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NiII, CuII and ZnII complexes with a sterically hindered scorpionate ligand (TpmsPh) and catalytic application in the diasteroselective nitroaldol (Henry) reaction

2014-10-28Journal article Restricted access
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dc.contributor.authorRocha, Bruno G. M.
dc.contributor.authorMacLeod, Tatiana C. O.
dc.contributor.authorGuedes Da Silva, M. Fátima C.
dc.contributor.authorLuzyanin, Konstantin V.
dc.contributor.authorMartins, Luisa
dc.contributor.authorPombeiro, Armando
dc.date.accessioned2015-08-24T13:38:38Z
dc.date.available2015-08-24T13:38:38Z
dc.date.issued2014-10-28
dc.description.abstractThe Ni-II and Zn-II complexes [MCl(Tpms(Ph))] (Tpms(Ph) = SO3C(pz(Ph))(3), pz = pyrazolyl; M = Ni 2 or Zn 3) and the Cu-II complex [CuCl(Tpms(Ph))(H2O)] (4) have been prepared by treatment of the lithium salt of the sterically demanding and coordination flexible tris(3-phenyl-1-pyrazolyl)methanesulfonate (Tpms(Ph))(-) (1) with the respective metal chlorides. The (Tpms(Ph))(-) ligand shows the N-3 or N2O coordination modes in 2 and 3 or in 4, respectively. Upon reaction of 2 and 3 with Ag(CF3SO3) in acetonitrile the complexes [M(Tpms(Ph))-(MeCN)](CF3SO3) (M = Ni 5 or Zn 6, respectively) were formed. The compounds were obtained in good yields and characterized by analytic and spectral (IR, H-1 and C-13{H-1} NMR, ESI-MS) data, density functional theory (DFT) methods and {for 4 and [(Bu4N)-Bu-n](Tpms(Ph)) (7), the tatter obtained upon Li+ replacement by [(Bu4N)-Bu-n](+) in Li(Tpms(Ph))} by single crystal X-ray diffraction analysis. The Zn-II and Cu-II complexes (3 and 4, respectively) act as efficient catalyst precursors for the diastereoselective nitroaldol reaction of benzaldehydes and nitroethane to the corresponding beta-nitroalkanols (up to 99% yield, at room temperature) with diastereoselectivity towards the formation of the anti isomer, whereas the Ni-II complex 2 only shows a modest catalytic activity.por
dc.identifier.citationROCHA, Bruno G. M.; [et al] – NiII, CuII and ZnII Complexes with a sterically hindered scorpionate ligand (TpmsPh) and catalytic application in the diasteroselective Nitroaldol (Henry) reaction. Dalton Transactions. ISSN: 1477-9226. Vol. 43, nr. 40 (2104), pp. 15192-15200por
dc.identifier.doi10.1039/c4dt01509f
dc.identifier.issn1477-9226
dc.identifier.issn1477-9234
dc.identifier.urihttp://hdl.handle.net/10400.21/4955
dc.language.isoengpor
dc.peerreviewedyespor
dc.publisherRoyal Society of Chemistrypor
dc.relation.publisherversionhttp://pubs.rsc.org/en/content/articlepdf/2014/dt/c4dt01509f
dc.subjectMolecular-Orbital Methodspor
dc.subjectValence Basis-Setspor
dc.subjectExtended Basis-Setspor
dc.subjectGaussin-Type Basispor
dc.subjectCyclohexane Oxidationpor
dc.subjectRhenium Complexespor
dc.subjectDiastereoselective Synthesispor
dc.subjectStructural-Characterizationpor
dc.subjectOrganometallic Compoundspor
dc.subjectPeroxidative Oxidationpor
dc.titleNiII, CuII and ZnII complexes with a sterically hindered scorpionate ligand (TpmsPh) and catalytic application in the diasteroselective nitroaldol (Henry) reactionpor
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage15200por
oaire.citation.issue40por
oaire.citation.startPage15192por
oaire.citation.titleDalton Transactionspor
oaire.citation.volume43por
person.familyNameGuedes da Silva
person.familyNameMartins
person.familyNamePombeiro
person.givenNameM. Fátima C.
person.givenNameLuisa
person.givenNameArmando
person.identifier789079
person.identifier637885
person.identifier.ciencia-id7619-8E8E-979A
person.identifier.ciencia-idE218-E297-A4EA
person.identifier.ciencia-id8311-38FA-CEFB
person.identifier.orcid0000-0003-4836-2409
person.identifier.orcid0000-0002-5403-9352
person.identifier.orcid0000-0001-8323-888X
person.identifier.ridH-8274-2012
person.identifier.ridG-6210-2011
person.identifier.ridI-5945-2012
person.identifier.scopus-author-id6701761571
person.identifier.scopus-author-id8650947800
person.identifier.scopus-author-id7006067269
rcaap.rightsclosedAccesspor
rcaap.typearticlepor
relation.isAuthorOfPublication18e14ad3-9937-46d0-83b2-36fab224c1c0
relation.isAuthorOfPublication8ed70b09-b4d3-4a5d-9f75-12b13a332204
relation.isAuthorOfPublication6d18ff2e-5c33-4010-b1e7-964c72349813
relation.isAuthorOfPublication.latestForDiscovery6d18ff2e-5c33-4010-b1e7-964c72349813

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