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Copper-Catalyzed Oxidative Cross-Dehydrogenative Coupling/Oxidative Cycloaddition: Synthesis of 4-Acyl-1,2,3-Triazoles

Yi Liu, Gang Nie, Zhongzhen Zhou*, Lihui Jia and Yunfeng Chen*

*School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430073, China, Email: yfchenwit.edu.cn, zhouzzsmu.edu.cn

Y. Liu, G. Nie, Z. Zhou, L. Jia, Y. Chen, J. Org. Chem., 2017, 82, 9198-9203.

DOI: 10.1021/acs.joc.7b01429 (free Supporting Information)



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Abstract

A copper-catalyzed three-component reaction of methyl ketones, organic azides, and DMF as one-carbon (C1) donor provides 4-acyl-1,2,3-triazoles in good yields. The transformation proceeds via an oxidative C-H/C-H cross-dehydrogenative coupling followed by an oxidative 1,3-dipolar cycloaddition.


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proposed mechanism



Key Words

1,2,3-triazoles, multicomponent reactions, potassium peroxydisulfate


ID: J42-Y2017