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

    Year: 2010

    Journal: Advanced Synthesis & Catalysis, Volume 352, Issue 7, pages 1193–1203, May 3, 2010, 20111221

    Authors: Michel Ferreira1,2,6, Hervé Bricout1,2,6, Nathalie Azaroual1,3,7, Cédric Gaillard5, David Landy1,4, Sébastien Tilloy1,2,6, Eric Monflier1,2,6

    Organizations: 1Université Lille Nord de France, 59000 Lille, France 2UArtois, UCCS, rue Jean Souvraz, 62300 Lens, France 3UDSL, Faculté de Pharmacie, BP 83, 59006 Lille, France 4ULCO, LSOE, 145, Avenue Maurice Schumann, MREI 1, 59140 Dunkerque, France 5INRA, UR1268 Biopolymères Interactions Assemblages, BP 71 627, Rue de la Géraudière, 44316 Nantes Cedex 3, France 6CNRS, UMR 8181 7CNRS, UMR 8009

    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.