Oxidation chemistry of poly(ethylene glycol)-supported carbonylruthenium(ii) and dioxoruthenium(vi) meso-tetrakis(pentafluorophenyl) porphyrin

Chemistry - A European Journal

Volumn 12, Issue 11, 2006, Pages 3020-3031

  Zhang, Jun Long ^a   Huang, Jie Sheng ^a   Che, Chi Ming ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

Homogeneous catalysis; Oxidation; Porphyrinoids; Ruthenium; Supported catalysts

Indexed keywords

BENZENE; ESTERS; LIGHT SCATTERING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PORPHYRINS; REACTION KINETICS;

HOMOGENEOUS CATALYSIS; INTRAMOLECULAR AMIDATION; PORPHYRINOIDS; SUPPORTED CATALYSTS;

POLYETHYLENE GLYCOLS;

MACROGOL DERIVATIVE; METALLOPORPHYRIN; RUTHENIUM;

ARTICLE; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

METALLOPORPHYRINS; OXIDATION-REDUCTION; POLYETHYLENE GLYCOLS; RUTHENIUM;

EID: 33645714883     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200501510     Document Type: Article

References (99)

1. For reviews, see: a) B. Meunier, Chem. Rev. 1992, 92, 1411;
2. b) J. P. Collman, X. Zhang, V. J. Lee, E. S. Uffelman, J. I. Brauman, Science 1993, 261, 1404;
3. c) D. Dolphin, T. G. Traylor, L. Y. Xie, Acc. Chem. Res. 1997, 30, 251;
4. d) J. L. McLain, J. Lee, J. T. Groves, in Biomimetic Oxidations Catalyzed by Transition Metal Complexes (Ed.: B. Meunier), Imperial College Press, London, 2000, p. 91;
5. e) P. Müller, C. Fruit, Chem. Rev. 2003, 103, 2905;
6. f) P. Dauban, R. H. Dodd, Synlett 2003, 1571;
7. g) P. Tagliatesta, B. Floris, P. Galloni, J. Porphyrins Phthalocyanines 2003, 7, 351;
8. h) G. Simonneaux, P. Tagliatesta, J. Porphyrins Phthalocyanines 2004, 8, 1166;
9. i) G. Maas, Chem. Soc. Rev. 2004, 33, 183;
10. j) Q.-H. Xia, H.-Q. Ge, C.-P. Ye, Z.-M. Liu, K.-X. Su, Chem. Rev. 2005, 105, 1603.
11. For examples of insoluble polymer-supported metalloporphyrin catalysts, see: a) X.-Q. Yu, J.-S. Huang, W.-Y. Yu, C.-M. Che, J. Am. Chem. Soc. 2000, 122, 5337;
12. b) O. Nestler, K. Severin, Org. Lett. 2001, 3, 3907;
13. c) E. Brulé, Y. R. de Miguel, Tetrahedron Lett. 2002, 43, 8555;
14. d) S. Tangestaninejad, M. H. Habibi, V. Mirkhani, M. Moghadam, Molecules 2002, 7, 264;
15. e) B. G. Choi, R. Song, W. Nam, B. Jeong, Chem. Commun. 2005, 2960;
16. f) E. Burri, M. Ohm, C. Daguenet, K. Severin, Chem. Eur. J. 2005, 11, 5055.
17. For examples of silica material-supported metalloporphyrin catalysts, see: a) B.-Z. Zhan, X.-Y. Li, Chem. Commun. 1998, 349;
18. b) B. T. Holland, C. Walkup, A. Stein, J. Phys. Chem. B 1998, 102, 4301;
19. c) C.-J. Liu, W.-Y. Yu, S.-G. Li, C.-M. Che. J. Org. Chem. 1998, 63, 7364;
