Cyclodextrins as mass transfer additives in aqueous organometallic catalysis

Current Organic Chemistry

Volumn 14, Issue 13, 2010, Pages 1296-1307

  Bricout, H ^a,b   Hapiot, F ^a,b   Ponchel, A ^a,b   Tilloy, S ^a,b   Monflier, E ^a,b  

^a UNIV LILLE   (France)

^b UNITÉ DE CATALYSE ET DE CHIMIE DU SOLIDE   (France)

Author keywords

Cyclodextrins; Host guest chemistry; Organometallic catalysis; Recognition; Water; Water soluble phosphines

Indexed keywords

ORGANOSILICON;

APPLICATION FIELDS; BIPHASIC PROCESS; CHEMICALLY MODIFIED; HOSTGUEST CHEMISTRY; MODIFIED CYCLODEXTRINS; ORGANOMETALLIC CATALYSIS; RECOGNITION; TRANSFER PROBLEMS; WATER-SOLUBLE PHOSPHINE; WATERSOLUBLE;

CATALYSIS;

EID: 77954924275     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527210791616920     Document Type: Article

References (75)

1. Shaughnessy, K.H. Hydrophilic ligands and their application in aqueous-phase metal-catalyzed reactions. Chem. Rev. 2009, 109, 643-710.
2. Kalck, P.; Dessoudeix, M. Inter-facial catalysis using various water-compatible ligands in supramolecular systems. Coord. Chem. Rev. 1999,192, 1185-1198.
3. Gimenez-Pedros, M.; Aghmiz, A.; Claver, C.; Masdeu-Bultó, A.M.; Sinou,D. Micellar effect in hydroformylation of high olefin catalysed by water-soluble rhodium complexes associated with sulfonated diphosphines. J. Mol.Catal. A: Chem. 2003, 200, 157-163.
4. Li, M.; Li, Y.Z.; Chen, H.; He, Y.E.; Li, X.J. Studies on 1-dodecene hydro-formylation in biphasic catalytic system containing mixed micelle. J. Mol.Catal. A: Chem. 2003, 194, 13-17.
5. Peng, Q.; Yang, Y.; Wang, C.; Liao, X.; Yuan, Y. Aqueous biphasic hydro-formylation of higher olefins catalyzed by rhodium complexes with am-phiphilic ligands of sulfonated triphenylphosphine analog. Catal. Lett. 2003, 88, 219-225.
6. Ding, H.; Hanson, B.E.; Bartik, T.; Bartik, B. Two-phase hydroformylationof octene-1 with rhodium complexes of P [C6H4(CH2)mC6H4-p-SO3Na]3 (m =3, 6). Rate and selectivity enhancement with surface-active phosphines. Or-ganometallics 1994, 13, 3761-3763.
7. Kunna, K.; Müller, C.; Loos, J.; Vogt, D. Aqueous-phase hydroformylationof 1-octene: Styrene latices as phase-transfer agents. Angew. Chem. Int. Ed. 2006, 45, 7289-7292.
8. Bortenschlager, M.; Schöllhorn, N.; Wittmann, A.; Weberskirch, R. Triphen-ylphosphane-functionalised amphiphilic copolymers: Tailor-made supportmaterials for the efficient and selective aqueous two-phase hydroformylationof 1-octene. Chem. Eur. J. 2007, 13, 520-528.
9. Szejtli, J. Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 1998, 98, 1743-1753.
10. Zahalka, H.A.; Januszkiewicz, K.; Alper, H. Olefin oxidation catalyzed bypalladium chloride using cyclodextrins as phase transfer agents. J. Mol.Catal. 1986, 35, 249-253.
11. Zahalka, H.A.; Alper, H. β-cyclodextrin-promoted, rhodium(I)-catalyzedconversion of carbonyl compounds to hydrocarbons under remarkably mildconditions. Organometallics 1986, 5, 1909-1911.
