Magnetic Polystyrene Nanosphere Immobilized TEMPO: A Readily Prepared, Highly Reactive and Recyclable Polymer Catalyst in the Selective Oxidation of Alcohols

ChemCatChem

Volumn 5, Issue 1, 2013, Pages 307-312

  Zheng, Zhi ^a   Wang, Jianli ^a   Zhang, Miao ^a   Xu, Lixin ^a   Ji, Jianbing ^a  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Alcohols; Heterogeneous catalysis; Magnetic properties; Nanostructures; Oxidation

Indexed keywords

2 ,2 ,6 ,6-TETRAMETHYLPIPERIDINE-1-OXYL; MAGNETIC POLYSTYRENE; MAGNETIC RESPONSE; RAPID SEPARATION; RECYCLABLE CATALYST; RECYCLABLE POLYMERS; SELECTIVE OXIDATION; TEMPO RADICAL;

ALCOHOLS; CATALYSIS; CATALYSTS; LEACHING; MAGNETIC PROPERTIES; NANOSPHERES; NANOSTRUCTURES; POLYSTYRENES; RECYCLING;

OXIDATION;

EID: 84871654358     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201200459     Document Type: Article

References (54)

1. C. Ó. Dálaigh, S. A. Corr, Y. Gun′ko, S. J. Connon, Angew. Chem. 2007, 119, 4407-4410; Angew. Chem. Int. Ed. 2007, 46, 4329-4332.
2. V. A. Golubev, E. G. Rozantsev, M. B. Neiman, Bull. Acad. Sci. USSR 1965, 14, 1898-1904.
3. P. L. Anelli, C. Biffi, F. Montanari, S. Quici, J. Org. Chem. 1987, 52, 2559-2562.
4. R. A. Sheldon, I. W. C. E. Arends, Adv. Synth. Catal. 2004, 346, 1051-1071;
5. A. E. J. deNooy, A. C. Besemer, H. vanBekkum, Synthesis 1996, 1153-1176;
6. C. B. Qiu, L. Q. Jin, Z. L. Huang, Z. Q. Tang, A. W. Lei, Z. L. Shen, N. Sun, W. M. Mo, B. X. Hu, X. Q. Hu, ChemCatChem 2012, 4, 76-80;
7. S. S. Wang, Z. Popovic, H. H. Wu, Y. Liu, ChemCatChem 2011, 3, 1208-1213;
8. S. A. Tromp, I. Matijosyte, R. A. Sheldon, I. W. C. E. Arends, G. Mul, M. T. Kreutzer, J. A. Moulijn, S. deVries, ChemCatChem 2010, 2, 827-833.
9. For recent interesting reviews on supported TEMPO radicals, see:
10. L. Tebben, A. Studer, Angew. Chem. 2011, 123, 5138-5174; Angew. Chem. Int. Ed. 2011, 50, 5034-5068;
11. F. Cozzi, Adv. Synth. Catal. 2006, 348, 1367-1390;
12. M. Benaglia, A. Puglisi, F. Cozzi, Chem. Rev. 2003, 103, 3401-3429.
13. C. Röben, A. Studer, W. L. Hemme, H. Eckert, Synlett 2010, 7, 1110-1114.
14. B. Karimi, E. Badreh, Org. Biomol. Chem. 2011, 9, 4194-4198;
15. L. Di, Z. Hua, Adv. Synth. Catal. 2011, 353, 1253-1259;
16. B. Karimi, A. Biglari, J. H. Clark, V. Budarin, Angew. Chem. 2007, 119, 7348-7351; Angew. Chem. Int. Ed. 2007, 46, 7210-7213;
17. T. Fey, H. Fischer, S. Bachmann, K. Albert, C. Bolm, J. Org. Chem. 2001, 66, 8154-8159;
18. D. Brunel, F. Fajula, J. B. Nagy, B. Deroide, M. J. Verhoef, L. Veum, J. A. Peters, H. vanBekkum, Appl. Catal. A 2001, 213, 73-82.
19. A. Michaud, V. Pandarus, L. Tremblay, R. Ciriminna, M. Pagliaro, F. Béland, Top Catal. 2010, 53, 1110-1113;
20. M. L. Testa, R. Ciriminna, C. Hajji, E. Z. Garcia, M. Ciclosi, J. S. Arques, M. Pagliaro, Adv. Synth. Catal. 2004, 346, 655-660;
21. R. Ciriminna, M. Pagliaro, Adv. Synth. Catal. 2003, 345, 383-388;