20. d) V. Schünemann, A. X. Trautwein, I. M. C. M. Rietjens, M. G. Boersma, C. Veeger, D. Mandon, R. Weiss, K. Bahl, C. Colapictro, M. Piech, R. N. Austin. Inorg. Chem. 1999, 38, 4901;
21. e) S. Evans, J. R. Lindsay Smith. J. Chem. Soc. Perkin Trans. 2 2001, 174;
22. f) J.-L. Zhang, Y.-L. Liu, C.-M. Che, Chem. Commun. 2002, 2906;
23. g) D. E. De Vos, M. Dams, B. F. Sels, P. A. Jacobs. Chem. Rev. 2002, 102, 3615 and the references therein.
24. For examples of soluble polymer-supported or dendritic metallopor-phyrin catalysts, see: a) P. Bhyrappa, J. K. Young, J. S. Moore, K. S. Suslick, J. Am. Chem. Soc. 1996, 118, 5708;
25. b) M. Kimura, T. Shiba, M. Yamazaki, K. Hanabusa, H. Shirai, N. Kobayashi, J. Am. Chem. Soc. 2001, 123, 5636;
26. c) J.-L. Zhang, H.-B. Zhou, J.-S. Huang, C.-M. Che, Chem. Eur. J. 2002, 8, 1554;
27. d) J.-L. Zhang, C.-M. Che, Org. Lett. 2002, 4, 1911;
28. e) C.-Y. Zhou. W.-Y. Yu, C.-M. Che, Org. Lett. 2002, 4, 3235;
29. f) M. Benaglia, T. Danelli, G. Pozzi, Org. Biomol. Chem. 2003, 1, 454;
30. g) C.-M. Che, J.-S. Huang, J.-L. Zhang, C. R. Chim. 2003, 6, 1105.
31. For reviews, see: a) D. Mansuy, Coord. Chem. Rev. 1993, 125, 129;
32. b) Y. Murakami, J.-i. Kikuchi, Y. Hisaeda, O. Hayashida, Chem. Rev. 1996, 96, 721;
33. c) E. Rose, A. Lecas, M. Quelquejeu, A. Kossanyi, B. Boitrel. Coord. Chem. Rev. 1998, 178-180. 1407.
34. a) R. Breslow, Y. Huang, X. J. Zhang, J. Yang, Proc. Natl. Acad. Sci. USA 1997, 94, 11 156;
35. b) J. Yang, R. Breslow, Angew. Chem. 2000, 112, 2804;
36. Angew. Chem. Int. Ed. 2000, 39, 2692:
37. c) S. Belvedere, R. Breslow, Bioorg. Chem. 2001. 29. 321;
38. d) J. Yang, B. Gabriele, S. Belvedere, Y. Huang, R. Breslow, J. Org. Chem. 2002, 67, 5057;
39. e) R. Breslow, Z. L. Fang, Tetrahedron Lett. 2002, 43, 5197.
40. a) J. T. Groves, R. Neumann, J. Am. Chem. Soc. 1987, 109, 5045;
41. b) J. T. Groves, R. Neumann, J. Am. Chem. Soc. 1989. 111. 2900.
42. R. R. French, P. Holzer, M. G. Leuenberger, W.-D. Woggon, Angew. Chem. 2000, 112, 1321;
43. Angew. Chem. Int. Ed. 2000, 39, 1267.
44. P. Thordarson, E. J. A. Bijsterveld, A. E. Rowan, R. J. M. Nolle, Nature 2003, 424, 915.
45. a) T. Sagawa, H. Ishida, K. Urabe, K. Yoshinaga, K. Ohkubo, J. Chem. Soc. Perkin Trans. 2 1993, 1;
46. b) T. Sagawa, H. Ishida, K. Urabe, K. Yoshinaga, K. Ohkubo, J. Mol. Catal. 1993, 81, L13.
47. M. Nango, T. Iwasaki, Y. Takeuchi, Y. Kurono, J. Tokuda, R. Oura, Langmuir 1998, 14, 3272.
48. Selected examples or reviews: a) C. K. Chang, M.-S. Kuo, J. Am. Chem. Soc. 1979, 101, 3413;
49. b) D.-H. Chin, A. L. Balch, G. N. La Mar, J. Am. Chem. Soc. 1980, 102, 1446;
