Resin-to-resin Suzuki coupling of solid supported arylboronic acids

Journal of Combinatorial Chemistry

Volumn 2, Issue 3, 2000, Pages 228-231

  Gravel, Michel ^a   Bérubé, Christian D ^a   Hall, Dennis G ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000229382     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc990082r     Document Type: Article

References (33)

1. For a recent synthetically useful example, see: Hamuro, Y.; Scialdone, M. A.; DeGrado, W. F. J. Am. Chem. Soc. 1999, 121, 1636-1644.
2. Solid-phase Suzuki reactions with one resin-bound substrate have been described. Original references: (a) Frenette, R.; Friesen, R. W. Tetrahedron Lett. 1994, 35, 9177-9180.
3. (b) Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1994, 116, 11171-11172.
4. For a selection of recent examples of solid-phase Suzuki reactions, see: (a) Huwe, C. M.; Künzer, H. Tetrahedron Lett. 1999, 40, 683-686.
5. (b) Blettner, C. G.; König, W. A.; Rühter, G.; Stenzel, W.; Schotten, T. Synlett 1999, 307-310.
6. (c) Wendeborn, S.; Berteina, S.; Brill, W. K.-D.; De Mesmaeker, A. D. Synlett 1998, 671-675.
7. (d) Chamoin, S.; Houldsworth, S.; Kruse, C. G.; Bakker, I.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4179-4182.
8. (e) Lago, M. A.; Nguyen, T. T.; Bhatnagar, P. Tetrahedron Lett 1998, 39, 3885-3888.
9. (f) Lorsbach, B. A.; Bagdanoff, J. T.; Miller, R. B.; Kurth, M. J. J. Org. Chem. 1998, 63, 2244-2250.
10. (g) Blettner, C. G.; König, W. A.; Stenzel, W.; Schotten, T. Synlett 1998, 295-297.
11. (h) Ruhland, B.; Bombrun, A.; Gallop, M. A. J. Org. Chem. 1997, 62, 7820-7826.
12. (i) Brown, S. D.; Armstrong, R. W. J. Org. Chem. 1997, 62, 7076-7077.
13. (j) Garigipati, R. S. Tetrahedron Lett. 1997, 38, 6807-6810.
14. (k) Yoo, S.-e.; Seo, J.-s.; Yi, K.-y.; Gong, Y.-d. Tetrahedron Lett. 1997, 38, 1203-1206.
15. (l) Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169-5171.
16. Hall, D. G.; Tailor, J.; Gravel, M. Angew. Chem., Int. Ed. 1999, 38, 3064-3067.
17. For recent reviews on the Suzuki and related cross-coupling reactions, see: (a) Suzuki, A.; J. Organomet. Chem. 1999, 576, 147-168.
18. (b) Suzuki, A. in Metal-catalyzed Cross-coupling reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1997; Chapter 2.
19. In comparison to more than 1500 commercially available carboxylic acids, only 75-100 different boronic acids are offered by Aldrich and Lancaster (mostly the same ones).
20. For a review, see: 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. Med. Res: Rev. 1992, 12, 149.
21. In the resin-to-resin acyl transfer system reported by DeGrado et al. (ref 1), the transfer agents employed therein were termed chaperones because they also act as solution-phase activators.
22. In all cases no boronic acid was recovered. It was therefore completely released from the resin to solution under the reaction and resin washing conditions used. Leftover DEAM-PS resin does not liberate any byproducts upon treatment with TFA.
23. For example, see: Tripathy, P. B.; Mattesen, D. S. Synthesis 1990, 200-206.
24. We suspect that transmetalation of the corresponding diethanolamine boronic esters with the PS-Ar-Pd-I intermediate is significantly slower than with the ethylene glycol esters.
25. 3N (9:1, 105 °C, 24 h) led to less than 25% leaching of the boronic acid.
26. 2O 90:5:5, 1 h) followed by characterization of the resulting boronic acid (see Supporting Information).
27. As reported in ref 3c. Our own attempt at coupling p-carboxyben-zeneboronic acid with resin 3 has also failed.
28. Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, U.K., 1995.
29. Acylation of 14 fails with aliphatic acid chlorides under these conditions.
30. In addition, solid-phase immobilization circumvents the tendency of free boronic acids to dehydrate by forming anhydrides which are difficult to characterize and weight accurately.
31. A Quest 210 instrument with solvent wash unit was employed (Argonaut Technologies). Cleavage was effected on-line, and crude products were obtained after evaporation of solvents. Yields and purity were estimated by comparison with an internal NMR standard.
32. For examples, see: (a) Chan, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933-2936.
33. (b) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798-11799.