Bis(oxazolinyl)phenyl-ligated rare-earth-metal complexes: Highly regioselective catalysts for cis -1,4-polymerization of isoprene

Inorganic Chemistry

Volumn 52, Issue 6, 2013, Pages 2802-2808

  Pan, Yu ^a   Xu, Tieqi ^a   Yang, Guan Wen ^a   Jin, Kun ^a   Lu, Xiao Bing ^a  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84875167096     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic300976p     Document Type: Article

References (106)

1. Kuran, W. Principle of Coordination Polymerization; John Wiley and Sons Ltd.: New York, 2001; p 275.
2. Baugh, L. S. and Canich, J. A. M. Stereoselective Polymerization with Single-Site Catalysts; Taylor & Francis: New York, 2008; p 447.
3. Wilson, D. Makromol. Chem. Symp. 1993, 66, 273
4. Lauretti, E.; Miani, B.; Misttrali, F. Rubber World 1994, 210, 34
5. Zhao, J.; Ghebremeskel, G. N. Rubber Chem. Technol. 2001, 74, 409
6. Saltman, W. M.; Link, T. H. Ind. Eng. Chem., Prod. Res. Dev. 1964, 3, 199
7. Taube, R.; Sylvester, G. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B.; Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1996; Vol. 1, p 280.
8. Tobisch, S. Acc. Chem. Res. 2002, 35, 96
9. Thiele, S. K.-H.; Wilson, D. R. J. Macromol. Sci., Polym. Rev. 2003, 43, 581
10. Monakov, Yu. B.; Mullagaliev, I. R. Russ. Chem. Bull. Int. Ed. 2004, 53, 1
11. Gibson, V. C.; Spitzmesser, S. K. Chem. Rev. 2003, 103, 283
12. Gibson, V. C.; Redshaw, C.; Solan, G. A. Chem. Rev. 2007, 107, 1745
13. Hou, Z.; Wakatsuki, Y. Coord. Chem. Rev. 2002, 231, 1
14. Zeimentz, P. M.; Arndt, S.; Elvidge, B. R.; Okuda, J. Chem. Rev. 2006, 106, 2404
15. Friebe, L.; Nuyken, O.; Obrecht, W. Adv. Polym. Sci. 2006, 204, 1
16. Fischbach, A.; Anwander, R. Adv. Polym. Sci. 2006, 204, 155
17. Shen, Z. Front. Chem. China 2006, 3, 247
18. Luo, Y.; Nishiura, M.; Hou, Z. J. Organomet. Chem. 2007, 692, 536
19. Nishiura, M.; Hou, Z. Nat. Chem. 2010, 2, 257
20. Li, T.; Jenter, J.; Roesky, P. W. Struct. Bonding (Berlin) 2010, 137, 165
21. Carpentier, J.-F.; Guillaume, S. M.; Kirillov, E.; Sarazin, Y. C. R. Chim. 2010, 13, 608
22. Zhang, Z.; Cui, D.; Wang, B.; Liu, B.; Yang, Y. Struct. Bonding (Berlin) 2010, 137, 49
23. Longiave, C.; Castelli, R. J. Polym. Sci. C 1963, 4, 387
24. Shen, Z.; Gong, C.; Chung, C.; Ouyang, J. Sci. Sin. (Engl. Transl.) 1964, 13, 1339
25. Hsieh, H.; Yeh, H. Rubber Chem. Technol. 1985, 58, 117
26. Shen, Z.; Ouyang, J.; Wang, F.; Hu, Z.; Yu, F.; Qian, B. J. Polym. Sci. Polym. Chem. Ed. 1980, 18, 3345
27. Mazzei, A. Makromol. Chem. 1981, 4 (Suppl) 61
28. Wilson, D.; Jenkins, D. Polym. Bull. 1992, 27, 407
29. Kobayashi, E.; Hayashi, N.; Aoshima, S.; Furukawa, J. J. Polym. Sci., Polym. Chem. 1998, 36, 1707
30. Barbotin, F.; Monteil, V.; Llauro, M.; Boisson, C.; Spitz, R. Macromolecules 2000, 33, 8521
31. Maiwald, S.; Sommer, C.; Müller, G.; Taube, R. Macromol. Chem. Phys. 2001, 202, 1446
32. Friebe, L.; Nuyken, O.; Windisch, H.; Obrecht, W. Macromol. Chem. Phys. 2002, 203, 1055
33. Dong, W.; Masuda, T. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 1838
34. Dong, W.; Endo, K.; Masuda, T. Macromol. Chem. Phys. 2003, 204, 104
35. Dong, W.; Masuda, T. Polymer 2003, 44, 1561
36. Zimmermann, M.; Frøystein, N. Å.; Fischbach, A.; Sirsch, P.; Dietrich, H. M.; Törnroos, K. W.; Herdtweck, E.; Anwander, R. Chem.-Eur. J. 2007, 13, 8784
