title: 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 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) selenide3fwith (4-methoxyphenyl)magnesium bromide5afforded resveratrol trimethyl ether6in 57% yield.
authors.affiliation: Laboratório de Síntese Orgânica Limpa-LASOL-CCQFA, Universidade Federal de Pelotas-UFPel, P.O. Box 354, 96010-900 Pelotas, RS, Brazil. gelson_perin@ufpel.edu.br.
authors.forename: Gelson
authors.initials: G
authors.lastname: Perin
authors.affiliation: Laboratório de Síntese Orgânica Limpa-LASOL-CCQFA, Universidade Federal de Pelotas-UFPel, P.O. Box 354, 96010-900 Pelotas, RS, Brazil. angelita.barcellos@gmail.com.
authors.forename: Angelita M
authors.initials: AM
authors.lastname: Barcellos
authors.affiliation: Laboratório de Síntese Orgânica Limpa-LASOL-CCQFA, Universidade Federal de Pelotas-UFPel, P.O. Box 354, 96010-900 Pelotas, RS, Brazil. eduardoquadros91@gmail.com.
authors.forename: Eduardo Q
authors.initials: EQ
authors.lastname: Luz
authors.affiliation: Laboratório de Síntese Orgânica Limpa-LASOL-CCQFA, Universidade Federal de Pelotas-UFPel, P.O. Box 354, 96010-900 Pelotas, RS, Brazil. chemistry_borges@yahoo.com.br.
authors.forename: Elton L
authors.initials: EL
authors.lastname: Borges
authors.affiliation: Laboratório de Síntese Orgânica Limpa-LASOL-CCQFA, Universidade Federal de Pelotas-UFPel, P.O. Box 354, 96010-900 Pelotas, RS, Brazil. raquel.jacob@ufpel.edu.br.
authors.forename: Raquel G
authors.initials: RG
authors.lastname: Jacob
authors.affiliation: Laboratório de Síntese Orgânica Limpa-LASOL-CCQFA, Universidade Federal de Pelotas-UFPel, P.O. Box 354, 96010-900 Pelotas, RS, Brazil. lenardao@ufpel.edu.br.
authors.forename: Eder J
authors.initials: EJ
authors.lastname: Lenardão
authors.affiliation: Department of Pharmaceutical Sciences, Group of Catalysis and Organic Green Chemistry, University of Perugia, Via del Liceo 1, 06100 Perugia, Italy. sancineto.luca@gmail.com.
authors.forename: Luca
authors.initials: L
authors.lastname: Sancineto
authors.affiliation: Department of Pharmaceutical Sciences, Group of Catalysis and Organic Green Chemistry, University of Perugia, Via del Liceo 1, 06100 Perugia, Italy. claudio.santi@unipg.it.
authors.forename: Claudio
authors.initials: C
authors.lastname: Santi
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D016566:Organoselenium Compounds / Q000138:chemical synthesis / Q000737:chemistry; D000077185:Resveratrol; D012643:Selenium / Q000737:chemistry*; D013267:Stilbenes / Q000138:chemical synthesis / Q000737:chemistry; D013691:Tellurium / Q000737:chemistry
chemical_list: D000480:Alkynes; D016566:Organoselenium Compounds; D013267:Stilbenes; D012643:Selenium; D013691:Tellurium; D000077185:Resveratrol
keywords: PEG-400; chalcogen alkenes; resveratrol; selenium; tellurium