Copper(I) tert-butoxide-promoted 1,4 Csp-to-O silyl migration: Generation of vinyl copper equivalents and their stereospecific cross-coupling with allylic, aryl, and vinylic halides

Journal of Organic Chemistry

Volumn 67, Issue 24, 2002, Pages 8450-8456

  Taguchi, Haruhiko ^a   Ghoroku, Kazushi ^a   Tadaki, Makoto ^a   Tsubouchi, Akira ^a   Takeda, Takeshi ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLATION;

ALCOHOLS; ALKYLATION; CATALYSTS; HYDROLYSIS; PALLADIUM;

COPPER COMPOUNDS;

ALLYL COMPOUND; COPPER DERIVATIVE; COPPER TERT BUTOXIDE; HALIDE; OXIDE; PALLADIUM; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ALLYLATION; ARTICLE; CATALYST; CONFORMATION; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 0037195768     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo025973r     Document Type: Article

References (70)

1. (a) Hatanaka, Y.; Hiyama, T. Synlett 1991, 845-853.
2. (b) Hiyama, T.; Hatanaka, Y. Pure Appl. Chem. 1994, 66, 1471-1478.
3. (c) Horn, K. H. Chem. Rev. 1995, 95, 1317-1350.
4. (d) Hiyama, T. In Metal-catalyzed Cross-coupling Reactions; Diederich, F.; Stang, P. J., Eds. Organosilicon Compounds in Cross-coupling Reactions; Wiley-VCH: Weinheim, 1998; p 421.
5. (a) Yoshida, J.; Tamao, K.; Yamamoto, H.; Kakui, T.; Uchida, T.; Kumada, M. Organometallics 1982, 1, 542-549.
6. (b) Tamao, K.; Kobayashi, K.; Ito, Y. Tetrahedron Lett. 1989, 30, 6051-6054.
7. (c) Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1989, 54, 268-270.
8. (d) Hatanaka, Y.; Goda, K.; Hiyama, T. J. Organomet. Chem. 1994, 465, 97-100.
9. (e) Mowery, M. E.; Deshong, P. J. Org. Chem. 1999, 64, 1684- 1688.
10. (f) Denmark, S. E.; Wehrli, D. Org. Lett. 2000, 2, 565-568.
11. (g) Denmark, S. E.; Neuville, L. Org. Lett. 2000, 2, 3221-3224.
12. (h) Denmark, S. E.; Pan, W. Org. Lett. 2001, 3, 61-64.
13. (i) Denmark, S. E.; Wang, Z. Org. Lett. 2001, 3, 1073-1076.
14. (j) Denmark, S. E.; Wang, Z. J. Organomet. Chem. 2001, 624, 372-375.
15. (k) Denmark, S. E.; Yang, S.-M. Org. Lett. 2001, 3, 1749-1752.
16. (l) Itami, K.; Nokami, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 5600-5601.
17. (m) Itami, K.; Nokami, T.; Ishimura, Y.; Mitsudo, K.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 11577-11585.
18. (n) Denmark, S. E.; Sweis, R. F. J. Am. Chem. Soc. 2001, 123, 6439-6440.
19. (o) Denmark, S. E.; Yang, S.-M. J. Am. Chem. Soc. 2002, 124, 2102-2103.
20. (p) Hosoi, K.; Nozaki, K.; Hiyama, T. Chem. Lett. 2002, 138-139.
21. (a) Denmark, S. E.; Choi, J. Y. J. Am. Chem. Soc. 1999, 121, 5821-5822.
22. (b) Denmark, S. E.; Wehrli, D.; Choi, J. Y. Org. Lett. 2000, 2, 2491-2494.
23. (c) Denmark, S. E.; Wang, Z. Synthesis 2000, 999-1003.
24. Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1988, 53, 918-920.
25. (a) Yoshida, J.; Tamao, K.; Kakui, T.; Kumada, M. Tetrahedron Lett. 1979, 1141-1144.
26. (b) Urata, H.; Fuchikami, T. Tetrahedron Lett. 1991, 32, 91-94.
27. (c) Lermontov, S. A.; Rakov, I. M.; Zefirov, N. S. Tetrahedron Lett. 1996, 37, 4051-4054.
28. (d) Kang, S.-K.; Kim, T.-H.; Pyun, S.-J. J. Chem. Soc., Perkin Trans. 1 1997, 797-798.
29. (e) Ikegashira, K.; Nishihara, Y.; Hirabayashi, K.; Mori, A.; Hiyama, T. Chem. Commun. 1997, 1039-1040.
30. (f) Ito, H.; Sensui, H.; Arimoto, K.; Miura, K.; Hosomi, A. Chem. Lett. 1997, 639-640.
