Mild peroxidative oxidation of cyclohexane catalyzed by mono-, di-, tri-, tetra- and polynuclear copper triethanolamine complexes

Advanced Synthesis and Catalysis

Volumn 348, Issue 1-2, 2006, Pages 159-174

  Kirillov, Alexander M ^a   Kopylovich, Maximilian N ^a   Kirillova, Marina V ^a   Karabach, Evgeny Yu ^a   Haukka, Matti ^b   Guedes Da Silva, M Fátima C ^a,c   Pombeiro, Armando J L ^a  

^a Center for Structural Chemistry   (Portugal)

^b UNIVERSITY OF EASTERN FINLAND   (Finland)

^c UNIVERSIDADE LUSÓFONA DE HUMANIDADES E TECNOLOGIAS   (Portugal)

Author keywords

Biphasic catalysis; Copper complexes; Cyclohexane; N,O ligands; Oxidation

Indexed keywords

EID: 31544473760     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200505216     Document Type: Article

References (66)

1. R. Whyman, Applied Organometallic Chemistry and Catalysis, Oxford University Press, Oxford, 2001.
2. A. E. Shilov, G. B. Shul'pin, Activation and Catalytic Reactions of Saturated Hydrocarbons in the Presence of Metal Complexes, Kluwer Academic Publishers, Dordrecht, The Netherlands, 2000.
3. Catalytic Activation and Functionalisation of Light Alkanes, (Eds.: E. D. Derouane, J. Haber, F. Lemos, F. Ramôa Ribeiro, M. Guinet), NATO ASI series, Vol. 44, Kluwer Academic Publ., Dordrecht, The Netherlands, 1998.
4. The Activation of Dioxygen and Homogeneous Catalytic Oxidation, (Eds.: D. Barton, A. E. Martell, D. T. Sawyer), Plenum Press, New York, 1993.
5. A. E. Shilov, G. B. Shul'pin, Chem. Rev. 1997, 97, 2879.
6. U. Schuchardt, D. Cardoso, R. Sercheli, R. Pereira, R. S. da Cruz, M. C. Guerreiro, D. Mandelli, E. V. Spinace, E. L. Pires, Appl. Catal. A: Gen. 2001, 211, 1.
7. J. M. Bregeault, Dalton Trans. 2003, 3289.
8. G. B. Shul'pin, J. Mol. Catal. A: Chem. 2002, 189, 39.
9. G. B. Shul'pin, G. V. Nizova, Y. N. Kozlov, I. G. Pechenkina, New J. Chem. 2002, 26, 1238.
10. U. Schuchardt, W. A. Carvalho, E. V. Spinace, Synlett 1993, 10, 713.
11. P. Gamez, P. G. Aubel, W. L. Driessen, J. Reedijk, Chem. Soc. Rev. 2001, 30, 376.
12. nd edn., 1999, pp. 469-534.
13. M. C. Mimmi, M. Gullotti, L. Santagostini, G. Battaini, E. Monzani, R. Pagliarin, G. Zoppellaro, L. Casella, Dalton Trans. 2004, 2192.
14. a) L. M. Mirica, X. Ottenwaelder, T. D. P. Stack, Chem. Rev. 2004, 104, 1013;
15. b) E. A. Lewis, W. B. Tolman, Chem. Rev. 2004, 104, 1047.
16. nd edn., Elsevier, 2003, Vol. 8, Ch. 8.15, pp. 369-393.
17. nd edn., Elsevier, 2003, Vol. 8, Ch. 8.17, pp. 437-457.
18. J. J. R. Fraústo da Silva, R. J. P. Williams, The Biological Chemistry of the Elements, Oxford University Press, Oxford, 2001.
19. E. I. Solomon, U. M. Sundaram, T. E. Machonkin, Chem. Rev. 1996, 96, 2563.
20. J. P. Klinman, Chem. Rev. 1996, 96, 2541.
21. M. Ayala, E. Torres, Appl. Catal. A: Gen. 2004, 272, 1.
22. S. J. Elliot, M. Zhu, L. Tso, H.-H. T. Nguyen, J. H.-K. Yip, S. I. Chan, J. Am. Chem. Soc. 1997, 119, 9949.
23. R. L. Lieberman, A. C. Rosenzweig, Critical Reviews in Biochemistry and Molecular Biology 2004, 39, 147.
24. R. L. Lieberman, A. C. Rosenzweig, Nature 2005, 434, 177.
25. G. B. Shul'pin, J. Gradinaru, Y. N. Kozlov, Org. Biomol. Chem. 2003, 1, 3611.
26. S. Velusamy, T. Punniyamurthy, Tetrahedron Lett. 2003, 44, 8955.
27. R. S. da Cruz, J. M. D. E. Silva, U. Arnold, M. S. Sercheli, U. Schuchardt, J. Brazil. Chem. Soc. 2002, 13, 170.
28. S.-H. Murahashi, N. Komiya, Y. Hayashi, T. Kumano, Pure Appl. Chem. 2001, 73, 311.
29. T. Ohta, T. Tachiyama, K. Yoshizawa, T. Yamabe, T. Uchida, T. Kitagawa, Inorg. Chem. 2000, 39, 4358.
30. W. A. Carvalho, M. Wallau, U. Schuchardt, J. Mol. Catal. A: Chem. 1999, 144, 91.
31. U. Schuchardt, R. Pereira, M. Rufo, J. Mol. Catal. A: Chem. 1998, 135, 257.
32. R. Raja, P. Ratnasamy, Catal. Lett. 1997, 48, 1.
