OsO4-catalyzed dihydroxylation of olefins in ionic liquid [emim]BF4: A recoverable and reusable osmium

Tetrahedron Letters

Volumn 43, Issue 38, 2002, Pages 6849-6851

  Yanada, Reiko ^a   Takemoto, Yoshiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

emin BF4; Dihydroxylation; Ionic liquid; Olefin; OsO4

Indexed keywords

ALKENE DERIVATIVE; OSMIUM; OSMIUM TETRAOXIDE;

ARTICLE; CATALYSIS; CATALYST; DIHYDROXYLATION; IMMOBILIZATION; LIQUID; TOXICITY;

EID: 0037119674     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01461-2     Document Type: Article

References (26)

1. Reviews: (a) Welton, T. Chem. Rev. 1999, 99, 2071-2083; (b) Wasserscheid, P.; Wilhelm, K. Angew. Chem., Int. Ed. Engl. 2000, 39, 3772-3789; (c) Sheldon, R. Chem. Commun. 2001, 2399-2407. Recently, ionic liquids have become very attractive as novel reaction media toward green chemistry. (a) Reynolds, J. L.; Erdner, K. R.; Jones, P. B. Org. Lett. 2002, 4, 917-919; (b) Ansari, I. A.; Gree, R. Org. Lett. 2002, 4, 1507-1509; (c) Mayo, K. G.; Nearhoof, E. H.; Kiddle, J. J. Org. Lett. 2002, 4, 1567-1570; (d) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691-1694; (e) Sémeril, D.; Olivier-Bourbigou, H.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 2002, 146-147; (f) Consorti, C. S.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753-755; (g) Nara, S. J.; Harjani, J. R.; Salunkhe, M. M. Tetrahedron Lett. 2002, 43, 2979-2982.
2. Reviews: (a) Welton, T. Chem. Rev. 1999, 99, 2071-2083; (b) Wasserscheid, P.; Wilhelm, K. Angew. Chem., Int. Ed. Engl. 2000, 39, 3772-3789; (c) Sheldon, R. Chem. Commun. 2001, 2399-2407. Recently, ionic liquids have become very attractive as novel reaction media toward green chemistry. (a) Reynolds, J. L.; Erdner, K. R.; Jones, P. B. Org. Lett. 2002, 4, 917-919; (b) Ansari, I. A.; Gree, R. Org. Lett. 2002, 4, 1507-1509; (c) Mayo, K. G.; Nearhoof, E. H.; Kiddle, J. J. Org. Lett. 2002, 4, 1567-1570; (d) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691-1694; (e) Sémeril, D.; Olivier-Bourbigou, H.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 2002, 146-147; (f) Consorti, C. S.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753-755; (g) Nara, S. J.; Harjani, J. R.; Salunkhe, M. M. Tetrahedron Lett. 2002, 43, 2979-2982.
3. Reviews: (a) Welton, T. Chem. Rev. 1999, 99, 2071-2083; (b) Wasserscheid, P.; Wilhelm, K. Angew. Chem., Int. Ed. Engl. 2000, 39, 3772-3789; (c) Sheldon, R. Chem. Commun. 2001, 2399-2407. Recently, ionic liquids have become very attractive as novel reaction media toward green chemistry. (a) Reynolds, J. L.; Erdner, K. R.; Jones, P. B. Org. Lett. 2002, 4, 917-919; (b) Ansari, I. A.; Gree, R. Org. Lett. 2002, 4, 1507-1509; (c) Mayo, K. G.; Nearhoof, E. H.; Kiddle, J. J. Org. Lett. 2002, 4, 1567-1570; (d) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691-1694; (e) Sémeril, D.; Olivier-Bourbigou, H.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 2002, 146-147; (f) Consorti, C. S.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753-755; (g) Nara, S. J.; Harjani, J. R.; Salunkhe, M. M. Tetrahedron Lett. 2002, 43, 2979-2982.
4. Reviews: (a) Welton, T. Chem. Rev. 1999, 99, 2071-2083; (b) Wasserscheid, P.; Wilhelm, K. Angew. Chem., Int. Ed. Engl. 2000, 39, 3772-3789; (c) Sheldon, R. Chem. Commun. 2001, 2399-2407. Recently, ionic liquids have become very attractive as novel reaction media toward green chemistry. (a) Reynolds, J. L.; Erdner, K. R.; Jones, P. B. Org. Lett. 2002, 4, 917-919; (b) Ansari, I. A.; Gree, R. Org. Lett. 2002, 4, 1507-1509; (c) Mayo, K. G.; Nearhoof, E. H.; Kiddle, J. J. Org. Lett. 2002, 4, 1567-1570; (d) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691-1694; (e) Sémeril, D.; Olivier-Bourbigou, H.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 2002, 146-147; (f) Consorti, C. S.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753-755; (g) Nara, S. J.; Harjani, J. R.; Salunkhe, M. M. Tetrahedron Lett. 2002, 43, 2979-2982.
