Polymer-supported nitroxyl radical catalyst for selective aerobic oxidation of primary alcohols to aldehydes

Chemical Communications

Volumn , Issue 8, 2005, Pages 1085-1086

  Gilhespy, Michelle ^a   Lok, Martin ^a   Baucherel, Xavier ^a  

^a JOHNSON MATTHEY CATALYSTS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALDEHYDE; ALKANOL; BENZYL ALCOHOL; COBALT COMPLEX; MANGANESE DERIVATIVE; OXYGEN; POLYMER; RADICAL; TEMPOL;

ALCOHOL OXIDATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; FILTRATION; POLYMERIZATION; RECYCLING;

EID: 14944364228     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b415902k     Document Type: Article

References (23)

1. M. Hudlicky, Oxidations in Organic Chemistry; American Chemical Society: Washington, DC, 1990.
2. R. A. Sheldon, I. W. C. E. Arends and A. Dijksman, Catal. Today, 2000, 57, 157-166; T. Mallat and A. Baiker, Catal. Today, 1994, 19, 247-283.
3. R. A. Sheldon, I. W. C. E. Arends and A. Dijksman, Catal. Today, 2000, 57, 157-166; T. Mallat and A. Baiker, Catal. Today, 1994, 19, 247-283.
4. A. E. J. de Nooy, A. C. Besemer and H. van Bekkum, Synthesis, 1996, 1153-1174; P. L. Anelli, C. Biffi, F. Montanari and S. Quici, J. Org. Chem., 1987, 52, 2559-2562.
5. A. E. J. de Nooy, A. C. Besemer and H. van Bekkum, Synthesis, 1996, 1153-1174; P. L. Anelli, C. Biffi, F. Montanari and S. Quici, J. Org. Chem., 1987, 52, 2559-2562.
6. R. Liu, X. Liang, C. Dong and S. Hu, J. Am. Chem. Soc., 2004, 126, 4112-4113; P. Gamez, I. W. C. E. Arends, J. Reedijk and R. A. Sheldon, Chem. Commun., 2003, 2414-2415; R. Ben-Daniel, P. Alsters and R. Neumann, J. Org. Chem., 2001, 66, 8650-8653; A. Dijksman, A. Marino-Gonzalez, A. Mairata i Payeras, I. W. C. E. Arends and R. A. Sheldon, J. Am. Chem. Soc., 2001, 123, 6826-6833; A. Cecchetto, F. Fontana, F. Minisci and F. Recupero, Tetrahedron Lett., 2001, 42, 6651-6653; M. F. Semmelhack, C. R. Schmid, D. A. Cortés and C. S. Chou, J. Am. Chem. Soc., 1984, 106, 3374-3376.
7. R. Liu, X. Liang, C. Dong and S. Hu, J. Am. Chem. Soc., 2004, 126, 4112-4113; P. Gamez, I. W. C. E. Arends, J. Reedijk and R. A. Sheldon, Chem. Commun., 2003, 2414-2415; R. Ben-Daniel, P. Alsters and R. Neumann, J. Org. Chem., 2001, 66, 8650-8653; A. Dijksman, A. Marino-Gonzalez, A. Mairata i Payeras, I. W. C. E. Arends and R. A. Sheldon, J. Am. Chem. Soc., 2001, 123, 6826-6833; A. Cecchetto, F. Fontana, F. Minisci and F. Recupero, Tetrahedron Lett., 2001, 42, 6651-6653; M. F. Semmelhack, C. R. Schmid, D. A. Cortés and C. S. Chou, J. Am. Chem. Soc., 1984, 106, 3374-3376.
