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.
M. L. Benati, G. Bencivenni, R. Leardini, M. Minozzi, D. Nanni, R. Scialpi, et al. (2006). The Reaction of Azides with Dichloroindium Hydride: Very Mild Production of Amines and Pyrrolidin-2-imines through Possible Indium-Aminyl Radicals. ORGANIC LETTERS, 8, 2499-2502 [10.1021/ol0606637].
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
