Palladium-catalyzed stereoselective hydrogenolysis of conjugated 1,1-dibromo-1-alkenes to (Z)-1-bromo-1-alkenes. An application to stepwise and one-pot synthesis of enediynes and dienynes

Journal of Organic Chemistry

Volumn 61, Issue 17, 1996, Pages 5716-5717

  Uenishi, Jun'ichi ^a   Kawahama, Reiko ^a   Yonemitsu, Osamu ^a   Tsuji, Jiro ^b  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

^b KURASHIKI UNIVERSITY OF SCIENCE AND THE ARTS   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001683443     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961013r     Document Type: Article

References (32)

1. (a) Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons Ltd.: New York, 1995.
2. (a) Knight, D. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, p 481.
3. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
4. (c) Stille, J. K. Angew. Chem. Int. Ed. Engl. 1986, 25, 508.
5. (d) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, p 521.
6. Balogh-Nair, V.; Nakanishi, K. In Method in Enzymalogy; Packer, L. Ed.; Academic Press: New York, 1982; Vol. 88.
7. Nicolaou, K. C.; Ramphal, J. Y.; Petasis, N. A.; Serhan, C. N. Angew. Chem. Int. Ed. Engl. 1991, 30, 1100.
8. (a) Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 61, 16.
9. (b) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453.
10. (c) Wang, K. K. Chem. Rev. 1996, 96, 207.
11. (d) Maier, M. E. Synlett. 1995, 13.
12. (a) Nicolaou, K. C.; Maligres, P.; Suzuki, T.; Wendeborn, S. V.; Dai, W.-M.; Chadha, R. K. J. Am. Chem. Soc. 1992, 114, 8890.
13. (b) Magnus, P.; Carter, P.; Elliott, J.; Lewis, R.; Harlin, J.; Pitterna, T.; Bauta, W. E.; Fortt, S. J. Am. Chem. Soc. 1992, 114, 2544.
14. (a) Kluge, A. F.; Untch, K. G.; Fried, J. H. J. Am. Chem. Soc. 1972, 94, 9256.
15. (b) Miller, R. B.; McGarvey, G. J. Org. Chem. 1978, 43, 4424.
16. (c) Brown, H. C.; Hamaoka, T.; Ravindran, N. J. Am. Chem. Soc. 1973, 95, 6456.
17. Although some (Z)-1-halo-1,3-dienes have been prepared, the geometrical purities were not satisfactory, (a) Bestmann, H. J.; Rippel, H. C.; Dostalek, R. Tetrahedron Lett. 1989, 30, 5261. (b) Matsumoto, M.; Kuroda, K. Tetrahedron Lett. 1980, 21, 4021.
18. Although some (Z)-1-halo-1,3-dienes have been prepared, the geometrical purities were not satisfactory, (a) Bestmann, H. J.; Rippel, H. C.; Dostalek, R. Tetrahedron Lett. 1989, 30, 5261. (b) Matsumoto, M.; Kuroda, K. Tetrahedron Lett. 1980, 21, 4021.
19. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467. Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313.
20. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467. Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313.
21. Ramirez, F.; Desai, N. B.; McKelvie, N. J. Am. Chem. Soc. 1962, 84, 1745. The conjugated 1,1-dibromoalkenes were obtained in 60- 95% yields.
22. 3SnH (1.05-1.1 mmol) in benzene (3 mL), and the mixture was stirrred for 15-60 min at room temperature. Although (Z)-1-bromoalkene was isolated at this stage, the successive coupling reaction with alkyne was carried out. To the reaction mixture were added alkyne (1.5 mmol), CuI (30 mol %), and diisopropylamine (6 mmol), and the reaction was conducted at room temperature for 15-60 min.
23. The (E)-isomer could not be detected by NMR in the crude mixture. The Pd-catalyzed hydrogenolysis of simple 1-iodo-1-alkenes was reported by Utimoto et al. Although it was highly stereospecific, the reaction of 1-bromo-1-alkenes was reported to be sluggish (see: Taniguchi, M.; Takeyama, Y.; Fugami, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 2593).
24. The hydrogenolysis of simple 1,1-dibromo-1-alkenes also worked well.
25. Other reducing reagents such as triethylsilane, tris(trimethylsilyl)silane, and formic acid were ineffective.
26. 3SnH) gave complex mixtures including (E)- and (Z)-isomers.
27. For differentiation of the two bromo groups of the 1,1-dibromo- 1-alkene, a successful Suzuki coupling was reported by Roush et al. (see: Roush, W. R.; Brown, B. B.; Drozda, S. E. Tetrahedron Lett. 1988, 29, 3541).
28. For the typical Suzuki conditions, see: Organic Syntheses; Wiley: New York, 1993; Collect. Vol. 8, 532.
29. The Heck reaction of 2a with methyl acrylate gave the corresponding (E,E,E)-trienecarboxylate under the improved conditions of Jeffrey (see: Jeffery, T. Tetrahedron Lett. 1985, 26, 2667).
30. The bromo dienes and enynes gradually decompose, even when kept in a deep freezer. However, they were reasonably stable in the presence of triphenylphosphine.
31. A terminal diene was formed as a serious byproduct in 30-40% yields under the one-pot conditions.
32. The stepwise yields were 63% (2f to 5a), 86% (2f to 5b), and 90% (2f to 5c).