Copper(I)-Catalyzed Interrupted Click/Amidation: Regioselective Synthesis of 5-Amide-1,2,3-triazoles

Weiguo Wang; Jingyu Wang; Yanqin Wang; Zhenghu Xu

doi:10.1002/cjoc.70232

Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (23) :3221 -3226. DOI: 10.1002/cjoc.70232

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Copper(I)-Catalyzed Interrupted Click/Amidation: Regioselective Synthesis of 5-Amide-1,2,3-triazoles

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Abstract

A copper-catalyzed tandem click/amidation reaction involving various alkynes, azides, and dioxazolones has been developed for the synthesis of fully substituted 5-amide-1,2,3-triazoles. The key step in this reaction is the interception of the in situ-formed cuprate-triazole intermediate with N-acyl nitrenes, which are generated from dioxazolones. The choice of precursor for the N-acyl nitrenes plays a crucial role in the success of the reaction. This method is characterized by a broad substrate scope, mild reaction conditions, and complete regioselectivity.

Keywords

Click reaction / Amidation / Triazoles / Complete regioselectivity / Nitrenes / Dioxazolones / Azides / Copper / Cycloaddition

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Weiguo Wang, Jingyu Wang, Yanqin Wang, Zhenghu Xu. Copper(I)-Catalyzed Interrupted Click/Amidation: Regioselective Synthesis of 5-Amide-1,2,3-triazoles. Chinese Journal of Chemistry, 2025, 43(23): 3221-3226 DOI:10.1002/cjoc.70232