Iron(II, III)-catalyzed oxidative N-dealkylation of amines with dioxygen

Journal of Molecular Catalysis A: Chemical

Volumn 212, Issue 1-2, 2004, Pages 25-33

  Naróg, Dorota ^a   Lechowicz, Urszula ^a   Pietryga, Tadeusz ^a   Sobkowiak, Andrzej ^a  

^a RZESZOW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Alkylated amines; Dioxygen activation; Iron complexes; N dealkylation; N demethylation

Indexed keywords

ACETONITRILE; AMINES; CATALYSTS; CONDENSATION REACTIONS; IRON; OXIDATION;

EQUILIBRIUM REACTIONS; OXYGENATION;

CATALYSIS;

4,4' METHYLENEBIS(N,N DIMETHYLANILINE); ACETONITRILE; ALDEHYDE DERIVATIVE; AMINE; ANILIDE; ANILINE DERIVATIVE; FORMALDEHYDE; FORMANILIDE; IRON COMPLEX; METHYLANILINE; N METHYLANILIDE; N METHYLFORMANILIDE; N,N DIMETHYLANILINE; OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; DEALKYLATION; OXIDATION; POLYMERIZATION;

EID: 1242317734     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2003.11.018     Document Type: Article

References (93)

1. Guengerich F.P., Okazaki O., Seto Y., MacDonald T.L. Xenobiotica. 25:1995;689.
2. Trewick S.C., Henshaw T.F., Hausinger R.P., Lindhal T., Sedgwick B. Nature. 419:2002;174.
3. Sono M., Roach M.P., Coulter E.D., Dawson J.H. Chem. Rev. 96:1996;2841.
4. Miwa G.T., Walsh J.S., Kedderis G.L., Hollenberg P.F. J. Biol. Chem. 258:1983;14445.
5. Kedderis G.L., Hollenberg P.F. J. Biol. Chem. 258:1983;8129.
6. Kedderis G.L., Hollenberg P.F. J. Biol. Chem. 259:1984;3663.
7. Kedderis G.L., Hollenberg P.F. Biochemistry. 24:1985;6158.
8. Guengerich F.P., Yun C.H., Macdonald T.L. J. Biol. Chem. 271:1996;27321.
9. Manchester J.I., Dinnocenzo J.P., Higgins L.A., Jones J.P. J. Am. Chem. Soc. 119:1997;5069.
10. Goto Y., Watanabe Y., Fukuzumi S., Jones J.P., Dinnocenzo J.P. J. Am. Chem. Soc. 120:1998;10762.
11. E. Baciocchi, M.F. Gerini, O. Lanzalunga, A. Lapi, S. Mancinelli, P. Mencarelli, J. Chem. Soc., Chem. Commun. (2000) 393.
12. E. Baciocchi, M.F. Gerini, O. Lanzalunga, A. Lapi, M.G. Lo Piparo, S. Mancinelli, Eur. J. Org. Chem. (2001) 2305.
13. Shaffer C.L., Morton M.D., Hanzlik R.P. J. Am. Chem. Soc. 123:2001;8502.
14. Bhakta M.N., Wimalasena K. J. Am. Chem. Soc. 124:2002;1844.
15. Shaffer C.L., Harriman S., Koen Y.M., Hanzlik R.P. J. Am. Chem. Soc. 124:2002;8268.
16. Que L. Jr., Ho R.Y.N. Chem. Rev. 96:1996;2607.
17. Hover G.G., Kulkarni A.P. Chem. Biol. Interact. 124:2000;191.
18. Shannon P., Bruice T. J. Am. Chem. Soc. 103:1981;4580.
19. Benedini F., Galliani G., Mali M., Rindone B., Tollari S. J. Chem. Soc. Perkin. Trans. II:1985;1963.
20. Dicken C.M., Lu F.L., Nee M.W., Bruice T.C. J. Am. Chem. Soc. 107:1985;5776.
21. J.R. Lindsay Smith, D.N. Mortimer, J. Chem. Soc., Chem. Commun. (1985) 64.
22. Fujimori K., Fujiwara S., Takata T., Oae S. Tetrahedron Lett. 27:1986;581.
23. J.R. Lindsay Smith, D.N. Mortimer, J. Chem. Soc., Perkin Trans. II (1986) 1743.
