"Constrained geometry" dialkyl catalysts. Efficient syntheses, C-H bond activation chemistry, monomer-dimer equilibration, and α-olefin polymerization catalysis

Organometallics

Volumn 16, Issue 16, 1997, Pages 3649-3657

  Chen, You Xian ^a   Marks, Tobin J ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000130320     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970288+     Document Type: Article

References (75)

1. (a) Woo, T. K.; Margl, P. M.; Lohrenz, J. C. W.; Blochl, P. E.; Ziegler, T. J. Am. Chem. Soc. 1996, 118, 13021-13030.
2. (b) Chen, Y.-X.; Stern, C. L.; Yang, S.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 12451-12452.
3. (c) Stevens, J. C. In Studies in Surface Science and Catalysis; Hightower, J. W., Delglass, W. N., Iglesia, E., Bell, A. T., Eds.; Elsevier: Amsterdam, 1996; Vol. 101, pp 11-20 and references therein.
4. (d) Canich, J. M.; Hlatky, G. G.; Turner, H. W. PCT Appl. WO 92-00333, 1992. Canich, J. M. Eur. Patent Appl. EP 420 436-A1, 1991 (Exxon Chemical Co.).
5. (e) Stevens, J. C.; Timmers, F. J.; Wilson, D. R.; Schmidt, G. F.; Nickias, P. N.; Rosen, R. K.; Knight, G. W.; Lai, S. Eur. Patent Appl. EP 416 815-A2, 1991 (Dow Chemical Co.).
6. For recent reviews, see: (a) Kaminsky, W.; Arndt, M. Adv. Polym. Sci. 1997, 127, 144-187. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255-270. (c) Brintzinger, H.-H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143-1170. (d) Catalyst Design for Tailor-Made Polyolefins; Soga, K,; Terano, M., Eds.; Elsevier: Tokyo, 1994. (e) Möhring, P. C.; Coville, N. J. J. Organomet. Chem. 1994, 479, 1-29. (f) Marks, T. J. Acc. Chem. Res. 1992, 25, 57-65. (g) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325-387.
7. For recent reviews, see: (a) Kaminsky, W.; Arndt, M. Adv. Polym. Sci. 1997, 127, 144-187. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255-270. (c) Brintzinger, H.-H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143-1170. (d) Catalyst Design for Tailor-Made Polyolefins; Soga, K,; Terano, M., Eds.; Elsevier: Tokyo, 1994. (e) Möhring, P. C.; Coville, N. J. J. Organomet. Chem. 1994, 479, 1-29. (f) Marks, T. J. Acc. Chem. Res. 1992, 25, 57-65. (g) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325-387.
8. For recent reviews, see: (a) Kaminsky, W.; Arndt, M. Adv. Polym. Sci. 1997, 127, 144-187. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255-270. (c) Brintzinger, H.-H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143-1170. (d) Catalyst Design for Tailor-Made Polyolefins; Soga, K,; Terano, M., Eds.; Elsevier: Tokyo, 1994. (e) Möhring, P. C.; Coville, N. J. J. Organomet. Chem. 1994, 479, 1-29. (f) Marks, T. J. Acc. Chem. Res. 1992, 25, 57-65. (g) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325-387.
9. For recent reviews, see: (a) Kaminsky, W.; Arndt, M. Adv. Polym. Sci. 1997, 127, 144-187. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255-270. (c) Brintzinger, H.-H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143-1170. (d) Catalyst Design for Tailor-Made Polyolefins; Soga, K,; Terano, M., Eds.; Elsevier: Tokyo, 1994. (e) Möhring, P. C.; Coville, N. J. J. Organomet. Chem. 1994, 479, 1-29. (f) Marks, T. J. Acc. Chem. Res. 1992, 25, 57-65. (g) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325-387.
10. For recent reviews, see: (a) Kaminsky, W.; Arndt, M. Adv. Polym. Sci. 1997, 127, 144-187. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255-270. (c) Brintzinger, H.-H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143-1170. (d) Catalyst Design for Tailor-Made Polyolefins; Soga, K,; Terano, M., Eds.; Elsevier: Tokyo, 1994. (e) Möhring, P. C.; Coville, N. J. J. Organomet. Chem. 1994, 479, 1-29. (f) Marks, T. J. Acc. Chem. Res. 1992, 25, 57-65. (g) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325-387.
