Palladium-catalyzed alternating copolymerization of alkenes and carbon monoxide

Chemical Reviews

Volumn 96, Issue 2, 1996, Pages 663-681

  Drent, Eite ^a,b,c,d,e   Budzelaar, Peter H M ^a,f,g  

^a SHELL RESEARCH AND TECHNOLOGY CENTRE   (Netherlands)

^b Shell Laboratory   (Netherlands)

^c UNIVERSITY OF GRONINGEN   (Netherlands)

^d Shell Research

^e SHELL GLOBAL SOLUTIONS INTERNATIONAL B V   (United States)

^f EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

^g Shell ^*

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000041191     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr940282j     Document Type: Article

References (107)

1. For earlier reviews, see: Sen, A. Adv. Polym. Sci. 1986, 73/74, 125;
2. (b) CHEMTECH, 1986, 48;
3. (c) Acc. Chem. Res. 1993, 26, 303.
4. In this review, we focus on metal-catalyzed polyketone formation, which usually produces perfectly alternating copolymers. Irregular copolymers can be produced using radical initiators; see e.g.: Brubaker, M. M. U.S. Pat. 2,495,286, 1950; Chem. Abstr. 1950, 44, 4285. Brubaker, M. M.; Coffman, D. D.; Hoehn, H. H. J. Am. Chem. Soc. 1952, 74, 1509. Colombo, P.; Kukacka, L. E.; Fontana, J.; Chapman, R. N.; Steinberg, M. J. Pol. Sci. A-1, 1966, 4, 28. Steinberg, M. Polym. Eng. Sci. 1977, 17, 335.
5. In this review, we focus on metal-catalyzed polyketone formation, which usually produces perfectly alternating copolymers. Irregular copolymers can be produced using radical initiators; see e.g.: Brubaker, M. M. U.S. Pat. 2,495,286, 1950; Chem. Abstr. 1950, 44, 4285. Brubaker, M. M.; Coffman, D. D.; Hoehn, H. H. J. Am. Chem. Soc. 1952, 74, 1509. Colombo, P.; Kukacka, L. E.; Fontana, J.; Chapman, R. N.; Steinberg, M. J. Pol. Sci. A-1, 1966, 4, 28. Steinberg, M. Polym. Eng. Sci. 1977, 17, 335.
6. In this review, we focus on metal-catalyzed polyketone formation, which usually produces perfectly alternating copolymers. Irregular copolymers can be produced using radical initiators; see e.g.: Brubaker, M. M. U.S. Pat. 2,495,286, 1950; Chem. Abstr. 1950, 44, 4285. Brubaker, M. M.; Coffman, D. D.; Hoehn, H. H. J. Am. Chem. Soc. 1952, 74, 1509. Colombo, P.; Kukacka, L. E.; Fontana, J.; Chapman, R. N.; Steinberg, M. J. Pol. Sci. A-1, 1966, 4, 28. Steinberg, M. Polym. Eng. Sci. 1977, 17, 335.
7. In this review, we focus on metal-catalyzed polyketone formation, which usually produces perfectly alternating copolymers. Irregular copolymers can be produced using radical initiators; see e.g.: Brubaker, M. M. U.S. Pat. 2,495,286, 1950; Chem. Abstr. 1950, 44, 4285. Brubaker, M. M.; Coffman, D. D.; Hoehn, H. H. J. Am. Chem. Soc. 1952, 74, 1509. Colombo, P.; Kukacka, L. E.; Fontana, J.; Chapman, R. N.; Steinberg, M. J. Pol. Sci. A-1, 1966, 4, 28. Steinberg, M. Polym. Eng. Sci. 1977, 17, 335.
8. (a) Ash, C. E. J. Mater. Educ. 1994, 16, 1.
9. (b) Medema, D.; Noordam, A. Chemisch Magazine, March 1995. (in Dutch).
