Poly(ethylene glycol) supported liquid phase synthesis of biaryls

Synlett

Volumn , Issue 3, 1998, Pages 295-297

  Blettner, Carsten G ^a,b   König, Wilfried A ^a   Stenzel, Wolfgang ^b   Schotten, Theo ^b  

^a UNIVERSITY OF HAMBURG   (Germany)

^b BEIERSDORF AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 26844485914     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1630     Document Type: Article

References (30)

1. For excellent reviews see: a) Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., 1996, 108, 2436;
2. Angew. Chem. Int. Ed. Engl., 1996, 35, 2288.
3. b) Früchtel, J. S.; Jung, G. Angew. Chem., 1996, 108, 19;
4. Angew. Chem. Int. Ed. Engl., 1996, 35, 17.
5. c) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron, 1997, 53, 5643.
6. a) Service, R. F.; Science, 1996, 272, 1266.
7. b) Zalipsky, S. Bioconjugate Chem., 1995, 6, 150.
8. th, 1974, 129.
9. a) Rajasekharan Pillai, V. N.; Mutter, M. Acc. Chem. Res., 1981, 14, 122.
10. b) Harris, J. M. In Poly(Ethylene Glycol) Chemistry Biotechnical and Biomedical Applications, Plenum Press, New York, 1992, 2.
11. 2-helix: Tadokoro, H.; Murahashi, S.; Yoshihara, T.; Tahara, S.; Murahashi, S. Macromol. Chem., 1964, 73, 109.
12. Bayer, E.; Mutter, M. Angew. Chem., 1974, 2, 101.
13. Recent PEG-supported synthesis of a) small molecules: Vandersteen, A. M.; Han, H.; Janda, K. D. Molecular Diversity, 1996, 2, 89.
14. b) oligosaccharides: Rouhi, A. M. Science, 1996, 23, 62.
15. and Douglas, S. P.; Whitfield, D. M.; Krepinsky, J. J. J. Am. Chem. Soc., 1995, 117, 2116.
16. c) oligonucleotides: Bonora, G. M. Appl. Biochem. and Biotech., 1995, 54, 3.
17. The organic synthesis on soluble polymer supports has been reviewed during the preparation of this work: Gravert, D.J.; Janda, K.D. Chem. Rev., 1997, 97, 489.
18. a) Han, H.; Wolfe, M. M.; Brenner, S.; Janda, K. D., Proc. Natl. Sci. USA, 1995, 92, 6419.
19. b) Erb, E.; Janda, K. D.; Brenner, S. Proc. Natal. Acad. Sci. USA, 1994, 91, 11422.
20. Duncia, J. V.; Carini, J. D.; Chiu, A. T.; Johnson, A. L.; Price, W. A.; Wong, P. C.; Wexler, R. R.; Timmermans, P. B. M. W. M. Medical Research Reviews, 1992, 12, 149.
21. a) Miyaura, N.; Yanagi, Y.; Suzuki, A. Synth. Commun., 1981, 11, 513.
22. b) Watanabe, T.; Miyaura, N.; Suzuki, A. Synlett, 1992, 207.
23. For reviews on the Suzuki reaction see: a) Martin, A. R.; Yang, Y. Acta Chem. Scand. 1993, 47, 221.
24. b) Suzuki, A. Pure & Appl. Chem., 1994, 66, 213.
25. c) Miyaura, N.; Suzuki, A. Chem. Rev., 1995, 95, 2457.
26. 1H-NMR. The MALDI-TOF MS technique was used to follow the conversion of the starting material quantitatively.
27. 3): 8.06 (1H, d, J = 7.6 Hz); 7.59 (1H, t, J = 7.4 Hz); 7.49 (1H, t, J = 7.5 Hz); 7.44 (1H, s); 7.30 (1H, d, J = 8.2 Hz); 7.23 (1H, d, J = 7.8 Hz); 7.19 (1H, d, 8.2 Hz); 4.24 (2H, t, J = 4.8 Hz); 3.49-3.79 (m, PEG); 3.38 (3H, s).
28. 2: C, 59.81; H, 3.59; Cl, 25.22. Found: C, 60.00; H, 3.53; Cl, 25.24.
29. Column filtration was performed on 63-200 μ silica gel in disposable columns. 5g silica gel was used for one gram PEG 4000.
30. Bayer, E., personal communication.