Isoprene polymerization with yttrium amidinate catalysts: Switching the regio- and stereoselectivity by addition of AlMe

Angewandte Chemie - International Edition

Volumn 47, Issue 14, 2008, Pages 2642-2645

  Zhang, Lixin ^a   Nishiura, Masayoshi ^a   Yuki, Masahiro ^a   Luo, Yi ^a   Hou, Zhaomin ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

Aluminum; Homogeneous catalysis; N ligands; Polymerization; Yttrium

Indexed keywords

ABS RESINS; ALUMINA; CHEMICAL REACTIONS; MONOMERS; POLYMERS; STEREOSELECTIVITY; YTTRIUM;

ALUMINUM; HOMOGENEOUS CATALYSIS; N LIGANDS; POLYMERIZATION;

CATALYSIS;

EID: 47549108775     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705120     Document Type: Article

References (57)

1. Selected reviews: a) Z. Hou, Y. Wakatsuki, Coord. Chem. Rev. 2002, 231, 1-22;
2. b) W. E. Piers, D. J. H. Emslie, Coord. Chem. Rev. 2002, 233, 131-155;
3. c) F. T. Edelmann, D. M. M. Freckmann, H. Schumann, Chem. Rev. 2002, 102, 1851-1896;
4. d) J. Gromada, J. F. Carpentier, A. Mortreux, Coord. Chem. Rev. 2004, 248, 397-410;
5. e) Y. Nakayama, H. Yasuda, J. Organomet. Chem. 2004, 689, 4489-4498;
6. f) P. M. Zeimentz, S. Arndt, B. R. Elvidge, J. Okuda, Chem. Rev. 2006, 106, 2404-2433.
7. a) K. B. Aubrecht, K. Chang, M. A. Hillmyer, W. B. Tolman, J. Polym. Sci. Part A: Polym. Chem. 2001, 39, 284-293;
8. b) Y. Luo, Y. Yao, Q. Shen, J. Sun, L. Weng, J. Organomet. Chem. 2002, 662, 144-149;
9. c) Y. Luo, Y. Yao, Q. Shen, K. Yu, L. Weng, Eur. J. Inorg. Chem. 2003, 318-323;
10. d) S. Bambirra, D. van Leusen, A. Meetsman, B. Hessen, J. H. Teuben, Chem. Commun. 2003, 522-523;
11. e) S. Bambirra, M. Bouwkamp, A. Meetsman, B. Hessen, J. Am. Chem. Soc. 2004, 126, 9182-9183;
12. f) C. Villiers, P. Thuery, M. Ephritikhine, Eur. J. Inorg. Chem. 2004, 4624-4632;
13. g) A. A. Trifonov, E. A. Fedorova, G. K. Fukin, M. N. Bochkarev, Eur. J. Inorg. Chem. 2004, 4396-4401;
14. h) M. L. Cole, P. C. Junk, Chem. Commun. 2005, 2695-2697;
15. i) S. Bambirra, A. Meetsma, B. Hessen, Organometallics 2006, 25, 3454-3462;
16. j) S. Bambirra, H. Tsurugi, D. van Leusen, B. Hessen, Dalton Trans. 2006, 1157-1161;
17. k) A. A. Trifonov, G. G. Skvortsov, D. M. Lyubov, N. A. Skorodumova, G. K. Fukin, E. V. Baranov, V. N. Glushakova, Chem. Eur. J. 2006, 12, 5320-5327;
18. l) C. Li, Y. Wang, L. Zhou, H. Sun, Q. Shen, J. Appl. Polym. Sci. 2006, 102, 22-28.
19. For a review, see: Z. Hou, Y. Luo, X. Li, J. Organomet. Chem. 2006, 691, 3114-3121.
20. a) Y. Luo, J. Baldamus, Z. Hou, J. Am. Chem. Soc. 2004, 126, 13910-13911;
21. b) X. Li, J. Baldamus, Z. Hou, Angew. Chem. 2005, 117, 984-987;
22. Angew. Chem. Int. Ed. 2005, 44, 962-965;
23. c) X. Li, Z. Hou, Macromolecules 2005, 38, 6767-6769;
24. d) L. Zhang, Y. Luo, Z. Hou, J. Am. Chem. Soc. 2005, 127, 14562-14563;
25. e) X. Li, J. Baldamus, M. Nishiura, O. Tardif, Z. Hou, Angew. Chem. 2006, 118, 8364-8368;
26. Angew. Chem. Int. Ed. 2006, 45, 8184-8188;
27. f) L. Zhang, T. Suzuki, Y. Luo, M. Nishiura, Z. Hou, Angew. Chem. 2007, 119, 1941-1945;
28. Angew. Chem. Int. Ed. 2007, 46, 1909-1913;
29. g) Y. Luo, M. Nishiura, Z. Hou, J. Organomet. Chem. 2007, 692, 536-544;