10. Reppe, W.; Magin, A. U.S. Pat. 2,577,208, 1951; Chem. Abstr. 1952, 46, 6143.
11. Shryne, T. M.; Holler, H. V. U.S. Pat. 3,984,388, 1976; Chem. Abstr. 1976, 85, 178219.
12. (a) Klabunde, U.; Tulip, T. H.; Roe, D. C.; Ittel, S. D. J. Organometal. Chem. 1987, 334, 141.
13. (b) Klabunde, U.; Ittel, S. D. J. Mol. Catal. 1987, 41, 123.
14. (c) Klabunde, U. U.S. Pat. 4,-698,403, 1987; Chem. Abstr. 1988, 108, 151134; U.S. Pat. 4,-716,205, 1987; Chem. Abstr. 1988, 108, 132485.
15. (c) Klabunde, U. U.S. Pat. 4,-698,403, 1987; Chem. Abstr. 1988, 108, 151134; U.S. Pat. 4,-716,205, 1987; Chem. Abstr. 1988, 108, 132485.
16. Driessen, B.; Green, M. J.; Keim, W. Eur. Pat. Appl. 470,759 A2, 1992; Chem. Abstr. 1992,116, 152623. Keim, W.; Maas, H.; Mecking, S. Z. Naturforsch. 1995, 50b, 430.
17. Driessen, B.; Green, M. J.; Keim, W. Eur. Pat. Appl. 470,759 A2, 1992; Chem. Abstr. 1992,116, 152623. Keim, W.; Maas, H.; Mecking, S. Z. Naturforsch. 1995, 50b, 430.
18. (a) Iwashita, Y.; Sakuraba, M. Tetrahedron Lett. 1971, 26, 2409.
19. (b) Sen, A.; Brumbaugh, J. S. J. Organometal. Chem. 1985, 279, C5.
20. Gough, A. British Pat. 1,081,304, 1967; Chem. Abstr. 1967, 67, 100569.
21. (a) Fenton, D. M. U.S. Pat. 3,530,109, 1970; Chem. Abstr. 1970, 73, 110466; U.S. Pat. 4,076,911, 1978; Chem. Abstr. 1978, 88, 153263.
22. (a) Fenton, D. M. U.S. Pat. 3,530,109, 1970; Chem. Abstr. 1970, 73, 110466; U.S. Pat. 4,076,911, 1978; Chem. Abstr. 1978, 88, 153263.
23. (b) Nozaki, K U.S. Pat. 3,689,460, 1972; Chem. Abstr. 1972, 77, 152860; U.S. Pat. 3,694,412, 1972; Chem. Abstr. 1972, 77, 165324; U.S. Pat. 3,835,123, 1974; Chem. Abstr. 1975, 83, 132273.
24. (b) Nozaki, K U.S. Pat. 3,689,460, 1972; Chem. Abstr. 1972, 77, 152860; U.S. Pat. 3,694,412, 1972; Chem. Abstr. 1972, 77, 165324; U.S. Pat. 3,835,123, 1974; Chem. Abstr. 1975, 83, 132273.
25. (b) Nozaki, K U.S. Pat. 3,689,460, 1972; Chem. Abstr. 1972, 77, 152860; U.S. Pat. 3,694,412, 1972; Chem. Abstr. 1972, 77, 165324; U.S. Pat. 3,835,123, 1974; Chem. Abstr. 1975, 83, 132273.
26. Sen, A.; Ta-Wang Lai, J. Am. Chem. Soc. 1982, 104, 3520;
27. Drent, E. Eur. Pat. Appl. 121,965 A2, 1984; Chem. Abstr. 1985, 102, 46423.
28. Drent, E.; Van Broekhoven, J. A. M.; Doyle, M. J. J. Organomet. Chem. 1991, 417, 235.
29. OCH3 52.0. The ratio of ester to ketone end groups is generally close to 1.
30. Jiang, Z.; Sen, A. Macromolecules 1994, 27, 7215.
31. Brophy, J. H.; Cooley, N. A.; Green, M. J. Eur. Pat. Appl. 590,-942 A2, 1993.
32. Jiang, Z.; Dahlen, G. M.; Sen, A. Palladium(II)-catalyzed alternating copolymerization and terpolymerization of carbon monoxide with a-olefins. In New Advances in Polyolefins; Chung, T. C., Eds.; Plenum Press: New York, 1993; pp 47-57.
33. Jiang, Z.; Dahlen, G. M.; Houseknecht, K.; Sen, A. Macromolecules 1992, 25, 2999.
34. Chien, J. W.; Zhao, A. X.; Xu, F. Polymer Bull. 1992, 28, 315.
35. Daum, U. Ph.D. Thesis, ETH, Zurich, 1988.
