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

doi:10.6023/cjoc201904058

摘要/Abstract

发展了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, 于温和的反应条件下以中等到良好的产率简便、高效地构建了一系列6H-菲啶类化合物. 机理研究表明, 反应的关键步骤经历了由Cu(0)/Selectfluor体系现场原位产生XCuOH (X=F, BF₄)物种, 进而诱导对C=N键的羟铜化反应和分子内C—H键胺化反应, 从而合成了6H-菲啶类化合物.

关键词: 铜催化, Selectfluor, 6H-菲啶, 环化反应, C—H键胺化

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

引用此文

郑立孟, 施冬冬, 鲍汉扬, 刘运奎. 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[J]. 有机化学, 2019, 39(10): 2821-2828.

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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