Iron-catalysed Reformatsky-type reactions

Synthesis

Volumn , Issue 9, 2006, Pages 1542-1548

  Durandetti, Muriel ^a,b   Périchon, Jacques ^a  

^a CNRS   (France)

^b UNIVERSITÉ DE ROUEN   (France)

Author keywords

haloester; C C coupling; Carbonyl compounds; Iron; Reformatsky reaction

Indexed keywords

ACETONITRILE; BROMINE COMPOUNDS; CARBONYLATION; CATALYSIS; DERIVATIVES; ESTERS; KETONES; MANGANESE; REACTION KINETICS;

Α-HALOESTER; C-C COUPLING; CARBONYL COMPOUNDS; REFORMATSKY REACTION;

IRON;

ACETONITRILE; ALDEHYDE DERIVATIVE; ALPHA CHLOROESTER DERIVATIVE; BETA HYDROXYESTER DERIVATIVE; BROMINE DERIVATIVE; ESTER DERIVATIVE; IRON; IRON BROMIDE; KETONE DERIVATIVE; MANGANESE; NITRILE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; REDUCTION; REFORMATSKY REACTION;

EID: 33646555801     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926432     Document Type: Article

References (34)

1. Reformatsky, S. Ber. Dtsch. Chem. Ges. 1887, 20, 1210.
2. For recent reviews on the Reformatsky reaction, see: (a) Ocampo, R.; Dolbier, W. R. Jr. Tetrahedron 2004, 60, 9325.
3. (b) Fürstner, A. Synthesis 1989, 571.
4. (c) Rathke, M. W.; Weipert, P. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Elsevier: New York, 1991, 277-299.
5. (d) Fürstner, A. In Organozinc Reagents; Knochel, P.; Jones, P., Eds.; Oxford University Press: New York, 1999, 287-305.
6. Rieke, R. D.; Uhm, S. J. Synthesis 1975, 452.
7. Santaniello, E.; Manzocchi, A. Synthesis 1977, 698.
8. Csuk, R.; Fürster, A.; Weidmann, H. J. Chem. Soc., Chem. Commun. 1986, 775.
9. (a) Han, B.; Boudjouk, P. J. Org. Chem. 1982, 47, 5030.
10. (b) Nishiyama, T.; Woodhall, J. F.; Lawson, E. N.; Kitching, W. J. Org. Chem. 1989, 54, 2184.
11. Durant, A.; Delplanche, J.; Libert, V.; Reisse, J. Eur. J. Org. Chem. 1999, 2845.
12. Kanai, K.; Wakabayashi, H.; Honda, T. Org. Lett. 2000, 2, 2549.
13. Chattopadhyay, A.; Salaskar, A. Synthesis 2000, 561.
14. Orsini, F.; Sello, G. Curr. Org. Synth. 2004, 1, 111.
15. Inab, S.-I.; Rieke, R. D. Tetrahedron Lett. 1985, 26, 155.
16. (a) Kahiga, H.; Nishimae, S.; Shinokubo, H.; Oshima, K. Tetrahedron 2001, 57, 8807.
17. (b) Cahiez, G.; Chavant, P.-Y. Tetrahedron Lett. 1989, 30, 7373.
18. Wessjohann, L.; Gabriel, T. J. Org. Chem. 1997, 62, 3772.
19. (a) Hirashita, T.; Kinoshita, K.; Yamamura, H.; Kawai, M.; Araki, S. J. Chem. Soc., Perkin Trans. 1 2000, 5, 825.
20. (b) Lee, P. H.; Bang, K.; Sung, S.; Chang, S. Synth. Commun. 2001, 31, 3781.
21. Areias, M. C. C.; Bieber, L. W.; Navarro, M.; Diniz, F. B. J. Electroanal. Chem. 2003, 558, 125.
22. (a) Rollin, Y.; Gebehenne, C.; Derien, S.; Dunach, E.; Périchon, J. J. Orgonomet. Chem. 1993, 461, 9.
23. (b) Connan, A.; Sibille, S.; Périchon, J. J. Org. Chem. 1991, 56, 2018.
24. Durandetti, M.; Nédelec, J.-Y.; Périchon, J. Org. Lett. 2001, 3, 2073.
25. Durandetti, M.; Meignein, C.; Périchon, J. Org. Lett. 2003, 5, 317.
26. Durandetti, M.; Périchon, J. Patent application FR 2004-7230, 2004.
27. (a) Fürstner, A.; Leitner, A.; Mendez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856.
28. (b) Quintin, J.; Franck, X.; Hocquemiller, R.; Figadère, B. Tetrahedron Lett. 2002, 43, 3547.
29. (c) Fakhfakh, M. A.; Franck, X.; Hocquemiller, R.; Figadère, B. J. Organomet. Chem. 2001, 624, 131.
30. (d) Bogdanovic, B.; Schwickardi, M. Angew. Chem. Int. Ed. 2000, 39, 4610.
31. Blomberg, C. The Barbier Reaction and Related One-Step Processes; Springer: Berlin, 1993.
32. (a) Durandetti, M.; Périchon, J. Synthesis 2004, 3079.
33. (b) Durandetti, M.; Nédelec, J.-Y.; Périchon, J. J. Org. Chem. 1996, 61, 1748.
34. The insertion of a low valent iron salt into an α-haloester is already reported: Buriez, O.; Durandetti, M.; Périchon, J. J. Electroanal. Chem. 2005, 578, 63.