New chemical cross-coupling between aryl halides and allylic acetates using a cobalt catalyst

Organic Letters

Volumn 5, Issue 7, 2003, Pages 1043-1045

  Gomes, Paulo ^a   Gosmini, Corinne ^a   Périchon, Jacques ^a  

^a CNRS Université Paris 12 Val de Marne   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ACETONITRILE DERIVATIVE; AROMATIC COMPOUND; COBALT; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRIDINE DERIVATIVE; REDUCING AGENT;

ALLYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CROSS COUPLING REACTION; GAS CHROMATOGRAPHY; REDUCTION;

EID: 0141853795     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0340641     Document Type: Article

References (19)

1. Wenkert, E.; Fernandes, J. B.; Michelotti, E. L.; Swindell, C. S. Synthesis 1983, 701.
2. (a) Kharasch, M. S.; Reinmuth, O. In Grignard Reactions of Nonmetallic Substances; Coustable: London, 1954.
3. (b) Hayashi, T.; Konishi, M.; Yokota, K.-i.; Kumada, M. J. Chem. Soc., Chem. Commun. 1981, 313.
4. (c) Hayashi, T.; Konishi, M.; Yokota, K.-i.; Kumada, M. J. Organomet. Chem. 1985, 285, 359.
5. Rottländer, M.; Boymond, L.; Bérillon, L.; Leprêtre, A.; Varchi, G.; Avolio, S.; Laaziri, H.; Quéguiner, G.; Ricci, A.; Cahiez, G.; Knochel, P. Chem. Eur. J. 2000, 6, 767.
6. (a) Majid, T. N.; Knochel, P. Tetrahedron Lett. 1990, 31, 4413.
7. (b) Zhu, L.; Wehmeyer, R. M.; Rieke, R. D. J. Org. Chem. 1991, 56, 1445.
8. Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5531.
9. Yokoyama, Y.; Ito, S.; Takahashi, Y.; Murakami, Y. Tetrahedron Lett. 1985, 26, 6457.
10. Kosugi, M.; Sasazawa, K.; Shimizu, Y.; Migita, T. Chem. Lett. 1977, 301.
11. Bouyssi, D.; Gerusz, V.; Balme, G. Eur. J. Org. Chem. 2002, 2445.
12. Durandetti, M.; Nédélec, J.-Y.; Périchon, J. J. Org. Chem. 1996, 61, 1748.
13. Gomes, P.; Gosmini, C.; Périchon, J. J. Org. Chem. 2003, 68, 1142.
14. (b) Gomes, P.; Gosmini, C.; Périchon, J. Fr. Pat. Appl. 01/08808, July 3, 2001.
15. (a) Fillon, H.; Gosmini, C.; Périchon, J. Fr. Pat. Appl. 01/08880, July 4, 2001.
16. (b) Fillon, H.; Gosmini, C.; Périchon, J. J. Am. Chem. Soc. 2003, in press.
17. General Procedure for Aryl Chlorides. Allyl acetate (10 mmol) and aryl chloride (5 mmol) were introduced into a solution of acetonitrile and pyridine (20 mL/2 mL) containing manganese dust (50 mmol), cobalt bromide (2 mmol), and iron bromide (5 mmol). The solution was heated at 50°C, and the reaction mixture was stirred until the total consumption of the aryl chloride. Allylbenzenes were purified as described above.
18. Buriez, O.; Labbé, E.; Périchon, J. J. Electroanal. Chem, in press.
19. Buriez, O.; Cannes, C.; Nédélec, J.-Y.; Périchon, J. J. Electroanal. Chem. 2000, 495, 57.