Mechanism of the alternating copolymerization of epoxides and CO 2 using β-diiminate zinc catalysts: Evidence for a bimetallic epoxide enchainment

Journal of the American Chemical Society

Volumn 125, Issue 39, 2003, Pages 11911-11924

  Moore, David R ^a   Cheng, Ming ^a   Lobkovsky, Emil B ^a   Coates, Geoffrey W ^a  

^a Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SOLID-STATE STRUCTURES;

AMINO ACIDS; CARBON MONOXIDE; COMPLEXATION; STOICHIOMETRY;

COPOLYMERIZATION;

AMIDE; CARBON DIOXIDE; CYCLOHEXANE OXIDE; EPOXIDE; METAL COMPLEX; ZINC ACETATE; ZINC COMPLEX; ZINC OXIDE;

ARTICLE; CATALYSIS; COMPLEX FORMATION; PHASE TRANSITION; POLYMERIZATION; RING OPENING; STOICHIOMETRY;

EID: 0141508985     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja030085e     Document Type: Article

References (127)

1. Stevens, E. S. Green Plastics; Princeton University Press: Princeton, 2002.
2. Gerngross, T. U.; Slater, S. C. Sci. Am. 2000, 283 (2), 36-41.
3. Gross, R. A.; Kalra, B. Science 2002, 297, 803-807.
4. Okada, M. Prog. Polym. Sci. 2002, 27, 87-133.
5. Arakawa, H.; Aresta, M.; Armor, J. N.; Barteau, M. A.; Beckman, E. J.; Bell, A. T.; Bercaw, J. E.; Creutz, C.; Dinjus, E.; Dixon, D. A.; Domen, K.; DuBois, D. L.; Eckert, J.; Fujita, E.; Gibson, D. H.; Goddard, W. A.; Goodman, D. W.; Keller, J.; Kubas, G. J.; Kung, H. H.; Lyons, J. E.; Manzer, L. E.; Marks, T. J.; Morokuma, K.; Nicholas, K. M.; Periana, R.; Que, L.; Rostrup-Nielson, J.; Sachtler, W. M. H.; Schmidt, L. D.; Sen, A.; Somorjai, G. A.; Stair, P. C.; Stults, B. R.; Tumas, W. Chem. Rev. 2001, 101, 953-996.
6. For some other leading references, see: (a) Musie, G.; Wei, M.; Subramaniam, B.; Busch, D. H. Coord. Chem. Rev. 2001, 219, 789-820.
7. (b) Cooper, A. I. J. Mater. Chem. 2000, 10, 207-234.
8. (c) Leitner, W. Comptes Rendus Acad. Sci. Ser. II C 2000, 3, 595-600.
9. (d) Bolm, C.; Beckmann, O.; Dabard, O. A. G. Angew. Chem., Int. Ed. 1999, 38, 907-909.
10. (e) Yin, X. L.; Moss, J. R. Coord. Chem. Rev. 1999, 181, 27-59.
11. (f) Leitner, W. Coord. Chem. Rev. 1996, 153, 257-284.
12. (g) Leitner, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2207-2221.
13. (h) Jessop, P. G.; Ikariya, T.; Noyori, R. Chem. Rev. 1995, 95, 259-272.
14. Gibson, D. H. Chem. Rev. 1996, 96, 2063-2095.
15. 2 copolymerizations, see: (a) Darensbourg, D. J.; Holtcamp, M. W. Coord. Chem. Rev. 1996, 153, 155-174.
16. (b) Super, M. S.; Beckman, E. J. Trends Polym. Sci. 1997, 5, 236-240.
17. (c) Rokicki, A.; Kuran, W. J. Macromol. Sci.-Rev. Macromol. Chem. Phys. 1981, C21, 135-186.
18. Darensbourg, D. J.; Holtcamp, M. W. Macromolecules 1995, 28, 7577-7579.
19. Darensbourg, D. J.; Rainey, P.; Yarbrough, J. C. Inorg. Chem. 2001, 40, 986-993.
20. Darensbourg, D. J.; Holtcamp, M. W.; Struck, G. E.; Zimmer, M. S.; Niezgoda, S. A.; Rainey, P.; Robertson, J. B.; Draper, J. D.; Reibenspies, J. H. J. Am. Chem. Soc. 1999, 121, 107-116.
