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Reaction of Azides with Dichloroindium Hydride: Very Mild Production of Amines and Pyrrolidin-2-imines through Possible Indium-Aminyl Radicals

Luisa Benati, Giorgio Bencivenni, Rino Leardini, Daniele Nanni,* Matteo Minozzi, Piero Spagnolo, Rosanna Scialpi and Giuseppe Zanardi

*Dipartimento di Chimica Organica "A. Mangini", UniversitÓ di Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy, Email: nannims.fci.unibo.it

L. Benati, G. Bencivenni, R. Leardini, D. Nanni, M. Minozzi, P. Spagnolo, R. Scialpi, G. Zanardi, Org. Lett., 2006, 8, 2499-2502.

DOI: 10.1021/ol0606637 (free Supporting Information)


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Abstract

Organic azides are easily and chemoselectively reduced to the corresponding amines by reaction with dichloroindium hydride under very mild conditions. γ-Azidonitriles  give pyrrolidin-2-imines in an outstanding cyclization.

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Key Words

Reduction of Azides, Azides, Dicholorindium Hydride, Triethylsilane, Lactams (related), Amidines


ID: J54-Y2006-1670