Decamethylosmocene-catalyzed efficient oxidation of saturated and aromatic hydrocarbons and alcohols with hydrogen peroxide in the presence of pyridine

Journal of Catalysis

Volumn 277, Issue 2, 2011, Pages 164-172

  Shul'Pin, Georgiy B ^a   Kirillova, Marina V ^b   Kozlov, Yuriy N ^a   Shul'Pina, Lidia S ^c   Kudinov, Alexander R ^c   Pombeiro, Armando J L ^b  

^a SEMENOV INSTITUTE OF CHEMICAL PHYSICS   (Russian Federation)

^b INSTITUTO SUPERIOR TÉCNICO   (Portugal)

^c A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

Alcohols; Alkanes; Benzene; C H functionalization; Homogeneous catalysis; Hydrogen peroxide; Metallocenes; Osmium complexes

Indexed keywords

ALKANES; C-H FUNCTIONALIZATION; HOMOGENEOUS CATALYSIS; METALLOCENES; OSMIUM COMPLEXES;

ACETONITRILE; ALDEHYDES; AROMATIC HYDROCARBONS; BENZENE; BENZENE REFINING; CATALYSIS; CYCLOHEXANE; ETHANE; ETHANOL; HYDROGEN; HYDROGEN PEROXIDE; KETONES; ORGANOMETALLICS; OSMIUM; PHENOLS; PYRIDINE; REACTION KINETICS; STYRENE;

OXIDATION;

EID: 78650804977     PISSN: 00219517     EISSN: 10902694     Source Type: Journal    
DOI: 10.1016/j.jcat.2010.11.002     Document Type: Article

References (66)

