Poly(ethylene glycol)-supported nitroxyls: Branched catalysts for the selective oxidation of alcohols

Journal of Organic Chemistry

Volumn 69, Issue 20, 2004, Pages 6851-6859

  Ferreira, Pedro ^a   Phillips, Emyr ^b   Rippon, David ^b   Shik, Chi Tsang ^a   Hayes, Wayne ^a  

^a UNIVERSITY OF READING   (United Kingdom)

^b A H Marks and Co Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CATALYST ACTIVITY; CATALYSTS; MACROMOLECULES; OXIDATION; PRECIPITATION (CHEMICAL);

BRANCHED CATALYSTS; NITROXYL RADICALS; POLYMER-SUPPORTED CATALYSTS;

POLYETHYLENE GLYCOLS;

2,2,6,6 TETRAMETHYLPIPERIDIN 1 OXYL; ALCOHOL; ALDEHYDE; ISOPHTHALIC ACID; MACROGOL; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CROSS LINKING; MACROMOLECULE; OXIDATION; PRECIPITATION; SOLUBILITY;

EID: 4644308026     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0490494     Document Type: Article

References (35)

1. Hudlicky, M.; Oxidations in Organic Chemistry, American Chemical Society: Washington, DC, 1990.
2. de Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153.
3. Cella, J. A.; Kelley, J. A.; Kenehan, E. F. J. Org. Chem. 1975, 40, 1860.
4. Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559.
5. Semmelhack, M. F.; Schmid, C. R.; Cortés, D. A.; Chou, C. S. J. Am. Chem. Soc. 1984, 106, 3374.
6. Semmelhack, M. F.; Chou, C. S.; Cortés, D. A. J. Am. Chem. Soc. 1983, 105, 4492.
7. (a) Bolm, C.; Fey, T. Chem. Commun. 1999, 1795.
8. (b) Fey, T.; Fischer, H.; Bachmann, S.; Albert, K.; Bolm, C. J. Org. Chem. 2001, 66, 8154.
9. (a) Verhoef, M.; Peters, J.; van Bekkum, H. Stud. Surf. Sci. Catal. 1999, 125, 465.
10. (b) Brunel, D.; Fajula, F.; Nagy, J.; Deroide, B.; Verhoef, M.; Veum, L.; Peters, J.; van Bekkum, H. Appl. Catal., A 2001, 213, 73.
11. (a) Ciriminna, R.; Blum, J.; Avnir, D.; Pagliaro, M. Chem. Commun. 2000, 1441.
12. (b) Ciriminna, R.; Bolm, C.; Fey, T.; Pagliaro, M. Adv. Synth. Catal. 2002, 344, 159.
13. (a) Boyle, N. A.; Janda, K. D. Curr. Opin. Chem. Biol. 2002, 6, 339.
14. (b) Ito, Y.; Manabe, S. Chem. Eur. J. 2002, 8, 3076.
15. For a recent overview of current opinions on recoverable soluble reagents and catalysts, see: (a) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (b) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275. (c) Dickerson, T. J., Reed, N. N.; Janda, K. D. Chem. Rev. 2002, 102, 3325. (e) Bergbreiter, D. E. Chem. Rev. 2002, 102, 3345. (f) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385. (g) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667. (h) Yoshida, J.-I.; Itami, K. Chem. Rev. 2002, 102, 3693. (i) van Heerbeek, R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Chem. Rev. 2002, 102, 3717.
16. For a recent overview of current opinions on recoverable soluble reagents and catalysts, see: (a) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (b) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275. (c) Dickerson, T. J., Reed, N. N.; Janda, K. D. Chem. Rev. 2002, 102, 3325. (e) Bergbreiter, D. E. Chem. Rev. 2002, 102, 3345. (f) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385. (g) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667. (h) Yoshida, J.-I.; Itami, K. Chem. Rev. 2002, 102, 3693. (i) van Heerbeek, R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Chem. Rev. 2002, 102, 3717.
17. For a recent overview of current opinions on recoverable soluble reagents and catalysts, see: (a) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (b) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275. (c) Dickerson, T. J., Reed, N. N.; Janda, K. D. Chem. Rev. 2002, 102, 3325. (e) Bergbreiter, D. E. Chem. Rev. 2002, 102, 3345. (f) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385. (g) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667. (h) Yoshida, J.-I.; Itami, K. Chem. Rev. 2002, 102, 3693. (i) van Heerbeek, R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Chem. Rev. 2002, 102, 3717.
