Palladium-catalyzed coupling of functionalized bromoarenes to a polystyrene-bound aryl tributylstannane

Tetrahedron Letters

Volumn 40, Issue 3, 1999, Pages 415-418

  Brody, Marcus S ^a   Finn, M G ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; FUNCTIONAL GROUP; PALLADIUM; PALLADIUM COMPLEX; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POLYSTYRENE; TIN DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHROMATOGRAPHY; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 0033555799     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02384-3     Document Type: Article

References (43)

1. (a) G. Liu, J. A. Ellman, J. Org. Chem. 1995, 60, 7712-7713.
2. (b) B. M. Cole, K. D. Shimizu, C. A. Krueger, J. P. A. Harrity, M. L. Snapper, A. H. Hoveyda, Angew. Chem. Int. Ed. Engl. 1996, 35, 1668-1671.
3. (c) K. D. Shimizu, B. M. Cole, C. A. Krueger, K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, Angew. Chem. Int. Ed. Engl. 1997, 36, 1704-1707.
4. (d) M. S. Sigman, E. N Jacobsen, J. Am. Chem. Soc. 1998, 120, 4901-4902.
5. (a) Stille, J. K. Angew. Chem. Int. Ed. Engl. 1986, 25, 508-524.
6. (b) Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551-564.
7. (c) Mitchell, T.N. Synthesis 1992, 803-815.
8. (d) Farina, V.; Roth, G.P. In Advances in Metal-Organic Chemistry; Liebeskind, L.S., Ed.; JAI: Greenwich, 1995; Vol. 5.
9. (a) Stille, J. K.; Su, H.; Hill, D. H.; Schnieder, P.; Tanaka, M.; Morrison, D. L.; Hegedus, L. S. Organometallics 1991, 10, 1993-2000.
10. (b) Yu, K.-L.; Deshpande, M. S.; Vyas, D. M. Tetrahedron Lett. 1994, 35, 8919-8922.
11. (c) Forman, F. W.; Sucholeiki, I. J. Org. Chem. 1995, 60, 523-528.
12. (d) Frenette, R.; Friesen, R. W. Tetrahedron Lett. 1994, 35, 9177-9180.
13. (e) Deshpande, M. S. Tetrahedron Lett. 1994, 35, 5613-5614.
14. (f) Hiroshige, M.; Hauske, J. R.; Zhou, P. J. Am. Chem. Soc. 1995, 117, 11590-11591.
15. (g) Hiroshige, M.; Hauske, J. R.; Zhou, P. Tetrahedron Lett. 1995, 36, 4567-4570.
16. (h) Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1994, 116, 11171-11172.
17. (i) Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306-3307.
18. (j) Han, Y.; Walker, S. D.; Young, R. N. Tetrahedron Lett. 1996, 37, 2703-2706.
19. (k) Brown, S.D.; Armstrong, R.W. J. Am. Chem. Soc. 1996, 118, 6331-2.
20. (l) Guiles, J.W.; Johnson, S.G.; Murray, M.V. J. Org. Chem. 1996, 61, 5169-71.
21. (m) Garigipati, R.S.; Adams, B.; Adams, J.L.; Sarkar, S.K. J. Org. Chem. 1996, 61, 2911-14.
22. (n) Marquais, S.; Artl, M. Tetrahedron Lett. 1996, 37, 5491-94.
23. (o) Beaver, K.A.; Siegmund, A.C.; Spear, K.L. Tetrahedron Lett. 1996, 37, 1145-48.
24. (p) Ward, Y.D.; Farina, V. Tetrahedron Lett. 1996, 37, 6993-96.
25. (q) Willoughby, C.A.; Chapman, K.T. Tetrahedron Lett. 1996, 37, 7181-84.
26. (r) Yun, W.; Mohan, R. Tetrahedron Lett. 1996, 37, 7189-92.
27. (s) Larhed, M.; Lindeberg, G.; Hallberg, A. Tetrahedron Lett. 1996, 37, 8219-222.
28. (t) Chenera, B.; Finkelstein, J.A.; Veber, D.F. J. Am. Chem. Soc. 1995, 117, 11999-12000.
29. (u) Pop, I.E.; Dhalluin, C.F.; Deprez, B.P.; Melnyk, P.C.; Lippens, G.M.; Tartar, A.L. Tetrahedron 1996, 52, 12209-222.
30. (v) For Stille coupling using fluorinated compounds in liquid-phase combinatorial synthesis, see: Curran, D.P.; Hoshino, M. J. Org. Chem. 1996, 61, 6480-6481.
31. 4, refluxing toluene]. followed by saponification (KOH, aq. EtOH).
32. This represents a substitution yield of 67%, accounting for the change in mass of the polymer substituents. No effort was made to force the substitution reactions to completion, although we have done so for alkoxide nucleophiles.
33. Beller, M.; Fischer, H.; Herrmann, W.A.; Olefe, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848-1849. See also: Piettre, S.R.; Baltzer, S. Tetrahedron Lett. 1997, 38, 1197-1200.
34. Beller, M.; Fischer, H.; Herrmann, W.A.; Olefe, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848-1849. See also: Piettre, S.R.; Baltzer, S. Tetrahedron Lett. 1997, 38, 1197-1200.
35. Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434-5444.
36. (a) Herrmann, W. A.; Brossmer, C.; Ölefe, K.; Reisinger, C.-P.; Priermeiser, T.; Beller, M.; Fischer, H. Angew. Chem. Int. Ed. Engl. 1995, 34, 1844-1848.
37. (b) Beller, M.; Fischer, H.; Herrmann, W. A.; Ölefe, K.; Brossmer, C. Angew. Chem. Int. Ed. Engl. 1995, 34, 1848-1849.
38. (c) Herrmann, W. A.; Brossmer, C.; Reisinger, C.-P.; Riermeier, T. H.; Olefe, K.; Beller, M. Chem. Eur. J. 1997, 3, 1357-1364.
39. Temperatures in excess of 80°C are needed to activate the catalyst; see Louie, J.; Hartwig, J.F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2359-2361.
40. 4), filtered, and evaporated. Purification of the residue by column chromatography (silica gel, petroleum ether/EtOAc) afforded the biphenyl products.
41. 3 residue, either on the phenol or carboxylic acid group. This was easily removed prior to final purification by treatment with aqueous acid.
42. 2 (2x).
43. Cleavage of coupling products from the support was typically performed on 100 mg resin samples by treatment of a 4:1 THF:MeOH (10 mL) suspension with 3 drops of 0.5 M methanolic NaOMe, followed by heating to reflux for 12 hours. The resin was filtered and washed with THF (5 mL), MeOH (5 mL), and 1:1 THF: MeOH (5 mL). The collected solution was evaporated and the residue dissolved in 5 mL EtOAc and filtered through a fiberglass filter plug. The solvent was removed and the residue purified if necessary by passage through a plug of silica gel, eluting with a petroleum ether-EtOAc mixture.