Cobalt-catalyzed intramolecular Heck-type reaction of 6-halo-1-hexene derivatives

Organic Letters

Volumn 4, Issue 13, 2002, Pages 2257-2259

  Fujioka, Takuma ^a   Nakamura, Tomoaki ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

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EID: 0011775380     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0261128     Document Type: Article

References (21)

1. (a) Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581.
2. (b) Heck, R. F.; Nolley, Jr., J. P. J. Org. Chem. 1972, 37, 2320-2322.
3. (a) Bräse, S.; de Meijere, A. In Metal-catalyzed Cross-coupling Reactions, Diederich, F.; Stang, P. J. Ed., Wiley-VCH: Weinheim, 1998; Chapter 3.
4. (b) Link, J. T.; Overman, L. E. In Metal-catalyzed Cross-coupling Reactions, Diederich, F.; Stang, P. J. Ed., Wiley-VCH: Weinheim, 1998; Chapter 6.
5. (c) Heck, R. F. Org. React. 1982, 27, 345-390.
6. (d) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066.
7. (e) Beller, M.; Riermeier, T. H.; Stark, G. In Transition Metals for Organic Synthesis; Beller, M.: Bolm, C., Ed., Wiley-VCH: Weinheim, 1998; Volume 1, Chapter 2.13.
8. (f) Nicolaou, K. C.; Sorensen, E. J. Classics in Total Synthesis; VCH: New York, 1996; Chapter 31.
9. 3-hybridized was reported. However, in most cases, there are no hydrogens that are involved in β-hydride elimination. See ref 2f. An exception was the following: Oppolzer, W.; De Vita, R. J. J. Org. Chem. 1991, 56, 6256-6257.
10. (a) Pattenden, G. Chem. Soc. Rev. 1988, 17, 361-382.
11. (b) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519-564. Tada, M. J. Synth. Org. Chem. Jpn. 1998, 56, 544-556.
12. (a) Pattenden, G. Chem. Soc. Rev. 1988, 17, 361-382.
13. Cobaloxime-catalyzed intermolecular Heck-type reaction was reported: Branchaud, B. P.; Detlefsen, W. D. Tetrahedron Lett. 1991, 32, 6273-6276.
14. Sodium telluride-induced reaction was reported: Bell, W.; McQueen, E. D.; Walton, J. C.; Foster, D. F.; Cole-Hamilton, D. J.; Hails, J. E. J. Cryst. Growth 1992, 117, 58-66.
15. Ikeda, Y.; Nakamura, T.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2002, 124, ASAP (JA026296L).
16. DPPPEN = 1,5-bis(diphenylphosphino)pentane. DPPH = 1.6-bis-(diphenylphosphino)hexane.
17. Wakabayashi, K.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 5374-5375.
18. For example, Larock reported palladium-catalyzed cyclization reaction of 5 leading to isopropyl-substituted benzofuran. Larock, R. C.; Stinn, D. E. Tetrahedron Lett. 1988, 29, 4687-4690.
19. Manganese-and iron-catalyzed similar conversions were reported: (a) Inoue, R.; Nakao, J.; Shinokubo, H.; Oshima, K. Bull. Chem. Soc. Jpn. 1997, 70, 2039-2049.
20. (b) Nakao, J.; Inoue, R.; Shinokubo, H.; Oshima, K. J. Org. Chem. 1997, 62, 1910-1911.
21. (c) Hayashi, Y.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1998, 39, 63-66.