Palladium-Catalyzed β-Arylation of Silyl Ketene Acetals and Application to the Synthesis of Benzo-Fused δ-Lactones

被引：27
|
作者：
Aspin, Sam [1 ]
Lopez-Suarez, Laura [1 ]
Larini, Paolo [1 ]
Goutierre, Anne-Sophie [1 ]
Jazzar, Rodolphe [1 ]
Baudoin, Olivier [1 ]
机构：
[1] Univ Lyon 1, Inst Chim & Biochim Mol & Supramol, CNRS UMR 5246, CPE Lyon, F-69622 Villeurbanne, France
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 19期
关键词：
C-H BONDS; ALPHA-ARYLATION; COUPLING REACTIONS; KETO-ESTERS; METAL; FUNCTIONALIZATION; EFFICIENT; SP(2); ACIDS;
D O I：
10.1021/ol402398s
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Silyl ketene acetals are shown to be competent nucleophiles in Pd-catalyzed migrative C(sp(3))-H arylations. Compared to the parent ester lithium enolates, they possess decreased reactivity but enhanced chemoselectivity. This behavior was exploited through the synthesis of valuable benzo-fused delta-lactones such as 1-isochromanones and dihydrocoumarins.
引用
收藏
页码：5056 / 5059
页数：4
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