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
收藏
页码：2222 / 2229
页数：8
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