Synthesis of triazoles from nonactivated terminal alkynes via the three-component coupling reaction using a Pd(0)-Cu(I) bimetallic catalyst.
The synthesis of triazoles via the three-component coupling reaction of unactivated terminal alkynes, allyl carbonate, and trimethylsiyl azide under the Pd(0)-Cu(I) bimetallic catalyst is developed. The reaction most probably proceeds through the formation of a pi-allylpalladium azide complex and a copper-acetylide followed by a successive [3 + 2] cycloaddition. The deallylation of the resulting allyltriazoles proceeds very easily by the Ru-catalyzed isomerization followed by the ozonolysis of the resulting propenyltriazoles to give the triazoles in high yields.
Kamijo
Shin
S
Research Center for Sustainable Materials Engineering, Institute of Multidisciplinary Research for Advanced Materials, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
Jin
Tienan
T
Huo
Zhibao
Z
Yamamoto
Yoshinori
Y
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D010165:Palladium / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis*
D000480:Alkynes; D014230:Triazoles; D010165:Palladium; D003300:Copper