The scope of the Heck arylation of enol ethers with arenediazonium salts: a new approach to the syntheses of flavonoids

dc.creatorMachado, AHL
dc.creatorde Sousa, MA
dc.creatorPatto, DCS
dc.creatorAzevedo, LFS
dc.creatorBombonato, FI
dc.creatorCorreia, CRD
dc.date2009
dc.date43160
dc.date2014-11-16T07:03:08Z
dc.date2015-11-26T16:20:33Z
dc.date2014-11-16T07:03:08Z
dc.date2015-11-26T16:20:33Z
dc.date.accessioned2018-03-28T23:02:57Z
dc.date.available2018-03-28T23:02:57Z
dc.identifierTetrahedron Letters. Pergamon-elsevier Science Ltd, v. 50, n. 11, n. 1222, n. 1225, 2009.
dc.identifier0040-4039
dc.identifierWOS:000263749600017
dc.identifier10.1016/j.tetlet.2009.01.017
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/72431
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/72431
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/72431
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1267831
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.descriptionThe scope of the Heck arylation of cyclic and acyclic enol ethers with arenediazonium salts was evaluated. Arylation of 2,3-dihydrofuran yielded 2-aryl-2,5-dihydrofurans as the major adducts (>99:1) except when using n-Bu(4)NHSO(4) as additive or 4-NO(2)PhN(2)BF(4) as arenediazonium salt. 2,3-Dihydropyran provided mixtures of the three possible isomeric Heck adducts. Arylation of n-butylvinylether with arenediazonium bearing electron-donating groups resulted in substituted acetophenones as almost exclusive products in good overall yields, Substituted 4H-chromenes provided 2-aryl-2H-chromenes in moderate yield when applying the Pd(OAc)(2)/2,6-di-t-butyl-4-methylpyridine catalytic system, which were applied in the synthesis of flavonoids. (C) 2009 Elsevier Ltd. All rights reserved.
dc.description50
dc.description11
dc.description1222
dc.description1225
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.languageen
dc.publisherPergamon-elsevier Science Ltd
dc.publisherOxford
dc.publisherInglaterra
dc.relationTetrahedron Letters
dc.relationTetrahedron Lett.
dc.rightsfechado
dc.rightshttp://www.elsevier.com/about/open-access/open-access-policies/article-posting-policy
dc.sourceWeb of Science
dc.subjectElectron-rich Olefins
dc.subjectPalladium-catalyzed Arylation
dc.subjectHydroxyalkyl Vinyl Ethers
dc.subjectCross-coupling Reactions
dc.subjectAcyl-n-vinylamine
dc.subjectAryl Halides
dc.subjectDiazonium Salts
dc.subjectIonic Liquid
dc.subjectRegioselective Arylation
dc.subjectAlpha-regioselectivity
dc.titleThe scope of the Heck arylation of enol ethers with arenediazonium salts: a new approach to the syntheses of flavonoids
dc.typeArtículos de revistas


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