5. Reviews: (a) Welton, T. Chem. Rev. 1999, 99, 2071-2083; (b) Wasserscheid, P.; Wilhelm, K. Angew. Chem., Int. Ed. Engl. 2000, 39, 3772-3789; (c) Sheldon, R. Chem. Commun. 2001, 2399-2407. Recently, ionic liquids have become very attractive as novel reaction media toward green chemistry. (a) Reynolds, J. L.; Erdner, K. R.; Jones, P. B. Org. Lett. 2002, 4, 917-919; (b) Ansari, I. A.; Gree, R. Org. Lett. 2002, 4, 1507-1509; (c) Mayo, K. G.; Nearhoof, E. H.; Kiddle, J. J. Org. Lett. 2002, 4, 1567-1570; (d) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691-1694; (e) Sémeril, D.; Olivier-Bourbigou, H.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 2002, 146-147; (f) Consorti, C. S.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753-755; (g) Nara, S. J.; Harjani, J. R.; Salunkhe, M. M. Tetrahedron Lett. 2002, 43, 2979-2982.
6. Reviews: (a) Welton, T. Chem. Rev. 1999, 99, 2071-2083; (b) Wasserscheid, P.; Wilhelm, K. Angew. Chem., Int. Ed. Engl. 2000, 39, 3772-3789; (c) Sheldon, R. Chem. Commun. 2001, 2399-2407. Recently, ionic liquids have become very attractive as novel reaction media toward green chemistry. (a) Reynolds, J. L.; Erdner, K. R.; Jones, P. B. Org. Lett. 2002, 4, 917-919; (b) Ansari, I. A.; Gree, R. Org. Lett. 2002, 4, 1507-1509; (c) Mayo, K. G.; Nearhoof, E. H.; Kiddle, J. J. Org. Lett. 2002, 4, 1567-1570; (d) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691-1694; (e) Sémeril, D.; Olivier-Bourbigou, H.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 2002, 146-147; (f) Consorti, C. S.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753-755; (g) Nara, S. J.; Harjani, J. R.; Salunkhe, M. M. Tetrahedron Lett. 2002, 43, 2979-2982.
7. Reviews: (a) Welton, T. Chem. Rev. 1999, 99, 2071-2083; (b) Wasserscheid, P.; Wilhelm, K. Angew. Chem., Int. Ed. Engl. 2000, 39, 3772-3789; (c) Sheldon, R. Chem. Commun. 2001, 2399-2407. Recently, ionic liquids have become very attractive as novel reaction media toward green chemistry. (a) Reynolds, J. L.; Erdner, K. R.; Jones, P. B. Org. Lett. 2002, 4, 917-919; (b) Ansari, I. A.; Gree, R. Org. Lett. 2002, 4, 1507-1509; (c) Mayo, K. G.; Nearhoof, E. H.; Kiddle, J. J. Org. Lett. 2002, 4, 1567-1570; (d) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691-1694; (e) Sémeril, D.; Olivier-Bourbigou, H.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 2002, 146-147; (f) Consorti, C. S.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753-755; (g) Nara, S. J.; Harjani, J. R.; Salunkhe, M. M. Tetrahedron Lett. 2002, 43, 2979-2982.
8. Reviews: (a) Welton, T. Chem. Rev. 1999, 99, 2071-2083; (b) Wasserscheid, P.; Wilhelm, K. Angew. Chem., Int. Ed. Engl. 2000, 39, 3772-3789; (c) Sheldon, R. Chem. Commun. 2001, 2399-2407. Recently, ionic liquids have become very attractive as novel reaction media toward green chemistry. (a) Reynolds, J. L.; Erdner, K. R.; Jones, P. B. Org. Lett. 2002, 4, 917-919; (b) Ansari, I. A.; Gree, R. Org. Lett. 2002, 4, 1507-1509; (c) Mayo, K. G.; Nearhoof, E. H.; Kiddle, J. J. Org. Lett. 2002, 4, 1567-1570; (d) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691-1694; (e) Sémeril, D.; Olivier-Bourbigou, H.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 2002, 146-147; (f) Consorti, C. S.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753-755; (g) Nara, S. J.; Harjani, J. R.; Salunkhe, M. M. Tetrahedron Lett. 2002, 43, 2979-2982.
