Mild oxidative functionalization of alkanes and alcohols catalyzed by new mono- and dicopper(II) aminopolyalcoholates

Journal of Molecular Catalysis A: Chemical

Volumn 350, Issue 1-2, 2011, Pages 26-34

  Kirillov, Alexander M ^a   Kirillova, Marina V ^a   Shul'Pina, Lidia S ^b   Figiel, Paweł J ^a   Gruenwald, Katrin R ^a   Guedes Da Silva, M Fátima C ^a,c   Haukka, Matti ^d   Pombeiro, Armando J L ^a   Shul'Pin, Georgiy B ^e  

^a INSTITUTO SUPERIOR TÉCNICO   (Portugal)

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

^c UNIVERSIDADE LUSÓFONA DE HUMANIDADES E TECNOLOGIAS   (Portugal)

^d UNIVERSITY OF EASTERN FINLAND   (Finland)

^e SEMENOV INSTITUTE OF CHEMICAL PHYSICS   (Russian Federation)

Author keywords

C H activation; Carboxylation; Copper complexes; Homogeneous catalysis; N,O ligands; Oxidation

Indexed keywords

ALKYL PEROXIDES; AQUEOUS MEDIUM; C-H ACTIVATION; COPPER COMPLEXES; CYCLOHEXANOL; CYCLOHEXANONES; DICOPPER; DICOPPER COMPLEXES; ETHYLENE DIAMINE; FREE RADICAL MECHANISM; HOMOGENEOUS CATALYSIS; HOMOGENEOUS CATALYST; HYDROCARBOXYLATION; N,O LIGANDS; OXIDATION OF ALCOHOLS; OXIDATION OF CYCLOHEXANE; OXIDATIVE FUNCTIONALIZATION; OXIDATIVE TRANSFORMATIONS; SELECTIVITY PARAMETERS; SELF-ASSEMBLED; SINGLE CRYSTAL X-RAY DIFFRACTION ANALYSIS; TETRAKIS; TOTAL YIELD;

ACTIVATION ANALYSIS; CARBOXYLATION; CARBOXYLIC ACIDS; CATALYSIS; COPPER COMPOUNDS; KETONES; ORGANIC COMPOUNDS; OXIDATION; OXYGENATION; REACTION KINETICS; X RAY DIFFRACTION; X RAY DIFFRACTION ANALYSIS;

PARAFFINS;

EID: 80054934874     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2011.08.028     Document Type: Article

References (70)