12. Harada, A.; Hu, Y.; Takahashi, S. Cyclodextrin-palladium choride. Newcatalytic system for selective oxidation of olefins to ketones. Chem. Lett.1986, 2083-2084.
13. Lee, J.T.; Alper, H. The hydridopentacyanocobaltate anion induced deoxy-genation of allylic alcohols using β-cyclodextrin as a phase transfer agent. Tetrahedron Lett. 1990, 31, 4101-4104.
14. Lee, J.T.; Alper, H. β-cyclodextrin and hydridopentacyanocobaltate cata-lyzed selective hydrogenation of, α,β-unsaturated acids and their derivatives. Tetrahedron Lett. 1990, 31, 1941-1942.
15. Lee, J.T.; Alper, H. Regioselective hydrogenation of conjugated dienescatalyzed by hydridopentacyanocobaltate anion using -cyclodextrin as thephase transfer agent and lanthanide halides as promoters. J. Org. Chem.1990, 55, 1854-1856.
16. Benyei, A.; Joó, F. Organometallic catalysis in aqueous solutions: the bipha-sic transfer hydrogenation of aldehydes catalyzed by water soluble phosphinecomplexes of ruthenium, rhodium and iridium. J. Mol. Catal. 1990, 58, 151-163.
17. Anderson, J.R.; Campi, E.M.; Jackson, W.R. Hydroformylation of olefinswith water-soluble rhodium catalysts in the presence of -cyclodextrin. Catal. Lett. 1991, 9, 55-58.
18. Pinel, C.; Gendreau-Diaz, N.; Bréhéret, A.; Lemaire M. Asymmetric hydro-genation of -keto ester with diamine-complexed metal. J. Mol. Catal., A:Chem. 1996, 112, L157-L161.
19. Monflier, E.; Blouet, E.; Barbaux, Y.; Mortreux, A. Wacker oxidation of 1-decene to 2-decanone in the presence of a chemically modified cyclodextrinsystem: A happy union of host-guest chemistry and homogeneous catalysis. Angew. Chem., Int. Ed. Engl. 1994, 33, 2100-2102.
20. Monflier, E.; Tilloy, S.; Fremy, G.; Barbaux, Y.; Mortreux, A. A very usefuland efficient Wacker oxidation of higher -olefins in the presence of per(2,6-di-O-methyl)-β-Cyclodextrin. Tetrahedron Lett. 1995, 36, 387-388.
21. Monflier, E.; Tilloy, S.; Blouet, E.; Barbaux, Y.; Mortreux, A. Wackeroxidation of various olefins in the presence of per(2,6-di-O-methyl)--cyclodextrin: mechanistic investigations of a multistep catalysis in a solvent-free two-phase system. J. Mol. Catal., A: Chem. 1996, 109, 27-35.
22. Maksimov, A.L.; Sakharov, D.A.; Filippova, T.Y.; Zhuchkova, A.Y.; Kara-khanov, E.A. Supramolecular catalysts on the basis of molecules-receptors. Ind. Eng. Chem. Res. 2005, 44, 8644-8653.
23. Karakhanov, E.A.; Karapetyan, L.M.; Kardasheva, Y.S.; Maksimov, A.L.; Runova, E.A.; Skorkin, V.A.; Terenina, M.V. Molecular recognition and ca-talysis: from macrocyclic receptors to molecularly imprinted metal complexes. Macromol. Symp. 2006, 235, 39-51.
24. Karakhanov, E.A.; Filippova, T.Y.; Martynova, S.A.; Maximov, A.L.; Pre-deina, V.V.; Topchieva, I.N. New catalytic systems for selective oxidation ofaromatic compounds by hydrogen peroxide. Catal. Today 1998, 44, 189-198.
25. Karakhanov, E.A.; Maksimov, A.L.; Ivanova, E.A. Supramolecular catalyticsystems in biomimetic oxidation. Russ. Chem. Bull. Int. Ed. 2007, 56, 621-630.
