Selective Cross-Coupling of Organic Halides with Allylic Acetates

被引：97

作者：

Anka-Lufford, Lukiana L. ^{[1
]}

Prinsell, Michael R. ^{[1
]}

Weix, Daniel J. ^{[1
]}

机构：

[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 22期

基金：

美国国家卫生研究院;

关键词：

ARYL HALIDES; SUBSTITUTION-REACTION; DIRECT INSERTION; BROMIDES; ZINC; ALKYLATION; ALCOHOLS; REGIOCHEMISTRY; REARRANGEMENT; ALLYLATION;

D O I：

10.1021/jo302086g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general protocol for the coupling of haloarenes with a variety of allylic acetates is presented. Strengths of the method are a tolerance for electrophilic (ketone, aldehyde) and acidic (sulfonamide, trifluoroacetamide) substrates and the ability to couple with a variety of substituted allylic acetates. Secondary alkyl bromides can also be allylated under slightly modified conditions, demonstrating the generality of the approach. Finally, the coupling of a reactive vinyl halide could be achieved by the use of a very hindered ligand and more reactive, branched allylic acetates.

引用

页码：9989 / 10000

页数：12

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