Synlett 2017; 28(04): 504-508
DOI: 10.1055/s-0036-1588086
letter
© Georg Thieme Verlag Stuttgart · New York

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
Further Information

Publication History

Received: 05 September 2016

Accepted after revision: 05 October 2016

Publication Date:
15 November 2016 (online)


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 SNAr 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.

Supporting Information