36. (a) Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; Van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1992, 430, 357.
37. (b) Van Asselt, R.; Gielens, E. C. G.; Rulke, E. R.; Vrieze, K.; Elsevier, C. J. J. Am. Chem. Soc. 1994, 116, 977.
38. Markies, B. A.; Kruis, D.; Rietveld, M. H. P.; Verkerk, K. A. N.; Boersma, J.; Kooijman, H.; Lakin, M.; Spek, A. L.; Van Koten, G. J. Am. Chem. Soc. 1995, 117, 5263.
39. Van Leeuwen, P. W. N. M.; Roobeek, C. F.; Van der Heijden, H. J J. Am. Chem. Soc. 1994, 116, 12117.
40. See e.g.: Maitlis, P. M. The organic chemistry of palladium; Academic Press: London, 1971. Chaloner, P. A. Handbook of coordination catalysis in organic chemistry; Butterworths: London, 1986. Yamamoto, A. Organotransition metal chemistry; Wiley: New York, 1986.
41. See e.g.: Maitlis, P. M. The organic chemistry of palladium; Academic Press: London, 1971. Chaloner, P. A. Handbook of coordination catalysis in organic chemistry; Butterworths: London, 1986. Yamamoto, A. Organotransition metal chemistry; Wiley: New York, 1986.
42. See e.g.: Maitlis, P. M. The organic chemistry of palladium; Academic Press: London, 1971. Chaloner, P. A. Handbook of coordination catalysis in organic chemistry; Butterworths: London, 1986. Yamamoto, A. Organotransition metal chemistry; Wiley: New York, 1986.
43. See e.g.: Brumbaugh, J. S.; Sen, A. J. Am. Chem. Soc. 1988, 110, 803.
44. See e.g.: Ozawa, F.; Hayashi, T.; Koide, H.; Yamamoto, A. J. Chem. Soc., Chem. Commun. 1991, 1469. Markies, B. A.; Wijkens, P.; Boersma, J.; Spek, A. L.; van Koten, G. Recl. Trav. Chim. Pays-Bas 1991, 110, 133. Markies, B. A.; Rietveld, M. H. P.; Boersma, J.; Spek, A. L.; van Koten, G. J. Organomet. Chem. 1992, 424, C12.
45. See e.g.: Ozawa, F.; Hayashi, T.; Koide, H.; Yamamoto, A. J. Chem. Soc., Chem. Commun. 1991, 1469. Markies, B. A.; Wijkens, P.; Boersma, J.; Spek, A. L.; van Koten, G. Recl. Trav. Chim. Pays-Bas 1991, 110, 133. Markies, B. A.; Rietveld, M. H. P.; Boersma, J.; Spek, A. L.; van Koten, G. J. Organomet. Chem. 1992, 424, C12.
46. See e.g.: Ozawa, F.; Hayashi, T.; Koide, H.; Yamamoto, A. J. Chem. Soc., Chem. Commun. 1991, 1469. Markies, B. A.; Wijkens, P.; Boersma, J.; Spek, A. L.; van Koten, G. Recl. Trav. Chim. Pays-Bas 1991, 110, 133. Markies, B. A.; Rietveld, M. H. P.; Boersma, J.; Spek, A. L.; van Koten, G. J. Organomet. Chem. 1992, 424, C12.
47. Brumbaugh, J.; Whittle, R. R.; Parvez, M.; Sen, A. Organometallics 1990, 9, 1735.
48. Reversible insertion of olefin (norbornene) insertion has recently been reported by Markies et al. in a model system bearing dinitrogen ligands (ref 22). However, insertion of α-olefins in diphosphine systems in the absence of strongly coordinating counterions is unlikely to be reversible.
49. 2: k:k. A ratio of 2:1:1 implies that both termination steps contribute equally (k ≈ 1). The absence of II and III implies that k is either very large or very small, i.e. that only one of the two termination steps contributes.