11. For recent reviews, see: (a) Kaminsky, W.; Arndt, M. Adv. Polym. Sci. 1997, 127, 144-187. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255-270. (c) Brintzinger, H.-H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143-1170. (d) Catalyst Design for Tailor-Made Polyolefins; Soga, K,; Terano, M., Eds.; Elsevier: Tokyo, 1994. (e) Möhring, P. C.; Coville, N. J. J. Organomet. Chem. 1994, 479, 1-29. (f) Marks, T. J. Acc. Chem. Res. 1992, 25, 57-65. (g) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325-387.
12. For recent reviews, see: (a) Kaminsky, W.; Arndt, M. Adv. Polym. Sci. 1997, 127, 144-187. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255-270. (c) Brintzinger, H.-H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143-1170. (d) Catalyst Design for Tailor-Made Polyolefins; Soga, K,; Terano, M., Eds.; Elsevier: Tokyo, 1994. (e) Möhring, P. C.; Coville, N. J. J. Organomet. Chem. 1994, 479, 1-29. (f) Marks, T. J. Acc. Chem. Res. 1992, 25, 57-65. (g) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325-387.
13. (a) Shapiro, P. J.; Cotter, W. D.; Schaefer, W. P.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1994, 116, 4623.
14. (b) Piers, W. E.; Shapiro, P. J.; Bunnel, E. E.; Bercaw, J. E. Synlett 1990, 2, 74.
15. (c) Shapiro, P. J.; Bunel, E. E.; Schaefer, W. P.; Bercaw, J. E. Organometallics 1990, 9, 867.
16. Fu, P.-F.; Wilson, D. J.; Rudolph, P. R.; Stern, C. L.; Marks, T. J. Submitted for publication.
17. Chandra, G.; Lappert, M. F. J. Chem. Soc. A 1968, 1940.
18. Hughes, A. K.; Meetsma, A.; Teuben, J. H. Organometallics 1993, 12, 1936-1945.
19. (a) Herrmann, W. A.; Morawietz, M. J. A. J. Organomet. Chem. 1994, 482, 169-181.
20. (b) Herrmann, W. A.; Morawietz, M. J. A.; Priermeier, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 1946.
21. Gauthier, W. J.; Corrigan, J. F.; Taylor, N. J.; Collins, S. Macromolecules 1995, 28, 377.
22. (a) Diamond, G. M.; Jordan, R. F.; Petersen, J. L. J. Am. Chem. Soc. 1996, 118, 8024-8033.
23. (b) Diamond, G. M.; Jordan, R. F.; Petersen, J. L. Organometallics 1996, 15, 4030-4037, 4038-4044, 4045-4053.
24. (c) Diamond, G. M.; Rodewald, S.; Jordan, R. F. Organometallics 1995, 14, 5-7.
25. Carpenetti, D. W.; Kloppenburg, L.; Kupec, J. T.; Petersen, J. L. Organometallics 1996, 15, 1572-1581.
26. Kim, Il.; Jordan, R. F. Macromolecules 1996, 29, 489-491.
27. (a) Wu, Z.; Jordan, R. F.; Petersen, J. L. J. Am. Chem. Soc. 1995, 117, 5867-5868.
28. (b) Pellecchia, C.; Pappalardo, D.; Oliva, L.; Zambelli, A. J. Am. Chem. Soc. 1995, 117, 6593-6594.
29. (c) Temme, B.; Erker, G.; Karl, J.; Luftmann, H.; Fröhlich, R.; Kotila, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1755-1757.
30. (d) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015-10031.
31. (e) Bochmann, M.; Lancaster, S. J.; Hursthouse, M. B.; Malik, K. M. A. Organometallics 1994, 13, 2235-2243.
32. (f) Gillis, D. J.; Tudoret, M.-J.; Baird, M. C. J. Am. Chem. Soc. 1993, 115, 2543-2545.
33. (g) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1991, 113, 3623-3625.
34. (h) Ewen, J. A.; Elder, M. J. Chem. Abstr. 1991, 115, 136998g.
35. (a) Chien, J. C. W.; Tsai, W.-M.; Rausch, M. D. J. Am. Chem. Soc. 1991, 113, 8570-8571.
36. (b) Yang, X.; Stern, C. L.; Marks, T. J. Organometallics 1991, 10, 840-842.
37. (c) Ewen, J. A.; Elder, M. J. Eur. Pat. Appl. 426637, 1991; Chem. Abstr. 1991, 115, 136987e, 136988d.
38. (d) Hlatky, G. G.; Upton, D. J.; Turner, H. W. U.S. Pat. Appl. 459921, 1990; Chem. Abstr. 1991, 115, 256897v.
39. (a) Kaminsky, W.; Kulper, K.; Brintzinger, H. H. Angew. Chem., Int. Ed. Engl. 1985, 24, 507-509.
40. (b) Sinn, H.; Kaminsky, W. Adv. Organomet. Chem. 1980, 18, 99-149.