18. For a recent overview of current opinions on recoverable soluble reagents and catalysts, see: (a) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (b) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275. (c) Dickerson, T. J., Reed, N. N.; Janda, K. D. Chem. Rev. 2002, 102, 3325. (e) Bergbreiter, D. E. Chem. Rev. 2002, 102, 3345. (f) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385. (g) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667. (h) Yoshida, J.-I.; Itami, K. Chem. Rev. 2002, 102, 3693. (i) van Heerbeek, R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Chem. Rev. 2002, 102, 3717.
19. For a recent overview of current opinions on recoverable soluble reagents and catalysts, see: (a) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (b) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275. (c) Dickerson, T. J., Reed, N. N.; Janda, K. D. Chem. Rev. 2002, 102, 3325. (e) Bergbreiter, D. E. Chem. Rev. 2002, 102, 3345. (f) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385. (g) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667. (h) Yoshida, J.-I.; Itami, K. Chem. Rev. 2002, 102, 3693. (i) van Heerbeek, R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Chem. Rev. 2002, 102, 3717.
20. For a recent overview of current opinions on recoverable soluble reagents and catalysts, see: (a) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (b) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275. (c) Dickerson, T. J., Reed, N. N.; Janda, K. D. Chem. Rev. 2002, 102, 3325. (e) Bergbreiter, D. E. Chem. Rev. 2002, 102, 3345. (f) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385. (g) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667. (h) Yoshida, J.-I.; Itami, K. Chem. Rev. 2002, 102, 3693. (i) van Heerbeek, R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Chem. Rev. 2002, 102, 3717.
21. For a recent overview of current opinions on recoverable soluble reagents and catalysts, see: (a) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (b) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275. (c) Dickerson, T. J., Reed, N. N.; Janda, K. D. Chem. Rev. 2002, 102, 3325. (e) Bergbreiter, D. E. Chem. Rev. 2002, 102, 3345. (f) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385. (g) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667. (h) Yoshida, J.-I.; Itami, K. Chem. Rev. 2002, 102, 3693. (i) van Heerbeek, R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Chem. Rev. 2002, 102, 3717.
22. For a recent overview of current opinions on recoverable soluble reagents and catalysts, see: (a) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (b) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275. (c) Dickerson, T. J., Reed, N. N.; Janda, K. D. Chem. Rev. 2002, 102, 3325. (e) Bergbreiter, D. E. Chem. Rev. 2002, 102, 3345. (f) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385. (g) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667. (h) Yoshida, J.-I.; Itami, K. Chem. Rev. 2002, 102, 3693. (i) van Heerbeek, R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Chem. Rev. 2002, 102, 3717.
23. Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Synlett 2001, 102.
24. (a) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489.
25. (b) Bergbreiter, D. E.; Frels, J.; Heuze, K. React. Funct. Polym. 2001, 49, 249.
26. Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Chem. Commun. 2000, 271.
27. Tanyeli, G.; Gümü, A. Tetrahedron Lett. 2003, 44, 1639.
28. Pozzi, G.; Cavazzini, M.; Quici, S.; Benaglia, M.; Dell'Anna, G. Org. Lett. 2004, 6, 441.
29. Ferreira, P.; Hayes, W.; Phillips, E.; Rippon, D.; Tsang, S. C. Green Chem. 2004, 310.
30. Metz, W. A.; Reed, N. N.; Janda, K. D. J. Org. Chem. 1999, 64, 5188.
31. Lambrych, K. R.; Gitsov, I. Macromolecules 2003, 36, 1068.
32. Mazik, M.; Sicking, W. Chem. Eur. J. 2001, 7, 664.
33. Semmelhack, M. F.; Schmid, C. R.; Cortés, D. A. Tetrahedron Lett. 1986, 27, 1119.
34. Klok, H.-A.; Joliffe, K. A.; Schauer, C. L.; Prins, L. J.; Spatz, J. P. J. Am. Chem. Soc. 1999, 121, 7154.
35. Rozantsev, E. G. Free Nitroxyl Radicals; Plenum Press: New York, London, 1970.