Copper(I)‐Catalyzed Interrupted Click/Amidation: Regioselective Synthesis of 5‐Amide‐1,2,3‐triazoles
Weiguo Wang, Jingyu Wang, Yanqin Wang, Zhenghu Xu
Abstract
Comprehensive Summary 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.
Topics & Concepts
ChemistryRegioselectivityAmideCatalysisCopperClick chemistryCombinatorial chemistryOrganic chemistryClick Chemistry and ApplicationsChemical Synthesis and AnalysisFluorine in Organic Chemistry