Palladium-catalyzed preparation of vinylallenes from 2-bromo-1,3,5-trienes via an alkylidene-π-allylpalladium-mediated formal SN2″ pathway

Organic Letters

Volumn 8, Issue 23, 2006, Pages 5409-5412

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

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

ALKADIENES; CATALYSIS; MOLECULAR STRUCTURE; PALLADIUM;

EID: 33845269741     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062309e     Document Type: Article

References (48)

1. (a) Negishi, E., Ed. Handbook of Organopalladium Chemistry for Organic Synthesis; John Wiley and Sons: New York, 2002; p 1663.
2. (b) Tsuji, J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century; John Wiley and Sons: Chichester, 2004; p 431.
3. (a) Ogasawara, M.; Ikeda, H.; Hayashi, T. Angew. Chem., Int. Ed. 2000, 39, 1042.
4. (b) Ogasawara, M.; Ikeda, H.; Nagano, T.; Hayashi, T. J. Am. Chem. Soc. 2001, 123, 2089.
5. (c) Ogasawara, M.; Ueyama, K.; Nagano, T.; Mizuhata, Y.; Hayashi, T. Org. Lett. 2003, 5, 217.
6. (d) Ogasawara, M.; Ge, Y.; Uetake, K.; Fan, L.; Takahashi, T. J. Org. Chem. 2005, 70, 3871.
7. (e) Ogasawara, M.; Nagano, T.; Hayashi, T. J. Org. Chem. 2005, 70, 5764.
8. (f) Ogasawara, M.; Ge, Y.; Uetake, K.; Takahashi, T. Org. Lett. 2005, 7, 5697.
9. (a) Zeng, X.; Hu, Q.; Qian, M.; Negishi, E. J. Am. Chem. Soc. 2003, 125, 13636.
10. (b) Zeng, X.; Qian, M.; Hu, Q.; Negishi, E. Angew. Chem., Int. Ed. 2004, 43, 2259.
11. For examples of Pd-catalyzed reactions involving alkylidene-π- allylpalladium intermediates, see: (a) Kleijn, H.; Westmijze, H.; Meijer, J.; Vermeer, P. Recl. Trav. Chim. Pays-Bas 1983, 102, 378.
12. (b) Djahanbini, D.; Cazes, B.; Gore, J. Tetrahedron Lett. 1984, 25, 203.
13. (c) Djahanbini, D.; Cazes, B.; Gore, J. Tetrahedron 1985, 41, 867.
14. (d) Djahanbini, D.; Cazes, B.; Gore, J. Tetrahedron 1987, 43, 3441.
15. (e) Trost, B. M.; Tour, J. M. J. Org. Chem. 1989, 54, 484.
16. (f) Nokami, J.; Maihara, A.; Tsuji, J. Tetrahedron Lett. 1990, 31, 5629.
17. (g) Piotti, M. E.; Alper, H. J. Org. Chem. 1994, 59, 1956.
18. (h) Imada, Y.; Vasapollo, G.; Alper, H. J. Org. Chem. 1996, 61, 7982.
19. (i) Imada, Y.; Ueno, K.; Kutsuwa, K.; Murahashi, S. Chem. Lett. 2002, 140.
20. (j) Trost, B. M.; Fandrick, D. R.; Dinh, D. C. J. Am. Chem. Soc. 2005, 127, 14186.
21. (k) Imada, Y.; Nishida, M.; Kutsuwa, K.; Murahashi, S.; Naota, T. Org. Lett. 2005, 7, 5837.
22. Benyunes, S. A.; Brandt, L.; Fries, A.; Green, M.; Mahon, M. F.; Papworth, T. M. T. J. Chem. Soc., Dalton Trans. 1993, 3785.
23. Theoretical studies on closely related systems suggested that a σ-(allenylmethyl)palladium species is less stable than an alkylidene-π-allylpalladium and an σ-(1,3-dien-2-yl)palladium. See: Bigot, B.; Delbecq, F. New J. Chem. 1990, 14, 659.
24. For an analogous example of nickel species, see: Karlström, A. S. E.; Itami, K.; Bäckvall, J.-E. J. Org. Chem. 1999, 64, 1745.
25. N2′ substitutions, see: (a) Trost, B. M.; Hung, M.-H. J. Am. Chem. Soc. 1984, 106, 6837.
26. (b) Trost, B. M.; Urch, C. J.; Hung, M.-H. Tetrahedron Lett. 1986, 27, 4949.
27. (c) Andersson, P. G.; Bäckvall, J.-E. J. Org. Chem. 1991, 56, 5349.
28. (d) Nilsson, Y. I. M.; Andersson, P. G.; Bäckvall, J.-E. J. Am. Chem. Soc. 1993, 115, 6609.
29. (e) Trost, B. M.; Bunt, R. C. Tetrahedron Lett. 1993, 34, 7513.
30. (f) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1998, 120, 70.
31. dpbp = 2,2′-bis(diphenylphosphino)-1,1′-biphenyl. See: Ogasawara, M.; Yoshida, K.; Hayahshi, T. Organometallics 2000, 19, 1567 and references therein.
32. (a) Åkermark, B.; Hansson, S.; Krakenberger, B.; Vitagliano, A.; Zetterberg, K. Organometallics 1984, 3, 679.
33. (b) Keinan, e.; Saha, M. J. Chem. Soc., Chem. Commun. 1984, 648.
34. (c) Frost, C. G.; Howarth, J.; Williams, J. M. Tetrahedron: Asymmetry 1992, 3, 1089.
35. (a) de Graaf, W.; Boersma, J.; van Koten, G.; Elsevier, C. J. J. Organomet. Chem. 1989, 378, 115.
36. (b) Matsumoto, Y.; Naito, M.; Uozumi, Y.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1993, 1468.
37. (c) Tillack, A.; Michalik, D.; Koy, C.; Michalik, M. Tetrahedron Lett. 1999, 40, 6567.
38. (d) Tillack, A.; Koy, C.; Michalik, D.; Fischer, C. J. Organomet. Chem. 2000, 603, 116.
39. (e) Han, J. W.; Tokunaga, N.; Hayashi, T. J. Am. Chem. Soc. 2001, 123, 12915.
40. (f) Hayashi, T.; Tokunaga, N.; Inoue, K. Org. Lett. 2004, 6, 305.
41. For transition-metal-catalyzed kinetic resolutions of racemic chiral allenes, see: (a) Noguchi, Y.; Takiyama, H.; Katsuki, T. Synlett 1998, 543.
42. (b) Sweeney, Z. K.; Salsman, J. L.; Andersen, R. A.; Bergman, R. G. Angew. Chem., Int. Ed. 2000, 39, 2339.
43. For relevant reviews on the asymmetric synthesis of allenes: (a) Hoffmann-Röder, A.; Krause, N. Angew. Chem., Int. Ed. 2002, 41, 2933.
44. (b) Ohno, H.; Nagaoka, Y.; Tomioka, K. In Modern Allene Chemistry; Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2004; p 141.
45. The absolute configuration of 3an was deduced by the Lowe-Brewster rule. See: (a) Lowe, G. Chem. Commun. 1965, 411.
46. (b) Brewster, J. H. Top. Stereochem. 1967, 2, 1.
47. Saito, T.; Yokozawa, T.; Ishizaki, T.; Moroi, T.; Sayo, N.; Miura, T.; Kumobayashi, H. Adv. Synth. Catal. 2001, 343, 264.
48. For an example of preparing enantiomerically enriched vinylallenes, see: Molander, G. A.; Sommers, E. M.; Baker, S. R. J. Org. Chem. 2006, 71, 1563.