Stereoselective cis-addition of aromatic C - H bonds to alkynes catalyzed by dinuclear palladium complexes

Journal of the American Chemical Society

Volumn 125, Issue 40, 2003, Pages 12102-12103

  Tsukada, Naofumi ^a   Mitsuboshi, Tomohiro ^a   Setoguchi, Hiroyuki ^a   Inoue, Yoshio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AROMATIC COMPOUND; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; COMPLEX FORMATION; IRRADIATION; PHASE TRANSITION; PHOTOCHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0141989922     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0375075     Document Type: Article

References (52)

1. (a) Kakiuchi, F.; Murai, S. Activation of C-H bonds: Catalytic Reactions. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: Berlin, 1999; pp 47-79.
2. (b) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698.
3. (c) Guari, Y.; Sabo-Etienne, S.; Chaudret, B. Eur. J. Inorg. Chem. 1999, 1047.
4. (d) Crabtree, R. H. J. Chem. Soc., Dalton Trans. 2001, 2437.
5. (e) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
6. (a) Trost, B. M. Science 1991, 254, 1471.
7. (b) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
8. For alkenes: (a) Lewis, L. N.; Smith, J. F. J. Am. Chem. Soc. 1986, 108, 2728.
9. (b) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529.
10. (c) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Pure Appl. Chem. 1994, 66, 1527.
11. (d) Sonoda, M.; Kakiuchi, F.; Chatani, N.; Murai, S. J. Organomet. Chem. 1995, 504, 151.
12. (e) Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62.
13. (f) Sonoda, M.; Kakiuchi, F.; Kamatani, A.; Chatani, N.; Murai, S. Chem. Lett. 1996, 109.
14. (g) Kakiuchi, F.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1996, 111.
15. (h) Murai, S.; Chatani, N.; Kakiuchi, F. Pure Appl. Chem. 1997, 69, 589.
16. (i) Kakiuchi, F.; Sato, T.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1999, 19.
17. (j) Kakiuchi, F.; Sonoda, M.; Tsujimoto, T.; Chatani, N.; Murai, S. Chem. Lett. 1999, 1083.
18. (k) Lim, Y.-G.; Kim, Y. H.; Kang, J.-B. J. Chem. Soc., Chem. Commun. 1994, 2267.
19. (l) Lim, Y.-G.; Kang, J.-B.; Kim, Y. H. J. Chem. Soc., Perkin Trans. 1 1996, 2201.
20. (m) Lim, Y.-G.; Han, J.-S.; Yang, S.-S.; Chun, J. H. Tetrahedron Lett. 2001, 42, 4853.
21. (n) Jun, C.-H.; Hong, J.-B.; Kim, Y.-H.; Chung, K.-Y. Angew. Chem., Int. Ed. 2000, 42, 4853.
22. (o) Guari, Y.; Sabo-Etienne, S.; Chaudret, B. J. Am. Chem. Soc. 1998, 120, 4228.
23. (p) Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1999, 121, 6616.
24. For alkynes: (a) Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681.
25. (b) Kakiuchi, F.; Sato, T.; Tsujimoto, T.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1998, 1053.
26. (c) Halbritter, G.; Knoch, F.; Wolski, A.; Kisch, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 1603.
27. (d) Aulwurm, U. R.; Melchinger, J. U.; Kisch, H. Organometallics 1995, 14, 3385.
28. (e) Durr, U.; Kisch, H. Synlett 1997, 1335.
29. (f) Satoh, T.; Nishiyama, Y.; Miura, M.; Nomura, M. Chem. Lett. 1999, 615,
30. (g) Harris, P. W. R.; Richard, C. E. F.; Woodgate, P. D. J. Organomet. Chem. 1999, 589, 168.
31. (h) Lim, Y.-G.; Lee, K.-H.; Koo, B. T.; Kang, J.-B. Tetrahedron Lett. 2001, 42, 7609.
32. Sasaki, K.; Sakakura, T.; Tokunaga, Y.; Wada, K.; Tanaka, M. Chem. Lett. 1988, 685.
33. (a) Matsumoto, T.; Taube, D. J.; Periana, R. A.; Taube, H.; Yoshida, H. J. Am. Chem. Soc. 2000, 122, 7414.
34. (b) Matsumoto, T.; Yoshida, H. Chem. Lett. 2001, 72, 107.
35. (c) Matsumoto, T.; Periana, R. A.; Taube, D. J.; Yoshida, H. J. Mol. Catal. A 2002, 180, 1.
36. (d) Periana, R. A.; Liu, X. Y.; Bhalla, G. Chem. Commun. 2002, 3000.
37. (a) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
38. (b) Jia, C.; Lu, W.; Oyamada, J.; Kitamura, T.; Matsuda, K.; Irie, M.; Fujiwara, Y. J. Am. Chem. Soc. 2000, 122, 7252.
39. (a) Hong, P.; Cho, B.-R.; Yamazaki, H. Chem. Lett. 1979, 339.
40. (b) Hong, P.; Cho, B.-R.; Yamazaki, H. Chem. Lett. 1980, 507.
41. (c) Yamazaki, H.; Hong, P. J. Mol. Catal. 1983, 21, 133.
42. (d) Hong, P.; Mise, T.; Yamazaki, H. Bull. Chem. Soc. Jpn. 1990, 63, 247.
43. Tokunaga, Y.; Sakakura, T.; Tanaka, M. J. Mol. Catal. 1989, 56, 305.
44. Boese, W. T.; Goldman, A. S. Organometallics 1991, 10, 782.
45. Tsukada, N.; Tamura, O.; Inoue, Y. Organometallics 2002, 21, 2521.
46. Grushin, V. V.; Alper, H. Organometallics 1993, 12, 1890.
47. (a) Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390.
48. (b) Ishiyama, T.; Takagi, J.; Hartwig, J. F.; Miyaura, N. Angew. Chem., Int. Ed. 2002, 41, 3056.
49. (c) Cho, J.-Y.; Iverson, C. N.; Smith, M. R., III. J. Am. Chem. Soc. 2000, 122, 12868.
50. (d) Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E., Jr.; Smith, M. R., III. Science 2002, 295, 305.
51. 2]X are thermolytically inert at ambient temperature probably due to trans arrangement for R and H. (a) Stockland, R. A., Jr.; Anderson, G. K.; Rath, N. P. J. Am. Chem. Soc. 1999, 121, 7945.
52. (b) Stockland, R. A., Jr.; Anderson, G. K.; Rath, N. P. Inorg. Chim. Acta 2000, 300-302, 395.