Annulation of internal alkynes through a hydroamination/aza-Heck reaction sequence for the regioselective synthesis of indoles

被引：57
作者：
Ackermann, Lutz [1 ]
Sandmann, Rene [1 ]
Villar, Amparo [1 ]
Kaspar, Ludwig T. [1 ]
机构：
[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
来源：
TETRAHEDRON | 2008年 / 64卷 / 05期
关键词：
D O I：
10.1016/j.tet.2007.10.117
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Highly regioselective annulation reactions of unsymmetrically substituted alkynes by primary 2-bromo or 2-chloroanilines are achieved with an efficient one-pot protocol, which relies on a regioselective TiCl(4)-catalyzed intermolecular hydroamination and a subsequent palladium-catalyzed intramolecular aza-Heck reaction. The use of unsymmetrically substituted alkynes in this strategy enables the synthesis of diversely functionalized indoles, with a regioselectivity that is complementary to the one obtained when employing Larock's annulation reaction. (c) 2007 Elsevier Ltd. All rights reserved.
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收藏
页码：769 / 777
页数：9
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