Observation of intramolecular C-H⋯F-C contacts in non-metallocene polyolefin catalysts: Model for weak attractive interactions between polymer chain and noninnocent ligand

Angewandte Chemie - International Edition

Volumn 42, Issue 14, 2003, Pages 1628-1632

  Kui, Steven C F ^a   Zhu, Nianyong ^a   Chan, Michael C W ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

Fluorine; Hydrogen bonds; Polymerization; Through space interactions; Zirconium

Indexed keywords

ALKYLATION; CATALYSTS; HYDROGEN BONDS; POLYMERIZATION;

INTRAMOLECULAR CONTACTS;

POLYOLEFINS;

FLUORINE; LIGAND; METAL DERIVATIVE; POLYMER; POLYOLEFIN; ZIRCONIUM;

ARTICLE; CATALYST; HYDROGEN BOND; LIGAND BINDING; MOLECULAR INTERACTION; POLYMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0037432907     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200219832     Document Type: Article

References (32)

1. a) H. H. Brintzinger, D. Fischer, R. Mülhaupt, B. Rieger, R. M. Waymouth, Angew. Chem. 1995, 107, 1255-1283; Angew. Chem. Int. Ed. Engl. 1995, 34, 1143-1170;
2. a) H. H. Brintzinger, D. Fischer, R. Mülhaupt, B. Rieger, R. M. Waymouth, Angew. Chem. 1995, 107,1255-1283; Angew. Chem. Int. Ed. Engl. 1995, 34, 1143-1170;
3. b) L. Resconi, L. Cavallo, A. Fait, F. Piemontes, Chem. Rev. 2000, 100, 1253-1345.
4. a) A. Bader, E. Lindner, Coord. Chem. Rev. 1991, 108, 27-110;
5. b) C. S. Slone, D. A. Weinberger, C. A. Mirkin, Prog. Inorg. Chem. 1999, 48, 233-350.
6. a) J. Ruwwe, G. Erker, R. Fröhlich, Angew. Chem. 1996, 108, 108-110; Angew. Chem. Int. Ed. Engl. 1996, 35, 80-82; b) Y. Sun, R. E. von H. Spence, W. E. Piers, M. Parvez, G. P. A. Yap, J. Am. Chem. Soc. 1997, 119, 5132-5143; c) U. Siemeling, Chem. Rev. 2000, 100, 1495-1526; for agostic interactions between metal and polymer chain, see: d) W. E. Piers, J. E. Bercaw, J. Am. Chem. Soc. 1990, 112, 9406-9407; e) M. Brookhart, M. L. H. Green, L. L. Wong, Prog. Inorg. Chem. 1998, 36, 124.
7. a) J. Ruwwe, G. Erker, R. Fröhlich, Angew. Chem. 1996, 108, 108-110; Angew. Chem. Int. Ed. Engl. 1996, 35, 80-82; b) Y. Sun, R. E. von H. Spence, W. E. Piers, M. Parvez, G. P. A. Yap, J. Am. Chem. Soc. 1997, 119, 5132-5143; c) U. Siemeling, Chem. Rev. 2000, 100, 1495-1526; for agostic interactions between metal and polymer chain, see: d) W. E. Piers, J. E. Bercaw, J. Am. Chem. Soc. 1990, 112, 9406-9407; e) M. Brookhart, M. L. H. Green, L. L. Wong, Prog. Inorg. Chem. 1998, 36, 124.
8. a) J. Ruwwe, G. Erker, R. Fröhlich, Angew. Chem. 1996, 108, 108-110; Angew. Chem. Int. Ed. Engl. 1996, 35, 80-82; b) Y. Sun, R. E. von H. Spence, W. E. Piers, M. Parvez, G. P. A. Yap, J. Am. Chem. Soc. 1997, 119, 5132-5143; c) U. Siemeling, Chem. Rev. 2000, 100, 1495-1526; for agostic interactions between metal and polymer chain, see: d) W. E. Piers, J. E. Bercaw, J. Am. Chem. Soc. 1990, 112, 9406-9407; e) M. Brookhart, M. L. H. Green, L. L. Wong, Prog. Inorg. Chem. 1998, 36, 124.
9. a) J. Ruwwe, G. Erker, R. Fröhlich, Angew. Chem. 1996, 108, 108-110; Angew. Chem. Int. Ed. Engl. 1996, 35, 80-82; b) Y. Sun, R. E. von H. Spence, W. E. Piers, M. Parvez, G. P. A. Yap, J. Am. Chem. Soc. 1997, 119, 5132-5143; c) U. Siemeling, Chem. Rev. 2000, 100, 1495-1526; for agostic interactions between metal and polymer chain, see: d) W. E. Piers, J. E. Bercaw, J. Am. Chem. Soc. 1990, 112, 9406-9407; e) M. Brookhart, M. L. H. Green, L. L. Wong, Prog. Inorg. Chem. 1998, 36, 124.
10. a) J. Ruwwe, G. Erker, R. Fröhlich, Angew. Chem. 1996, 108, 108-110; Angew. Chem. Int. Ed. Engl. 1996, 35, 80-82; b) Y. Sun, R. E. von H. Spence, W. E. Piers, M. Parvez, G. P. A. Yap, J. Am. Chem. Soc. 1997, 119, 5132-5143; c) U. Siemeling, Chem. Rev. 2000, 100, 1495-1526; for agostic interactions between metal and polymer chain, see: d) W. E. Piers, J. E. Bercaw, J. Am. Chem. Soc. 1990, 112, 9406-9407; e) M. Brookhart, M. L. H. Green, L. L. Wong, Prog. Inorg. Chem. 1998, 36, 124.
