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 / M. L. Benati; G. Bencivenni; R. Leardini; M. Minozzi; D. Nanni; R. Scialpi; P. Spagnolo; G. Zanardi. - In: ORGANIC LETTERS. - ISSN 1523-7060. - STAMPA. - 8:(2006), pp. 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.
