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Switchable Reactivity between Vinyl Azides and Terminal Alkyne by Nano Copper Catalysis

Jinghe Cen, Yaodan Wu, Jianxiao Li, Liangbin Huang, Wanqing Wu, Zhongzhi Zhu, Shaorong Yang*, Huanfeng Jiang*

*School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China, Email: lisryangscut.edu.cn, jianghfscut.edu.cn

J. Cen, Y. Wu, J. Li, L. Huang, W. Wu, Z. Zhu, S. Yang, H. Jiang, Org. Lett., 2019, 21, 2090-2094.

DOI: 10.1021/acs.orglett.9b00373 (free Supporting Information)



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Abstract

A nano copper-catalyzed reaction of vinyl azides with terminal alkynes provides 2,5-disubstituted pyrroles in high yield with aryl alkynes and aliphatic alkynes, whereas 2,3,4-trisubstituted pyrroles were formed with silylated alkynes. The reactions offer high efficiency, excellent regioselectivity, and good functional group compatibility.


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Key Words

pyrroles


ID: J54-Y2019