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

doi:10.6023/cjoc201904058

Abstract

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

Cite this article

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.

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Cu(0)/Selectfluor体系催化的邻芳基磺酰亚胺的串联环化/芳构化反应：一种简便合成6H-菲啶的方法