Citation: Zheng Limeng, Shi Dongdong, Bao Hanyang, Liu Yunkui. Copper(0)/Selectfluor System-Catalyzed Tandem Annulation/ Aromatization of o-Aryl Benzenesulfonylimides: A Facile Synthesis of 6H-Phenanthridines[J]. Chinese Journal of Organic Chemistry, ;2019, 39(10): 2821-2828. doi: 10.6023/cjoc201904058 shu

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

State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Corresponding author: Liu Yunkui, ykuiliu@zjut.edu.cn
Received Date: 24 April 2019
Revised Date: 26 May 2019
Available Online: 12 October 2019
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21772176, 21372201), the Opening Foundation of Zhejiang Key Course of Chemical Engineering and Technology, Zhejiang University of Technologythe National Natural Science Foundation of China 21772176the National Natural Science Foundation of China 21372201

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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.
- copper catalysis,
- Selectfluor,
- 6H-phenanthridine,
- annulation reaction,
- C-H bond amination
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