21. Darensbourg, D. J.; Wildeson, J. R.; Yarbrough, J. C.; Reibenspies, J. H. J. Am. Chem. Soc. 2000, 122, 12487-12496.
22. Darensbourg, D. J.; Wildeson, J. R.; Yarbrough, J. C. Inorg. Chem. 2002, 41, 973-980.
23. Super, M. S.; Berluche, E.; Costello, C.; Beckman, E. J. Macromolecules 1997, 30, 368-372.
24. Sarbu, T.; Beckman, E. J. Macromolecules 1999, 32, 6904-6912.
25. Sarbu, T.; Styranec, T.; Beckman, E. J. Nature 2000, 405, 165-168.
26. Darensbourg, D. J.; Lewis, S. J.; Rodgers, J. L.; Yarbrough, J. C. Inorg. Chem. 2003, 43, 581-589.
27. Darensbourg, D. J.; Yarbrough, J. C. J. Am. Chem. Soc. 2002, 124, 6335-6342.
28. Kruper, W. J.; Dellar, D. V. J. Org. Chem. 1995, 60, 725-727.
29. Mang, S.; Cooper, A. I.; Colclough, M. E.; Chauhan, N.; Holmes, A. B. Macromolecules 2000, 33, 303-308.
30. Stamp, L. M.; Mang, S. A.; Holmes, A. B.; Knights, K. A.; de Miguel, Y. R.; McConvey, I. F. Chem. Commun. 2001, 2502-2503.
31. Eberhardt, R.; Allmendinger, M.; Luinstra, G. A.; Rieger, B. Organometallics 2003, 22, 211-214.
32. Eberhardt, R.; Allmendinger, M.; Rieger, B. Macromol. Rapid Commun. 2003, 24, 194-196.
33. Kuran, W.; Listos, T. Macromol. Chem. Phys. 1994, 195, 977-984.
34. Dinger, M. B.; Scott, M. J. Inorg. Chem. 2001, 40, 1029-1036.
35. Nozaki, K.; Nakano, K.; Hiyama, T. J. Am. Chem. Soc. 1999, 121 11008-11009.
36. Nakano, K.; Nozaki, K.; Hiyama, T. J. Am. Chem. Soc. 2003, 125. 5501-5510.
37. Kuran, W.; Listos, T.; Abramczyk, M.; Dawidek, A. J. Macromol. Sci., Pure Appl. Chem. 1998, A35, 427-437.
38. Kim, H. S.; Kim, J. J.; Lee, B. G.; Jung, O. S.; Jang, H. G.; Kang, S. O. Angew. Chem., Int. Ed. 2000, 39, 4096-4098.
39. Kim, H. S.; Kim, J. J.; Lee, S. D.; Lah, M. S.; Moon, D.; Jang, H. G. Chem. Eur. J. 2003, 9, 678-686.
40. Paddock, R. L.; Nguyen, S. T. J. Am. Chem. Soc. 2001, 123, 11498-11499.
41. Shen, Y. M.; Duan, W. L.; Shi, M. J. Org. Chem. 2003, 68, 1559-1562.
42. Yano, T.; Matsui, H.; Koike, T.; Ishiguro, H.; Fujihara, H.; Yoshihara, M.; Maeshima, T. Chem. Commun. 1997, 1129-1130.
43. Yamaguchi, K.; Ebitani, K.; Yoshida, T.; Yoshida, H.; Kaneda, K. J. Am. Chem. Soc. 1999, 121, 4526-4527.
44. Kawanami, H.; Ikushima, Y. Chem. Commun. 2000, 2089-2090.
45. Jung, J. H.; Ree, M.; Chang, T. J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 3329-3336.
46. Chen, L. B. Makromol. Chem. Macromol. Symp. 1992, 59, 75-82.
47. Ree, M.; Bae, J. Y.; Jung, J. H.; Shin, T. J.; Hwang, Y. T.; Chang, T. Polym. Eng. Sci. 2000, 40, 1542-1552.
48. Ree, M.; Bae, J. Y.; Jung, J. H.; Shin, T. J. Korea Polym. J. 1999, 7, 333-349.
49. Ree, M.; Bae, J. Y.; Jung, J. H.; Shin, T. J. J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 1863-1876.
50. Shen, Z. Q.; Chen, X. H.; Zhang, Y. F. Macromol. Chem. Phys. 1994, 195, 2003-2011.
51. Tan, C. S.; Hsu, T. J. Macromolecules 1997, 30, 3147-3150.
