Chain-selective and regioselective ethylene and styrene dimerization reactions catalyzed by a well-defined cationic ruthenium hydride complex: New insights on the styrene dimerization mechanism

Organometallics

Volumn 29, Issue 15, 2010, Pages 3413-3417

  Lee, Do W ^a   Yi, Chae S ^a  

^a Marquette University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2-BUTENE; C-C BOND FORMATION; CARBON ISOTOPES; DEUTERIUM ISOTOPE EFFECT; DIMERIZATION REACTIONS; ELECTROPHILIC ADDITIONS; ETHYLENE DIMERIZATION; EYRING PLOT; FIRST-ORDER; H/D EXCHANGE; RATE-LIMITING STEPS; REGIO-SELECTIVE; ROOM TEMPERATURE; RUTHENIUM HYDRIDE COMPLEX; TEMPERATURE RANGE; TURNOVER RATE;

BUTENES; CARRIER MOBILITY; DEUTERIUM; DIMERIZATION; ETHYLENE; HYDROCARBONS; REGIOSELECTIVITY; RUTHENIUM; RUTHENIUM COMPOUNDS;

STYRENE;

EID: 77955131623     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om100468q     Document Type: Article

References (52)

1. Reviews: Pillai, S. M.; Ravindranathan, M.; Sivaram, S. Chem. Rev. 1986, 86, 353-399
2. Skupinska, J. Chem. Rev. 1991, 91, 613-648
3. Mecking, S. Coord. Chem. Rev. 2000, 203, 325-351
4. Speiser, F.; Braunstein, P.; Saussine, L. Acc. Chem. Res. 2005, 38, 784-793
5. Olivier-Bourbigou, H.; Saussine, L. In Applied Homogeneous Catalysis with Organometallic Compounds, 2nd ed.; Cornils, B.; Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Vol. 1.
6. Keim, W. Angew. Chem., Int. Ed. 1990, 29, 235-244
7. Keim, W.; Behr, A.; Röper, M. In Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 12.
8. Datta, S.; Fischer, M. B.; Wreford, S. S. J. Organomet. Chem. 1980, 188, 353-366
9. Schrock, R.; McLain, S.; Sancho, J. Pure Appl. Chem. 1980, 52, 729-732
10. Andes, C.; Harkins, S. B.; Murtuza, S.; Oyler, K.; Sen, A. J. Am. Chem. Soc. 2001, 123, 7423-7424
11. Yu, Z.-X.; Houk, K. N. Angew. Chem., Int. Ed. 2003, 42, 808-811
12. Bhalla, G.; Oxgaard, J.; Goddard, W. A., III; Periana, R. A. Organometallics 2005, 24, 5499-5502
13. Recent selected examples with Cr catalysts: Dixon, J. T.; Green, M. J.; Hess, F. M.; Morgan, D. H. J. Organomet. Chem. 2004, 689, 3641-3668
14. McGuinness, D. S.; Wasserscheid, P.; Keim, W.; Morgan, D.; Dixon, J. T.; Bollmann, A.; Maumela, H.; Hess, F.; Englert, U. J. Am. Chem. Soc. 2003, 125, 5272-5273
15. Blann, K.; Bollmann, A.; Dixon, J. T.; Hess, F. M.; Killian, E.; Maumela, H.; Morgan, D. H.; Neveling, A.; Otto, S.; Overett, M. J. Chem. Commun. 2005, 620-621
16. Agapie, T.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 2007, 129, 14281-14295
17. Arteaga-Müller, R.; Tsurugi, H.; Saito, T.; Yanagawa, M.; Oda, S.; Mashima, K. J. Am. Chem. Soc. 2009, 131, 5370-5371
18. Examples with Ti catalysts: Deckers, P. J. W.; Hessen, B.; Teuben, J. H. Angew. Chem., Int. Ed. 2001, 40, 2516-2519
19. Otten, E.; Batinas, A. A.; Meetsma, A.; Hessen, B. J. Am. Chem. Soc. 2009, 131, 5298-5312
