Manganese-catalyzed substitution of activated aryl halides (X = Cl, Br and F) and aryl ethers by organomagnesium reagents

Synthesis

Volumn , Issue 12, 1999, Pages 2138-2144

  Cahiez, Gérard ^a   Lepifre, Franck ^a   Ramiandrasoa, Parfait ^a  

^a Ecl Superieure Chim Organique M   (France)

Author keywords

Aryl ethers; Aryl halides; Arylation; Cross coupling reaction; Manganese; Organomagnesium compounds

Indexed keywords

ETHER DERIVATIVE; MAGNESIUM DERIVATIVE; MANGANESE; ORGANOHALOGEN DERIVATIVE;

ARTICLE; CATALYSIS; COMPLEX FORMATION; MOLECULAR INTERACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 0032713576     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3644     Document Type: Article

References (28)

1. a) Kharasch M. S.; Fields E. K. J. Am. Chem. Soc. 1941, 63, 2316.
2. b) Kharasch M. S.; Fushs C. F. J. Am. Chem. Soc. 1943, 65, 504.
3. c) Kharasch M. S.; Urry W. H. J. Org.Chem. 1948, 13, 101.
4. d) Kharash M. S.; Fushs C. F. J. Org.Chem. 1945, 10, 292.
5. a) Kochi, J. K. Organometallic Mechanisms and Catalysis; Academic: London, 1978; p 374.
6. b) Kochi, J. K. Acc. Chem. Res. 1974, 7, 351.
7. c) Kumada, M. Pure Appl. Chem. 1980, 52, 669.
8. d) Tamao, K.; Kumada, M. In The Chemistry of the Metal-Carbon Bond; Hartley F.R., Ed.; Wiley: New York, 1987; p.819.
9. e) Negishi, E. Acc. Chem. Res. 1982, 15, 340.
10. f) Erdik, E. Tetrahedron 1992, 48, 9577.
11. g) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117.
12. h) Stille, J. K. Angew. Chem. 1986, 98, 504; Angew. Chem. Int. Ed. Engl. 1986, 25, 508.
13. h) Stille, J. K. Angew. Chem. 1986, 98, 504; Angew. Chem. Int. Ed. Engl. 1986, 25, 508.
14. i) Kalini, V. N. Synthesis 1992, 413.
15. j) Suzuki, A. Pure Appl. Chem. 1985, 57, 1749.
16. k) Posner, G. H. Organic Reactions, Vol. 22; Dauben W. G., Ed.; Wiley: New York, 1975; p 253.
17. l) Normant, J. F., J Organomet. Chem. Library 1976, 1, 219.
18. Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: New York, 1998
19. Cahiez, G.; Avedissian, H. Synthesis 1998, 1199.
20. Stanforth, S. P. Tetrahedron 1998, 54, 263.
21. a) Reuman, M.; Meyers, A. I. Tetrahedron 1985, 41, 837.
22. b) Reuman, M.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
23. Bunnett, J. F.; Garbisch Jr., E. W.; Pruitt, K. M. J. Am. Chem. Soc. 1957, 79, 385.
24. Meyers, A. I.; Gabel, R.; Mihelich, E. D. J. Org. Chem. 1978, 43, 1372.
25. Wenkert, E.; Michelotti, E. L.; Swindell, C. S.; Tingoli, M. J. Org. Chem. 1984, 49, 4894.
26. Kim, K. S.; Qian, L.; Bird, J.E.; Dickinson, K. E. J.; Moreland, S.; Schaeffer, T. R.; Waldron, T. L.; Delaney, C. L.; Weller, H. N.; Miller, A. V. J. Med. Chem. 1993, 36, 2335.
27. Cullen, K. E.; Sharp, J. T. J. Chem. Soc., PerkinTrans. 1 1993, 2961.
28. Tinnemans, A. H. A.; Laarhoven, W. H. J. Am. Chem. Soc. 1974, 96, 4611.