52. Yang, S. Y.; Fang, X. G.; Chen, L. B. Polym. Adv. Technol. 1996, 7, 605-608.
53. Liu, B. Y.; Zhao, X. J.; Wang, X. H.; Wang, F. S. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 2751-2754.
54. Hsu, T. J.; Tan, C. S. Polymer 2001, 42, 5143-5150.
55. Zhang, M.; Chen, L. B.; Liu, B.; Yan, Z.; Qin, G.; Li, Z. Polym. Bull. 2001, 47, 255-260.
56. Zhang, M.; Chen, L. B.; Qin, G.; Li, Z. M. Acta Polym. Sin. 2001, 422-424.
57. Zhang, M.; Chen, L. B.; Qin, G.; Liu, B.; Yan, Z.; Li, Z. J. Appl. Polym. Sci. 2003, 87, 1123-1128.
58. Wang, S. J.; Du, L. C.; Zhao, X. S.; Meng, Y. Z.; Tjong, S. C. J. Appl. Polym. Sci. 2002, 85, 2327-2334.
59. Inoue, S.; Koinuma, H.; Tsuruta. T. J. Polym. Sci., Part B: Polym. Lett. 1969, 7, 287-292.
60. Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018-11019.
61. Coates, G. W.; Cheng, M. (Cornell Research Foundation), U.S. Pat. 6133402, 2002 (Chem Abstr. 2000, 132, 152332).
62. Cheng, M.; Darling, N. A.; Lobkovsky, E. B.; Coates, G. W. Chem. Commun. 2000, 2007-2008.
63. Cheng, M.; Moore, D. R.; Reczek, J. J.; Chamberlain, B. M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2001, 123, 8738-8749.
64. Moore, D. R.; Cheng, M.; Lobkovsky, E. B.; Coates, G. W. Angew. Chem., Int. Ed. 2002, 41, 2599-2602.
65. Allen, S. D.; Moore, D. R.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2002, 124, 14284-14285.
66. Cheng, M.; Attygalle, A. B.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1999, 121, 11583-11584.
67. Chamberlain, B. M.; Cheng, M.; Moore, D. R.; Ovitt, T. M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2001, 123, 3229-3238.
68. Rieth, L. R.; Moore, D. R.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2002, 124, 15239-15248.
69. Matyjaszewski, K.; Mueller, A. H. E. Polym. Prepr. (American Chemical Society, Division of Polymer Chemistry) 1997, 38 (1), 6-9.
70. Coates, G. W. Chem. Rev. 2000, 100, 1223-1252.
71. See Supporting Information.
72. Chisholm, M. H.; Gallucci, J.; Phomphrai, K. Inorg. Chem. 2002, 41, 2785-2794.
73. Chisholm, M. H.; Huffman, J. C.; Phomphrai, K. J. Chem. Soc., Dalton Trans. 2001, 222-224.
74. 2 were refined anisotropically and isotropically, respectively.
75. iPr and other BDI zinc alkoxide complexes are underway.
76. 2/epoxide copolymerization. presumably because rearrangement to the zinc isopropoxide could not occur.
77. Liu, Z. W.; Torrent, M.; Morokuma, K. Organometallics 2002, 21, 1056-1071.
78. We are currently investigating the origin of the bimodal GPC traces of the polymer produced using [(BDI-6)ZnOAc] (see Table 2). Preparatory GPC of the polymer shows the high molecular weight peak to be predominantly polyether, whereas the low molecular weight fraction is primarily polycarbonate.
79. For reviews on cooperative bimetallic catalysis in enzymatic systems, see: (a) Cricco, J. A.; Orellano, E. G.; Rasia, R. M.; Ceccarelli, E. A.; Vila, A. J. Coord. Chem. Rev. 1999, 192, 519-535.