8. R. Liu, X. Liang, C. Dong and S. Hu, J. Am. Chem. Soc., 2004, 126, 4112-4113; P. Gamez, I. W. C. E. Arends, J. Reedijk and R. A. Sheldon, Chem. Commun., 2003, 2414-2415; R. Ben-Daniel, P. Alsters and R. Neumann, J. Org. Chem., 2001, 66, 8650-8653; A. Dijksman, A. Marino-Gonzalez, A. Mairata i Payeras, I. W. C. E. Arends and R. A. Sheldon, J. Am. Chem. Soc., 2001, 123, 6826-6833; A. Cecchetto, F. Fontana, F. Minisci and F. Recupero, Tetrahedron Lett., 2001, 42, 6651-6653; M. F. Semmelhack, C. R. Schmid, D. A. Cortés and C. S. Chou, J. Am. Chem. Soc., 1984, 106, 3374-3376.
9. R. Liu, X. Liang, C. Dong and S. Hu, J. Am. Chem. Soc., 2004, 126, 4112-4113; P. Gamez, I. W. C. E. Arends, J. Reedijk and R. A. Sheldon, Chem. Commun., 2003, 2414-2415; R. Ben-Daniel, P. Alsters and R. Neumann, J. Org. Chem., 2001, 66, 8650-8653; A. Dijksman, A. Marino-Gonzalez, A. Mairata i Payeras, I. W. C. E. Arends and R. A. Sheldon, J. Am. Chem. Soc., 2001, 123, 6826-6833; A. Cecchetto, F. Fontana, F. Minisci and F. Recupero, Tetrahedron Lett., 2001, 42, 6651-6653; M. F. Semmelhack, C. R. Schmid, D. A. Cortés and C. S. Chou, J. Am. Chem. Soc., 1984, 106, 3374-3376.
10. R. Liu, X. Liang, C. Dong and S. Hu, J. Am. Chem. Soc., 2004, 126, 4112-4113; P. Gamez, I. W. C. E. Arends, J. Reedijk and R. A. Sheldon, Chem. Commun., 2003, 2414-2415; R. Ben-Daniel, P. Alsters and R. Neumann, J. Org. Chem., 2001, 66, 8650-8653; A. Dijksman, A. Marino-Gonzalez, A. Mairata i Payeras, I. W. C. E. Arends and R. A. Sheldon, J. Am. Chem. Soc., 2001, 123, 6826-6833; A. Cecchetto, F. Fontana, F. Minisci and F. Recupero, Tetrahedron Lett., 2001, 42, 6651-6653; M. F. Semmelhack, C. R. Schmid, D. A. Cortés and C. S. Chou, J. Am. Chem. Soc., 1984, 106, 3374-3376.
11. R. Liu, X. Liang, C. Dong and S. Hu, J. Am. Chem. Soc., 2004, 126, 4112-4113; P. Gamez, I. W. C. E. Arends, J. Reedijk and R. A. Sheldon, Chem. Commun., 2003, 2414-2415; R. Ben-Daniel, P. Alsters and R. Neumann, J. Org. Chem., 2001, 66, 8650-8653; A. Dijksman, A. Marino-Gonzalez, A. Mairata i Payeras, I. W. C. E. Arends and R. A. Sheldon, J. Am. Chem. Soc., 2001, 123, 6826-6833; A. Cecchetto, F. Fontana, F. Minisci and F. Recupero, Tetrahedron Lett., 2001, 42, 6651-6653; M. F. Semmelhack, C. R. Schmid, D. A. Cortés and C. S. Chou, J. Am. Chem. Soc., 1984, 106, 3374-3376.
