The mechanism of the hydroalkoxycarbonylation of ethene and alkene-CO copolymerization catalyzed by PdII-diphosphine cations

Chemistry - A European Journal

Volumn 12, Issue 16, 2006, Pages 4417-4430

  Liu, Jianke ^a   Heaton, Brian T ^a   Iggo, Jonathan A ^a   Whyman, Robin ^a   Bickley, Jamie F ^a   Steiner, Alexander ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

Carbonylation; Copolymerization; NMR spectroscopy; Palladium; Reaction mechanisms

Indexed keywords

CARBONYLATION; CATALYSIS; COBALT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PALLADIUM COMPOUNDS; POLYMERIZATION; REACTION KINETICS;

ALKENE-CO COPOLYMERIZATION; CARBOALKOXY CYCLES; HYDROALKOXYCARBONYLATION; METHANOLYSIS;

OLEFINS;

EID: 33744800520     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200501398     Document Type: Article

References (78)

1. E. Drent, P. H. M. Budzelaar, Chem. Rev. 1996, 96, 663-681.
2. A. Sen in Catalytic Synthesis of Alkene-Carbon Monoxide Copolymers and Cooligomers, Vol. 27 (Ed.: A. Sen), Kluwer, Dordrecht, 2003.
3. a) "Special Report on the Industry's campaign for a better image": B. Wassener. FT Chemicals, Wed., September 8, 2004, p. 3;
4. b) Hydrocarbon Process. 2003, 82, 25;
5. c) Plast. Rubber Wkly., 1 July, 2005.
6. E. Drent, J. A. M. Vanbroekhoven, M. J. Doyle, J. Organomet. Chem. 1991, 477, 235-251.
7. W. P. Mul, E. Drent, P. J. Jansens, A. H. Kramer, M. H. W. Sonnemans, J Am. Chem. Soc. 2001, 123, 5350-5351.
8. Z. Freixa, P. van Leeuwen, Dalton Trans. 2003, 1890-1901.
9. I. del Rio, C. Claver, P. van Leeuwen, Eur. J. Inorg. Chem. 2001, 2719-2738.
10. A. Seayad, A. A. Kelkar, L. Toniolo, R. V. Chaudhari, J. Mol. Catal. A 2000, 151, 47-59.
11. A. Vavasori, L. Toniolo, G. Cavinato, F. Vistentin, J. Mol. Catal. A 2003, 204, 295-303.
12. G. Cavinato, A. Vavasori, L. Toniolo, F. Benetollo, Inorg. Chim. Acta 2003, 343, 183-188.
13. A. Seayad, S. Jayasree, K. Damodaran, L. Toniolo, R. V. Chaudhari, J. Organomet. Chem. 2000, 601, 100-107.
14. G. Kiss, Chem. Rev. 2001, 101, 3435-3456.
15. G. Cavinato, L. Toniolo, J. Organomet. Chem. 1990, 398, 187-195.
16. P. van Leeuwen, M. A. Zuideveld, B. H. G. Swennenhuis, Z. Freixa, P. C. J. Kamer, K. Goubitz, J. Fraanje, M. Lutz, A. L. Spek, J. Am. Chem. Soc. 2003, 125, 5523-5539.
17. C. Bianchini, A. Meli, Coord. Chem. Rev. 2002, 225, 35-66.
18. C. Bianchini, A. Meli, W. Oberhauser, Dalton Trans. 2003, 2627-2635.
19. R. A. M. Robertson, D. J. Cole-Hamilton, Coord. Chem. Rev. 2002, 225, 67-90.
20. I. del Rio, C. Claver, P. W. M. N. van Leeuwen, Eur. J. Inorg. Chem. 2001, 2719-2738.
21. G. Consiglio, Chimia 2001, 55, 809-813.
22. D. Milstein, Acc. Chem. Res. 1988, 21, 428-434.
23. S. Otsuka, A. Nakamura, T. Yoshida, M. Naruto, K. Ataka, J. Am. Chem. Soc. 1973, 95, 3180-3188.
