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

被引:21
作者
Ferreira, Michel [1 ,2 ,6 ]
Bricout, Herve [1 ,2 ,6 ]
Azaroual, Nathalie [1 ,3 ,7 ]
Gaillard, Cedric [5 ]
Landy, David [1 ,4 ]
Tilloy, Sebastien [1 ,2 ,6 ]
Monflier, Eric [1 ,2 ,6 ]
机构
[1] Univ Lille Nord France, F-59000 Lille, France
[2] UCCS, UArtois, F-62300 Lens, France
[3] UDSL, Fac Pharm, F-59006 Lille, France
[4] ULCO, LSOE, F-59140 Dunkerque, France
[5] INRA, UR Biopolymeres Interact Assemblages 1268, F-44316 Nantes 3, France
[6] CNRS, UMR 8181, F-75700 Paris, France
[7] CNRS, UMR 8009, F-75700 Paris, France
关键词
amphiphiles; aqueous-phase catalysis; phosphane ligands; Tsuji-Trost reaction; water; PHASE-TRANSFER LIGANDS; M-TPPTC LIGAND; BIPHASIC HYDROFORMYLATION; 2-PHASE HYDROFORMYLATION; DEPROTECTIVE METHOD; RHODIUM COMPLEXES; PHOSPHINE-LIGANDS; SELECTIVITY; CHAIN; HYDROGENATION;
D O I
10.1002/adsc.201000014
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
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.
引用
收藏
页码:1193 / 1203
页数:11
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