Biaryl Synthesis by Ring-Opening Friedel-Crafts Arylation of 1,4-Epoxy-1,4-dihydronaphthalenes Catalyzed by Iron Trichloride

被引：12

作者：

Sawama, Yoshinari ^{[1
]}

Asai, Shota ^{[1
]}

Kawajiri, Takahiro ^{[1
]}

Monguchi, Yasunari ^{[1
]}

Sajiki, Hironao ^{[1
]}

机构：

[1] Gifu Pharmaceut Univ, Organ Chem Lab, Gifu 5011196, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 05期

基金：

日本学术振兴会;

关键词：

arenes; biaryls; Friedel-Crafts reaction; iron catalyst; ring-opening reaction; OXABICYCLIC ALKENES; BIOLOGICAL EVALUATION; BICYCLIC ALKENES; EFFICIENT; GRIGNARD; DERIVATIVES; LIGANDS; DESIGN; ACIDS; BENZYLATION;

D O I：

10.1002/chem.201405558

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Biaryl and heterobiaryl compounds are important frameworks across a range of fields including pharmaceutical and functional material chemistries. We have accomplished the efficient synthesis of various naphthalene-linked arenes and heteroarenes as biaryls and heterobiaryls by the FeCl3-catalyzed Friedel-Crafts reactions accompanied by the ring-opening of the 1,4-epoxy moiety of 1,4-epoxy-1,4-dihydronaphthalenes. Especially, it is noteworthy that 1-silylated substrates were regioselectively transformed to the 3-aryl-1-silylnaphthalenes and the double Friedel-Crafts reactions using thiophene derivatives could directly produce the corresponding bis-naphthlated thiophene derivatives.

引用

页码：2222 / 2229

页数：8

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