Reaction of azides with dichloroindium hydride: Very mild production of amines and pyrrolidin-2-imines through possible indium-aminyl radicals

被引：67

作者：

Benati, Luisa ^{[1
]}

Bencivenni, Giorgio ^{[1
]}

Leardini, Rino ^{[1
]}

Nanni, Daniele ^{[1
]}

Minozzi, Matteo ^{[1
]}

Spagnolo, Piero ^{[1
]}

Scialpi, Rosanna ^{[1
]}

Zanardi, Giuseppe ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 12期

关键词：

D O I：

10.1021/ol0606637

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2499 / 2502

页数：4

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