Templ, J., & Schnürch, M. (2023). Allylation of C-, N-, and O-Nucleophiles via a Mechanochemically-Driven Tsuji–Trost Reaction Suitable for Late-Stage Modification of Bioactive Molecules. Angewandte Chemie International Edition, Article e202314637. https://doi.org/10.1002/anie.202314637
We present the first solvent-free, mechanochemical protocol for a palladium-catalyzed Tsuji–Trost allylation. This approach features exceptionally low catalyst loadings (0.5 mol %), short reaction times (<90 min), and a simple setup, eliminating the need for air or moisture precautions, making the process highly efficient and environmentally benign. We introduce solid, nontoxic, and easy-to-handle allyl trimethylammonium salts as valuable alternative to volatile or hazardous reagents. Our approach enables the allylation of various O-, N-, and C-nucleophiles in yields up to 99 % even for structurally complex bioactive compounds, owing to its mild conditions and exceptional functional group tolerance.
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Forschungsinfrastruktur:
Zentrum für Kernspinresonanzspektroskopie
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Projekttitel:
Substitution von gasförmigen Reagenzien durch Feststoffe: P 33064-N (FWF - Österr. Wissenschaftsfonds)
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Forschungsschwerpunkte:
Biological and Bioactive Materials: 20% Sustainable Production and Technologies: 70% Climate Neutral, Renewable and Conventional Energy Supply Systems: 10%