Highly selective cross-coupling reactions of organosilicon compounds mediated by fluoride ion and a palladium catalyst

Synlett

Volumn 1991, Issue 12, 1991, Pages 845-853

  Hatanaka, Yasuo ^a   Hiyama, Tamejiro ^a  

^a Sagami Research Center   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84988124945     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1002/chin.199225331     Document Type: Article

References (63)

1. Heck, R.F. Palladium Reagents in Organic Syntheses; Academic Press: New York, 1985.
2. Kumada, M. Pure Appl. Chem. 1980, 52, 669.
3. Miyaura, N.; Suzuki, A. Yuki Gosel Kagaku Kyokai Shi 1988, -0, 848.
4. Negishi, E. Acc. Chem. Res. 1982, 15, 340.
5. Negishi, E. In Current Trends in Organic Synthesis, Nozaki, H., Ed.; Pergamon: Oxford, 1983: p. 269.
6. Stille, J.K. Angew. Chem. 1986, 98, 504
7. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
8. Posner, G.H. Org. React. 1975, 22, 253.
9. Tamao, K. Yuki Gosei Kagaku Kyokai Shi 1990, 48, 457.
10. Hiyama, T. Orgaometallic News, Kinki Chemical Society, Japan, 1987, No 1, p.1.
11. Hallberg, A.; Westerlund, C. Chem. Lett. 1982, 1933.
12. Karabelas, K.; Hallberg, A. J. Org. Chem. 1989, 54, 1773.
13. Yoshida, J.; Tamao, K.; Yamamoto, H.; Kakui, T; Uchida, T.; Kumada, M. Orgnometallics 1982, 1, 542.
14. Ikenaga, K.; Kikukawa, K.; Matsuda, T. J. Chem. Soc. Perkin Tram 1 1986, 1959.
15. Middleton, W.J.; U.S. Patent 3940402, 1976
16. Chem. Abstr. 1976, 85, 6388.
17. Middleton, W.J. Org. Synth. 1985, 64, 221.
18. Fujita, M.; Hiyama, T Org. Synth. 1990, 69, 44.
19. Hatanaka, Y.; Hiyama, T J. Org. Chem. 1988, 53, 918.
20. Hatanaka, Y.; Hiyama, T J. Org. Chem. 1989, 54, 268.
21. Damrauer, R.; Danahey, S.E. Organometallics 1986, 5, 1490.
22. Sakurai, H. In Selectivities in Lewis Acid Promoted Reactions, Schinzer, D., Ed.; Kluwer: Dordrecht, 1989, p. 203.
23. Negishi, E. Pure Appl Chem. 1981, 53, 2333.
24. Tamao, K.; Yoshida, J.; Yamamoto, H.; Bcakui, T.; H. Matsumoto, H.; Takahasi, M.; Kurita, A.; Murata, M.; Kumada, M. Organometallics 1982, 1, 355.
25. Tamao, K.; Kobayas W, K.; Ito, Y. Tetrahedron Utt. 1989, 30, 605.
26. Hosomi, A.; Köhra, S.; Tominaga, Y. Chem. Pharm. Bull. 1988, 36, 4622.
27. Hosomi, A.; Köhra, S.; Tominaga, Y. Yuki Gosei Kagaku Kyokai Shi 1989, 47, 83.
28. Hatanaka, Y.; Matsui, K.; Hiyama, T. Tetrahedron Utt. 1989, 30, 2403.
29. Jones, E.R. In The Chemistry of Carbon-Carbon Tiple Bond, Patai, S., Ed.; Wiley: New York, 1978; p. 621.
30. Carpita, A.; Neri, D.; Rossi, R. Gazz. Chim. ltd. 1987 117, 481.
31. Kusumoto, T; Hiyama, T; Takehara, S.; Shoji, T Yuki Gosei Kagaku Kyokai Shi 1991, 49, 475.
32. Poetsch, E. Kontakte, 1988, 2, 15.
33. Sainsbury, M. Tetrahedron 1980, 5(8), 3327.
34. Hatanaka, Y.; Fukushima, S.; Hiyama, T Chem. Lett. 1989, 1771.
35. Hatanaka, Y.; Fukushima, S.; Hiyama, T. Heterocycles 1990, 30. 303.
36. Hatanaka, Y; Hiyama, X Chem. Lett. 1989, 2049.
37. Hatanaka, Y.; Fukushima, S., Hiyama, T. Tetrahedron, in press.
38. Matsumoto, H.; Kasahara, M.; Takahashi, M.; Aral. T.; Nakano, T.; Nagai, Y. J. Organomet. Chem. 1983, 250, 99.
39. Rich, J. D. Organometallics 1989, 2609.
40. Rich, J. D. J. Am. Chem. Soc. 1989, 111, 5886.
41. McManus, S.R; Patterson, J. D. J. Polym. Sci., Polvm. Chem. Ed. 1974, 12, 825.
42. Paulenko, S. Organosilicon Chemistry, Walter de Gruyter: Berlin, 1986.
43. Hoffmann, R.W. Angew. Chem. 1982, 94, 569
44. Angew. Chem. Int. Ed. Engl. 1982, 21, 555.
45. Yamamoto, Y.; Maruyama, K. Heterocylces 1982, 18, 357.
46. Lipshutz, B.H.; Elworthy, TR. J. Org. Chem. 1990.55. 1695.
47. Godschalx, J.; Stille, J.K. Tetrahedron Utt. 1980, 21, 2599.
48. Hatanaka, Y; Ebina, Y.; Hiyama, T. J. Am. Chem. Soc 1991, 113, 7075.
49. Hatanaka, Y; Hiyama, T Tetrahedron Utt. 1987. 28, 4715.
50. Fiandes, V.; Machese, G.; Masolo. G.; Naso. F.; Ronzini. L. Tetrahedron Utt. 1988, 29, 3705.
51. Yamamoto, K.; Ohta, M.; Tsuji, J. Chem. Lett. 1979, 713.
52. Hatanaka, Y; Hiyama, X Tetrahedron Utt. 1988, 29, 97.
53. Hatanaka, Y; Hiyama, X Tetrahedron Utt. 1990, 31, 2719.
54. Stang, P.J.; Hanack, M.; Subramanian, L.R. Synthesis 1992, 85.
55. Scott, W. J.; Crisp, G.T; Stille, J.K. J. Am. Chem. Soc 1984. 106, 4630.
56. Scott, W.J.; Stüle, J.K. Ibid. 1986, 108, 3033.
57. Echavarren, A.M.; Stille, J.K. Ibid. 1987, 109, 5478.
58. Hatanaka, Y; Hiyama, X J. Am. Chem. Soc 1990, 112, 7793.
59. Yamamoto, A. Organotransition Metal Chemistry: Wiley: New York, 1986.
60. Ubadie, J.W.; Stille, J.K. J. Am. Chem. Soc 1983, 105, 669.
61. Bäckvall, J.E.; Akermark, B.J. J. Chem. Soc. Clwm. Commun. 1975, 82.
62. Milstein, D.; Stüle, J.K. J. Am. Chem. Soc 1979, 101, 4981.
63. Abraham, M.H.; Grellier, P.L. In The Chemistry of Metal-bon Bond, Hartley, F.R.; Patai, S. Eds.; Wiley: New York, 1985 Vol 2, Chapter 2.