Rare Earth polymerization catalysts supported by bulky aminopyridinato ligands

Zeitschrift fur Anorganische und Allgemeine Chemie

Volumn 636, Issue 12, 2010, Pages 2135-2147

  Kempe, Rhett ^a  

^a UNIVERSITY OF BAYREUTH   (Germany)

Author keywords

Aminopyridinato ligands; CCTP; Lanthanoids; Polymerization catalysts; Polymers; Rare earth metals

Indexed keywords

EID: 78649506224     PISSN: 00442313     EISSN: 15213749     Source Type: Journal    
DOI: 10.1002/zaac.201000195     Document Type: Article

References (174)

1. (a) R. Kempe, H. Noss, T. Irrgang, J. Organomet. Chem. 2002, 647, 12-20;
2. (b) R. Kempe, Eur. J. Inorg. Chem. 2003, 791-803.
3. For discussion of the binding modes see: S. Deeken, G. Motz, R. Kempe, Z. Anorg. Allg. Chem. 2007, 633, 320-325.
4. For the general applicability of the ligands see: G. Glatz, S. De-meshko, G. Motz, R. Kempe, Eur. J. Inorg. Chem. 2009, 1385-1392.
5. The term rare earth (metal or atom) includes the group 3 elements Sc, Y, und La as well as the lanthanoids themselves the elements from Ce till Lu.
6. N. M. Scott, T. Schareina, O. Tok, R. Kempe, Eur. J. Inorg. Chem. 2004, 3297-3304.
7. N. M. Scott, R. Kempe, Eur. J. Inorg. Chem. 2005, 1319-1324.
8. W. P. Kretschmer, A. Meetsma, B. Hessen, N. M. Scott, S. Qay-yum, R. Kempe, Z. Anorg. Allg. Chem. 2006, 632, 1936-1938.
9. (a) A. E. Shilov, G. B. Shul'pin, Chem. Rev. 1997, 97, 2879-2932;
10. (b) C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633-639;
11. (c) K. Godula, D. Sames, Science 2006, 312, 67-72;
12. (d) F. Kakiuchi, T. Kochi, Synthesis 2008, 19, 3013-3039.
13. (a) M. Brookhart, M. L. H. Green, J. Organomet. Chem. 1983, 250, 395-408;
14. (b) W. J. Evans, L. A. Hughes, T. P. Hanusa, J. Am. Chem. Soc. 1984, 106, 4270-4272;
15. (c) W. J. Evans, L. A. Hughes, T. P. Hanusa, Organometallics 1986, 5, 1285-1291;
16. (d) P. B. Hitchcock, J. A. K. Howard, M. F. Lappert, S. Prashar, J. Orga-nomet. Chem. 1992, 437, 177-189.
17. (a) P. L. Watson, J. Chem. Soc., Chem. Commun. 1983, 276-277;
18. (b)P. L. Watson, G. B. Parshall, Acc. Chem. Res., 1985, 18, 51-56;
19. (c) P. L. Watson, J. Am. Chem. Soc. 1983, 105, 6491-6493;
20. (d) N. Barros, O. Eisenstein, L. Maron, Dalton Trans. 2006, 3052-3057.
21. (a) K. H. den Haan, J. H. Teuben, J. Chem. Soc., Chem. Commun. 1986, 682-683;
22. (b) M. E. Thompson, S. M. Baxter, A. R. Bulls, B. J. Burger, M. C. Nolan, B. D. Santarsiero, W. P. Schaefer, J. E. Bercaw, J. Am. Chem. Soc. 1987, 109, 203-219;
23. (c) K. H. den Haan, Y. Wiestra, J. H. Teuben, Organometallics 1987, 6, 2053-2060;
24. (d) W. J. Evans, T. A. Ulibarri, J. W. Ziller, Organo-metallics 1991, 10, 134-142;
25. (e) M. Booij, A. Meetsma, J. H. Teuben, Organometallics 1991, 10, 3246-3552;
26. (f) M. Booij, B. J. Deelman, R. D. Duchateau, J. Postma, A. Meetsma, J. H. Teuben, Organometallics 1993, 12, 3531-3540;
27. (g) W. J. Evans, J. M. Per-otti, J. W. Ziller, Inorg. Chem. 2005, 44, 5820-5825;
28. (h) W. J. Evans, J. M. Perotti, J. W. Ziller, J. Am. Chem. Soc. 2005, 127, 3894-3909;
29. (i) W. J. Evans, T. M. Champagne, J. W. Ziller, J. Am. Chem. Soc. 2006, 128, 14270-14271.
