Hydroperoxidation of tertiary alkylaromatics catalyzed by N-hydroxyphthalimide and aldehydes under mild conditions

Advanced Synthesis and Catalysis

Volumn 353, Issue 1, 2011, Pages 147-154

  Melone, Lucio ^a   Gambarotti, Cristian ^a   Prosperini, Simona ^a   Pastori, Nadia ^a   Recupero, Francesco ^a   Punta, Carlo ^a  

^a POLITECNICO DI MILANO   (Italy)

Author keywords

autoxidation; co oxidation; cumene; hydroperoxides; N hydroxyphthalimide

Indexed keywords

EID: 79251508660     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000786     Document Type: Article

References (72)

1. P. R. Schreiner, A. A. Fokin, Chem. Rec. 2004, 3, 247-257
2. E. N. Jacobson, Adv. Synth. Catal. 2004, 346, 109
3. M. Beller, Adv. Synth. Catal. 2004, 346, 107-108
4. U. Schuchardt, D. Cardoso, R. Sercheli, R. Pereira, R. S. da Cruz, M. C. Guerreiro, D. Mandelli, E. V. Spinacé, E. L. Pires, Appl. Catal. A 2001, 211, 1-17
5. I. Hermans, E. S. Spier, U. Neuenschwander, N. Turrà , A. Baiker, Top. Catal. 2009, 52, 1162-1174
6. I. Hermans, J. Peeters, P. Jacobs, Top. Catal. 2008, 50, 124-132.
7. T. Punniyamurthy, S. Velusamy, J. Iqbal, Chem. Rev. 2005, 105, 2329-2363
8. A. K. Suresh, M. M. Sharma, T. Sridhar, Ind. Eng. Chem. Res. 2000, 39, 3958-3997
9. C. I. Herrerias, X. Q. Yao, Z. P. Li, Chem. Rev. 2007, 107, 2546-2562
10. A. A. Fokin, P. R. Schreiner, Adv. Synth. Catal. 2003, 345, 1035-1052
11. J. M. Thomas, R. Raja, Chem. Commun. 2001, 8, 675-687
12. F. Minisci, F. Recupero, G. F. Pedulli, J. Mol. Catal. A: Chem. 2003, 204-205, 63-90.
13. R. A. Sheldon, J. K. Kochi, in: Metal Catalyzed Oxidations of Organic Compunds, Academic Press, New York, 1981, pp 18-25, 38-41
14. E. T. Denisov, I. B. Afanas'ev, in: Oxidation and Antioxidants in Organic Chemistry and Biology, Taylor & Francis Group, Boca Raton, 2005, pp 23-72, 359-382.
15. H. Hock, S. Lang, Ber. Desch. Chem. Ges. 1944, B 77, 257-264
16. W. Jordan, H. van Barneveld, O. Gerlich, M. K. Boymann, J. Ullrich, Ullmann's Encyclopedia of Industrial Organic Chemicals, Wiley-VCH, Weinheim, 1985, Vol. A9, pp 299-312.
17. C. Punta, C. Gambarotti, in: Ideas in Chemistry and Molecular Sciences: Advances in Synthetic Chemistry, (Ed.:, B. Pignataro,), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2010, pp 3-24
18. F. Recupero, C. Punta, Chem. Rev. 2007, 107, 3800-3842
19. F. Minisci, C. Punta, F. Recupero, J. Mol. Catal. A: Chem. 2006, 251, 129-149
20. Y. Ishii, S. Sakaguchi, Catal. Today 2006, 117, 105-113
21. Y. Ishii, S. Sakaguchi, in: Modern Oxidation Methods, (Ed.:, J.-E. Bäckvall,), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2005, pp 119-164
22. Y. Ishii, S. Sakaguchi, T. Iwahama, Adv. Synth. Catal. 2001, 343, 393-427
23. R. A. Sheldon, I. W. C. E. Arends, Adv. Synth. Catal. 2004, 346, 1051-1071
24. C. Galli, P. Gentili, O. Lanzalunga, Angew. Chem. 2008, 120, 4868
25. Angew. Chem. Int. Ed. 2008, 47, 4790 -4796
26. S. Coseri, Catal. Rev. 2009, 51:2, 218-292
27. S. Coseri, Mini-Rev. Org. Chem. 2008, 5, 222-227.
28. For some examples on selective oxidations see: F. Minisci, C. Punta, F. Recupero, F. Fontana, G. F. Pedulli, J. Org. Chem. 2002, 67, 2671-2676
29. F. Minisci, F. Recupero, C. Punta, C. Guidarini, F. Fontana, G. F. Pedulli, Synlett 2002, 7, 1173-1175
30. F. Minisci, F. Recupero, C. Gambarotti, C. Punta, R. Paganelli, Tetrahedron Lett. 2003, 44, 6919-6922
31. A. Shibamoto, S. Sakaguchi, Y. Ishii, Org. Process Res. Dev. 2000, 4, 505-508
32. O. Fukuda, S. Sakaguchi, Y. Ishii, Tetrahedron Lett. 2001, 42, 3479-3481.
33. For some examples on selective functionalizations see: F. Minisci, F. Recupero, C. Punta, C. Gambarotti, F. Antonietti, F. Fontana, G. F. Pedulli, Chem. Commun. 2002, 2496-2497
34. F. Minisci, F. Recupero, A. Cecchetto, C. Punta, C. Gambarotti, F. Fontana, G. F. Pedulli, J. Heterocycl. Chem. 2003, 40, 325-328
