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.

引用

页码：769 / 777

页数：9

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