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

ABSTRACT: 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 NaBH?, 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.

SUBMITTER: Perin G

PROVIDER: S-EPMC6155768 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature

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

Perin Gelson G Barcellos Angelita M AM Luz Eduardo Q EQ Borges Elton L EL Jacob Raquel G RG Lenardão Eder J EJ Sancineto Luca L Santi Claudio C

Molecules (Basel, Switzerland) 20170220 2

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 react ...[more]

PMID: 28230754

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