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Article: Polystyrene-supported triphenylarsines: Useful ligands in palladium-catalyzed aryl halide homocoupling reactions and a catalyst for alkene epoxidation using hydrogen peroxide

TitlePolystyrene-supported triphenylarsines: Useful ligands in palladium-catalyzed aryl halide homocoupling reactions and a catalyst for alkene epoxidation using hydrogen peroxide
Authors
KeywordsEpoxidation
Homocoupling
Hydrogen peroxide
Suzuki-Miyaura coupling
Triphenylarsine reagents
Issue Date2005
PublisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/tet
Citation
Tetrahedron, 2005, v. 61 n. 51, p. 12053-12057 How to Cite?
AbstractThe utility of both soluble (non-cross-linked) and insoluble (cross-linked) polystyrene-supported triphenylarsine reagents were examined. These reagents were prepared by standard radical polymerization methodology and used in palladium-catalyzed homocoupling reactions of aryl halides. The insoluble reagent was also used as a catalyst precursor in heterogeneous alkene epoxidation reactions in which aqueous hydrogen peroxide was the stoichiometric oxidant. For the aryl halide homocoupling reactions, both reagents worked well and afforded similar results. Unhindered aryl iodides afforded the best yields in the shortest reaction times compared to aryl bromides. The epoxidation reactions of unfunctionalized alkenes were not very efficient. This was probably due to the hydrophobicity of the polystyrene matrix, which did not swell in the reaction medium. Thus, since a microporous, gel-type polystyrene matrix was used, the majority of the arsine groups were inaccessible to the reaction components and therefore incapable of participating in catalysis. © 2005 Elsevier Ltd. All rights reserved.
Persistent Identifierhttp://hdl.handle.net/10722/54256
ISSN
2015 Impact Factor: 2.645
2015 SCImago Journal Rankings: 0.991
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorSong He, Hen_HK
dc.contributor.authorZhang, Cen_HK
dc.contributor.authorNg, CKWen_HK
dc.contributor.authorToy, PHen_HK
dc.date.accessioned2009-04-03T07:41:18Z-
dc.date.available2009-04-03T07:41:18Z-
dc.date.issued2005en_HK
dc.identifier.citationTetrahedron, 2005, v. 61 n. 51, p. 12053-12057en_HK
dc.identifier.issn0040-4020en_HK
dc.identifier.urihttp://hdl.handle.net/10722/54256-
dc.description.abstractThe utility of both soluble (non-cross-linked) and insoluble (cross-linked) polystyrene-supported triphenylarsine reagents were examined. These reagents were prepared by standard radical polymerization methodology and used in palladium-catalyzed homocoupling reactions of aryl halides. The insoluble reagent was also used as a catalyst precursor in heterogeneous alkene epoxidation reactions in which aqueous hydrogen peroxide was the stoichiometric oxidant. For the aryl halide homocoupling reactions, both reagents worked well and afforded similar results. Unhindered aryl iodides afforded the best yields in the shortest reaction times compared to aryl bromides. The epoxidation reactions of unfunctionalized alkenes were not very efficient. This was probably due to the hydrophobicity of the polystyrene matrix, which did not swell in the reaction medium. Thus, since a microporous, gel-type polystyrene matrix was used, the majority of the arsine groups were inaccessible to the reaction components and therefore incapable of participating in catalysis. © 2005 Elsevier Ltd. All rights reserved.en_HK
dc.languageengen_HK
dc.publisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/teten_HK
dc.relation.ispartofTetrahedronen_HK
dc.rightsCreative Commons: Attribution 3.0 Hong Kong License-
dc.subjectEpoxidationen_HK
dc.subjectHomocouplingen_HK
dc.subjectHydrogen peroxideen_HK
dc.subjectSuzuki-Miyaura couplingen_HK
dc.subjectTriphenylarsine reagentsen_HK
dc.titlePolystyrene-supported triphenylarsines: Useful ligands in palladium-catalyzed aryl halide homocoupling reactions and a catalyst for alkene epoxidation using hydrogen peroxideen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0040-4020&volume=61&issue=51&spage=12053&epage=12057&date=2005&atitle=Polystyrene-supported+triphenylarsines:+useful+ligands+in+palladium-catalyzed+aryl+halide+homocoupling+reactions+and+a+catalyst+for+alkene+epoxidation+using+hydrogen+peroxideen_HK
dc.identifier.emailToy, PH:phtoy@hkucc.hku.hken_HK
dc.identifier.authorityToy, PH=rp00791en_HK
dc.description.naturepostprinten_HK
dc.identifier.doi10.1016/j.tet.2005.07.108en_HK
dc.identifier.scopuseid_2-s2.0-27944458847en_HK
dc.identifier.hkuros117920-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-27944458847&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume61en_HK
dc.identifier.issue51en_HK
dc.identifier.spage12053en_HK
dc.identifier.epage12057en_HK
dc.identifier.isiWOS:000233784300005-
dc.publisher.placeUnited Kingdomen_HK
dc.identifier.scopusauthoridSong He, H=9332489600en_HK
dc.identifier.scopusauthoridZhang, C=7405490646en_HK
dc.identifier.scopusauthoridNg, CKW=36747480200en_HK
dc.identifier.scopusauthoridToy, PH=7006579247en_HK

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