Synthesis of linear aldehydes from internal olefins in water

Chemical Communications

Volumn , Issue 17, 2005, Pages 2283-2285

  Klein, Holger ^a   Jackstell, Ralf ^a   Beller, Matthias ^a  

^a LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; ORGANIC SOLVENT; WATER;

ARTICLE; CARBONYLATION; CATALYST; PH; PRESSURE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 18844430846     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b418350a     Document Type: Article

References (36)

1. W. A. Herrmann and C. W. Kohlpaintner, Angew. Chem., 1993, 105, 1588-1609;
2. W. A. Herrmann and C. W. Kohlpaintner, Angew. Chem., Int. Ed. Engl., 1993, 32, 1524-1544.
3. (a) C. W. Kohlpaintner, R. W. Fischer and B. Cornils, Appl. Catal., A, 2001, 221, 219-225;
4. (b) B. Cornils, Org. Process Res. Dev., 1998, 2, 121-127;
5. (c) H.-W. Bohnen and B. Cornils, Adv. Catal., 2002, 47, 1-64.
6. For solubility data of olefins in water, see: Hydrocarbons with Water and Sea Water, ed. D. G. Shaw, M.-C. Hauclait-Pirson, G. T. Hefter and A. Maczynski, IUPAC Solubility Data Series, vol. 37 and 38, Pergamon Press, New York, 1989.
7. W. Keim, Green Chem., 2003, 5, 105-111.
8. W. Leitner, Pure Appl. Chem., 2004, 76, 635-644.
9. D. J. Adams, D. J. Cole-Hamilton, E. G. Hope, P. J. Pogorzelec and A. M. Stuart, J. Organomet. Chem., 2004, 689, 1413-1417.
10. (a) R. P. J. Bronger, S. M. Silva, P. C. J. Kamer and P. W. N. M. van Leeuwen, Dalton Trans., 2004, 1590-1596;
11. (b) A. Riisager, K. M. Eriksen, P. Wasserscheid and R. Fehrmann, Catal. Lett., 2003, 90, 149-153;
12. (c) P. Wasserscheid and W. Keim, Angew. Chem. Int. Ed., 2000, 39, 3773-3789.
13. M. Beller, B. Zimmermann and H. Geissler, Chem. Eur. J., 1999, 5, 1301-1305.
14. A. Seayad, M. Ahmed, H. Klein, R. Jackstell, T. Gross and M. Beller, Science, 2002, 297, 1676-1678.
15. (a) P. C. J. Kamer, J. N. H. Reek and P. W. N. M. van Leeuwen, in Rhodium Catalyzed Hydroformylation, ed. P. W. N. M. van Leeuwen and C. Claver, Kluwer Academic Publishers, Dordrecht, 2000, pp. 57-59;
16. (b) C. D. Frohning and C. W. Kohlpaintner, in Applied Homogeneous Catalysis with Organometallic Compounds, ed. B. Cornils, W. A. Herrmann, VCH, Weinheim, 1996, 1st edn., vol. 1, p. 40.
17. E. Billig, A. G. Abatjoglou and D. R. Bryant, (UCC) EP 213639, 1987, US 4748261, 1988.
18. P. M. Burke, J. M. Garner, K. A. Kreutzer, A. J. J. M. Teunissen, C. S. Snijder and C. B. Hansen, (DSM/Du Pont) WO 97/33854, 1997.
19. (a) L. A. van der Veen, P. C. J. Kamer and P. W. N. M. van Leeuwen, Angew. Chem., 1999, 111, 349-351;
20. L. A. van der Veen, P. C. J. Kamer and P. W. N. M. van Leeuwen, Angew. Chem. Int. Ed., 1999, 38, 336-338;
21. (b) L. A. van der Veen, P. C. J. Kamer and P. W. N. M. van Leeuwen, Organometallics, 1999, 18, 4765-4777.
22. D. Selent, D. Hess, K.-D. Wiese, D. Röttger, C. Kunze and A. Börner, Angew. Chem., 2001, 113, 1739-1741;
23. D. Selent, D. Hess, K.-D. Wiese, D. Röttger, C. Kunze and A. Börner, Angew. Chem. Int. Ed., 2001, 40, 1696-1698.
24. H. Klein, R. Jackstell, K.-D. Wiese, C. Borgmann and M. Beller, Angew. Chem., 2001, 113, 3505-3508;
25. H. Klein, R. Jackstell, K.-D. Wiese, C. Borgmann and M. Beller, Angew. Chem. Int. Ed., 2001, 40, 3408-3411.
26. K. Tamao, H. Yamamoto, H. Matsumoto, N. Miyake, T. Hayashi and M. Kumada, Tetrahedron Lett., 1977, 16, 1389-1392.
27. Mixture of the sodium salts of different regioisomers with a sulfonation degree between 6 and 8.
28. (a) H. Bahrmann, K. Bergrath, H.-J. Kleiner, P. Lappe, C. Naumann, D. Peters and D. Regnat, J. Organomet. Chem., 1996, 520, 97-100;
29. (b) H. Bahrmann, H. Bach, C. D. Frohning, H.-J. Kleiner, P. Lappe, D. Peters, D. Regnat and W. A. Herrmann, J. Mol. Catal. A: Chem., 1997, 116, 49-53.
30. 2 = 1:1) via a pressure regulator. After the reaction time the autoclave was cooled to room temperature and samples were taken from the organic phase and analyzed by gas chromatography. Products were identified by comparison with authentic samples.
31. For studies about the influence of the pH on the hydroformylation for terminal olefins, see: (a) R. M. Deshpande, Purwanto, H. Delmas and R. V. Chaudhari, J. Mol. Catal. A: Chem., 1997, 126, 133-140;
32. (b) E. Mieczýnska, A. M. Trzeciak and J. J. Ziołkowski, J. Mol. Catal. A: Chem., 1999, 148, 59-68.
33. F. Joó, J. Kovács, A. C. Bényei, L. Nádasdi and G. Laurenczy, Chem. Eur. J., 2001, 7, 193-199.
34. For other examples of the drastic influence of the pH value on catalytic reactions, see: (a) C. Döbler, G. Mehltretter and M. Beller, Angew. Chem., 1999, 111, 3211-3212;
35. C. Döbler, G Mehltretter and M. Beller, Angew. Chem. Int. Ed., 1999, 38, 3026-3028;
36. (b) C. Döbler, G. Mehltretter, U. Sundermeier and M. Beller, J. Am. Chem. Soc., 2000, 122, 10289-10297.