Palladium-catalyzed arylation of enoates with iodobenzene: stereoselective synthesis of trisubstituted olefins

Detalhes bibliográficos
Autor(a) principal: Fernandes,Talita de A.
Data de Publicação: 2013
Outros Autores: Vaz,Boniek G., Silva,Alcides J. M. da, Esteves,Pierre M., Eberlin,Marcos N., Costa,Paulo R. R.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013000300018
Resumo: The Heck reaction between E- and Z-enoates and iodobenzene was studied in the presence of Pd(OAc)2. The stereochemistry in resulting adducts was dependent on the enoate geometry (stereospecific reaction). Best yields were obtained from Z-isomers in acetone using Ag2CO3 as base. The main cationic palladium intermediates possibly involved in the catalytic cycle could be intercepted and characterized by electrospray ionization mass spectrometry (ESI-MS). The stereoselectivity observed was rationalized through the classic mechanism of the Heck reaction.
id SBQ-2_69e815624e9fe660bda3df804eacff03
oai_identifier_str oai:scielo:S0103-50532013000300018
network_acronym_str SBQ-2
network_name_str Journal of the Brazilian Chemical Society (Online)
repository_id_str
spelling Palladium-catalyzed arylation of enoates with iodobenzene: stereoselective synthesis of trisubstituted olefinsHeck reactionenoatespalladium catalysismass spectrometryThe Heck reaction between E- and Z-enoates and iodobenzene was studied in the presence of Pd(OAc)2. The stereochemistry in resulting adducts was dependent on the enoate geometry (stereospecific reaction). Best yields were obtained from Z-isomers in acetone using Ag2CO3 as base. The main cationic palladium intermediates possibly involved in the catalytic cycle could be intercepted and characterized by electrospray ionization mass spectrometry (ESI-MS). The stereoselectivity observed was rationalized through the classic mechanism of the Heck reaction.Sociedade Brasileira de Química2013-03-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013000300018Journal of the Brazilian Chemical Society v.24 n.3 2013reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20130067info:eu-repo/semantics/openAccessFernandes,Talita de A.Vaz,Boniek G.Silva,Alcides J. M. daEsteves,Pierre M.Eberlin,Marcos N.Costa,Paulo R. R.eng2013-05-24T00:00:00Zoai:scielo:S0103-50532013000300018Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2013-05-24T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Palladium-catalyzed arylation of enoates with iodobenzene: stereoselective synthesis of trisubstituted olefins
title Palladium-catalyzed arylation of enoates with iodobenzene: stereoselective synthesis of trisubstituted olefins
spellingShingle Palladium-catalyzed arylation of enoates with iodobenzene: stereoselective synthesis of trisubstituted olefins
Fernandes,Talita de A.
Heck reaction
enoates
palladium catalysis
mass spectrometry
title_short Palladium-catalyzed arylation of enoates with iodobenzene: stereoselective synthesis of trisubstituted olefins
title_full Palladium-catalyzed arylation of enoates with iodobenzene: stereoselective synthesis of trisubstituted olefins
title_fullStr Palladium-catalyzed arylation of enoates with iodobenzene: stereoselective synthesis of trisubstituted olefins
title_full_unstemmed Palladium-catalyzed arylation of enoates with iodobenzene: stereoselective synthesis of trisubstituted olefins
title_sort Palladium-catalyzed arylation of enoates with iodobenzene: stereoselective synthesis of trisubstituted olefins
author Fernandes,Talita de A.
author_facet Fernandes,Talita de A.
Vaz,Boniek G.
Silva,Alcides J. M. da
Esteves,Pierre M.
Eberlin,Marcos N.
Costa,Paulo R. R.
author_role author
author2 Vaz,Boniek G.
Silva,Alcides J. M. da
Esteves,Pierre M.
Eberlin,Marcos N.
Costa,Paulo R. R.
author2_role author
author
author
author
author
dc.contributor.author.fl_str_mv Fernandes,Talita de A.
Vaz,Boniek G.
Silva,Alcides J. M. da
Esteves,Pierre M.
Eberlin,Marcos N.
Costa,Paulo R. R.
dc.subject.por.fl_str_mv Heck reaction
enoates
palladium catalysis
mass spectrometry
topic Heck reaction
enoates
palladium catalysis
mass spectrometry
description The Heck reaction between E- and Z-enoates and iodobenzene was studied in the presence of Pd(OAc)2. The stereochemistry in resulting adducts was dependent on the enoate geometry (stereospecific reaction). Best yields were obtained from Z-isomers in acetone using Ag2CO3 as base. The main cationic palladium intermediates possibly involved in the catalytic cycle could be intercepted and characterized by electrospray ionization mass spectrometry (ESI-MS). The stereoselectivity observed was rationalized through the classic mechanism of the Heck reaction.
publishDate 2013
dc.date.none.fl_str_mv 2013-03-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013000300018
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013000300018
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.5935/0103-5053.20130067
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Journal of the Brazilian Chemical Society v.24 n.3 2013
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
instacron:SBQ
instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
institution SBQ
reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
repository.mail.fl_str_mv ||office@jbcs.sbq.org.br
_version_ 1750318174800183296

Registros relacionados