26. Tilloy, S.; Bertoux, F.; Mortreux, A.; Monflier, E. Chemically modified -cyclodextrins in biphasic catalysis: a fruitful contribution of the host-guestchemistry to the transition-metal catalyzed reactions. Catal. Today 1999, 48,245-253.
27. Monflier, E.; Fremy, G.; Castanet, Y.; Mortreux, A. Molecular recognitionbetween chemically modified β-cyclodextrin and dec-1-ene: new prospectsfor biphasic hydroformylation of water-insoluble olefins. Angew. Chem. Int.Ed. Engl. 1995, 34, 2269-2271.
28. Monflier, E.; Tilloy, S.; Fremy, G.; Castanet, Y.; Mortreux, A. A furtherbreakthrough in biphasic, rhodium catalyzed hydroformylation: the use ofper(2,6-di-O-methyl)-β-cyclodextrin as inverse phase transfer catalyst. Tet-rahedron Lett. 1995, 36, 9481-9484.
29. Kalck, P.; Miquel, L.; Dessoudeix, M. Various approaches to transfers im-provement during biphasic catalytic hydroformylation of heavy alkenes. Catal. Today 1998, 42, 431-440.
30. Dessoudeix, M.; Urrutigoïty, M.; Kalck, P. Catalytic activity enhancement ofa cyclodextrin/water-soluble rhodium complex system due to its gradual su-pramolecular organization in the interphase. Eur. J. Inorg. Chem. 2001,1797-1800.
31. Dabbawala, A.A.; Parmar, J.N.; Jasra, R.V.; Bajaj, H.C.; Monflier, E. Cobaltcatalyzed hydroformylation of higher olefins in the presence of chemicallymodified cyclodextrins. Catal. Commun. 2009, 10, 1808-1812.
32. Monflier, E.; Tilloy, S.; Bertoux, F.; Castanet, Y.; Mortreux, A. New pros-pects for the palladium catalyzed hydrocarboxylation of higher -olefins intwo-phase system: the use of chemically modified-β-cyclodextrin. New J.Chem. 1997, 21, 857-859.
33. Monflier, E.; Tilloy, S.; Castanet, Y.; Mortreux, A. Chemically modified -cyclodextrins: efficient supramolecular carriers for the biphasic hydrogena-tion of water-insoluble aldehydes. Tetrahedron Lett. 1998, 39, 2959-2960.
34. Tilloy, S.; Bricout, H.; Monflier, E. Cyclodextrins as inverse phase transfercatalysts for the biphasic catalytic hydrogenation of aldehydes: a green andeasy alternative to conventional mass transfer promoters. Green Chem. 2002,4, 188-193.
35. Monflier, E.; Tilloy, S.; Méliet, C.; Mortreux, A.; Fourmentin, S.; Landy, D.; Surpateanu, G. First evidence of molecular recognition between cyclodex-trins and a water-soluble ligand used in aqueous phase organometallic catalysis. New J. Chem. 1999, 23, 469-472.
36. Monflier, E.; Tilloy, S.; Caron, L.; Wieruszeski, J.M.; Lippens, G.; Fourmen-tin S.; Landy, D.; Surpateanu, G. Study of the inclusion complexes of -cyclodextrin with the sodium salt of trisulfonated triphenylphosphine. J. In-clusion Phenom. 2000, 38, 361-379.
37. Da Costa, A.; Monflier, E.; Landy, D.; Fourmentin, S.; Surpateanu, G. Scan-ning tunnelling microscopy investigation of an inclusion complex betweenthe -cyclodextrin and the sodium salt of the trisulfonated triphenyl-phosphine. Surf. Sci., 2001, 470, 275-283.