31. (g) Ito, H.; Arimoto, K.; Sensui, H.; Hosomi, A. Tetrahedron Lett. 1997, 38, 3977-3980.
32. (h) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1998, 39, 4075-4078.
33. (a) Woodbury, R. P.; Rathke, M. W. J. Org. Chem. 1978, 43, 1947-1949.
34. (b) Matsuda, I.; Murata, S.; Ishii, Y. J. Chem. Soc., Perkin Trans. 1 1979, 26-30.
35. (c) Isobe, M.; Kitamura, M.; Goto, T. Tetrahedron Lett. 1979, 3465-3468.
36. (d) Fleming, I.; Floyd, C. D. J. Chem. Soc., Perkin Trans. 1 1981, 969-976.
37. (e) Takeda, T.; Naito, S.; Ando, K.; Fujiwara, T. Bull. Chem. Soc. Jpn. 1983, 56, 967-968.
38. (f) Takeda, T.; Ando, K.; Fujiwara, T. Chem. Lett. 1983, 1285-1288.
39. (g) Brook, A. G.; Chrusciel, J. J. Organometallics 1984, 3, 1317-1381.
40. (h) Isobe, M.; Ichikawa, Y.; Funabashi, Y.; Mio, S.; Goto, T. Tetrahedron 1986, 42, 2863-2872.
41. (i) Tietze, L. F.; Geissler, H.; Gewert, J. A.; Jakobi, U. Synlett 1994, 511-512.
42. (j) Jankowski, P.; Raubo, P.; Wicha, J. Synlett 1994, 985-992.
43. (k) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron 1996, 52, 503-514.
44. (l) Smith, A. B., III; Boldi, A. M. J. Am. Chem. Soc. 1997, 119, 6925-6926.
45. (m) Smith, A. B., III; Pitram, S. M. Org. Lett. 1999, 1, 2001-2004.
46. (n) Bräuer, N.; Michel, T.; Schaumann, E. Tetrahedron 1998, 54, 11481-11488.
47. (o) Moser, W. H. Tetrahedron 2001, 57, 2065-2084.
48. (a) Kim, K. D.; Magriotis, P. A. Tetrahedron Lett. 1990, 31, 6137-6140.
49. (b) Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1995, 60, 4213-4227.
50. Spinazzé, P. G.; Keay, B. A. Tetrahedron Lett. 1989, 30, 1765-1768.
51. Moser, W. H.; Endsley, K. E.; Colyer, J. T. Org. Lett. 2000, 2, 717-719.
52. (a) Takeda, T.; Sugi, S.; Nakayama, A.; Suzuki, Y.; Fujiwara, T. Chem. Lett. 1992, 819-822.
53. (b) Takeda, T.; Kabasawa, Y.; Fujiwara, T. Tetrahedron 1995, 51, 2515-2524.
54. (c) Takeda, T.; Matsunaga, K.; Kabasawa, Y.; Fujiwara, T. Chem. Lett. 1995, 771-772.
55. (d) Takeda, T.; Matsunaga, K.; Uruga, T.; Takakura, M.; Fujiwara, T. Tetrahedron Lett. 1997, 38, 2879-2882.
56. (e) Takeda, T.; Uruga, T.; Gohroku, K.; Fujiwara, T. Chem. Lett. 1999, 821-822.
57. Taguchi, H.; Ghoroku, K.; Tadaki, M.; Tsubouchi, A.; Takeda, T. Org. Lett. 2001, 3, 3811-3814.
58. (a) Sato, F.; Watanabe, H.; Tanaka, Y.; Sato, M. J. Chem. Soc., Chem. Commun. 1982, 1126-1127.
59. (b) Denmark, S. E.; Jones, T. K. J. Org. Chem. 1982, 47, 4595-4597.
60. (c) Murphy, P. J.; Spencer, J. L.; Procter, G. Tetrahedron Lett. 1990, 31, 1051-1054.
61. (d) Takai, K.; Kataoka, Y.; Utimoto, K. J. Org. Chem. 1990, 55, 1707-1708.
62. (e) Rane, A. M.; Vaquer, J.; Colberg, J. C.; Soderquist, J. A. Tetrahedron Lett. 1995, 36, 987-990.
63. (f) Takeuchi, R.; Nitta, S.; Watanabe, D. J. Org. Chem. 1995, 60, 3045-3051.
64. Fujiwara, T.; Sawabe, K.; Takeda, T. Tetrahedron 1997, 53, 8349-8370.
65. Tsuda, T.; Hashimoto, T.; Saegusa, T. J. Am. Chem. Soc. 1972, 94, 658-659.
66. (a) Daves, G. D., Jr.; Hallberg, A. Chem. Rev. 1989, 89, 1433-1445.
67. (b) Hallberg, A.; Westerlund, C. Chem. Lett. 1982, 1993-1994.
68. (c) Karabelas, K.; Hallberg, A. J. Org. Chem. 1989, 54, 1773-1776.
69. (d) Alvisi, D.; Blart, E.; Bonini, B. F.; Mazzanti, G.; Ricci, A.; Zani, P. J. Org. Chem. 1996, 61, 7139-7146.
70. Reich, H. J.; Holtan, R. C.; Bolm, C. J. Am. Chem. Soc. 1990, 112, 5609-5617.