Syntheses of polyfunctionalized resveratrol derivatives using Wittig and Heck protocols |
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Authors: | Malik Chalal Dominique Vervandier-Fasseur Philippe Meunier Hélène Cattey Jean-Cyrille Hierso |
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Affiliation: | Université de Bourgogne, Institut de Chimie Moléculaire de l’Université de Bourgogne, (ICMUB) UMR-CNRS 6302, 9 avenue Alain Savary, 21078 Dijon, France |
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Abstract: | 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. |
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