Efficient aerobic oxidation of alcohols using a novel combination N-hydroxy phthalimide (NHPI) and a recyclable heterogeneous cobalt complex

Journal of Molecular Catalysis A: Chemical

Volumn 232, Issue 1-2, 2005, Pages 95-99

  Rajabi, Fatemeh ^a   Karimi, Babak ^b,c  

^a SHARIF UNIVERSITY OF TECHNOLOGY   (Iran)

^b INSTITUTE FOR ADVANCED STUDIES IN BASIC SCIENCES IASBS   (Iran)

^c Institute for Fundamental Research   (Iran)

Author keywords

Alcohols; Molecular oxygen; N hydroxy phthalimide; Oxidation; Supported reagents

Indexed keywords

ALCOHOLS; CATALYSIS; OXIDATION; REACTION KINETICS; THERMODYNAMIC STABILITY;

AEROBIC OXIDATION; CARBONYL COMPOUNDS;

COBALT;

ALCOHOL DERIVATIVE; CARBONYL DERIVATIVE; COBALT COMPLEX; N HYDROXYPHTHALIMIDE; PHTHALIMIDE DERIVATIVE; SILICON DIOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; OXIDATION; THERMOSTABILITY;

EID: 15044352860     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2005.01.016     Document Type: Article

References (61)

