CuI-Catalyzed, One-Pot, Three-Component Huisgen Cycloaddition Reaction of Conjugated Enynes and In Situ–Generated Azides

Abstract

A novel and efficient copper(I)-catalyzed three-component Huisgen cycloaddition reaction of conjugated enynes, alkyl halides, and sodium azide has been developed. These reactions were performed in the absence of amide ligands at room temperature, and the corresponding mono- and bis-1,2,3-triazoles were obtained in good to excellent yields in a one-pot procedure.

Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.

GRAPHICAL ABSTRACT

Keywords:

• Bis-triazoles
• click chemistry
• conjugated enynes
• Cu(I) catalysis
• triazoles

ACKNOWLEDGMENT

Financial support from the National Natural Sciences Foundation of China (21172032 and 20972026) is gratefully acknowledged.

Notes

^a Isolated yields.

^a Reaction conditions: 1 (1.0 mmol), 2 (1.0 mmol), NaN₃ (1.2 mmol), 3% CuI in DMSO/H₂O (8.0 mL; v/v, 1:1) at room temperature.

^b Isolated yields.

^a Reaction conditions: 1c (1.0 mmol), 2 (2.0 mmol), NaN₃ (2.2 mmol), 3% CuI in DMSO/H₂O (10.0 mL; v/v, 1:1) at room temperature.

^b Isolated yields.