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dc.contributor.authorPoater, Albert
dc.contributor.authorCavallo, Luigi
dc.date.accessioned2015-10-04T12:14:01Z
dc.date.available2015-10-04T12:14:01Z
dc.date.issued2015-09-29
dc.identifier.citationA comprehensive study of olefin metathesis catalyzed by Ru-based catalysts 2015, 11:1767 Beilstein Journal of Organic Chemistry
dc.identifier.issn1860-5397
dc.identifier.pmid26664596
dc.identifier.doi10.3762/bjoc.11.192
dc.identifier.urihttp://hdl.handle.net/10754/579154
dc.description.abstractDuring a Ru-catalyzed reaction of an olefin with an alkylidene moiety that leads to a metallacycle intermediate, the cis insertion of the olefin can occur from two different directions, namely side and bottom with respect to the phosphine or N-heterocyclic ligand (NHC), depending on the first or second generation Grubbs catalyst. Here, DFT calculations unravel to which extent the bottom coordination of olefins with respect is favored over the side coordination through screening a wide range of catalysts, including first and second generation Grubbs catalysts as well as the subsequent Hoveyda derivatives. The equilibrium between bottom and side coordination is influenced by sterics, electronics, and polarity of the solvent. The side attack is favored for sterically less demanding NHC and/or alkylidene ligands. Moreover the generation of a 14-electron species is also discussed, with either pyridine or phosphine ligands to dissociate.
dc.language.isoen
dc.publisherBeilstein Institut
dc.relation.urlhttp://www.beilstein-journals.org/bjoc/content/11/1/192
dc.rightsThis is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)
dc.subjectcis
dc.subjectdensity functional theory (DFT)
dc.subjectN-heterocyclic carbene
dc.subjectolefin metathesis
dc.subjectruthenium
dc.titleA comprehensive study of olefin metathesis catalyzed by Ru-based catalysts
dc.typeArticle
dc.contributor.departmentChemical Science Program
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalBeilstein Journal of Organic Chemistry
dc.eprint.versionPublisher's Version/PDF
dc.contributor.institutionInstitut de Química Computacional i Catàlisi and Departament de Química, Universitat de Girona, Campus Montilivi, 17071 Girona, Catalonia, Spain
dc.contributor.affiliationKing Abdullah University of Science and Technology (KAUST)
kaust.personCavallo, Luigi
refterms.dateFOA2018-06-13T10:29:37Z


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