20. Suzuki, Y.; Kinoshita, S.; Shibahara, A.; Ishii, S.; Kawamura, K.; Inoue, Y.; Fujita, T. Organometallics 2010, 29, 2394-2396
21. Ittel, S. D.; Johnson, L. K.; Brookhart, M. Chem. Rev. 2000, 100, 1169-1204
22. Mecking, S. Angew. Chem., Int. Ed. 2001, 40, 534-540
23. DiRenzo, G. M.; White, P. S.; Brookhart, M. J. Am. Chem. Soc. 1996, 118, 6225-6234
24. Doherty, M. D.; Trudeau, S.; White, P. S.; Morken, J. P.; Brookhart, M. Organometallics 2007, 26, 1261-1269
25. Shiotsuki, M.; White, P. S.; Brookhart, M.; Templeton, J. L. J. Am. Chem. Soc. 2007, 129, 4058-4067
26. Burns, C. T.; Jordan, R. F. Organometallics 2007, 26, 6726-6736
27. Conley, M. P.; Burns, C. T.; Jordan, R. F. Organometallics 2007, 26, 6750-6759
28. Ajellal, N.; Kuhn, M. C. A.; Boff, A. D. G.; Hörner, M.; Thomas, C. M.; Carpentier, J.-F.; Casagrande, O. L., Jr. Organometallics 2006, 25, 1213-1216
29. Zhang, S.; Nomura, K. J. Am. Chem. Soc. 2010, 132, 4960-4965
30. White, S.; Bennett, B. L.; Roddick, D. M. Organometallics 1999, 18, 2536-2542
31. Basu, S.; Arulsamy, N.; Roddick, D. M. Organometallics 2008, 27, 3659-3665
32. Ivin, K. J.; Mol, J. C. Olefin Metathesis and Metathesis Polymerization; Academic Press: London, 1997.
33. Taoufik, M.; Le Roux, E.; Thivolle-Cazat, J.; Basset, J.-M. Angew. Chem., Int. Ed. 2007, 46, 7202-7205
34. Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis, 2 nd ed.; Wiley: New York, 1992.
35. Jira, R. In Applied Homogeneous Catalysis with Organometallic Compounds, 2 nd ed.; Cornils, B.; Herrmann, W A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Vol. 1.
36. Yi, C. S.; Lee, D. W. Organometallics 2009, 28, 4266-4268
37. Yi, C. S.; Lee, D. W. Organometallics 2010, 29, 1883-1885
38. Yi, C. S.; Zeczycki, T. N.; Guzei, I. A. Organometallics 2006, 25, 1047-1051
39. Yi, C. S.; Lee, D. W. Organometallics 2009, 28, 947-949
40. See the Supporting Information for experimental details.
41. Jiang, Z.; Sen, A. J. Am. Chem. Soc. 1990, 112, 9655-9657
42. Jiang, Z.; Sen, A. Organometallics 1993, 12, 1406-1415
43. Kretschmer, W. P.; Troyanov, S. I.; Meetsma, A.; Hessen, B.; Teuben, J. H. Organometallics 1998, 17, 284-286
44. Tsuchimoto, T.; Kamiyama, S.; Negoro, R.; Shirakawa, E.; Kawakami, Y. Chem. Commun. 2003, 852-853
45. Yamada, S.; Obora, Y.; Sakaguchi, S.; Ishii, Y. Bull. Chem. Soc. Jpn. 2007, 80, 1194-1198
46. Kondo, T.; Takagi, D.; Tsujita, H.; Ura, Y.; Wada, K.; Mitsudo, T. Angew. Chem., Int. Ed. 2007, 46, 5958-5961
47. Higashimura, M.; Imamura, K.; Yokogawa, Y.; Sakakibara, T. Chem. Lett. 2004, 33, 728-729
48. Jones, W. D. Acc. Chem. Res. 2003, 36, 140-146
49. Parkin, G. Acc. Chem. Res. 2009, 42, 315-325
50. We previously observed a similar inverse deuterium isotope effect in ruthenium-catalyzed hydrogenation of olefins: Yi, C. S.; Lee, D. W. Organometallics 1999, 18, 5152-5156
51. Singleton, D. A.; Thomas, A. A. J. Am. Chem. Soc. 1995, 117, 9357-9358
52. Frantz, D. E.; Singleton, D. A.; Snyder, J. P. J. Am. Chem. Soc. 1997, 119, 3383-3384