Palladium-catalyzed arylation of enoates with iodobenzene: stereoselective synthesis of trisubstituted olefins
Autor(a) principal: | |
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Data de Publicação: | 2013 |
Outros Autores: | , , , , |
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. |
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Journal of the Brazilian Chemical Society (Online) |
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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 |