22. R. Ciriminna, C. Bolm, T. Fey, M. Pagliaro, Adv. Synth. Catal. 2002, 344, 159-163;
23. R. Ciriminna, J. Blum, D. Avnir, M. Pagliaro, Chem. Commun. 2000, 1441-1442;
24. C. Bolm, T. Fey, Chem. Commun. 1999, 1795-1796.
25. M. A. Subhani, M. Beigi, P. Eilbracht, Adv. Synth. Catal. 2008, 350, 2903-2909;
26. A. Gheorghe, A. Matsuno, O. Reiser, Adv. Synth. Catal. 2006, 348, 1016-1020;
27. Y. Kashiwagi, H. Ikezoe, T. Ono, Synlett 2006, 0069-0072;
28. T. Y. S. But, Y. Tashino, H. Togo, P. H. Toy, Org. Biomol. Chem. 2005, 3, 970-971;
29. M. Gilhespy, M. Lok, X. Baucherel, Chem. Commun. 2005, 1085-1086;
30. S. Weik, G. Nicholson, G. Jung, J. Rademann, Angew. Chem. 2001, 113, 1489-1492; Angew. Chem. Int. Ed. 2001, 40, 1436-1439.
31. M. Gilhespy, M. Lok, X. Baucherel, Catal. Today 2006, 117, 114-119.
32. A. Dijksman, I. W. C. E. Arends, R. A. Sheldon, Chem. Commun. 2000, 271-272.
33. P. Ferreira, E. Phillips, D. Rippon, S. C. Tsang, Appl. Catal. B 2005, 61, 206-221;
34. P. Ferreira, E. Phillips, D. Rippon, S. C. Tsang, W. Hayes, J. Org. Chem. 2004, 69, 6851-6859;
35. P. Ferreira, W. Hayes, E. Phillips, D. Rippon, S. C. Tsang, Green Chem. 2004, 6, 310-312.
36. M. Benaglia, A. Puglisia, O. Holczknechtb, S. Quici, G. Pozzi, Tetrahedron 2005, 61, 12058;
37. C. W. Y. Chung, P. H. Toy, J. Comb. Chem. 2007, 9, 115.
38. O. Holczknecht, G. Pozzi, S. Quici, QSAR Comb. Sci. 2006, 25, 736-741;
39. O. Holczknecht, M. Cavazzini, S. Quici, I. Shepperson, G. Pozzi, Adv. Synth. Catal. 2005, 347, 677-688;
40. G. Pozzi, M. Cavazzini, O. Holczknecht, S. Quici, I. Shepperson, Tetrahedron Lett. 2004, 45, 4249-4251.
41. A. Gheorghe, E. Cuevas-Yañez, J. Horn, W. Bannwarth, B. Narsaiah, O. Reiser, Synlett 2006, 17, 2767-2770.
42. X. E. Wu, L. Ma, M. X. Ding, L. X. Gao, Synlett 2005, 0607-0610.
43. For recent interesting reviews, see:
44. V. Polshettiwar, R. Luque, A. Fihri, H. B. Zhu, M. Bouhrara, J. M. Bassett, Chem. Rev. 2011, 111, 3036-3075;
45. C. W. Lim, I. S. Lee, Nano Today 2010, 5, 412-434;
46. Y. H. Zhu, L. P. Stubbs, F. Ho, R. Z. Liu, C. P. Ship, J. A. Maguire, N. S. Hosmane, ChemCatChem 2010, 2, 365-374;
47. A. Schätz, O. Reiser, W. J. Stark, Chem. Eur. J. 2010, 16, 8950-8967;
48. S. Shylesh, V. Schünemann, W. R. Thiel, Angew. Chem. 2010, 122, 3504-3537; Angew. Chem. Int. Ed. 2010, 49, 3428-3459;
49. A. H. Lu, E. L. Salabas, F. Schüth, Angew. Chem. 2007, 119, 1242-1266; Angew. Chem. Int. Ed. 2007, 46, 1222-1244.
50. A. Schätz, R. N. Grass, W. J. Stark, O. Reiser, Chem. Eur. J. 2008, 14, 8262-8266.
51. A. K. Tucker-Schwartz, R. L. Garrell, Chem. Eur. J. 2010, 16, 12718-12726.
52. I. Csetneki, M. K. Faix, A. Szilágyi, A. L. Kovács, Z. Németh, M. Zrinyi, J. Polym. Sci. Part A 2004, 42, 4802-4808;
53. For a detailed experimental procedure, see the supporting information.
54. Z. Zheng, M. Luo, J. E. Yu, J. L. Wang, J. B. Ji, Ind. Eng. Chem. Res. 2012, 51, 3715-3721.