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

Mono- 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 carbonates.