Nitroxyl radical TEMPO: An organocatalyst for highly efficient and selective oxidation of alcohol

Progress in Chemistry

Volumn 19, Issue 11, 2007, Pages 1727-1735

  Yang, Guanyu ^a   Guo, Yanchun ^a   Wu, Guanghui ^a   Zheng, Liwen ^a   Song, Maoping ^a  

^a ZHENGZHOU UNIVERSITY   (China)

Author keywords

Alcohols; Catalysts; Oxidation reaction; TEMPO

Indexed keywords

EID: 37149001745     PISSN: 1005281X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (100)

1. Zhan B Z, Thompson A. Tetrahedron, 2004, 60: 2917-2935
2. Ten Brink G J, Arends I W C E, Sheldon R A. Science, 2000, 287: 1636-1639
3. Guan B T, Xing D, Shi Z J, et al. J. Am. Chem. Soc., 2005, 127: 18004-18005
4. Sheldon R A, Arends I W C E, Dijksman A. Catalysis Today, 2000, 57: 157-166
5. Mallat T, Baiker A. Chem. Rev., 2004, 104: 3037-3058
6. Enache D I, Edwards J K, Hutchings G J, et al. Science, 2006, 311: 362-364
7. Son Y C, Makwana V D, Suib S L, et al. Angew. Chem. Int. Ed., 2001, 40: 4280-4083
8. Musawir M, Davey P N, Kozhevnikov I V, et al. Chem. Commun., 2003, 1414-1415
9. Krishnaveni N S, Surendra K, Rao K R. Adv. Synth. Catal., 2004, 346: 346-350
10. Edegger K, Mang H, Kroutil W, et al, J. Mol. Catal. A: Chem., 2006, 251: 66-70
11. Csjernyik G, Éll A H, Báckvall J E, et al. J. Org. Chem., 2002, 67: 1657-1662
12. Adam W, Saha-Möller C R, Ganeshpure P A. Chem. Rev., 2001, 101: 3499-3548
13. De Nooy A E J, Besemer A C, van Bekkum H, Synthesis, 1996, 1153-1176
14. Sheldon R A, Arends I W C E. Adv. Synth. Catal., 2004, 346: 1051-1071
15. Sheldon R A, Arends I W C E. J. Mol. Catal. A: Chem., 2006, 251: 200-214
16. Sheldon R A, Arends I W C E, Brink G J T. Acc. Chem. Res., 2002, 35: 774-781
17. Calderon F. Synlett, 2006, 657-658
18. Minisci F, Punta C, Recupero F. J. Mol. Catal. A: Chem., 2006, 251: 129-149
19. Minisci F, Recupero F, Pedulli G F, et al. J. Mol. Catal. A: Chem., 2003, 204/205: 63-90
20. Caron S, Dugger R W, Ripin D H B, et al. Chem. Rev., 2006, 106: 2943-2989
21. Bjørsvik H R, Uguori L, Minisci F, et al. Org. Proc. Res. Dev., 2002, 6: 197-200
22. Fritz-Langhals E. Org. Proc. Res. Develop., 2005, 9: 577-582
23. Bragd P L, van Bekkum H, Besemer A C. Topics Catal., 2004, 27: 49-66
24. Mahoney L R, Mendenhall G D, lngold K U. J. Am, Chem. Soc., 1973, 95: 8610-8614
25. Ganiev I M, Timerghazin Q K, Khalizov A F, et al. J. Phys. Org. Chem., 2001, 14: 38-42
26. .Minisci F, Recupero F, Cecchetto A, et al. Eur. J. Org. Chem., 2004, 109-119
27. Ma Z K, Bobbin J M. J. Org. Chem., 1991, 56: 6110-6114
28. Golubev V A, Rozantsev E G, Neiman M B. Bull. Acad. Sci. USSR, Chem. Ser., 1965, 14: 1898