24. G. Dekker, C. J. Elsevier, K. Vrieze, P. Vanleeuwen, C. F. Roobeek, J. Organomet. Chem. 1992, 430, 357-372.
25. J. K. Liu, B. T. Heaton, J. A. Iggo, R. Whyman, Angew. Chem. 2004, 116, 92-96;
26. Angew. Chem. Int. Ed. 2004, 43, 90-94.
27. J. K. Liu, B. T. Heaton, J. A. Iggo, R. Whyman, Chem. Commun. 2004, 1326-1327.
28. W. Clegg, G. R. Eastham, M. R. J. Elsegood, B. T. Heaton, J. A. Iggo, R. P. Tooze, R. Whyman, S. Zacchini, J. Chem. Soc. Dalton Trans. 2002, 3300-3308.
29. G. R. Eastham, B. T. Heaton, J. A. Iggo, R. P. Tooze, R. Whyman, S. Zacchini, Chem. Commun. 2000, 609-610.
30. J. A. Iggo, Y. Kawashima, J. Liu, T. Hiyama, K. Nozaki. Organometallics 2003, 22, 5418-5422.
31. C. S. Shultz, J. Ledford, J. M. DeSimone, M. Brookhart, J. Am. Chem. Soc. 2000, 122, 6351-6356.
32. J. Ledford, C. S. Shultz, D. P. Gates, P. S. White, J. M. DeSimone, M. Brookhart, Organometallics 2001, 20, 5266-5276.
33. K. Nozaki, Y. Kawashima, K. Nakamoto, T. Hiyama, Polym. J. 1999, 31, 1057-1060.
34. 3(TFA)] as 1-TFA.
35. 2J(P,P) with those of other complexes 1-L, strongly suggest a monomeric, rather than a bridged structure.
36. W. P. Mul, H. Oosterbeek, G. A. Beitel, G. J. Kramer, E. Drent, Angew. Chem. 2000, 112, 1919-1922;
37. Angew. Chem. Int. Ed. 2000, 39, 1848-1851.
38. C. Bianchini, H. M. Lee, A. Meli, W. Oberhauser, M. Peruzzini, F. Vizza, Organometallics 2002, 21, 16-33.
39. a) I. Toth, C. J. Elsevier, J. Am. Chem. Soc. 1993, 115, 10388-10389;
40. b) I. Toth, C. J. Elsevier, J. Chem. Soc. Chem. Commun. 1993, 529531.
41. R. I. Pugh, E. Drent, Adv. Synth. Catal. 2002, 344, 837-840.
42. 13CO.
43. K. Nozaki, H. Komaki, Y. Kawashima, T. Hiyama, T. Matsubara, J. Am. Chem. Soc. 2001, 123, 534-544.
44. M. J. Green, G. J. P. Britovsek, K. J. Cavell, F. Gerhards, B. F. Yates, K. Frankcombe, B. W. Skelton, A. H. White, J. Chem. Soc. Dalton Trans. 1998, 1137-1144.
45. F. C. Rix, M. Brookhart, P. S. White, J. Am. Chem. Soc. 1996, 118, 4746-4764.
46. P. Braunstein, C. Frison, X. Morise, Angew. Chem. 2000, 112, 29892992;
47. Angew. Chem. Int. Ed. 2000, 39, 2867-2870.
48. K. Nozaki, N. Sato, Y. Tonomura, M. Yasutomi, H. Takaya, T. Hiyama, T. Matsubara, N. Koga, J. Am. Chem. Soc. 1997, 119, 12779-12795.
49. R. I. Pugh, E. Drent in Catalytic Synthesis of Alkene-Carbon Monoxide Copolymers and Cooligomers, Vol. 27 (Ed.; A. Sen), Kluwer, Dordrecht, 2003, Chapter 2.
50. C. Bianchini, A. Meli, W. Oberhauser, P. van Leeuwen, M. A. Zuideveld, Z. Freixa, P. C. J. Kamer, A. L. Spek, O. V. Gusev, A. M. Kal'sin, Organometallics 2003, 22, 2409-2421.
51. G. Cavinato, L. Toniolo, A. Vavasori, J. Mol. Catal. A 2004, 219, 233-240.
52. R. Bertani, G. Cavinato, L. Toniolo, G. Vasapollo, J. Mol. Catal. 1993, 84, 165-176.