30. (a) M. D. Fryzuk, T. S. Haddad, S. J. Rettig, Organometallics 1991, 10, 2026-2036;
31. (b) Y. Mu, W. E. Piers, D. C. Mac Quarrie, M. J. Zaworotko, V. G. Young, Organometallics 1996, 15, 2720-2726;
32. (c) R. Duchateau, T. Tuinstra, E. A. C. Brussee, A. Meet-sma, P. T. van Duijnen, J. H. Teuben, Organometallics 1997, 16, 3511-3522;
33. (d) D. J. H. Emslie, W. E. Piers, M. Parvez, R. McDonald, Organometallics 2002, 21, 4226-4240;
34. (e) D. J. H. Emslie, W. E. Piers, M. Parvez, Dalton Trans. 2003, 2615-2620;
35. (f) L. K. Knight, W. E. Piers, P. Fleurat-Lessard, P. Masood, R. McDonald, Organometallics 2004, 23, 2087-2094;
36. (g) L. K. Knight, W. E. Piers, R. McDonald, Organometallics 2006, 25, 3289-3292;
37. (h) M. Zimmermann, F. Estler, E. Herdtweck, W. K. Törnroos, R. Anwander, Organometallics 2007, 26, 6029-6041.
38. G. G. Skvortsov, G. K. Fukin, A. A. Trifonov, A. Noor, C. Dör-ing, R. Kempe, Organometallics 2007, 26, 5770-5773.
39. S. Qayyum, G. G. Skvortsov, G. K. Fukin, A. A. Trifonov, W. P. Kretschmer, C. Döring, R. Kempe, Eur. J. Inorg. Chem. 2010, 248-257.
40. D. M. Lyubov, C. Döring, G. K. Fukin, A. V. Cherkasov, A. V. Shavyrin, R. Kempe, A. A. Trifonov, Organometallics 2008, 27, 2905-2907.
41. W. P. Kretschmer, A. Meetsma, B. Hessen, T. Schmalz, S. Qay-yum, R. Kempe, Chem. Eur. J. 2006, 12, 8969-8978.
42. (a) M. Masayoshi, Z. Hou, Nature Chem. 2010, 2, 257-268;
43. (b) M. Konkol, J. Okuda, Coord. Chem. Rev. 2008, 252, 1577-1591;
44. (c) A. A. Trifonov, Russ. Chem. Rev., 2007, 76, 1051-1072;
45. (d) Z. Hou, M. Nishiura, T. Shima, Eur. J. Inorg. Chem. 2007, 2535-2545;
46. (e) Z. Hou, Bull. Chem. Soc. Jpn. 2003, 76, 2253-2266;
47. (f) J. Okuda, Dalton Trans. 2003, 2367-2378;
48. (g) S. Arndt, J. Okuda, Chem. Rev. 2002, 102, 1953-1976;
49. (h) G. A. Molander, J. A. C. Romero, Chem. Rev. 2002, 102, 2161-2186;
50. (i) Z. Hou, Y. Wakat-suki, Coord. Chem. Rev. 2002, 231, 1-22;
51. (j) Z. Hou, Y. Wakat-suki, in: Science of Synthesis (Eds.: T. Imamoto, R. Noyori), Thi-eme, Stuttgart, 2002,vol. 2, p. 849-942;
52. (k) A. J. Hoskin, D. W. Stephan, Coord. Chem. Rev. 2002, 233-234, 107-129;
53. (l) M. Ephritikhine, Chem. Rev. 1997, 97, 2193-2242;
54. (m) H. Schumann, J. A. Meese-Marktscheffel, L. Esser, Chem. Rev. 1995, 95, 865-986;
55. (n) F. T. Edelmann, in: Comprehensive Organometallic Chemistry II (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson, M. F. Lappert), Pergamon, Oxford, 1995,vol. 4, p. 11-212;
56. (o) C. J. Schaverien, Adv. Organomet. Chem. 1994, 36, 283-362.
