Syntheses of polyfunctionalized resveratrol derivatives using Wittig and Heck protocols
- 作者：Malik Chalal ; Dominique Vervandier-Fasseur ; dominique.vervandier-fasseur@u-bourgogne.fr ; Philippe Meunier ; Hé ; lè ; ne Cattey ; Jean-Cyrille Hierso ; jean-cyrille.hierso@u-bourgogne.fr
- 关键词：Hydroxylated stilbenes ; Wittig reaction ; Protective group ; Heck coupling ; Ferrocenyl phosphane
- 刊名：Tetrahedron
- 出版年：2012
- 期刊代码：107_00404020
- 类别：ch
- 出版时间：20 May, 2012
- 卷：68
- 期：20
- 页码：3899-3907
- 文件大小：839 K
摘要
Improved protocols for Wittig reaction and palladium-catalyzed Heck coupling give expedient access to a series of unprecedented polyfunctionalized artificial-resveratrol derivatives. In the modified Wittig protocol, trimethylsilyl was used as a highly valuable protective group of the phenolic functions of starting aromatic materials. A clean O-alkylation of hydroxylated stilbenes with ethylene carbonate was also conducted. Thus, Wittig reaction followed by hydroxyethylation take place one-pot with only carbon dioxide as waste. Additionally, a palladium-catalyzed Heck coupling strategy was developed by using ferrocenyl phosphane ligands, and multi-functionalized hydroxylated stilbenes were obtained without the need of any protection/deprotection sequence. Up to six functional groups are introduced by these procedures, which limit the number of reactions steps, the waste toxicity, and the use of costly reagents.