Abstract
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.
Highlights
Chalcogen alkenes are attractive key intermediates in the synthesis of important compounds.They are useful synthons to access conjugated or isolated olefins with total control in the geometry of the double bond [1,2,3,4,5]
We examined the possibility of using our protocol to prepare the divinyl tellurides in PEG-400
We examined the possibility of using our protocol to prepare the divinyl tellurides atmosphere until consumption of the tellurium
Summary
Chalcogen alkenes are attractive key intermediates in the synthesis of important compounds They are useful synthons to access conjugated or isolated olefins with total control in the geometry of the double bond [1,2,3,4,5]. Divinyl selenides are less studied compared to synthetic intermediates, probably due to the limited number of general methods to prepare them in a selective way. They can be prepared by a stereoconservative three-step reaction of in situ generated vinyl selenide anions with (E)- or (Z)-bromo styrenes (Scheme 1A) [13]. Divinyl selenides of (E,E)-configuration were predominantly formed by the Wittig–Horner reaction of chalcogen diphosphonate derivatives with aldehydes [14,15,16] (Scheme 1B)
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