Catalytic oxidations mediated by metal ions and nitroxyl radicals

Journal of Molecular Catalysis A: Chemical

Volumn 251, Issue 1-2, 2006, Pages 200-214

  Sheldon, Roger A ^a   Arends, Isabel W C E ^a  

^a DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

Homogeneous catalysis; Laccase; Nitroxyl radicals; Oxidation; Tempo

Indexed keywords

CATALYSIS; CATALYSTS; ENZYMES; OXIDATION; POSITIVE IONS; TRANSITION METALS;

HOMOGENEOUS CATALYSIS; LACCASE; NITROXYL RADICALS; TEMPO;

NITROGEN COMPOUNDS;

EID: 33646087884     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2006.02.016     Document Type: Article

References (117)

1. Wieland H., and Offenbächer M. Ber. Dtsch. Chem. Ges. 47 (1914) 2111
2. Hoffmann A.K., and Henderson A.T. J. Am. Chem. Soc. 83 (1961) 4671
3. Lebeder O.L., and Kazarnovskii S.N. Zh. Obshch. Khim. 30 (1960) 1631
4. Lebeder O.L., and Kazarnovskii S.N. CA 55 (1961) 1473a
5. Golubev V.A., Kozlov Yu.N., Petrov A.N., and Purmal A.P. In: Zhdanov R.I. (Ed). Bioactive Spin Lables (1992), Springer, Berlin 119-140
6. Rozantsev E.G. In: Ulrich H. (Ed). Free Nitroxyl Radicals, Engl. Transl. (1970), Plenum Press, New York
7. Keana J.F.W. Chem. Rev. 78 (1978) 37
8. E.G. Rozantsev, V.D. Sholle, Synthesis (1971) (190 and 401).
9. Dagonneau M., Kagan E.S., Mikhailov V.I., Rozantsev E.G., and Sholle V.D. Synthesis (1984) 895
10. Aurich H.G. In: Patai S., and Rappoport Z. (Eds). Nitrones, Nitronates and Nitroxidases (1989), Wiley, New York 313
11. Scott G. Science, Medicine and Nutrition (1997), Albion Publishing, Chichester
12. Bobbitt J.M., and Flores C.L. Heterocycles 27 (1988) 509
13. de Nooy A.E.J., Besemer A.C., and van Bekkum H. Synthesis (1996) 1153
14. Amorati R., Lucarini M., Mugnaini M., Pedulli G.F., Minisci F., Recupero F., Fontana F., Astolfi P., and Greci L. J. Org. Chem. 68 (2003) 1747
15. Koshino N., Cai Y., and Espenson J.H. J. Phys. Chem. A 107 (2003) 4262
16. Mahoney L.R., Mendenhall G.D., and Ingold K.U. J. Am. Chem. Soc. 95 (1973) 8610
17. Jenkins T.C., and Perkins M.J. J. Chem. Soc. Perkin Trans. 2 (1983) 717 (and references cited therein)
18. Janzen E.G. Acc. Chem. Res. 2 (1969) 279
19. J. Foricher, C. Fürbringer, K. Pfoertner, Eur. Pat. 198,351 (1986) to Hoffmann La Roche.
20. Ishii Y., and Sakaguchi S. Catal. Surv. Jpn 3 (1999) 27 (and references cited therein)
21. Ishii Y., Sakaguchi S., and Iwahama T. Adv. Synth. Catal. 343 (2001) 393 (and references cited therein)
22. Ishii Y., Iwahama T., Sakaguchi S., Nakayama K., and Nishiyama Y. J. Org. Chem. 61 (1996) 4520
23. Ishii Y., Kato S., Iwahama T., and Sakaguchi S. Tetrahedron Lett. 37 (1996) 4993
24. Yoshino Y., Hayashi Y., Iwahama T., Sakaguchi S., and Ishii Y. J. Org. Chem. 62 (1997) 6810
25. Sheldon R.A., and Kochi J.K. Metal Catalyzed Oxidations of Organic Compounds (1981), Academic Press, New York
