Synthesis of aryl azides: A probe reaction to study the synergetic action of ultrasounds and ionic liquids

The combined effect of ultrasounds and ionic liquids was used to perform the synthesis of aryl azides by nucleophilic aromatic substitution in ionic liquid/[1-butyl-3-methylimidazolium][N-3] binary mixtures. The ultrasounds efficiency was analyzed as a function of the substrate and of the ionic liquid structure. In the first case, both 6 pi and 10 pi electrons aryl halides were considered. As far as the ionic liquid structure is concerned, both aromatic and aliphatic ionic liquids were taken into account. Among aromatic cations, the effects due to different ability in giving hydrogen bond or pi-pi interactions were considered. The use of a geminal ionic liquid having an aromatic spacer was examined too. On the whole, collected data evidence an activating effect on the target reaction by the combined use of ultrasounds and ionic liquids. The structural order degree of the ionic liquid seems to be the main factor affecting the ultrasounds efficiency. Furthermore, the effects due to changes in the anion structure seem to be more significant than those due to changes in the cation structure. (C) 2011 Elsevier B.V. All rights reserved.