Contribuição ao estudo de reações mediadas por calcogenetos Zn e Cu: hidrocalcogenação de ácidos e ésteres e síntese de sulfetos arílicos

Detalhes bibliográficos
Ano de defesa: 2012
Autor(a) principal: Nunes, Vanessa Loren lattes
Orientador(a): Barros, Olga Soares do Rêgo lattes
Banca de defesa: Barros, Olga Soares do Rêgo, Souza, Aparecido Ribeiro de, Vasconcellos, Mário Luiz Araújo de Almeida
Tipo de documento: Dissertação
Tipo de acesso: Acesso aberto
Idioma: por
Instituição de defesa: Universidade Federal de Goiás
Programa de Pós-Graduação: Programa de Pós-graduação em Química (IQ)
Departamento: Instituto de Química - IQ (RG)
País: Brasil
Palavras-chave em Português:
Compostos organometálicos
Acoplamento cruzado
Palavras-chave em Inglês:
Organometalic compounds
Cross coupling
Área do conhecimento CNPq:
QUIMICA::QUIMICA ANALITICA
Link de acesso: http://repositorio.bc.ufg.br/tede/handle/tede/3097
Resumo: This work describes some studies on the preparation of unsymmetrical diaryl thioethers catalyzed by Copper(I)-Senelenophene-2-carboxylate. The results concern to the catalyzed cross-coupling reaction between aryl halides and aryl or alkylthiols using Copper(I)-Senelenophene-2-carboxylate (CuSC) a new Cu-catalyzed one-pot protocol. The products were obtained in good to excellent yields under relatively mild reaction conditions presenting chemoselectivity and functional group tolerance. Additionally, we have developed a chemio-, regio and stereoselective synthesis of vinyl chalcogenides compounds promoted by zinc chalcogenolates. In this protocol the reductive cleavage of chalcogen bond by the Zn/NH4OH system led to zinc chalcogenolates. The reaction was carried out with acids and esters propiolics afford β-chalcogenacrillic acids and esters under mild and basic conditions. The stereochemistry corresponding to anti-Markovnikov addition of the chalcogenolate constituents across the triple bond were obtained in good yields.
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spelling Barros, Olga Soares do Rêgohttp://lattes.cnpq.br/8311808341863723Barros, Olga Soares do RêgoSouza, Aparecido Ribeiro deVasconcellos, Mário Luiz Araújo de Almeidahttp://lattes.cnpq.br/3611308478246793Nunes, Vanessa Loren2014-09-19T11:28:41Z2012-05-04Nunes, Vanessa Loren. Contribuição ao estudo de reações mediadas por calcogenetos Zn e Cu: hidrocalcogenação de ácidos e ésteres e síntese de sulfetos arílicos. 2012. 117 f. Dissertação (Mestrado em Química) - Universidade Federal de Goiás, Goiânia, 2012.http://repositorio.bc.ufg.br/tede/handle/tede/3097This work describes some studies on the preparation of unsymmetrical diaryl thioethers catalyzed by Copper(I)-Senelenophene-2-carboxylate. The results concern to the catalyzed cross-coupling reaction between aryl halides and aryl or alkylthiols using Copper(I)-Senelenophene-2-carboxylate (CuSC) a new Cu-catalyzed one-pot protocol. The products were obtained in good to excellent yields under relatively mild reaction conditions presenting chemoselectivity and functional group tolerance. Additionally, we have developed a chemio-, regio and stereoselective synthesis of vinyl chalcogenides compounds promoted by zinc chalcogenolates. In this protocol the reductive cleavage of chalcogen bond by the Zn/NH4OH system led to zinc chalcogenolates. The reaction was carried out with acids and esters propiolics afford β-chalcogenacrillic acids and esters under mild and basic conditions. The stereochemistry corresponding to anti-Markovnikov addition of the chalcogenolate constituents across the triple bond were obtained in good yields.Este trabalho descreve o estudo das reações de acoplamento cruzado entre iodetos arílicos e tióis arílicos ou alquílicos catalisada por 2-carboxilato selenofeno de cobre (I) (CuSC). Apresentamos uma nova metodologia “ one pote” para a síntese de tioésteres arílicos obtidos em condições reacionais relativamente brandas, apresentando quimiosseletividade, tolerância a diversos grupos funcionais e rendimentos que variam entre bons a ótimos (70-100%). R1I + R2SH K3PO4, DMSO