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Copper-Catalyzed Oxidative C(sp3)-H Functionalization for Facile Synthesis of 1,2,4-Triazoles and 1,3,5-Triazines from Amidines

Huawen Huang, Wei Guo, Wanqing Wu*, Chao-Jun Li and Huanfeng Jiang*

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

H. Huang, W. Guo, W. Wu, C.-J. Li, H. Jiang, Org. Lett., 2015, 17, 2894-2897.

DOI: 10.1021/acs.orglett.5b00995 (free Supporting Information)


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Abstract

A facile and versatile catalytic system involving copper catalyst, K3PO4 as the base, and O2 as the oxidant enables an efficient synthesis of 2,4,6-trisubstituted and 2,6-disubstituted 1,3,5-triazines and 1,3-disubstituted 1,2,4-triazoles from amidines with trialkylamines, DMSO, and DMF as the reaction partners, respectively. This protocol features an inexpensive catalyst, a green oxidant, good functional group tolerance, and high regioselectivity.

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Key Words

1,2,4-triazoles, oxygen


ID: J54-Y2015