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Mechanochemical Palladium‐Catalyzed Cross‐Coupling of Thianthrenium Salts and Arylboronic Acids

Zuzana Mravíková, Tibor Peňaška, Daniela Horniaková, Radovan Šebesta

2025ChemSusChem9 citationsDOI

Abstract

Cross-coupling reactions are indispensable for the construction of complex molecular scaffolds. In this work, we developed a sustainable methodology for the cross-coupling reaction of arene thianthrenium salts with aryl boronic acids, which can be effectively realized under mechanochemical conditions. Liquid-assisted grinding (LAG) enabled fast and high-yielding synthesis of a range of biaryls via Pd/RuPhos-catalyzed cross-coupling. The transformation works under ambient temperature and on air. Environmentally friendly solvent 2-methyltetrahydrofurane (Me-THF) was used as a LAG additive. Moreover, the major by-product of the cross-coupling reaction, thianthrene, can be recovered and reused.

Topics & Concepts

PalladiumArylCatalysisChemistryCoupling reactionEnvironmentally friendlyCoupling (piping)SolventGrindingCombinatorial chemistryGreen chemistryOrganic chemistryChemical engineeringMaterials scienceReaction mechanismMetallurgyBiologyEcologyEngineeringAlkylBioactive Compounds and Antitumor Agents
Mechanochemical Palladium‐Catalyzed Cross‐Coupling of Thianthrenium Salts and Arylboronic Acids | Litcius