Copper-catalyzed or mediated carbon-carbon bond formation reactions of zirconacycles and alkenylzirconocenes

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 55, Issue 11, 1997, Pages 958-969

  Kotora, Martin ^a   Xi, Zhenfeng ^a   Takahashi, Tamotsu ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041658981     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.55.958     Document Type: Article

References (68)

1. Hegedus, L.S. "Transition Metals in the Synthesis of Complex Organic Molecules"; University Science Books: Mill Valley (1994).
2. a) Fillery, S.F.; Gordon, G.J.; Luker, T.; Whitby, R.J. Pure & Appl. Chem. 1997, 69, 633;
3. b) Taber, D.F.; Wang, Y. J. Am. Chem. Soc. 1997, 119, 22;
4. c) Millward, D.B.; Waymouth, R.M. Organometallics 1997, 16, 1153;
5. d) Negishi, E.; Ma, S.; Sugihara, T.; Noda Y. J. Org. Chem. 1997, 62, 1922;
6. e) Honda, T.; Mori, M. Organometallics 1996, 15, 5464;
7. f) Hicks, F.A.; Buchwald, S.L. J. Am. Chem. Soc. 1996, 118, 11688;
8. f) Suzuki, K.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 1996, 118, 8729;
9. h) Lipshutz, B.H.; Segi, M. Tetrahedron 1995, 51, 4407;
10. i) Fagan, P.J.; Nugent, W.A.; Calabrese, J.C. J. Am. Chem. Soc. 1994, 116, 1880;
11. j) Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124;
12. k) Takai, K.; Yamada, M.; Odaka, H.; Utimoto, K. J. Org. Chem. 1994, 59, 5852.
13. a) Takahashi, T.; Swanson, D.R.; Negishi, E. Chem. Lett. 1987, 623;
14. b) Buchwald, S.L.; Nielsen, R.B. J. Am. Chem. Soc. 1989, 111, 2870;
15. c) Wagenen, B.C.; Livinghouse, T. Tetrahedron Lett. 1989, 30, 3495;
16. d) Takahashi T.; Kageyama, M.; Denisov, V.; Hara, R.; Negishi, E. Tetrahedron Lett. 1993, 34, 687;
17. e) Xi, Z.; Hara, R.; Takahashi, T. J. Org. Chem. 1995, 60, 4444.
18. a) Takahashi, T.; Seki, T.; Nitto, Y.; Saburi, M. J. Am. Chem. Soc. 1991, 113, 6266;
19. b) Suzuki, N.; Kondakov, D.Y.; Takahashi, T. J. Am. Chem. Soc. 1993, 115, 8485;
20. c) Takahashi, T.; Aoyagi, K.; Denisov, V.; Suzuki, N.; Choueiri, D.; Negishi, E. Tetrahedron Lett. 1993, 34, 8301;
21. d) Takahashi, T.; Kondakov, D.Y.; Suzuki, N. Chem. Lett. 1994, 259;
22. e) Dzhemilev, U.M.; Vostrikova, O.S. J. Organomet. Chem. 1985, 285, 43;
23. f) Hoveyda, A.H.; Xu, Z. J. Am. Chem. Soc. 1991, 113, 5079;
24. g) Knight, K.S.; Wang, D.; Waymouth, R.M.; Ziller, J. J. Am. Chem. Soc. 1994, 116, 1845.
25. a) Famili, A.; Farona, M. F.; Thanedar, S. J. Chem. Soc., Chem. Commun. 1983, 435;
26. b) Sikora, D.J.; Rausch, M.P. J. Organomet. Chem. 1984, 276, 21.
27. Reaction with vinylic substrates: a) Takahashi, T.; Kondakov, D.Y.; Xi, Z.; Suzuki, N. J. Am. Chem. Soc. 1995, 117, 5871;
28. b) Takahashi, T.; Xi, Z.; Fischer, R.; Huo, S.; Xi, C.; Nakajima, K. J. Am. Chem. Soc. 1997, 117, 4561;
29. reaction with allylic substrates: c) Takahashi, T.; Suzuki, N.; Kageyama, M.; Kondakov, D.Y.; Hara, R. Tetrahedron Lett. 1993, 34, 4811;
30. d) see ref. 3d;
31. reaction with homoallylic substrates: e) Takahashi, T.; Kondakov, D.Y.; Suzuki, N. Tetrahedron Lett. 1993, 34, 6571;
32. reaction with carbonyl compounds: f) Coperet, C.; Negishi, E.; Takahashi, T. Tetrahedron Lett. 1994, 35, 695;
33. selective functionalization of zirconacyclopentenes: g) Takahashi, T.; Aoyagi, K.; Kondakov, D.Y. J. Chem. Soc., Chem. Commun. 1994, 747;
