Rhodium-Catalyzed Regioselective Amination of Secondary Allylic Trichloroacetimidates with Unactivated Aromatic Amines

被引：22

作者：

Arnold, Jeffrey S. ^{[1
]}

Stone, Robert F. ^{[1
]}

Nguyen, Hien M. ^{[1
]}

机构：

[1] Univ Iowa, Dept Chem, Iowa City, IA 52242 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 20期

关键词：

ALKYLATION; OLIGOSACCHARIDES; GLYCOSYLATION; REARRANGEMENT; ALCOHOLS;

D O I：

10.1021/ol1019025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of unactivated aromatic amines in the rhodium-catalyzed regioselective amination of secondary allylic trichloroacetimidates is explored The desired N-arylamines are obtained in high yields and regioselectivity, favoring the branched animation products. The presence of the trichloroacetimidate leaving group was found to be critical for successful regioselective amination reactions with unactivated aromatic amines Control studies show that rhodium is not simply acting as a Lewis acid to activate the trichloroacetimidate leaving group.

引用

页码：4580 / 4583

页数：4

共 33 条

[1] Homologation of allylic alcohols. An approach to cyclic and acyclic polyoxygenated compounds [J].