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Molecules 2017, 22(2), 327;

Green Hydroselenation of Aryl Alkynes: Divinyl Selenides as a Precursor of Resveratrol

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
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 19 January 2017 / Revised: 14 February 2017 / Accepted: 16 February 2017 / Published: 20 February 2017
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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. View Full-Text
Keywords: selenium; PEG-400; tellurium; resveratrol; chalcogen alkenes selenium; PEG-400; tellurium; resveratrol; chalcogen alkenes

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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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.

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