1. R.A. Sheldon, and J.K. Kochi Metal-Catalyzed Oxidation of Organic Compounds 1984 Academic Press New York
2. M. Hudlicky Oxidations in Organic Chemistry, ACS Monograph Series 1990 American Chemical Society Washington, DC
3. For a review on metal-mediated oxidations, see: W.J. Mijs, and C.R.H. de Jonge Organic Syntheses by Oxidation with Metal Compounds 1986 Plenum New York
4. R.A. Sheldon L.L. Simandi Dioxygem Activation and Homogeneous Catalytic Oxidation 1991 Elsevier Amsterdam 573
5. B.R. James L.L. Simandi Dioxygem Activation and Homogeneous Catalytic Oxidation 1991 Elsevier Amsterdam 195
6. Ruthenium catalyst
7. R. Tang, S.E. Diamond, N. Neary, and F. Mares J. Chem. Soc. Chem. Commun. 1978 562
8. M. Matsumoto, and N. Watanabe J. Org. Chem. 49 1984 3435
9. C. Bilgrien, S. Davis, and R.S. Drago J. Am. Chem. Soc. 109 1987 3786
10. J.-E. Backvall, R.L. Chowdhury, and U. Karlsson J. Chem. Soc., Chem. Commun. 1991 473
11. S.-I. Murahashi, T. Naota, and J. Hirai J. Org. Chem. 58 1993 7318
12. G.Z. Wang, U. Andreasson, and J.-E. Backvall J. Chem. Soc., Chem. Commun. 1994 1037
13. T. Inokuchi, K. Nakagawa, and S. Torii Tetrahedron Lett. 36 1995 3223
14. I.E. Marko, P.R. Giles, M. Tsukazaki, M.I. Chelle-Regnaut, C.J. Urch, and S.M. Brown J. Am. Chem. Soc. 119 1997 12661
15. R. Lenz, and S.V. Ley J. Chem. Soc., Perkin Trans. 1 1997 3291
16. A. Hanyu, E. Takezawa, S. Sakaguchi, and Y. Ishii Tetrahedron Lett. 39 1998 5557
17. K. Kaneda, T. Ya-mashita, T. Matsushita, and K. Ebitani J. Org. Chem. 63 1998 1750
18. Copper catalysts
19. I.E. Marko, P.R. Giles, M. Tsukazaki, M.I. Chelle-Regnaut, C.J. Urch, and S.M. Brown J. Org. Chem. 63 1998 1756 (and the references cited therein)
20. Cobalt catalysts
21. T. Yamada, and T. Mukaiyama Chem. Lett. 1989 519
22. A.K. Mandal, and J. Iqbal Tetrahedron Lett. 53 1997 7641
23. T. Iwahama, S. Sakaguchi, Y. Nishiyama, and Y. Ishii Tetrahedron Lett. 36 1995 6923
24. Other metals
25. M.F. Semmelhack, C.R. Schmidt, D.A. Cortes, and C.S. Chou J. Am. Chem. Soc. 106 1984 3374
26. K.S. Coleman, M. Coppe, C. Thomas, and J.A. Osborn Tetrahedron Lett. 40 1999 3723
27. For examples of Pd(II)-catalyzed aerobic oxidations, see
28. M.J. Schultz, C. vPark, and M. Sigman Chem. Commun. 2002 3034
29. G.J. Ten Brink, I.W.C.E. Arends, and R.A. Sheldon Adv. Synth. Catal. 344 2002 355
30. N. Kakiuchi, Y. Maeda, T. Nishimura, and S. Uemura J. Org. Chem. 66 2001 6620
31. G.J. Ten Brink, I.W.C.E. Arends, and R.A. Sheldon Science 287 2000 1636
32. T. Nishimura, T. Onoue, K. Ohe, and S. Uemura Tetrahedron Lett. 39 1998 6011
33. K. Yamaguchi, and N. Mizuno Angew. Chem. Int. Ed. 41 2002 4538
34. T.F. Blackburn, and J. Schwartz J. Chem. Soc., Chem. Commun. 1977 158
35. K. Kaneda, Y. Fujie, and K. Ebitani Tetrahedron Lett. 38 1997 9023
36. K.P. Peterson, and R.C. Larock J. Org. Chem. 63 1998 3185
37. For related examples of oxidative kinetic resolutions, see
38. E.M. Ferreira, and B.M. Stoltz J. Am. Chem. Soc. 123 2001 7725
39. J.T. Bagdanoff, E.M. Ferreira, and B.M. Stoltz Org. Lett. 5 2003 835
40. S.K. Mandal, D.R. Jensen, J.S. Pugsley, and M.S. Sigman J. Org. Chem. 68 2003 4600
41. For example of Pd-catalyzed oxidation of alcohols using dichloroethane (DCE) see
42. G. Rothenberg, S. Humbel, and J. Muzart J. Chem. Soc., Perkin Trans. 2 2001 1998
43. For reviews aerobic oxidation of alcohols see
44. B.-Z. Zhan, and A. Thompson Tetrahedron 60 2004 2917
45. T. Mallat, and A. Baiker Chem. Rev. 104 2004 3037
46. J. Muzart Tetrahedron 59 2003 5789
47. Y. Ishii, S. Sakaguchi, and T. Iwahama Adv. Synth. Catal. 343 2001 379 for more recent leading references see
48. S. Isozaki, Y. Nishiwaki, S. Sakaguchi, and Y. Ishii Chem. Commun. 2001 1352
49. S. Sakaguchi, Y. Nishiwaki, T. Kitamura, and Y. Ishii Angew. Chem. Int. Ed. 40 2001 222
50. Y. Nishiwaki, S. Sakaguchi, and Y. Ishii J. Org. Chem. 67 2002 5663
51. S. Sakaguchi, A. Shibamoto, and Y. Ishii Chem. Commun. 2002 180
52. S. Yamamoto, S. Sakaguchi, and Y. Ishii Green Chem. 5 2003 300
53. S. Sakaguchi, T. Hirabayashi, and Y. Ishii Chem. Commun. 2002 516
54. T. Iwahama, Y. Yoshino, T. Keitoku, S. Sakaguchi, and Y. Ishii J. Org. Chem. 65 2000 6502
55. Z.L. Lu, E. Lindner, and H.A. Mayer Chem. Rev. 102 2002 3543
56. A.P. Wight, and M.E. Davis Chem. Rev. 102 2002 3589
57. D.E. De Vos, M. Dams, B.F. Sels, and P.A. Jacobs Chem. Rev. 102 2002 3615
58. N. Koshino, B. Saha, and J.H. Espenson J. Phys. Chem. A 107 2003 4262
59. B. Saha, N. Koshino, and J.H. Espenson J. Phys. Chem. A 108 2004 425
60. C. Ueda, M. Noyama, H. Ohmori, and M. Masui Chem. Pharm. Bull. 35 1987 1372
61. I.C. Chisem, J. Rafelt, M.T. Shieh, J. Chisem, J.H. Clark, R. Jachuck, D.J. Macquarrie, C. Ramshaw, and K. Scott Chem. Commun. 1998 1949