Facile synthesis of symmetrical 3,3-diarylacrylates by a Heck-Matsuda reaction : an expedient route to biologically active indanones.

Detalhes bibliográficos
Autor(a) principal: Taylor, Jason Guy
Data de Publicação: 2011
Outros Autores: Ribeiro, Rodrigo da Silva, Correia, Carlos Roque Duarte
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UFOP
dARK ID: ark:/61566/0013000003g5z
Texto Completo: http://www.repositorio.ufop.br/handle/123456789/4979
https://doi.org/10.1016/j.tetlet.2011.05.039
Resumo: A simple and straightforward synthesis of symmetrical 3,3-diarylacrylates based on a Heck-Matsuda reaction of arenediazonium salts bearing electron-donating groups with methylacrylates is described. The reaction employs Pd(OAc)2 as catalyst and goes to completion within 1 h affording the corresponding unsaturated diaryl esters in good to high yields. This method permitted the expeditious and efficient synthesis of the anticancer 3-arylindanone 5 in two operative steps in 43% overall yield.
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spelling Facile synthesis of symmetrical 3,3-diarylacrylates by a Heck-Matsuda reaction : an expedient route to biologically active indanones.Arenediazonium tetrafluoroboratesHeck-MatsudaArylationIndanonesPalladiumA simple and straightforward synthesis of symmetrical 3,3-diarylacrylates based on a Heck-Matsuda reaction of arenediazonium salts bearing electron-donating groups with methylacrylates is described. The reaction employs Pd(OAc)2 as catalyst and goes to completion within 1 h affording the corresponding unsaturated diaryl esters in good to high yields. This method permitted the expeditious and efficient synthesis of the anticancer 3-arylindanone 5 in two operative steps in 43% overall yield.2015-04-09T11:00:01Z2015-04-09T11:00:01Z2011info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfTAYLOR, J. G.; RIBEIRO, R. da S.; CORREIA, C. R. D. Facile synthesis of symmetrical 3,3-diarylacrylates by a Heck-Matsuda reaction: an expedient route to biologically active indanones. Tetrahedron Letters, v. 52, p. 3861-3864, 2011. Disponível em: <http://www.sciencedirect.com/science/article/pii/S0040403911007763>. Acesso em: 02 fev. 2015.0040-4039http://www.repositorio.ufop.br/handle/123456789/4979https://doi.org/10.1016/j.tetlet.2011.05.039ark:/61566/0013000003g5zO periódico Tetrahedron Letters concede permissão para depósito deste artigo no Repositório Institucional da UFOP. Número da licença: 3581340458166.info:eu-repo/semantics/openAccessTaylor, Jason GuyRibeiro, Rodrigo da SilvaCorreia, Carlos Roque Duarteengreponame:Repositório Institucional da UFOPinstname:Universidade Federal de Ouro Preto (UFOP)instacron:UFOP2024-11-10T15:11:56Zoai:repositorio.ufop.br:123456789/4979Repositório InstitucionalPUBhttp://www.repositorio.ufop.br/oai/requestrepositorio@ufop.edu.bropendoar:32332024-11-10T15:11:56Repositório Institucional da UFOP - Universidade Federal de Ouro Preto (UFOP)false
dc.title.none.fl_str_mv Facile synthesis of symmetrical 3,3-diarylacrylates by a Heck-Matsuda reaction : an expedient route to biologically active indanones.
title Facile synthesis of symmetrical 3,3-diarylacrylates by a Heck-Matsuda reaction : an expedient route to biologically active indanones.
spellingShingle Facile synthesis of symmetrical 3,3-diarylacrylates by a Heck-Matsuda reaction : an expedient route to biologically active indanones.
Taylor, Jason Guy
Arenediazonium tetrafluoroborates
Heck-Matsuda
Arylation
Indanones
Palladium
title_short Facile synthesis of symmetrical 3,3-diarylacrylates by a Heck-Matsuda reaction : an expedient route to biologically active indanones.
title_full Facile synthesis of symmetrical 3,3-diarylacrylates by a Heck-Matsuda reaction : an expedient route to biologically active indanones.
title_fullStr Facile synthesis of symmetrical 3,3-diarylacrylates by a Heck-Matsuda reaction : an expedient route to biologically active indanones.
title_full_unstemmed Facile synthesis of symmetrical 3,3-diarylacrylates by a Heck-Matsuda reaction : an expedient route to biologically active indanones.
title_sort Facile synthesis of symmetrical 3,3-diarylacrylates by a Heck-Matsuda reaction : an expedient route to biologically active indanones.
author Taylor, Jason Guy
author_facet Taylor, Jason Guy
Ribeiro, Rodrigo da Silva
Correia, Carlos Roque Duarte
author_role author
author2 Ribeiro, Rodrigo da Silva
Correia, Carlos Roque Duarte
author2_role author
author
dc.contributor.author.fl_str_mv Taylor, Jason Guy
Ribeiro, Rodrigo da Silva
Correia, Carlos Roque Duarte
dc.subject.por.fl_str_mv Arenediazonium tetrafluoroborates
Heck-Matsuda
Arylation
Indanones
Palladium
topic Arenediazonium tetrafluoroborates
Heck-Matsuda
Arylation
Indanones
Palladium
description A simple and straightforward synthesis of symmetrical 3,3-diarylacrylates based on a Heck-Matsuda reaction of arenediazonium salts bearing electron-donating groups with methylacrylates is described. The reaction employs Pd(OAc)2 as catalyst and goes to completion within 1 h affording the corresponding unsaturated diaryl esters in good to high yields. This method permitted the expeditious and efficient synthesis of the anticancer 3-arylindanone 5 in two operative steps in 43% overall yield.
publishDate 2011
dc.date.none.fl_str_mv 2011
2015-04-09T11:00:01Z
2015-04-09T11:00:01Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv TAYLOR, J. G.; RIBEIRO, R. da S.; CORREIA, C. R. D. Facile synthesis of symmetrical 3,3-diarylacrylates by a Heck-Matsuda reaction: an expedient route to biologically active indanones. Tetrahedron Letters, v. 52, p. 3861-3864, 2011. Disponível em: <http://www.sciencedirect.com/science/article/pii/S0040403911007763>. Acesso em: 02 fev. 2015.
0040-4039
http://www.repositorio.ufop.br/handle/123456789/4979
https://doi.org/10.1016/j.tetlet.2011.05.039
dc.identifier.dark.fl_str_mv ark:/61566/0013000003g5z
identifier_str_mv TAYLOR, J. G.; RIBEIRO, R. da S.; CORREIA, C. R. D. Facile synthesis of symmetrical 3,3-diarylacrylates by a Heck-Matsuda reaction: an expedient route to biologically active indanones. Tetrahedron Letters, v. 52, p. 3861-3864, 2011. Disponível em: <http://www.sciencedirect.com/science/article/pii/S0040403911007763>. Acesso em: 02 fev. 2015.
0040-4039
ark:/61566/0013000003g5z
url http://www.repositorio.ufop.br/handle/123456789/4979
https://doi.org/10.1016/j.tetlet.2011.05.039
dc.language.iso.fl_str_mv eng
language eng
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:Repositório Institucional da UFOP
instname:Universidade Federal de Ouro Preto (UFOP)
instacron:UFOP
instname_str Universidade Federal de Ouro Preto (UFOP)
instacron_str UFOP
institution UFOP
reponame_str Repositório Institucional da UFOP
collection Repositório Institucional da UFOP
repository.name.fl_str_mv Repositório Institucional da UFOP - Universidade Federal de Ouro Preto (UFOP)
repository.mail.fl_str_mv repositorio@ufop.edu.br
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