Perin Gelson, Barcellos Angelita M, Luz Eduardo Q, Borges Elton L, Jacob Raquel G, Lenardão Eder J, Sancineto Luca, Santi Claudio
Laboratório de Síntese Orgânica Limpa-LASOL-CCQFA, Universidade Federal de Pelotas-UFPel, P.O. Box 354, 96010-900 Pelotas, RS, Brazil.
Department of Pharmaceutical Sciences, Group of Catalysis and Organic Green Chemistry, University of Perugia, Via del Liceo 1, 06100 Perugia, Italy.
Molecules. 2017 Feb 20;22(2):327. doi: 10.3390/molecules22020327.
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 (,)-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 with (4-methoxyphenyl)magnesium bromide afforded resveratrol trimethyl ether in 57% yield.
通过将硒化钠物种区域和立体选择性地加成到芳基炔烃上，开发了一种简单高效的制备二乙烯基硒化物的方法。亲核物种由元素硒与硼氢化钠反应原位生成，使用聚乙二醇-400作为溶剂。通过在60℃下短反应时间内进行的一步法，以中等至优异的产率获得了几种二乙烯基硒化物，且对（，）-异构体具有选择性。该方法扩展到碲，以良好的产率得到了所需的二乙烯基碲化物。此外，双（3,5-二甲氧基苯乙烯基）硒化物与（4-甲氧基苯基）溴化镁的铁催化交叉偶联反应以57%的产率得到了白藜芦醇三甲醚。