26. Shibamoto A., Sakaguchi S., and Ishii Y. Org. Proc. Res. Dev. 4 (2000) 505
27. Minisci F., Recupero F., Cecchetto A., Gambarotti C., Punta C., Faletti R., Paganelli R., and Pedulli G.F. Eur. J. Org. Chem. (2004) 109
28. S.H.A. Dai, C.Y. Lin, F.A. Stuber, US Patent 4,282,383 (1981) to Upjohn Company.
29. Arends I.W.C.E., Sasidharan M., Kühnle A., Duda M., Jost C., and Sheldon R.A. Tetrahedron 58 (2002) 9055
30. Arends I.W.C.E., Sasidharan M., Chatel S., Sheldon R.A., Jost C., Duda M., and Kühnle A. In: Morrell D.G. (Ed). Catalysis of Organic Reactions (2002), Marcel Dekker, New York 143
31. Sheldon R.A. J. Mol. Catal. 7 (1980) 107
32. Sheldon R.A. In: Ugo R. (Ed). Aspects of Homogeneous Catalysis vol. 4 (1981), Reidel, Dordrecht 3
33. Bashkirov A.N., Kamzolkin V.V., Sokova K.M., and Andreyeva T.P. In: Emanuel N.M. (Ed). Oxidation of Hydrocarbons in the Liquid Phase (1965), Pergamon, Oxford 183
34. Wenzel B.B., Donners M.P.J., Alsters P.L., Feiters M.C., and Nolte R.J.M. Tetrahedron 56 (2000) 7797
35. Baucherel X., Arends I.W.C.E., Ellwood S., and Sheldon R.A. Org. Proc. Res. Dev. 7 (2003) 426
36. Baucherel X., Gonsalvi L., Arends I.W.C.E., Ellwood S., and Sheldon R.A. Adv. Synth. Catal. 346 (2004) 286
37. Kochi J.K. J. Am. Chem. Soc. 84 (1962) 1193
38. Walling C., and Padwa A. J. Am. Chem. Soc. 85 (1963) 1593
39. Walling C., and Wagner P.I. J. Am. Chem. Soc. 86 (1964) 3368
40. Iwahama T., Sakaguchi S., Nishiyama Y., and Ishii Y. Tetrahedron Lett. 36 (1995) 6923
41. Avila D.V., Brown C.E., Ingold K.U., and Lusztyk J. J. Am. Chem. Soc. 115 (1993) 466
42. Avila D.V., Ingold K.U., and Lusztyk J. J. Am. Chem. Soc. 117 (1995) 2929
43. Golubev V.A., Rozantsev E.G., and Neiman M.B. Bull. Acad. Sci. USSR, Chem. Ser. 14 (1965) 1898
44. Miyazawa T., Endo T., Shiihashi S., and Okawara M. J. Org. Chem. 50 (1985) 1332
45. Miyazawa T., and Endo T. J. Org. Chem. 50 (1985) 3930
46. Cella J.A., Kelley J.A., and Kenehan E.F. J. Org. Chem. 40 (1975) 1850
47. Rychovsky S.D., and Vaidyanathan R. J. Org. Chem. 64 (1999) 310
48. Bolm C., Magnus A.S., and Hildebrand J.P. Org. Lett. 2 (2000) 1173
49. Kim S.S., and Nehru K. Synletter (2002) 616
50. Anelli L., Biffi C., Montanari F., and Quici S. J. Org. Chem. 52 (1987) 2559
51. see also. Anelli P., Banfi S., Montanari F., and Quici S. J. Org. Chem. 54 (1989) 2970
52. Anelli P.L., Montanari F., and Quici S. Org. Synth. 69 (1990) 212
53. de Nooy A.E.J., Besemer A.C., and van Bekkum H. Tetrahedron 51 (1995) 8023
54. Bolm C., and Fey T. Chem. Commun. (1999) 1795
55. Fey T., Fischer H., Bachmann S., Albert K., and Bolm C. J. Org. Chem. 66 (2001) 8154
56. Brunel D., Lentz P., Sutra P., Deroide B., Fajula F., and Nagy J.B. Stud. Surf. Sci. Catal. 125 (1999) 237
57. Verhoef M.J., Peters J.A., and van Bekkum H. Stud. Surf. Sci. Catal. 125 (1999) 465
