Copper(II) catalyzed selective oxidation of primary alcohols to aldehydes with atmospheric oxygen

Tetrahedron Letters

Volumn 47, Issue 6, 2006, Pages 923-926

  Velusamy, Subbarayan ^a   Srinivasan, Arumugam ^a   Punniyamurthy, T ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

Alcohol; Catalyst; Copper(II) complex; Oxidation; Selective

Indexed keywords

ALCOHOL; ALDEHYDE; COPPER COMPLEX; OXYGEN; TOLUENE;

ALCOHOL OXIDATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE;

EID: 30344485161     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.11.149     Document Type: Article

References (46)

1. M. Beller C. Bolm Transition Metals for Organic Synthesis Vol. 2 1998 Wiley-VCH Weinheim 350 360
2. R.A. Sheldon, and J.K. Kochi Metal-Catalyzed Oxidations of Organic Compounds 1981 Academic Press New York
3. B.M. Trost I. Fleming S.V. Ley Comprehensive Organic Synthesis Vol. 7 1991 Pergamon Oxford 251 325
4. G. Cainelli, and G. Cardillo Chromium Oxidations in Organic Chemistry 1984 Springer Berlin
5. T. Punniyamurthy, S. Velusamy, and J. Iqbal Chem. Rev. 105 2005 2329
6. T. Mallat, and A. Baiker Chem. Rev. 104 2004 3037
7. S.S. Stahl Angew. Chem., Int. Ed. 43 2004 3400
8. M. Kirihara, Y. Ochiai, S. Takizawa, H. Takahata, and H. Nemoto Chem. Commun. 1999 1387
9. Y. Maeda, N. Kakiuchi, S. Matsumura, T. Nishimura, T. Kawamura, and S. Uemura J. Org. Chem. 67 2002 6718
10. S.R. Reddy, S. Das, and T. Punniyamurthy Tetrahedron Lett. 44 2004 3561
11. T. Yamada, and T. Mukaiyama Chem. Lett. 1989 519
12. T. Iwahama, Y. Yoshino, T. Keitoku, S. Sakaguchi, and Y. Ishii J. Org. Chem. 65 2000 6502
13. I.E. Marko, A. Gautier, R. Dumeunier, K. Doda, F. Philippart, S.M. Brown, and J. Urch Angew. Chem., Int. Ed. 43 2004 1588
14. R.C. Pratt, and T.D.P. Stack J. Am. Chem. Soc. 125 2003 8716
15. P. Chaudhuri, M. Hess, T. Weyhermuller, and K. Wieghardt Angew. Chem., Int. Ed. 38 1999 1095
16. P. Gamez, I.W.C.E. Arends, J. Reedijk, and R.A. Sheldon Chem. Commun. 2003 2414
17. E. Saint-Aman, S. Menage, J.-L. Pierre, E. Defrancq, and G. Gellon New. J. Chem. 1998 393
18. S. Velusamy, M. Ahamed, and T. Punniyamurthy Org. Lett. 6 2004 4821
19. H. Egami, S. Onitsuka, and T. Katsuki Tetrahedron Lett. 46 2005 6049
20. H. Egami, H. Shimizu, and T. Katsuki Tetrahedron Lett. 46 2005 783
21. H. Shimizu, S. Onitsuka, H. Egami, and T. Katsuki J. Am. Chem. Soc. 127 2005 5396
22. T. Matsushita, K. Ebitani, and K. Kaneda Chem. Commun. 1999 265
23. B. Hinzen, R. Lenz, and S.V. Ley Synthesis 1998 977
24. K. Yamaguchi, K. Mori, T. Mizugaki, K. Ebitani, and K. Kaneda J. Am. Chem. Soc. 122 2000 7144
25. I.E. Marko, P.R. Giles, M. Tsukazaki, I. Chelle-Regnaut, C.J. Urch, and S.M. Brown J. Am. Chem. Soc. 119 1997 12661
26. A. Dijksman, I.W.C.E. Arends, and R.A. Sheldon Chem. Commun. 1999 1591
27. G. Csjernyik, A.H. Ell, L. Fadini, B. Pugin, and J.-E. Backvall J. Org. Chem. 67 2002 1657
28. J. Martin, C. Martin, M. Faraj, and M. Bregeault Nouv. J. Chim. 8 1984 141
29. K. Kaneda, M. Fujii, and K. Morioka J. Org. Chem. 61 1996 4502
30. T. Nishimura, T. Onoue, K. Ohe, and S. Uemura J. Org. Chem. 64 1999 6750
31. K.P. Peterson, and R.C. Larock J. Org. Chem. 63 1998 3185
32. G.-J. ten Brink, I.W.C.E. Arends, and R.A. Sheldon Science 287 2000 1636
33. Y. Uozumi, and R. Nakao Angew. Chem., Int. Ed. 42 2003 194
34. M.J. Schultz, S.S. Hamilton, D.R. Jensen, and M.S. Sigman J. Org. Chem. 70 2005 3343
35. T. Nishimura, N. Kakiuchi, M. Inoue, and S. Uemura Chem. Commun. 2000 1245
36. T. Iwasawa, M. Tokunaga, Y. Obora, and Y. Tsuji J. Am. Chem. Soc. 126 2004 6554
37. A. Haimov, and R. Neumann Chem. Commun. 2002 876
38. T. Mallat, and A. Baiker Catal. Today 19 1994 247
39. M. Musawir, P.N. Davey, G. Kelly, and I.V. Kozhevnikov Chem. Commun. 2003 1414
40. S. Velusamy, and T. Punniyamurthy Eur. J. Org. Chem. 2003 3913
41. S. Velusamy, and T. Punniyamurthy Tetrahedron Lett. 44 2003 8955
42. S. Velusamy, A.V. Kumar, R. Saini, and T. Punniyamurthy Tetrahedron Lett. 46 2005 3819
43. 13C), IR and mass analysis.
44. J. Laugier, J.-M. Latour, A. Caneschi, and P. Rey Inorg. Chem. 30 1991 4474
45. A. Caneschi, A. Grand, J. Laugier, P. Rey, and R. Subra J. Am. Chem. Soc. 110 1988 2307
46. Y. Wang, J.L. DuBois, B. Hedman, K.O. Hodgson, and T.D.P. Stack Science 279 1998 537