S R1 R2 Adicionalmente, desenvolvemos uma síntese quimio, régio, e estereosseletiva de compostos vinil calcogenetos promovida por calcogenolato de zinco. Neste protocolo a clivagem redutiva da ligação calcogênio feita pelo sistema Zn/NH4OH obteve os calcogenolatos de zinco. A reação foi realizada com ácidos e ésteres propiólicos formando ácidos acrílicos β-calcogênio e ésteres sob condições básicas e brandas. A estereoquímica corresponde a adição anti-Markovnikov dos constituintes calcogenolatos através da ligação tripla. Os calcogenetos vinílicos foram obtidos em bons rendimentos (40-96).Submitted by Erika Demachki (erikademachki@gmail.com) on 2014-09-18T18:51:43Z No. of bitstreams: 2 Dissertação Vanessa Loren Nunes.pdf: 10979785 bytes, checksum: 8efff856842f8d2962b9f8221ec1fcb5 (MD5) license_rdf: 23148 bytes, checksum: 9da0b6dfac957114c6a7714714b86306 (MD5)Approved for entry into archive by Luciana Ferreira (lucgeral@gmail.com) on 2014-09-19T11:28:41Z (GMT) No. of bitstreams: 2 Dissertação Vanessa Loren Nunes.pdf: 10979785 bytes, checksum: 8efff856842f8d2962b9f8221ec1fcb5 (MD5) license_rdf: 23148 bytes, checksum: 9da0b6dfac957114c6a7714714b86306 (MD5)Made available in DSpace on 2014-09-19T11:28:41Z (GMT). No. of bitstreams: 2 Dissertação Vanessa Loren Nunes.pdf: 10979785 bytes, checksum: 8efff856842f8d2962b9f8221ec1fcb5 (MD5) license_rdf: 23148 bytes, checksum: 9da0b6dfac957114c6a7714714b86306 (MD5) Previous issue date: 2012-05-04Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqapplication/pdfhttp://repositorio.bc.ufg.br/tede/retrieve/8055/Disserta%c3%a7%c3%a3o%20Vanessa%20Loren%20Nunes.pdf.jpgporUniversidade Federal de GoiásPrograma de Pós-graduação em Química (IQ)UFGBrasilInstituto de Química - IQ (RG)ALEXAKIS, A.; POLET, D.; TISSOT-CROSSET, K. Angew. Chem. Int. Ed. v. 43, p. 2426, 2004. ALEXAKIS, A.; POLET, D. Cu-catalysed asymmetric 1,4-addition of Me3Al to nitroalkenes. Synthesis of (+)-ibuprofen, Tetrahedron Lett. v. 46, p. 1529-1532, 2005. ALEXAKIS, A.; D’ AUGUSTIN, M.; PALAIS, L. Angew. Chem. Int. Ed. v. 44, p. 1376, 2005. BETAGEL, O.; SEIBERT, H. Chem. Ber. v. 65, p. 815, 1932. BRANDSMA, L. Preparative Acetylenic Chemistry. 2ª Edition. 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European Journal, v.17, p. 8202-8208, 2011.6636939213254151586006006006007826066743741197278-8661602105461439549-2555911436985713659http://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessCompostos organometálicosAcoplamento cruzadoOrganometalic compoundsCross couplingQUIMICA::QUIMICA ANALITICAContribuição ao estudo de reações mediadas por calcogenetos Zn e Cu: hidrocalcogenação de ácidos e ésteres e síntese de sulfetos arílicosNew contributions for the synthesis of unsymmetrical diaryl thioethers and vinyl chalcogenides compunds promoted by copper Senelenophene-2-carboxylate and zinc chalcogenolatesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisreponame:Repositório Institucional da UFGinstname:Universidade Federal de Goiás (UFG)instacron:UFGLICENSElicense.txtlicense.txttext/plain; charset=utf-82165http://repositorio.bc.ufg.br/tede/bitstreams/8b4c3f84-bde8-4d67-8281-27aa1b51ebdd/downloadbd3efa91386c1718a7f26a329fdcb468MD51CC-LICENSElicense_urllicense_urltext/plain; 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dc.title.por.fl_str_mv Contribuição ao estudo de reações mediadas por calcogenetos Zn e Cu: hidrocalcogenação de ácidos e ésteres e síntese de sulfetos arílicos
dc.title.alternative.eng.fl_str_mv New contributions for the synthesis of unsymmetrical diaryl thioethers and vinyl chalcogenides compunds promoted by copper Senelenophene-2-carboxylate and zinc chalcogenolates
title Contribuição ao estudo de reações mediadas por calcogenetos Zn e Cu: hidrocalcogenação de ácidos e ésteres e síntese de sulfetos arílicos
spellingShingle Contribuição ao estudo de reações mediadas por calcogenetos Zn e Cu: hidrocalcogenação de ácidos e ésteres e síntese de sulfetos arílicos
Nunes, Vanessa Loren
Compostos organometálicos
Acoplamento cruzado
Organometalic compounds
Cross coupling