38. Mathivet, T.; Méliet, C.; Castanet, Y.; Mortreux, A.; Caron, L.; Tilloy, S.; Monflier, E. Rhodium catalyzed hydroformylation of water insoluble olefinsin the presence of chemically modified β-cyclodextrins: Evidence for ligand-cyclodextrin interactions and effect of various parameters on the activity andthe aldehydes selectivity. J. Mol. Catal., A.: Chem. 2001, 176, 105-116.
39. 31P{1H} NMR studies of RhH(CO)(TPPTS)3 in thepresence of methylated cyclodextrins: New light on rhodium catalyzed hy-droformylation reaction assisted by cyclodextrins. Adv. Synth. Catal. 2004,346, 425-431.
40. Binkowski, C.; Cabou, J.; Bricout, H.; Hapiot, F.; Monflier, E. Cleavage ofwater-insoluble alkylallylcarbonates catalysed by a palla-dium/TPPTS/cyclodextrin system: effect of phosphine/cyclodextrin interac-tions on the reaction rate. J. Mol. Catal. 2004, 215, 23-32.
41. Caron, L.; Christine, C.; Tilloy, S.; Monflier, E.; Landy, D.; Fourmentin, S.;Surpateanu, G. One and two-dimensional NMR investigations of the inclu-sion of the monosulfonated triphenylphosphine in the β-cyclodextrin. Su-pramol. Chem. 2002, 14, 11-20.
42. Canipelle, M.; Tilloy, S.; Bricout, H.; Monflier, E. Complexation of mono-sulfonated triphenylphosphine with chemically modified -cyclodextrins: Ef-fect of substituents on the stability of inclusion complexes. J. Inclusion Phe-nom. 2005, 51, 79-85.
43. Canipelle, M.; Caron, L.; Christine, C.; Tilloy, S.; Monflier, E. Thermody-namic insight into the origin of the inclusion of monosulfonated isomers oftriphenylphosphine into the -cyclodextrin cavity. Carbohydr. Res. 2002,337, 281-287.
44. Tilloy, S.; Genin, E.; Hapiot, F.; Landy, D.; Fourmentin, S.; Genêt, J.P.; Michelet, V.; Monflier, E. Water-soluble triphenylphosphane-3,3′,3″-tricarboxylate (m-TPPTC) ligand and methylated cyclodextrins: A new com-bination for biphasic rhodium-catalyzed hydroformylation of higher olefins. Adv. Synth. Catal. 2006, 348, 1547-1552.
45. Leclercq, L.; Hapiot, F.; Tilloy, S.; Ramkisoensing, K.; Reek, J.N.H.; vanLeeuwen, P.W.N.M.; Monflier E. Sulfonated xantphos ligand and methylatedcyclodextrin: A winning combination for rhodium catalysed hydroformyla-tion of higher olefins in aqueous medium. Organometallics 2005, 24, 2070-2075.
46. Tilloy, S.; Crowyn, G.; Monflier, E.; van Leeuwen, P.W.N.M.; Reek J.N.H. Hydroformylation of 1-decene in aqueous medium catalyzed by rho-dium/alkyl sulfonated diphosphines system in the presence of methylated β-cyclodextrins. How the flexibility of the diphosphine backbone influencesthe regioselectivity. New. J. Chem. 2006, 30, 377-383.
47. Ferreira, M.; Bricout, H.; Sayede, A.; Ponchel, A.; Fourmentin, S.; Tilloy, S.; Monflier, E. Biphasic aqueous organometallic catalysis promoted by cyclo-dextrins: how to design the water-soluble phenylphosphane to avoid interaction with cyclodextrin. Adv. Synth. Catal. 2008, 350, 609-618.
48. Legrand, F.X.; Hapiot, F.; Tilloy, S.; Guerriero, A.; Peruzzini, M.; Gonsalvi, L.; Monflier, E. Aqueous rhodium-catalyzed hydroformylation of 1-decenein the presence of randomly methylated β-cyclodextrin and 1,3,5-triaza-7-phosphaadamantane derivatives. Appl. Catal. A: Gen. 2009, 362, 62-66.
