A Green and Low Pd Loading Micellar Suzuki-Miyaura Coupling Driven by a Lignin-Derived Surfactant

In a previous study, we reported a new family of surfactants (GVn) based on a vanillic acid scaffold obtainable from lignin degradation. These amphiphiles are prepared from renewable feedstocks through esterification with long-chain alcohols followed by functionalization with glycerol carbonate. Despite containing only two hydroxyl groups, they readily form micelles and display low critical micelle concentrations. In this study, we evaluated a series of lignin-derived surfactants in the Suzuki cross-coupling reaction to assess their effectiveness in micellar catalysis. GV8, a surfactant with a C8 alkyl chain length, was found to be the most effective. The reaction scope was investigated under the optimized conditions by reacting aryl bromides with boronic acids in a 2% aqueous GV8 micellar solution, using a Palladium catalyst at 0.25% loading, and TEA as base. As a further bonus, the reaction works perfectly under aerobic conditions.