1. A.E. Shilov, and G.B. Shul'pin Activation and Catalytic Reactions of Saturated Hydrocarbons in the Presence of Metal Complexes 2000 Kluwer Acad. Publ. Dordrecht
2. G.A. Olah, and Á. Molnár Hydrocarbon Chemistry 2003 Wiley Hoboken, NJ
3. G.B. Shul'pin second ed. M. Beller, C. Bolm, Transition Metals for Organic Synthesis vol. 2 2004 Wiley-VCH Weinheim/New York 215 242
4. G.B. Shul'pin Mini-Rev. Org. Chem. 6 2009 95 104
5. J.A. Labinger, and J.E. Bercaw Nature 417 2002 507 514
6. R.H. Crabtree J. Organomet. Chem. 689 2004 4083 4091
7. A.A. Fokin, and P.R. Schreiner Chem. Rev. 102 2002 1551 1593
8. A. Sen Acc. Chem. Res. 31 1998 550 557
9. A.E. Shilov, and G.B. Shul'pin Chem. Rev. 97 1997 2879 2932
10. Ullmann's Encyclopedia of Industrial Chemistry 6th ed. 2002 Wiley-VCH Weinheim
11. Encyclopedia of Chemical Technology 5th ed. 2004 Kirk-Othmer, Wiley New York
12. H. Wittcoff, B.G. Reuben, and J.S. Plotkin Industrial Organic Chemicals 2nd ed. 2004 Wiley
13. Carboxylic Acids: Carboxylic Acid, Formic Acid, Niacin, Valproic Acid, Essential Fatty Acid, Acetoacetic Acid, Pcaa, Ibuprofen, Lipoic Acid 2010 General Books LLC
14. H.M. Colquhoun, D.J. Thompson, and M.V. Twigg Carbonylation: Direct Synthesis of Carbonyl Compounds 1991 Springer
15. G. Tojo, and M. Fernández Oxidation of Alcohols to Aldehydes and Ketones: A Guide to Current Common Practice 2006 Springer New York
16. Y.Y. Karabach, M.F.C. Guedes da Silva, M.N. Kopylovich, B. Gil-Hernández, J. Sanchiz, A.M. Kirillov, and A.J.L. Pombeiro Inorg. Chem. 49 2010 11096 11105
17. M.V. Kirillova, A.M. Kirillov, M.F.C. Guedes da Silva, and A.J.L. Pombeiro Eur. J. Inorg. Chem. 2008 3423 3427
18. M.V. Kirillova, A.M. Kirillov, P.M. Reis, J.A.L. Silva, J.J.R. Fraústo da Silva, and A.J.L. Pombeiro J. Catal. 248 2007 130 136
19. D.S. Nesterov, V.N. Kokozay, V.V. Dyakonenko, O.V. Shishkin, J. Jezierska, A. Ozarowski, A.M. Kirillov, M.N. Kopylovich, and A.J.L. Pombeiro Chem. Commun. 2006 4605 4607
20. M.N. Kopylovich, A.M. Kirillov, A.K. Baev, and A.J.L. Pombeiro J. Mol. Catal. A: Chem. 206 2003 163 178
21. G.B. Shul'pin, J. Gradinaru, and Y.N. Kozlov Org. Biomol. Chem. 1 2003 3611 3617
22. L.S. Shul'pina, K. Takaki, T.V. Strelkova, and G.B. Shul'pin Petrol. Chem. 48 2008 219 222
23. 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
24. P.J. Figiel, A.M. Kirillov, M.F.C. Guedes da Silva, J. Lasri, and A.J.L. Pombeiro Dalton Trans. 39 2010 9879 9888
25. P.J. Figiel, A.M. Kirillov, Y.Y. Karabach, M.N. Kopylovich, and A.J.L. Pombeiro J. Mol. Catal. A: Chem. 305 2009 178 182
26. 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
27. K.R. Gruenwald, A.M. Kirillov, M. Haukka, J. Sanchiz, and A.J.L. Pombeiro Dalton Trans. 2009 2109 2120
28. Y.Y. Karabach, A.M. Kirillov, M. Haukka, M.N. Kopylovich, and A.J.L. Pombeiro J. Inorg. Biochem. 102 2008 1190 1194
29. M.V. Kirillova, A.M. Kirillov, M.L. Kuznetsov, J.A.L. Silva, J.J.R. Fraústo da Silva, and A.J.L. Pombeiro Chem. Commun. 2009 2353 2355
30. See the Cambridge Structural Database (CSD, version 5.32, Feb. 2011)
31. F.H. Allen Acta Crystallogr. B 58 2002 380 388
32. A.S. de Sousa, and M.A. Fernandes Polyhedron 21 2002 1883 1888
33. O. Orama, M. Orama, and U. Schubert Finn. Chem. Lett. 1 1979 136 139
34. L. Que Jr., and W.B. Tolman Nature 455 2008 333 340
35. E.A. Lewis, and W.B. Tolman Chem. Rev. 104 2004 1047 1076
36. P. Gamez, P.G. Aubel, W.L. Driessen, and J. Reedijk Chem. Soc. Rev. 30 2001 376 385
