Mechanochemical Palladium-catalyzed Cross-coupling of Thianthrenium Salts and Arylboronic Acids.

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.