Categories: N/N Bond Formation >
Synthesis of Azides
Imidazole-1-sulfonyl azide hydrochloride equals triflyl azide in its ability to act as a “diazo donor” in the conversion of both primary amines into azides and activated methylene substrates into diazo compounds. Crucially, this reagent can be prepared in a one-pot reaction on a large scale from inexpensive materials, is shelf-stable and is conveniently crystalline.
E. D. Goddard-Borger, R. V. Stick, Org. Lett., 2007, 9, 3797-3800.
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 various aromatic amines without the need for isolation of the azide intermediates.
K. Barral, A. D. Moorhouse, J. E. Moses, Org. Lett., 2007, 9, 1809-1811.
Aliphatic and aromatic aldehydes gave acyl azides by reaction with iodine azide at 0 - 25°C. If the reaction is performed at reflux Curtius rearrangement occurs and carbamoyl azides are obtained directly from the aldehyde in 70-97% yield.
L. Marinescu, J. Thinggaard, I. B. Thomsen, M. Bols, J. Org. Chem., 2003, 68, 9453-9455.
Stable and easy to handle imidazole-1-sulfonyl azide hydrogen sulfate is an efficient reagent for the synthesis of sulfonyl azides from primary sulfonamides in an experimentally simple and high-yielding method without Cu salts. Furthermore, 15N NMR mechanistic studies show the reaction proceeds via a diazo transfer mechanism.
M. Y. Stevens R. T. Sawant, L. R. Odell, J. Org. Chem., 2014, 79, 4826-4831.
Triflyl azide serves as an efficient diazo transfer reagent in a direct synthesis of sulfonyl azide building blocks from readily available and stable sulfonamides. The process is experimentally simple, mild, and high-yielding.
J. Raushel, S. M. Pitram, V. V. Fokin, Org. Lett., 2008, 10, 3385-3388.