Polymer-Assisted Solution-Phase (PASP) Suzuki Couplings Employing an Anthracene-Tagged Palladium Catalyst

Journal of Organic Chemistry

Volumn 68, Issue 25, 2003, Pages 9678-9686

  Lan, Ping ^a   Berta, Daniela ^a   Porco Jr , John A ^b   South, Michael S ^a   Parlow, John J ^a  

^a PFIZER INC   (United States)

^b USA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; BYPRODUCTS; CARBONATES; CATALYSTS; PALLADIUM;

COUPLING REACTIONS;

ORGANIC POLYMERS;

ANTHRACENE; BASE; BORONIC ACID DERIVATIVE; CARBONIC ACID; LIGAND; MALEIMIDE; PALLADIUM; PHOSPHINE; PHOSPHINE OXIDE DERIVATIVE; POLYMER; RESIN;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOGRAPHY; DIELS ALDER REACTION; DISSOCIATION; POLYMER ASSISTED SOLUTION PHASE SUZUKI COUPLING REACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0344666674     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035129g     Document Type: Article

References (36)

1. (a) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633-9695.
2. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168.
3. (c) Stanforth, S. P. Tetrahedron 1998, 54, 263-303.
4. (d) Miraura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
5. (a) Schiedel, M.-S.; Briehn, C. A.; Bäuerle, P. J. Organomet. Chem. 2002, 653, 200-208.
6. (b) Chang, L. L.; Ashton, W. T.; Flanagan, K. L.; Strelitz, R. A.; MacCoss, M.; Greenlee, W. J.; Chang, R. S. L.; Lotti, V. J.; Faust, K. A.; Chen, T.-B.; Bunting, P.; Zingaro, G. J.; Kivlighn, S. D.; Siegl, P. K. S. J. Med. Chem. 1993, 36, 2558-2568.
7. (c) Bovy, P. R.; Collins, J. T.; Olins, G. M.; MacMahon, E. G.; Hutton, W. C. J. Med. Chem. 1991, 34, 2410-2414.
8. Moreno-Mañas, M.; Pérez, M.; Pleixats, R. J. Org. Chem. 1996, 61, 2346-2351.
9. (a) Atrash, B.; Reader, J.; Bradley, M. Tetrahedron Lett. 2003, 44, 4779-4782.
10. (b) Parrish, C. A.; Buchwald, S. L. J. Org. Chem. 2001, 66, 3820-3827.
11. (c) Fenger, I.; Drian, C. L. Tetrahedron Lett. 1998, 39, 4287-4290.
12. (d) Jang, S.-B. Tetrahedron Lett. 1997, 38, 1793-1796.
13. (a) Yamada, Y. A.; Takeda, K.; Takahashi, H.; Ikegami, S. Org. Lett. 2002, 4, 3371-3374.
14. (b) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997-3000.
15. (c) Uozumi, Y.; Danjo, H.; Hayashi, T. J. Org. Chem. 1999, 64, 3384-3388.
16. Lawson Daku, K. M.; Newton, R. F.; Pearce, S. P.; Vile, J.; Williams, J. M. J. Tetrahedron Lett. 2003, 44, 5095-5098.
17. (a) Organ, M. G.; Mayer, S. J. Comb. Chem. 2003, 5, 118-124.
18. (b) Sakurai, H.; Tsukuda, T.; Hirao, T. J. Org. Chem. 2002, 67, 2721-2722.
19. (c) LeBlond, C. R.; Andrews, A. T.; Sun, Y.; Sowa, J. R., Jr. Org. Lett. 2001, 3, 1555-1557.
20. (d) Ennis, D. S.; McManus, J.; Wood-Kaczmar, W.; Richardson, J.; Smith, G. E.; Carstairs, A. Org. Proc. Res. Dev. 1999, 3, 248-252.
21. (e) Gala, D.; Stamford, A.; Jenkins, J.; Kugelman, M. Org. Proc. Res. Dev. 1997, 1, 163-164.
22. (f) Marck, G.; Villiger, A.; Buchecker, R. Tetrahedron Lett. 1994, 35, 3277-3280.
23. Schneider, S.; Bannwarth, W. Helv. Chim. Acta 2001, 84, 735-742.
24. For review see: Bräse, S.; Kirchhoff, J. H.; Köbberling, J. Tetrahedron 2003, 59, 885-939 and references therein.
25. (a) Pourbaix, C.; Carreaux, F.; Carboni, B. Org. Lett. 2001, 3, 803-805.
26. (b) Li, W.; Burgess, K. Tetrahedron Lett. 1999, 40, 6527-6530.
27. (a) Lan, P.; Porco, J. A., Jr.; South, M. S.; Parlow, J. J. J. Comb. Chem. 2003, 5, 660-669.
28. (b) Wang, X.; Parlow, J. J.; Porco, J. A., Jr. Org. Lett. 2000, 2, 2999-3001.
29. Li, X.; Abell, C.; Ladlow, M. J. Org. Chem. 2003, 68, 4189-4194.
30. It is known that a bulky phosphine ligand such as MOP can help retard the phenyl shifting side reaction. See ref 1a.
31. Polymer-supported palladium catalyst 4 may also serve as a polystyrene-based palladium catalyst such as those cited in ref 4.
32. The polymer-supported tetraalkylammonium carbonate was purchased from Aldrich (50-90 mesh, 2.5 mmol/g-3.5 mmol N/g.)
33. Smith, G. B.; Dezeny, G. C.; Hughes, D. L.; King, A. O.; Verhoeven, T. R. J. Org. Chem. 1994, 59, 8151-8156.
34. An ICP-AES analysis for palladium was conducted on the product mixture of 14bE after sequestration with PS-maleimide 3. ICP-AES analysis showed less than 1 ppm of Pd present with an expected theoretical value without sequestration of 91000 ppm. A second analysis on the same sample prior to sequestration had an actual value of 5 430 ppm. The difference between the theoretical and actual value was due to lack of solubility of the sample. Thus, >99.98% of palladium had been removed from the product mixture.
35. (a) Gravel, M.; Thompson, K. A.; Zak, M.; Bérubé, C.; Hall, D. G. J. Org. Chem. 2002, 67, 3-15.
36. (b) Hall, D. G.; Tailor, J. i; Gravel, M. Angew. Chem., Int. Ed. 1999, 38, 3064-3067.