Green Hydroselenation of Aryl Alkynes: Divinyl Selenides as a Precursor of Resveratrol
by
Gelson Perin 1,*
, Angelita M. Barcellos 1, Eduardo Q. Luz 1, Elton L. Borges 1, Raquel G. Jacob 1, Eder J. Lenardão 1, Luca Sancineto 2 and 
Claudio Santi 2,*
Gelson Perin 1,*, Angelita M. Barcellos 1, Eduardo Q. Luz 1, Elton L. Borges 1, Raquel G. Jacob 1, Eder J. Lenardão 1, Luca Sancineto 2 and Claudio Santi 2,*
1
Laboratório de Síntese Orgânica Limpa-LASOL-CCQFA, Universidade Federal de Pelotas-UFPel, P.O. Box 354, 96010-900 Pelotas, RS, Brazil
2
Department of Pharmaceutical Sciences, Group of Catalysis and Organic Green Chemistry, University of Perugia, Via del Liceo 1, 06100 Perugia, Italy
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Molecules 2017, 22(2), 327; https://doi.org/10.3390/molecules22020327
Received: 19 January 2017 / Revised: 14 February 2017 / Accepted: 16 February 2017 / Published: 20 February 2017
(This article belongs to the Special Issue Celebrating Two Centuries of Research in Selenium Chemistry: State of the Art and New Prospectives)
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.
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Keywords:
selenium; PEG-400; tellurium; resveratrol; chalcogen alkenes
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MDPI and ACS Style
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.
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