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[3 + 2] Cycloaddition of Isocyanides with Aryl Diazonium Salts: Catalyst-Dependent Regioselective Synthesis of 1,3- and 1,5-Disubstituted 1,2,4-Triazoles

Jian-Quan Liu, Xuanyu Shen, Yihan Wang, Xiang-Shan Wang*, Xihe Bi*

*School of Chemistry and Mat. Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116; Department of Chemistry, Northeast Normal University, Changchun 130024, China, Email: xswang1974yahoo.com, bixh507nenu.edu.cn

J.-Q. Liu, X. Shen, Y. Wang, X.-S. Wang, X. Bi, Org. Lett., 2018, 20, 6930-6933.

DOI: 10.1021/acs.orglett.8b03069


Abstract

1,5-Disubstituted 1,2,4-triazoles were formed by Cu(II) catalysis in high yield, whereas 1,3-disubstituted 1,2,4-triazoles were selectively obtained under Ag(I) catalysis. These regioselective catalytic methodologies provide a facile access to 1,2,4-triazole scaffolds with high efficiency, broad substrate scope, and excellent functional group compatibility.

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Key Words

1,2,4-Triazoles


ID: J54-Y2018