Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2821-2828.DOI: 10.6023/cjoc201904058 Previous Articles     Next Articles



郑立孟, 施冬冬, 鲍汉扬, 刘运奎*()   

  1. 浙江工业大学化学工程学院 绿色化学与技术国家重点实验室培育基地 杭州 310014
  • 收稿日期:2019-04-24 修回日期:2019-05-26 发布日期:2019-06-12
  • 通讯作者: 刘运奎
  • 基金资助:

Copper(0)/Selectfluor System-Catalyzed Tandem Annulation/Aromatization of o-Aryl Benzenesulfonylimides:A Facile Synthesis of 6H-Phenanthridines

Zheng Limeng, Shi Dongdong, Bao Hanyang, Liu Yunkui*()   

  1. State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, College of Chemical Engineering,Zhejiang University of Technology, Hangzhou 310014
  • Received:2019-04-24 Revised:2019-05-26 Published:2019-06-12
  • Contact: Liu Yunkui
  • Supported by:
    Project supported by the National Natural Science Foundation of China(21772176);Project supported by the National Natural Science Foundation of China(21372201);The Opening Foundation of Zhejiang Key Course of Chemical Engineering and Technology, Zhejiang University of Technology

A facile and efficient method for the synthesis of 6H-phenanthridines has been successfully developed involving a copper(0)/Selectfluor system-catalyzed tandem annulation/aromatization of o-aryl benzenesulfonylimides. A variety of substituted 6H-phenanthridines were synthesized in moderate to good yields under mild reaction conditions. Mechanistic experiments revealed that the reaction might involve an oxycupration of C=N bond followed by an intramolecular C—H bond amination as the key steps triggered by an in situ generated copper species XCuOH (X=F or BF4) from the Cu(0)/Selectfluor system.

Key words: copper catalysis, Selectfluor, 6H-phenanthridine, annulation reaction, C—H bond amination