Intermolecular Nonreductive Alkylation of Enamides via Radical−Polar Crossover

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• 作者：Gregory K. Friestad* ; Yaoping Wu
• 刊名：Organic Letters
• 出版年：2009
• 出版时间：February 19, 2009
• 年：2009
• 卷：11
• 期：4
• 页码：819-822
• 全文大小：159K
• 年卷期：v.11,no.4(February 19, 2009)
• ISSN：1523-7052

文摘

A carbon−carbon bond construction method is disclosed which involves radical addition of α-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.