35. F. Minisci, O. Porta, F. Recupero, C. Gambarotti, R. Paganelli, G. F. Pedulli, F. Fontana, Tetrahedron Lett. 2004, 45, 1607-1609
36. O. Tayama, T. Iwahama, S. Sakaguchi, Y. Ishii, Eur. J. Org. Chem. 2003, 2286-2289
37. N. Sawatari, S. Sakaguchi, Y. Ishii, Tetrahedron Lett. 2003, 44, 2053-2056
38. K. Hirano, S. Sakaguchi, Y. Ishii, Tetrahedron Lett. 2002, 43, 3617-3620
39. S. Tsujimoto, T. Iwahama, S. Sakaguchi, Y. Ishii, Chem. Commun. 2001, 2352-2353.
40. F. Minisci, C. Punta, F. Recupero, F. Fontana, G. F. Pedulli, Chem. Commun. 2002, 688-689
41. R. Amorati, M. Lucarini, V. Mugnaini, G. F. Pedulli, F. Minisci, F. Recupero, F. Fontana, P. Astolfi, L. Greci, J. Org. Chem. 2003, 68, 1747-1754.
42. F. Minisci, F. Recupero, A. Cecchetto, C. Gambarotti, C. Punta, R. Paganelli, Org. Process Res. Dev. 2004, 8, 163-168.
43. B. Orliåska, Tetrahedron Lett. 2010, 51, 4100-4102.
44. X. Yang, L. Zhou, Y. Chen, C. Chen, Y. Su, H. Miao, J. Xu, Catal. Commun. 2009, 11, 171-174.
45. G. Zheng, C. Liu, Q. Wang, M. Wang, G. Yang, Adv. Synth. Catal. 2009, 351, 2638-2642.
46. G. Y. Yang, Y. F. Ma, J. Xu, J. Am. Chem. Soc. 2004, 126, 10542
47. G. Yang, Q. Zhang, H. Miao, Z. Tong, J. Xu, Org. Lett. 2005, 7, 263-266
48. Q. H. Zhang, C. Chen, H. Ma, H. Miao, W. Zhang, Z. Q. Sun, J. Xu, J. Chem. Technol. Biotechnol. 2008, 83, 1364 -1369
49. L. Zhou, Y. Chen, X. Yang, Y. Su, W. Zhang, J. Xu, Catal. Lett. 2008, 125, 154-159
50. X. Yang, Y. Wang, L. Zhou, C. Chen, W. Zhang, J. Xu, J. Chem. Technol. Biotechnol. 2010, 85, 564-568.
51. X. Tong, J. Xu, H. Miao, Adv. Synth. Catal. 2005, 347, 1953.
52. Z. Du, Z. Sun, W. Zhang, H. Miao, H. Ma, J. Xu, Tetrahedron Lett. 2009, 50, 1677-1680.
53. K. Matsunaka, T. Iwahama, S. Sakaguchi, Y. Ishii, Tetrahedron Lett. 1999, 40, 2165-2168.
54. Y. Aoki, N. Hirai, S. Sakaguchi, Y. Ishii, Tetrahedron 2005, 61, 10995-10999
55. Y. Aoki, S. Sakaguchi, Y. Ishii, Adv. Synth. Catal. 2004, 346, 199-202
56. I. W. C. E. Arends, M. Sasidharan, A. Kühnle, M. Duda, C. Jost, R. A. Sheldon, Tetrahedron 2002, 58, 9055-9061.
57. F. Minisci, C. Gambarotti, M. Pierini, O. Porta, C. Punta, F. Recupero, M. Lucarini, V. Mugnaini, Tetrahedron Lett. 2006, 47, 1421-1424.
58. K. Kaneda, S. Haruna, T. Imanaka, M. Hamamoto, Y. Nishiyama, Y. Ishii, Tetrahedron Lett. 1992, 33, 6827-6830
59. K. Kaneda, S. Ueno, T. Imanaka, E. Shimotsuma, Y. Nishiyama, Y. Ishii, J. Org. Chem. 1994, 59, 2915
60. A. Bravo, F. Fontana, F. Minisci, A. Serri, Chem. Commun. 1996, 1843-1844.
61. C. Einhorn, J. Einhorn, C. Marcadal, J.-L. Pierre, Chem. Commun. 1997, 447-448.
62. F. Minisci, O. Porta, F. Recupero, C. Punta, C. Gambarotti, M. Pierini, Patent WO2008037435, 2008
63. F. Minisci, O. Porta, C. Punta, F. Recupero, C. Gambarotti, R. Spaccini, Patent WO2009115275, 2009.
64. C. Punta, D. Moscatelli, O. Porta, F. Minisci, C. Gambarotti, M. Lucarini, in: Mechanisms in Homogeneous and Heterogeneous Epoxidation Catalysis, (Ed.:, S. T. Oyama,), Elsevier, Amsterdam, The Netherlands, 2008, pp 217-229.
65. C. Chatgilialoglu, D. Crich, M. Komatsu, I. Ryu, Chem. Rev. 1 999, 99, 1991- 2070
66. T. Punniyamurthy, B. Bhatia, J. Iqbal, J. Org. Chem. 1994, 59, 850-853.
67. I. Hermans, L. Vereecken, P. A. Jacobs, J. Peeters, Chem. Commun. 2004, 1140-1141
68. I. Hermans, P. A. Jacobs, J. Peeters, Phys. Chem. Chem. Phys. 2007, 9, 686-690
69. I. Hermans, P. A. Jacobs, J. Peeters, Phys. Chem. Chem. Phys. 2008, 10, 1125-1132.
70. D. L. Boger, R. S. Coleman, J. Org. Chem. 1986, 51, 5436-5439.
71. W. Jordan, H. Barneveld, O. van Gerlich, M. Kleine-Boymann, J. Ullrich, Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 1991, Vol. A 19, p 307.
72. A. G. Davies, R. V. Foster, A. M. White, J. Chem. Soc. 1953 1541-1547.