Inter-facial catalysis using various water-compatible ligands in supramolecular systems

Kalck, Philippe; Dessoudeix, Michel

doi:10.1016/s0010-8545(99)00175-7

Cited by 37 publications

(11 citation statements)

References 35 publications

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“…Since the mid‐1970s and the pioneering works of E. Kuntz,1,2 the use of water in organometallic catalysis has been tackled but its application was limited to water‐soluble substrates. For hydrophobic reactants, the problem has since partially been solved with the use of co‐solvents,3,4 surfactants,5–14 amphiphilic phosphanes,15–23 molecular receptors,24–26 polymers27 or dispersed particles,28 all capable of improving the mass transfer between the substrate‐containing organic phase and the catalyst. Among these strategies, the use of amphiphilic phosphanes appeared promising as the surface‐active property and the coordination ability were incorporated into the same entity.…”

Section: Introductionmentioning

confidence: 99%

Cyclodextrin/Amphiphilic Phosphane Mixed Systems and their Applications in Aqueous Organometallic Catalysis

et al. 2012

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When mixed with a water-soluble phosphane capable of self-assembling into micelles, native or modified b-cyclodextrins (b-CDs) show very contrasting behavior depending on their neutral or ionic nature. In the post-micellar region, neutral b-CDs led to a micelle destructuring. Conversely, micelles remained stable over a well-defined range of ionic b-CD concentrations. In that case, the micelle destruction was only observed when using a large excess of ionic b-CDs. The catalytic performances of these micellar systems have been evaluated in a rhodium-catalyzed hydroformylation reaction of 1-decene. We showed that, using ionic b-CDs, the catalytic activity could be improved without a detrimental impact upon the regioselectivity. A linear/branched aldehyde ratio as high as 8.6 could be achieved. The best results were obtained with stoichiometric quantities of ionic randomly methylated b-CDs with respect to the phosphane with a beneficial effect on the decantation at the end of the reaction.

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Section: Introductionmentioning

confidence: 99%

Cyclodextrin/Amphiphilic Phosphane Mixed Systems and their Applications in Aqueous Organometallic Catalysis

et al. 2012

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“…As shown in Figure 1, the 31 P NMR spectrum of 1 (3 m) exhibits, besides the minor resonance of the phosphane oxide impurity at δ ϭ 35.7 ppm, a characteristic sharp doublet at δ ϭ 44.7 ppm (J Rh,P ϭ 156 Hz). [9,10] When three equivalents of β-CD or RAMEB (9 m) was added under nitrogen or carbon monoxide to an aqueous solution of 1, no significant shift of any NMR signal was observed at different temperatures (20, 40 and 60°C), suggesting that the cyclodextrin derivatives have no effect on the organometallic complex.…”

Section: Resultsmentioning

confidence: 99%

Unexpected Effect of Cyclodextrins on Water‐Soluble Rhodium Complexes

et al. 2003

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As shown by 31P NMR spectroscopy, addition of β‐cyclodextrin or randomly methylated β‐cyclodextrin to an aqueous solution of [HRh(CO){P(m‐C6H4SO3Na)3}3] has no effect on the organometallic complex. In contrast, [HRh(CO){(p‐tBuC6H4)P(m‐C6H4SO3Na)2}3] can be partially converted in the presence of the same β‐cyclodextrin derivatives into the hydroxy complex [HORh(CO){(p‐tBuC6H4)P(m‐C6H4SO3Na)2}2], under nitrogen, or to the hydrido complex [HRh(CO)2{(p‐tBuC6H4)P(m‐C6H4SO3Na)2}2] under carbon monoxide. This remarkable difference of behavior was attributed to the fact that the phosphane (p‐tBuC6H4)P(m‐C6H4SO3Na)2 forms more stable inclusion complexes with the β‐cyclodextrin derivatives than the phosphane P(m‐C6H4SO3Na)3. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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“…During the last two decades, environmental aspects including catalysts and solvent recycling became an issue. Therefore, supported [25][26][27][28][29][30][31][32], water soluble [33] or biphasic systems [34][35][36], as realized in the Rhone-Poulenc process, have been developed [37][38][39][40]. Alternatively, the use of ionic liquids [41][42][43][44][45] or supercritical CO 2 has been reported [46].…”

Section: Hydroformylation Reactionsmentioning

confidence: 99%

N-Acetyl-N,N-dipyrid-2-yl (cyclooctadiene) rhodium (I) and iridium (I) complexes: Synthesis, X-ray structures, their use in hydroformylation and carbonyl hydrosilylation reactions and in the polymerization of diazocompounds

Bantu

Wurst

Buchmeiser

2007

Journal of Organometallic Chemistry

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Inter-facial catalysis using various water-compatible ligands in supramolecular systems

Cited by 37 publications

References 35 publications

Cyclodextrin/Amphiphilic Phosphane Mixed Systems and their Applications in Aqueous Organometallic Catalysis

Cyclodextrin/Amphiphilic Phosphane Mixed Systems and their Applications in Aqueous Organometallic Catalysis

Unexpected Effect of Cyclodextrins on Water‐Soluble Rhodium Complexes

N-Acetyl-N,N-dipyrid-2-yl (cyclooctadiene) rhodium (I) and iridium (I) complexes: Synthesis, X-ray structures, their use in hydroformylation and carbonyl hydrosilylation reactions and in the polymerization of diazocompounds

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