41. (a) Jia, L.; Yang, X.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 842-857.
42. (b) Deck, P. A.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 6128-6129.
43. (c) Giardello, M. A.; Eisen, M. S.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 12114-12129.
44. (d) Jia, L.; Yang, X.; Ishihara, A.; Marks, T. J. Organometallics 1995, 14, 3135-3137.
45. (e) Chien, J. C. W.; Song, W.; Rausch, M. D. J. Polym. Sci., Part A: Polym. Chem. 1994, 32, 2387-2393.
46. (f) Eisch, J.; Pombrik, S. I.; Zheng, G.-X. Organometallics 1993,12, 3856-3863.
47. (g) Siedle, A. R.; Lamanna, W. M.; Newmark, R. A.; Stevens, J.; Richardson, D. E.; Ryan, M. Makromol. Chem., Macromol. Symp. 1993, 66, 215-224.
48. (a) After this study was completed, we became aware of a European patent application briefly describing a variant of this reaction, see: Nickias, P. N.; Devore, D. D.; Wilson, D. R. PCT Appl. WO 08199, 1993. We thank Dr. D. D. Devore of Dow Chemical Co. for bringing this to our attention.
49. (b) The use of alkane elimination in the one-step synthesis of organoscandium complexes containing a multidentate Cp ligand has been recently reported, see: Mu, Y.; Piers, W. E.; MacQuarrie, D. C.; Zaworotko, M. J.; Young, V. G., Jr. Organo-metallics 1996, 75, 2720-2726.
50. (c) For the synthesis of bis(phenolate) dibenzyls of Ti and Zr, see: van der Linden, A.; Schaverien, C. J.; Meijboom, N.; Ganter, C.; Orpen, A. G. J. Am. Chem. Soc. 1995, 117, 3008-3021.
51. Fachinetti, G.; Fochi, G.; Floriani, C. J. Chem. Soc., Dalton Trans. 1977, 1946-1950.
52. Zucchini, U.; Albizzati, E.; Giannini, U. J. Organomet. Chem. 1971, 26, 357-372.
53. Massey, A. G.; Park, A. J. J. Organomet. Chem. 1964, 2, 245-250.
54. (a) Bochmann, M.; Lancaster, S. J. Organometallics 1993, 12, 633-640.
55. (b) Jordan, R. F.; LaPointe, R. E.; Baenziger, N. C.; Hinch, G. D. Organometallics 1990, 9, 1539.
56. (c) Jordan, R. F.; LaPointe, R. E.; Bajgur, C. S.; Echols, S. F.; Willet, R. J. Am. Chem. Soc. 1987, 109, 4111.
57. (d) Latesky, S. L.; McMullen, A. K.; Niccolai, G. P.; Rothwell, I. P.; Huffman, J. C. Organometallics 1985, 4, 902.
58. (e) Mintz, E. A.; Moloy, K. G.; Marks, T. J. J. Am. Chem. Soc. 1982, 104, 4692.
59. (f) Davis, G. R.; Jarvis, J. A.; Kilburn, B. T. J. Chem. Soc., Chem. Commun. 1971, 15111.
60. (a) Kreuden, C.; Jordan, R. F.; Zhang, H. Organometallics 1995, 14, 2993.
61. (b) Sinnema, P. J.; Meetsma, A.; Teuben, J. H. Organometallics 1993, 12, 184.
62. (c) Luinstra, G. A.; Teuben, J. H. J. Am. Chem. Soc. 1992, 114, 3361.
63. (d) Vondrak, T.; Mach, K.; Varga, V.; Terpstra, A. J. Organomet. Chem. 1992, 425, 27.
64. (e) Schock, L. E.; Brock, C. P.; Marks, T. J. Organometallics 1987, 6, 232.
65. (f) Bulls, A. R.; Schaefer, W. P.; Serfas, M.; Bercaw, J. E. Organometallics 1987, 6, 1219.
66. (g) Bandy, J. A.; Mtetwa, V. S. B.; Prout, K.; Green, J. C.; Davies, C. E.; Green, M. C. H.; Hazel, N. J.; Izguierdo, A.; Martin-polo, J. J. J. Chem. Soc., Dalton Trans 1985, 2037.
67. (h) Pattiasina, J. W.; Hissink, C. E.; de Boer, J. C.; Meetsma, A.; Teuben, J. H. J. Am. Chem. Soc. 1985, 107, 7758.
68. (I) Mcdade, C.; Green, J. C.; Bercaw, J. E. Organometallics 1982, 1, 1629.
69. (j) Bercaw, J. E. J. Am. Chem. Soc. 1974, 96, 5087.
70. 12d
71. + center, see: Horton, A. D.; de With, J. J. Chem. Soc. Chem. Commun. 1996, 1375-1376.
72. Pellecchia, C.; Grassi, A.; Immirzi, A. J. Am. Chem. Soc. 1993, 115, 1160-1162.
73. Yang, X.; Stern, C. L.; Marks, T. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1375.
74. - has been reported, see: Horton, A. D.; Frijins, J. H. G. Angew. Chem., Int. Ed. Engl. 1991, 30, 1152.
75. For a recent review article on the properties of MAO, see: Reddy, S. S.; Sivaram, S. Prog. Polym. Sci. 1995, 20, 309-367.