Indium(I) bromide-mediated coupling of dibromoacetonitrile with aldehydes followed by Boord elimination of bromine and oxygen of β-bromo alkoxides for preparation of 3-organyl-2-alkenenitriles

Journal of Organometallic Chemistry

Volumn 691, Issue 11, 2006, Pages 2335-2339

  Peppe, Clovis ^a   de Azevedo Mello, Paola ^a   das Chagas, Rafael Pavão ^a  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

Author keywords

Boord elimination; Carbon carbon bond formation; Indium; Organoindium; Oxygen extrusion; Sequenced chemical reactions

Indexed keywords

ACETONITRILE; ALDEHYDES; INDIUM COMPOUNDS; OXIDES; OXYGEN;

BOORD ELIMINATION; CARBON-CARBON BOND FORMATION; ORGANOINDIUM; OXYGEN EXTRUSION; SEQUENCED CHEMICAL REACTIONS;

ORGANOMETALLICS;

EID: 33646136474     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2006.01.039     Document Type: Article

References (17)

1. Peppe C. Curr. Org. Synth. 1 (2004) 227
2. Nóbrega J.A., Gonçalves S.M.C., and Peppe C. Tetrahedron Lett. 41 (2000) 5779
3. Nóbrega J.A., Gonçalves S.M.C., and Peppe C. Tetrahedron Lett. 42 (2001) 4745
4. Peppe C., and dasChagas R.P. Synlett (2004) 1187
5. March J. Advanced Organic Chemistry. Reactions, Mechanisms and Structure. fourth ed. (1992), Wiley, New York pp. 1034-1036
6. For an earlier example of coupling between an α,α-dibroalkanenitrile and an aldehyde, followed by a Boord elimination mediated by zinc, see:. White D.R. Tetrahedron Lett. 21 (1976) 1753
7. From KOH/acetonitrile, see:. DiBiase S.A., Lipisko B.A., Haag A., Wolak R.A., and Gokel G.W. J. Org. Chem. 44 (1979) 4640
8. From MeMgCl, see:. Fleming F.F. J. Org. Chem. 67 (2002) 3668
9. Araki S., Hirashita T., Shimizu K., Ikeda T., and Butsugan Y. Tetrahedron 52 (1996) 2803
10. C. Peppe, R.P. das Chagas, Synlett (2006) in press.
11. Huang X., Xie L., and Wu H. J. Org. Chem. 53 (1988) 4862
12. Kojima S., Fukuzaki T., Yamakawa A., and Murai U. Org. Lett. 6 (2004) 3917
13. Texier-Boullet F., and Foucaud A. Synthesis (1979) 884
14. Loupy A., Sogadji K., and Seyden-Penne J. Synthesis (1977) 126
15. Robinson C.N., Horton J.L., Foshee D.O., Jones J.W., Hanissian S.H., and Slater C.D. J. Org. Chem. 51 (1986) 3535
16. Rottländer M., Boymond L., Cahiez G., and Knochel P. J. Org. Chem. 64 (1999) 1080
17. Huang Y.-Z., and Liao Y. J. Org. Chem. 56 (1991) 1381