34. h) Aoyagi, K.; Kasai, K.; Kondakov, D.Y.; Hara, R.; Suzuki, N.; Takahashi, T. Inorg. Chim. Acta 1994, 220, 319;
35. preparation of unsymmetrical zirconacyclopentadienes and their cleavage: i) see ref. 3e;
36. j) Hara, R.; Xi, Z.; Kotora, M.; Takahashi, T. Chem. Lett. 1996, 1003;
37. k) Suzuki, N.; Kondakov, D.Y.; Kageyama, M.; Kotora, M.; Hara, R.; Takahashi, T. Tetrahedron 1995, 51, 4519.
38. Yoshifuji, M.; Loots, M.J.; Schwartz, J. Tetrahedron Lett. 1977, 1303.
39. Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685.
40. Negishi, E.; Cederbaum, F.E.; Takahashi, T. Tetrahedron Lett. 1986, 27, 2829.
41. Takahashi, T.; Kotora, M.; Kasai, K. J. Chem. Soc., Chem. Commun. 1994, 2693.
42. Venanzi, L.M.; Lehman, R.; Keil, R.; Lipshutz, B.H. Tetrahedron Lett. 1992, 33, 5857.
43. Kasai, K.; Kotora, M.; Suzuki, N.; Takahashi, T. J. Chem. Soc., Chem. Commun. 1995, 109.
44. Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 4183.
45. Takahashi, T.; Kotora, M.; Xi, Z. J. Chem. Soc., Chem. Commun. 1995, 1503.
46. Takahashi, T.; Xi, Z.; Kotora, M.; Xi, C.; Nakajima, K. Tetrahedron Lett. 1996, 37, 7521.
47. a) Schore, N.E. Chem. Rev. 1988, 88, 1081;
48. b) Schore, N.E. in "Comprehensive Organic Synthesis", Eds. Trost, B.M.; Fleming, I.; Paquette, L.A.; Pergamon: Tokyo (1991), vol. 5, p. 1144;
49. c) Grotjahn, D.B. in "Comprehensive Organometallic Chemistry II", Eds. Abel, E.W.; Stone, F.G.A.; Wilkinson, G.; Pergamon: Oxford (1995), vol.12, p. 747;
50. d) Vollhardt, K.P.C. Angew. Chem. Int. Ed. Engl. 1984, 23, 539.
51. Wakatsuki, Y.; Kuramitsu, T.; Yamazaki, H. Tetrahedron Lett. 1974, 4549.
52. Takahashi, T.; Kotora, M.; Xi, Z. J. Chem. Soc., Chem. Commun. 1995, 361.
53. Takahashi, T.; Hara, R.; Nishihara, Y.; Kotora, M. J. Am. Chem. Soc. 1996, 118, 5154.
54. a) Labinger, J.A. in "Comprehensive Organic Synthesis"; Eds. Trost, B.M.; Fleming, I.; Paquette, L.A.; Pergamon Press: Oxford (1991), vol. 3, p. 667;
55. b) Hart, D.W.; Blackburn, T.F.; Schwartz, J. J. Am. Chem. Soc. 1975, 97, 679.
56. Takahashi, T.; Kotora, M.; Fisher, R.; Nishihara, Y.; Nakajima, K. J. Am. Chem. Soc. 1995, 117, 11039.
57. a) Williams, G.M.; Gell, K.I.; Schwartz, J. J. Am. Chem. Soc. 1980, 102, 3660;
58. b) Cell, K.I.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 2867;
59. c) Demerseman, B.; Buquet, G.; Bigorne, M.J. J. Organomet. Chem. 1977, 132, 223.
60. Gell, K.I.; Schwartz, J. Inorg. Chem. 1980, 19, 3207.
61. a) Kreutzer, K.A.; Fischer, R.A.; Davis, W.A.; Spaltenstein, E.; Buchwald, S.L. Organometallics 1991, 10, 4031;
62. b) Takahashi, T.; Hasegawa, M.; Saburi, M.; Roussel, C.J.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 8564.
63. a) Rousset, C.J.; Swanson, D.R.; Lamaty, F.; Negishi, E. Tetrahedron Lett. 1989, 30, 5105;
64. b) Ito, H.; Taguchi, T.; Hanzawa, Y. Tetrahedron Lett. 1992, 33, 1295.
65. Xi, C.; Huo, S.; Affifi, H.T.; Hara, R.; Takahashi, T. Tetrahedron Lett. 1997, 38, 4099.
66. Hara, R.; Nishihara, Y.; Drognat Landre, P.; Takahashi, T. Tetrahedron Lett. 1997, 38, 447.
67. Hara, R.; Liu, Y.; Sun, W.H.; Takahashi, T. Tetrahedron Lett. 1997, 38, 4103.
68. Takahashi, T.; Nishihara, Y.; Hara, R.; Huo, S.; Kotora, M. J. Chem. Soc., Chem. Commun. 1997, in press.