57. (a) W. J. Evans, J. H. Meadows, A. L. Wayda, J. Am. Chem. Soc. 1982, 104, 2015-2017;
58. (b) W. J. Evans, J. H. Meadows, T. P. Ha-nusa, J. Am. Chem. Soc. 1984, 106, 4454-4460;
59. (c) W. J. Evans, M. S. Sollberger, S. I. Khan, R. Bau, J. Am. Chem. Soc. 1988, 110, 439-446.
60. (a) K. C. Hultzsch, Dissertation, Johannes Gutenberg-Universität Mainz, Germany 1999;
61. (b) K. C. Hultzsch, T. P. Spaniol, J. Okuda, Angew. Chem. 1999, 111, 163-165;
62. Angew. Chem. Int. Ed. 1999, 38, 227-230.
63. Z. Hou, Y. Zhang, O. Tardif, Y. Wakatsuki, J. Am. Chem. Soc. 2001, 123, 9216-9217.
64. M. Yousufuddin, M. J. Gutmann, J. Baldamus, O. Tardif, Z. Hou, S. A. Mason, G. J. McIntyre, R. Bau, J. Am. Chem. Soc. 2008, 130, 3888-3891.
65. S. Qayyum, A. Noor, G. Glatz, R. Kempe, Z. Anorg. Allg. Chem. 2009, 635, 2455-2458.
66. (a) G. B. Deacon,C. M. Forsyth, in Inorganic Chemistry Highlights, (Eds.: G. Meyer, D. Naumann, L. Wesemann) Wiley-VCH, Weinheim, Germany 2002,ch. 7, p. 139-153;
67. (b) K. Müller-Buschbaum, Z. Anorg. Allg. Chem. 2005, 631, 811-828.
68. (a) G. B. Deacon, C. M. Forsyth, P. C. Junk, B. W. Skelton, A. H. White, Chem. Eur. J. 1999, 5, 1452-1459;
69. (b) G. B. Deacon, T. Feng, C. M. Forsyth, A. Gitlits, D. C. R. Hockless, Q. Shen, B. W. Skelton, A. H. White, J. Chem. Soc., Dalton Trans. 2000, 961-966;
70. (c) G. B. Deacon, A. Gitlits, P. W. Roesky, M. K. Burg-stein, K. C. Lim, B. W. Skelton, A. H. White, Chem. Eur. J. 2001, 7, 127-128;
71. (d) G. B. Deacon, C. M. Forsyth, A. Gitlits, R. Har-ika, P. C. Junk, B. W. Skelton, A. H. White, Angew. Chem. 2002, 114, 1383-1385;
72. Angew. Chem. Int. Ed. 2002, 41, 3249-3251;
73. (e) K. Müller-Buschbaum, Z. Anorg. Allg. Chem. 2003, 629, 2127-2132;
74. (f) G. B. Deacon, C. M. Forsyth, A. Gitlits, B. W. Skelton, A. H. White, Dalton Trans. 2004, 1239-1247;
75. (g) K. Müller-Buschbaum, C. Quitmann, Inorg. Chem. 2006, 45, 2678-2687;
76. (h) G. B. Deacon, C. M. Forsyth, P. C. Junk, S. G. Leary, New J. Chem. 2006, 30, 592-596;
77. (i) C. C. Quitmann, V. Bezugly, F. R. Wagner, K. Müller-Buschbaum, Z. Anorg. Allg. Chem. 2006, 632, 1173-1186.
78. (a) J. Hitzbleck, A. T. O'Brien, C. M. Forsyth, G. B. Deacon, K. Ruhlandt-Senge, Chem. Eur. J. 2004, 10, 3315-3323;
79. (b) J. Hitz-bleck, G. B. Deacon, K. Ruhlandt-Senge, Angew. Chem. 2004, 116, 5330-5332;
80. Angew. Chem. Int. Ed. 2004, 43, 5218-5230.
81. S. Qayyum, K. Haberland, C. M. Forsyth, P. C. Junk, G. B. Deacon, R. Kempe, Eur. J. Inorg. Chem. 2008, 557-562.
82. (a) K. M. Stridsberg, M. Ryner, A.-C. Albertsson, Adv. Polym. Sci. 2002,157, 42-65;
83. (b) A. C. Albertsson, I. K. Varma, Adv. Polym. Sci. 2002, 157, 2-41.