12. G. Pozzi, M. Cavazzini, S. Quid, M. Benaglia and G. Dell'Anna, Org. Lett., 2004, 6, 441-443; P. Ferreira, W. Hayes, E. Phillips, D. Rippon and S. Chi Tsang, Green Chem., 2004, 6, 310-312; C. Tanyeli and A. Gümüs, Tetrahedron Lett., 2003, 44, 1639-1642; R. Ciriminna, C. Bolm, T. Fey and M. Pagliaro, Adv. Synth. Catal., 2002, 344, 159-163; T. Fey, H. Fischer, S. Bachmann, K. Albert and C. Bolm, J. Org. Chem., 2001, 66, 8154-8159; A. Dijksman, I. W. C. E. Arends and R. A. Sheldon, Chem. Commun., 2000, 271-272; C. Bolm and T. Fey, Chem. Commun., 1999, 1795-1796.
13. G. Pozzi, M. Cavazzini, S. Quid, M. Benaglia and G. Dell'Anna, Org. Lett., 2004, 6, 441-443; P. Ferreira, W. Hayes, E. Phillips, D. Rippon and S. Chi Tsang, Green Chem., 2004, 6, 310-312; C. Tanyeli and A. Gümüs, Tetrahedron Lett., 2003, 44, 1639-1642; R. Ciriminna, C. Bolm, T. Fey and M. Pagliaro, Adv. Synth. Catal., 2002, 344, 159-163; T. Fey, H. Fischer, S. Bachmann, K. Albert and C. Bolm, J. Org. Chem., 2001, 66, 8154-8159; A. Dijksman, I. W. C. E. Arends and R. A. Sheldon, Chem. Commun., 2000, 271-272; C. Bolm and T. Fey, Chem. Commun., 1999, 1795-1796.
14. G. Pozzi, M. Cavazzini, S. Quid, M. Benaglia and G. Dell'Anna, Org. Lett., 2004, 6, 441-443; P. Ferreira, W. Hayes, E. Phillips, D. Rippon and S. Chi Tsang, Green Chem., 2004, 6, 310-312; C. Tanyeli and A. Gümüs, Tetrahedron Lett., 2003, 44, 1639-1642; R. Ciriminna, C. Bolm, T. Fey and M. Pagliaro, Adv. Synth. Catal., 2002, 344, 159-163; T. Fey, H. Fischer, S. Bachmann, K. Albert and C. Bolm, J. Org. Chem., 2001, 66, 8154-8159; A. Dijksman, I. W. C. E. Arends and R. A. Sheldon, Chem. Commun., 2000, 271-272; C. Bolm and T. Fey, Chem. Commun., 1999, 1795-1796.
15. G. Pozzi, M. Cavazzini, S. Quid, M. Benaglia and G. Dell'Anna, Org. Lett., 2004, 6, 441-443; P. Ferreira, W. Hayes, E. Phillips, D. Rippon and S. Chi Tsang, Green Chem., 2004, 6, 310-312; C. Tanyeli and A. Gümüs, Tetrahedron Lett., 2003, 44, 1639-1642; R. Ciriminna, C. Bolm, T. Fey and M. Pagliaro, Adv. Synth. Catal., 2002, 344, 159-163; T. Fey, H. Fischer, S. Bachmann, K. Albert and C. Bolm, J. Org. Chem., 2001, 66, 8154-8159; A. Dijksman, I. W. C. E. Arends and R. A. Sheldon, Chem. Commun., 2000, 271-272; C. Bolm and T. Fey, Chem. Commun., 1999, 1795-1796.
16. G. Pozzi, M. Cavazzini, S. Quid, M. Benaglia and G. Dell'Anna, Org. Lett., 2004, 6, 441-443; P. Ferreira, W. Hayes, E. Phillips, D. Rippon and S. Chi Tsang, Green Chem., 2004, 6, 310-312; C. Tanyeli and A. Gümüs, Tetrahedron Lett., 2003, 44, 1639-1642; R. Ciriminna, C. Bolm, T. Fey and M. Pagliaro, Adv. Synth. Catal., 2002, 344, 159-163; T. Fey, H. Fischer, S. Bachmann, K. Albert and C. Bolm, J. Org. Chem., 2001, 66, 8154-8159; A. Dijksman, I. W. C. E. Arends and R. A. Sheldon, Chem. Commun., 2000, 271-272; C. Bolm and T. Fey, Chem. Commun., 1999, 1795-1796.
