Acid-Base Jointly Promoted Copper(I)-Catalyzed Azide-Alkyne Cycloaddition

Changwei Shao, Xinyan Wang*, Qun Zhang, Sheng Luo, Jichen Zhao and Yuefei Hu*

*Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China, Email: wangxinyanmail.tsinghua.edu.cn, yfhmail.tsinghua.edu.cn

C. Shao, X. Wang, Q. Zhang, S. Luo, J. Zhao, Y. Hu, J. Org. Chem., 2011, 76, 6832-6836.

DOI: 10.1021/jo200869a

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Abstract

CuI/DIPEA/HOAc is a highly efficient catalytic system for CuAAC. In this novel acid-base jointly promoted formation of 1,2,3-triazoles, HOAc was recognized to accelerate the conversions of the C-Cu bond-containing intermediates and buffer the basicity of DIPEA. As a result, all drawbacks occurring in the popular catalytic system CuI/NR₃ were overcome easily.

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Carboxylic Acid-Promoted Copper(I)-Catalyzed Azide-Alkyne Cycloaddition

C. Shao, X. Wang, J. Xu, J. Zhao, Q. Zhang, Y. Hu, J. Org. Chem., 2010, 75, 7002-7005.

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Key Words

Click Chemistry, 1,2,3-Triazoles, Green Chemistry

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ID: J42-Y2011-2300