Carboxylic acid-promoted copper(I)-catalyzed azide-alkyne cycloaddition.
In this article, we proved that all three key steps in the catalytic cycle of CuAAC can proceed in the presence of carboxylic acids and the latter two steps can be promoted significantly by carboxylic acids. Benzoic acid showed the best promotion activity, and the acids with strong chelating ability to Cu(I) ion could not serve for this purpose. Thus, the first carboxylic acid-promoted highly efficient CuAAC was established.
Shao
Changwei
C
Department of Chemistry, Tsinghua University, Beijing 100084, People's Republic of China.
Wang
Xinyan
X
Xu
Jimin
J
Zhao
Jichen
J
Zhang
Qun
Q
Hu
Yuefei
Y
D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D001386:Azides; D002264:Carboxylic Acids; D014230:Triazoles; D003300:Copper