84. (a) Z. Hou, Y. Wakatsuki, Coord. Chem. Rev. 2002, 231, 1-22;
85. (b) S. Agarwal, C. Mast, K. Dehnicke, A. Greiner, Macromol. Rapid Commun. 2000, 21, 195-212;
86. (c) H. Yasuda, J. Organome-tallic. Chem. 2002, 647, 128-138.
87. (a) M. Okada, Prog. Polym. Sci. 2002, 27, 87-133;
88. (b) M. Vert, Biomacromolecules 2005, 6, 538-546;
89. (c) A.-C. Albertsson, I. K. Varma, Biomacromolecules 2003, 4, 1466-1486;
90. (d) T. Freier, Adv. Polym. Sci. 2006, 203, 1-61;
91. (e) M. S. Lindblad, Y. Liu, A.-C. Albertsson, E. Ranucci, S. Karlsson, Adv. Polym. Sci. 2002, 157, 141-160;
92. (f) S. Matsumura, Adv. Polym. Sci. 2006, 194, 95-132.
93. (a) S. M. Cendrowski-Guillaume, G. Le Gland, M. Nierlich, M. Ephritikhine, Organometallics 2000, 19, 5654-5660;
94. (b) S. M. Cendrowski-Guillaume, M. Nierlich, M. Lance, M. Ephritikhine, Organometallics 1998, 17, 786-788.
95. (a) S. M. Guillaume, M. Schappacher, A. Soum, Macromolecules 2003,36, 54-60;
96. (b) I. Palard, A. Soum, S. M. Guillaume, Chem. Eur. J. 2004, 10, 4054-4062;
97. (c) I. Palard, A. Soum, S. M. Guil-laume, Macromolecules 2005, 38, 6888-6894;
98. (d) I. Palard, M. Schappacher, A. Soum, S. M. Guillaume, Polym. Int. 2006, 55, 1132-1137.
99. H. Noss, M. Oberthür, C. Fischer, W. P. Kretschmer, R. Kempe, Eur. J. Inorg. Chem. 1999, 2283-2288.
100. S. M. Guillaume, M. Schappacher, N. M. Scott, R. Kempe, J. Polym. Sci. Part A: Polym. Chem. 2007, 45, 3611-3619.
101. (a) Y. Shen, Z. Shen, Y. Zhang, Q. Hang, J. Polym. Sci. Part A : Polym. Chem. 1997, 35, 1339-1352;
102. (b) Y. Shen, Y. K. J. Zu, Z. Shen, K. Yao, J. Polym. Sci. Part A : Polym. Chem. 1996, 34, 1799-1805;
103. (c) Y. Shen, Z. Shen, J. Shen, Y. Zhang, K. Yao, Mac-romolecules 1996, 29, 3441-3446.
104. (a) S. Agarwal, M. Karl, K. Dehnicke, G. Seybert, W. Massa, A. Greiner, J. Appl. Polym. Sci. 1999, 73, 1669-1674;
105. (b) S. Agarwal, C. Mast, S. Anfang, M. Karl, K. Dehnicke, A. Greiner, Polym. Prepr. 1998, 39, 414-415;
106. (c) S. Agarwal, M. Karl, S. Anfang, K. Dehnicke, A. Greiner, Polym. Prepr. 1998, 39, 361-362;
107. (d) S. Agarwal, A. Greiner, J. Chem. Soc., Perkin Trans. 1, 2002, 2033-2042.
108. T. J. Woodman, M. Schormann, D. L. Hughes, M. Bochmann, Organometallics 2004, 23, 2972-2979.
109. R. Kempe, Chem. Eur. J. 2007, 13, 2764-2773.
110. (a) E. G. Samsel, Ethyl Corporation, EP 0539876, 1993;
111. (b) E. G. Samsel, Ethyl Corporation, EP 0574854, 1993.
