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: ydma
sdu.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
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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.
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Key Words
click chemistry, 1,2,3-triazoles, multicomponent reactions
ID: J54-Y2016
