<div class="csl-bib-body">
<div class="csl-entry">Templ, J., Schnürch, M., & Borchardt, L. (2025, October 14). <i>A Double Bond Agent on a Mechanochemical Mission : Ball Milling Strategies to Introduce C(sp<sup>2</sup>)=C(sp<sup>2</sup>) Bonds</i> [Poster Presentation]. Technologies Shaping Future Directions in Synthesis : Beilstein Organic Chemistry Symposium 2025, Limburg a. d. Lahn, Germany. https://doi.org/10.34726/12465</div>
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dc.identifier.uri
http://hdl.handle.net/20.500.12708/229786
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dc.identifier.uri
https://doi.org/10.34726/12465
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dc.description.abstract
“Shaken, not stirred …”
It’s a quote almost everyone has heard, whether they’ve watched a James Bond movie or not. But what if this iconic phrase isn’t just about Martinis? What if it’s a subtle hint about how we can address some of the most pressing challenges facing our planet? A call to tackle rising environmental demands in the chemical industry - particularly the fine chemical and pharmaceutical sectors, where solvent waste generation is a significant concern. And what if, contrary to Bond’s love for Martini, “alcohol is not the solution”? In fact, what if the real solution is… no solution at all?
--- Enter mechanochemistry ---
This isn’t just a method; it’s a transformative approach that enables chemical transformations under solvent-free conditions or with minimal solvent use. It relies on energy generated by friction, shear, and impact forces within milling systems. Beyond reducing solvent waste, mechanochemistry offers unparalleled opportunities to revolutionize synthetic chemistry - and we’re only beginning to unlock its potential. As a chemist, I am not bound by secrecy like 007. Instead, I’m on a clear mission: to champion mechanochemistry and inspire scientists around the globe.
And what better place to push this mission forward than at an organic chemistry symposium? After all, the need for greener, solvent-free synthetic strategies is especially urgent in organic and pharmaceutical chemistry. Among the most important transformations in this field is the formation of carbon–carbon double bonds through vinylation, allylation, or olefination. These reactions serve as key strategic steps in synthesis, introducing versatile functional handles for further modifications such as epoxidation, dihydroxylation, metathesis, or radical reactions. Although well-established under traditional solution-phase conditions, these C(sp2)=C(sp2) bond-forming strategies remain significantly underexplored under solvent-free mechanochemical conditions…
…at least until a double-bond agent took on the mission.
My work demonstrates how these core transformations can be performed efficiently using mechanochemical techniques, specifically focusing on three representative reactions: the Tsuji–Trost allylation, the Wittig olefination, and the Heck coupling under direct mechanocatalysis. These protocols do not simply eliminate solvents, they bring additional benefits: reaction times reduced to as little as 30 seconds in the case of the Wittig olefination; catalyst loadings cut to 0.5 mol% palladium in the Tsuji–Trost allylation; and, notably, the use of palladium milling balls as both catalyst and grinding medium in the Heck reaction, enabling easy catalyst recovery and reuse.
Figure 1. Scope for mechanochemical reactions introducing double bonds to organic molecules (top) and their applications in the late-stage modification of bioactive compounds (bottom).
Along the way, we also tackled a challenge many would consider a mission impossible: the olefination of sugars under neat conditions. Given their low open-chain content and generally poor reactivity in dry environments, carbohydrates are far from ideal candidates for such transformations. Yet, under ball milling conditions, the reaction proceeds cleanly without bulk solvents - challenging long-held assumptions about what is possible in dry-state synthesis.
To underscore the relevance of these methods beyond academic interest, I have applied them to pharmaceutically relevant substrates, providing early proof of their industrial potential. The final mission objective: to demonstrate the feasibility of using these approaches in active pharmaceutical ingredient (API) synthesis on an industrial scale, offering a practical strategy for reducing solvent waste in real-world pharmaceutical manufacturing.
en
dc.description.sponsorship
FWF - Österr. Wissenschaftsfonds
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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
Ball Milling
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dc.subject
Solvent-free Synthesis
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dc.title
A Double Bond Agent on a Mechanochemical Mission : Ball Milling Strategies to Introduce C(sp²)=C(sp²) Bonds
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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
10.34726/12465
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dc.contributor.affiliation
Ruhr University Bochum, Germany
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dc.relation.grantno
J 4922
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dc.relation.grantno
P 33064-N
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dc.rights.holder
Templ, Johanna
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dc.type.category
Poster Presentation
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tuw.publication.invited
invited
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tuw.project.title
Entwicklung von i-BM in der Direkten Kupfer Mechanokatalyse
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tuw.project.title
Substitution von gasförmigen Reagenzien durch Feststoffe
