<div class="csl-bib-body">
<div class="csl-entry">Templ, J., & Schnürch, M. (2025, September 15). <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> [Conference Presentation]. 11th INCOME Conference, Berlin, Germany.</div>
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Introducing double bonds into chemical compounds - through vinylation, allylation, or olefination - is a fundamental strategy in organic synthesis, providing reactive handles for further functionalization such as epoxidation, dihydroxylation, metathesis, or radical reactions. Although these transformations are well-established in conventional solution-based chemistry, the introduction of C(sp²)=C(sp²) bonds remains underdeveloped under solvent-free conditions…
…at least until our double bond agent took on the mission.
We demonstrate how these key transformations can be performed under mechanochemical conditions, focusing on three reactions: the Tsuji-Trost allylation, the Wittig olefination, and the Heck coupling under direct mechanocatalysis. Beyond eliminating solvents, these protocols offer notable advantages: reaction times as short as 30 seconds (Wittig olefination), drastically reduced catalyst loadings (0.5 mol% Pd for the Tsuji-Trost allylation), and efficient catalyst recovery - using a palladium milling ball as the active catalyst in the Heck reaction.
Along the way, we tackled what should be close to impossible: the olefination of sugars under neat conditions. Given their low open-chain content, sugars are typically poor substrates for olefination without solvent. The fact that this reaction proceeds cleanly under ball milling conditions challenges conventional expectations in dry-state synthesis.
Finally, we highlight the applicability of these methods to pharmaceutically relevant compounds, demonstrating their practical value beyond proof-of-concept.
en
dc.description.sponsorship
FWF - Österr. Wissenschaftsfonds
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dc.language.iso
en
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dc.subject
Mechanochemistry
en
dc.subject
Ball Milling
en
dc.subject
sustainable synthesis
en
dc.title
A Double Bond Agent on a Mechanochemical Mission - Ball Milling Strategies to Introduce C(sp²)=C(sp²) Bonds
en
dc.type
Presentation
en
dc.type
Vortrag
de
dc.relation.grantno
J 4922
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dc.type.category
Conference Presentation
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tuw.project.title
Entwicklung von i-BM in der Direkten Kupfer Mechanokatalyse
