Synthesis of Carbazolequinones by Pd-Catalyzed Double Arylation Process

doi:10.6023/cjoc201909040

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

钯催化双芳基化反应合成咔唑醌衍生物的研究

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

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 E-mail:ccx0109@nefu.edu.cn;jspeng1998@nefu.edu.cn
基金资助:
中央高校基本科研业务费专项资金（No.2572017AB25）和大学生创新训练（No.201810225098）资助项目.

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

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).

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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.

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钯催化双芳基化反应合成咔唑醌衍生物的研究

Synthesis of Carbazolequinones by Pd-Catalyzed Double Arylation Process

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