Organic azides are easily reduced to the corresponding amines by reaction with dichloroindium hydride under very mild conditions and in a highly chemoselective fashion. Azidonitriles give rise to outstanding 5-membered cyclizations affording pyrrolidin-2-imines. A rationalization of the overall experimental data cannot exclude the occurrence of competitive radical and non-radical pathways, but certain results are, however, soundly consistent with the intermediacy of indium-bound nitrogen-centered radicals.

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

BENATI, MARIA LUISA;BENCIVENNI, GIORGIO;LEARDINI, RINO;MINOZZI, MATTEO;NANNI, DANIELE;SCIALPI, ROSANNA;SPAGNOLO, PIERO;ZANARDI, GIUSEPPE
2006

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. Azidonitriles give rise to outstanding 5-membered cyclizations affording pyrrolidin-2-imines. A rationalization of the overall experimental data cannot exclude the occurrence of competitive radical and non-radical pathways, but certain results are, however, soundly consistent with the intermediacy of indium-bound nitrogen-centered radicals.
2006
M. L. Benati; G. Bencivenni; R. Leardini; M. Minozzi; D. Nanni; R. Scialpi; P. Spagnolo; G. Zanardi
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/27812
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