50. Drent, E. Eur. Pat. Appl. 317,003. 1988; Chem. Abstr. 1989, 111, 154591.
51. See e.g.: Cooper, D. G.; Powell, J. Can. J. Chem. 1973, 51, 1634. Redfield, D. A.; Nelson, J. H. Inorg. Chem. 1973, 12, 15.
52. See e.g.: Cooper, D. G.; Powell, J. Can. J. Chem. 1973, 51, 1634. Redfield, D. A.; Nelson, J. H. Inorg. Chem. 1973, 12, 15.
53. Chen, J.-T.; Sen, A. J. Am. Chem. Soc. 1984, 106, 1506. Sen, A.; Chen, J.-T.; Vetter, W. M.; Whittle, R. R. J. Am. Chem. Soc. 1987, 109, 148.
54. Chen, J.-T.; Sen, A. J. Am. Chem. Soc. 1984, 106, 1506. Sen, A.; Chen, J.-T.; Vetter, W. M.; Whittle, R. R. J. Am. Chem. Soc. 1987, 109, 148.
55. Drent, E. Pure Appl. Chem. 1990, 62, 661.
56. Johnson, L. K.; Killian, C. M.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 6414.
57. 3 bond in a cationic palladium-1,10-phenanthroline complex have recently been determined. (Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 1137.) In this case, CO insertion has an insertion barrier advantage of about 3 kcal over ethene insertion at ∼-25 °C.
58. McDermott, J. X.; White, J. F.; Whitesides, G. M. J. Am. Chem. Soc. 1973, 95, 4451; 1976, 98, 6521.
59. McDermott, J. X.; White, J. F.; Whitesides, G. M. J. Am. Chem. Soc. 1973, 95, 4451; 1976, 98, 6521.
60. Van Broekhoven, J. A. M.; Drent, E. Eur. Pat. Appl. 235,865, 1987; Chem. Abstr. 1988, 108, 76068.
61. Drent, E. Eur. Pat. Appl. 229,408,1986; Chem. Abstr. 1988, 108, 6617.
62. Budzelaar, P. H. M.; Van Leeuwen, P. W. N. M.; Roobeek, C. F.; Orpen, A. G. Organometallics 1992, 11, 23.
63. An isotactic structure is one in which the optically active centers of the repeat units all have the same absolute stereochemistry. (Natta, G.; Pino, P.; Corradini, P.; Danusso, F.; Mantica, E.; Mazzanti, G.; Moraglio, G. J. Am. Chem. Soc. 1955, 77, 1708.) In a syndiotactic polymer, neighboring units have opposite stereochemistry. If an isotactic polyolefin is drawn in its extended conformation, it will have all its substituents pointing in the same direction. If an isotactic polyketone is drawn in its extended conformation, the substituents will alternatingly point up and down.
64. (a) Drent, E.; Wife, R. L. Eur. Pat. Appl. 181,014, 1985; Chem. Abstr. 1985, 105, 98172.
65. (b) Drent, E. Eur. Pat. Appl. 322,018, 1988; Chem. Abstr. 1989, 111, 221150.
66. Van Doorn, J. A.; Wong, P. K.; Sudmeijer, O. Eur. Pat. Appl. 376,364, 1989; Chem. Abstr. 1991, 114, 24797.
67. Wong, P. K. Eur. Pat. Appl. 384,-517, 1989; Chem. Abstr. 1991, 114, 103079.
68. (e) Van Leeuwen, P. W. N. M.; Roobeek, C. F.; Wong, P. K. Eur. Pat. Appl. 393,-790, 1990; Chem. Abstr. 1991, 114, 103034.
69. (a) Batistini, A.; Consiglio, G.; Suter, U. W. Angew. Chem. 1992, 104, 306.
70. (b) Barsacchi, M.; Batistini, A.; Consiglio, G.; Suter, U. W. Macromolecules 1992, 25, 3604.
71. (c) Batistini, A. Ph.D. Thesis, ETH, Zurich, 1991.
