Efficient Conversion of Aromatic Amines into Azides: A One-Pot Synthesis of Triazole Linkages

Abstract

An efficient and improved procedure for the preparation of aromatic azides and their application in the Cu(I)-catalyzed azide−alkyne 1,3-dipolar cycloaddition (“click reaction”) is described. The synthesis of aromatic azides from the corresponding amines is accomplished under mild conditions with tert-butyl nitrite and azidotrimethylsilane. 1,4-Disubstituted 1,2,3-triazoles were obtained in excellent yields from a variety of aromatic amines without the need for isolation of the azide intermediates.