Controlling iron-catalyzed oxidation reactions: From non-selective radical to selective non-radical reactions

Chemistry - A European Journal

Volumn 14, Issue 29, 2008, Pages 8793-8797

  Shi, Feng ^a   Tse, Man Kin ^a   Li, Zuopeng ^b   Beller, Matthias ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

Fenton chemistry; Heterogeneous catalysis; Iron; pH control; Radicals

Indexed keywords

CATALYSIS; CATALYST ACTIVITY; CATALYST SELECTIVITY; CATALYTIC OXIDATION; CHEMICAL OXYGEN DEMAND; CHEMISTRY; CONCENTRATION (PROCESS); FUNCTIONAL GROUPS; OXIDATION; PH; PH EFFECTS; PROTONS; REACTION KINETICS;

BUFFER SYSTEMS; CATALYTIC PERFORMANCES; CATALYZED OXIDATIONS; CATALYZED REACTIONS; FENTON CHEMISTRY; HETEROGENEOUS CATALYSIS; HIGH SELECTIVITIES; OXIDATION CHEMISTRIES; PH CONTROL; PH VALUES; PROTON CONCENTRATIONS; RADICAL PATHWAYS; RADICAL REACTIONS; RADICALS; SELECTIVE OXIDATIONS; SWITCHABLE;

REDOX REACTIONS;

BENZYL ALCOHOL; FREE RADICAL; IRON;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION;

BENZYL ALCOHOL; CATALYSIS; FREE RADICALS; IRON; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 55049110729     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801432     Document Type: Article

References (78)

