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A tunable family of CAAC-ruthenium olefin metathesis catalysts modularly derived from a large-scale produced ibuprofen intermediate
A 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, t...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10566500/ https://www.ncbi.nlm.nih.gov/pubmed/37829018 http://dx.doi.org/10.1039/d3sc03849a |
Sumario: | A 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. |
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