29. Rychovsky S D, Vaidyanathan R. J. Org. Chem., 1999, 64: 310-312
30. Bolm C, Magnus A S, Hildebrand J P. Org. Lett., 2000, 2: 1173-1175
31. Hunter D H, Barton D H R, Motherwell W J. Tetrahedron Lett., 1984, 25: 603-606
32. Kim S S, Nehru K. Synlett, 2002, 616-618
33. De Luca L, Giacomelli G, Masala S, Porcheddu A. J. Org. Chem., 2003, 68: 4999-5001
34. De Luca L, Giacomelli G, Porcheddu A. Org. Lett., 2001, 3: 3041-3043
35. Semmelhack M F, Chou C S, Cortes D A. J. Am. Chem. Soc., 1983, 105: 4492-4494
36. Palmisano G, Ciriminna R, Pagliaro M. Adv. Synth. Catal., 2006, 348: 2033-2037
37. Anelli P L, Biffi C, Montanari F, Quici S. J. Org. Chem., 1987, 52: 2559-2562
38. Anelli P L, Banfi S, Montanari F, Quici S. J. Org. Chem., 1989, 54: 2970-2972
39. Anelli P L, Montanari F, Quici S. Org. Synth., 1990, 69: 212-219
40. Lin F, Peng W, Yu B, et al. Carbohydr. Res., 2004, 339: 1409-1409
41. Zhao M Z, U J, Mano E, Reider P J, et al. J. Org. Chem., 1999, 64: 2564-2566
42. Melvin F, MeNeill A, Herbert R B, et al. Tetrahedron Lett., 1999, 40: 1201-1202
43. Semmelhack M F, Schmid C R, Cortés D A, et al. J. Am. Chem. Soc., 1984, 106: 3374-3376
44. Betzemeier B, Cavazzini M, Knochel P, et al. Tetrahedron Lett., 2000, 41: 4343-4346
45. Ragagnin G, Betzemeier B, Knochel P, et al. Tetrahedron, 2002, 58: 3985-3991
46. Gamez P, Arends I W C E, Sheldon R A, et al. Chem. Commun., 2003, 2414-2415
47. Gamez P, Arends I W C E, Sheldon R A, et al. Adv. Synth. Catal., 2004, 346: 805-811
48. Striegler S. Tetrahedron, 2006, 62: 9109-9114
49. Jiang N, Ragauskas A J. J. Org. Chem., 2006, 71: 7087-7090
50. Jiang N, Ragauskas A J. Org. Lett., 2005, 7: 3689-3692
51. Velusamy S, Srinivasan A, Punniyamurthy T. Tetrahedron Lett., 2006, 47: 923-926
52. Boudreau J, Doucette M, Ajjou A N. Tetrahedron Lett., 2006, 47: 1695-1698
53. Velusamy S, Punniyamurthy T. Eur. J. Org. Chem., 2003, 3913-3915
54. Cecchetto A, Fontana F, Miniscia F, et al. Tetrahedron Lett., 2001, 42: 6651-6653
55. Dijksman A, Arends I W C E, Sheldon R A. Chem. Commun., 1999, 1591-1592
56. Dijksman A, Arends I W C E, Sheldon R A, et al, J. Am. Chem. Soc., 2001, 123: 6826-6833.
57. Kim S S, Jung H C. Synthesis, 2003, 2135-2137
58. Wang N W, Liu R H, Uang X M, et al. Chem. Commun., 2005, 5322-5324
59. Yang G Y, Ma J P, Wang W, et al. Catal. Lett., 2006, 112: 83-87
60. Lenoir D. Angew. Chem. Int. Ed., 2006, 45: 3206-3210
61. Liu R H, Liang X M, Hu X Q, et al. J. Am. Chem. Soc, 2004, 126: 4112-4113
62. Liu R H, Liang X M, Hu X Q, et al. J. Org. Chem., 2005, 70: 729-731
63. Xie Y, Mo W M, Hu X Q, et al. J. Org. Chem., 2007, 72: 4288-4291