11. a) J. Ruwwe, G. Erker, R. Fröhlich, Angew. Chem. 1996, 108, 108-110; Angew. Chem. Int. Ed. Engl. 1996, 35, 80-82; b) Y. Sun, R. E. von H. Spence, W. E. Piers, M. Parvez, G. P. A. Yap, J. Am. Chem. Soc. 1997, 119, 5132-5143; c) U. Siemeling, Chem. Rev. 2000, 100, 1495-1526; for agostic interactions between metal and polymer chain, see: d) W. E. Piers, J. E. Bercaw, J. Am. Chem. Soc. 1990, 112, 9406-9407; e) M. Brookhart, M. L. H. Green, L. L. Wong, Prog. Inorg. Chem. 1998, 36, 124.
12. Related examples of weak Zr⋯F interactions: a) A. R. Siedle, R. A. Newmark, W. M. Lamanna, J. C. Huffman, Organometallics 1993, 12, 1491-1492; b) X. Yang, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1994, 116, 10015-10031; c) J. Karl, G. Erker, R. Fröhlich, J. Am. Chem. Soc. 1997, 119, 11165-11173; d) L. H. Gade, Chem. Commun. 2000, 173-181.
13. Related examples of weak Zr⋯F interactions: a) A. R. Siedle, R. A. Newmark, W. M. Lamanna, J. C. Huffman, Organometallics 1993, 12, 1491-1492; b) X. Yang, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1994, 116, 10015-10031; c) J. Karl, G. Erker, R. Fröhlich, J. Am. Chem. Soc. 1997, 119, 11165-11173; d) L. H. Gade, Chem. Commun. 2000, 173-181.
14. Related examples of weak Zr⋯F interactions: a) A. R. Siedle, R. A. Newmark, W. M. Lamanna, J. C. Huffman, Organometallics 1993, 12, 1491-1492; b) X. Yang, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1994, 116, 10015-10031; c) J. Karl, G. Erker, R. Fröhlich, J. Am. Chem. Soc. 1997, 119, 11165-11173; d) L. H. Gade, Chem. Commun. 2000, 173-181.
15. Related examples of weak Zr⋯F interactions: a) A. R. Siedle, R. A. Newmark, W. M. Lamanna, J. C. Huffman, Organometallics 1993, 12, 1491-1492; b) X. Yang, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1994, 116, 10015-10031; c) J. Karl, G. Erker, R. Fröhlich, J. Am. Chem. Soc. 1997, 119, 11165-11173; d) L. H. Gade, Chem. Commun. 2000, 173-181.
16. a) J. Saito, M. Mitani, J. Mohri, Y. Yoshida, S. Matsui, S. Ishii, S. Kojoh, N. Kashiwa, T. Fujita, Angew. Chem. 2001, 113, 3002-3004; Angew. Chem. Int. Ed. 2001, 40, 2918-2920;
17. a) J. Saito, M. Mitani, J. Mohri, Y. Yoshida, S. Matsui, S. Ishii, S. Kojoh, N. Kashiwa, T. Fujita, Angew. Chem. 2001, 113, 3002-3004; Angew. Chem. Int. Ed. 2001, 40, 2918-2920;
18. b) M. Mitani, J. Mohri, Y. Yoshida, J. Saito, S. Ishii, K. Tsuru, S. Matsui, R. Furuyama, T. Nakano, H. Tanaka, S. Kojoh, T. Matsugi, N. Kashiwa, T. Fujita, J. Am. Chem. Soc. 2002, 124, 3327-3336;
19. c) S. Ishii, J. Saito, M. Mitani, J. Mohri, N. Matsukawa, Y. Tohi, S. Matsui, N. Kashiwa, T. Fujita, J. Mol. Catal. A 2002, 179, 11-16.
20. a) M. Mitani, R. Furuyama, J. Mohri, J. Saito, S. Ishii, H. Terao, N. Kashiwa, T. Fujita, J. Am. Chem. Soc. 2002, 124, 7888-7889;
21. b) J. Saito, M. Mitani, M. Onda, J. Mohri, S. Ishii, Y. Toshida, T Nakano, H. Tanaka, T. Matsugi, S. Kojoh, N. Kashiwa, T. Fujita, Macromol. Rapid Commun. 2001, 22, 1071-1075.
22. a) J. Tian, P. D. Hustad, G. W. Coates, J. Am. Chem. Soc. 2001, 123, 5134-5135;
23. b) P. D. Hustad, J. Tian, G. W. Coates, J. Am. Chem. Soc. 2002, 124, 3614-3621.
24. a) G. R. Desiraju, Acc. Chem. Res. 2002, 35, 565-573;
25. b) J. Parsch, J. W. Engels, J. Am. Chem. Soc. 2002, 124, 5664-5672;
26. c) W. Caminati, S. Melandri, P. Moreschini, P. G. Favero, Angew. Chem. 1999, 111, 3105-3107; Angew. Chem. Int Ed. 1999, 38, 2924-2925.
27. c) W. Caminati, S. Melandri, P. Moreschini, P. G. Favero, Angew. Chem. 1999, 111, 3105-3107; Angew. Chem. Int Ed. 1999, 38, 2924-2925.
28. M. Bochmann, S. J. Lancaster, Organometallics 1993, 12, 633-640.
29. 19F coupling eliminates the possibility of the involvement of Zr⋯F interactions (and more generally of the coupling occurring "through-bond" through the methylene carbon atom).
30. -3. CCDC-190342 (1) and CCDC-190343 (2) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk).
31. E. Y. Tshuva, I. Goldberg, M. Kol, Z. Goldschmidt, Organometallics 2001, 20, 3017-3028.
32. 3 groups (see ref. [5c]). We thank the reviewers for helpful comments, and we are indebted to Dr. Wa-Hung Leung (HKUST) for assistance in variable-temperature NMR experiments.