New progress in the cobalt-catalysed synthesis of aromatic organozinc compounds by reduction of aromatic halides by zinc dust

Tetrahedron Letters

Volumn 44, Issue 34, 2003, Pages 6417-6420

  Kazmierski, Igor ^a   Gosmini, Corinne ^a   Paris, Jean Marc ^b   Périchon, Jacques ^a  

^a CNRS Université Paris Est Créteil Val de Marne   (France)

^b Rhodia Europe   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; BROMINE DERIVATIVE; COBALT; HALIDE; ORGANOMETALLIC COMPOUND; ZINC;

ARTICLE; CATALYST; CROSS REACTION; REDUCTION; SYNTHESIS;

EID: 0042698461     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01595-8     Document Type: Article

References (15)

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10. Fillon H., Gosmini C., Périchon J. J. Am Chem. Soc. 125:2003;3867-3870 Fillon, H.; Gosmini, C.; Périchon, J. Patent Application 01/08880, France, July 4, 2001.
11. This property of allylzinc species has been reported earlier. See: (a) Blaise, E. E. C. R. Acad. Sci. 1904, 138, 284-286; (b) Rollin, Y.; Derien, S.; Dunach, E.; Gebehenne, C.; Périchon, J. Tetrahedron 1993, 49, 7723-7732.
12. This property of allylzinc species has been reported earlier. See: (a) Blaise, E. E. C. R. Acad. Sci. 1904, 138, 284-286; (b) Rollin, Y.; Derien, S.; Dunach, E.; Gebehenne, C.; Périchon, J. Tetrahedron 1993, 49, 7723-7732.
13. Fillon H., Gosmini C., Nedelec J.Y., Périchon J. Tetrahedron Lett. 42:2001;3843-3846.
14. 2 (105 mg; 0.01 equiv.) are introduced in the reaction vessel, and the reaction is stirred until complete conversion of the organozinc reagent (1 h). The reaction is then quenched with 40 mL HCl 1.5 M and extracted with 3×40 mL ether. The crude product is purified by flash chromatography on silica gel, eluted with pentane/ether 97/3 to 96/4, yielding 2.20 g (70%) of 4′-methoxy-3-cyanobiphenyl (identified by GC/MS and NMR by comparison to Ref. 13).
15. GC/MS and NMR analyses were compared to those found in the following reference: Hassan J., Hathroubi C., Gozzi C., Lemaire M. Tetrahedron. 57:2001;7845-7855.