37. Kaita, S.; Hou, Z.; Wakatsuki, Y. Macromolecules 2001, 34, 1539
38. Boisson, C.; Monteil, V.; Ribour, D.; Spitz, R.; Barbotin, F. Macromol. Chem. Phys. 2003, 204, 1747
39. Kaita, S.; Hou, Z.; Nishiura, M.; Doi, Y.; Kurazumi, J.; Horiuchi, A. C.; Wakatsuki, Y. Macromol. Rapid Commun. 2003, 24, 179
40. Kaita, S.; Doi, Y.; Kaneko, K.; Horiuchi, A. C.; Wakatsuki, Y. Macromolecules 2004, 37, 5860
41. Evans, W. J.; Champagne, T. M.; Ziller, J. W. Chem. Commun. 2005, 5925
42. Evans, W. J.; Champagne, T. M.; Ziller, J. W. Organometallics 2005, 24, 4882
43. Kaita, S.; Yamanaka, M.; Horiuchi, A. C.; Wakatsuki, Y. Macromolecules 2006, 39, 1359
44. Fischbach, A.; Perdih, F.; Sirsch, P.; Scherer, W.; Anwander, R. Organometallics 2002, 21, 4569
45. Fischbach, A.; Klimpel, M.; Widenmeyer, M.; Herdtweck, E.; Scherer, W.; Anwander, R. Angew. Chem., Int. Ed. 2004, 43, 2234
46. Fischbach, A.; Meermann, C.; Eickerling, G.; Scherer, W.; Anwander, R. Macromolecules 2006, 39, 6811
47. Meermann, C.; Törnroos, K.; Nerdal, W.; Anwander, R. Angew. Chem., Int. Ed. 2007, 46, 6508
48. Fischbach, A.; Perdih, F.; Herdtweck, E.; Anwander, R. Organometallics 2006, 25, 1626
49. Arndt, S.; Beckerle, K.; Zeimentz, P. M.; Spaniol, T. P.; Okuda, J. Angew. Chem., Int. Ed. 2005, 44, 7473
50. Robert, D.; Abinet, E.; Spaniol, T. P.; Okuda, J. Chem.-Eur. J. 2009, 15, 11937
51. Bonnet, F.; Violante, C. D. C.; Roussel, P.; Mortreux, A.; Visseaux, M. Chem. Commun. 2009, 3380
52. Jian, Z.; Cui, D.; Hou, Z.; Li, X. Chem. Commun. 2010, 46, 3022
53. Yang, Y.; Liu, B.; Lv, K.; Gao, W.; Cui, D.; Chen, X.; Jing, X. Organometallics 2007, 26, 4575
54. Yang, Y.; Wang, Q.; Cui, D. J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 5251
55. Yang, Y.; Lv, K.; Wang, L.; Wang, Y.; Cui, D. Chem. Commun. 2010, 46, 6150
56. Kaita, S.; Hou, Z.; Wakatsuki, Y. Macromolecules 1999, 32, 9078
57. Gromada, J.; Mortreux, A.; Nowogrocki, G.; Leising, F.; Mathivet, T.; Carpentier, J.-F. Eur. J. Inorg. Chem. 2004, 3247
58. Ajellal, N.; Furlan, L.; Thomas, C. M.; Casagrande, J. O. L.; Carpentier, J.-F. Macromol. Rapid Commun. 2006, 27, 338
59. Tardif, O.; Kaita, S. Dalton Trans. 2008, 2531
60. Wang, L.; Cui, D.; Hou, Z.; Li, W.; Li, Y. Organometallics 2011, 30, 760
61. Zhang, L.; Suzuki, T.; Luo, Y.; Nishiura, M.; Hou, Z. Angew. Chem., Int. Ed. 2007, 46, 1909
62. Gao, W.; Cui, D. J. Am. Chem. Soc. 2008, 130, 4984
63. Lv, K.; Cui, D. Organometallics 2008, 27, 5438
64. Lv, K.; Cui, D. Organometallics 2010, 29, 2987
65. Li, D.; Li, S.; Cui, D.; Zhang, X. Organometallics 2010, 29, 2186
66. Bolm, C.; Weickhardt, K.; Zehnder, M.; Ranff, T. Chem. Ber. 1991, 124, 1173
67. Nishiyama, H. Chem. Soc. Rev. 2007, 36, 1133
68. Takemoto, T.; Iwasa, S.; Hiroshi, H.; Shibatomi, K.; Kameyama, M.; Motoyamac, Y.; Nishiyama, H. Tetrahedron Lett. 2007, 48, 3397
69. Nishiyama, H.; Ishikawa, J.; Shiomi, T. Tetrahedron Lett. 2007, 48, 7841
70. Hashimoto, T.; Shiomi, T.; Ito, J.; Nishiyama, H. Tetrahedron 2007, 63, 12883
71. Satake, Y.; Abe, S.; Okazaki, S.; Ban, N.; Hikage, T.; Ueno, T.; Nakajima, H.; Suzuki, A.; Yamane, T.; Nishiyama, H.; Watanabe, Y. Organometallics 2007, 26, 4904
72. Ito, J.; Kitase, M.; Nishiyama, H. Organometallics 2007, 26, 6412
