Tetrazole synthesis via the palladium-catalyzed three component coupling reaction.
The synthesis of tetrazoles was achieved via the palladium-catalyzed three component coupling (TCC) reaction; The TCC reaction of malononitrile derivatives, allyl acetate and trimethylsilyl azide proceeds very smoothly under a catalytic amount of Pd(PPh3)4 to give 2-allyltetrazoles, and further the TCC reaction of various activated cyano compounds, allyl methyl carbonate and trimethylsilyl azide proceeds readily under a catalytic amount of Pd2(dba)3 x CHCl3 and (2-furyl)3P to give 2-allyltetrazoles. pi-Allylpalladium azide complex is proposed as a key intermediate in the catalytic cycle and the [3 + 2] cycloaddition between the pi-allylpalladium azide complex and cyano compounds most probably gives the tetrazole frameworks. The deallylation of the derived allyltetrazoles was attained via the two-step procedure; the ruthenium-catalyzed isomerization and ozonolysis.
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
Gyoung
Young Soo
YS
Shim
Jae-Goo
JG
Yamamoto
Yoshinori
Y
D000498:Allyl Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D010165:Palladium; D013329:Structure-Activity Relationship; D013777:Tetrazoles / Q000138:chemical synthesis*
D000498:Allyl Compounds; D007202:Indicators and Reagents; D013777:Tetrazoles; D010165:Palladium