58. Brunel D., Fajula F., Nagy J., Deroide B., Verhoef M., Veum L., Peters J., and van Bekkum H. Appl. Catal. A 213 (2001) 73
59. Gilhespy M., Lok M., and Baucherel X. Chem. Commun. (2005) 2871
60. see also. Ferreira P., Hayer W., Phillips E., Rippon D., and Tsang S.C. Green Chem. 6 (2004) 310 for a soluble polyethyleneglycol-attached TEMPO
61. Ciriminna R., Blum J., Avnis D., and Pagliaro M. Chem. Commun. (2000) 1441
62. Ciriminna R., Bolm C., Fey T., and Pagliaro M. Adv. Synth. Catal. 344 (2002) 159
63. In Ref. 10, p. 175.
64. Dijksman A., Arends I.W.C.E., and Sheldon R.A. Chem. Commun. (2000) 271
65. Dijksman A., Arends I.W.C.E., and Sheldon R.A. Synletter (2001) 102
66. Dijksman A., Arends I.W.C.E., and Sheldon R.A. In: Sherrington D.C., and Kybett A.P. (Eds). Supported Catalysts and Their Applications (2001), Royal Society of Chemistry, U.K. 118-124
67. Brackman W., and Gaasbeek C.J. Rec. Trav. Chim. Pays-Bas 85 (1966) 257
68. Semmelhack M.F., Schmid C.R., Cortes D.A., and Chou S. J. Am. Chem. Soc. 106 (1984) 3374
69. A. Dijksman, Catalytic Oxidation of Alcohols, PhD thesis, Delft, The Netherlands, 2001.
70. Dijksman A., Arends I.W.C.E., and Sheldon R.A. Chem. Commun. (1999) 1591
71. see also. Inokuchi T., Nakagawa K., and Torii S. Tetrahedron Lett. 36 (1995) 3223 for a related system using stoichiometric amounts of 4-benzoyloxy TEMPO
72. Dijksman A., Marino-Gonzalez A., Mairata i Payeras A., Arends I.W.C.E., and Sheldon R.A. J. Am. Chem. Soc. 123 (2001) 6826
73. Dijksman A., Arends I.W.C.E., and Sheldon R.A. Plat. Metals Rev. 45 (2001) 15
74. Sheldon R.A., Arends I.W.C.E., ten Brink G.J., and Dijksman A. Acc. Chem. Res. 35 (2002) 774
75. Bäckvall J.E., and Andreasson U. Tetrahedron Lett. 34 (1993) 5459
76. Trost B.M., and Kulawiec R.J. Tetrahedron Lett. 27 (1986) 1119
77. Paleos C.M., and Dais P. J. Chem. Soc. Chem. Commun. (1977) 345
78. Semmelhack M.F., Schmid C.R., and Cortes D.A. Tetrahedron Lett. 27 (1986) 119
79. Dijksman A., Arends I.W.C.E., and Sheldon R.A. Org. Biomol. Chem. 1 (2003) 3232
80. Mahanthappa M.K., Huang K.W., Cole A.P., and Waymouth R.M. Chem. Commun. (2002) 502
81. Forbes G.C., Kennedy A.R., Mulvey R.E., and Rodger P.J.A. Chem. Commun. (2001) 1400
82. Evans W.J., Perotti J.M., Doedens R.J., and Ziller J.W. Chem. Commun. (2001) 2326
83. Wang Y., DuBois J.L., Hedman B., Hodgson K.O., and Stack T.D.P. Science 279 (1998) 537
84. Laugier J., Latour J.M., Caneschi A., and Rey P. Inorg. Chem. 30 (1991) 4474
85. Caneschi A., Grand J., Laugier J., Rey P., and Subra R. J. Am. Chem. Soc. 110 (1988) 2307
86. Firbank S.J., Rogers M.S., Wilmot C.M., Dooley D.M., Halcrow M.A., Knowles P.F., McPherson M.J., and Phillips S.E.V. Proc. Natl. Acad. Sci. U.S.A. 98 (2001) 12932
87. Whittaker M.M., and Whittaker J.M. Biochemistry 40 (2001) 7140