33. T. Okuno, S. Ohba, Y. Nishida, Polyhedron 1997, 16, 3765.
34. N. Komiya, T. Naota, Y. Oda, S. I. Murahashi, J. Mol. Catal. A: Chem. 1997, 117, 21.
35. D. H. R. Barton, S. D. Beviere, W. Chavasiri, E. Csuhai, D. Doller, Tetrahedron 1992, 48, 2895.
36. A. M. Kirillov, M. N. Kopylovich, M. V. Kirillova, M. Haukka, M. F. C. G. da Silva, A. J. L. Pombeiro, Angew. Chem. Int. Ed. 2005, 44, 4345.
37. L. A. Kovbasyuk, O. Yu. Vassilyeva, V. N. Kokozay, H. Chun, I. Bernal, J. Reedijk, G. Van Albada, B. W. Skelton, Cryst. Eng. 2001, 4, 201.
38. V. Tudor, V. Kravtsov, M. Julve, F. Lloret, Y. A. Simonov, J. Lipkowski, V. Buculei, M. Andruh, Polyhedron 2001, 20, 3033.
39. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Chem. Soc. Perkin Trans. 2. 1987, S1.
40. J. Pinkas, J. C. Huffman, J. C. Bollinger, W. E. Streib, D. V. Baxter, M. H. Chisholm, K. G. Caulton, Inorg. Chem. 1997, 36, 2930.
41. Y. Topcu, O. Andac, V. T. Yilmaz, W. T. A. Harrison, J. Coord. Chem. 2002, 55, 805.
42. V. Tudor, G. Marin, V. Kravtsov, Yu. A. Simonov, J. Lipkowski, M. Brezeanu, M. Andruh, Inorg. Chim. Acta 2003, 353, 35.
43. V. G. Makhankova, O. Yu. Vassilyeva, V. N. Kokozay, B. W. Skelton, J. Reedijk, G. A. Van Albada, L. Sorace, D. Gatteschi, New J. Chem. 2001, 25, 685.
44. M. N. Kopylovich, A. M. Kirillov, A. K. Baev, A. J. L. Pombeiro, J. Mol. Catal. A: Chem. 2003, 206, 163.
45. P. M. Reis, J. A. L. Silva, J. J. R. F. da Silva, A. J. L. Pombeiro, Chem. Commun. 2000, 1845.
46. P. M. Reis, J. A. L. Silva, J. J. R. F. da Silva, A. J. L. Pombeiro, J. Mol. Catal. A: Chem. 2004, 224, 189.
47. E. S. Rudakov, The Reactions of Alkanes with Oxidants, Metal Complexes, and Radicals in Solutions, Naukova Dumka, Kiev, 1985.
48. G. B. Shul'pin, G. Suss-Fink, J. R. L. Smith, Tetrahedron 1999, 55, 5345.
49. I. I. Moiseev, D. I. Shishkin, A. E. Gekhman, New J. Chem. 1989, 23, 683.
50. P. M. Reis, J. A. L. Silva, A. F. Palavra, J. J. R. F. da Silva, T. Kitamura, Y. Fujiwara, A. J. L. Pombeiro, Angew. Chem. Int. Ed. 2003, 42, 821.
51. G. B. Shul'pin, Y. N. Kozlov, G. V. Nizova, G. Suss-Fink, S. Stanislas, A. Kitaygorodskiy, V. S. Kulikova, J. Chem. Soc. Perkin Trans. 2. 2001, 1351.
52. L. M. Slaughter, J. P. Collman, T. A. Eberspacher, J. I. Brauman, Inorg. Chem. 2004, 43, 5198.
53. R. A. Periana, G. Bhalla, W. J. Tenn, K. J. H. Young, X. Y. Liu, O. Mironov, C. J. Jones, V. R. Ziatdinov, J. Mol. Catal. A: Chem. 2004, 220, 7.
54. C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633.
55. J. D. Druliner, N. Herron, S. P. Jordan, K. Kourtakis, S. L. Lane, L. E. Manzer, B. E. Smart, US Patent 6,284,927, 2001.
56. U. F. Kragten, H. A. C. Baur, US Patent 5,959,153, 1999.
57. A. M. Syroezhko, O. Y. Begak, Rus. J. Appl. Chem. 2004, 77, 1301.
58. W. Buijs, R. Raja, J. M. Thomas, H. Wolters, Catal. Lett. 2003, 91, 253.
59. C. B. Hansen, W. Drenth, Catal. Lett. 1993, 20, 359.
60. B. V. Nonius, Data Collection Software: Collect, Delft, The Netherlands, 1997-2000.
61. Z. Otwinowski, W. Minor, Processing of X-ray Diffraction Data Collected in Oscillation Mode, in: Methods in Enzymology, Vol.276, Macromolecular Crystallography, Part A. (Eds.: C. W. Carter, R. M. Sweet), Academic Press, New York, 1997, pp. 307-326.
62. A. J. M. Duisenberg, L. M. J. Kroon-Batenburg, A. M. M. Schreurs, J. Appl. Cryst. 2003, 36, 220.
63. G. M. Sheldrick, SHELXL-97, Program for Crystal Structure Determination, University of Göttingen, Göttingen, Germany, 1997.
64. G. M. Sheldrick, SHELXTL v. 6.12, Bruker Analytical X-ray Systems, Bruker AXS, Madison, Wisconsin, USA, 2002.
65. G. M. Sheldrick, SADABS - Bruker Nonius scaling and absorption correction, v 2.10, Bruker AXS Inc., Madison, Wisconsin, USA, 2003.
66. L. J. Farrugia, J. Appl. Cryst. 1999, 32, 837.