Simple and efficient protocol for the synthesis of functionalized styrenes from 1,2-dibromoethane and arylboronic acids

Organic Letters

Volumn 5, Issue 16, 2003, Pages 2891-2894

  Lando, Vanusa R ^a   Monteiro, Adriano L ^a  

^a FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DIBROMOETHANE; BORONIC ACID DERIVATIVE; ETHYLENE; ORGANOMETALLIC COMPOUND; STYRENE DERIVATIVE;

ARTICLE; BIOAVAILABILITY; CATALYSIS; CROSS REACTION; DRUG SYNTHESIS;

EID: 0141520521     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034948k     Document Type: Article

References (27)

1. (a) Hirao, A.; Loykulnant, S.; Ishizone, T. Prog. Polym. Sci. 2002, 22, 1399.
2. (b) Kamisnky, W.; Laban, A. Appl. Catal. 2001, 222, 47.
3. (c) de Vries, J. G. Can. J. Chem. 2001, 79, 1086.
4. (d) Furstner, A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990.
5. (e) Fassina, V.; Ramminger, C.; Seferin, M.; Monteiro, A. L. Tetrahedron 2000, 56, 7403.
6. (f) Ramminger, C.; Zim, D.; Lando, V. R.; Fassina, V.; Monteiro, A. L. J. Braz. Chem. Soc. 2000, 11, 105.
7. Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds; VCH: Weinheim, 1998.
8. Plevyak, J. E.; Heck, R. F. J. Org. Chem. 1978, 43, 2454.
9. McKean, D. R.; Parrinello, G.; Renaldo, A. F.; Stille, J. K. J. Org. Chem. 1987, 52, 422.
10. (a) Adams, D. R.; Duncton, M. A. J.; Roffey, J. R. A.; Spencer, J. Tetrahedron Lett. 2002, 43, 7581.
11. (a) Bumagin, N. A.; Luzikova, E. V. J. Organomet. Chem. 1997, 532, 271.
12. Jeffery, T. Tetrahedron Lett. 1999, 40, 1673.
13. (a) Denmark, S. E.; Wang, Z. Synthesis 2000, 999.
14. (b) Denmark, S. E.; Wang, Z. J. Organomet. Chem. 2001, 624, 372.
15. Hunt, A. R.; Stewart, S. K.; Whiting, A. Tetrahedron Lett. 1993, 34, 3599.
16. Kerins, F.; O'Shea, D. F. J. Org. Chem. 2002, 67, 4968.
17. Molander, G. A.; Bernardi, C. R. J. Org. Chem. 2002, 67, 8424.
18. Gaseous vinyl bromide has been used in the reaction with aryl Grignard reagents to produce styrenes: Kharasch, M. S.; Fuchs, C. F. J. Am. Chem. Soc. 1943, 65, 504.
19. 4, filtered, and concentrated in vacuo, and then the crude material was purified by flash chromatography on silica gel.
20. (a) Weiss, H.; Milstein, D. Chem. Commun. 1999, 1901.
21. (b) Bohm, V. P. W.; Hermann, W. A. Chem. Eur. J. 2001, 7, 4191.
22. (c) Consorti, C. S.; Zanini, M. L.; Leal, S.; Eberling, G.; Dupont, J. Org. Lett. 2003, 5, 983.
23. Zim, D.; Gruber, A. S.; Ebeling, G.; Dupont, J.; Monteiro, A. L. Org. Lett. 2000, 2, 2881.
24. Saito, S.; Oh-tani, S.; Miayura, N. J. Org. Chem. 1997, 62, 8024.
25. Zim, D.; Lando, V. R.; Dupont, J.; Monteiro, A. L. Org. Lett. 2001, 3, 3049.
26. Moreno-Manãs, M.; Pérez, M.; Pleitxats, R. J. Org. Chem. 1996, 61, 2346.
27. Miyaura, N. J. Organomet. Chem. 2002, 653, 54.