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A tunable family of CAAC-ruthenium olefin metathesis catalysts modularly derived from a large-scale produced ibuprofen intermediate

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dc.abstract.enA series of tunable CAAC-based ruthenium benzylidene complexes with increased lipophilicity derived from a ketone being a large-scale produced key substrate for a popular nonsteroidal anti-inflammatory drug—ibuprofen was obtained and tested in various olefin metathesis transformations. As a group, these catalysts exhibited higher activity than their known analogues containing a smaller and less lipophilic phenyl substituent on the α-carbon atom, but in individual reactions, the size of the N-aryl moiety was revealed as a decisive factor. For example, in the cross-metathesis of methyl oleate with ethylene (ethenolysis)—a reaction with growing industrial potential—the best results were obtained when the N-aryl contained an isopropyl or tert-butyl substituent in the ortho position. At the same time, in the RCM, CM, and self-CM transformations involving larger olefinic substrates, the catalysts with smaller aryl-bearing CAAC ligands, where methyl and ethyl groups occupy ortho, ortho’ positions performed better. This offers a great deal of tunability and allows for selection of the best catalyst for a given reaction while keeping the general structure (and manufacturing method) of the ibuprofen-intermediate derived CAAC ligand the same
dc.affiliationUniwersytet Warszawski
dc.contributor.authorKajetanowicz, Anna
dc.contributor.authorGrela, Karol
dc.contributor.authorStruzik, Filip
dc.contributor.authorSytniczuk, Adrian
dc.date.accessioned2024-01-24T18:13:46Z
dc.date.available2024-01-24T18:13:46Z
dc.date.copyright2023-09-22
dc.date.issued2023
dc.description.accesstimeAT_PUBLICATION
dc.description.financeNie dotyczy
dc.description.number39
dc.description.versionFINAL_PUBLISHED
dc.description.volume14
dc.identifier.doi10.1039/D3SC03849A
dc.identifier.issn2041-6520
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/101917
dc.identifier.weblinkhttp://pubs.rsc.org/en/content/articlepdf/2023/SC/D3SC03849A
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofChemical Science
dc.relation.pages10744-10755
dc.rightsCC-BY
dc.sciencecloudnosend
dc.titleA tunable family of CAAC-ruthenium olefin metathesis catalysts modularly derived from a large-scale produced ibuprofen intermediate
dc.typeJournalArticle
dspace.entity.typePublication