Selective Intramolecular C-H Amination through the Metalloradical Activation of Azides: Synthesis of 1,3-Diamines under Neutral and Nonoxidative Conditions

被引:167
|
作者
Lu, Hongjian [1 ]
Jiang, Huiling [1 ]
Wojtas, Lukasz [1 ]
Zhang, X. Peter [1 ]
机构
[1] Univ S Florida, Dept Chem, Tampa, FL 33620 USA
基金
美国国家科学基金会;
关键词
C-H amination; cobalt porphyrins; 1,3-diamines; nitrene transfer; sulfamoyl azides; TRANSITION-METAL-COMPLEXES; ORGANIC AZIDES; EFFICIENT; INSERTION; BONDS; FUNCTIONALIZATION; AZIRIDINATION; AMIDATION; DESIGN; AMINES;
D O I
10.1002/anie.201005552
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
N2 is the only by-product in a stereospecific and highly diastereoselective intramolecular C-H amination of sulfamoyl azides with a cobalt(II)-based metalloradical catalyst (see scheme). The catalytic system has an unusual capacity for the efficient amination of strong primary C-H bonds, as well as secondary and tertiary C-H bonds, and functional-group tolerance is excellent owing to the neutral and nonoxidative conditions. Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:10192 / 10196
页数:5
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