyzed,
- carbazolequinones,
- amination,
- arylation,
- tandem reaction
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