<div class="csl-bib-body">
<div class="csl-entry">Templ, J., & Schnürch, M. (2025, June 4). <i>Mashing Up Tsuji-Trost Allylation : a mechanochemical approach</i> [Poster Presentation]. The International Symposium on Mechanochemistry (Mech’cheM 2025), Montpellier, France. https://doi.org/10.34726/12460</div>
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dc.identifier.uri
http://hdl.handle.net/20.500.12708/229759
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dc.identifier.uri
https://doi.org/10.34726/12460
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dc.description.abstract
The palladium-catalyzed Tsuji-Trost allylation is a versatile and fundamental reaction with widespread application in organic synthesis. By eliminating a leaving group in the allylic position, various allylic compounds can form a π-allyl metal complex with a Pd(0) species, which in turn can be attacked by a range of nucleophiles, resulting in the formation of allylated products. An alternative approach to achieve nucleophilic allylation is through the use of allyl bromide. However, this conventional allylating agent presents significant health concerns, such as high toxicity and mutagenicity. Additionally, its high flammability poses hazards during reaction setup.
Given the aforementioned toxicological and safety issues, we were encouraged to expanded our previous research on the use of quaternary ammonium salts as safe and non-toxic alkylating agents to allylation reactions. We have identified allyl trimethyl ammonium chloride as an ideal allylating agent for various O-, N-, and C-nucleophiles in a Pd-catalyzed, mechanochemical Tsuji-Trost reaction. This reaction can be performed solvent-free in a ball mill and exhibits short reaction times (90 minutes), very low catalyst loadings (0.5 mol%), and mild basic conditions. During the oxidative addition step of the catalytic cycle, solely trimethylamine is released as a gaseous by-product, eliminating the need for an additional separation step. This environmentally friendly approach employs easy-to-handle and non-toxic reagents, providing access to numerous allylated substrates. The high yields, excellent functional group tolerance, and broad applicability of this novel method are expected to facilitate late-stage functionalization of complex natural products and pharmaceutically active compounds, paving the way for a more sustainable approach in allylation.
en
dc.description.sponsorship
FWF - Österr. Wissenschaftsfonds
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dc.language.iso
en
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dc.rights.uri
http://rightsstatements.org/vocab/InC/1.0/
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dc.subject
Mechanochemistry
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dc.subject
Green API Synthesis
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dc.subject
Ball Milling
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dc.subject
sustainable synthesis
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dc.title
Mashing Up Tsuji-Trost Allylation : a mechanochemical approach
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dc.type
Presentation
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dc.type
Vortrag
de
dc.rights.license
Urheberrechtsschutz
de
dc.rights.license
In Copyright
en
dc.identifier.doi
10.34726/12460
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dc.relation.grantno
J 4922
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dc.rights.holder
Johanna Templ
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dc.type.category
Poster Presentation
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tuw.project.title
Entwicklung von i-BM in der Direkten Kupfer Mechanokatalyse