1. M. Beller, C. Bolm, Transition Metals for Organic Synthesis second ed. 2004 Wiley-VCH Weinheim, Germany
2. G. Tojo, and M. Fernandez Oxidation of Alcohols to Aldehydes and Ketones 2006 Springer Science, Business Media, Inc. New York
3. T. Seki, and A. Baiker Chem. Rev. 109 2009 2409 2454
4. Z. Ye, Z. Fu, S. Zhong, F. Xie, X. Zhou, F. Liu, and D. Yin J. Catal. 261 2009 110 115
5. P.J. Figiel, and J.M. Sobczak J. Catal. 263 2009 167 172
6. L.S. Shul'pina, K. Takaki, T.V. Strelkova, and G.B. Shul'pin Petrol. Chem. 48 2008 219 222
7. N.K. Renuka, and J. Mol Catal. A: Chem. 316 2010 126 130
8. S.T. Oyama, Mechanisms in Homogeneous and Heterogeneous Epoxidation 2008 Elsevier
9. M. Vasconcellos-Dias, C.D. Nunes, P.D. Vaz, P. Ferreira, P. Brandão, V. Félix, and M.J. Calhorda J. Catal. 256 2008 301 311
10. A. Corma, I. Domínguez, A. Doménech, V. Fornés, C.J. Gómez-García, T. Ródenas, and M.J. Sabater J. Catal. 265 2009 238 244
11. G.A.E. Oxford, M.C. Curet-Arana, D. Majumder, R.W. Gurney, M.L. Merlau, S.T. Nguyen, R.Q. Snurr, and L.J. Broadbelt J. Catal. 266 2009 145 155
12. D. Jiang, T. Mallat, D.M. Meier, A. Urakawa, and A. Baiker J. Catal. 270 2010 26 33
13. J.M. Escola, J.A. Botas, C. Vargas, and M. Bravo J. Catal. 270 2010 34 39
14. M.G. Buonomenna, G. Golemme, M.P. De Santo, and E. Drioli Org. Proc. Res. Develop. 14 2010 252 258
15. T.R. Amarante, P. Neves, A.C. Coelho, S. Gago, A.A. Valente, F.A.A. Paz, M. Pillinger, and I.S. Gonalves Organometallics 29 2010 883 892
16. A.E. Shilov, and G.B. Shul'pin Chem. Rev. 97 1997 2879 2932
17. A.E. Shilov, and G.B. Shul'pin Activation and Catalytic Reactions of Saturated Hydrocarbons in the Presence of Metal Complexes 2000 Dordrecht Kluwer Academic Publishers
18. G.B. Shul'pin Mini-Rev. Org. Chem. 6 2009 95 104
19. G.B. Shul'pin Org. Biomol. Chem. 8 2010 4217 4228
20. G.S. Nunes, A.D.P. Alexiou, and H.E. Toma J. Catal. 260 2008 188 192
21. G.S. Machado, G.G.C. Arizaga, F. Wypych, and S. Nakagaki J. Catal. 274 2010 130 141
22. U. Schuchardt, D. Mandelli, and G.B. Shul'pin Tetrahedron Lett. 37 1996 6487 6490
23. G.B. Shul'pin, D.V. Muratov, L.S. Shul'pina, A.R. Kudinov, T.V. Strelkova, and P.V. Petrovskiy Appl. Organometal. Chem. 22 2008 684 688
24. R. Saladino, V. Nery, A. Farina, C. Crestini, L. Nencioni, and A.T. Palamara Adv. Synth. Catal. 350 2008 321 331
25. M.L. Kuznetsov, and A.J.L. Pombeiro Inorg. Chem. 48 2009 307 318
26. E.A. Karlsson, and T. Privalov Chem. Eur. J. 15 2009 1862 1869
27. P.F. Oblad, J.E. Bercaw, N. Hazari, and J.A. Labinger Organometallics 29 2010 789 794
28. A. Dehestani, A. Wu, R. Hayoun, W. Kaminsky, and J.M. Mayer Inorg. Chim. Acta 362 2009 4534 4538
29. D.H. Ess J. Org. Chem. 74 2009 1498 1508
30. D. Veghini, L.S. Shul'pina, T.V. Strelkova, and G.B. Shul'pin Petrol. Chem. 46 2006 167 170
31. L.S. Shul'pina, D. Veghini, A.R. Kudinov, and G.B. Shul'pin React. Kinet. Catal. Lett. 88 2006 157 164
32. G.B. Shul'pin, Y.N. Kozlov, L.S. Shul'pina, and P.V. Petrovskiy Appl. Organometal. Chem. 24 2010 464 472
33. G.B. Shul'pin, G. Süss-Fink, and L.S. Shul'pina Chem. Commun. 2000 1131 1132
34. G.B. Shul'pin, and G. Süss-Fink Petrol. Chem. 42 2002 233 237
35. T. Osako, E.J. Watson, A. Dehestani, B.C. Bales, and J.M. Mayer Angew. Chem. Int. Ed. 45 2006 7433 7436
