Stereoselective preparation of (E)- and (Z)-α-fluorostilbenes via palladium-catalyzed cross-coupling reaction of high E/Z ratio and (Z)-1-bromo-1-fluoroalkenes

被引：21

作者：

Xu, JJ ^{[1
]}

Burton, DJ ^{[1
]}

机构：

[1] Univ Iowa, Dept Chem, Iowa City, IA 52242 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 10期

关键词：

D O I：

10.1021/jo060068i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly stereoselective method to prepare both (E)- and (Z)-R-fluorostilbenes is described. 1-Bromo-1-fluoroalkenes (E/Z approximate to 1:1), a readily available starting material, isomerizes to high E/Z ratios by storage at - 20 C or by photolysis at 254 nm. Stille coupling between these high E/Z 1-bromo-1-fluoroalkenes and aryl stannanes gave (Z)-alpha-fluorostilbenes in high stereoselectivity. (Z)-1-Bromo-1-fluoroalkenes, which were kinetically separated from 1-bromo-1-fluoroalkenes (E/Z approximate to 1:1), can participate in Suzuki coupling reactions to give (E)-alpha-fluorostilbenes stereoselectively.

引用

页码：3743 / 3747

页数：5

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