Simple and Efficient Method for the Preparation of Aryl Azides Using Sonication

Abstract

An efficient procedure for the preparation of aryl azides using sonication is described. The convenient sonication-mediated azidation protocol is applicable to aryl compounds under mild conditions with aqueous solution of sodium dichloroiodate and sodium azide. Aryl azides were obtained in excellent yields from a variety of aryl compounds in short reaction times without affecting sensitive functional groups.

GRAPHICAL ABSTRACT

Keywords:

• Aryl azides
• sodium azide
• sodium dichloroiodate
• sonication

ACKNOWLEDGMENT

K. A. S. gratefully acknowledges the Council of Scientific and Industrial Research, Delhi, India, for financial support.

Notes

^a Reaction conditions: Substrate (1.0 equiv), aqueous solution of sodium dichloroiodate (1.5 M, 1.01 equiv), and sodium azide (1.01 equiv) at room temperature combined with sonication.

^b Starting compounds were prepared by standard reported procedures.

^c Isolated yields after column chromatography and structures were confirmed by comparison of the IR and ¹H NMR spectra with those of authentic materials.^{[ 3 , 4 ,} 20-22 ^]

^d No reaction.