Efficient transformation of azides to primary amines using the mild and easily accessible CeCl3.7H2O/NaI system.
Because of the nitrogen functionality, the azido group plays an important role in the synthesis of amines, and numerous reduction methods of azides to primary amines are reported. Recent reports have highlighted the capability of NaI as a useful reagent for this transformation when it is used in combination with a Lewis acid promoter. However, these methods often suffer from harsh reaction conditions; for this reason, the development of a simple and efficient protocol using NaI in presence of inexpensive and readily available cerium salts Lewis acids would extend the scope of this organic transformation. In continuation of our interest on the use of the CeCl3.7H2O/NaI system, in this paper we report how azides undergo reduction by NaI in the presence of CeCl3.7H2O in refluxing acetonitrile under neutral conditions to produce the corresponding primary amines. The rate and yield of the reaction are considerably improved by employing this microwave-assisted procedure, and this may be of value for the preparation of densely functionalized molecules having biological and pharmaceutical activities.
Bartoli
Giuseppe
G
Dipartimento di Chimica Organica A. Mangini, Università di Bologna, viale Risorgimento 4, I-40136 Bologna, Italy.
Di Antonio
Giustino
G
Giovannini
Riccardo
R
Giuli
Sandra
S
Lanari
Silvia
S
Paoletti
Melissa
M
Marcantoni
Enrico
E
D000588:Amines / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002563:Cerium / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D012974:Sodium Iodide / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D014867:Water / Q000737:chemistry
D000588:Amines; D001386:Azides; D014867:Water; D002563:Cerium; D012974:Sodium Iodide