Synthesis of biaryl compounds through three-component assembly:: Ambidentate effect of the tert-butyldimethylsilyl group for regioselective Diels-Alder and Hiyama coupling reactions

被引：80

作者：

Akai, Shuji ^{[1
]}

Ikawa, Takashi ^{[1
]}

Takayanagi, Sho-ichi ^{[1
]}

Morikawa, Yuki ^{[1
]}

Mohri, Shinya ^{[1
]}

Tsubakiyama, Masaya ^{[1
]}

Egi, Masahiro ^{[1
]}

Wada, Yasufami ^{[2
]}

Kita, Yasuyuki ^{[2
]}

机构：

[1] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, Shizuoka 4228526, Japan

[2] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 40期

关键词：

arynes; biaryls; C-C coupling; cycloaddition; synthetic methods;

D O I：

10.1002/anie.200803011

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two for the price of one: A method has been developed for the regiocontrolled synthesis of multisubstituted biaryl derivatives. This protocol involves the use of the tert-butyldimethylsilyl (TBDMS) group to direct the regioselective Diels-Alder reaction of a 3-TBDMS-benzyne with a furan derivative and a subsequent Hiyama cross-coupling reaction of the TBDMS group with aryl iodides (see scheme). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：7673 / 7676

页数：4