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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. 2018

Jian-Quan Liu, and Xuanyu Shen, and Yihan Wang, and Xiang-Shan Wang, and Xihe Bi
School of Chemistry and Materials Science , Jiangsu Key Laboratory of Green Synthesis for Functional Materials Jiangsu Normal University , Xuzhou , Jiangsu 221116 , China.

An unprecedented catalyst-dependent regioselective [3 + 2] cycloaddition of isocyanides with aryl diazonium salts is reported. 1,3-Disubstituted 1,2,4-triazoles were selectively obtained in high yield under Ag(I) catalysis, whereas 1,5-disubstituted 1,2,4-triazoles were formed by Cu(II) catalysis. These catalytic methodologies provide a controlled, modular, and facile access to 1,2,4-triazole scaffolds with high efficiency, broad substrate scope, and excellent functional group compatibility.

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