Intermolecular coupling of alkenes to heterocycles via C-H bond activation

Journal of Organic Chemistry

Volumn 69, Issue 21, 2004, Pages 7329-7335

  Tan, Kian L ^a   Park, Steve ^a   Ellman, Jonathan A ^a   Bergman, Robert G ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; BONDING; CARBON; CATALYSTS; ESTERS; HYDROGEN; OPTIMIZATION; RHODIUM;

ACETALS; HETEROCYCLES; INTERMOLECULAR COUPLING; NITRILES;

OLEFINS;

ACETAL DERIVATIVE; ALKENE; ESTER; HETEROCYCLIC COMPOUND; NITRILE; PHTHALIMIDE DERIVATIVE;

ARTICLE; CATALYST; ELECTRON TRANSPORT; HYDROGEN BOND; MOLECULAR INTERACTION; REACTION ANALYSIS; SUBSTITUTION REACTION;

ALKENES; CATALYSIS; CYCLIZATION; HETEROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE; RHODIUM; SOLVENTS;

EID: 5444275842     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048666p     Document Type: Article

References (55)

1. For reviews of C-H activation see the following references: (a) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879-2932.
2. (b) Ryabov, A. D. Chem. Rev. 1990, 90, 403-424.
3. For reviews on hydroarylation see the following references: (a) Miura, M.; Nomura, M. In Cross-Coupling Reactions; Springer-Verlag Berlin: Berlin, 2002; Vol. 219, pp 211-241.
4. (b) Guari, Y.; Sabo-Etienne, S.; Chaudret, B. Eur. J. Inorg. Chem. 1999, 1047-1055.
5. (c) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1699-1712.
6. (a) Kakiuchi, F.; Murai, S. Topics in Organometallic Chemistry; 1999; Vol. 3.
7. (b) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731-1769.
8. (c) Jia, C. G.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633-639.
9. (a) Matsumoto, T.; Taube, D. J.; Periana, R. A.; Taube, H.; Yoshida, H. J. Am. Chem. Soc. 2000, 122, 7414-7415.
10. (b) Periana, R. A.; Liu, X. Y.; Bhalla, G. Chem. Commun. 2002, 3000-3001.
11. (c) Matsumoto, T.; Periana, R. A.; Taube, D. J.; Yoshida, H. J. Catal. 2002, 206, 272-280.
12. (d) Matsumoto, T.; Periana, R. A.; Taube, D. J.; Yoshida, H. J. Mol. Catal. A: Chem. 2002, 180, 1-18.
13. (e) Oxgaard, J.; Muller, R. P.; Goddard, W. A.; Periana, R. A. J. Am. Chem. Soc. 2004, 126, 352-363.
14. (a) Lail, M.; Arrowood, B. N.; Gunnoe, T. B. J. Am. Chem. Soc. 2003, 125, 7506-7507.
15. (b) Oxgaard, J.; Goddard, W. A. J. Am. Chem. Soc. 2004, 126, 442-443.
16. (a) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 9578-9579.
17. (b) Beccalli, E. M.; Broggini, G. Tetrahedron Lett. 2003, 44, 1919-1921.
18. (a) Jia, C. G.; Piao, D. G.; Oyamada, J. Z.; Lu, W. J.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992-1995.
19. (b) Fujiwara, Y.; Jia, C. G. Pure Appl. Chem. 2001, 73, 319-324.
20. Youn, S. W.; Pastine, S. J.; Sames, D. Org. Lett. 2004, 6, 581-584.
21. (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529-531.
22. (b) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Pure Appl. Chem. 1994, 66, 1527-1534.
23. (c) Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62-83.
24. Jun, C. H.; Hong, J. B.; Kim, Y. H.; Chung, K. Y. Angew. Chem., Int. Ed. 2000, 39, 3440.
25. Kakiuchi, F.; Sonoda, M.; Tsujimoto, T.; Chatani, N.; Murai, S. Chem. Lett. 1999, 1083-1084.
26. Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1999, 121, 6616-6623.
27. Trost, B. M.; Imi, K.; Davies, I. W. J. Am. Chem. Soc. 1995, 117 5371-5372
28. (a) Lim, Y. G.; Kim, Y. H.; Kang, J. B. Chem. Commun. 1994, 2267-2268.
29. (b) Lim, Y. G.; Kang, J. B.; Kim, Y. H. Chem. Commun. 1996, 585-586.
30. (c) Lim, Y. G.; Kang, J. B.; Kim, Y. H. J. Chem. Soc., Perkin Trans, 1 1998, 699-707.
31. (a) Thalji, R. K.; Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 9692-9693.
32. (b) Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2003, 5, 1301-1303.
33. (a) Jordan, R. F.; Taylor, D. F. J. Am. Chem. Soc. 1989, 111, 778-779.
34. (b) Dagorne, S.; Rodewald, S.; Jordan, R. F. Organometallics 1997, 16, 5541-5555.
35. (c) Jordan, R. F.; Bradley, P. K.; Lapointe, R. E.; Taylor, D. F. New J. Chem. 1990, 14, 505-511.
36. Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 2685-2686.
37. Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 3202-3203.
38. Lewis, J. C.; Wiedemann, S. H.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2004, 6, 35-38.
39. (a) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 13964-13965.
40. (b) Tan, K. L.; Vasudevan, A.; Bergman, R. G.; Ellman, J. A.; Souers, A. J. Org. Lett. 2003, 5, 2131-2134.
41. (c) Wiedemann, S. H.; R. G. Bergman; Ellman, J. A. Org. Lett. 2004, 6, 1685-1687.
42. 4NCl did not result in acceleration of the reaction showing that the additive effect is not a result of ionic strength of the medium.
43. Kocher, C.; Herrmann, W. A. J. Organomet. Chem. 1997, 532, 261-265.
44. The regioselectivity of the alkylation of 6 was determined by X-ray crystallography.
45. A carbamate protecting group was used successfully in the coupling with an oxazoline derivative; see ref 20c.
46. 3 we found that a variable amount (1-2 equiv) of HCl was incorporated. However, this did not appear to affect the efficiency of the reaction.
47. (a) Grushin, V. V.; Alper, H. Organometallics 1991, 10, 1620-1622.
48. (b) Gusev, D. G.; Bakhmutov, V. I.; Grushin, V. V.; Volpin, M. E. Inorg. Chim. Acta 1990, 175, 19-21.
49. (c) James, B. R.; Preece, M.; Robinson, S. D. Inorg. Chim. Acta 1979, 34, L219-L221.
50. (d) Intille, G. M. Inorg. Chem. 1972, 11, 1, 695.
51. McGuinness, D. S.; Saendig, N.; Yates, B. F.; Cavell, K. J. J. Am. Chem. Soc. 2001, 123, 4029-4040.
52. Clement, N. D.; Cavell, K. J. Angew. Chem., Int. Ed. 2004, 43, 3845-3847.
53. The cone angles were either calculated using the procedure described by Tolman or were obtained from the following references: (a) Tolman, C. A. Chem. Rev. 1977, 77, 313-348.
54. (b) Rahman, M. M.; Liu, H. Y.; Eriks, K.; Frock, A.; Giering, W. P. Organometallics 1989, 8, 1-7.
55. 2(Biphenyl) is electronically different from the other phosphines screened, and therefore it was not plotted on this figure.