80. (b) Wilcox, D. E. Chem. Rev. 1996, 96, 2435-2458.
81. (c) Lipscomb, W. N.; Strater, N. Chem. Rev. 1996, 96, 2375-2433.
82. (d) Coleman, J. E. Curr. Opin. Chem. Biol. 1998, 2, 222-234.
83. (e) Strater, N.; Lipscomb, W. N.; Klabunde, T.; Krebs, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2024-2055.
84. (f) Steinhagen, H.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 2339-2342.
85. For an example of biomimetic, bimetallic catalyst design for lactone polymerization, see: Williams, C. K.; Brooks, N. R.; Hillmyer, M. A.; Tolman, W. B. Chem. Commun. 2002, 2132-2133.
86. For a review on synthetic bimetallic catalysts as enzymatic mimics, see: van den Beuken, E. K.; Feringa, B. L. Tetrahedron 1998, 54, 12985-13011.
87. For references on asymmetric aldol condensation using bimetallic zinc compounds, see the following and references within: (a) Kitamura, M.; Okada, S. ; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028-4036.
88. (b) Kitamura, M.; Suga, S.; Niwa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 4832-4842.
89. (c) Kitamura, M.; Suga, S.; Oka, H.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 9800-9809.
90. (d) Trost, B. M.; Ito, H. J. Am. Chem. Soc. 2000, 122, 12003-12004.
91. (e) Trost, B. M.; Silcoff. E. R.; Ito, H. Org. Lett. 2001, 3, 2497-2500.
92. (f) Rasmussen, T.; Norrby, P. O. J. Am. Chem. Soc. 2001, 123, 2464-2465.
93. (g) Pu, L.; Yu, H. B. Chem. Rev. 2001, 101, 757-824.
94. For asymmetric ring-opening of epoxides using Cr or Co salen complexes, see the following and references within: (a) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421-431.
95. (b) Ready, J. M.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 1374-1377.
96. (c) Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 1307-1315.
97. (d) Ready, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 2687-2688.
98. (e) Konsler, R. G.; Karl, J.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 10780-10781.
99. (f) Hansen, K. B.; Leighton, J. L.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 10924-10925.
100. For Zr-catalyzed enantioselective ring-opening of epoxides, see the following: (a) Nugent, W. A. J. Am. Chem. Soc. 1998, 120, 7139-7140.
101. (b) McCleland, B. W.; Nugent, W. A.; Finn, M. G. J. Org. Chem. 1998, 63, 6656-6666.
102. For studies where a bimetallic epoxide enchainment mechanism is proposed, see the following and references within: (a) Vandenberg, E. J. J. Polym. Sci. 1960, 47, 486-489.
103. (b) Price, C. C.; Spector, R. J. Am. Chem. Soc. 1966, 88, 4171-4173.
104. (c) Osgan, M.; Teyssie, P. J. Polym. Sci. Part B: Polym. Lett. 1967, 5, 789-792.
105. (d) Vandenberg, E. J. J. Polym. Sci., Part A: Polym. Chem. 1986, 24, 1423-1431.
106. (e) Watanabe, Y.; Yasuda, T.; Aida, T.; Inoue, S. Macromolecules 1992, 25, 1396-1400.
