π-Allylpalladium-mediated catalytic synthesis of functionalized allenes

Angewandte Chemie - International Edition

Volumn 39, Issue 6, 2000, Pages 1042-1044

  Ogasawara, Masamichi ^a   Ikeda, Hisashi ^a   Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Allenes; Allyl complexes; Cross coupling; Nucleophiles; Palladium

Indexed keywords

ALLENE DERIVATIVE; ALLYL COMPOUND; PALLADIUM;

ARTICLE; CATALYSIS; COMPLEX FORMATION; METHODOLOGY; REACTION ANALYSIS; SYNTHESIS;

EID: 0034677693     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000317)39:6<1042::AID-ANIE1042>3.0.CO;2-7     Document Type: Article

References (27)

1. a) D. R. Taylor, Chem. Rev. 1967, 67, 317;
2. b) The Chemistry of the Allenes (Ed.: S. R. Landor), Academic Press, London, 1982;
3. c) G. M. Coppola, H. F. Schuster, Allenes in Organic Synthesis, Wiley, New York, 1984;
4. d) D. J. Pasto, Tetrahedron 1984, 40, 2805.
5. a) S. R. Randler, W. Karo, Organic Functional Group Preparations, 2nd ed., Vol. II, Academic Press, Orland, 1986, p. 1;
6. b) For a recent example, see A. G. Myers, B. Zheng, J. Am. Chem. Soc. 1996, 118, 4492.
7. a) S. L. Buchwald, R. H. Grubbs, J. Am. Chem. Soc. 1983, 105, 5490;
8. b) K. M. Brummond, E. A. Dingess, J. L. Kent, J. Org. Chem. 1996, 61, 6096;
9. c) N. A. Petasis, Y.-H. Hu, J. Org. Chem. 1997, 62, 782;
10. d) Y. Nagaoka, K. Tomioka, J. Org. Chem. 1998, 63, 6428;
11. e) B. Delouvrié, E. Lacôte, L. Fensterbank, M. Malacria, Tetrahedron Lett. 1999, 40, 3565.
12. For a review on π-allylpalladium-mediated catalytic allylic substitutions, see J. Tsuji, Palladium Reagents and Catalysts, Wiley, Chichester, 1995, p. 290.
13. a) D. Djahanbini, B. Cazes, J. Gore, Tetrahedron Lett. 1984, 25, 203;
14. b) D. Djahanbini, B. Cazes, J. Gore, Tetrahedron 1987, 43, 3441.
15. For recent examples of transition metal catalyzed allene synthesis, see a) Y. Matsumoto, M. Naito, T. Hayashi, Organometallics 1992, 11, 2732;
16. b) S. Ogoshi, S. Nishiguchi, K. Tsutsumi, H. Kurosawa, J. Org. Chem. 1995, 60, 4650;
17. c) S. J. Sturla, N. M. Kablaoui, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 1976.
18. The starting 1,1-dibromo-1-alkenes were easily prepared from the corresponding aldehydes by standard procedures: a) F. Ramirez, N. B. Desai, N. McKelvie, J. Am. Chem. Soc. 1962, 84, 1745;
19. b) E. J. Corey, P. L. Fuchs, Tetrahedron Lett. 1972, 36, 3769.
20. Palladium-catalyzed selective substitutions of one of the two halides from 1,1-dihalo-1-alkene have been reported: a) A. Minato, K. Suzuki, K. Tamao, J. Am. Chem. Soc. 1987, 109, 1257;
21. b) J. Uenishi, R. Kawahama, O. Yonemitsu, J. Tsuji, J. Org. Chem. 1996, 61, 5716;
22. c) J. Uenishi, R. Kawahama, Y. Shiga, O. Yonemitsu, J. Tsuji, Tetrahedron Lett. 1996, 37, 6759.
23. The abbreviations of phosphanes: dppe = 1,2-bis(diphenylphosphanyl)ethane, dppp = 1,3-bis(diphenylphosphanyl)propane, dppb = 1,4-bis(diphenylphosphanyl)butane, dppf = 1,1′-bis(diphenylphosphanyl)(ferrocene, dpbp = 2,2′-bis(diphenylphosphanyl)-1,1′-biphenyl.
24. H. Kleijn, H. Westmijze, J. Meijer, P. Vermeer, Recl. Trav. Chim. Pays-Bas 1983, 102, 378.
25. 3-butadienyl" for the ligand in the palladium complexes described here.
26. 4]. M. Brookhart, B. Grant, A. F. Volper, Jr., Organometallics 1992, 11, 3920.
27. E. S. Krijnen, H. Zuihof, G. Lodder, J. Org. Chem. 1994, 59, 8139.