49. Leclercq, L.; Sauthier, M.; Castanet, Y.; Mortreux, A.; Bricout, H.; Monflier, E. Two-Phase hydroformylation of higher olefins using randomly methylated-cyclodextrin as mass transfer promoter: a smart solution for preserving theintrinsic properties of the rhodium/trisulfonated triphenylphosphine catalyticsystem. Adv. Synth. Catal. 2005, 347, 55-59.
50. Sueur, B.; Leclercq, L.; Sauthier, M.; Castanet, Y.; Mortreux, A.; Bricout H.; Tilloy, S.; Monflier, E. Rhodium complexes non-covalently bound to cyclo-dextrins: Novel water-soluble supramolecular catalysts for the biphasic hy-droformylation of higher olefins. Chem. Eur. J. 2005, 11, 6228-6236.
51. Reetz, M.T. Supramolecular Transition Metal Catalysts in Two-Phase Systems. Catal. Today 1998, 42, 399-411.
52. Reetz, M.T. New supramolecular transition metal catalysts. J. Heterocycl.Chem. 1998, 35, 1065-1073.
53. Reetz, M.T. New approaches to supramolecular transition metal catalysis.Top. Catal. 1997, 4, 187-200.
54. Reetz, M.T.; Waldvogel S.R. β-cyclodextrin-modified diphosphanes asligands for supramolecular rhodium catalysts. Angew. Chem. Int. Ed. Engl. 1997, 36, 865-867.
55. Armspach, D.; Matt, D. Metal-capped β-cyclodextrins: the crowning of theoligosaccharide torus with precious metals. Chem. Commun. 1999, 1073-1074.
56. Blach, P.; Landy, D.; Fourmentin, S.; Surpateanu, G.; Bricout, H.; Ponchel, A.; Hapiot, F.; Monflier, E. Sulfobutyl ether-β-cyclodextrins: Promising su-pramolecular carriers for aqueous organometallic catalysis. Adv. Synth. Catal. 2005, 347, 1301-1307.
57. Kirschner, D.; Jaramillo, M.; Green, T.; Hapiot, F.; Leclercq, L.; Bricout, H.; Monflier, E. Fine tuning of sulfoalkylated cyclodextrin structures to improvetheir mass-transfer properties in an aqueous biphasic hydroformylation reaction. J. Mol. Catal. A.: Chem. 2008, 286, 11-20.
58. Kirschner, D.; Green, T.; Hapiot, F.; Tilloy, S.; Leclercq, L.; Bricout, H.;Monflier, E. Heptakis(2,3-di-O-methyl-6-O-sulfopropyl)--cyclodextrin: agenuine supramolecular carrier for the aqueous organometallic catalysis. Adv. Synth. Catal. 2006, 348, 379-386.
59. Sieffert, N.; Wipff, G. Adsorption at the liquid-liquid interface in the bipha-sic rhodium catalyzed hydroformylation of olefins promoted by cyclodex-trins: A molecular dynamics study. J. Phys. Chem. B 2006, 110, 4125-4134.
60. Sieffert, N.; Wipff, G. Importance of interfacial adsorption in the biphasichydroformylation of higher olefins promoted by cyclodextrins: A moleculardynamics study at the decene/water interface. Chem. Eur. J. 2007, 13, 1978-1990.
61. Leclercq, L.; Bricout, H.; Tilloy, S.; Monflier, E. Biphasic aqueous or-ganometallic catalysis promoted by cyclodextrins: Can surface tension meas-urements explain the efficiency of chemically modified cyclodextrins? J.Colloid Interface Sci. 2007, 307, 481-487.
62. Legrand, F.X.; Sauthier, M.; Flahaut C.; Hachani, J.; Elfakir, C.; Fourmentin, S.; Tilloy, S.; Monflier, E. Aqueous hydroformylation reaction mediated byrandomly methylated β-cyclodextrin: How substitution degree influencescatalytic activity and selectivity. J. Mol. Catal. A: Chem. 2009, 303, 72-77.
