Metal-catalyzed release of supported boronic acids for C-C bond formation

Organic Letters

Volumn 3, Issue 6, 2001, Pages 803-805

  Pourbaix, Christelle ^a,b   Carreaux, François ^a   Carboni, Bertrand ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000403742     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000338y     Document Type: Article

References (45)

1. (a) Molecular Diversity and Combinatorial Chemistry; Chaiken, I. M., Janda, K. D., Eds; American Chemical Society: Washington, DC, 1996.
2. (b) Combinatorial Chemistry; Wilson, S. R., Czarnik, A. W., Eds; Wiley-Interscience: New York, 1997.
3. (a) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385-1401.
4. (b) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
5. (c) Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288-2337.
6. (d) Obrecht, D.; Villalgordo, J. M. Solid Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compounds Libraries; Pergamon: New York, 1998.
7. (e) Guillier, F.; Orain, D.; Bradley, M. Chem. Rev. 2000, 100, 2091-2157.
8. (a) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Opin. Chem. 1999, 3, 497-555.
9. (b) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549-1581.
10. (c) Wendeborn, S.; De Mesmaeker, A.; Brill, W. K.-D.; Berteina, S. Acc. Chem. Res. 2000, 33, 215-224.
11. Original references of solid-phase Suzuki reactions: (a) Frenette, R.; Friesen, R. W. Tetrahedron Lett. 1994, 35, 9177-9180.
12. (b) Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1994, 116, 11171-11172.
13. For a selection of recent examples of solid-phase Suzuki reactions, see: (a) Huwe, C. M.; Künzer, H. Tetrahedron Lett. 1999, 40, 683-686.
14. (b) Blettner, C. G.; König, W. A.; Rhüter, G.; Stenzel, W.; Schotten, T. Synlett 1999, 307-310.
15. (c) Chamoin, S.; Houldsworth, S.; Kruse, C. G.; Iwema Baker, W.; Snieckus, V. Tetrahedon Lett. 1998, 39, 4179-4182.
16. (d) Amparo Lago, M.; Nguyen, T. T.; Bhatnagar, P. Tetrahedron Lett. 1998, 39, 3885-3888.
17. (e) Wendeborn, S.; Berteina, S.; Brill, W. K.-D., De Mesmaeker, A. Synlett 1998, 671-675.
18. (f) Lorsbach, B. A.; Bagdanoff, J. T.; Bryan Miller, R.; Kurth, M. J. J. Org. Chem. 1998, 63, 2244-2250.
19. (g) Garigipati, R. S. Tetrahedron Lett. 1997, 38, 6807-6810.
20. (h) Yoo, S.-E.; Seo, J.-S.; Yi, K.-Y.; Gong, Y.-D. Tetrahedron Lett. 1997, 38, 1203-1206.
21. (i) Brown, S. D.; Armstrong, R. W. J. Org. Chem. 1997, 62, 7076-7077.
22. (j) Ruhland, B.; Bombrun, A.; Gallop, M. A. J. Org. Chem. 1997, 62, 7820-7826.
23. (k) Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169-5171.
24. (l) Larhed, M.; Lindeberg, G.; Hallberg, A. Tetrahedron Lett. 1996, 37, 8219-8222.
25. In comparison to more than 1500 commercially available carboxylic acids, only 100-150 different boronic acids are offered by Aldrich and Lancaster.
26. Carboni, B.; Pourbaix, C.; Carreaux, F.; Deleuze, H.; Maillard, B. Tetrahedron Lett. 1999, 40, 7979-7983.
27. For other preparations of resin-bound boronic acids, see: Hall, D. G.; Taylor, J.; Gravel, M. Angew. Chem., Int. Ed. 1999, 38, 3064-3067.
28. (a) McCarthy, P. A. Med. Res. Rev. 1993, 13, 139-159.
29. (b) Pavia, M. R.; Cohen, M. P.; Dilley, G. J.; Dubuc, G. R.; Durgin, T. L.; Forman, F. W.; Hediger, M. E.; Milot, G.; Powers, T. S.; Sucholeiki, I.; Zhou, S.; Hangauer, D. G. Bioorg. Med. Chem. 1996, 4, 659-666.
30. Pourbaix, C.; Carreaux, F.; Carboni, B.; Deleuze, H. Chem. Commun. 2000, 1275-1276.
31. Li, W.; Burgess, K. Tetrahedron Lett. 1999, 40, 6527-6530.
32. Recently, a successful strategy for resin-to-resin Suzuki coupling reactions via phase transfer of solid-supported arylboronic acids was described: Gravel, M.; Bérubé, C. D.; Hall, D. G. J. Comb. Chem. 2000, 2, 228-231.
33. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
34. Yamaguchi, S.; Ohno, S.; Tamao, K. Synlett 1997, 1199-1201.
35. The yield was measured by GC versus benzophenone internal standard relative to the loading of resin 1 (1 mmol/g). The mixture was passed through silica plugs to remove excess ligand/metal before analysis.
36. (a) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 3279-3281.
37. (b) Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450-4452.
38. (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229-4231.
39. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479-8482.
40. (c) Takaya, Y.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 1998, 120, 5579-5580.
41. Batey, R. A.; Thadani, A. N.; Smil, D. V. Org. Lett. 1999, 1, 1683-1686.
42. Immobilization of aldehydes using the diol resin of Leznoff was reported. Chamoin, S.; Houldsworth, S.; Kruse, C. G.; Iwema Baker, W.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4179-4182.
43. MVK was selected because of its low boiling point.
44. For examples, see: (a) Chan, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933-2936.
45. (b) Evans, D. A.; Katz, J. L.; West, T. H. Tetrahedron Lett. 1998, 39, 2937-2940.