107. (f) Sugimoto, H.; Kawamura, C.; Kuroki, M.; Aida, T.; Inoue, S. Macromolecules 1994, 27, 2013-2018.
108. (g) Chisholm, M. H.; Navarro-Llobet, D.; Simonsick, W. J. Macromolecules 2001, 34, 8851-8857.
109. (h) Braune, W.; Okuda, J. Angew. Chem., Int. Ed. 2003, 42, 64-68. To the best of our knowledge, no kinetic studies have been performed on these systems. However, Inoue has reported kinetic studies for the ring-opening polymerization of δ-valerolactone that illustrate a second-order dependence in aluminum porphyrin alcoholates. See: Shimasaki, K.; Aida, T.; Inoue, S. Macromolecules 1987, 20, 3076-3080.
110. (h) Braune, W.; Okuda, J. Angew. Chem., Int. Ed. 2003, 42, 64-68. To the best of our knowledge, no kinetic studies have been performed on these systems. However, Inoue has reported kinetic studies for the ring-opening polymerization of δ-valerolactone that illustrate a second-order dependence in aluminum porphyrin alcoholates. See: Shimasaki, K.; Aida, T.; Inoue, S. Macromolecules 1987, 20, 3076-3080.
111. See refs 12, 22, 24, 27-30, 55 and the following: (a) Kobayashi, M.; Inoue, S.; Tsuruta, T. Macromolecules 1971, 4, 658-659.
112. (b) Inoue, S.; Kobayashi, M.; Koinuma, H.; Tsuruta, T. Makromol. Chem. 1972, 155, 61-73.
113. (c) Kobayashi, M.; Inoue, S.; Tsuruta, T. J. Polym. Sci.: Polym. Chem. Ed. 1973, 11, 2383-2385.
114. (d) Kobayashi, M.; Tang, Y. L.; Tsuruta, T.; Inoue, S. Makromol. Chem. 1973, 169, 69-81.
115. (e) Kuran, W.; Pasynkiewicz, S.; Skupinska, J.; Rokicki, A. Makromol. Chem. Macromol. Chem. Phys. 1976, 177, 11-20.
116. (f) Kuran, W. Appl. Organomet. Chem. 1991, 5, 191-194.
117. (g) Kuran, W.; Listos, T. Macromol. Chem. Phys. 1994, 195, 1011-1015.
118. ASI Applied Systems, Millersville, MD 21108.
119. 1H NMR spectroscopy. In addition, the polycarbonates possess molecular weights based on [CHO]:[Zn] and PDIs are approximately 1.1, as determined by gel permeation chromatography (calibrated with polystyrene standards in tetrahydrofuran). It should be noted that higher levels of carbonate linkages are found in polycarbonate synthesized in toluene solution versus neat CHO. A similar phenomenon has been observed in ref 17.
120. For some examples of in situ IR studies, see: (a) Rutherford, J. L.; Hoffmann, D.; Collum, D. B. J. Am. Chem. Soc. 2002, 124, 264-271.
121. (b) Sun, X. F.; Collum, D. B. J. Am. Chem. Soc. 2000, 122, 2452-2458.
122. (c) Lucht, B. L.; Collum, D. B. J. Am. Chem. Soc. 1995, 117, 9863-9874.
123. (d) Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 8008-8018.
124. (e) Allmendinger, M.; Eberhardt, R.; Luinstra, G.; Rieger, B. J. Am. Chem. Soc. 2002, 124, 5646-5647.
125. tot = 2[D] + [M], where D = dimer and M = monomer.
126. 2 pressure is increased (see Supporting Information). Therefore, we have adjusted the initial rate values to account for these decreased absorbance levels.
127. 2, see refs 8-21.