Pd complexes based on phosphine-linked cyclophosphazenes: synthesis, characterization and application in Suzuki coupling reactions
Autor(a) principal: | |
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Data de Publicação: | 2012 |
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=S0103-50532012000200010 |
Resumo: | Palladium complexes were obtained by reaction of phosphine-linked cyclophosphazenes, (P3N3)(O-C6H4-PR2)6, where R = phenyl, i-propyl or cyclohexyl, with using a Pd/ligand molar ratio of 3/1. The (P3N3)(O-C6H4-PR2)6Pd3(dba)x complexes were characterized by elemental analyses, mass spectrometry, 31P NMR and FT-IR where a characteristic νC=C band of dba coordinated to palladium was always observed. All complexes were tested in Suzuki coupling reactions between phenylboronic acid and aryl halides. Turnover numbers as high as ca. 17,500 for the coupling of 2-bromotoluene with chlorophenylboronic acid could be obtained for R = cyclohexyl. The complex based on -PPh2 was also immobilized in silica matrixes by the sol-gel method. Preliminary experiments showed that the immobilized catalyst could be used in at least three consecutive Suzuki reactions with the same catalytic activity. |
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Pd complexes based on phosphine-linked cyclophosphazenes: synthesis, characterization and application in Suzuki coupling reactionscyclophosphazenespalladium complexesSuzuki coupling reactionscatalyst immobilizationPalladium complexes were obtained by reaction of phosphine-linked cyclophosphazenes, (P3N3)(O-C6H4-PR2)6, where R = phenyl, i-propyl or cyclohexyl, with using a Pd/ligand molar ratio of 3/1. The (P3N3)(O-C6H4-PR2)6Pd3(dba)x complexes were characterized by elemental analyses, mass spectrometry, 31P NMR and FT-IR where a characteristic νC=C band of dba coordinated to palladium was always observed. All complexes were tested in Suzuki coupling reactions between phenylboronic acid and aryl halides. Turnover numbers as high as ca. 17,500 for the coupling of 2-bromotoluene with chlorophenylboronic acid could be obtained for R = cyclohexyl. The complex based on -PPh2 was also immobilized in silica matrixes by the sol-gel method. Preliminary experiments showed that the immobilized catalyst could be used in at least three consecutive Suzuki reactions with the same catalytic activity.Sociedade Brasileira de Química2012-02-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532012000200010Journal of the Brazilian Chemical Society v.23 n.2 2012reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532012000200010info:eu-repo/semantics/openAccessPaula,Vanderlei I. deSato,Cintia A.Buffon,Reginaeng2012-03-02T00:00:00Zoai:scielo:S0103-50532012000200010Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2012-03-02T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Pd complexes based on phosphine-linked cyclophosphazenes: synthesis, characterization and application in Suzuki coupling reactions |
title |
Pd complexes based on phosphine-linked cyclophosphazenes: synthesis, characterization and application in Suzuki coupling reactions |
spellingShingle |
Pd complexes based on phosphine-linked cyclophosphazenes: synthesis, characterization and application in Suzuki coupling reactions Paula,Vanderlei I. de cyclophosphazenes palladium complexes Suzuki coupling reactions catalyst immobilization |
title_short |
Pd complexes based on phosphine-linked cyclophosphazenes: synthesis, characterization and application in Suzuki coupling reactions |
title_full |
Pd complexes based on phosphine-linked cyclophosphazenes: synthesis, characterization and application in Suzuki coupling reactions |
title_fullStr |
Pd complexes based on phosphine-linked cyclophosphazenes: synthesis, characterization and application in Suzuki coupling reactions |
title_full_unstemmed |
Pd complexes based on phosphine-linked cyclophosphazenes: synthesis, characterization and application in Suzuki coupling reactions |
title_sort |
Pd complexes based on phosphine-linked cyclophosphazenes: synthesis, characterization and application in Suzuki coupling reactions |
author |
Paula,Vanderlei I. de |
author_facet |
Paula,Vanderlei I. de Sato,Cintia A. Buffon,Regina |
author_role |
author |
author2 |
Sato,Cintia A. Buffon,Regina |
author2_role |
author author |
dc.contributor.author.fl_str_mv |
Paula,Vanderlei I. de Sato,Cintia A. Buffon,Regina |
dc.subject.por.fl_str_mv |
cyclophosphazenes palladium complexes Suzuki coupling reactions catalyst immobilization |
topic |
cyclophosphazenes palladium complexes Suzuki coupling reactions catalyst immobilization |
description |
Palladium complexes were obtained by reaction of phosphine-linked cyclophosphazenes, (P3N3)(O-C6H4-PR2)6, where R = phenyl, i-propyl or cyclohexyl, with using a Pd/ligand molar ratio of 3/1. The (P3N3)(O-C6H4-PR2)6Pd3(dba)x complexes were characterized by elemental analyses, mass spectrometry, 31P NMR and FT-IR where a characteristic νC=C band of dba coordinated to palladium was always observed. All complexes were tested in Suzuki coupling reactions between phenylboronic acid and aryl halides. Turnover numbers as high as ca. 17,500 for the coupling of 2-bromotoluene with chlorophenylboronic acid could be obtained for R = cyclohexyl. The complex based on -PPh2 was also immobilized in silica matrixes by the sol-gel method. Preliminary experiments showed that the immobilized catalyst could be used in at least three consecutive Suzuki reactions with the same catalytic activity. |
publishDate |
2012 |
dc.date.none.fl_str_mv |
2012-02-01 |
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=S0103-50532012000200010 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532012000200010 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.1590/S0103-50532012000200010 |
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.23 n.2 2012 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_ |
1750318173086810112 |