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
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
收藏
页码:9989 / 10000
页数:12
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