Copper(I)-Catalyzed Three-Component Click/Alkynylation: One-Pot Synthesis of 5-Alkynyl-1,2,3-triazoles

• DOI: 10.1021/acs.orglett.6b02199
• Publication Date: 2016-08-23T10:29:27Z
• Authors: Weiguo Wang; Fang Wei; Yudao Ma; Chen-Ho Tung; Zhenghu Xu
• Keywords: 01 natural sciences; 0104 chemical sciences

A copper(I)-catalyzed tandem CuAAC/alkynylation reaction of various alkynes, organic azides, and bromoalkynes to provide rapid access to 5-alkynyl-1,2,3-triazoles has been developed. The reaction proceeded via a copper-catalyzed alkyne azide cycloaddition followed by interception of the in situ formed cuprate-triazole intermediate with bromoalkyne. This reaction offers a new method to afford fully substituted triazoles in high yields with complete regioselectivity under mild reaction conditions.