24. E.I. Karasevich, A.M. Khenkin, A.E. Shilov, J. Chem. Soc., Chem. Comm. (1987) 731.
25. Ostrovic D., Knobler C.B., Bruice T.C. J. Am. Chem. Soc. 109:1987;3444.
26. Murahashi S., Maota T., Yonemura K. J. Am. Chem. Soc. 110:1988;8256.
27. S. Murata, M. Miura, M.J. Nomura, J. Chem. Soc., Chem. Commun. (1989) 116.
28. Sobkowiak A., Sawyer D.T. J. Am. Chem. Soc. 113:1991;9520.
29. S. Murata, K. Suzuki, A. Tamatani, M. Miura, M. Nomura, J. Chem. Soc., Perkin Trans. I (1992) 1387.
30. Murahashi S., Naota T., Miyaguchi N., Nakato T. Tetrahedron Lett. 33:1992;6991.
31. Hage J.P., Schnelten J.R., Sawyer D.T. Bioorg. Med. Chem. 4:1996;821.
32. Kotani E., Takeya T., Shimizu H., Egawa H., Yamamoto T., Tobinaga S. Chem. Pharm. Bull. 45:1997;2089.
33. Baciocchi E., Lanzalunga O., Lapi A., Manduchi L. J. Am. Chem. Soc. 120:1998;5783.
34. Baciocchi E., Lapi A. Tetrahedron Lett. 40:1999;5425.
35. Krohn K., Küpke J. J. Prakt. Chem. 341:1999;509.
36. Fukuzumi S. J. Porphyrins Phthalocyanines. 4:2000;398.
37. Mahapatra S., Halfen J.A., Tolman W.B. J. Am. Chem. Soc. 118:1996;11575.
38. Mahadevan V., Hou Z., Cole A.P., Root D.E., Lal T.K., Solomon E.I., Stack T.D.P. J. Am. Chem. Soc. 119:1997;11996.
39. Lee D., Lippard S.J. J. Am. Chem. Soc. 120:1998;12153.
40. Lee D., Du Bois j., Petasis D., Hendrich M.P., Krebs C., Huynh B.H., Lippard S.J. J. Am. Chem. Soc. 121:1999;9893.
41. Lee D., Lippard S.J. J. Am. Chem. Soc. 123:2001;4611.
42. Lee D., Lippard S.J. Inorg. Chem. 41:2002;827.
43. Taki M., Teramae S., Nagatomo S., Tachi Y., Kitagawa T., Itoh S., Fukuzumi S. J. Am. Chem. Soc. 124:2002;6367.
44. Hall L.R., Iwamoto R.T., Hanzlik R.P. J. Org. Chem. 54:1989;2446.
45. Santamaria J., Ouchabane R., Rigaudy J. Tetrahedron Lett. 30:1989;3977.
46. Gan H., Whitten D.G. J. Am. Chem. Soc. 113:1991;9409.
47. Zhang T., Oyama T., Aoshima A., Hidaka H., Zhao J., Serpone N. J. Phtochem. Photobiol. 140:2001;163.
48. Hall L.R., Hanzlik R.P. J. Biol. Chem. 265:1990;12349.
49. Okazaki O., Guengerich F.P. J. Biol. Chem. 268:1993;1546.
50. Karki S.B., Dinnocenzo J.P., Jones J.P., Korzekwa K.R. J. Am. Chem. Soc. 117:1995;3657.
51. Chen H., de Groot M.J., Vermeulen N.P.E., Hanzlik R.P. J. Org. Chem. 62:1997;8227.
52. Taki M., Itoh S., Fukuzumi S. J. Am. Chem. Soc. 124:2002;998.
53. Sobkowiak A., Naróg D., Sawyer D.T. J. Mol. Catal. A Chem. 159:2000;247.
54. Paczesniak T., Sobkowiak A. J. Mol. Catal. A Chem. 194:2003;1.
55. D.T. Sawyer, A. Sobkowiak, J.L. Roberts, Jr., Electrochemistry for Chemists, second ed., Wiley, New York, 1995, p. 189.
56. Sugimoto H., Sawyer D.T. J Am. Chem. Soc. 107:1985;5712.
57. Sheu C., Richert S.A., Cofré P., Ross B., Sobkowiak A., Sawyer D.T., Kanofsky J.R. J. Am. Chem. Soc. 112:1990;1936.
58. Richert S.A., Tsang P.K.S., Sawyer D.T. Inorg. Chem. 28:1989;2471.
