Copper-Catalyzed Double C–N Bond Formation for the Synthesis of Diverse Benzimidazoles from N-Alkyl-2-iodoaniline and Sodium Azide

Zhengkai Chen; Hongli Li; Gangjian Cao; Jianfeng Xu; Maozhong Miao; Hongjun Ren

doi:10.1055/s-0036-1588086

Synlett, Table of Contents

Synlett 2017; 28(04): 504-508
DOI: 10.1055/s-0036-1588086

letter

Copper-Catalyzed Double C–N Bond Formation for the Synthesis of Diverse Benzimidazoles from N-Alkyl-2-iodoaniline and Sodium Azide

Zhengkai Chen*

Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. of China Email: zkchen@zstu.edu.cn Email: renhj@zstu.edu.cn

,

Hongli Li

Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. of China Email: zkchen@zstu.edu.cn Email: renhj@zstu.edu.cn

,

Gangjian Cao

Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. of China Email: zkchen@zstu.edu.cn Email: renhj@zstu.edu.cn

,

Jianfeng Xu

Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. of China Email: zkchen@zstu.edu.cn Email: renhj@zstu.edu.cn

,

Maozhong Miao

Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. of China Email: zkchen@zstu.edu.cn Email: renhj@zstu.edu.cn

,

Hongjun Ren*

Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. of China Email: zkchen@zstu.edu.cn Email: renhj@zstu.edu.cn

› Author Affiliations

Abstract

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Abstract

An efficient approach to the synthesis of benzimidazole derivatives has been achieved by copper-catalyzed double C–N bonds formation of N-alkyl-2-iodoaniline and sodium azide. The reaction was supposed to proceed through copper-catalyzed tandem reaction of S_NAr reaction, aerobic oxidation of C(sp³)–H bond and intramolecular C–N bond formation sequence. Structurally diverse 2-aryl, alkenyl and alkyl benzoimidazole derivatives were assembled by this methodology.

Key words

copper catalyst - C–N bond formation - benzimidazoles - tandem reaction - N-heterocyclic compounds

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References

References and Notes

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