30. h) X. Li, M. Nishiura, K. Mori, T. Mashiko, Z. Hou, Chem. Commun. 2007, 4137-4139.
31. For examples, see: a) Z. Shen, J. Ouyang in Handbook on the Physics and Chemistry of Rare Earths (Eds.: K. A. Gschneidner, Jr., L. Fleming), Elsevier Science Publishers, Dordrecht, 1987, chap. 61;
32. b) L. Porri, A. Giarrusso in Comprehensive Polymer Science, Vol. 4 (Eds.: G. C. Eastmond, A. Ledwith, S. Russo, P. Sigwalt), Pergamon, Oxford, 1989, pp. 53-108;
33. c) R. Taube, G. Sylvester in Applied Homogeneous Catalysis with Organometallic Compounds, Vol. 1 (Eds.: B. Cornils, W. A. Herrmann), Wiley-VCH, Weinheim, 1996, pp. 280-318;
34. d) S. Kaita, Y. Doi, K. Kaneko, A. C. Horiuchi, Y. Wakatsuki, Macromolecules 2004, 37, 5860-5862;
35. e) S. Arndt, K. Beckerle, P. M. Zeimentz, T. P. Spaniol, J. Okuda, Angew. Chem. 2005, 117, 7640-7644;
36. Angew. Chem. Int. Ed. 2005, 44, 7473-7477;
37. f) W. J. Evans, T. M. Champagne, D. G. Giarikos, J. W. Ziller, Organometallics 2005, 24, 570-579;
38. g)W. J. Evans, T. M. Champagne, D. G. Giarikos, J. W. Ziller, Chem. Commun. 2005, 5925-5927;
39. h) A. Fischbach, C. Meermann, G. Eickerling, W. Scherer, R. Anwander, Macromolecules 2006, 39, 6811-6816;
40. i) A. Fischbach, F. Perdih, E. Herdtweck, R. Anwander, Organometallics 2006, 25, 1626-1642;
41. j) N. Ajellal, L. Furlan, C. M. Thomas, O. L. Casagrande, Jr., J. F. Carpentier, Macromol. Rapid Commun. 2006, 27, 338-343;
42. k) C. Meermann, K. W. Törnroos, W. Nerdal, R. Anwander, Angew. Chem. 2007, 119, 6628-6633;
43. Angew. Chem. Int. Ed. 2007, 46, 6508-6513;
44. l) M. Zimmermann, N. Å. Frøystein, A. Fischbach, P. Sirsch, H. M. Dietrich, K. W. Törnroos, E. Herdtweck, R. Anwander, Chem. Eur. J. 2007, 13, 8784-8800;
45. m) Y. Yang, B. Liu, K. Lv, W. Gao, D. Cui, X. Chen, X. Jing, Organometallics 2007, 26, 4575-4584.
46. [5j] A similar reaction was also observed for butadiene polymerization: R. Taube, H. Windisch, S. Maiwald, H. Hemling, H. Schumann, J. Organomet. Chem. 1996, 513, 49-61.
47. S. Harder, Organometallics 2005, 24, 373-379.
48. S. Ogata, A. Mochizuki, M.-A. Kakimoto, Y. Imai, Bull. Chem. Soc. Jpn. 1986, 59, 2171-2177.
49. CCDC-657217 (1) and CCDC-657218 (2) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
50. 2(thf)] instead of 1 gave a similar result in terms of selectivity but with a lower activity. The polymerization in toluene also showed a similar selectivity, although the activity was somewhat lower than that in chlorobenzene because of lower solubility.
51. 3 was added, probably a result of chain transfer to the aluminum atom.
52. 3 have little effect on the polymerization selectivity.
53. For similar complexes, see: a) R. Anwander, M. G. Klimpel, H. M. Dietrich, D. J. Shorokhov, W. Scherer, Chem. Commun. 2003, 1008-009;
54. b) H. M. Dietrich, C. Zapilko, E. Herdtweck, R. Anwander, Organometallics 2005, 24, 5767-5771.
55. 2). The THF-free analogue is unstable.
56. Computational studies suggest that only the 3,4-coordination of isoprene to the metal center in 1a is permitted as the 1,4-coordination mode (either cis or trans) is not accessible. See the Supporting Information for details.
57. 3 have not yet been successful because of its instability.