Reaction of [(Z)-1-bromo-1-alkenyl]dialkylboranes with N-halogeno compound in THF-DMF: A novel synthesis of 1,2-disubstituted (E)-vinyl bromides

Tetrahedron Letters

Volumn 41, Issue 15, 2000, Pages 2595-2598

  Hoshi, Masayuki ^a   Shirakawa, Kazuya ^a  

^a KITAMI INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

1,2 disubstituted (E) vinyl bromides; 1,2 migration; (Z) 1 bromo 1 alkenyl dialkylboranes; DMF; N halogeno compound

Indexed keywords

BORANE DERIVATIVE; BROMINE DERIVATIVE;

ARTICLE; CHEMICAL BINDING; JAPAN; MOLECULAR INTERACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034620945     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00213-6     Document Type: Article

References (19)

1. For example, see: (a) Pelter, A.; Smith, K.; Brown, H. C. In Borane Reagents; Academic: London, 1988.
2. (b) Matteson, D. S. In Stereodirected Synthesis with Organoboranes; Springer: Berlin, 1995.
3. For example, see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
4. (b) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; pp. 49-97.
5. (a) Negishi, E.; Williams, R. M.; Lew, G.; Yoshida, T. J. Organomet. Chem. 1975, 92, C4-C6.
6. (b) Campbell Jr., J. B.; Molander, G. J. Organomet. Chem. 1978, 156, 71-79.
7. (a) Zweifel, G.; Arzoumanian, H. J. Am. Chem. Soc. 1967, 89, 5086-5088.
8. (b) Negishi, E.; Yoshida, T. J. Chem. Soc., Chem. Commun. 1973, 606-607.
9. (c) Arase, A.; Hoshi, M.; Masuda, Y. Bull. Chem. Soc. Jpn. 1984, 57, 209-213.
10. (d) Hoshi, M.; Masuda, Y.; Arase, A. Bull. Chem. Soc. Jpn. 1985, 58, 1683-1689.
11. (e) Brown, H. C.; Basavaiah, D.; Kulkarni, S. U.; Lee, H. D.; Negishi, E.; Katz, J.-J. J. Org. Chem. 1986, 51, 5270-5276.
12. (f) Brown, H. C.; Imai, T.; Bhat, N. G. J. Org. Chem. 1986, 51, 5277-5282.
13. (a) Masuda, Y.; Arase, A.; Suzuki, A. Chem. Lett. 1978, 665-668.
14. (b) Masuda, Y.; Arase, A.; Suzuki, A. Bull. Chem. Soc. Jpn. 1980, 53, 1652-1655.
15. (c) Brown, H. C.; Blue, C. D.; Nelson, D. J.; Bhat, N. G. J. Org. Chem. 1989, 54, 6064-6067.
16. Hoshi, M.; Tanaka, H.; Shirakawa, K.; Arase, A. Chem. Commun. 1999, 627-628.
17. The spectral data of the product 2a were consistent with those reported in Ref. 6.
18. +-79 or 81, 22%), 139 (100), 121 (21), 93 (15), 79 (25), 67 (19), 44 (90), 42 (15).
19. Hoshi, M.; Shirakawa, K., unpublished result.