36. G.B. Shul'pin, A.R. Kudinov, L.S. Shul'pina, and E.A. Petrovskaya J. Organometal. Chem. 691 2006 837 845
37. L.S. Shul'pina, A.R. Kudinov, E.A. Petrovskaya, T.V. Strelkova, and G.B. Shul'pin Petrol. Chem. 46 2006 164 166
38. S. Ogawa, K. Hosoi, T. Iida, Y. Wakatsuki, M. Makino, Y. Fujimoto, and A.F. Hofmann Eur. J. Org. Chem. 10 2007 3555 3563
39. Q. Yuan, W. Deng, Q. Zhang, and Y. Wang Adv. Synth. Catal. 349 2007 1199 1209
40. S.-M. Yiu, W.-L. Man, and T.-C. Lau J. Am. Chem. Soc. 130 2008 10821 10827
41. G.B. Shul'pin, Y.N. Kozlov, L.S. Shul'pina, A.R. Kudinov, and D. Mandelli Inorg. Chem. 48 2009 10480 10482
42. S. Ogawa, Y. Wakatsuki, M. Makino, Y. Fujimoto, K. Yasukawa, T. Kikuchi, M. Ukiya, T. Akihisa, and T. Iida Chem. Phys. Lipids 163 2010 165 171
43. G.B. Shul'pin, and J. Mol Catal. A: Chem. 189 2002 39 66
44. G.B. Shul'pin Comptes Rendus Chimie 6 2003 163 178
45. G.B. Shul'pin, G.V. Nizova, Y.N. Kozlov, L. Gonzalez Cuervo, and G. Süss-Fink Adv. Synth. Catal. 346 2004 317 332
46. M.V. Kirillova, M.L. Kuznetsov, V.B. Romakh, L.S. Shul'pina, J.J.R. Fraústo da Silva, A.J.L. Pombeiro, and G.B. Shul'pin J. Catal. 267 2009 140 157
47. L.S. Shul'pina, M.V. Kirillova, A.J.L. Pombeiro, and G.B. Shul'pin Tetrahedron 65 2009 2424 2429
48. G.B. Shul'pin J. Chem. Res. 2002 351 353
49. D. Mandelli, K.C. Chiacchio, Y.N. Kozlov, and G.B. Shul'pin Tetrahedron Lett. 49 2008 6693 6697
50. A.J. Bonon, D. Mandelli, O.A. Kholdeeva, M.V. Barmatova, Y.N. Kozlov, and G.B. Shul'pin Appl. Catal. A: Gen. 365 2009 96 104
51. G.B. Shul'pin, M.V. Kirillova, T. Sooknoi, and A.J.L. Pombeiro Catal. Lett. 128 2008 135 141
52. G.V. Nizova, B. Krebs, G. Süss-Fink, S. Schindler, L. Westerheide, L. Gonzalez Cuervo, and G.B. Shul'pin Tetrahedron 58 2002 9231 9237
53. G.B. Shul'pin, G. Süss-Fink, and A.E. Shilov Tetrahedron Lett. 42 2001 7253 7256
54. G.B. Shul'pin, M.G. Matthes, V.B. Romakh, M.I.F. Barbosa, J.L.T. Aoyagi, and D. Mandelli Tetrahedron 64 2008 2143 2152
55. G.B. Shul'pin, Y.N. Kozlov, S.N. Kholuiskaya, M.I. Plieva, and J. Mol Catal. A: Chem. 299 2009 77 87
56. Y.N. Kozlov, G.V. Nizova, and G.B. Shul'pin J. Phys. Org. Chem. 21 2008 119 126
57. G.B. Shul'pin, J. Gradinaru, and Y.N. Kozlov Org. Biomol. Chem. 1 2003 3611 3617
58. G.B. Shul'pin, T. Sooknoi, V.B. Romakh, G. Süss-Fink, and L.S. Shul'pina Tetrahedron Lett. 47 2006 3071 3075
59. M.V. Kirillova, Y.N. Kozlov, L.S. Shul'pina, O.Y. Lyakin, A.M. Kirillov, E.P. Talsi, A.J.L. Pombeiro, and G.B. Shul'pin J. Catal. 268 2009 26 38
60. M.V. Kirillova, A.M. Kirillov, D. Mandelli, W.A. Carvalho, A.J.L. Pombeiro, and G.B. Shul'pin J. Catal. 272 2010 9 17
61. Y.N. Kozlov, G.V. Nizova, G.B. Shul'pin, and J. Mol Catal. A: Chem. 227 2005 247 253
62. G. Süss-Fink, G.V. Nizova, S. Stanislas, G.B. Shul'pin, and J. Mol Catal. A: Chem. 130 1998 163 170
63. P. Neta, R.E. Huie, A.B. Ross, and J. Phys Chem. Ref. Data 17 1988 1027 1284
64. M.H.C. de la Cruz, Y.N. Kozlov, E.R. Lachter, and G.B. Shul'pin New J. Chem. 27 2003 634 638
65. G.B. Shul'pin, Y. Ishii, S. Sakaguchi, and T. Iwahama Russ. Chem. Bull. 48 1999 887 890
66. D.C. Liles, A. Shaver, E. Singleton, and M.B. Wiege J. Organometal. Chem. 288 1985 C33 C36