Palladium-catalyzed cyclization/carboalkoxylation of alkenyl indoles

被引：146

作者：

Liu, C ^{[1
]}

Widenhoefer, RA ^{[1
]}

机构：

[1] Duke Univ, PM Gross Chem Lab, Durham, NC 27708 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 33期

关键词：

D O I：

10.1021/ja046810i

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reaction of 1-methyl-2-(4-pentenyl)indole with a catalytic amount of PdCl2(CH3CN)2 (5 mol %) and a stoichiometric amount of CuCl2 (3 equiv) in methanol under CO (1 atm) at room temperature for 30 min led to cyclization/carboalkoxylation to form the corresponding tetrahydrocarbazole in 83% isolated yield as a single regioisomer. Palladium-catalyzed cyclization/carboalkoxylation of 2-(4-pentenyl)indoles tolerated substitution along the alkenyl chain and at the internal and cis-terminal olefinic positions. Palladium-catalyzed cyclization/carboalkoxylation tolerated a range of alcohols and was effective for the cyclization of 2-(3-butenyl)indoles, 3-(3-butenyl)indoles, 3-(4-pentenyl)indoles, and 2-(5-hexenyl)indoles. Copyright © 2004 American Chemical Society.

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页码：10250 / 10251

页数：2

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