9. Reviews: (a) Welton, T. Chem. Rev. 1999, 99, 2071-2083; (b) Wasserscheid, P.; Wilhelm, K. Angew. Chem., Int. Ed. Engl. 2000, 39, 3772-3789; (c) Sheldon, R. Chem. Commun. 2001, 2399-2407. Recently, ionic liquids have become very attractive as novel reaction media toward green chemistry. (a) Reynolds, J. L.; Erdner, K. R.; Jones, P. B. Org. Lett. 2002, 4, 917-919; (b) Ansari, I. A.; Gree, R. Org. Lett. 2002, 4, 1507-1509; (c) Mayo, K. G.; Nearhoof, E. H.; Kiddle, J. J. Org. Lett. 2002, 4, 1567-1570; (d) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691-1694; (e) Sémeril, D.; Olivier-Bourbigou, H.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 2002, 146-147; (f) Consorti, C. S.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753-755; (g) Nara, S. J.; Harjani, J. R.; Salunkhe, M. M. Tetrahedron Lett. 2002, 43, 2979-2982.
10. Reviews: (a) Welton, T. Chem. Rev. 1999, 99, 2071-2083; (b) Wasserscheid, P.; Wilhelm, K. Angew. Chem., Int. Ed. Engl. 2000, 39, 3772-3789; (c) Sheldon, R. Chem. Commun. 2001, 2399-2407. Recently, ionic liquids have become very attractive as novel reaction media toward green chemistry. (a) Reynolds, J. L.; Erdner, K. R.; Jones, P. B. Org. Lett. 2002, 4, 917-919; (b) Ansari, I. A.; Gree, R. Org. Lett. 2002, 4, 1507-1509; (c) Mayo, K. G.; Nearhoof, E. H.; Kiddle, J. J. Org. Lett. 2002, 4, 1567-1570; (d) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691-1694; (e) Sémeril, D.; Olivier-Bourbigou, H.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 2002, 146-147; (f) Consorti, C. S.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753-755; (g) Nara, S. J.; Harjani, J. R.; Salunkhe, M. M. Tetrahedron Lett. 2002, 43, 2979-2982.
11. Kolb H.C., VanNieuwenhze M.S., Sharpless K.B. Chem. Rev. 94:1994;2483-2547.
12. Vanrheenen V., Kelly R.C., Cha D.Y. Tetrahedron Lett. 17:1976;1973-1976.
13. Döbler C., Mehltretter G., Beller M. Angew. Chem., Int. Ed. Engl. 38:1999;3026-3028.
14. Jonsson S.Y., Färnegårdh K., Bäckvall J.-E. J. Am. Chem. Soc. 123:2001;1365-1371.
15. Nagayama S., Endo M., Kobayashi S. J. Org. Chem. 63:1998;6094-6095.
16. Kobayashi S., Endo M., Nagayama S. J. Am. Chem. Soc. 121:1999;11229-11230.
17. Severeyns A., De Vos D.E., Fiermans L., Verpoort F., Grobert P.J., Jacobs P.A. Angew. Chem., Int. Ed. Engl. 40:2001;586-589.
18. Choudary B.M., Chowdari N.S., Kantam M.L., Raghavan K.V. J. Am. Chem. Soc. 123:2001;9220-9221.
19. Choudary B.M., Chowdari N.S., Madhi S., Kantam M.L. Angew. Chem., Int. Ed. Engl. 40:2001;4620-4623.
20. Choudary B.M., Chowdari N.S., Jyothi K., Kumar N.S., Kantam M.L. Chem. Commun. 2002;586-587.
21. Choudary B.M., Chowdari N.S., Jyothi K., Kantam M.L. J. Am. Chem. Soc. 124:2002;5341-5349.
22. 6/water/t-BuOH for dihydroxylation of olefins was reported. Q. Yao. Org. Lett. 2002, 4, 2197-2199.
23. 4 was able to be recovered almost quantitatively and was able to be reused for the next dihydroxylation.
24. Sharpless K.B., Akashi K. J. Am. Chem. Soc. 98:1976;1986-1987.
25. 4 on the bottom of the septum of the reaction vessel after 3 months.
26. Ethyl acetate solution of olefins was used instead of liquid olefins when olefins were powder or crystals in order to avoid overoxidation of diols. Ethyl acetate was then removed under reduced pressure. Then the residue was similarly stirred.