64. Miller R A, Hoermer R S. Org. Lett., 2003, 5: 285-287
65. Lei M, Hu R J, Wang Y G. Tetrahedron, 2006, 62: 8928-8932
66. Vatele J M. Synlett, 2006, 2055-2058
67. Schulze A, Giannis A. Synthesis, 2006, 257-260
68. De Mico A, Margarita R, Piancatelli G, et al. J. Org. Chem., 1997, 62: 6974-6977
69. Vatèle J M. Tetrahedron Lett., 2006, 47: 715-718
70. Tashino Y, Togo H. Synlett, 2004, 2010-2012
71. Sakuratani K, Togo H. Synthesis, 2003, 21-23
72. Herrerlas C I, Zhang T Y, Li C J. Tetrahedron Lett., 2006, 47: 13-17
73. Fabbrini M, Galli C, Macchitella D, et al. Tetrahedron Lett., 2001, 42: 7551-7553
74. Baiocco P, Barreca A M, Galli C, et al. Org. Biomol. Chem., 2003, 1: 191-197
75. Galli C, Gentili P. J. Phys. Org. Chem., 2004, 17: 973-977
76. Fabbrini M, Galli C, Gentili P J. Mol. Catal, B: Enz., 2002, 16: 231-240
77. Arendsl W C E, Li Y X, Sheldon R A, et al. Tetrahedron, 2006, 62: 6659-6665
78. Kulys J, Vidziunaite R. J. Mol. Catal. B: Enz., 2005, 37: 79-83
79. Ciriminna R, Bolm C, Pagliaro M, et al. Adv. Synth. Catal., 2002, 344: 159-163
80. Bolm C, Fey T. Chem. Commun., 1999, 1795-1796
81. Testa M L, Ciriminna R, Pagliaro M, et al. Adv. Synth. Catal., 2004, 346: 655-660
82. Ciriminna R, Pagliaro M. Adv. Synth. Catal., 2003, 345: 383-388
83. Ciriminna R, Blum J, Avnir D, Pagliaro M. Chem. Commun., 2000, 1441-1442
84. Brunei D, Fajula F, Nagy J B, et al. Appl. Catal. A: Gen., 2001, 213: 73-82
85. Brunei D. Lentz P, Sutra P, et al. Stud. Surf. Sci. Catal., 1999, 125: 237-244
86. Dijksman A, Arends I W C E, Sheldon R A. Chem. Commun., 2000, 271-272
87. Dijksman A, Arends I W C E, Sheldon R A. Synlett, 2001, 102-104
88. Minisci F, Recupero F, Rodino M, et al. Org. Process Res. Dev., 2003, 7: 794-798
89. Ferreira P, Hayes W, Tsang S C, et al. Green Chem., 2004, 6: 310-312
90. Benaglia M, Puglisi A, Pozzi G, et al. Tetrahedron, 2005, 61: 12058-12064
91. Pozzi G, Cavazzini M, Quici S, et al. Org. Lett., 2004, 6: 441-443
92. Cozzi F. Adv. Synth. Catal., 2006, 348: 1367-1390
93. Gilhespy M, Lok M, Baucherei X. Catal. Today, 2006, 117: 114-119
94. Gilhespy M, Lok M, Baucherei X. Chem. Commun., 2005, 1085-1086
95. Tanyeli C, Gumita A. Tetrahedron Lett., 2003, 44: 1639-1642
96. Kashiwagi Y, Ikezoe H, Ono T. Synlett, 2006, 69-72
97. Wu X E, Ma L, Gao L X, et al. Synlett, 2005, 607-610
98. Holczknecht O, Cavazzini M, Pozzi G, et al. Adv. Synth. Catal., 2005, 347: 677-688
99. Pozzi G, Cavazzini M, Holczknecht O, et al. Tetrahedron Lett., 2004, 45: 4249-4251
100. Gheorghe A, Cuevas-Yanez E, Reiser O, et al. Synlett, 2006, 2767-2770