Green Hydroselenation of Aryl Alkynes: Divinyl Selenides as a Precursor of Resveratrol
AbstractA 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. View Full-Text
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Perin, G.; Barcellos, A.M.; Luz, E.Q.; Borges, E.L.; Jacob, R.G.; Lenardão, E.J.; Sancineto, L.; Santi, C. Green Hydroselenation of Aryl Alkynes: Divinyl Selenides as a Precursor of Resveratrol. Molecules 2017, 22, 327.
Perin G, Barcellos AM, Luz EQ, Borges EL, Jacob RG, Lenardão EJ, Sancineto L, Santi C. Green Hydroselenation of Aryl Alkynes: Divinyl Selenides as a Precursor of Resveratrol. Molecules. 2017; 22(2):327.Chicago/Turabian Style
Perin, Gelson; Barcellos, Angelita M.; Luz, Eduardo Q.; Borges, Elton L.; Jacob, Raquel G.; Lenardão, Eder J.; Sancineto, Luca; Santi, Claudio. 2017. "Green Hydroselenation of Aryl Alkynes: Divinyl Selenides as a Precursor of Resveratrol." Molecules 22, no. 2: 327.
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