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dc.contributor.authorOberholzer, Miriam-
dc.contributor.authorFrech Nabold, Christian M.-
dc.date.accessioned2018-08-23T13:40:06Z-
dc.date.available2018-08-23T13:40:06Z-
dc.date.issued2013-
dc.identifier.issn1463-9262de_CH
dc.identifier.issn1463-9270de_CH
dc.identifier.urihttps://digitalcollection.zhaw.ch/handle/11475/9481-
dc.description.abstractDichloro-bis(aminophosphine) complexes of palladium with the general formula [(P{(NC5H10)3−n(C6H11)n})2Pd(Cl)2] (where n=0-2) are easily accessible, cheap and air stable, highly active and universally applicable C–C cross-coupling catalysts, which exhibit an excellent functional group tolerance. The ligand composition of amine-substituted phosphines (controlled by the number of P–N bonds) was found to effectively determine their catalytic activity in the Heck reaction, for which nanoparticles were demonstrated to be their catalytically active form. While dichloro{bis[1,1′,1′′-(phosphinetriyl)tripiperidine]}palladium (1), the least stable complex (towards protons) within the series of [(P{(NC5H10)3−n(C6H11)n})2Pd(Cl)2] (where n=0-3), is a highly active Heck catalyst at 100°C and, hence, a rare example of an effective and versatile Heck catalyst that efficiently operates under mild reaction conditions (100 °C or below), a significant successive drop in activity was noticed for dichloro-bis(1,1′-(cyclohexylphosphinediyl)dipiperidine)palladium (2, with n=1), dichloro-bis(1-(dicyclohexylphosphinyl)piperidine)palladium (3, with n=2) and dichloro-bis(tricyclohexylphosphine)palladium (4, with n=3), of which the latter is essentially inactive (at least under the reaction conditions applied). This trend was explained by the successively increasing complex stability and its ensuing retarding effect on the (water-induced) generation of palladium nanoparticles thereof. This interpretation was experimentally confirmed (initial reductions of 1-4 into palladium(0) complexes of the type [Pd(P{(NC5H10)3−n(C6H11)n})2] (where n=0-3) were excluded to be the reason for the activity difference observed as well as molecular (Pd0/PdII) mechanisms were excluded to be operative) and thus demonstrates that the catalytic activity of dichloro-bis(aminophosphine) complexes of palladium can – in reactions where nanoparticles are involved – effectively be controlled by the number of P–N bonds in the ligand system.de_CH
dc.language.isoende_CH
dc.publisherRoyal Society of Chemistryde_CH
dc.relation.ispartofGreen Chemistryde_CH
dc.rightsLicence according to publishing contractde_CH
dc.subject.ddc540: Chemiede_CH
dc.titleMizoroki–Heck reactions catalyzed by palladium dichloro-bis(aminophosphine) complexes under mild reaction conditions : the importance of ligand composition on the catalytic activityde_CH
dc.typeBeitrag in wissenschaftlicher Zeitschriftde_CH
dcterms.typeTextde_CH
zhaw.departementLife Sciences und Facility Managementde_CH
dc.identifier.doi10.1039/c3gc40493ede_CH
zhaw.funding.euNode_CH
zhaw.issue6de_CH
zhaw.originated.zhawYesde_CH
zhaw.pages.end1686de_CH
zhaw.pages.start1678de_CH
zhaw.publication.statuspublishedVersionde_CH
zhaw.volume2013de_CH
zhaw.publication.reviewPeer review (Publikation)de_CH
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Oberholzer, M., & Frech Nabold, C. M. (2013). Mizoroki–Heck reactions catalyzed by palladium dichloro-bis(aminophosphine) complexes under mild reaction conditions : the importance of ligand composition on the catalytic activity. Green Chemistry, 2013(6), 1678–1686. https://doi.org/10.1039/c3gc40493e
Oberholzer, M. and Frech Nabold, C.M. (2013) ‘Mizoroki–Heck reactions catalyzed by palladium dichloro-bis(aminophosphine) complexes under mild reaction conditions : the importance of ligand composition on the catalytic activity’, Green Chemistry, 2013(6), pp. 1678–1686. Available at: https://doi.org/10.1039/c3gc40493e.
M. Oberholzer and C. M. Frech Nabold, “Mizoroki–Heck reactions catalyzed by palladium dichloro-bis(aminophosphine) complexes under mild reaction conditions : the importance of ligand composition on the catalytic activity,” Green Chemistry, vol. 2013, no. 6, pp. 1678–1686, 2013, doi: 10.1039/c3gc40493e.
OBERHOLZER, Miriam und Christian M. FRECH NABOLD, 2013. Mizoroki–Heck reactions catalyzed by palladium dichloro-bis(aminophosphine) complexes under mild reaction conditions : the importance of ligand composition on the catalytic activity. Green Chemistry. 2013. Bd. 2013, Nr. 6, S. 1678–1686. DOI 10.1039/c3gc40493e
Oberholzer, Miriam, and Christian M. Frech Nabold. 2013. “Mizoroki–Heck Reactions Catalyzed by Palladium Dichloro-Bis(aminophosphine) Complexes under Mild Reaction Conditions : The Importance of Ligand Composition on the Catalytic Activity.” Green Chemistry 2013 (6): 1678–86. https://doi.org/10.1039/c3gc40493e.
Oberholzer, Miriam, and Christian M. Frech Nabold. “Mizoroki–Heck Reactions Catalyzed by Palladium Dichloro-Bis(aminophosphine) Complexes under Mild Reaction Conditions : The Importance of Ligand Composition on the Catalytic Activity.” Green Chemistry, vol. 2013, no. 6, 2013, pp. 1678–86, https://doi.org/10.1039/c3gc40493e.


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