Water-soluble triphenylphosphane-3,3′,3″-tricarboxylate (m-TPPTC) ligand and methylated cyclodextrins: A new combination for biphasic rhodium-catalyzed hydroformylation of higher olefins

Advanced Synthesis and Catalysis

Volumn 348, Issue 12-13, 2006, Pages 1547-1552

  Tilloy, Sébastien ^a   Genin, Emilie ^b   Hapiot, Frédéric ^a   Landy, David ^c   Fourmentin, Sophie ^c   Genêt, Jean Pierre ^b   Michelet, Véronique ^b   Monflier, Eric ^a  

^a UNIVERSITÉ D'ARTOIS   (France)

^b PSL RESEARCH UNIVERSITY   (France)

^c UNIVERSITÉ DU LITTORAL CÔTE D OPALE   (France)

Author keywords

Cyclodextrin; Hydroformylation; Phosphane; Rhodium; Water soluble ligand

Indexed keywords

EID: 33748274721     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200606160     Document Type: Article

References (28)

1. a) W. A. Herrmann, C. W. Kohlpaintner, Angew. Chem. Int. Ed. 1993, 32, 524;
2. b) B. Cornils, E. Wiebus, CHEMTECH 1995, 33;
3. c) B. Cornils, E. Wiebus, Red. Trav. Chim. Pays-Bas 1996, 115, 211;
4. d) B. Cornils, Org. Proc. Res. & Dev. 1998, 2, 12;
5. e) B. Cornils, J. Mol. Catal. A: Chem. 1999, 143, 1.
6. TPPTS = tris(m-sulfonatophenyl)phosphane trisodium salt; a) E. G. Kuntz, CHEMTECH 1987, 17, 570;
7. for very recent biphasic applications, see: b) K. Kinoshita, H. Shinokubo, K. Oshima, Angew. Chem. Int. Ed. 2005, 44, 2397;
8. c) K. Kinoshita, H. Shinokubo, K. Oshima, J. Am. Chem. Soc. 2003, 125, 7784, and references therein.
9. B. E. Hanson, in: Aqueous-Phase Organometallic Catalysis, 2nd edn., (Eds.: B. Cornils, W. A. Herrmann), VCH, Weinheim, 2004, p. 243.
10. For a recent review on the applications of cyclodextrins, see: a) F. Hapiot, S. Tilloy, E. Monflier, Chem. Rev. 2006, 106, 767;
11. b) E. Monflier, G. Fremy, Y. Castanet, A. Mortreux, Angew. Chem. Int. Ed. 1995, 34, 2269;
12. c) E. Monflier, S. Tilloy, G. Fremy, Y. Castanet, A. Mortreux, Tetrahedron Lett. 1995, 36, 9481.
13. T. Mathivet, C. Méliet, Y. Castanet, A. Mortreux, L. Caron, S. Tilloy, E. Monflier, J. Mol. Catal. A.: Chem. 2001, 176, 105.
14. E. Monflier, H. Bricout, F. Hapiot, S. Tilloy, A. Aghmiz, A. M. Masdeu-Bultó, Adv. Synth. Catal. 2004, 346, 425.
15. m-TPPTC = tris(m-carboxyphenyl)phosphane trilithium salt: R. Amengual, E. Genin, V. Michelet, M. Savignac, J.-P. Genet, Adv. Synth. Catal. 2002, 344, 393.
16. a) R. Amengual, V. Michelet, J.-P. Genêt, Tetrahedron Lett. 2002, 43, 5905;
17. b) R. Métivier, R. Amengual, I. Leray, V. Michelet, J.-P. Genêt, Org. Lett. 2004, 6, 739;
18. c) E. Genin, V. Michelet, J.-P. Genêt, Tetrahedron Lett. 2004, 45, 4157;
19. d) E. Genin, V. Michelet, J.-P. Genêt, J. Organomet. Chem. 2004, 689, 3820;
20. e) E. Genin, R. Amengual, V. Michelet, M. Savignac, A. Jutand, L. Neuville, J.-P. Genêt, Adv. Synth. Catal. 2004, 346, 1733;
21. f) K. Kranjc, M. Kocevar, F. Iosif, S. M. Coman, V. I. Parvulescu, E. Genin, J.-P. Genêt, V. Michelet, Synlett 2006, 1075.
22. E. Monflier, S. Tilloy, C. Méliet, A. Mortreux, S. Fourmentin, D. Landy, G. Surpateanu, New. J. Chem. 1999, 23, 469.
23. E. Monflier, S. Tilloy, L. Caron, J. M. Wieruszeski, G. Lippens, S. Fourmentin, D. Landy, G. Surpateanu, J. Incl. Phenom. 2000, 38, 361.
24. B. Fell, G. Papadogianakis, J. Prakt. Chem. 1994, 336, 591.
25. S. Tilloy, G. Crowyn, E. Monflier, P. W. N. M. van Leeuwen, J. N. H. Reek New J. Chem. 2006, 1, 377.
26. Y. Kenechi, M. Atsushi, T. Yukio, S. Mitsukatsu, Y. Yoshiaki, I. Tomoyuki, Japanese Patent 8,333,406, 1996.
27. a) For TPPTS, see: R. Gärtner, B. Cornils, H. Springer, P. Lappe, German Patent DE 3,235,030, 1982;
28. [7]