72. (d) Batistini, A.; Consiglio, G.; Suter, U. W. Minisymposium "New Advances in Polyolefin Polymers", pr. 56, Div. Polymeric Materials:Science and Eng. Inc., 204th ACS meeting, Washington D. C. (1992)
73. (e) Huter, R. Diplomarbeit; ETH: Zurich, 1992.
74. Chien, J. C. W.; Zhao, A. X.; Xu, F. Polym. Bull. 1992, 28, 315.
75. Drent, E.; Tomassen, H. P. M.; Reynhout, M. J. Eur. Pat. Appl. 468,594, 1992; Chem. Abstr. 1992, 117, 52257.
76. Drent, E. Eur. Pat. Appl. 272,727,1988; Chem. Abstr. 1988, 109, 191089.
77. Drent, E. Eur. Pat. Appl. 463,689, 1992; Chem. Abstr. 1992, 116, 129879.
78. Jiang, Z.; Sen, A. J. Am. Chem. Soc. 1995, 117, 4455.
79. 6 = 5/1.
80. 15 cites formation of ether end groups as evidence for an additional initiation mechanism: insertion of olefin in the Pd-methoxy bond. While this reaction certainly cannot be excluded at present, it is also not necessary to postulate it, since ethers could equally well be formed by (catalyzed) Michael addition of alcohols to unsaturated end groups after termination.
81. Drent, E. Eur. Pat. Appl. 220,767, 1985; Chem. Abstr. 1987, 107, 39199.
82. Drent, E.; Kragtwijk, E.; Pello, D. H. L. Eur. Pat. Appl. 495,-547, 1992; Chem. Abstr. 1992, 117, 150570.
83. Strictly speaking, only one of the two CO insertions needs to be reversible. There is precedent for difference in reversibility between n- and isoacyl formation in rhodium hydroformylation: Lazzaroni, R.; Pertici, P.; Fabrizi, G. J. Mol. Catal. 1990, 58, 75.
84. Jiang, Z.; Boyer, M. T.; Sen, A. J. Am. Chem. Soc. 1995, 117, 7037.
85. (a) Barsacchi, M.; Consiglio, G.; Medici, L.; Petrucci, G.; Suter, U. W. Angew. Chem. 1991, 103, 992.
86. (b) Barsacchi, M. Ph.D. Thesis, ETH, Zurich, 1991.
87. (c) Barsacchi, M.; Consiglio, G.; Suter, U. W. Minisymposium "New Advances in Polyolefin Polymers", pr. 32, Div. Polymeric Materials: Science and Eng. Inc., 204th ACS meeting, Washington D. C. (1992).
88. Corradini, P.; De Rosa, A.; Panunzi, A.; Pino, P. Chimia 1990, 44, 52.
89. De Jong, A. W.; Keysper, J. J. Eur. Pat. Appl. 486,103, 1992; Chem. Abstr. 1992, 117, 172290.
90. Sen, A.; Jiang, Z. Minisymposium "New Advances in Polyolefin Polymers", pr. 55, Div. Polymeric Materials: Science and Eng. Inc., 204th ACS meeting, Washington D. C. (1992).
91. Pisano, C.; Consiglio, G.; Sironi, A.; Moret, M. J. Chem. Soc., Chem. Commun. 1991, 421. Pisano, C. Ph.D. Thesis, ETH, Zurich, 1993. Pisano, C.; Mezzetti, A.; Consiglio, G. Organometallics 1992, 11, 20. Pisano, C.; Consiglio, G. Gazz. Chim. Ital. 1994, 124, 393.
92. Pisano, C.; Consiglio, G.; Sironi, A.; Moret, M. J. Chem. Soc., Chem. Commun. 1991, 421. Pisano, C. Ph.D. Thesis, ETH, Zurich, 1993. Pisano, C.; Mezzetti, A.; Consiglio, G. Organometallics 1992, 11, 20. Pisano, C.; Consiglio, G. Gazz. Chim. Ital. 1994, 124, 393.
93. Pisano, C.; Consiglio, G.; Sironi, A.; Moret, M. J. Chem. Soc., Chem. Commun. 1991, 421. Pisano, C. Ph.D. Thesis, ETH, Zurich, 1993. Pisano, C.; Mezzetti, A.; Consiglio, G. Organometallics 1992, 11, 20. Pisano, C.; Consiglio, G. Gazz. Chim. Ital. 1994, 124, 393.