112. (a) J.-F. Pelletier, A. Mortreux, X. Olonde, K. Bujadoux, Angew. Chem. 1996, 108, 1980-1982;
113. Angew. Chem. Int. Ed. Engl. 1996, 35, 1854-1856;
114. (b) J. F. Pelletier, K. Bujadoux, X. Olonde, E. Ad-isson, A. Mortreux, T. Chenal, US 5779942, 1998.
115. (a) J. S. Rogers, G. C. Bazan, Chem. Commun. 2000, 1209-1210;
116. (b) G. C. Bazan, J. S. Rogers, C. C. Fang, Organometallics 2001, 20, 2059-2064;
117. (c) G. Mani, F. P. Gabbai, Angew. Chem. 2004, 11 6, 2313-2316;
118. Angew. Chem. Int. Ed. 2004, 43, 2263-2266;
119. (d) G. Mani, F. P. Gabbai, J. Organomet. Chem. 2005, 690, 5145-5149;
120. (e) G. J. P. Britovsek, S. A. Cohen, V. C. Gibson, P. J. Mad-dox, M. van Meurs, Angew. Chem. 2002, 114, 507-509;
121. Angew. Chem. Int. Ed. 2002, 41, 489-491;
122. (f) G. J. P. Britovsek, S. A. Cohen, V. C. Gibson, M. van Meurs, J. Am. Chem. Soc. 2004, 126, 10701-10712;
123. (g) M. van Meurs, G. J. P. Britovsek, V. C. Gibson, S. A. Cohen, J. Am. Chem. Soc. 2005, 127, 9913-9923;
124. (h) J. Saito, Y. Tohi, N. Matsukawa, M. Mitani, T. Fujita, Macro-molecules 2005, 38, 4955-4957;
125. (i) T. Chenal, X. Olonde, J.-F. Pelletier, K. Bujadoux, M. Mortreux, Polymer 2007, 48, 1844-1856;
126. (j) W. Zhang, L. R. Sita, J. Am. Chem. Soc. 2008, 130, 442-443;
127. (k) W. Zhang, J. Wei, L. R. Sita, Macromolecules 2008, 41, 7829-7833;
128. (l) J. Wei, W. Zhang, L. R. Sita, Angew. Chem. 2010, 122, 1-4;
129. Angew. Chem. Int. Ed. 2010, 49, 14-18.
130. (a) S. Arndt, J. Okuda, Adv. Synth. Catal. 2005, 347, 339-354;
131. (b) S. Arndt, J. Okuda, Chem. Rev. 2002, 102, 1953-1976;
132. (c) P. M. Zeimentz, S. Arndt, B. R. Elvidge, J. Okuda, Chem. Rev. 2006, 106, 1062404-2433.
133. Z. Hou, Y. Luo, X. Li, J. Organomet. Chem. 2006, 691, 3114-3121.
134. C. Doering, R. Kempe, Eur. J. Inorg. Chem. 2009, 412-418.
135. W. P. Kretschmer, T. Bauer, B. Hessen, R. Kempe, Dalton Trans. 2010, 1, accepted.
136. 3.
137. R. Briquel, J. Mazzolini, T. Le Bris, O. Boyron, F. Boisson, F. Delolme, F. D'Agosto, C. Boisson, R. Spitz, Angew. Chem. 2008, 120, 9451-9453;
138. Angew. Chem. Int. Ed. 2008, 47, 9311-9313.
139. (a) S. Arndt, K. Beckerle, P. M. Zeimentz, T. P. Spaniol, J. Okuda, Angew. Chem. 2005, 117, 7640-7644;
140. Angew. Chem. Int. Ed. 2005, 44, 7473-7477;
141. (b) L. Zhang, Y. Luo, Z. Hou, J. Am. Chem. Soc. 2005, 127, 14562-14563.
142. (a) E. Le Roux, F. Nief, F. Jaroschik, K. W. Törnroos, R. Anwan-der, Dalton Trans. 2007, 4866;
143. (b) M. Zimmermann, K. W. Törn-roos, R. Anwander, Angew. Chem. 2008, 120, 787-790;
144. Angew. Chem. Int. Ed. 2008, 47, 775-778;
145. (c) M. Zimmermann, K. W. Törnroos, H. Sitzmann, R. Anwander, Chem. Eur. J. 2008, 14, 7266-7277;
146. (d) B. Wang, D. Cui, K. Lv, Macromolecules 2008, 41, 1983-1988;
147. (e) N. Yu, M. Nishiura, X. Li, Z. Xi, Z. Hou, Chem. Asian J. 2008, 3, 1406-1414;
148. (f) H. Zhang, Y. Luo, Z. Hou, Macromolecules 2008, 41, 1064-1066;
149. (g) A.-S. Rodriguesa, E. Kirillova, B. Vuilleminb, A. Razavic, J.-F. Carpentier, Polymer 2008, 49, 2039-2045.
