Properties and Catalytic Activities of New Easily-Made Amphiphilic Phosphanes for Aqueous Organometallic Catalysis

International audienceMono- and disulfonated amphiphilic versions of triphenylphosphane (PPh3) and cyclohexyl(phenyl)phosphane were easily synthesized from commercial reagents and sulfuric acid. The behaviour of these phosphanes in solution was investigated by surface tension, isothermal titration calorimetry, nuclear magnetic resonance and cryo-transmission electron microscopy. Two different supramolecular assemblies were evidenced according to the degree of sulfonation. The monosulfonated phosphanes formed well organized micelle-like aggregates while the disulfonated phosphanes formed heterogeneous and disorganized vesicle-like assemblies. The efficiency of these amphiphilic phosphanes was evaluated in the aqueous biphasic, palladium-catalyzed cleavage of allyl alkyl carbonate