Allylic Azidation in Water

Significance

Catalytic azidation of allyl esters with sodium azide was achieved in water under mild conditions in the presence of an amphiphilic polystyrene-poly(ethylene glycol) resin-supported palladium complex. Allylic carbonate esters of primary, secondary, tertiary, and cyclic alcohols (11 examples) were examined to give 70-96% isolated yields of the corresponding allylic azides. Recycling experiments were examined for azidation of the cinnamyl carbonate. Thus, the used polymeric palladium beads were recovered by simple filtration and taken on to the recycling experiments to exhibit stable catalytic activity for several reuses. The standard conditions: The reaction was carried out in water at 25 °C for 24 h. The ratio of allyl ester (mol)/NaN₃ (mol)/Pd (mol)/H₂O (L) was 1/1.5/0.01/3.