Molecular mapping of the catalytic cycle of the cobalt-catalyzed hydromethoxycarbonylation of 1,3-butadiene in the presence of pyridine in methanol

Organometallics

Volumn 30, Issue 17, 2011, Pages 4751-4764

  Mika, László T ^a   Tuba, Róbert ^a   Tóth, Imre ^b   Pitter, Stephan ^c   Horváth, István T ^a,d  

^a EÖTVÖS LORÁND UNIVERSITY   (Hungary)

^b DSM RESEARCH   (Netherlands)

^c KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^d CITY UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,3-BUTADIENE; 1 ,4-ADDITION; CARBOCATIONS; CATALYTIC CYCLES; COORDINATED CARBON MONOXIDE; DISPROPORTIONATIONS; IN-SITU IR; IONIC SPECIES; METHANOLYSIS; MOLECULAR MAPPING; PYRIDINIUM; REVERSIBLE REACTION;

BUTADIENE; CARBON DIOXIDE; CARBON MONOXIDE; COBALT; METHANOL;

PYRIDINE;

EID: 80052488178     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200617q     Document Type: Article

References (68)

1. Csihony, S.; Mika, L. T.; Vlád, G.; Barta, K.; Mehnert, C. P.; Horváth, I. T. Collect. Czech. Chem. Commun. 2007, 72, 1094
2. Pusztai, Z.; Vlád, G.; Bodor, A.; Horváth, I. T.; Laas, H. J.; Halpaap, R.; Richter, F. U. Angew. Chem., Int. Ed. Engl. 2006, 45, 107
3. Csihony, S.; Bodor, A; Rohonczy, J.; Horváth, I. T. J. Chem. Soc., Perkin Trans. 1 2002, 2861
4. Csihony, S.; Mehdi, H.; Hommonay, Z.; Vértes, A.; Farkas, Ö.; Horváth, I. T. J. Chem. Soc., Dalton Trans. 2002, 680
5. Csihony, S.; Mehdi, H.; Horváth, I. T. Green Chem. 2001, 3, 307
6. Chen, M. J.; Klingler, J. R.; Rathke, J. W.; Kramarz, K. W. Organometallics 2004, 23, 2701
7. Deglmann, P.; Ember, E.; Hofmann, P.; Pitter, S.; Walter, O. Chem. Eur. J. 2007, 13, 2864
8. Tuba, R.; Mika, L. T.; Bodor, A.; Pusztai, Z.; Tóth, I.; Horváth, I. T. Organometallics 2003, 22, 1582
9. de Rege, P. J. F.; Gladysz, J. A.; Horváth, I. T. Adv. Synth. Catal. 2002, 344, 1059
10. Horváth, I. T.; Anastas, P. Chem. Rev. 2007, 107, 2169
11. Horváth, I. T. Green Chem. 2008, 10, 1024
12. Falbe, J. New Synthesis with Carbon Monoxide; Springer-Verlag: Berlin, 1980.
13. Knifton, J. F. J. Catal. 1979, 60, 27
14. Reppe, W.; Kröper, H. Carbonylierung II Liebigs Ann. Chem. 1953, 582, 38
15. Gresham, W. F.; Brooks, R. E. U.S. Patent 2542767 (DuPont), 1951.
16. Hosaka, S.; Tsuji, J. Tetrahedron Lett. 1964, 12, 605
17. Hosaka, S.; Tsuji, J. Tetrahedron 1971, 27, 3821
18. Tsuji, J.; Mori, Y.; Hara, M. Tetrahedron 1972, 27, 3721
19. Tsuji, J. Acc. Chem. Res. 1973, 6, 8
20. Sielcken, O.; Agterberg, F.; Haasen, N. Eur. Patent 728733 (DSM), 1996.
21. Bertleff, W.; Roeper, M.; Sava, X., Carbonylation. In Ullmann's Encyclopedia of Industrial Chemistry, 7 th ed.; Wiley: New York, 2009.
22. Dahlhoff, G.; Niederer, J. P. M.; Hoelderich, W. E. Catal. Rev. 2001, 43, 381
23. Gresham, W. F.; Brooks, R. E. U.S. Patent 2542767 (DuPont), 1951.
24. Isogai, N.; Okawa, T.; Hosokawa, M.; Watanabe, T.; Wakui, N. U.S. Patent 4350668 (Mitsubishi), 1981.
25. Isogai, N.; Hosokawa, M.; Okawa, T.; Wakui, N.; Watanabe, T.; U.S. Patent 4332966 (Mitsubishi), 1980.
