Aqueous biphasic hydrogenations catalyzed by rhodium and iridium complexes modified with human serum albumin

Applied Catalysis A: General

Volumn 373, Issue 1-2, 2010, Pages 76-80

  Marchetti, Mauro ^a   Minello, Fabiola ^b   Paganelli, Stefano ^b   Piccolo, Oreste ^b,c  

^a CNR   (Italy)

^b CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

^c Studio di Consulenza Scientifica   (Italy)

Author keywords

Biphasic catalysis; Human serum albumin; Hydrogenation; Iridium catalyst; Rhodium catalyst

Indexed keywords

BIPHASIC CATALYSIS; HUMAN SERUM ALBUMIN; HUMAN SERUM ALBUMINS; IRIDIUM CATALYST; RHODIUM CATALYSTS;

ALDEHYDES; BODY FLUIDS; CATALYSIS; CATALYSTS; COMPLEXATION; DYES; HYDROGENATION; IRIDIUM; IRIDIUM COMPOUNDS; KETONES; RHODIUM; UNSATURATED COMPOUNDS;

RHODIUM COMPOUNDS;

EID: 74249103225     PISSN: 0926860X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.apcata.2009.10.042     Document Type: Article

References (35)

1. In: Cornils B., Herrmann W.A., Horvath I.T., Leitner W., Mecking S., Olivier-Bourbigou H., and Vogt D. (Eds). Multiphase Homogeneous Catalysis (2005), Wiley-VCH, Weinheim
2. Joò F. Aqueous Organometallic Catalysis (2001), Kluwer Acad. Publ., Dordrecht
3. In: Cornils B., and Herrmann W.A. (Eds). Aqueous-Phase Organometallic Catalysis. 2nd ed. (2004), Wiley-VCH, Weinheim
4. Kuntz E.G. Chemtech 17 (1987) 570-575
5. Cornils B., and Kuntz E.G. J. Organomet. Chem. 502 (1995) 177-186
6. Cornils B. Org. Process Res. Dev. 2 (1998) 121-127
7. E. Kuntz, Rhône-Poulenc Ind., Fr.Pat. 2314910, 1975; DE 2627354, 1976.
8. Grosselin J.M., Mercier C., Allmag G., and Grass F. Organometallics 10 (1991) 2126-2133
9. Dwars T., and Oehme G. Adv. Synth. Catal. 344 (2002) 239-260 and references therein
10. Chen B., Dingerdissen U., Krauter J.G.E., Lansink Rotgerink H.G.J., Mobus K., Ostgard D.J., Panster P., Riermeier T.H., Seebald S., Tacke T., and Trauthwein H. Appl. Catal. A: Gen. 280 (2005) 17-46 and references therein
11. Joò F. Acc. Chem. Res. 35 (2002) 738-745
12. Gulyàs H., Bényei A.C., and Bakos J. Inorg. Chim. Acta 357 (2004) 3094-3098
13. Nuithitikul K., and Winterbottom M. Chem. Eng. Sci. 59 (2004) 5439-5447
14. Nuithitikul K., and Winterbottom M. Catal. Today 128 (2007) 74-79
15. Y. Watanabe, T. Ueno, S. Abe, Nagoya Industrial Science Research Institute, US 2005/0049405.
16. T. Ueno, Y. Watanabe, M. Ohashi, T. Koshiyama, N. Yokoi, Nagoya Industrial Science Research Institute, US 2005/0096260.
17. Marchetti M., Mangano G., Paganelli S., and Botteghi C. Tetrahedron Lett. 41 (2000) 3717-3720
18. Bertucci C., Botteghi C., Giunta D., Marchetti M., and Paganelli S. Adv. Synth. Catal. 344 (2002) 556-562
19. Paganelli S., Spano L., Marchetti M., and Piccolo O. Chim. Ind. 87 (2005) 94-98
20. Paganelli S., Ciappa A., Marchetti M., Scrivanti A., and Matteoli U. J. Mol. Catal. A: Chem. 247 (2006) 138-144
21. M. Shirai, Y. Yoshida, Ube Industries, Ltd., Japan, JP 2004269376, 2004.
22. Perrin D.D., and Armarego L.F. Purification of Laboratory Chemicals. 3rd ed. (1988), Pergamon Press, Oxford
23. 2, without any external ligand, was employed to hydrogenate 2-cyclohexen-1-one (I) in toluene at 40 °C and 2 MPa: after 1 h, ketone I was completely converted to cyclohexanone (II) but the Ir complex was completely reduced to metallic iridium.
24. 2: after 1 h, conversion was complete with formation of 80% of saturated aldehyde X and 20% of the corresponding alcohol XI. By prolonging the reaction time to 22 h we obtained the same result. It is noteworthy that at the end of the reaction the solution was clear and colourless as the rhodium complex was totally transformed into black metallic rhodium.
25. Kraft P., Bajgrowicz J.A., Denis C., and Frater G. Angew. Chem. Int. Ed. 39 (2000) 2980-3010
26. M. Shirai, Y. Yoshida, S. Sadaike, UBE, WO 054997, 2004.
27. W. Chen, G. Luo, W. Lu, Hangzhou Gelin Perfume Chemistry Co., CN 1365962, 2002.
28. T. Kawanobe, O. Takasawa, M. Amaike, Hasegawa Koryo Co., JP 10120674, 1998.
29. A.J. Chalk, S.A. Magennis, Givaudan, DE 2627112, 1976.
30. Chalk A.J., and Magennis S.A. J. Org. Chem. 41 (1976) 1206-1209
31. Enders D., and Baches M. Tetrahedron: Asymmetr. 15 (2004) 1813-1817
32. Marchetti M., and Paganelli S. Chim. Ind. 87 (2005) 44-46
33. Leonard Jr. W.J., Vijai K.K., and Foster J.F. J. Biol. Chem. 238 (1963) 1984-1988
34. Wilting J., Weideman M.M., Roomer A.C., and Perrin J.H. Biochim. Biophys. Acta 579 (1979) 469-473
35. Krag-Hansen U. Pharmacol. Rev. 33 (1981) 17-53