17. G. Pozzi, M. Cavazzini, S. Quid, M. Benaglia and G. Dell'Anna, Org. Lett., 2004, 6, 441-443; P. Ferreira, W. Hayes, E. Phillips, D. Rippon and S. Chi Tsang, Green Chem., 2004, 6, 310-312; C. Tanyeli and A. Gümüs, Tetrahedron Lett., 2003, 44, 1639-1642; R. Ciriminna, C. Bolm, T. Fey and M. Pagliaro, Adv. Synth. Catal., 2002, 344, 159-163; T. Fey, H. Fischer, S. Bachmann, K. Albert and C. Bolm, J. Org. Chem., 2001, 66, 8154-8159; A. Dijksman, I. W. C. E. Arends and R. A. Sheldon, Chem. Commun., 2000, 271-272; C. Bolm and T. Fey, Chem. Commun., 1999, 1795-1796.
18. G. Pozzi, M. Cavazzini, S. Quid, M. Benaglia and G. Dell'Anna, Org. Lett., 2004, 6, 441-443; P. Ferreira, W. Hayes, E. Phillips, D. Rippon and S. Chi Tsang, Green Chem., 2004, 6, 310-312; C. Tanyeli and A. Gümüs, Tetrahedron Lett., 2003, 44, 1639-1642; R. Ciriminna, C. Bolm, T. Fey and M. Pagliaro, Adv. Synth. Catal., 2002, 344, 159-163; T. Fey, H. Fischer, S. Bachmann, K. Albert and C. Bolm, J. Org. Chem., 2001, 66, 8154-8159; A. Dijksman, I. W. C. E. Arends and R. A. Sheldon, Chem. Commun., 2000, 271-272; C. Bolm and T. Fey, Chem. Commun., 1999, 1795-1796.
19. F. Minisci, F. Recupero, M. Rodinò, M. Sala and A. Schneider, Org. Proc. Res. Dev., 2003, 7, 794-798; D. Brunel, F. Fajula, J. B. Nagy, B. Deroide, M. J. Verhoef, L. Veum, J. A. Peters and H. van Bekkum, Appl. Catal. A: Gen., 2001, 213, 73-82.
20. F. Minisci, F. Recupero, M. Rodinò, M. Sala and A. Schneider, Org. Proc. Res. Dev., 2003, 7, 794-798; D. Brunel, F. Fajula, J. B. Nagy, B. Deroide, M. J. Verhoef, L. Veum, J. A. Peters and H. van Bekkum, Appl. Catal. A: Gen., 2001, 213, 73-82.
21. S. Collard, C. F. J. Barnard, S. Bennett, S. H. Elgafi, G. R. Henderson, G. Sweeney and M. Sundell, Catalysis for Organic Reactions, (Proceedings 19th ORCS Conference), Marcel Dekker, New York, 2002, pp. 49-60; S. Buckley, Speciality Chemicals, October 2002, pp. 12-13; J.-A. A. Nasman and R. T. Peltonen, EP629441.
22. S. Collard, C. F. J. Barnard, S. Bennett, S. H. Elgafi, G. R. Henderson, G. Sweeney and M. Sundell, Catalysis for Organic Reactions, (Proceedings 19th ORCS Conference), Marcel Dekker, New York, 2002, pp. 49-60; S. Buckley, Speciality Chemicals, October 2002, pp. 12-13; J.-A. A. Nasman and R. T. Peltonen, EP629441.
23. S. Collard, C. F. J. Barnard, S. Bennett, S. H. Elgafi, G. R. Henderson, G. Sweeney and M. Sundell, Catalysis for Organic Reactions, (Proceedings 19th ORCS Conference), Marcel Dekker, New York, 2002, pp. 49-60; S. Buckley, Speciality Chemicals, October 2002, pp. 12-13; J.-A. A. Nasman and R. T. Peltonen, EP629441.