Oxygen transfer from sulfoxides: Selective oxidation of alcohols catalyzed by polyoxomolybdates

Journal of Organic Chemistry

Volumn 67, Issue 20, 2002, Pages 7075-7079

  Khenkin, Alexander M ^a   Neumann, Ronny ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

REACTION STEPS;

ALCOHOLS; ALDEHYDES; CATALYSTS; COMPLEXATION; ISOTOPES; KETONES; OXIDATION; REACTION KINETICS;

OXYGEN;

ALCOHOL DERIVATIVE; ALDEHYDE; ALKANOL; ALLYL ALCOHOL; BENZYL ALCOHOL; DIMETHYL SULFOXIDE; KETONE; METAL DERIVATIVE; MOLYBDENUM; OXYGEN; POLYMER; POLYOXOMOLYBDATE; SOLVENT; SULFOXIDE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; DESICCATION; ISOTOPE LABELING; OXIDATION; OXYGEN TRANSPORT; REACTION ANALYSIS;

EID: 0037019987     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0255577     Document Type: Article

References (51)

1. Sheldon, R. A.; Arends, I. W. C. E.; Dijksman, A. Catal. Today 2000, 57, 157-166.
2. (a) Matsumoto, M.; Ito, J. J. Chem. Soc., Chem. Commun. 1981, 907.
3. (b) Tang, R.; Diamond, S. E.; Neary, N.; Mares, F. J. Chem. Soc., Chem. Commun. 1978, 562.
4. (c) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786.
5. (d) Bäckvall, J.-E.; Chaudhury, R. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473.
6. (e) Wang, G.-Z.; Andreasson, U.; Bäckvall, J.-E. J. Chem. Soc., Chem. Commun. 1994, 1037.
7. (f) Hanyu, A.; Takezawa, E.; Sakaguchi, S. Ishii, Y. Tetrahedron Lett. 1998, 5557.
8. (g) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Chem. Commun. 1999, 1591.
9. (a) Blackburn, T. F.; Schartz, J. J. Chem. Soc., Chem. Commun. 1977, 157.
10. (b) Aït-Mohand, S.; Hénin, F.; Muzart, J. Tetrahedron Lett. 1995, 36, 2473.
11. (c) Aït-Mohand, S.; Muzart, J. J. Mol. Catal. A 1998, 129, 135.
12. (d) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011.
13. (a) Skibida, I. P.; Sakharov, A. M. Catal. Today 1996, 27, 187.
14. (b) Sakharov, A. M.; Skibida, I. P. J. Mol. Catal. 1988, 48, 157.
15. (c) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Brown, S. M.; Urch, C. J. Science 1996, 274, 2044.
16. (d) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I. Gautier, A.; Brown, S. M.; Urch, C. J. J. Org. Chem. 1999, 64, 2433.
17. (e) Marko, I. E.; Gautier, A.; Chellé-Regnaut, I.; Giles, P. R.; Tsukazaki, M.; Urch, C. J.; Brown, S. M. J. Org. Chem. 1998, 63, 7576.
18. Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S, M. J. Am. Chem. Soc. 1997, 119, 12661.
19. (b) Colemab, K. S.; Lorber, C. Y.; Osborn, J. A. Eur. J. Inorg. Chem. 1998, 1673.
20. (c) Coleman, K. S.; Coppe, M.; Thomas, C.; Osborn, J. A. Tetrahedron Lett. 1999, 40, 3723.
21. (d) Lenz, R.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 3291.
22. ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636.
23. Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. Tetrahedron Lett. 1995, 39, 6011.
24. Chen, J. D.; Lempers, H. E. B.; Sheldon, R. A. J. Chem. Soc., Faraday Trans. 1996, 92, 1807.
25. (a) Semmelhack, M. F.; Scmid, C. R.; Cortës, D. A.; Chou, C. S. J. Am. Chem. Soc. 1984, 106, 3374.
26. (b) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Chem. Commun. 1999, 1591.
27. (c) Ben-Daniel, R.; Alsters, P.; Neumann, R. J. Org. Chem. 2001, 66, 8650.
28. (d) Cecchetto, A.; Fontana, F.; Minisci, F.; Recupero, F. Tetrahedron Lett. 2001, 42, 6651.
29. (a) Mizuno, N.; Misono, M. Chem. Rev. 1998, 98, 199.
30. (b) Hill, C. L.; Prosser-McCartha, C. M. Coord. Chem. Rev. 1995, 143, 407.
31. (c) Kozhevnikov, I. V. Chem. Rev. 1998, 98, 171.
32. (d) Neumann, R. Prog. Inorg. Chem. 1998, 47, 317-370.
33. Neumann, R.; Levin, M. J. Org. Chem. 1991, 56, 5707.
34. (b) Khenkin, A. M.; Vigdergauz, I.; Neumann, R. Chem. Eur. J. 2000, 6, 875.
35. (a) Peterson, K. P.; Larock, R. C.; J. Org. Chem. 1998, 63, 3185.
36. (b) Van Benthem, R. A. T. M.; Hiemstra, H.; van Leeuwen, P. W. N. M.; Geus, J. W.; Speckamp, W. N. Angew. Chem., Int. Ed. Engl. 1995, 34, 457.
37. Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. J. Am. Chem. Soc. 2002, 124, 766.
38. (a) Mancuso, A. J.; Swern, D. Synthesis 1981, 165.
39. (b) Tidwell, T. T. Org. React. 1990, 39, 297.
40. (d) Tidwell, T. T. Synthesis 1990, 857-870.
41. (a) Kukushkin, V. Y. Coord. Chem. Rev. 1995, 139, 375.
42. (b) Arterburn, J. B.; Perry, M. C. Org. Lett. 1999, 1, 769.
43. (c) Coleman, K. S.; Bedel, L. J. L.; Osborn, J. A. C. R. Acad. Sci. IIc 2000, 3, 765.
44. (d) Lobler, C. Y.; Pauls, I.; Osborn, J. A. Bull Soc. Chim. Fr. 1996, 133, 755.
45. Filowitz, M.; Ho, R. K. C.; Klemperer, W. G.; Shum, W. Inorg. Chem. 1979, 18, 93.
46. 40, despite the lower rates, because the latter is a hydrate, which would complicate the interpretation of the results.
47. Bordwell, F. G. Pure Appl. Chem. 1977, 49, 963.
48. It is conceivable that the proton is delocalized around the polyoxomolybdate.
49. Tsigdinos, G. A.; Hallada, C. J. Inorg. Chem. 1968, 7, 437.
50. Okruszek, A. J. Labelled Compd. Radiopharm. 1983, 20, 741.
51. Bonin, A. M.; Glover, S. A.; Hammond, G. P. J. Chem. Soc., Perkin Trans. 2 1994, 1173.