Palladium-catalyzed selective synthesis of 2-allyltetrazoles.
The palladium-catalyzed three-component coupling (TCC) reaction of cyano compounds, allyl methyl carbonate, and trimethylsilyl azide under a catalytic amount of Pd2(dba)3.CHCl3 (2.5 mol %) and tri(2-furyl)phosphine (10 mol %) gave various kinds of 2-allyltetrazoles in good to excellent yields. A pi-allylpalladium azide complex is proposed as a key intermediate in the TCC reaction.
Kamijo
Shin
S
Research Center for Sustainable Materials Engineering, Institute of Multidisciplinary Research for Advanced Materials, and Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
Jin
Tienan
T
Yamamoto
Yoshinori
Y
D000498:Allyl Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D010165:Palladium; D013329:Structure-Activity Relationship; D013777:Tetrazoles / Q000138:chemical synthesis*
D000498:Allyl Compounds; D007202:Indicators and Reagents; D013777:Tetrazoles; D010165:Palladium