Palladium(0)-catalyzed cope rearrangement of acyclic 1,5-dienes. Bis(π- allyl)palladium(II) intermediate [12]

Journal of the American Chemical Society

Volumn 121, Issue 46, 1999, Pages 10850-10851

  Nakamura, Hiroyuki ^a   Iwama, Hideki ^a   Ito, Masateru ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKENE; PALLADIUM;

CATALYSIS; CHEMICAL REACTION KINETICS; ISOMERISM; KINETICS; LETTER; NONHUMAN; SYNTHESIS; THERMODYNAMICS;

EID: 0033601118     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992117x     Document Type: Letter

References (33)

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16. Catalytic insertion of rhodium complexes into the C-C bond activated by the strained system: (a) Murakami, M.; Amii, H.; Ito, Y. Nature 1994, 370, 540. (b) Murakami, M.; Amii, H.; Shigeto, K.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 8285. (c) Murakami, M.; Takahashi, K.; Amii, H.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 9307 . Activated by the adjacent carbonyl group: (d) Jun, C.-H.; Lee, H. J. Am. Chem. Soc. 1999, 121, 880.
17. Catalytic insertion of rhodium complexes into the C-C bond activated by the strained system: (a) Murakami, M.; Amii, H.; Ito, Y. Nature 1994, 370, 540. (b) Murakami, M.; Amii, H.; Shigeto, K.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 8285. (c) Murakami, M.; Takahashi, K.; Amii, H.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 9307 . Activated by the adjacent carbonyl group: (d) Jun, C.-H.; Lee, H. J. Am. Chem. Soc. 1999, 121, 880.
18. Catalytic insertion of rhodium complexes into the C-C bond activated by the strained system: (a) Murakami, M.; Amii, H.; Ito, Y. Nature 1994, 370, 540. (b) Murakami, M.; Amii, H.; Shigeto, K.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 8285. (c) Murakami, M.; Takahashi, K.; Amii, H.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 9307 . Activated by the adjacent carbonyl group: (d) Jun, C.-H.; Lee, H. J. Am. Chem. Soc. 1999, 121, 880.
19. Catalytic insertion of palladium complexes into the C-C bond activated by the strained system: (a) Edelbach, B. L.; Lachicotte, R. J.; Jones, W. D. J. Am. Chem. Soc. 1998, 120, 2843. Activated by the functionalized system: (b) Nilsson, Y. I. M.; Andersson, P. G.; Bäckvall, J.-E. J. Am. Chem. Soc. 1993, 115, 6609. (c) Vicart, N.; Goré, J.; Cazes, B. SYNLETT 1996, 850. (d) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1998, 120, 70. (e) Nozaki, K.; Sato, N.; Takaya, H. J. Org. Chem. 1994, 59, 2679.
20. Catalytic insertion of palladium complexes into the C-C bond activated by the strained system: (a) Edelbach, B. L.; Lachicotte, R. J.; Jones, W. D. J. Am. Chem. Soc. 1998, 120, 2843. Activated by the functionalized system: (b) Nilsson, Y. I. M.; Andersson, P. G.; Bäckvall, J.-E. J. Am. Chem. Soc. 1993, 115, 6609. (c) Vicart, N.; Goré, J.; Cazes, B. SYNLETT 1996, 850. (d) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1998, 120, 70. (e) Nozaki, K.; Sato, N.; Takaya, H. J. Org. Chem. 1994, 59, 2679.
21. Catalytic insertion of palladium complexes into the C-C bond activated by the strained system: (a) Edelbach, B. L.; Lachicotte, R. J.; Jones, W. D. J. Am. Chem. Soc. 1998, 120, 2843. Activated by the functionalized system: (b) Nilsson, Y. I. M.; Andersson, P. G.; Bäckvall, J.-E. J. Am. Chem. Soc. 1993, 115, 6609. (c) Vicart, N.; Goré, J.; Cazes, B. SYNLETT 1996, 850. (d) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1998, 120, 70. (e) Nozaki, K.; Sato, N.; Takaya, H. J. Org. Chem. 1994, 59, 2679.
22. Catalytic insertion of palladium complexes into the C-C bond activated by the strained system: (a) Edelbach, B. L.; Lachicotte, R. J.; Jones, W. D. J. Am. Chem. Soc. 1998, 120, 2843. Activated by the functionalized system: (b) Nilsson, Y. I. M.; Andersson, P. G.; Bäckvall, J.-E. J. Am. Chem. Soc. 1993, 115, 6609. (c) Vicart, N.; Goré, J.; Cazes, B. SYNLETT 1996, 850. (d) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1998, 120, 70. (e) Nozaki, K.; Sato, N.; Takaya, H. J. Org. Chem. 1994, 59, 2679.
23. Catalytic insertion of palladium complexes into the C-C bond activated by the strained system: (a) Edelbach, B. L.; Lachicotte, R. J.; Jones, W. D. J. Am. Chem. Soc. 1998, 120, 2843. Activated by the functionalized system: (b) Nilsson, Y. I. M.; Andersson, P. G.; Bäckvall, J.-E. J. Am. Chem. Soc. 1993, 115, 6609. (c) Vicart, N.; Goré, J.; Cazes, B. SYNLETT 1996, 850. (d) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1998, 120, 70. (e) Nozaki, K.; Sato, N.; Takaya, H. J. Org. Chem. 1994, 59, 2679.
24. Nakamura, H.; Sekido, M.; Ito, M.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 6838.
25. The activated olefin, whose two substituants at the β-position were H and pentyl, underwent the proton absorption at the γ-position followed by allylation at the α-position to give 4,4-dicyano-1,5-decadiene.
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28. However, this possibility seems to be very small.
29. The 1,5-heptadiene derivatives 5 were synthesized from the reaction of 1a with crotyl ethyl carbonate in the presence of palladium(0) catalyst.
30. In this case, the starting material 5a was recovered in 32% yield. However, in other cases, the starting materials 5b-e were consumed completely after 3 h. The reaction at lower temperatures (50-70°C) was sluggish.
31. It is thought that the fragment leading to the formation of 1a,h,c,i would be volatile butene, although we did not intend to confirm the formation of it.
32. We tested 2-substituted 3-cyano-3-ethoxycarbonyl- and 3,3-diethoxy-carbonyl-1,5-heptadienes under similar reaction conditions, but the starting materials were recovered.
33. Recently we have found that a bis-π-allylpalladium complex has nucleophilic character and reacts with aldehydes and imines very smoothly: Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641.