59. Collomb Dunand-Santhier M.-N., Deronzier A., Duboc Toia C., Fontecave M., Gorgy K., Leprête J.-C., Ménage S. J. Electroanal. Chem. 469:1999;53.
60. M. Hudlicky, Oxidations in Organic Chemistry, ACS Monograph 186, American Chemical Society, Washington, DC, 1990, p. 37.
61. Fukuzumi S., Wong C.L., Kochi J.K. J. Am. Chem. Soc. 102:1980;2928.
62. Schlesener C.J., Kochi J.K. J. Org. Chem. 49:1984;3142.
63. Schlesener C.J., Amatore C., Kochi J.K. J. Phys. Chem. 90:1986;3141.
64. Wayner D.D.M., McPhee D.J., Griller D. J. Am. Chem. Soc. 110:1988;132.
65. Fukuzumi S., Tokuda Y., Fujita M. J. Phys. Chem. 96:1992;8413.
66. Fukuzumi S., Tokuda Y., Etano T., Okamoto T., Otera J. J. Am. Chem. Soc. 115:1993;8960.
67. Sawyer D.T., Sobkowiak A., Matsushita T. Acc. Chem. Res. 29:1996;409.
68. F.A. Cotton, G. Wilkinson, Advanced Inorganic Chemistry, Wiley, New York, fifth ed., 1988, p. 717.
69. D.T. Richens, The Chemistry of Aqua Ions, Wiley, New York, 1997, pp. 369-385.
70. D.R. Lide (Ed.), CRC Handbook of Chemistry and Physics, 73rd ed., CRC Press, Boca Raton, FL, 1992, pp. 9-139.
71. Sawyer D.T. Inorg. Chim. Acta. 226:1994;99.
72. Qiu A., Sawyer D.T. J. Porphyrins Phthalocyanines. 1:1997;125.
73. Feig A.L., Becker M., Schindler S., van Eldik R., Lippard S.J. Inorg. Chem. 35:1996;2590.
74. Feig A.L., Masschelein A., Bakac A., Lippard S.J. J. Am. Chem. Soc. 119:1997;334.
75. Simándi L.I., Simándi T.L. J. Mol. Catal. A Chem. 117:1997;299.
76. Kryatov S.V., Rybak-Akimova E.V., MacMurdo V.L., Que L. Jr. Inorg. Chem. 40:2001;2220.
77. S. Nashino, H. Hosomi, S. Ohba, H. Matsushima, T. Tokii, Y. Nishida, J. Chem. Soc., Dalton Trans. (1999) 1509.
78. Chen K., Que L. Jr. Angew. Chem. Int. Ed. 38:1999;2227.
79. Lange S.J., Miyake H., Que L. Jr. J. Am. Chem. Soc. 121:1999;6330.
80. Miyake H., Chen K., Lange S.J., Que L. Jr. Inorg. Chem. 40:2001;3534.
81. Chen K., Que L. J. Am. Chem. Soc. 123:2001;6327.
82. Kim C., Chen K., Kim J., Que L. Jr. J. Am. Chem. Soc. 119:1997;5964.
83. Ho R.Y.N., Roelfes G., Feringa B.L., Que L. Jr. J. Am. Chem. Soc. 121:1999;264.
84. K. Chen, L. Que, J. Chem. Soc., Chem. Commum. (1999) 1375.
85. Roelfes G., Lubben M., Chen K., Ho R.Y.N., Meetsma A., Genseberger S., Hermant R.M., Hage R., Mandal S.K., Young V.G. Jr., Zang Y., Kooijman H., Spek A.L., Que L. Jr., Feringa B.L. Inorg. Chem. 38:1999;1929.
86. Kurtz D.M. Jr. Chem. Rev. 90:1990;585.
87. V.S. Kulikowa, O.N. Gritsenko, A.A. Shteinman, Mendeleev Commun. (1996) 119.
88. Karasevich E.I., Kulikowa V.S., Shilov A.E., Shteinman A.A. Russ. Chem. Rev. 67:1998;335.
89. Murmann R.K., Healy E.A. J. Am. Chem. Soc. 83:1961;2092.
90. Reiff W.M., Baker W.A. Jr., Erickson N.E. J. Am. Chem. Soc. 90:1968;4794.
91. Ehman D.L., Sawyer D.T. Inorg. Chem. 8:1969;900.
92. David P.G., de Mello P.C. Inorg. Chem. 12:1973;2188.
93. Braterman P.S., Song J-I., Peacock R.D. Inorg. Chem. 31:1992;555.