Platinum-catalyzed intramolecular asymmetric hydroarylation of unactivated alkenes with indoles

Organic Letters

Volumn 8, Issue 17, 2006, Pages 3801-3804

  Han, Xiaoqing ^a   Widenhoefer, Ross A ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748585951     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061441b     Document Type: Article

References (46)

1. (a) Tan, K. L.; Park, S.; Ellman, J. A.; Bergman, R. G. J. Org. Chem. 2004, 69, 7329.
2. (b) Thalji, R. K.; Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. J. Org. Chem. 2005, 70, 6775.
3. (c) Wiedemann, S. H.; Ellman, J. A.; Bergman, R. G. J. Org. Chem. 2006, 71, 1969.
4. (d) Wiedemann, S. H.; Lewis, J. C.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2006, 128, 2452.
5. (e) Thalji, R. K.; Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 9692.
6. (f) Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2003, 5, 1301.
7. (g) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 13964.
8. (h) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 2685.
9. (i) Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1999, 121, 6616.
10. (a) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826 and references therein.
11. (b) Lail, M.; Arrowood, B. N.; Gunnoe, T. B. J. Am. Chem. Soc. 2003, 125, 7506.
12. Youn, S. W.; Pastine, S. J.; Sames, D. Org. Lett. 2004, 6, 581.
13. (a) Matsumoto, T.; Taube, D. J.; Periana, R. A.; Taube, H.; Yoshida, H. J. Am. Chem. Soc. 2000, 122, 7414.
14. (b) Matsumoto, T.; Periana, R. A.; Taube, D. J.; Yoshida, H. J. Mol. Catal. A: Chem 2002, 180, 1.
15. Jordan, R. F.; Taylor, D. F. J. Am. Chem. Soc. 1989, 111, 778.
16. (a) O'Malley, S. J.; Tan, K. L.; Watzke, A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2005, 127, 13496.
17. (b) Thalji, R. K.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 7192.
18. (c) Wilson, R. M.; Thalji, R. K.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2006, 8, 1745.
19. (a) Bergman, J.; Pelcman, B. Pure Appl. Chem. 1990, 62, 1967.
20. (b) Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797.
21. (c) Saxton, J. E. Nat. Prod. Rep. 1997, 559.
22. (a) Widenhoefer, R. A. Pure Appl. Chem. 2004, 76, 671 and references therein.
23. (c) Han, X.; Wang, X.; Pei, T.; Widenhoefer, R. A. Chem.-Eur. J. 2004, 10, 6333.
24. (d) Qian, H.; Pei, T.; Widenhoefer, R. A. Organometallics 2005, 24, 287.
25. (e) Liu, C.; Widenhoefer, R. A. Tetrahedron Lett. 2005, 46, 285.
26. Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 3700.
27. (a) Han, X.; Widenhoefer, R. A. Angew. Chem., Int. Ed. 2006, 45, 1747.
28. (b) Bender, C. F.; Widenhoefer, R. A. J. Am. Chem. Soc. 2005, 127, 1070.
29. (c) Wang, X.; Widenhoefer, R. A. Organometallics 2004, 23, 1649.
30. (d) Qian, H.; Widenhoefer, R. A. Org. Lett. 2005, 7, 2635.
31. Qian, H.; Han, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 9536.
32. 9 but was unfortunately reported incorrectly. See: Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 10493.
33. Pignat, K.; Vallotto, J.; Pinna, F.; Strukul, G. Organometallics 2000, 19, 5160.
34. (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York. 1994.
35. (b) Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
36. See the Supporting Information for a more detailed description of the optimization studies.
37. Two control experiments ruled out the possibility of acid- or silver-catalyzed asymmetric hydroarylation. In one experiment, a solution of 3 that contained a catalytic mixture of (5)-4 (10 mol %), HCl (10 mol %). and HOTf (10 mol %) in methanol was heated at 60 °C for 24 h. GC analysis of the crude reaction mixture revealed no consumption of 3. In a second experiment, a solution of 3 and a catalytic mixture of (S)-4 (10 mol %) and AgOTf (5 mol %) in methanol was heated at 60 °C for 24 h. GC analysis of the crude reaction mixture again revealed no consumption of 3.
38. (a) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101.
39. (b) Schmid, R.; Broger, E. A.; Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.; Müller, R. K.; Scalone, M.; Schoettel, G.; Zutter, U. Pure Appl. Chem. 1996, 68, 131.
40. (c) Blaser, H.-U.; Buser, H.-P.; Jalett, H.-P.; Pugin, B.; Spindler, F. Synlett 1999, 867.
41. Trabesinger, G.; Albinati, A.; Feiken, N.; Kunz, R. W.; Pregosin, P. S.; Tschoerner, M. J. Am. Chem. Soc. 1997, 119, 6315.
42. Tschoerner, M.; Pregosin, P. S. Organometallics 1999, 18, 670.
43. (a) Selvakumar, K.; Valentini, M.; Pregosin, P. S. Organometallics 2000, 19, 1299.
44. (b) Faller, J. W.; Wilt, J. C. Org. Lett. 2005, 7, 633.
45. 9 respectively.
46. Girard, C.; Kagan, H. B. Angew Chem., Int. Ed. 1998, 37, 2922.