Preparation of multisubstituted allenes from allylsilanes

Journal of Organic Chemistry

Volumn 70, Issue 10, 2005, Pages 3871-3876

  Ogasawara, Masamichi ^a   Ge, Yonghui ^a   Uetake, Koichi ^a   Fan, Liyan ^a   Takahashi, Tamotsu ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; DERIVATIVES; PROPANE; PYROLYSIS; REACTION KINETICS; SUBSTITUTION REACTIONS;

ALLENES; ALLYLSILANES; BROMOSILANES; NUCLEOPHILES;

SILANES;

1,1 DIBROMO 2 (SILYLMETHYL)CYCLOPROPANE DERIVATIVE; 2 BROMO 1,3 BUTADIENE DERIVATIVE; ALLENE DERIVATIVE; ALLYLSILANE DERIVATIVE; BROMINE DERIVATIVE; BROMODIENE DERIVATIVE; BROMOSILANE DERIVATIVE; CYCLOPROPANE DERIVATIVE; FUNCTIONAL GROUP; METHYL BROMIDE; PALLADIUM; POTASSIUM DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DECOMPOSITION; HEAT TREATMENT; SUBSTITUTION REACTION; SYNTHESIS;

EID: 18744405722     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050142h     Document Type: Article

References (66)

1. (a) Taylor, D. R. Chem. Rev. 1967, 67, 317.
2. (b) Rutledge, T. F. Acetylenes and Allenes; Reinhold: New York, 1969.
3. (c) Patai, S. The Chemistry of Ketenes, Allenes, and Related Compounds; Wiley: Chichester, 1980.
4. (d) Landor, S. R. The Chemistry of the Allenes; Academic Press: London, 1982.
5. (e) Coppola, G. M.; Schuster, H. F. Allenes in Organic Synthesis; Wiley: New York, 1984.
6. (f) Krause, N.; Hashmi, A. S. K. Modern Allene Chemistry; Wiley-VCH: Weinheim, 2004.
7. (g) Pasto, D. J. Tetrahedron 1984, 40, 2805.
8. (h) Marshall, J. A. Chem. Rev. 1996, 96, 31.
9. (i) Wang, K. K. Chem. Rev. 1988, 96, 207.
10. (j) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535.
11. (k) Tius, M. A. Acc. Chem. Res. 2003, 36, 284.
12. (l) Brandsma, L.; Nedolya, N. A. Synthesis 2004, 735.
13. (a) Yamamoto, Y.; Radhakrishnan, U. Chem. Soc. Rev. 1999, 28, 199.
14. (b) Hashmi, A. S. K. Angew. Chem., Int. Ed. 2000, 39, 3590.
15. (c) Zimmer, R.; Dinesh, C. U.; Nandanan, E.; Khan, F. A. Chem. Rev. 2000, 100, 3067.
16. (d) Ma, S.; Li, L. Synlett 2001, 1206.
17. (e) Ma, S. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; p 1491.
18. (f) Ma, S. Acc. Chem. Res. 2003, 36, 701.
19. (g) Ma, S. Eur. J. Org. Chem. 2004, 1175.
20. (a) Sandler, S. R.; Karo, W. Organic Functional Group Preparations, 2nd ed.; Academic Press: Orlando, 1986; Vol. II, p 1.
21. (b) Sydnes, L. K. Chem. Rev. 2003, 103, 1133.
22. (c) Brandsma, L. Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: Oxford, 2004.
23. (d) Miesch, M. Synthesis 2004, 746.
24. (a) Ogasawara, M.; Ikeda, H.; Hayashi, T. Angew. Chem., Int. Ed. 2000, 39, 1042.
25. (b) Ogasawara, M.; Ikeda, H.; Nagano, T.; Hayashi, T. Org. Lett. 2001, 3, 2615.
26. (a) Ogasawara, M.; Ikeda, H.; Nagano, T.; Hayashi, T. J. Am. Chem. Soc. 2001, 123, 2089.
27. (b) Ogasawara, M.; Ueyama, K.; Nagano, T.; Mizuhata, T.; Hayashi, T. Org. Lett. 2003, 5, 217.
28. For recent examples, see: (a) Roush, W. R.; Koyama, K.; Curtin, M. L.; Moriarty, K. J. J. Am. Chem. Soc. 1996, 118, 7502.
29. (b) Tsirk, A.; Gronowitz, S.; Hornfeldt, A. B. Tetrahedron 1998, 54, 9529.
30. (c) Magnus, P.; Westwood, N.; Spyvee, M.; Frost, C.; Linnane, P.; Tavares, F.; Lynch, V. Tetrahedron 1999, 55, 6435.
