Poly(ethylene glycol)-Supported TEMPO: An Efficient, Recoverable Metal-Free Catalyst for the Selective Oxidation of Alcohols

Organic Letters

Volumn 6, Issue 3, 2004, Pages 441-443

  Pozzi, Gianluca ^a   Cavazzini, Marco ^a   Quici, Silvio ^a   Benaglia, Maurizio ^b   Dell'Anna, Gianmaria ^b  

^a CNR Consiglio Nazionale delle Ricerche   (Italy)

^b UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; INORGANIC COMPOUND; MACROGOL; METAL; ORGANIC COMPOUND; OXIDIZING AGENT;

ARTICLE; CATALYSIS; CATALYST; FILTRATION; OXIDATION; STEREOCHEMISTRY; STOICHIOMETRY;

EID: 1342306648     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036398w     Document Type: Article

References (37)

1. Chiral Catalyst Immobilization and Recycling; De Vos, D. E., Vankelecom, I. F. J., Jacobs, P. A., Eds.; Wiley-VCH: Weinheim, 2000.
2. (b) An issue of Chemical Reviews has recently been devoted to recoverable catalysts and reagents: Chem. Rev. 2002, 102, 3215-3892.
3. (c) For an early review on supported catalysts, see: Manecke, G.; Storck W. Angew. Chem., Int. Ed. 1978, 17, 657.
4. For a recent review on polymer-supported organic catalysts, see: Benaglia, M.; Puglisi, A.; Cozzi, F. Chem. Rev. 2003, 103, 3401.
5. Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
6. Adam, W.; Saha-Möller, C. R.; Ganeshpure, P. A. Chem. Rev. 2001, 101, 3499.
7. For a review, see: De Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153.
8. (a) Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559.
9. (b) Anelli, P. L.; Banfi, S.; Montanari, F.; Quici, S. J. Org. Chem. 1989, 54, 2970.
10. De Mico, A.; Margarita, R.; Parlanti, L.; Vescovi, A.; Piancatelli, G. J. Org. Chem. 1997, 62, 6974.
11. (a) Jenny, C.-J.; Lohri, B.; Schlageter, M. European Patent Application EP 775,684, 1997 and U.S. Patent 5,821,374, 1998; Chem. Abstr. 1997, 127, P65794x.
12. (a) Jenny, C.-J.; Lohri, B.; Schlageter, M. European Patent Application EP 775,684, 1997 and U.S. Patent 5,821,374, 1998; Chem. Abstr. 1997, 127, P65794x.
13. (b) De Luca L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041.
14. De Luca L.; Giacomelli, G.; Masala, S.; Porcheddu, A. J. Org. Chem. 2003, 68, 4999.
15. Bolm, C.; Magnus, A. S.; Hildebrand, J. P. Org. Lett. 2000, 2, 1173.
16. Miller, R. A.; Hoerrner, R. S. Org. Lett. 2003, 5, 285.
17. Anelli, P. L.; Montanari, F.; Quici, S. Org. Synth. 1990, 69, 212.
18. (a) Heeres, A.; van Doren, H. A.; Gotlieb, K. F.; Bleeker, I. P. Carbohydr. Res. 1997, 299, 221.
19. (b) Bolm, C.; Fey, T. Chem. Commun. 1999, 1795.
20. (c) Brunel, D.; Lentz, P.; Sutra, P.; Fajula, F.; Nagy, J. B. Stud. Surf. Sci. Catal. 1999, 125, 237.
21. (d) Verhoef, M. J.; Peters, J. A.; van Bekkum, H. Stud. Surf. Sci. Catal. 1999, 125, 465.
22. (e) Ciriminna, R.; Blum, J.; Avnir, D.; Pagliaro, M. Chem. Commun. 2000, 1441.
23. (f) Fey, T.; Fischer, H.; Bachmann, S.; Albert, K.; Bolm, C. J. Org. Chem. 2001, 66, 8154.
24. Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Chem. Commun. 2000, 271.
25. For a discussion of this issue and the development of an efficient heterogeneous TEMPO catalyst, see: Ciriminna, R.; Bolm, C.; Fey, T.; Pagliaro, M. Adv. Synth. Catal. 2002, 344, 271.
26. Benaglia, M.; Danelli, T.; Fabris, P.; Sperandio, D.; Pozzi G. Org. Lett. 2002, 4, 4229 and references therein.
27. Danelli, T.; Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Tocco, G. Tetrahedron: Asymmetry 2003, 14, 461 and references therein.
28. Review: (a) Gravert, D. J.; Janda K. D. Chem. Rev. 1997, 97, 489. (b) Wentworth, P.; Janda K. D. Chem. Commun. 1999, 1917.
29. Review: (a) Gravert, D. J.; Janda K. D. Chem. Rev. 1997, 97, 489. (b) Wentworth, P.; Janda K. D. Chem. Commun. 1999, 1917.
30. For a review on PEG-supported catalysts, see: Dickerson, T. J.; Reed N. N.; Janda K. D. Chem. Rev. 2002, 102, 3325. For the use of other soluble polymer-supported catalysts, see: Bergbreiter, D. E. Chem. Rev. 2002, 102, 3345.
31. For a review on PEG-supported catalysts, see: Dickerson, T. J.; Reed N. N.; Janda K. D. Chem. Rev. 2002, 102, 3325. For the use of other soluble polymer-supported catalysts, see: Bergbreiter, D. E. Chem. Rev. 2002, 102, 3345.
32. (a) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Pitillo, M. J. Org. Chem. 2001, 66, 3160.
33. (b) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Pozzi G. Eur. J. Org. Chem., 2002, 1191.
34. (c) Benaglia, M.; Danelli, T.; Pozzi, G. Org. Biomol. Chem. 2003, 1, 454.
35. For a detailed description of the isolation, purification, and yield determination of PEG-supported compounds, see: Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F. Chem. Eur. J. 2000, 6, 133.
36. It should be noted that the oxidation of aldehydes to carboxylic acids is remarkably slow when TEMPO is used as the catalyst under the same conditions (ref 5a). However, the addition of a phase-transfer catalyst leads to reaction completion in a few minutes; the PEG portion of 7 could play a similar role. We are currently investigating this particular behavior of the PEG-immobilized catalyst.
37. Polymer-supported TEMPO catalysts soluble in organic solvents have been recently prepared by ROMP of norbornene derivatives and tested in the oxidation of alcohols with bleach in the presence of KBr. The activity of these catalysts is consistently lower than that of TEMPO. Tanyeli, C.; Gümü, A. Tetrahedron Lett. 2003, 44, 1639.