Reaction of Azides with Dichloroindium Hydride: Very Mild Production of Amines and Pyrrolidin-2-imines through Possible Indium−Aminyl Radicals
Organic Letters2006Vol. 8(12), pp. 2499–2502
Citations Over TimeTop 10% of 2006 papers
Luisa Benati, Giorgio Bencivenni, Rino Leardini, Daniele Nanni, Matteo Minozzi, Piero Spagnolo, Rosanna Scialpi, Giuseppe Zanardi
Abstract
Organic azides are easily reduced to the corresponding amines by reaction with dichloroindium hydride under very mild conditions and in a highly chemoselective fashion. Gamma-azidonitriles give rise to outstanding five-membered cyclizations affording pyrrolidin-2-imines. A rationalization of the overall experimental data cannot exclude the occurrence of competitive radical and nonradical pathways, but certain results are, however, soundly consistent with the intermediacy of indium-bound nitrogen-centered radicals. [reaction: see text]
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