Catalytic olefin epoxidation with a fluorinated organomolybdenum complex

Journal of Molecular Catalysis A: Chemical

Volumn 363-364, Issue , 2012, Pages 237-244

  Hauser, Simone A ^a   Cokoja, Mirza ^a   Drees, Markus ^a   Kühn, Fritz E ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Fluorinated solvents; Homogeneous catalysis; Ionic liquids; Olefin epoxidation; Organomolybdenum complexes

Indexed keywords

ANSA-COMPOUNDS; CARBONYL COMPLEXES; CATALYST RECYCLING; CATALYTIC EPOXIDATION; CYCLOOCTENE; FLUORINATED SOLVENTS; HEXAFLUOROISOPROPANOL; HIGH STABILITY; HOMOGENEOUS CATALYSIS; NMR STUDIES; OLEFIN EPOXIDATION; ORGANOMOLYBDENUM COMPLEXES; PRECATALYSTS; ROOM TEMPERATURE; TERT-BUTYLHYDROPEROXIDE; TURNOVER FREQUENCY;

CATALYSTS; EPOXIDATION; IONIC LIQUIDS; OLEFINS; REACTION KINETICS;

MOLYBDENUM COMPOUNDS;

EID: 84866035326     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2012.06.015     Document Type: Article

References (66)

