67502-78-7Relevant academic research and scientific papers
Green hydroselenation of aryl alkynes: Divinyl selenides as a precursor of resveratrol
Perin, Gelson,Barcellos, Angelita M.,Luz, Eduardo Q.,Borges, Elton L.,Jacob, Raquel G.,Lenard?o, Eder J.,Sancineto, Luca,Santi, Claudio
, (2017/03/08)
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.
Stereoselective synthesis of enynes by nickel-catalyzed cross-coupling of divinylic chalcogenides with alkynes
Silveira, Claudio C.,Braga, Antonio L.,Vieira, Adriano S.,Zeni, Gilson
, p. 662 - 665 (2007/10/03)
(Z,Z)- and (E,E)-divinylic selenides and telurides undergo direct coupling with terminal alkynes in the presence of a nickel/CuI catalyst at room temperature to give (Z)- and (E)-enyne systems in good yields and with complete retention of configuration.
STEREOSPECIFIC SYNTHESIS OF DIVINYL SELENIDES. NUCLEOPHILIC SUBSTITUTIONS OF UNACTIVATED VINYL HALIDES BY VINYL SELENIDE ANIONS
Testaferri, Lorenzo,Tiecco, Marcello,Tingoli, Marco,Chianelli, Donatella
, p. 63 - 69 (2007/10/02)
Vinyl alkyl selenides can be dealkylated by nucleophilic substitution or by electron transfer to give vinyl selenide anions which retain the configuration of the starting products.The same anions are also produced by electron transfer from vinyl acetyl selenides.The vinyl selenide anions react with vinyl halides, in DMF or DMA, to give divinyl selenides.These reactions occur with retention of configuration and present a new example of nucleophilic substitutions of unactivated vinyl halides.
