Pd-catalyzed Suzuki cross-Coupling reaction of bromostilbene: insights on the nature of the boron Species

Detalhes bibliográficos
Autor(a) principal: Nunes,Carolina M.
Data de Publicação: 2007
Outros Autores: Monteiro,Adriano L.
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=S0103-50532007000700021
Resumo: Arylboronate esters and arylborate salts can be used as partner for the Suzuki reaction of (E)-bromostilbene in the presence of Pd(OAc)2/PPh3 as catalyst precursor. While KOH is necessary for the coupling reaction with arylboronic acids and pinacol esters, aryl borate sodium salt can be used in a base-free protocol. The comparison between the three organoboron compounds using competitive experiments and electrospray ionization mass spectrometry analysis supports the proposition that the base initially reacts with the arylboronic acid or ester to form an arylborate species which undergoes the transmetallation process with the palladium catalyst.
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spelling Pd-catalyzed Suzuki cross-Coupling reaction of bromostilbene: insights on the nature of the boron Speciescross-coupling reactionsSuzuki reactionpalladiumESIorganoboron speciesArylboronate esters and arylborate salts can be used as partner for the Suzuki reaction of (E)-bromostilbene in the presence of Pd(OAc)2/PPh3 as catalyst precursor. While KOH is necessary for the coupling reaction with arylboronic acids and pinacol esters, aryl borate sodium salt can be used in a base-free protocol. The comparison between the three organoboron compounds using competitive experiments and electrospray ionization mass spectrometry analysis supports the proposition that the base initially reacts with the arylboronic acid or ester to form an arylborate species which undergoes the transmetallation process with the palladium catalyst.Sociedade Brasileira de Química2007-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532007000700021Journal of the Brazilian Chemical Society v.18 n.7 2007reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532007000700021info:eu-repo/semantics/openAccessNunes,Carolina M.Monteiro,Adriano L.eng2008-01-08T00:00:00Zoai:scielo:S0103-50532007000700021Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2008-01-08T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Pd-catalyzed Suzuki cross-Coupling reaction of bromostilbene: insights on the nature of the boron Species
title Pd-catalyzed Suzuki cross-Coupling reaction of bromostilbene: insights on the nature of the boron Species
spellingShingle Pd-catalyzed Suzuki cross-Coupling reaction of bromostilbene: insights on the nature of the boron Species
Nunes,Carolina M.
cross-coupling reactions
Suzuki reaction
palladium
ESI
organoboron species
title_short Pd-catalyzed Suzuki cross-Coupling reaction of bromostilbene: insights on the nature of the boron Species
title_full Pd-catalyzed Suzuki cross-Coupling reaction of bromostilbene: insights on the nature of the boron Species
title_fullStr Pd-catalyzed Suzuki cross-Coupling reaction of bromostilbene: insights on the nature of the boron Species
title_full_unstemmed Pd-catalyzed Suzuki cross-Coupling reaction of bromostilbene: insights on the nature of the boron Species
title_sort Pd-catalyzed Suzuki cross-Coupling reaction of bromostilbene: insights on the nature of the boron Species
author Nunes,Carolina M.
author_facet Nunes,Carolina M.
Monteiro,Adriano L.
author_role author
author2 Monteiro,Adriano L.
author2_role author
dc.contributor.author.fl_str_mv Nunes,Carolina M.
Monteiro,Adriano L.
dc.subject.por.fl_str_mv cross-coupling reactions
Suzuki reaction
palladium
ESI
organoboron species
topic cross-coupling reactions
Suzuki reaction
palladium
ESI
organoboron species
description Arylboronate esters and arylborate salts can be used as partner for the Suzuki reaction of (E)-bromostilbene in the presence of Pd(OAc)2/PPh3 as catalyst precursor. While KOH is necessary for the coupling reaction with arylboronic acids and pinacol esters, aryl borate sodium salt can be used in a base-free protocol. The comparison between the three organoboron compounds using competitive experiments and electrospray ionization mass spectrometry analysis supports the proposition that the base initially reacts with the arylboronic acid or ester to form an arylborate species which undergoes the transmetallation process with the palladium catalyst.
publishDate 2007
dc.date.none.fl_str_mv 2007-01-01
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=S0103-50532007000700021
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532007000700021
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532007000700021
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.18 n.7 2007
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
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