Green Hydroselenation of Aryl Alkynes: Divinyl Selenides as a Precursor of Resveratrol

• Main Authors: Gelson Perin, Angelita M. Barcellos, Eduardo Q. Luz, Elton L. Borges, Raquel G. Jacob, Eder J. Lenardão, Luca Sancineto, Claudio Santi
• Format: Article
• Language: English
• Published: MDPI AG 2017-02-01
• Series: Molecules
• Subjects: selenium; PEG-400; tellurium; resveratrol; chalcogen alkenes
• Online Access: http://www.mdpi.com/1420-3049/22/2/327

A simple and efficient protocol to prepare divinyl selenides has been developed by the regio- and stereoselective addition of sodium selenide species to aryl alkynes. The nucleophilic species was generates in situ, from the reaction of elemental selenium with NaBH4, utilizing PEG-400 as the solvent. Several divinyl selenides were obtained in moderate to excellent yields with selectivity for the (Z,Z)-isomer by a one-step procedure that was carried out at 60 °C in short reaction times. The methodology was extended to tellurium, giving the desired divinyl tellurides in good yields. Furthermore, the Fe-catalyzed cross-coupling reaction of bis(3,5-dimethoxystyryl) selenide 3f with (4-methoxyphenyl)magnesium bromide 5 afforded resveratrol trimethyl ether 6 in 57% yield.