Synthesis, stability, and (de)hydrogenation catalysis by normal and abnormal alkene- and picolyl-tethered NHC ruthenium complexes

dc.contributor.authorMalan, F.P. (Frederick)
dc.contributor.authorSingleton, Eric
dc.contributor.authorVan Rooyen, Petrus H.
dc.contributor.authorAlbrecht, Martin
dc.contributor.authorLandman, Marile
dc.contributor.emailmarile.landman@up.ac.zaen_ZA
dc.date.accessioned2019-07-15T14:50:19Z
dc.date.issued2019-06
dc.description.abstractA series of p-cymene and cyclopentadienyl Ru(II)-aNHC complexes were synthesized from 2-methylimidazolium salts with either an N-bound alkenyl (1, 3) or picolyl tether (6, 7). The C(5)-Me substituted alkenyl-tethered analogues (2, 4) were also synthesized. Ag-mediated C(2)-dealkylation was a prominent side reaction that led to the formation of normally bound NHC Ru(II) complexes, which in selected cases were isolated (5, 8). A C(4)- over C(2)-selectivity for ruthenium binding was established by protecting the C(2)-position with an iPr group on the imidazolium precursor, for which unique p-cymene (9) and cyclopentadienyl (10) Ru(II)-aNHC derivatives were synthesized. All complexes were applied in the transfer hydrogenation of ketones and in secondary alcohol oxidation, with higher catalytic activity for the p-cymene over the cyclopentadienyl systems, as well as the alkenyl- over the picolyl-containing aNHC complexes.en_ZA
dc.description.departmentChemistryen_ZA
dc.description.embargo2020-06-22
dc.description.librarianhj2019en_ZA
dc.description.sponsorshipThe South African National Research Foundation (ML Grant nr. 93638, FPM Grant nr. 88594), the Central Research Fund of the University of Pretoria (ML) and the European Research Council (MA, CoG 615653).en_ZA
dc.description.urihttp://pubs.acs.org/journal/orgnd7en_ZA
dc.identifier.citationMalan, F.P., Singleton, E., Van Rooyen, P.H. et al. Synthesis, stability, and (de)hydrogenation catalysis by normal and abnormal alkene- and picolyl-tethered NHC ruthenium complexes. Organometallics (2019) 38(13):2624-2635.en_ZA
dc.identifier.issn0276-7333 (print)
dc.identifier.issn1520-6041 (online)
dc.identifier.other10.1021/acs.organomet.9b00178
dc.identifier.urihttp://hdl.handle.net/2263/70719
dc.language.isoenen_ZA
dc.publisherAmerican Chemical Societyen_ZA
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in Organometallics, © 2019 American Chemical Society after peer review and technical editing by the publisher.en_ZA
dc.subjectN-Heterocyclic carbenes (NHCs)en_ZA
dc.subjectRuthenium complexesen_ZA
dc.subjectSynthesisen_ZA
dc.subjectStabilityen_ZA
dc.subject(De)hyrogenationen_ZA
dc.titleSynthesis, stability, and (de)hydrogenation catalysis by normal and abnormal alkene- and picolyl-tethered NHC ruthenium complexesen_ZA
dc.typePostprint Articleen_ZA

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