73. Shiomi, T.; Nishiyama, H. Org. Lett. 2007, 9, 1651
74. Inoue, H.; Kikuchi, M.; Ito, J.; Nishiyama, H. Tetrahedron 2008, 64, 493
75. Ito, J.; Miyakawa, T.; Nishiyama, H. Organometallics 2008, 27, 3312
76. Bugarin, A.; Connell, B. T. Organometallics 2008, 27, 4357
77. Kimura, T.; Uozumi, Y. Organometallics 2008, 27, 5159
78. Ito, J.; Ujiie, S.; Nishiyama, H. Organometallics 2009, 28, 630
79. Shiomi, T.; Adachi, T.; Ito, J.; Nishiyama, H. Org. Lett. 2009, 11, 1011
80. Nishiyama, H.; Ito, J. Chem. Commun. 2010, 46, 203
81. Yang, Y.; Shi, T.; Zhang, X.; Tang, Z.; Wen, Z.; Quan, J.; Wu, Y. Org. Biomol. Chem. 2011, 9, 5845
82. Chuchuryukin, A. V.; Huang, R.; Lutz, M.; Chadwick, J. C.; Spek, A. L.; van Koten, G. Organometallics 2011, 30, 2819
83. Ward, B. D.; Bellemin-Laponnaz, S.; Gade, L. H. Angew. Chem., Int. Ed. 2005, 44, 1668
84. Lukešová, L.; Ward, B. D.; Bellemin-Laponnaz, S.; Wadepohla, H.; Gade, L. H. Dalton Trans. 2007, 920
85. Lukešová, L.; Ward, B. D.; Bellemin-Laponnaz, S.; Wadepohl, H.; Gade, L. H. Organometallics 2007, 26, 4652
86. Zou, J.; Berg, D. J.; Stuart, D.; McDonald, R.; Twamley, B. Organometallics 2011, 30, 4958
87. Motoyama, Y.; Okano, M.; Narusawa, H.; Makihara, N.; Aoki, K.; Nishiyama, H. Organometallics 2001, 20, 1580
88. Stol, M.; Snelders, D. J. M.; de Pater, J. J. M.; van Klink, G. P. M.; Kooijman, H.; Spek, A. L.; van Koten, G. Organometallics 2005, 24, 743
89. Stol, M.; Snelders, D. J. M.; Godbole, M. D.; Havenith, R. W. A.; Haddleton, D.; Clarkson, G.; Lutz, M.; Spek, A. L.; van Klink, G. P. M.; van Koten, G. Organometallics 2007, 26, 3985
90. 3+ for coordination number 8 (CN = 8), see: Dean, J. A. Lange's handbook of chemistry, 15 th ed.; McGraw-Hill: New York, 1999; Section 4: 4.5.
91. Wang, D.; Cui, D.; Miao, W.; Li, S.; Huang, B. Dalton Trans. 2007, 4576
92. For other homoleptic rare-earth-metal complexes, see: Zimmermann, M.; Anwander, R. Chem. Rev. 2010, 110, 6194
93. For the chloride effects in isoprene polymerization, see: Evans, W. J.; Giarikos, D. G. Macromolecules 2004, 37, 5130
94. Pross, A.; Marquardt, P.; Reichert, K.-H.; Nentwig, W.; Knauf, T. Angew. Makromol. Chem. 1993, 211, 89
95. Oehme, A.; Gebauer, U.; Gehrke, K.; Lechner, M. D. Angew. Makromol. Chem. 1996, 235, 121
96. Porri, L.; Ricci, G.; Shubin, N. Macromol. Symp. 1998, 128, 53
97. Koboyashi, E.; Hayashi, N.; Aoshima, S.; Furukaya, J. J. Polym. Sci., Polym. Chem. 1998, 36, 1707
98. Iovu, H.; Hubca, G.; Racoti, D.; Hurst, J. S. Eur. Polym. J. 1999, 35, 335
99. Boisson, C.; Barbotin, F.; Spitz, R. Macromol. Chem. Phys. 1999, 200, 1163
100. Quirk, R.; Kells, A.; Yunlu, K. M.; Cuif, J.-P. Polymer 2000, 41, 5903
101. Evans, W. J.; Giarikos, D. G.; Ziller, J. W. Organometallics 2001, 20, 5751
102. Kwag, G.; Lee, H.; Kim, S. Macromolecules 2001, 34, 5367
103. Baugh, L. S.; Canich, J. A. M. Stereoselective Polymerization with Single-Site Catalysts; Taylor & Francis: New York, 2008; p 462.
104. Li, X.; Nishiura, M.; Hu, L.; Mori, K.; Hou, Z. J. Am. Chem. Soc. 2009, 131, 13870
105. SHELXTL; PC Siemens Analytical X-ray Instruments: Madison, WI, 1993.
106. Sheldrick, G. M. SHELXTL Structure Determination Programs, version 5.0, PC; Siemens Analytical Systems: Madison, WI, 1994.