26. Bertleff, W.; Maerkl, R.; Gerhard, K.; Paul, P.; Rudolf, K. Eur. Patent EP0267497 (BASF), 1996.
27. Maerkl, R.; Bertleff, W.; Wilfinger, H. J.; Schuch, G.; Harder, W.; Kuehn, G.; Panitz, P. U.S. Patent 4894474 (BASF), 1990.
28. Rudolf, K.; Schneider, H.-W.; Weiss, F.-J.; Lemann, O. U.S. Patent 4256909 (BASF), 1981.
29. Platz, R.; Rudolf, K.; Schneider, H.-W.; Schwirten, K. U.S. Patent 4550195 (BASF), 1985.
30. Jenck, J. U.S. Patent 4454333 (Rhone/Poluenc), 1984).
31. Drent, E. Eur. Patent 0235864 (Shell), 1987.
32. Drent, E.; Jager, W. W. U.S. Patent. 5350876 (Shell, 1994).
33. Beller, M.; Cornils, B.; Frohning, C. D.; Kohlpainter, C. W. J. Mol. Catal. A 1995, 104, 17
34. Chem. Eng. News. 1987, 65, 14.
35. Bruke, P. M. U.S. Patent 4622423 (DuPont,), 1986.
36. Bruke, P. M. U.S. Patent 4788333 (DuPont), 1988.
37. Bruke, P. M. U.S. Patent 5145995 (DuPont), 1992.
38. Atadan, E. M. U.S. Patent 5218144 (DuPont), 1993.
39. Matsuda, A. Bull. Chem. Soc. Jpn. 1973, 46, 524
40. Hofmann, P.; Kosswig, K.; Schaefer, W. Ind. Eng. Chem. Prod. Res. Dev. 1980, 19, 330
41. Jacob, C.; Heaton, B. T.; Iggo, J. A.; Whyman, R. J. Mol. Catal. A.: Chem. 2003, 204-205, 149
42. Forster, D.; Hersman, A.; Morris, D. E. Catal. Rev. Sci. Eng. 1981, 23, 89
43. Rupilius, W.; Orchin, M. J. Org. Chem. 1971, 36, 3604
44. Imyanitov, N. S.; Bogoradovskaya, N. M.; Semenova, T. A. Kinet. Katal. 1978, 19, 573
45. Imyanitov, N. S. Kinet. Katal. 1999, 40, 71
46. Milstein, D.; Huckaby, J. L. J. Am. Chem. Soc. 1982, 104, 6150
47. Milstein, D. Acc. Chem. Res. 1988, 21, 428-434
48. Reppe, W. Liebigs Ann. Chem. 1952, 682, 116
49. Hieber, W.; Sedlmeyer, J. Chem. Ber. 1954, 87, 25
50. Sternberg, H. W.; Wender, I.; Friedel, R. A.; Orchin, M. J. Am. Chem. Soc. 1953, 75, 2718
51. Orchin, M. Acc. Chem. Res. 1981, 14, 259
52. Schunn, R. A. In Transition Metal Hydrides; Muetterties, E. L., Ed.; Dekker: New York, 1971; p 203.
53. Jonassen, H. B.; Stearns, R. I.; Kenttamaa, J.; Moore, D. W.; Whittaker, A. G. J. Am. Chem. Soc. 1958, 80, 2586
54. Ungváry, F.; Markó, L. J. Organomet. Chem. 1980, 193, 383
55. Heck, R. F.; Breslow, S. D. J. Am. Chem. Soc. 1961, 83, 4023
56. Ungváry, F. Hydroformylation-Homogeneous. In Encyclopedia of Catalysis; Horváth, I. T., Ed. Wiley: Hoboken, NJ, 2003.
57. Ungváry, F.; Markó, L. J. Organomet. Chem. 1981, 219, 397
58. Ungváry, F.; Markó, L. Organometallics 1984, 3, 1466
59. Huo, C-F; Li, Y-W; Beller, M.; Jiao, H. Organometallics 2005, 24, 3634
60. Organic Chemistry, 4 th ed.; Morrison, R. T.; Boyd, R. N., Eds. Allyn and Bacon: Boston, 1983.
61. Beller, M.; Krotz, A.; Baumann, W. Adv. Synth. Catal. 2002, 344, 517
62. Bank, S.; Rowe, C. A. J.; Schriesheim, A.; Naslund, L. A. J. Org. Chem. 1968, 33
63. Damico, R. J. Org. Chem. 1968, 33, 1550
64. Heck, R. F.; Breslow, S. D. J. Am. Chem. Soc. 1961, 83, 1097
65. Huo, C.-F.; Li, Y.-W.; Beller, M.; Jiao, H. Organometallics 2005, 24, 3634
66. Mirbach, M. F. J. Mol. Catal. 1985, 33, 23
67. Mirbach, M. F. J. Mol. Catal. 1985, 32, 59
68. Horváth, I. T.; Millar, J. M. Chem. Rev. 1991, 91, 1339