Copper(I)/succinic acid cooperatively catalyzed one-pot synthesis of organoselenium-propargylamines via A3-coupling

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dc.contributorLab. Biofísicapt_BR
dc.contributor.authorOliveira, Isadora M. dept_BR
dc.contributor.authorPimenta, Daniel Carvalhopt_BR
dc.contributor.authorZukerman-Schpector, Juliopt_BR
dc.contributor.authorStefani, Hélio A.pt_BR
dc.contributor.authorManarin, Fláviapt_BR
dc.date.accessioned2020-07-09T21:20:32Z-
dc.date.available2020-07-09T21:20:32Z-
dc.date.issued2018pt_BR
dc.identifier.citationOliveira IM., Pimenta DC, Zukerman-Schpector J, Stefani HA., Manarin F. Copper(I)/succinic acid cooperatively catalyzed one-pot synthesis of organoselenium-propargylamines via A3-coupling. New J. Chem.. 2018;42(12): 10118-23. doi:10.1039/c8nj01543k.pt_BR
dc.identifier.urihttps://repositorio.butantan.gov.br/handle/butantan/2500-
dc.description.abstractSelenium propargylamines were synthesized via an A(3)-coupling approach using piperidine, p-methoxybenzaldehyde, and trimethylsilyl selenium-acetylene, catalyzed by copper(i) chloride and succinic acid as an additive, in good to excellent yields. This method is advantageous in that desilylation of the trimethylsilyl selenium-acetylene occurs in situ. The reaction time was monitored by FTIR studies and a probable mechanism is described. Scale-up was also performed in satisfactory yield. These selenium propargylamines could be hydrohalogenated to synthesize halovinyl selenides. The stereochemistry was determined by treatment with n-butyllithium and the coupling constant (J) values in H-1 NMR spectra. The vinyl selenides were employed in Sonogashira cross-coupling reactions to produce the corresponding enynes, with yields ranging from moderate to good.pt_BR
dc.description.sponsorshipFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)pt_BR
dc.description.sponsorshipConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)pt_BR
dc.description.sponsorshipFinanciadora de Estudos e Projetos (FINEP)pt_BR
dc.description.sponsorshipFundação Araucária de Apoio ao Desenvolvimento Científico e Tecnológico do Estado do Paraná (FA)pt_BR
dc.format.extentp. 10118-10123pt_BR
dc.language.isoEnglishpt_BR
dc.relation.ispartofNew Journal of Chemistrypt_BR
dc.titleCopper(I)/succinic acid cooperatively catalyzed one-pot synthesis of organoselenium-propargylamines via A3-couplingpt_BR
dc.typeArticlept_BR
dc.identifier.doi10.1039/c8nj01543kpt_BR
dc.identifier.urlhttp://dx.doi.org/10.1039/c8nj01543kpt_BR
dc.contributor.externalUniversidade de São Paulo (USP)¦¦Brasilpt_BR
dc.contributor.externalUniversidade Federal de São Carlos (UFSCar)¦¦Brasilpt_BR
dc.contributor.externalUniversidade Estadual do Oeste do Paraná (UNIOESTE)¦¦Brasilpt_BR
dc.identifier.citationvolume42pt_BR
dc.identifier.citationissue12pt_BR
dc.relation.ispartofabbreviatedNew J Chempt_BR
dc.identifier.citationabntv. 42, n. 12, p. 10118-10123, 2018pt_BR
dc.identifier.citationvancouver2018;42(12): 10118-23pt_BR
dc.contributor.butantanPimenta, Daniel Carvalho|:Pesquisador:Docente Permanente PPGTOX|:Lab. Biofísica|:pt_BR
dc.sponsorship.butantanConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)¦¦306119/2014-5pt_BR
dc.sponsorship.butantanConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)¦¦305626/2013-2pt_BR
dc.sponsorship.butantanFinanciadora de Estudos e Projetos (FINEP)¦¦01.09.0278.04pt_BR
dc.sponsorship.butantanFundação Araucária de Apoio ao Desenvolvimento Científico e Tecnológico do Estado do Paraná (FA)¦¦FGM-Unioeste 003/2017pt_BR
dc.sponsorship.butantanFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)¦¦2016/04289-3pt_BR
dc.identifier.bvsccBR78.1pt_BR
dc.identifier.bvsdbIBProdpt_BR
dc.description.dbindexedYespt_BR
item.openairetypeArticle-
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item.grantfulltextnone-
item.languageiso639-1English-
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