Magnetic nanoparticles as an orthogonal support of polymer resins: Applications to solid-phase Suzuki cross-coupling reactions

Journal of Organic Chemistry

Volumn 71, Issue 2, 2006, Pages 537-542

  Zheng, Yan ^a   Stevens, Philip D ^a   Gao, Yong ^a  

^a SOUTHERN ILLINOIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CHROMATOGRAPHY; FILTRATION; MAGNETIC FIELD EFFECTS; NANOSTRUCTURED MATERIALS; PALLADIUM; POLYSTYRENES; SOLUTIONS;

ARYLBORONIC ACID; INTERPOLYMERIC CHAIN; REACTION MIXTURE; SOLID-PHASE REACTIONS;

RESINS;

BORIC ACID; BORONIC ACID DERIVATIVE; FERRIC OXIDE; HALOGENATED HYDROCARBON; NANOPARTICLE; PALLADIUM; POLYMER; POLYSTYRENE; RESIN;

ARTICLE; CATALYST; CHEMICAL REACTION KINETICS; FILTRATION; IMMOBILIZATION; MAGNETIC FIELD; MAGNETISM; ORGANIC CHEMISTRY; SOLID; SUZUKI REACTION; SYNTHESIS; TRANSMISSION ELECTRON MICROSCOPY;

BORATES; INDICATORS AND REAGENTS; KINETICS; MAGNETICS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NANOSTRUCTURES; NANOTECHNOLOGY; RESINS, SYNTHETIC;

EID: 30744455085     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051861z     Document Type: Article

References (70)

1. Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149.
2. (a) Barany, G.; Merrifield, R. B. The Peptides; Academic Press: New York, 1979.
3. (b) Meldal, M. In Methods in Enzymology: Solid-Phase Peptide Synthesis; Fields, G., Ed.; Academic Press: New York, 1997; p 83.
4. (c) Fields, G. B.; Noble, R. L. Int. J. Peptide Protein Res. 1990, 35, 161.
5. (d) Kates, S. A.; Albericio, F. Solid-Phase Synthesis. A Practical Guide: Marcel Dekker: New York, 2000.
6. (e) Zehavi, U.; Patehornik, A. J. Am. Chem. Soc. 1973, 95, 5673.
7. (f) Letsinger, R. L.; Finnan, J. L.; Heavner, G. A.; Lunsford, W. B. J. Am. Chem. Soc. 1975, 85, 3278.
8. For example: (a) Ellman, J. A. Acc. Chem. Res. 1996, 29, 132.
9. (b) Hermkens, P. H. H.; Ottenheim, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527.
10. (c) Jung, G.; Beek-Sickinger, A. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 367.
11. (d) Lam, K. S.; Salmon, S. E., Hersh, E. M.; Hruby, V. J.; Kasmierski, W. M.; Kanpp, R. J. Nature 1991, 354, 82.
12. (e) Lei, X.; Poreo, J. A., Jr. Org. Lett., 2004, 6, 795.
13. (f) Czarnik, A. W. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 12738.
14. (g) Kobayashi, S. Chem. Soc. Rev. 1999, 28, 15.
15. (h) Yamazaki, K.; Nakamura, Y.; Kondo, Y. J. Org. Chem. 2003, 68. 6011.
16. (i) Nielsen, T. E.; Le Quement, S.; Meldal, M. Org. Lett. 2005, 7, 3601.
17. (j) Bourel-Bonnet, L.; Rao, K. V.; Hamann, M. T.; Ganesan, A. J. Med. Chem. 2005, 48, 1330.
18. (k) Lo, M. M.-C.; Neumann, C. S.; Nagayama, S.; Perlstein, E. O.; Schreiber, S. L. J. Am. Chem. Soc. 2004, 126, 16077.
19. For selected reviews on solid-phase resins see: (a) Vaino, A. R.; Janda, K. D. J. Comb. Chem. 2000, 2, 579.
20. (b) Sherrington, D. C. Chem. Commun. 1998, 2275.
21. (c) Svec, F.; Fréchet, J. M. J. Science 1996, 276, 782.
22. (d) Bergbreiter, D. E. Med. Res. Rev. 1999, 19, 439.
23. For selected recent reviews on solid-phase supported catalysis see: (a) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217.
24. (b) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275.
25. (c) Dickerson, T. J.; Reed, N. N.; Janda, K. D. Chem. Rev. 2002, 102, 3325.
26. (d) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3275.
27. (e) Song, C. E.; Lee, S.-g. Chem. Rev. 2002, 102, 3495.
28. (f) Wight, A. P.; Davis, M. E. Chem. Rev. 2002, 102, 3589.
29. (g) Bräse, S.; Kirchhoff, J. H.; Köbberling, J. Tetrahedron 2003, 59, 885.
30. Numerous studies have been carried out using various techniques such as NMR, IR, fluorescence, Raman, and EPR for studying the resin structures. For some recent publications see: (a) Marchetto, R.; Cilli, E. M.; Jubilut, G. N.; Schreier, S.; Nakaie, C. R. J. Org. Chem. 2005, 70, 4561.
31. (b) Gambs, C.; Dickerson, T. J.; Mahajan, S.; Pasternack, L. B.; Janda, K. J. Org. Chem. 2003, 68, 3673.
32. (c) Warrass, R.; Wieruszeski, M.; Bouitillon, C.; Lippens, G. J. Am. Chem. Soc. 2000, 122, 1789.
33. (d) Zhao, T. J.; Beckham, H. W.; Gibson, H. W. Macromolecules 2003, 13, 4833.
34. (e) Kress, J.; Zanaletti, R.; Rose, A.; Frey, J. G.; Brockesby, W. S.; Ladlow, M.; Bradley, M. J. Comb. Chem. 2003, 5, 28.
35. (f) McAlpine, S. R.; Schreiber, S. L. Chem. Eur. J. 1999, 5, 3528.
36. Magnetic nanoparticles have been used as a novel matrix for supporting catalysts: (a) Stevens, P. D.; Fan, J.; Gardimalla, H. M. R.; Yen, M.; Gao, Y. Org. Lett. 2005, 7, 2085.
37. (b) Yoon, T.-J.; Lee, W.; Oh, Y.-S.; Lee, J.-K. New J. Chem. 2003, 27, 227.
38. For selected publications on Pd-mediated cross-coupling reactions see: (a) Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 20, 3437.
39. (b) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153.
40. (c) Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2004, 43, 1871.
41. (d) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. Engl. 1978, 17, 3387.
42. (e) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290.
43. (f) Miura, M. Angew. Chem., Int. Ed. 2004, 43, 2201.
44. (g) Lebel, H.; Janes, M. K.; Charette, A. B.; Nolan, S. P. J. Am. Chem. Soc. 2004, 126, 5046.
45. (h) Altenhoff, G.; Goddard, R.; Lehmann, C.; Glorius, F. J. Am. Chem. Soc. 2004, 126, 15196.
46. (i) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411.
47. (j) Hadei, N.; Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. Org. Lett. 2005, 7, 1991.
48. Recent examples of supported Pd catalysts for cross-coupling reactions include: (a) Byun, J.-W.; Lee, Y.-S. Tetrahedron Lett. 2004, 1837.
49. (b) Berteina, S.; Wendeborn, S.; Brill, W. K.-D.; DeMesmaeker, A. Synlett 1998, 6, 676.
50. (c) Wang, Y.; Sauer, D. R. Org. Lett. 2004, 6, 2793.
51. (d) Yamada, Y. M. A.; Takeda, K.; Takahashi, H.; Ikegami, S. Org. Lett. 2002, 4, 3371.
52. (e) Zhang, T. Y.; Allen, M. J. Tetrahedron Lett. 1999, 40, 5813.
53. (f) Yamada, Y. M. A.; Takeda, K.; Takahashi, H.; Ikegami, S. J. Org. Chem. 2003, 68, 7733.
54. Usually about 83% of Iron Oxide-Pd (based on the weights) could be separated from resins via a magnetic concentration step. However, repeated magnetic separation steps were needed to ensure complete removal of Iron Oxide-Pd out of resins. A picture of magnetic concentration using a permanent magnet is included in the Supporting Information. During magnetic separation, the mixture was then vigorously shaken followed by applying an external permanent magnet. Iron Oxide-Pd was accumulated on the sidewall of a cuvette. Excessive borate and suspended resins in solution were transferred out of the cuvette by using a pipet.
55. (a) Hyeon, T.; Lee, S. S.; Park, J.; Chung, Y.; Na, H. B. J. Am. j Chem. Soc. 2001, 123, 12798.
56. (b) Park, J.; An, K.; Hwang, Y.; Park, J.-G.; Noh, H.-J.; Kim, J.-Y.; Park, J.-H.; Hwang, N.-M.; Hyeon, T. Nat. Mater. 2004, 3, 891.
57. (a) Rajh, T.; Chen, L. X.; Lukas, K.; Liu, T.; Thurnauer, M. C.; Tiede, D. M. J. Phys. Chem. B 2002, 106, 10543.
58. (b) Kohler, N.; Fryxell G. E.; Zhang, M. J. Am. Chem. Soc. 2004, 126, 7206.
59. (c) Lu, Y.; Yin, Y.; Mayers, B. T.; Xia, Y. Nano Lett. 2002, 2, 183.
60. For example, palladium accetate was known to catalyze Suzuki cross-coupling reactions: (a) Liu, L.; Zhang, Y.; Wang, Y. J. Org. Chem. 2005, 70, 6122.
61. (b) Goodson, F. E.; Wallow, T. I.; Novak, B. M. Org. Synth. 1998, 75, 61.
62. (c) Bedford, R. B.; Blake, M. E.; Butts, C. P.; Holder, D. Chem. Commun. 2003, 466.
63. Repeated magnetic concentration and configuration steps were employed for complete removal of nanoparticle-supported Pd catalysts. TEM experiments were used to ensure complete removal of Iron Oxide-Pd from the filtrate.
64. Stevens, P. D.; Li, G.; Fan, J.; Yen, M.; Gao, Y. Chem. Commun. 2005, 4435.
65. Encapsulation of nanoparticles inside the large pores of resins has been utilized for chromatographic separation and purification of nanomaterials. For example: (a) Novak, J. P.; Nickerson, C.; Franzen, S.; Feldheim, D. L. Anal. Chem. 2001, 73, 5758.
66. (b) Jimenez, V. L.; Leopold, M. C.; Mazzitelli, C.; Jorgenson, J. W.; Murray, R. W. Anal. Chem. 2003, 75, 199.
67. (c) Krueger, K. M.; Al-Somali, A. M.; Falkner, J. C.; Colvin, V. L. Anal. Chem. 2005, 77, 3511.
68. (a) Andrews, S. P.; Stepan, A. F.; Tanaka, H.; Ley, S. V.; Smith, M. D. Adv. Synth. Catal. 2005, 347, 647.
69. (b) Davies, I. W.; Matty, L.; Hughes, D. L.; Reider, P. J. J. Am. Chem. Soc. 2001, 123, 10139.
70. Cole-Hamilton, D. J. Science 2003, 299, 1702.