Palladium-Catalyzed Suzuki-Type Cross-Couplings of lodocyclopropanes with Boronic Acids: Synthesis of trans-1,2-Dicyclopropyl Alkenes

Journal of Organic Chemistry

Volumn 61, Issue 25, 1996, Pages 8718-8719

  Charette, André B ^a   Giroux, André ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000964344     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9614654     Document Type: Article

References (36)

1. (a) Suzuki, A.; Miyaura, N. Chem. Rev. 1995, 95, 2457-2483.
2. (b) Suzuki, A.; Miyaura, N.; Suginome, H. Bull. Chem. Soc. Jpn. 1982, 55, 2221-2223.
3. Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513-519.
4. For examples see:
5. (a) Moreno-Manas, M.; Pajuelo, F.; Pleixats, R. J. Org. Chem. 1995, 60, 2396-2397.
6. (b) Ishiyama, T.; Abe, S.; Miyaura, N.; Suzuki, A. Chem. Lett. 1992, 691-694.
7. Moriya, T.; Furuuchi, T.; Miyaura, N.; Suzuki, A. Tetrahedron 1994, 50, 7961-7968.
8. Miyaura, N.; Maeda, K.; Suginome, H.; Suzuki, A. J. Org. Chem. 1982, 47, 2117-2120.
9. For examples of coupling reactions involving cyclopropanes, see:
10. (a) Corey, E. J.; Eckrich, T. M. Tetrahedron Lett. 1984,25,2415-2418.
11. (b) Hildebrand, J. P.; Marsden, S. P. Synlett 1996, 893-894.
12. Piers, E.; Jean, M.; Marrs, P. S. Tetrahedron Lett. 1987, 28, 5075-5078.
13. For reactivity studies and molecular orbital calculations of cyclopropanes see:
14. (a) Wiberg, K. B. Ace. Chem. Res. 1996, 29, 229-234.
15. (a) Yoshida, M.; Ezaki, M.; Hashimoto, M.; Yamashita, M.; Shigematsu, N.; Okuhara, M.; Kohsaka, M.; Horikoshi, K. J. Antibiot. 1990, 43, 748-754.
16. (b) Kuo, M. S.; Zielinski, R. J.; Cialdella, J. I.; Marschke, C. K.; Dupuis, M. J.; Li, G. P.; Kloosterman, D. A.; Spilman, C. H.; Marshall, V. P. J. Am. Chem. Soc. 1995, 117, 10629-10634.
17. (a) Piers, E.; Jean, M.; Marrs, P. S. Tetrahedron Lett. 1987, 28, 5075-5078.
18. (b) Harada, T.; Katsuhira, T.; Hattori, K.; Oku, A. J. Org. Chem. 1993, 58, 2958-2965.
19. (±)-Iodocyclopropane 1 was prepared by known procedures:
20. (a) Jung, M. E.; Light, L. A. Tetrahedron Lett. 1982, 23, 3851-3854.
21. (b) Piers, E.; Coish, P. D. Synthesis 1995, 47-55.
22. 3; 4. BuLi; 5. catecholborane). See the Supporting Information for details.
23. It was shown previously that the addition of a base greatly facilitates the cross-coupling of organoboron reagents with electrophiles by accelerating the rate of the transmetalation step; for examples, see:
24. (a) Takayuki, O.; Miyaura, N.; Suzuki, A. J Org. Chem. 1993,58, 2201-2208.
25. (b) Suzuki, A. Pure Appl. Chem. 1991, 63, 419-422.
26. The coupling yield drops significantly if the addition of Bu4NC1 is omitted. For a detailed discussion of the cross-coupling catalytic cycle, see:
27. (a) Suzuki, A. Pure Appl. Chem. 1985, 57, 1749-1758.
28. (b) Moreno-Manas, M.; Ferez, M.; Pleixats, R. J. Org. Chem. 1996, 67, 2346-2351 and references cited therein.
29. For the preparation of arylboronic acids see: Thompson, W.; Gaudino, J. J. Org. Chem. 1984, 49, 5237-5243.
30. For examples of cross-coupling studies of o-substituted phenylboronic acids see:
31. (a) Watanabe, T.; Miyaura, N.; Suzuki, A. Synlett 1992,207-210.
32. (b) Anderson, J. C.; Namli, H. Synlett 1995, 765-766.
33. Zhang, H.; Chan, K. S. Tetrahedron Lett. 1996, 7, 1043-1044.
34. Wright, S. W.; Hageman, D. L.; McClure, L. D. J. Org. Chem. 1994, 59, 6095-6097.
35. Minor amounts of thiophene could be detected in the crude NMR of the reaction mixture.
36. Gronowitz, W. J.; Bobosic, V.; Lawitz, K. Chem. Scripta 1984, 23, 120-125.