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Large‐Scale Synthesis of a Niche Olefin Metathesis Catalyst Bearing an Unsymmetrical N‐Heterocyclic Carbene (NHC) Ligand and its Application in a Green Pharmaceutical Context

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cris.lastimport.scopus2024-02-12T20:35:22Z
dc.abstract.enA large-scale synthesis of known Ru olefin metathesis catalyst VII featuring an unsymmetrical N-heterocyclic carbene (NHC) ligand with one 2,5-diisopropylphenyl (DIPP) and one thiophenylmethylene N-substituent is reported. The optimised procedure does not require column chromatography in any step and allows for preparation of up to 0.5 kg batches of the catalyst from simple precursors. The application profile of the obtained catalyst was studied in environmentally friendly dimethyl carbonate (DMC). Although VII exhibited low efficiency in cross-metathesis (CM) with electron-deficient partners, good to excellent results were noted for substrates featuring easy to isomerise C−C double bonds. This includes polyfunctional substrates of medicinal chemistry interest, such as analogues of psychoactive 5F-PB-22 and NM-2201 and two PDE5 inhibitors—Sildenafil and Vardenafil. Finally, a larger scale ring-closing metathesis (RCM) of a Vardenafil derivative was conducted in DMC, allowing for straightforward isolation of the expected product (23 g) in high yield and with low Ru contamination level (7.7 ppm).
dc.affiliationUniwersytet Warszawski
dc.contributor.authorCzarnocki, Stefan
dc.contributor.authorMałecki, Paweł
dc.contributor.authorSzczepanik, Paweł
dc.contributor.authorNienałtowski, Tomasz
dc.contributor.authorPawłowska, Jolanta
dc.contributor.authorKajetanowicz, Anna
dc.contributor.authorGrela, Karol
dc.contributor.authorCzajkowska‐Szczykowska, Dorota
dc.date.accessioned2024-01-25T04:59:31Z
dc.date.available2024-01-25T04:59:31Z
dc.date.issued2020
dc.description.financePublikacja bezkosztowa
dc.description.number67
dc.description.volume26
dc.identifier.doi10.1002/CHEM.202003830
dc.identifier.issn0947-6539
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/110875
dc.identifier.weblinkhttps://onlinelibrary.wiley.com/doi/pdf/10.1002/chem.202003830
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofChemistry - A European Journal
dc.relation.pages15708-15717
dc.rightsClosedAccess
dc.sciencecloudnosend
dc.titleLarge‐Scale Synthesis of a Niche Olefin Metathesis Catalyst Bearing an Unsymmetrical N‐Heterocyclic Carbene (NHC) Ligand and its Application in a Green Pharmaceutical Context
dc.typeJournalArticle
dspace.entity.typePublication