Arylation and aroylation reactions of unsaturated compounds catalyzed by rhodium complexes

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 58, Issue 6, 2000, Pages 578-586

  Miura, Masahiro ^a   Nomura, Masakatsu ^b  

^a OSAKA UNIVERSITY   (Japan)

^b NONE

Author keywords

Aldehydes; Alkenes; Alkynes; Aromatic acid anhydrides; Aromatic compounds; Aroyl chlorides; Aroylation; Carbonyl compounds; Rhodium; Rylation

Indexed keywords

EID: 0141771565     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.58.578     Document Type: Article

References (69)

1. J. Tsuji, "Palladium Reagents and Catalysts", Wiley, Chichester, 1995
2. "Metal-Catalyzed Cross-Coupling Reactions", ed. by P. J. Stang, F. Diederich, Wiley-VCH, Weinheim, 1997
3. J. Blum, E. Oppenheimer, E. D. Bergmann, J. Am. Chem. Soc., 89, 2338 (1967)
4. K. Ohno, J. Tsuji, J. Am. Chem. Soc., 90, 99 (1968)
5. J. A. Kampmeier, S. Mahalingam, Organometallics, 3, 489 (1984)
6. C.-M. Anderson, A. Hallberg, J. Org. Chem., 53, 4257 (1988)
7. Y. Tohda, K. Sonogashira, N. Hagihara, Synthesis, 1977, 777
8. (a) H.-U. Blaser, A. Spencer, J. Organomet. Chem., 233, 267 (1982);
9. (b) A. Spencer, J. Organomet. Chem., ibid., 265, 323 (1984)
10. M. Miura, H. Hashimoto, K. Itoh, M. Nomura, J. Chem. Soc., Perkin Trans. 1, 1990, 2207
11. (a) Y. Obora, Y. Tsuji, T. Kawamura, J. Am. Chem. Soc., 115, 10414 (1993);
12. (b) Y. Obora, Y. Tsuji, T. Kawamura, idem, J. Am. Chem. Soc., ibid., 117, 9814 (1995)
13. L. S. Hegedus, P. M. Kendall, S. M. Lo, J. R. Sheats, J. Am. Chem. Soc., 97, 5448 (1975)
14. J. Schwartz, J. B. Cannon, J. Am. Chem. Soc., 96, 4721 (1974)
15. K. Kokubo, K. Matsumasa, M. Miura, M. Nomura, J. Org. Chem., 61, 6941 (1996)
16. H. Ogoshi, J.-I. Setsune, Y. Nanbo, Z.-I. Yoshida, J. Organomet. Chem., 159, 329 (1978)
17. R. Hua, S. Shimada, M. Tanaka, J. Am. Chem. Soc., 120, 12365 (1998)
18. L.-Y. Huang, U. R. Aulwurm, F. W. Heinemann, H. Kisch, Eur. J. Inorg. Chem., 1998, 1951
19. S. P. Dent, C. Eaborn, A. Pidcock, J. Chem. Soc., Chem. Commun., 1970, 1703
20. V. V. Grushin, H. Alper, J. Org. Chem., 56, 5159 (1991)
21. K. Kokubo, K. Matsumasa, M. Miura, M. Nomura, J. Organomet. Chem., 560, 217 (1998)
22. K. Kokubo, M. Miura, M. Nomura, Organometallics, 14, 4521 (1995)
23. R. Grigg, V. Sridharan, P. Stevenson, S. Sukirthalingam, T. Worakun, Tetrahedron, 46, 4003 (1990)
24. S. Iyer, J. Organomet. Chem., 490, C 27 (1995)
25. V. V. Grushin, H. Alper, Organometallics, 10, 1620 (1991)
26. M. Sakai, H. Hayashi, N. Miyaura, Organometallics, 16, 4229 (1997)
27. S. Oi, M. Moro, S. Inoue, Chem. Commun., 1997, 1621
28. M. Sakai, M. Ueda, N. Miyaura, Angew. Chem., Int. Ed. Engl., 37, 3279 (1998)