88. Gamez P., Arends I.W.C.E., Reedijk J., and Sheldon R.A. Chem. Commun. (2003) 2414
89. Ansari I.A., and Gree R. Org. Lett. 4 (2002) 1507
90. Betzemeier B., Cavazzini M., Quici S., and Knochel P. Tetrahedron Lett. 41 (2000) 4343
91. Ragagnin G., Betzemeier B., Quici S., and Knochel P. Tetrahedron (2002) 3985
92. see also. Holczknecht O., Cavazzini M., Quici S., Shepperson I., and Pozzi G. Adv. Synth. Catal. 347 (2005) 677 for the use of 'fluorous tagged' TEMPO radicals as catalysts in the bleach oxidation of alcohols
93. Liu R., Liang X., Dong C., and Hu X. J. Am. Chem. Soc. 126 (2004) 4112
94. ten Have R., and Teunissen P.J.M. Chem. Rev. 101 (2001) 3397
95. In: Messerschmidt A. (Ed). Multi-Copper Oxidases (1997), World Scientific, Singapore
96. Bourbonnais R., and Paice M.G. FEBS Lett. 267 (1990) 99
97. for a review see:. Rochefort D., Leech D., and Bourbonnais R. Green Chem. 6 (2004) 14
98. Eggert C.B., Temp U., and Eriksson K.E. FEBS Lett. 391 (1996) 144
99. Srebotnik E., and Hammel K.E. J. Biotechnol. 81 (2000) 179
100. Sealey J., and Ragauskas A.J. J. Wood Chem. Technol. 18 (1998) 403
101. Xu F., Kulys J.J., Duke K., Li K., Krikstopaitis K., Deussen H.J.W., Abbate E., Galinyte V., and Schneider P. Appl. Environ. Microbiol. 66 (2000) 2052
102. Potthast A., Rosenau T., Chen C.L., and Gratzl J.S. J. Mol. Catal. A: Chem. 108 (1996) 5
103. Fabbrini M., Galli C., Gentili P., and Macchitella D. Tetrahedron Lett. 42 (2001) 7551
104. L. Viikari, M.L. Niku-Paavola, J. Buchert, P. Forssell, A. Teleman, K. Kruus, WO 992,324,0, 1999.
105. J.M. Jetten, R.T.M. van den Dool, W. van Hartingsveldt, M.T.R. van Wandelen, WO 00/50621, 2000.
106. Fabbrini M., Galli C., and Gentili P. J. Mol. Catal. B: Enzymatic 16 (2002) 231
107. Baiocco P., Barreca A.M., Fabbrini M., Galli C., and Gentili P. Org. Biomol. Chem. 1 (2003) 191
108. d'Acunzo F., Baiocco P., Fabbrini M., Galli C., and Gentili P. Eur. J. Org. Chem. (2002) 4195
109. Bertrand T., Jolivalt C., Briozzo P., Caminade E., Joly N., Madzak C., and Mougin C. Biochemistry 23 (2002) 7325
110. B. Reinhammer, in Ref. 107, Chapter 6.
111. Frausto da Silva J.J.R., and Williams R.J.P. The Biological Chemistry of the Elements (1991), Clarendon Press, Oxford p. 182
112. I.W.C.E. Arends, R.A. Sheldon, Tetrahedron, 2006, in press.
113. Xu F., Deussen H.J.W., Lopez B., Lam L., and Li K. Eur. J. Biochem. 268 (2001) 4169
114. For a review of TEMPO mediated carbohydrate oxidations see. Bragd P.L., van Bekkum H., and Besemer A.C. Topics Catal. 27 (2004) 49
115. see also. Bragd P.L., Besemer A.C., and van Bekkum H. J. Mol. Catal. A: Chem. 170 (2001) 35
116. For a recent review see:. Sheldon R.A., Schoevaart R., and van Langen L.M. Biocat. Biotrans. 23 3/4 (2005) 141
117. Goldstein S., Merenyi G., Russo A., and Samuni A. J. Am. Chem. Soc. 125 (2003) 789