<div class="csl-bib-body">
<div class="csl-entry">Templ, J., & Schnürch, M. (2022, August 28). <i>Selective alpha-methylation of aryl ketones using quaternary ammonium salts as solid methylating agents</i> [Poster Presentation]. EuChemS 8, Lissabon, Portugal.</div>
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dc.identifier.uri
http://hdl.handle.net/20.500.12708/152776
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dc.description.abstract
Incorporating a methyl group into small organic or bioactive molecules can positively affect their physical properties and biological effectiveness. The latter feature is commonly referred to as the "magic methyl effect". This renders the methyl group a prevalent structural motif in small-molecule drugs. Owing to its considerable impact, a late-stage introduction of a CH3-group has become a particularly promising strategy in drug discovery. Hence, the development of efficient and new strategies for selective methylation attracts broad interest in medicinal chemistry and basic research, respectively.
Traditionally applied methylating agents often suffer from inconvenient physical properties (e.g., MeBr, b.p. 4 °C, MeI, b.p. 42 °C) or high toxicity (e.g., MeI, Me2SO4). Several organometallic reagents used for methylation (e.g., MeB(OH)2, Me4Sn, Me3Al, MeMgCl, or Me2Zn) are quite challenging to handle, as some are air sensitive, show low functional group tolerance or have to be freshly prepared. These toxicological and safety concerns encouraged us to search for a novel, safe, and easy to handle reagent for direct methylation.
In our recently published paper (scan QR-code for details), we described the use of phenyl trimethylammonium iodide (PhMe3NI) as an alternative methylating agent for introducing a CH3-group in α-position to a carbonyl group. Compared to conventional methylating agents, quaternary ammonium salts have the advantages of being nonvolatile, noncancerogenic, and easy-to-handle solids. This regioselective method is characterized by ease of operational setup, use of anisole as green solvent, and yields up to 85 %.
en
dc.description.sponsorship
Fonds zur Förderung der wissenschaftlichen Forschung (FWF)
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dc.language.iso
en
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dc.subject
Methylation
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dc.subject
ammonium salt
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dc.subject
Amides
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dc.title
Selective alpha-methylation of aryl ketones using quaternary ammonium salts as solid methylating agents
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dc.type
Presentation
en
dc.type
Vortrag
de
dc.relation.grantno
P 33064-N
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dc.rights.holder
Johanna
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dc.type.category
Poster Presentation
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tuw.project.title
Substitution von gasförmigen Reagenzien durch Feststoffe