29. S. Oi, M. Moro, S. Ono, S. Inoue, Chem. Lett., 1998, 83
30. (a) Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998);
31. (b) Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, N. Miyaura, idem. Tetrahedron Lett., 40, 6957 (1999)
32. F. Kakiuchi, S. Murai, "Activation of Unreactive Bonds and Organic Synthesis", ed. by S. Murai, Springer, Berlin, 1999, p 47
33. G. Dyker, Angew. Chem., Int. Ed. Engl., 38, 1698 (1999)
34. Y. Guari, S. Sabo-Etienne, B. Chaudret, Eur. J. Inorg. Chem., 1999, 1047
35. (a) P. Hong, H. Yamazaki, K. Sonogashira, N. Hagihara, Chem. Lett., 1978, 535;
36. (b) H. Yamazaki, P. Hong, J. Mol. Catal., 21, 133 (1983)
37. (a) M. Tanaka, CHEMTECH, 1989, 59;
38. (b) Y. Tokunaga, T. Sakakura, M. Tanaka, J. Mol. Catal., 56, 305 (1989)
39. (a) S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, Nature (London), 366, 529 (1993);
40. (b) F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, S. Murai, Bull. Chem. Soc. Jpn., 68, 62 (1995);
41. (c) M. Sonoda, F. Kakiuchi, A. Kamatani, N. Chatani, S. Murai, Bull. Chem. Soc. Jpn., ibid., 70, 3117 (1997)
42. (a) S. Murai, J. Synth. Org. Chem. Jpn., 52, 992 (1994);
43. (a) Y.-G. Lim, Y. H. Kim, J.-B. Kang, J. Chem. Soc., Chem. Commun., 1994, 2267;
44. (b) Y.-G. Lim, J-B. Kang, Y. H. Kim, J. Chem. Soc., Perkin Trans. 1, 1996, 2201
45. U. R. Aulwurm, J. U. Melchinger, H. Kisch, Organometallics, 14, 3385 (1995)
46. C. P. Lenges, M. Brookhart, J. Am. Chem. Soc., 121, 6616 (1999)
47. (a) T. Satoh, Y. Kawamura, M. Miura, M. Nomura, Angew. Chem., Int. Ed. Engl., 36, 1740 (1997);
48. (b) T. Satoh, J.-I. Inoh, Y. Kawamura, Y. Kawamura, M. Miura, M. Nomura, Bull. Chem. Soc. Jpn., 71, 2239 (1998)
49. T. Satoh, Y. Nishinaka, M. Miura, M. Nomura, Chem. Lett., 1999, 615
50. B. Bosnich, Acc. Chem. Res., 31, 667 (1998)
51. J. W. Suggs, J. Am. Chem. Soc., 79, 489 (1979)
52. (a) C.- H. Jun, H. Ree, J-B. Hong, J. Org. Chem., 62, 1200 (1997);
53. (b) C.- H. Jun, J-B. Hong, Org. Lett., 1, 887 (1999)
54. C.- H. Jun, C.-W. Huh, S.-J. Na, Angew. Chem., Int. Ed. Engl., 37, 145 (1998)
55. C.- H. Jun, J.-B. Hong, D.-Y. Lee, Synlett, 1999, 1
56. (a) K. Kokubo, K. Matsumasa, M. Miura, M. Nomura, J. Org. Chem., 62, 4564 (1997);
57. (b) K. Kokubo, K. Matsumasa, M. Miura, M. Nomura, idem, Bull. Chem. Soc. Jpn., 72, 303 (1999)
58. T. B. Marder, D. C. Roe, D. Milstein, Organometallics, 7, 1451 (1988)
59. C. P. Lenges, M. Brookhart, J. Am. Chem. Soc., 119, 3165 (1997);
60. C. P. Lenges, P. S. White, M. Brookhart, J. Am. Chem. Soc., ibid., 120, 6965 (1998)
61. T. Kondo, M. Akazome, Y. Tsuji, Y. Watanabe, J. Org. Chem., 55, 1286 (1990)
62. T. Tsuda, T. Kiyoi, T. Saegusa, J. Org. Chem., 55, 2554 (1990)