Synthesis of Novel 1,4-Substituted 1,2,3-Triazoles by Water-Soluble (Salicyladimine) 2Cu Complex Catalyzed Azide-Alkyne Cycloaddition in Water

Author(s): Yang Liu, Ping Liu*, Yan Liu, Yu Wei*

Journal Name: Letters in Organic Chemistry

Volume 14 , Issue 8 , 2017

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Abstract:

Background: 1,2,3-Triazoles represent an important structural motif frequently found in organic chemistry, biological science, medicinal chemistry, and material science. Thus, the synthesis of novel 1,2,3-triazoles derivatives by an efficient method has attracted considerable attention.

Methods: In this paper, we developed a simple and efficient azidation system of biphenyl tosylhydrazones with sodium azide. A series of new 4-(1-azidoethyl)-1,1'-biphenyl derivatives were prepared by the metalfree reductive reaction and further reacted with aryl acetylenes to afford novel 1,4-substituted 1,2,3- triazoles by water-soluble (salicyladimine)2Cu complex catalyzed azide-alkyne cycloaddition in water.

Results: The desired 1,4-substituted 1,2,3-triazoles were obtained in 27-94% yields in pure water without any organic solvent or phase transfer agents.

Conclusion: The catalytic system presented here enables the use of easily accessible starting materials and good functional group tolerance.

Keywords: 1, 2, 3-triazoles, (salicyladimine)2Cu complex, azide-alkyne cycloaddition, water, metal-free reductive reaction, functional group.

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Article Details

VOLUME: 14
ISSUE: 8
Year: 2017
Published on: 22 August, 2017
Page: [557 - 565]
Pages: 9
DOI: 10.2174/1570178614666170609072912
Price: $65

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