63. Lacroix, T.; Bricout, H.; Tilloy, S.; Monflier, E. Chemically modified β-cyclodextrins as supramolecular carriers in the biphasic palladium-catalyzedcleavage of allylic carbonates: Activity enhancement and substrate-selectivecatalysis. Eur. J. Org. Chem. 1999, 3127-3129.
64. Bricout, H.; Caron, C.; Bormann, D.; Monflier, E. Substrate-selective cataly-sis in an aqueous biphasic system with per(2,6-di-O-methyl)--cyclodextrin.Catal. Today 2001, 66, 355-361.
65. Torque, C.; Bricout, H.; Hapiot, F.; Monflier, E. Substrate-selective aqueousorganometallic catalysis. How size and chemical modification of cyclodex-trin influence the substrate selectivity. Tetrahedron 2004, 60, 6487-6493.
66. Cabou, J.; Bricout, H.; Hapiot, F.; Monflier, E. Methylated-β-cyclodextrins:Useful discriminating tools for substrate-selective reactions in aqueous or-ganometallic catalysis. Catal. Commun. 2004, 5, 265-270.
67. Torque, C.; Sueur, B.; Cabou, J.; Bricout, H.; Hapiot, F.; Monflier E. Sub-strate-selective aqueous organometallic catalysis. How small water-solubleorganic molecules enhance the supramolecular discrimination. Tetrahedron 2005, 61, 4811-4817.
68. Hirano, K.; Yorimitsu, H.; Oshima K. Alkylation of aldehydes with trialkyl-boranes in water. Adv. Synth. Catal. 2006, 348, 1543-1546.
69. Hirano, K.; Yorimitsu, H.; Oshima K. Nickel-catalysed reactions with trial-kylboranes and silacyclobutanes. Chem. Commun. 2008, 3234-3241.
70. Behr, A.; Leschinski, J.; Awungacha, C.; Simic, S.; Knoth, T. Telomerizationof butadiene with glycerol: reaction control through process engineering,solvents, and additives. ChemSusChem 2009, 2, 71-76.
71. Ding, L.; Jiao, X.; Deng, J.; Zhao, W.; Yang, W. Catalytic polymerizationsof hydrophobic, substituted, acetylene monomers in an aqueous medium byusing a monomer/hydroxypropyl-β-cyclodextrin inclusion complexation. Macromol. Rapid Commun. 2009, 30, 120-125.
72. Denicourt-Nowicki, A.; Roucoux, A.; Wyrwalski, F.; Kania, N.; Monflier,E.; Ponchel A. Carbon-supported ruthenium nanoparticles stabilized bymethylated cyclodextrins: a new family of heterogeneous catalysts for gasphase hydrogenation of arenes. Chem. Eur. J. 2008, 14, 8090-8093.
73. Hubert, C.; Denicourt-Nowicki, A.; Roucoux, A.; Landy, D.; Léger, B.; Crowyn G.; Monflier E. Catalytically active nanoparticles stabilized by host-guest inclusion complexes in water. Chem. Commun., 2009, 1228-1230.
74. Machut, C.; Patrigeon, J.; Tilloy, S.; Bricout, H.; Hapiot, F.; Monflier E. Self-assembled supramolecular bidentate ligands for aqueous organometalliccatalysis. Angew. Chem. Int. Ed. 2007, 46, 3040-3042.
75. Binkowski-Machut, C.; Canipelle, M.; Bricout, H.; Tilloy, S.; Hapiot, F.; Monflier E. Supramolecular trapping of phosphanes by cyclodextrins: Ageneral approach to generate phosphane coordinatively unsaturated or-ganometallic complexes. Eur. J. Inorg. Chem. 2006, 1611-1619.