53. A. Seayad, S. Jayasree, K. Damodaran, L. Toniolo, R. V. Chaudhari, J. Organomet. Chem. 2000, 601, 100-107.
54. W. R. Moser, A. W. Wang, N. K. Kildahl, J. Am. Chem. Soc. 1988, 110, 2816-2820.
55. W. Keim, J. Becker, A. M. Trzeciak, J. Organomet. Chem. 1989, 372, 447-451.
56. G. D. Smith, B. E. Hanson, J. S. Merola, F. J. Waller, Organometallics 1993, 12, 568-570.
57. A. Dervisi, P.G. Edwards, P.D. Newman, R. P. Tooze, S. J. Coles, M. B. Hursthouse, J. Chem. Soc. Dalton Trans. 1999, 1113-1120.
58. A. Sacco, G. Vasapollo, C. F. Nobile, A. Piergiovanni, M. A. Pellinghelli, M. Lanfranchi, J. Organomet. Chem. 1988, 356, 397-409.
59. J. E. Byrd, J. Halpern, J. Am. Chem. Soc. 1971, 93, 1634-1636.
60. H. E. Bryndza. Organometallics 1985, 4, 1686-1687.
61. H. C. Clark, R. J. Puddephatt, Inorg. Chem. 1970, 9, 2670-2675.
62. 31P NMR spectroscopic data, presumed to be formed by an insertion pathway. No evidence for any of the proposed intermediates was reported.
63. S. A. Macgregor. G. W. Neave, Organometallics 2003, 22, 4547-4556.
64. D. L. Thorn, R. Hoffmann. J. Am. Chem. Soc. 1978, 100, 2079-2090.
65. E. G. Lundquist, K. Folting, W. E. Streib, J. C. Huffman, O. Eisenstein, K. G. Caulton, J. Am. Chem. Soc. 1990, 112, 855-863.
66. S. Mecking, L. K. Johnson, L. Wang, M. Brookhart, J. Am. Chem. Soc. 1998, 120, 888-899.
67. M. A. Zuideveld, P. C. J. Kamer, P. W. M. N. van Leeuwen, P. A. A. Klusener, H. A. Stil, C. F. Roobeek, J. Am. Chem. Soc. 1998, 120, 7977-7978.
68. C. Bianchini, A. Mcli, W. Oberhauser, Dalton Trans. 2003, 2627-2635.
69. C. Bianchini, A. Meli, W. Oberhauser, P. van Leeuwen, M. A. Zuideveld, Z. Freixa, P. C. J. Kamer, A. L. Spek, O. V. Gusev, A. M. Kal'sin, Organometallics 2003, 22, 2409-2421.
70. 31P NMR spectrum of which shows a singlet at δ= 21.1 ppm; and 3) bridged complexes seem to be the exception rather than the rule in this chemistry.
71. 3)]OTs is complicated by the presence of an intramolecular Fe-Pd bond, which reasonably accounts for the observed reactivity of that system.
72. Carbon monoxide was added to suppress the migratory deinsertion back reaction.
73. J. G. Knight, S. Doherty, A. Harriman, E. G. Robins, M. Betham, G. R. Eastham, R. P. Tooze, M. R. J. Elsegood, P. Champkin, W. Clegg, Organometallics 2000, 19, 4957-4967.
74. C. Pisano, G. Consiglio, A. Sironi, M. Moret, J. Chem. Soc. Chem. Commun. 1991, 421-423.
75. A. Fujii, E. Hagiwara, M. Sodeoka, J. Am. Chem. Soc. 1999, 121, 5450-5458.
76. G. Pieri, M. Pasquali, P. Leoni, U. Englert, J. Organomet. Chem. 1995, 491, 27-30.
77. 13CO, some 8 is formed. However, the quality of the NMR spectra after such a long sequence of reactions is poor.
78. H. E. Gottlieb, V. Kotlyar, A. Nudelman, J. Org. Chem. 1997, 62, 7512-7515.