OsO4 in ionic liquid [Bmim]PF6: A recyclable and reusable catalyst system for olefin dihydroxylation. Remarkable effect of DMAP

Organic Letters

Volumn 4, Issue 13, 2002, Pages 2197-2199

  Yao, Qingwei ^a  

^a NORTHERN ILLINOIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; OSMIUM TETRAOXIDE;

ARTICLE; CATALYSIS; CHEMISTRY; ENVIRONMENTAL PROTECTION; HYDROXYLATION; POLLUTION; SOLUTION AND SOLUBILITY;

ALKENES; CATALYSIS; CONSERVATION OF NATURAL RESOURCES; ENVIRONMENTAL POLLUTION; HYDROXYLATION; OSMIUM TETROXIDE; SOLUTIONS;

EID: 0037182673     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026172d     Document Type: Article

References (30)

1. Trost, B. M. Angew. Chem. 1995, 107, 285-307; Angew. Chem., Int. Ed. Engt. 1995, 34, 259-281.
2. Trost, B. M. Angew. Chem. 1995, 107, 285-307; Angew. Chem., Int. Ed. Engt. 1995, 34, 259-281.
3. For leading reviews and monographs on green chemistry, see: (a) Green Chemistry: Designing Chemistry for the Environment. ACS Symposium Series No. 626; Anastas, P. T., Williamson, T. C., Eds.; American Chemical Society: Washington, DC, 1996.
4. (b) Anastas, P. T.; Warner, J. Green Chemistry: Theory and Practice; Oxford University Press: New York, 1998.
5. (c) Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes; Anastas, P. T., Williamson, T. C., Eds.; Oxford University Press: New York, 1999.
6. For general discussions on homogeneous catalysts and their heterogenization, see: (a) Applied Homogeneous Catalysis with Organometallic Compounds; Cornil, B., Hermann, W. A., Eds.; Wiley-VCH: Weiheim, 1996; Chapter 3.1.
7. (b) Chiral Catalyst Immobilization and Recycling; De Vos, D. E., Vankelecom, I. F. J., Jacobs, P. A., Eds.; VCH: Weiheim, 2000.
8. (a) VanRheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 23, 1973-1976. For an early review, see:
9. (b) Schröder, M. Chem. Rev. 1980, 80, 7.
10. (a) Jacobsen, E. N.; Markó, I.; Mungall, W. S.; Schröder, G.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 1968-1970. For selected reviews on Sharpless asymmetric dihydroxylation, see:
11. (b) Kolb, H. C.; Van Niewenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
12. (c) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH: Weinheim, 2001; pp 357-398.
13. 4 is present in some stage of the catalytic cycle.
14. For a case study, see: Ahrgren, L.; Sdutin, L. Org. Proc. Res. Dev. 1997, 1, 425-427.
15. Cainelli, G.; Contento, M.; Manescalchi, F.; Plessi; L. Synthesis 1989, 45-47.
16. Herrmann, W. A.; Kratzer, R. M.; Blümel, J.; Friedrich, H. B.; Fischer, R. W.; Apperley, D. C.; Mink, J.; Berkesi, O. J. Mol. Catal., A 1997, 120, 197-205.
17. (a) Nagayama, S.; Endo, M.; Kobayashi, S. J. Org. Chem. 1998, 63, 6094-6095.
18. (b) Kobayashi, S.; Endo, M.; Nagayama, S. J. Am. Chem. Soc. 1999, 121, 11229-11230.
19. Kobayashi, S.; Ishida, T.; Akiyama, A. Org. Lett. 2001, 3, 2649-2652.
20. Severeyns, A.; De Vos, D. E.; Fiermans, L.; Verpoort, F.; Grobert, P. J.; Jacobs, P. A. Angew. Chem., Int. Ed. 2001, 40, 586-589.
21. (a) Choudary, B. M.; Chowdari, N. S.; Kantam, M. L.; Raghavan, K. V. J. Am. Chem. Soc. 2001, 123, 9220-9221.
22. (b) Choudary, B. M.; Chowdari, N. S.; Madhi, S.; Kantam, M. L. Angew. Chem., Int. Ed. 2001, 40, 4620-4623.
23. Choudary, B. M.; Chowdari, N. S.; Jyothi, K.; Kumar, N. S.; Kantam, M. L. Chem. Commun. 2002, 586-587. (c)
24. (d) Choudary, B. M.; Chowdari, N. S.; Jyothi, K.; Kantam, M. L.; J. Am. Chem. Soc. 2002, 124, 5341-5349.
25. For recent reviews on ionic liquids and their application as innovative solvents in transition metal-catalyzed reactions, see: (a) Welton, T. Chem. Rev. 1999, 99, 2071-2083.
26. (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789.
27. Sheldon, R. Chem. Commun. 2001, 2399-2407.
28. 6 is essentially immiscible with either solvent, a completely homogeneous mixture was formed upon addition of NMO and the olefin under these conditions.
29. 3, a deep orange-red complex was immediately formed: (Matrix Presented)
30. 6 can either be purchased from Acros Organics at relatively low cost or readily made in large quantities by simple procedures.