Mechanism of the palladium-catalyzed intramolecular hydroalkylation of 7-octene-2,4-dione

被引：98

作者：

Qian, H ^{[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 | 2003年 / 125卷 / 08期

关键词：

D O I：

10.1021/ja0293002

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cyclization of (E)-7,8-dideuterio-7-octene-2,4-dione [(E)-1-7,8-d2] catalyzed by PdCl2(CH3CN)2 (2) formed cis-2-acyl-3,4-dideuteriocyclohexanone (cis-3-3,4-d2) in 64% yield as the exclusive isotopomer. This experiment, in conjunction with additional deuterium labeling experiments, was in accord with a mechanism for the conversion of 1 to 3 catalyzed by 2 involving attack of the enol carbon atom on a palladium-complexed olefin followed by palladium migration and protonolysis from a palladium enolate complex. Copyright © 2003 American Chemical Society.

引用

页码：2056 / 2057

页数：2

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[2]

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[3]

BACKVALL JE, 1979, J AM CHEM SOC, V101, P2411

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