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

Karine Barral (1) , Adam Moorhouse (1) , John Moses (1)

1 University of London [London]

[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.

Domaines: Chimie; Chimie organique

Karine Barral, Adam Moorhouse, John Moses. Efficient Conversion of Aromatic Amines into Azides: A One-Pot Synthesis of Triazole Linkages. Organic Letters, 2007, 9 (9), pp.1809-1811. ⟨10.1021/ol070527h⟩. ⟨hal-02061672⟩