Preparation of 2,3-disubstituted indoles by sequential Larock heteroannulation and silicon-based cross-coupling reactions

被引：31

作者：

Denmark, Scott E. ^{[1
]}

Baird, John D. ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA

来源：

TETRAHEDRON | 2009年 / 65卷 / 16期

关键词：

Cross-coupling; Indoles; Silanols; Palladium catalysis; Alkynes; PALLADIUM-CATALYZED ANNULATION; REGIOSPECIFIC SYNTHESIS; ARYL IODIDES; REGIOSELECTIVITY; DEOXYGENATION; HETEROCYCLES; DERIVATIVES; CYCLIZATION; REACTIVITY;

D O I：

10.1016/j.tet.2008.10.043

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and convergent synthesis of 2,3-disubstituted indoles has been developed using a sequential Larock indole synthesis and silicon-based, cross-coupling reaction. Substituted 2-iodoanilines reacted with an alkynyldimethylsilyl tert-butyl ether to afford indole-2-silanols under the Larock hetero-annulation conditions after hydrolysis. The corresponding sodium 2-indolylsilanolate salts successfully engaged in cross-coupling with aryl bromides and chlorides to afford multi-substituted indoles. The development of an alkynyldimethylsilyl tert-butyl ether as a masked silanol equivalent enabled a smooth heteroannulation process and the identification of a suitable catalyst/ligand combination provided for a facile cross-coupling reaction. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：3120 / 3129

页数：10

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