37. R.L. Lieberman, and A.C. Rosenzweig Nature 434 2005 177 182
38. S.I. Chan, V.C.-C. Wang, J.C.-H. Lai, S.S.-F. Yu, P.P.-Y. Chen, K.H.-C. Chen, C.-L. Chen, and M.K. Chan Angew. Chem. Int. Ed. 46 2007 1992 1994
39. Z. Otwinowski, and W. Minor C.W. Carter, J. Sweet, Methods in Enzymology, Volume 276, Macromolecular Crystallography, Part A 1997 Academic Press New York, USA 307 326
40. G.M. Sheldrick Acta Crystallogr. A 64 2008 112 122
41. L.J. Farrugia J. Appl. Crystallogr. 32 1999 837 838
42. Bruker APEX2 & SAINT 2004 AXS Inc. Madison, WI
43. G.B. Shul'pin J. Mol. Catal. A: Chem. 189 2002 39 66
44. G.B. Shul'pin CR Chimie 6 2003 163 178
45. M.V. Kirillova, A.M. Kirillov, and A.J.L. Pombeiro Adv. Synth. Catal. 351 2009 2936 2948
46. M.V. Kirillova, A.M. Kirillov, and A.J.L. Pombeiro Appl. Catal. A: Gen. 401 2011 106 113
47. M.V. Kirillova, A.M. Kirillov, and A.J.L. Pombeiro Chem. Eur. J. 16 2010 9485 9493
48. A.M. Kirillov, Y.Y. Karabach, M.V. Kirillova, M. Haukka, and A.J.L. Pombeiro Dalton Trans. 40 2011 6378 6381
49. A.M. Kirillov, J.A.S. Coelho, M.V. Kirillova, M.F.C. Guedes da Silva, D.S. Nesterov, K.R. Gruenwald, M. Haukka, and A.J.L. Pombeiro Inorg. Chem. 49 2010 6390 6392
50. A.M. Kirillov, Y.Y. Karabach, M. Haukka, M.F.C. Guedes da Silva, J. Sanchiz, M.N. Kopylovich, and A.J.L. Pombeiro Inorg. Chem. 47 2008 162 175
51. Y.Y. Karabach, A.M. Kirillov, M. Haukka, J. Sanchiz, M.N. Kopylovich, and A.J.L. Pombeiro Cryst. Growth Des. 8 2008 4100 4108
52. K. Nakamoto Infrared and Raman Spectra of Inorganic and Coordination Compounds 5th ed. 1997 Wiley New York
53. A.M. Kirillov, M.N. Kopylovich, M.V. Kirillova, E.Y. Karabach, M. Haukka, M.F.C.G. da Silva, and A.J.L. Pombeiro Adv. Synth. Catal. 348 2006 159 174
54. A.M. Kirillov, M.N. Kopylovich, M.V. Kirillova, M. Haukka, M.F.C.G. da Silva, and A.J.L. Pombeiro Angew. Chem. Int. Ed. 44 2005 4345 4349
55. G.B. Shul'pin, Y.N. Kozlov, L.S. Shul'pina, A.R. Kudinov, and D. Mandelli Inorg. Chem. 48 2009 10480 10482
56. G.B. Shul'pin, Y.N. Kozlov, L.S. Shul'pina, and P.V. Petrovskiy Appl. Organomet. Chem. 24 2010 464 472
57. G.B. Shul'pin, G.V. Nizova, Y.N. Kozlov, L. Gonzalez Cuervo, and G. Süss-Fink Adv. Synth. Catal. 346 2004 317 332
58. 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
59. L.S. Shul'pina, M.V. Kirillova, A.J.L. Pombeiro, and G.B. Shul'pin Tetrahedron 65 2009 2424 2429
60. 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
61. G.B. Shul'pin, M.V. Kirillova, Y.N. Kozlov, L.S. Shul'pina, A.R. Kudinov, and A.J.L. Pombeiro J. Catal. 277 2011 164 172
62. G.B. Shul'pin, M.V. Kirillova, T. Sooknoi, and A.J.L. Pombeiro Catal. Lett. 128 2008 135 141
63. G.B. Shul'pin, G. Süss-Fink, and L.S. Shul'pina J. Mol. Catal. A: Chem. 170 2001 17 34
64. Y.N. Kozlov, G.V. Nizova, and G.B. Shul'pin J. Phys. Org. Chem. 21 2008 119 126
65. For a recent review on regioselectivity, see
66. G.B. Shul'pin Org. Biomol. Chem. 8 2010 4217 4228
67. F. Minisci, A. Citterio, and C. Giordano Acc. Chem. Res. 16 1983 27 32
68. M.V. Kirillova, M.L. Kuznetsov, P.M. Reis, J.A.L. da Silva, J.J.R. Fraústo da Silva, and A.J.L. Pombeiro J. Am. Chem. Soc. 129 2007 10531 10545
69. P.M. Reis, J.A.L. Silva, A.F. Palavra, J.J.R. Fraústo da Silva, and A.J.L. Pombeiro J. Catal. 235 2005 333 340
70. G.A. Olah, G.K. Surya Prakash, Á. Molnár, and J. Sommer Superacid Chemistry 2nd ed. 2009 Wiley New York