150. (a) L. Zhang, T. Suzuki, Y. Luo, M. Nishiura, Z. Hou, Angew. Chem. 2007, 11 9, 1941-1945;
151. Angew. Chem. Int. Ed. 2007, 46, 1909-1913;
152. (b) Y. Luo, M. Nishiura, Z. Hou, J. Organomet. Chem. 692, 536-544;
153. (c) Y. Yang, B. Liu, K. Lv, W. Gao, D. Cui, X. Chen, X. Jing, Organometallics 2007, 26, 4575-4584;
154. (d) Y. Yang, Q. Wang, D. Cui, J. Polym. Sci. Part A: Polym. Chem. 46, 5251-5262;
155. (e) S. Li, W. Miao, T. Tang, W. Dong, X. Zhang, D. Cui, Organometallics 2008, 27, 718-725;
156. (f) W. Gao, D. Cui, J. Am. Chem. Soc. 2008, 130, 4984-4991.
157. L. Zhang, M. Nishiura, M. Yuki, Y. Luo, Z. Hou, Angew. Chem. 2008, 120, 2682-2685;
158. Angew. Chem. Int. Ed. 2008, 47, 2642-2645.
159. For an example of a stoichiometric reaction of a yttrium alkyl complex with isoprene see: B. Liu, X. Liu, D. Cui, L. Liu, Orga-nometallics 2009, 28, 1453-1460.
160. (a) J. Wolpers, H. B. Fuchs, C. Herrmann, W. Hellermann, K. H. Nordsiek, Eur. Patent Appl. EP 456902 A1, 1991;
161. (b) J. D. Massie, W. Hsu, A. F. Halasa, P. H. Sandstrom, US Patent US 5356997, 1994;
162. (c) A. F. Halasa, W. Hsu, D. J. Zanzig, G. L. Allen, L. E. Austin, US Patent US 5627237 A, 1997.
163. (a) L. Porri,A. Giarrusso in Comprehensive Polymer Science, Vol. 4 (Eds.: G. C. Eastmond, A. Ledwith, S. Russo, P. Sigwalt), Per-gamon, Oxford, 1989, pp. 74-79;
164. (b) R. Taube, G. Sylvester in Applied Homogeneous Catalysis with Organometallic Compounds, Vol. 2 (Eds.: B. Cornils, W. A. Herrmann), Wiley-VCH, Weinheim, Germany 1996, pp. 285-315;
165. (c) L. Friebe, O. Nuyken, W. Obrecht, Adv. Polym. Sci. 2006, 204, 82-83;
166. (d) A. Fischbach, R. Anwander, Adv. Polym. Sci. 2006, 204, 155-191.
167. (a) G. Natta, L. Porri, A. Carbonaro, Makromol. Chem. 1964, 77, 126-138;
168. (b) W. Gronski, N. Murayama, H. J. Cantow, T. Miyamoto, Polymer 1976, 17, 358-360;
169. (c) G. Ricci, M. Battistella, L. Porri, Macromolecules 2001, 34, 5766-5769;
170. (d) C. Bazzini, A. Giarrusso, L. Porri, Macromol. Rapid Commun. 2002, 23, 922-927;
171. (e) Y. Nakayama, Y. Baba, H. Yasuda, K. Kawakita, N. Uey-ama, Macromolecules 2003, 36, 7953-7958;
172. (f) C. Bazzini, A. Gi-arrusso, L. Porri, B. Pirozzi, R. Napolitano, Polymer 2004, 45, 2871-2875;
173. (g) Z. Hou, Y. Luo, X. Li, J. Organomet. Chem. 2006, 691, 3114-3121.
174. C. Doering, W. P. Kretschmer, R. Kempe, Eur. J. Inorg. Chem. 2010, in press.