31. (d) Abe H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2000, 122, 4583.
32. (a) Xu, C.; Negishi, E. Tetrahedron Lett. 1999, 40, 431.
33. (b) Zeng, X.; Hu, Q.; Qian, M.; Negishi, E. J. Am. Chem. Soc. 2003, 125, 13636.
34. (c) Zeng, X.; Qian, M.; Hu, Q.; Negishi, E. Angew. Chem., Int. Ed. 2004, 43, 2259.
35. (a) Roush, W. R.; Moriarty, K. J.; Brown, B. B. Tetrahedron Lett. 1990, 31, 6509.
36. (b) Shen, W.; Wang, L. J. Org. Chem. 1999, 64, 8873.
37. For other reports on preparation of 2-bromo-1,3-dienes, see: (a) Gronowitz, S.; Hallberg, A.; Nikitidis, G. Tetrahedron 1987, 43, 4793.
38. (b) Alper, H.; Vasapollo, G. Tetrahedron Lett. 1989, 30, 2617.
39. (c) Horváth, A.; Bäckvall, J.-E. J. Org. Chem. 2001, 66, 8120.
40. (d) Ma, S.; Wang, G. Tetrahedron Lett. 2002, 43, 5723.
41. (a) Sandler, S. R. J. Org. Chem. 1968, 12, 4537.
42. (b) Weyerstahl, P.; Klamann, D.; Finger, D.; Fligge, M.; Nerdel, F.; Buddrus, J. Chem. Ber. 1968, 101, 1303.
43. (c) Nerdel, F.; Hentschel, P.; Brodowski, W.; Buddrus, J. Liebigs Ann. Chem. 1971, 746, 6.
44. (d) Molchanov, A. P.; Kostikov, R. R. Zh. Org. Khim. 1989, 25, 2533;
45. J. Org. Chem. USSR 1990, 25, 2272.
46. (e) Werstiuk, N. H.; Roy, C. D. Tetrahedron Lett., 2001, 42, 3255 and references therein.
47. For preparation of 2-halo-1,3-butadienes with similar strategy, see: (a) Seyferth, D.; Jula, T. J. Am. Chem. Soc. 1968, 90, 2938.
48. (b) Schlosser, M.; Dahan, R.; Cottens, S. Helv. Chim. Acta 1984, 67, 284.
49. (c) Mitani, M.; Kobayashi, Y.; Koyama, K. J. Chem. Soc., Perkin Trans. 1 1995, 653.
50. (d) Roux, M.; Santelli, M.; Parrain, J.-L. Org. Lett. 2000, 2, 1701.
51. For preparation of allylsilanes used in this study, see: (a) Colvin, W. E. Silicon Reagents in Organic Synthesis; Academic Press: London, 1988; Chapter 5, pp 25-37.
52. (b) Fleming, I.; Pearce, A. J. Chem. Soc., Perkin Trans. 1 1981, 251.
53. (c) Negishi, E.; Luo, F.-T.; Rand, C. L. Tetrahedron Lett. 1982, 23, 27.
54. (d) Narayanan, B. A.; Bunnelle, W. H. Tetrahedron Lett. 1987, 28, 6261.
55. (e) Okamoto, S.; Tani, K.; Sato, F.; Sharpless, K. B.; Zargarian, D. Tetrahedron Lett. 1993, 34, 2509.
56. (f) Denmark, S. E.; Fu, J. Org. Lett. 2002, 4, 1951.
57. (a) Creary, X.; Jiang, Z.; Butchko, M.; McLean, K. Tetrahedron Lett. 1996, 37, 579.
58. (b) Lahrech, M.; Hacini, S.; Parrain, J.-L.; Santelli, M. Tetrahedron Lett. 1997, 38, 3395.
59. (c) Fedorynski, M. Chem. Rev. 2003, 103, 1099.
60. Krijnen, E. S.; Zuilhof, H.; Lodder, G. J. Org. Chem. 1994, 59, 8139.
61. (a) Frey, H. M.; Walsh, R. Chem. Rev. 1969, 69, 103.
62. (b) Curry, M. J.; Stevens, I. D. R. J. Chem. Soc., Perkin Trans, 1 1980, 1756.
63. 4 were reported; see: Ma, S.; Xu, B.; Ni, B. J. Org. Chem. 2000, 65, 8532.
64. Reaction of 1,1-dibromo-2-phenylpropene with a Grignard reagent in the presence of a Ni catalyst was reported; see: Okamoto, Y.; Yoshikawa, Y.; Hayashi, T. J. Organomet. Chem. 1989, 359, 143.
65. dpbp=2,2′-bis(diphenylphosphino)-1,1′-biphenyl. See: Ogasawara, M.; Yoshida, K.; Hayashi, T. Organometallics 2000, 19, 1567 and references cited therein.
66. Nilsen, N. O.; Skattebøl, L.; Baird, M. S.; Buxton, S. R.; Slowey, P. D. Tetrahedron Lett. 1984, 25, 2887.