1. F.E. Kühn, A.M. Santos, and W.A. Herrmann Dalton Trans. 2005 2483 2491
2. F.E. Kühn, A.M. Santos, and M. Abrantes Chem. Rev. 106 2006 2455 2475
3. N. Grover, and F.E. Kühn Curr. Org. Chem. 16 2012 16 32
4. M.B. Trost, and R.G. Bergman Organometallics 10 1991 1172 1178
5. I.S. Gonçalves, A.M. Santos, C.C. Romão, A.D. Lopes, J.E. Rodríguez-Borges, M. Pillinger, P. Ferreira, J. Rocha, and F.E. Kühn J. Organomet. Chem. 636 2001 1 10
6. R. Poli Chem. Eur. J. 10 2004 332 341
7. F.E. Kühn, J. Zhao, M. Abrantes, W. Sun, C.A.M. Afonso, L.C. Branco, I.S. Gonçalves, M. Pillinger, and C.C. Romão Tetrahedron Lett. 46 2005 47 52
8. A.A. Valente, J.D. Seixas, I.S. Gonçalves, M. Abrantes, M. Pillinger, and C.C. Romão Catal. Lett. 101 2005 127 130
9. A.M. Martins, C.C. Romão, M. Abrantes, M.C. Azevedo, J. Cui, A.R. Dias, M.T. Duarte, M.A. Lemos, T. Lourenço, and R. Poli Organometallics 24 2005 2582 2589
10. M. Abrantes, F.A. Almeida Paz, A.A. Valente, C.C.L. Pereira, S. Gago, A.E. Rodrigues, J. Klinowski, M. Pillinger, and I.S. Gonçalves J. Organomet. Chem. 694 2009 1826 1833
11. P. Neves, C.C.L. Pereira, F.A. Almeida Paz, S. Gago, M. Pillinger, C.M. Silva, A.A. Valente, C.C. Romão, and I.S. Gonçalves J. Organomet. Chem. 695 2010 2311 2319
12. C. Dinoi, M. Ciclosi, E. Manoury, L. Maron, L. Perrin, and R. Poli Chem. Eur. J. 16 2010 9572 9584
13. M. Abrantes, P. Neves, M.M. Antunes, S. Gago, F.A. Almeida Paz, A.E. Rodrigues, M. Pillinger, I.S. Gonçalves, C.M. Silva, and A.A. Valente J. Mol. Catal. A: Chem. 320 2010 19 26
14. P.M. Reis, C.A. Gamelas, J.A. Brito, N. Saffon, M. Gómez, and B. Royo Eur. J. Inorg. Chem. 2011 666 673
15. M. Abrantes, S.M. Bruno, C. Tome, M. Pillinger, I.S. Gonçalves, and A.A. Valente Catal. Commun. 15 2011 64 67
16. J. Pisk, D. Agustin, V. Vrdoljak, and R. Poli Adv. Synth. Catal. 353 2011 2910 2914
17. F.E. Kühn, A.M. Santos, A.D. Lopes, I.S. Gonçalves, E. Herdtweck, and C.C. Romão J. Mol. Catal. A: Chem. 164 2000 25 38
18. F.E. Kühn, A.D. Lopes, A.M. Santos, E. Herdtweck, J.J. Haider, C.C. Romão, and A.G. Santos J. Mol. Catal. A: Chem. 151 2000 147 160
19. F.E. Kühn, M. Groarke, E. Bencze, E. Herdtweck, A. Prazeres, A.M. Santos, M.J. Calhorda, C.C. Romão, I.S. Gonçalves, A.D. Lopes, and M. Pillinger Chem. Eur. J. 8 2002 2370 2383
20. A.A. Valente, Z. Petrovski, L.C. Branco, C.A.M. Afonso, M. Pillinger, A.D. Lopes, C.C. Romão, C.D. Nunes, and I.S. Gonçalves J. Mol. Catal. A: Chem. 218 2004 5 11
21. A. Al-Ajlouni, A.A. Valente, C.D. Nunes, M. Pillinger, A.M. Santos, J. Zhao, C.C. Romão, I.S. Gonçalves, and F.E. Kühn Eur. J. Inorg. Chem. 2004 1716 1723
22. A. Günyar, and F.E. Kühn J. Mol. Catal. A: Chem. 319 2010 108 113
23. M. Abrantes, A.M. Santos, J. Mink, F.E. Kühn, and C.C. Romão Organometallics 22 2003 2112 2118
24. J. Zhao, A.M. Santos, E. Herdtweck, and F.E. Kühn J. Mol. Catal. A: Chem. 222 2004 265 271
25. C. Freund, M. Abrantes, and F.E. Kühn J. Organomet. Chem. 691 2006 3718 3729
26. A.M. Al-Ajlouni, D. Veljanovski, A. Capapé, J. Zhao, E. Herdtweck, M.J. Calhorda, and F.E. Kühn Organometallics 28 2009 639 645
27. A.A. Valente, J. Moreira, A.D. Lopes, M. Pillinger, C.D. Nunes, C.C. Romão, F.E. Kühn, and I.S. Gonçalves New J. Chem. 28 2004 308 313
28. S.M. Bruno, C.C.L. Pereira, M.S. Balula, M. Nolasco, A.A. Valente, A. Hazell, M. Pillinger, P. Ribeiro-Claro, and I.S. Gonçalves J. Mol. Catal. A: Chem. 261 2007 79 87