QUIMICA::QUIMICA ANALITICA
title_short Contribuição ao estudo de reações mediadas por calcogenetos Zn e Cu: hidrocalcogenação de ácidos e ésteres e síntese de sulfetos arílicos
title_full Contribuição ao estudo de reações mediadas por calcogenetos Zn e Cu: hidrocalcogenação de ácidos e ésteres e síntese de sulfetos arílicos
title_fullStr Contribuição ao estudo de reações mediadas por calcogenetos Zn e Cu: hidrocalcogenação de ácidos e ésteres e síntese de sulfetos arílicos
title_full_unstemmed Contribuição ao estudo de reações mediadas por calcogenetos Zn e Cu: hidrocalcogenação de ácidos e ésteres e síntese de sulfetos arílicos
title_sort Contribuição ao estudo de reações mediadas por calcogenetos Zn e Cu: hidrocalcogenação de ácidos e ésteres e síntese de sulfetos arílicos
author Nunes, Vanessa Loren
author_facet Nunes, Vanessa Loren
author_role author
dc.contributor.advisor1.fl_str_mv Barros, Olga Soares do Rêgo
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/8311808341863723
dc.contributor.referee1.fl_str_mv Barros, Olga Soares do Rêgo
dc.contributor.referee2.fl_str_mv Souza, Aparecido Ribeiro de
dc.contributor.referee3.fl_str_mv Vasconcellos, Mário Luiz Araújo de Almeida
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/3611308478246793
dc.contributor.author.fl_str_mv Nunes, Vanessa Loren
contributor_str_mv Barros, Olga Soares do Rêgo
Barros, Olga Soares do Rêgo
Souza, Aparecido Ribeiro de
Vasconcellos, Mário Luiz Araújo de Almeida
dc.subject.por.fl_str_mv Compostos organometálicos
Acoplamento cruzado
topic Compostos organometálicos
Acoplamento cruzado
Organometalic compounds
Cross coupling
QUIMICA::QUIMICA ANALITICA
dc.subject.eng.fl_str_mv Organometalic compounds
Cross coupling
dc.subject.cnpq.fl_str_mv QUIMICA::QUIMICA ANALITICA
description This work describes some studies on the preparation of unsymmetrical diaryl thioethers catalyzed by Copper(I)-Senelenophene-2-carboxylate. The results concern to the catalyzed cross-coupling reaction between aryl halides and aryl or alkylthiols using Copper(I)-Senelenophene-2-carboxylate (CuSC) a new Cu-catalyzed one-pot protocol. The products were obtained in good to excellent yields under relatively mild reaction conditions presenting chemoselectivity and functional group tolerance. Additionally, we have developed a chemio-, regio and stereoselective synthesis of vinyl chalcogenides compounds promoted by zinc chalcogenolates. In this protocol the reductive cleavage of chalcogen bond by the Zn/NH4OH system led to zinc chalcogenolates. The reaction was carried out with acids and esters propiolics afford β-chalcogenacrillic acids and esters under mild and basic conditions. The stereochemistry corresponding to anti-Markovnikov addition of the chalcogenolate constituents across the triple bond were obtained in good yields.
publishDate 2012
dc.date.issued.fl_str_mv 2012-05-04
dc.date.accessioned.fl_str_mv 2014-09-19T11:28:41Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/masterThesis
format masterThesis
status_str publishedVersion
dc.identifier.citation.fl_str_mv Nunes, Vanessa Loren. Contribuição ao estudo de reações mediadas por calcogenetos Zn e Cu: hidrocalcogenação de ácidos e ésteres e síntese de sulfetos arílicos. 2012. 117 f. Dissertação (Mestrado em Química) - Universidade Federal de Goiás, Goiânia, 2012.
dc.identifier.uri.fl_str_mv http://repositorio.bc.ufg.br/tede/handle/tede/3097
identifier_str_mv Nunes, Vanessa Loren. Contribuição ao estudo de reações mediadas por calcogenetos Zn e Cu: hidrocalcogenação de ácidos e ésteres e síntese de sulfetos arílicos. 2012. 117 f. Dissertação (Mestrado em Química) - Universidade Federal de Goiás, Goiânia, 2012.
url http://repositorio.bc.ufg.br/tede/handle/tede/3097
dc.language.iso.fl_str_mv por
language por
dc.relation.program.fl_str_mv 663693921325415158
dc.relation.confidence.fl_str_mv 600
600
600
600
dc.relation.department.fl_str_mv 7826066743741197278
dc.relation.cnpq.fl_str_mv -8661602105461439549
dc.relation.sponsorship.fl_str_mv -2555911436985713659
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