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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