29. A.C. Coelho, M. Nolasco, S.S. Balula, M.M. Antunes, C.C.L. Pereira, F.A.A. Paz, A.A. Valente, M. Pillinger, P. Ribeiro-Claro, J. Klinowski, and I.S. Gonçalves Inorg. Chem. 50 2011 525 538
30. F. Madeira, S. Barroso, S. Namorado, P.M. Reis, B. Royo, and A.M. Martins Inorg. Chim. Acta 383 2012 152 156
31. S.S. Balula, S.M. Bruno, A.C. Gomes, A.A. Valente, M. Pillinger, I.S. Gonçalves, D.J. Macquarrie, and J.H. Clark Inorg. Chim. Acta 387 2012 234 239
32. A. Capapé, A. Raith, and F.E. Kühn Adv. Synth. Catal. 351 2009 66 70
33. A. Capapé, A. Raith, E. Herdtweck, M. Cokoja, and F.E. Kühn Adv. Synth. Catal. 352 2010 547 556
34. D. Betz, A. Raith, M. Cokoja, and F.E. Kühn ChemSusChem 3 2010 559 562
35. R.B. King, and M.B. Bisnette J. Organomet. Chem. 2 1964 15 37
36. C.C. Romão, F.E. Kühn, and W.A. Herrmann Chem. Rev. 97 1997 3197 3246
37. F.E. Kühn, A. Scherbaum, and W.A. Herrmann J. Organomet. Chem. 689 2004 4149 4164
38. R. Wiest, T. Leininger, G.H. Jeung, and M. Bénard J. Phys. Chem. 96 1992 10800 10804
39. J. Iskra, D. Bonnet-Delpon, and J.-P. Bégué Tetrahedron Lett. 43 2002 1001 1003
40. M.C.A. van Vielt, I.W.C.E. Arends, and R.A. Sheldon Chem. Commun. 1999 821 822
41. A. Berkessel, and J.A. Adrio Adv. Synth. Catal. 346 2004 275 280
42. M.C.A. van Vielt, I.W.C.E. Arends, and R.A. Sheldon Synlett 2 2001 248 250
43. M.C.A. van Vielt, I.W.C.E. Arends, and R.A. Sheldon Synlett 8 2001 1305 1307
44. J.-P. Bégué, D. Bonnet-Delpon, and B. Crousse Synlett 1 2004 18 29
45. T. Welton Chem. Rev. 99 1999 2071 2083
46. B. Kirchner Topics in Current Chemistry vol. 290 2010 Springer Berlin, Heidelberg
47. P. Ferreira, I.S. Gonçalves, F.E. Kühn, A.D. Lopes, M.A. Martins, A. Pina, J. Rocha, C.C. Romão, A.M. Santos, T.M. Santos, and A.A. Valente Eur. J. Inorg. Chem. 2000 2263 2270
48. A. Sakthivel, J. Zhao, M. Hanzlik, A.S.T. Chiang, W.A. Herrmann, and F.E. Kühn Adv. Synth. Catal. 347 2005 473 483
49. C.D. Nunes, M. Pillinger, A.A. Valente, I.S. Gonçalves, J. Rocha, P. Ferreira, and F.E. Kühn Eur. J. Inorg. Chem. 5 2002 1100 1107
50. K.R. Jain, and F.E. Kühn J. Organomet. Chem. 692 2007 5532 5540
51. D. Betz, W.A. Herrmann, and F.E. Kühn J. Organomet. Chem. 694 2009 3320 3324
52. R.B. King Organometallic Syntheses vol. 1 1965 Academic Press New York pp. 145-147
53. M.J. Frisch Gaussian 03 Rev. E.01 2004 Gaussian Inc. Wallingford, CT
54. S.H. Vosko, L. Wilk, and M. Nusair Can. J. Phys. 58 1980 1200 1211
55. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785 789
56. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
57. W.J. Hehre, R. Ditchfield, and J.A. Pople J. Chem. Phys. 56 1972 2257 2261
58. D. Andrae, U. Haeussermann, M. Dolg, H. Stoll, and H. Preuss Theor. Chim. Acta 77 1990 123 141
59. R. Ditchfield Mol. Phys. 27 1974 789 807
60. K. Wolinski, J.F. Hilton, and P. Pulay J. Am. Chem. Soc. 112 1990 8251 8260
61. J.R. Cheeseman, G.W. Trucks, T.A. Keith, and M.J. Frisch J. Chem. Phys. 104 1996 5497 5509
62. R. Krishnan, J.S. Binkley, R. Seeger, and J.A. Pople J. Chem. Phys. 72 1980 650 654
63. A. Berkessel, J.A. Adrio, D. Hüttenhain, and J.M. Neudörfl J. Am. Chem. Soc. 128 2006 8421 8426
64. A. Berkessel, and J.A. Adrio J. Am. Chem. Soc. 128 2006 13412 13420
65. A. Comas-Vives, A. Lledós, and R. Poli Chem. Eur. J. 16 2010 2147 2158
66. P.J. Costa, M.J. Calhorda, and F.E. Kühn Organometallics 29 2010 303 311