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Cu-Enabled [3 + 2] Annulation of In Situ Formed Nitrile Ylides with Aryldiazonium Salts: Access to 5-Cyano-1,2,4-Triazoles

Lu-Nan Zhou, Fang-Fang Feng, Chi Wai Cheung* and Jun-An Ma*

*Tianjin Collaborative Innovation Centre of Chemical Science & Engineering, Tianjin University, Tianjin 300072, P. R. of China, Email: zhiwei.zhangtju.edu.cn, majun_an68tju.edu.cn

L.-N. Zhou, F.-F. Feng, C. W. Cheung, J.-A. Ma, Org. Lett., 2021, 23, 739-744.

DOI: 10.1021/acs.orglett.0c03960 (free Supporting Information)


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Abstract

A three-component reaction of readily available 2-diazoacetonitriles, nitriles, and aryldiazonium salts provides a wide range of 1-aryl 5-cyano-1,2,4-triazoles. This regiospecific synthesis relies on a dipolar [3 + 2] annulation of an in situ formed nitrile ylide with the aryldiazonium salt.

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proposed mechanism



Key Words

1,2,4-triazoles, multicomponent reactions, 1,3-dipolar cycloaddition


ID: J54-Y2021