Organic Chemistry Portal

Abstracts

Search:

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

Weiguo Wang, Fang Wei, Yudao Ma*, Chen-Ho Tung and Zhenghu Xu*

*Key Lab for Colloid and Interface Chemistry of Education Ministry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, PR China, Email: ydmasdu.edu.cn, xuzhsdu.edu.cn

W. Wang, F. Wei, Y. Ma, C.-H. Tung, Z. Xu, Org. Lett., 2016, 18, 4158-4161.

DOI: 10.1021/acs.orglett.6b02199 (free Supporting Information)



see article for more reactions

Abstract

A copper(I)-catalyzed tandem CuAAC/alkynylation reaction of various alkynes, organic azides, and bromoalkynes provides rapid access to 5-alkynyl-1,2,3-triazoles via a copper-catalyzed alkyne azide cycloaddition followed by interception of the in situ formed cuprate-triazole intermediate with bromoalkyne under mild reaction conditions. Fully substituted triazoles can be isolated in high yields with complete regioselectivity.


see article for more examples



Key Words

click chemistry, 1,2,3-triazoles, multicomponent reactions


ID: J54-Y2016