Carboxylic Acid-Promoted Copper(I)-Catalyzed Azide-Alkyne Cycloaddition
Changwei Shao, Xinyan Wang*, Jimin Xu, Jichen Zhao, Qun Zhang and Yuefei Hu*
*Department of Chemistry, Tsinghua University, Beijing 100084, People's Republic of China, Email: wangxinyanmail.tsinghua.edu.cn, yfhmail.tsinghua.edu.cn
C. Shao, X. Wang, J. Xu, J. Zhao, Q. Zhang, Y. Hu, J. Org. Chem., 2010, 75, 7002-7005.
DOI: 10.1021/jo101495k (free Supporting Information)
Key steps in the catalytic cycle of CuAAC can proceed in the presence of carboxylic acids and can be promoted significantly by carboxylic acids. Benzoic acid showed the best promotion activity, and acids with strong chelating ability to the Cu(I) ion could not serve for this purpose. Thus, the first carboxylic acid-promoted highly efficient CuAAC was established.
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C. Shao, X. Wang, Q. Zhang, S. Luo, J. Zhao, Y. Hu, J. Org. Chem., 2011, 76, 6832-6836.