Intermolecular Nonreductive Alkylation of Enamides via Radical-Polar Crossover

被引：34
|
作者：
Friestad, Gregory K. [1 ]
Wu, Yaoping [1 ]
机构：
[1] Univ Iowa, Dept Chem, Iowa City, IA 52242 USA
来源：
ORGANIC LETTERS | 2009年 / 11卷 / 04期
基金：
美国国家科学基金会;
关键词：
CARBON-CENTERED RADICALS; ATOM-TRANSFER REACTIONS; N-ACYLIMINIUM IONS; ELECTRON-TRANSFER; REDUCTIVE ALKYLATION; ADDITION-REACTIONS; ACID-DERIVATIVES; VINYL HALIDES; ENAMINES; DEHYDROALANINE;
D O I：
10.1021/ol8028077
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A carbon-carbon bond construction method is disclosed which involves radical addition of alpha-haloesters or iodoacetonitrile to enamides. Despite the presence of tri-n-butylstannane, nonreductive addition was predominant; H-atom transfer from tin hydride was not observed. Rapid iodine atom transfer to (or electron transfer from) the radical adduct, resulting in an iminium ion intermediate and radical chain propagation, is consistent with the observed reactivity.
引用
收藏
页码：819 / 822
页数：4
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