Studies in Acyl C-H Activation via Aryl and Alkyl to Acyl "Through Space" Migration of Palladium

被引：47

作者：

Kesharwani, Tanay ^{[1
]}

Verma, Akhilesh K. ^{[2
]}

Emrich, Daniel ^{[1
]}

Ward, Jeffrey A. ^{[1
]}

Larock, Richard C. ^{[1
]}

机构：

[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA

[2] Univ Delhi, Dept Chem, Delhi 110007, India

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 12期

基金：

美国国家科学基金会;

关键词：

O-ALKENYL ANILIDES; VINYLIC HALIDES; 1,4-PALLADIUM MIGRATION; SUBSTITUTED CARBAZOLES; NITROGEN-HETEROCYCLES; NONCONJUGATED DIENES; UNSATURATED PHENOLS; FUSED POLYCYCLES; IODIDES; ACIDS;

D O I：

10.1021/ol900940k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Examples of the 1,4-migration of a palladium moiety in aryl- and alkylpalladium intermediates to the acyl position of an aldehyde or formamide have been observed. The resulting acylpalladium intermediate can undergo ester or carbamate formation by reaction with an alcohol; decarbonylation, followed by beta hydride elimination to an alkene; reaction with an organomercurial to form an ester; or alkene insertion. Deuterium-labeling studies have been used to confirm the palladium migration mechanism.

引用

收藏

页码：2591 / 2593

页数：3

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