A cartridge system for organometallic catalysis: Sequential catalysis and separation using supercritical carbon dioxide to switch phases

Angewandte Chemie - International Edition

Volumn 44, Issue 15, 2005, Pages 2291-2295

  Solinas, Maurizio ^a   Jiang, Jingyang ^a,c,d   Stelzer, Othmar ^c   Leitner, Walter ^a,b  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^c UNIVERSITY OF WUPPERTAL   (Germany)

^d DALIAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Green chemistry; Homogeneous catalysis; Phosphine ligands; Rhodium supercritical fluids

Indexed keywords

CARBON DIOXIDE; CATALYSIS; ORGANOMETALLICS; PHASE TRANSITIONS; POLYETHYLENE GLYCOLS; PRECIPITATION (CHEMICAL); RHODIUM; SCANDIUM COMPOUNDS; SEPARATION;

ORGANOMETALLIC CATALYSTS; PHOSPHINE LIGANDS; REACTION MIXTURE; SWITCH PHASES;

CATALYSTS;

1 OCTENE; 1-OCTENE; ALKENE; CARBON DIOXIDE; MACROGOL DERIVATIVE; ORGANOMETALLIC COMPOUND; PHOSPHINE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; METHODOLOGY; PHASE TRANSITION; SUPERCRITICAL FLUID CHROMATOGRAPHY;

ALKENES; CARBON DIOXIDE; CATALYSIS; CHEMISTRY, ANALYTICAL; CHROMATOGRAPHY, SUPERCRITICAL FLUID; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PHASE TRANSITION; PHOSPHINES; POLYETHYLENE GLYCOLS;

EID: 17644424685     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461768     Document Type: Article

References (34)

1. a) Transition Metals for Organic Synthesis (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 1998;
2. b) Applied Homogeneous Catalysis with Organometallic Compounds (Eds.: B. Cornils, W. A. Herrmann), 2nd ed., Wiley-VCH, Weinheim, 2000.
3. a) Green Chemistry: Theory and Practice (Eds.: P. T. Anastas, J. Warner), Oxford University Press, Oxford, 1998;
4. b) R. A. Sheldon, Pure Appl. Chem. 2000, 72, 1233-1246;
5. c) P. T. Anastas, M. M. Kirchhoff, Acc. Chem. Res. 2002, 35, 686-694.
6. a) R. T. Baker, W. Tumas, Science 1999, 284, 1477-1479;
7. b) D. J. Cole-Hamilton, Science 2003, 299, 1702-1706;
8. c) Aqueous-Phase Organometallic Catalysis (Eds.: B. Cornils, W. A. Herrmann), 2nd ed., Wiley-VCH, Weinheim, 2004.
9. a) D. E. Bergbreiter, Chem. Rev. 2002, 102, 3345-3384;
10. b) Z. Jin, Y. Wang, X. Zheng in Aqueous-Phase Organometallic Catalysis (Eds.: B. Cornus, W. A. Herrmann), 2nd ed., Wiley-VCH, Weinheim, 2004, pp. 301-311.
11. a) D. E. Bergbreiter, R. Chandran, J. Am. Chem. Soc. 1987, 109, 174-179;
12. b) D. E. Bergbreiter, L. Zhang, V. M. Mariagnanam, J. Am. Chem. Soc. 1993, 115, 9295-9296;
13. c) E. A. Karakhanov, E. A. Runova, G. V. Berezkin, E. B. Neimerovets, Macromol. Symp. 1994, 50, 231-240.
14. a) M. Wende, J. A. Gladysz, J. Am. Chem. Soc. 2003, 125, 5861-5872;
15. b) V. K. Dioumaev, R. M. Bullock, Nature 2004, 434, 530-532.
16. a) T. Malmström, C. Andersson, J. Mol. Catal. A 1997, 116, 237-245;
17. b) D. E. Bergbreiter, Y.-S. Liu, Tetrahedron Lett. 1997, 38, 3703-3706.
18. a) Chemical Synthesis Using Supercritical Fluids (Eds.: P. G. Jessop, W. Leitner), Wiley-VCH, Weinheim, 1999;
19. b) W. Leitner, Acc. Chem. Res. 2002, 35, 746-756.
20. a) D. Koch, W. Leitner, J. Am. Chem. Soc. 1998, 120, 13398-13404;
21. b) S. Kainz, A. Brinkmann, W. Leitner, A. Pfaltz, J. Am. Chem. Soc. 1999, 121, 6421-6429;
22. c) G. Franciò, K. Wittmann, W. Leitner, J. Organomet. Chem. 2001, 621, 130-142;
23. d) W. Leitner, A. M. Scurto in Aqueous-Phase Organometallic Catalysis (Eds.: B. Cornils, W. A. Herrmann), 2nd ed., Wiley-VCH, Weinheim, 2004, pp. 665-685.
24. a) M. F. Sellin, D. J. Cole-Hamilton, J. Chem. Soc. Dalton Trans. 2000, 11, 1681-1683;
25. b) C. D. Ablan, J. P. Hallett, K. N. West, R. S. Jones, C. A. Eckert, C. L. Liotta, P. G. Jessop, Chem. Commun. 2003, 2972-2973;
26. c) M. Wei, G. T. Musie, D.H. Busch, B. Subramaniam, J. Am. Chem. Soc. 2002, 124, 2513-2517;
27. d) G. B. Combes, F. Dehghani, F. P. Lucien, A. K. Dillow, N. R. Foster in Reaction Engineering for Pollution Prevention (Eds.: M. A. Abraham, R. P. Hesketh), Elsevier Science, Dordrecht, 2000, pp. 173-181;
28. e) P. B. Webb, D. J. Cole-Hamilton, Chem. Commun. 2004, 612-613.
29. For examples of sequential catalytic reactions of different olefins on polymer-bound heterogenized rhodium catalysts, see: a) A. J. Sandee, J. N. H. Reek, P. C. J. Kamer, P. van Leeuwen, J. Am. Chem. Soc. 2001, 123, 8468-8476; b) F. Shibahara, K. Nozaki, T. Hiyama, J. Am. Chem. Soc. 2003, 125, 8555-8560.
30. For examples of sequential catalytic reactions of different olefins on polymer-bound heterogenized rhodium catalysts, see: a) A. J. Sandee, J. N. H. Reek, P. C. J. Kamer, P. van Leeuwen, J. Am. Chem. Soc. 2001, 123, 8468-8476; b) F. Shibahara, K. Nozaki, T. Hiyama, J. Am. Chem. Soc. 2003, 125, 8555-8560.
31. For this reason in his pioneering work on natural product extraction, Kurt Zosel referred to supercritical-fluid extraction as "Destraktion" , an artificial word composed from Latin "destillare" and "extrahere". K. Zosel, Angew. Chem. 1978, 90, 748; Angew. Chem. Int. Ed. Engl. 1978, 17, 702.
32. For this reason in his pioneering work on natural product extraction, Kurt Zosel referred to supercritical-fluid extraction as "Destraktion" , an artificial word composed from Latin "destillare" and "extrahere". K. Zosel, Angew. Chem. 1978, 90, 748; Angew. Chem. Int. Ed. Engl. 1978, 17, 702.
33. 1H} NMR δ = -21.1 ppm.
34. 2, where the selectivity and activity were found to decrease significantly upon recycling.