94. Pisano, C.; Consiglio, G.; Sironi, A.; Moret, M. J. Chem. Soc., Chem. Commun. 1991, 421. Pisano, C. Ph.D. Thesis, ETH, Zurich, 1993. Pisano, C.; Mezzetti, A.; Consiglio, G. Organometallics 1992, 11, 20. Pisano, C.; Consiglio, G. Gazz. Chim. Ital. 1994, 124, 393.
95. Brookhart, M.; Rix, F. C.; DeSimone, J. M.; Barborak, J. C. J. Am. Chem. Soc. 1992, 114, 5894.
96. See e.g.: Li, C.-S.; Cheng, C.-H.; Liao, F.-L.; Wang, S.-L. J. Chem. Soc., Chem. Commun. 1991, 710. Falvello, L. R.; Forniés, J.; Navarro, R.; Sicilia, V.; Tomás, M. Angew. Chem. 1990, 102, 952. Chen, H.; Bartlett, R. A.; Olmstead, M. M.; Power, P. P.; Shoner, S. C. J. Am. Chem. Soc. 1990, 112, 1048.
97. See e.g.: Li, C.-S.; Cheng, C.-H.; Liao, F.-L.; Wang, S.-L. J. Chem. Soc., Chem. Commun. 1991, 710. Falvello, L. R.; Forniés, J.; Navarro, R.; Sicilia, V.; Tomás, M. Angew. Chem. 1990, 102, 952. Chen, H.; Bartlett, R. A.; Olmstead, M. M.; Power, P. P.; Shoner, S. C. J. Am. Chem. Soc. 1990, 112, 1048.
98. See e.g.: Li, C.-S.; Cheng, C.-H.; Liao, F.-L.; Wang, S.-L. J. Chem. Soc., Chem. Commun. 1991, 710. Falvello, L. R.; Forniés, J.; Navarro, R.; Sicilia, V.; Tomás, M. Angew. Chem. 1990, 102, 952. Chen, H.; Bartlett, R. A.; Olmstead, M. M.; Power, P. P.; Shoner, S. C. J. Am. Chem. Soc. 1990, 112, 1048.
99. Nefkens, S. C. A. Ph.D. Thesis, ETH, Zurich, 1992.
100. Van Doom, J. A.; Drent, E. Eur. Pat. Appl. 345,847, 1989; Chem. Abstr. 1990, 112, 199339.
101. (a) Brookhart, M.; Wagner, M. I.; Balavoine, G. G. A. J. Am. Chem. Soc. 1994, 116, 3641.
102. (b) Bartolini, S.; Carfagna, C.; Musco, A. Macromol. Rapid Commun. 1995, 6, 9.
103. Batistini, A.; Consiglio, G. Organometallics 1992, 11, 1766.
104. Wong, P. K.; Van Doom, J. A.; Drent, E.; Sudmeijer, O.; Stil, H. A. Ind. Eng. Chem. Res. 1993, 32, 986.
105. Waywell, D. R. J. Polym. Sci. B 1970, 8, 327.
106. See for example: Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325.
107. The h to h ketone can only be formed by 2,1-insertion in Pd-H, followed by 1,2-insertion in Pd-acyl. Similarly, t to t must be formed by 1,2-insertion followed by 2,1-insertion. The h to t isomer, however, can be formed either by two 1,2-insertions or two 2,1-insertions. The percentage of ketones formed via 1,2-insertion in any acyl is thus (h to h)+(h to t) - the amount of h to t formed by double 2,1-insertion. There is a clear preference for 1,2-insertion in both steps; the latter correction is small but not negligible. With catalysts based on DPPP, we have detected a small quantity of the n-propenyl isopropyl ketone, which must have been formed by two consecutive 2,1-insertions. We approximate the percentage of double 2,1-insertions by 0.01 × (h to h) × (t to t) (%), so that the overall selectivity for 1,2-insertion becomes (h to t) + (h to h) × [1-0.01 × (t to t)]. Similarly, the selectivity for any insertion in an n-acyl becomes (h to t) + (t to t) × [1-0.01 × (h to h)].