1. E. V. Mielczarek. S. B. McGrayne. E. V. Mielczarek, S. B. McGrayne, Iron, Nature's Universal Element: Why People Need Iron & Animals Make Magnets, Rutgers University Press. New Brunswick, N.J., 2000.
2. R. M. Cornell, U. Schwertmann, The iron oxide: structures, properties, occurences and uses, Wiley-VCH, Weinheim, 2003.
3. C. Bolm, J. Legros, J. Le Paih, L. Zani, Chem. Rev. 2004, 104, 6217-6254.
4. M. Costas, K. Chen, L. Que, Jr., Coord. Chem. Rev. 2000, 200-202, 517-544.
5. M. Fontecave, S. MOnage, C. Duboc-Toia, Coord. Chem. Rev. 1998, 178-180, 1555-1572.
6. C. Kim, K. Chen, J. Kim, L. Que, Jr., J. Am. Chem. Soc. 1997, 119, 5964-5965.
7. M. Fujita, M. Costas, L. Que, Jr., J. Am. Chem. Soc. 2003, 125, 9912-9913.
8. P.D. Oldenburg, A. A. Shteinman, L. Que, Jr., J. Am. Chem. Soc. 2005, 127, 15672-15673.
9. J. Legros, C. Bolm, Chem. Eur. J. 2005, 11, 1086-1092.
10. J. Legros, C. Bolm, Angew. Chem. 2004, 116, 4321-4324;
11. Angew. Chem. Int. Ed. 2004, 43, 4225-4228.
12. J. Legros, C. Bolm, Angew. Chem. 2003, 115, 5645-5647;
13. Angew. Chem. Int. Ed. 2003, 42, 5487-5489.
14. G. Cahiez, V. Habiak, C. Duplais, A. Moyeux, Angew. Chem. 2007, 119, 4442-4444;
15. Angew. Chem. Int. Ed. 2007, 46, 4364-4366.
16. M. Nakamura, K. Matsuo, S. Ito, E. Nakamura, J. Am. Chem. Soc. 2004, 126, 3686-3687.
17. A. Fürstner, A. Leitner, M. Méndez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856-13863.
18. T. L. Foster, J. P. Caradonna, J. Am. Chem. Soc. 2003, 125, 3678-3679.
19. R. S. Srivaslava, M. A. Khan, K. M. Nicholas, J. Am. Chem. Soc. 1996, 118, 3311-3312.
20. K. Komeyama, T. Morimoto, K. Takaki, Angew. Chem. 2006, 118, 3004-3007;
21. Angew. Chem. Int. Ed. 2006, 45, 2938-2941.
22. B. Plietker, Angew. Chem. 2006, 118, 1497-1501 ;
23. Angew. Chem. Int. Ed. 2006, 45, 1469-1473.
24. B. Plielker, Angew. Chem. 2006, 118, 6200-6203;
25. Angew. Chem. Int. Ed. 2006, 45, 6053-6056.
26. N. A. Stephenson, A. T. Bell, J. Am. Chem. Soc. 2005, 127, 8635-8643.
27. G. Dubois, A. Murphy, T. D. P. Stack, Org. Lett. 2003, 5, 2469-2472.
28. M. Nakanishi, C. Bolm, Adv. Synth. Catal. 2007, 349, 861-864.
29. S. E. Martín, A. Garrone, Tetrahedron Lett. 2003, 44, 549-552.
30. B. Halliwell, J. M. C. Gutteridge, Free Radicals in Biology and Medicine, 3rd, OUP, Oxford, 1999.
31. D. H. R. Barton, D. K. Taylor, Pure Appl. Chem. 1996, 68, 497-504.
32. D. H. R. Barton, Chem. Soc. Rev. 1996, 25, 237-240.
33. P.A. MacFaul, D. D. M. Wayner, K. U Ingold, Acc. Chem. Res. 1998, 31, 159-162.
34. D. T. Sawyer, A. Sobkowiak, T. Matsushita, Acc. Chem. Res. 1996, 29, 409-416.
35. T. Pacześniak, A. Sobkowiak, J. Mol. Catal. B J. Mol. Catal. A 2003, 194, 1-11.
36. D. Bianchi, R. Bortolo, R. Tassinari, M. Ricci, R. Vignola, Angew. Chem. 2000, 112, 4491-4493;
37. Angew. Chem. Int. Ed. 2000, 39, 4321-4323.
38. S. Ito, A. Mitarai, K. Hikino, M. Hirama, K. Sasaki, J. Org. Chem. 1992, 57, 6937-6941.
39. C. K. Duesterberg, T. D. Waite, Environ. Sci. Technol. 2006, 40, 4189-4195.
40. T. Shiga, J. Phy. Chem. 1965, 69, 3805-3814.
41. S. J. Hug, O. Leupin, Environ. Sci. Technol. 2003, 37, 2734-2742.
42. J. A. Theruvathu, A. R. Flyunt, J. V. Sonntag, C. V. Sonntag, J. Am. Chem. Soc. 2001, 123, 9007-9014.
43. R. G. Zepp, Environ. Sci. Technol. 1992, 26, 313-319.
44. S. H. Bossmann, E. Oliveros, S. Göb, S. Siegwarl, E. P. Dahlen, L. Payawan, Jr, M. Straub, M. Wörner, A. Braun, J. Phys. Chem. A 1998, 102, 5542-5550.
45. C. K. Duesterbergand, T. D. Waite, Environ. Sci. Technol. 2006, 40, 4189-4195.
46. S. Ito, A. Mitarai, K. Hikino, M. Hirama, K. Sasaki, J. Org. Chem. 1992, 57, 6937-6941.
47. a) C. Döbler, G. Mehltretter, M. Beller, Angew. Chem. 1999, 111, 3211-3212;
48. Angew. Chem. Int. Ed. 1999, 38, 3026-3028;
49. b) C. Döbler, G. Mehltretter, U. Sundermeier, M. Beller, J. Am. Chem. Soc. 2000, 122, 10289-10297;
50. c) G. M. Mehltretter, C. Döbler, U. Sundermeier, M. Beller, Tetrahedron Lett. 2000, 41, 8083-8087.
51. a) G. Anilkumar, B. Bitterlich, F. G. Gelalcha, M. K. Tse, M. Beller, Chem. Commun. 2007, 289-291;
52. b) K. Schröder, X. Tong, B. Bitterlich, M. K. Tse, F. G. Gelacha, A. Brückner, M. Beller, Tetrahedron Lett. 2007, 48, 6339-6342.
53. a) I. Iovel, K. Mertins, J. Kischel, A. Zapf, M. Beller, Angew. Chem. 2005, 117, 3981-3985;
54. Angew. Chem. Int. Ed. 2005, 44, 3913-3917;
55. b) J. Kischel, D. Michalik, A. Zapf, M. Beller, Chem. Asian J. 2007, 2, 909-914;
56. c) J. Kischel, K. Mertins, D. Michalik, A. Zapf, M. Beller, Adv. Synth. Catal. 2007, 349, 871-875;
57. d) S. Enthaler, G. Erre, M. K. Tse, K. Junge, M. Beller, Tetrahedron Lett. 2006, 47, 8095-8099;
58. e) S. Enthaler, B. Hagemann, G. Erre, K. Junge, M. Beller, Chem. Asian J. 2006, 1, 598-604;
59. f) J. Kischel, I. Iovel, K. Mertins, A. Zapf, M. Beller, Org. Lett. 2006, 8, 19-22;
60. g) N. S. Shaikh, K. Junge, M. Beller, Org. Lett. 2007, 9, 5429-5432;
61. h) S. Enthaler, B. Spilker, G. Erre, M. K. Tse, K. Junge, M. Beller, Tetrahedron 2008, 64, 3867-3876;
62. i) N. S. Shaikh, S. Enthaler, K. Junge, M. Beller, Angew. Chem. 2008, 120, 2531-2535;
63. Angew. Chem. Int. Ed. 2008, 47, 2497-2501.
64. a) F. G. Gelalcha, B. Bitterlich, G. Anilkumar, M.-K. Tse, M. Beller, Angew. Chem. 2007, 119, 7431-7435;
65. Angew. Chem. Int. Ed. 2007, 46, 7293-7296;
66. b) F. Shi, M. K. Tse, M.-M. Fohl, A. Brückner, S. Zhang, M. Beller, Angew. Chem. 2007, 119, 9022-9024;
67. Angew. Chem. Int. Ed. 2007, 46, 8866-8868.
68. Due to the nature of the solvent free and continuous hydrogen peroxide addition system, it is not convenient to measure the pH value in situ. Therefore, the pH value was determined in a series of model systems at room temperature.
69. 4.
70. obs of benzyl alcohol. See Supporting Information.
71. K. K. Banerji, J. Chem. Soc. Perkin Trans. 2 1973, 435-437.
72. C.-M. Che, W.-T. Tang, W.-O. Lee, K.-Y. Wong, T.-C. Lau, Dalton Trans. 1992, 1551-1556.
73. N. Y. Oh, Y. Suh, M. J. Park, M. S. Seo, J. Kim, W. Nam, Angew. Chem. 2005, 117, 4307-4311;
74. Angew. Chem. Int. Ed. 2005, 44, 4235-4239.
75. R. C. Pratt, T. D. P. Stack, J. Am. Chem. Soc. 2003, 125, 8716-8717.
76. P. Chaudhuri, M. Hess, J. Müller, K. Hildenbrand, E. Bill, T. Weyhermüller, K. Wieghardl, J. Am. Chem. Soc. 1999, 121, 9599-9610.
77. Y. Wang, J. L. DuBois, B. Hedman, K. O. Hodgson, T. D. P. Stack, Science 1998, 279, 537-540.
78. L. Roecker, T. J. Meyer, J. Am. Chem. Soc. 1987, 109, 746-754.