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Apr 2007 Organic letters

Efficient conversion of aromatic amines into azides: a one-pot synthesis of triazole linkages.


Barral K, Moorhouse AD, Moses JE


[reaction: see text] 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.

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