Cobalt-catalyzed alkenylation of organomagnesium reagents

Tetrahedron Letters

Volumn 39, Issue 34, 1998, Pages 6159-6162

  Cahiez, Gérard ^a   Avedissian, Hovsep ^a  

^a Ecole Superieure de Chimie Organique et Minerale   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; BROMIDE; COBALT; IODIDE; MAGNESIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; FRANCE; STEREOCHEMISTRY;

EID: 0032552149     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01266-0     Document Type: Article

References (22)

1. 1 Cahiez, G.; Marquais, S. Synlett 1993, 45-47.
2. 2. Cahiez, G.; Marquais, S. Pure & Appl. Chem. 1996, 68, 53-60.
3. 3. Cahiez, G.; Marquais, S. Tetrahedron Lett. 1996, 37, 1773-1776.
4. 4. Cahiez, G.; Avedissian, H. Synthesis 1998, in press.
5. 5. a/ Kharasch M. S.; Fields E. K. J. Am. Chem. Soc. 1941, 63, 2316-2320.
6. b/ Kharasch M. S.; Fushs C. F. J. Am. Chem. Soc. 1943, 65, 504-507.
7. c/ Kharasch M. S.; Urry W. H. J. Org.Chem. 1948, 13, 101-109.
8. d/ Kharash M. S.; Fushs C. F. J. Org.Chem. 1945, 10, 292-297.
9. e/ Smith W. B. J.Org.Chem. 1959, 24, 703-704.
10. f/ Elsom L. F.; Hunt J. D.; Mckillop A. Organomet. Chem. Rev. A 1972, 8, 135-152.
11. The cross-coupling reaction between lithium organocobaltates and alkenyl halides has also been studied, see: a/ Corey E. J.; Posner G. H. Tetrahedron Lett. 1970, 315-318.
12. b/ Kauffmann T.; Stach D. Angew. Chem. Int. Ed. Engl. 1991, 30, 1684-1685.
13. c/ Kauffman T.; Nienaber H.; Stach D. Inorg. Chim. Acta. 1994, 220, 85-92.
14. d/ Kauffmann T. Synthesis 1995, 745-755.
15. e/ Kauffmann T.; Nienaber H Synthesis 1995, 207-211.
16. f/ Kauffmann T.; Laarmann B.; Menges D.; Voβ K.-U.; Wingbermühle D. Tetrahedron Lett.; 1990, 31, 507-510.
17. g/ Kauffmann T.; Hopp G.; Laarmann B.; Stegemann D.; Wingbermühle D. Tetrahedron Lett. 1990, 31, 511-514.
18. 3, TMS, δ in ppm): 13.53, 20.39, 21.83, 25.44, 28.26, 28.39, 29.13, 31.46, 31.93, 32.13, 64.06, 129.65, 130.08, 170.38
19. 2(dppf). For instance, see: a/Tamio H.; Konishi M.; Kumada M. Tetrahedron Lett.. 1979, 20, 1871-1874.
20. b/ Tamao H.; Konishi M.; Kobori Y.; Kumada M.; Higuchi T.; Hirotsu K. J. Am. Chem. Soc. 1984, 106, 158-163.
21. c/ Tamio H.; Konishi M.; Yokata K. I.; Kumada M. Chem. Lett, 1980, 767-768.
22. 9. The synthesis of 1-chloro-1-alkenes from (E) 1,2-dichloroethylene can also be performed with a nickel catalysis. The yields are similar to those described in this letter, however, contrary to the cobalt-catalyzed procedure, the formation of the product resulting from the substitution of the two chlorine atoms is observed as side reaction and it is necessary to use an excess of 1,2 dichloroethylene (5 equiv.). Ratovelomanana V.; Linstrumelle G. Tetrahedron Lett. 1981, 22, 315-318.