Intermolecular hydroarylation of unactivated olefins catalyzed by homogeneous platinum complexes

Angewandte Chemie - International Edition

Volumn 47, Issue 40, 2008, Pages 7694-7696

  Luedtke, Avery T ^a   Goldberg, Karen I ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

Arenes; C H activation; Hydroarylation; Olefins; Platinum

Indexed keywords

EID: 54749110970     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800524     Document Type: Article

References (33)

1. a) T. Matsumoto, Catal. Surv. Asia 2007, 11, 31;
2. b) T. B. Gunnoe, L. A. Goj, Curr. Org. Chem. 2005, 9, 671;
3. c) V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 2002, 102, 1731;
4. d) F. Kakiuchi, S. Murai, Acc. Chem. Res. 2002, 35,826.
5. a) G. Bhalla, J. Oxgaard, W. A. Goddard III, R. A. Periana, Organometallics 2005, 24, 3229;
6. b) J. Oxgaard, R. A. Periana, W. A. Goddard III, J. Am. Chem. Soc. 2004, 126, 11658;
7. c) J. Oxgaard, R. P. Muller, W. A. Goddard III, R. A. Periana, J. Am. Chem. Soc. 2004, 126, 352;
8. d) R. A. Periana, X. Y. Liu, G. Bhalla, Chem. Commun. 2002, 3000;
9. e) T. Matsumoto, R. A. Periana, D. J. Taube, H. Yoshida, J. Mol. Catal. A 2002, 180, 1;
10. f) T. Matsumoto, H. Yoshida, Catal. Lett. 2001, 72, 107;
11. g) T. Matsumoto, D. J. Taube, R. A. Periana, H. Taube, H. Yoshida, J. Am. Chem. Soc. 2000, 122, 7414.
12. a) N. A. Foley, M. Lail, J. P. Lee, T. B. Gunnoe, T. R. Cundari, J. L. Petersen, J. Am. Chem. Soc. 2007, 129, 6765;
13. b) N. A. Foley, M. Lail, T. B. Gunnoe, T. R. Cundari, P. D. Boyle, J. L. Petersen, Organometallics 2007, 26, 5507;
14. c) M. Lail, C. M. Bell, D. Conner, T. R. Cundari, T. B. Gunnoe, J. L. Petersen, Organometallics 2004, 23, 5007;
15. d) J. Oxgaard, W. A. Goddard III, J. Am. Chem. Soc. 2004, 126, 442;
16. e) M. Lail, B. N. Arrowood, T. B. Gunnoe, J. Am. Chem. Soc. 2003, 125, 7506.
17. a) M. Lersch, M. Tilset, Chem. Rev. 2005, 105, 2471;
18. b) Activation and Functionalization of C-H Bonds (Eds.: K. I. Goldberg, A. S. Goldman), A CS Symposium Series 885, Washington, 2004;
19. c) U. Fekl, K. I. Goldberg, Adv. Inorg. Chem. 2003, 54, 259.
20. M. G. MacDonald, C. N. Kostelansky, P. S. White, J. L. Templeton, Organometallics 2006, 25, 4560.
21. A recent success with Pt was reported as this Communication was in press: B. A. McKeown, N. A. Foley, J. P. Lee, T. B. Gunnoe, Organometallics, 2008, 27, 4031.
22. D. Karshtedt, A. T. Bell, T. D. Tilley, Organometallics 2004, 23, 4169.
23. D. Karshtedt, J. L. McBee, A. T. Bell, T. D. Tilley, Organometallics 2006, 25, 1801.
24. A. T. Luedtke, K. I. Goldberg, Inorg. Chem. 2007, 46, 8496.
25. J. J. Klappa, A. E. Rich, K. McNeill, Org. Lett. 2002, 4, 435.
26. See the Supporting Information.
27. 2 are consistent with the proposed dimeric structure.
28. For a similar reaction see: C. N. Iverson, C. A. G. Carter, R. T. Baker, J. D. Scollard, J. A. Labinger, J. E. Bercaw, J. Am. Chem. Soc. 2003, 125, 12674.
29. 6]ethylbenzene.
30. Evidence has not yet been obtained to indicate the stereochemistry of the proposed intermediates.
31. a) B. J. Wik, M. Lersch, A. Krivokapic, M. Tilset, J. Am. Chem. Soc. 2006, 128, 2682;
32. b) C. M. Norris, S. Reinartz, P. S. White, J. L. Templeton, Organometallics 2002, 21, 5649.
33. TONs were determined by GC-FID using the relative peak areas versus an internal naphthalene standard. Relative response factors versus the naphthalene standard were determined from authentic samples that are commercially available: ethylbenzene, 2-phenylp ropane,1-phenyl propane, p-ethyltoluene, oethyltoluene, phenylc yclohexane, m-cymene, p-cymene,and ocymene. The relative response factors of the other products were assumed to be unity.