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

页码：5056 / 5059

页数：4

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