Aryl-aryl cross coupling on a solid support using zinc organic reagents and palladium catalysis

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5491-5494

  Marquais, Sophie ^a   Arlt, Michael ^a  

^a MERCK KGAA   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC CARBOXYLIC ACID;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030605889     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01162-8     Document Type: Article

References (12)

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3. 2. P. H. H. Hermkens, H. C. J. Ottenheijm, D. Rees, Tetrahedron 1996, 52, 4527; J. S. Früchtel, G. Jung, Angew. Chem. Int. Ed. Eng., 1996, 35, 17.
4. 3. W. W. K. R. Mederski, D. Dorsch, H.-H. Bokel, N. Beier, I. Lues, P. Schelling, J. Med. Chem. 1994, 37, 1632.
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8. 5. E. Erdik, Tetrahedron, 1992, 48, 9577; E. Negishi, T. Takahashi, A. O. King, Org. Synth. 1988, 66, 67; L. Zhu, R. M. Wehmeyer, R. D. Rieke, J. Org. Chem. 1991, 56, 1445; C. E. Tucker, T. N. Majid, P. Knochel, J. Am. Chem. Soc. 1992, 114, 3983.
9. 5. E. Erdik, Tetrahedron, 1992, 48, 9577; E. Negishi, T. Takahashi, A. O. King, Org. Synth. 1988, 66, 67; L. Zhu, R. M. Wehmeyer, R. D. Rieke, J. Org. Chem. 1991, 56, 1445; C. E. Tucker, T. N. Majid, P. Knochel, J. Am. Chem. Soc. 1992, 114, 3983.
10. 2(dppf) were added. The mixture was stirred at ambient temperature for 18h. The polymer was then filtered on a fritted reservoir and washed successively with THF/water (1/1), THF, MeOH and ether. The resin was cleaved in a mixture of THF (4 ml) and MeOH (1 ml) in the presence of 30 mg of sodium methylate at 70°C overnight. After cooling, the resin was filtered and washed with THF, THF/water and ether. The product was then extracted with ethyl acetate. Evaporation of the solvent yielded 135 mg (84%, based on 2a) of methyl 4-(3-fluorophenyl)benzoate 4e (purity > 98% by HPLC).
11. 7. W. E. Parham, L. D. Jones, J. Org. Chem. 1976, 41, 2704; W. E. Parham, L. D. Jones, J. Org. Chem. 1976, 41, 1187.
12. 7. W. E. Parham, L. D. Jones, J. Org. Chem. 1976, 41, 2704; W. E. Parham, L. D. Jones, J. Org. Chem. 1976, 41, 1187.