50. c) J. T. Groves, R. C. Haushalter, M. Nakamura, T. E. Nemo, B. J. Evans, J. Am. Chem. Soc. 1981, 103, 2884;
51. d) A. L. Balch, Y.-W. Chan, R.-J. Cheng, G. N. La Mar, L. Latos-Grazynski, M. W. Renner, J. Am. Chem. Soc. 1984, 106, 7779;
52. e) J. T. Groves, M. K. Stern, J. Am. Chem. Soc. 1988, 110, 8628;
53. f) J. M. Garrison, D. Ostović, T. C. Bruice, J. Am. Chem. Soc. 1989, 111, 4960;
54. g) K. Yamaguchi, Y. Watanabe, I. Morishima, J. Chem. Soc. Chem. Commun. 1992, 1721;
55. h) D. Ostovic, G.-X. He, T. C. Bruice, in Metalloporphyrins in Catalytic Oxidations (Ed.: R. A. Sheldon). Marcel Dekker. New York, 1994, Chapter 2, p. 29;
56. i) J. T. Groves, J. Lee, S. S. Maria, J. Am. Chem. Soc. 1997, 119, 6269;
57. j) M. Schappacher, J. L. Putaux, C. Lefebvre, A. Deffieux, J. Am. Chem. Soc. 2005, 127, 2990.
58. a) J. T. Groves, R. Quinn, Inorg. Chem. 1984, 23, 3844;
59. b) W.-H. Leung, C.-M. Che, J. Am. Chem. Soc. 1989, 111, 8812;
60. c) P. Le Maux, H. Bahri, G. Simonneaux, J. Chem. Soc. Chem. Commun. 1994, 1287;
61. d) C-J. Liu, W.-Y. Yu, S.-M. Peng, T. C. W. Mak, C.-M. Che, J. Chem. Soc. Dalton Trans. 1998, 1805;
62. e) C.-J. Liu, W.-Y. Yu, C.-M. Che, C.-H. Yeung, J. Org. Chem. 1999, 64, 7365;
63. f) R. Zhang, W.-Y. Yu, H.-Z. Sun, W.-S. Liu, C.-M. Che, Chem. Eur. J. 2002, 8, 2495.
64. J. T. Groves, M. Bonchio, T. Carofiglio, K. Shalyaev, J. Am. Chem. Soc. 1996, 118, 8961.
65. P. Battioni, O. Brigaud, H. Desvaux, D. Mansuy, T. G. Traylor, Tetrahedron Lett. 1991, 32, 2893.
66. a) J. Kriz, B. Masar, H. Pospisil, J. Plestil, Z. Tuzar, M. A. Kiselev, Macromolecules 1996, 29, 7853;
67. b) M. Mizusaki, Y. Morishima, F. M. Winnik, Macromolecules 1999, 32, 4317.
68. J. Leclaire, Y. Coppel, A.-M. Caminade, J.-P. Majoral, J. Am. Chem. Soc. 2004, 126, 2304.
69. R. C. Larock, Comprehensive Organic Transformations: A Guide to Functional Group Preparations. VCH, New York, 1989, p. 505.
70. R. L. Halcomb, S. J. Danishefsky, J. Am. Chem. Soc. 1989, 111, 6661.
71. Selected examples: a) S.-M. Au, J.-S. Huang, W.-Y. Yu, W.-H. Fung, C.-M. Che, J. Am. Chem. Soc. 1999, 121, 9120;
72. b) X.-Q. Yu, J.-S. Huang, X.-G. Zhou, C.-M. Che, Org. Lett. 2000, 2, 2233;
73. c) X.-G. Zhou, X.-Q. Yu, J.-S. Huang, C.-M. Che, Chem. Commun. 1999, 2377;
74. d)J.-L. Liang, J.-S. Huang, X.-Q. Yu, N. Zhu, C.-M. Che, Chem. Eur. J. 2002, 8. 1563:
75. e) J.-L. Liang, S.-X. Yuan, J.-S. Huang, W.-Y. Yu, C.-M. Che, Angew. Chem. 2002, 114, 3615;
76. Angew. Chem. Int. Ed. 2002, 41, 3465.
77. Selected examples: a) R. Breslow, S. H. Gellman, J. Chem. Soc. Chem. Commun. 1982, 1400;
78. b) R. Breslow, S. H. Gellman, J. Am. Chem. Soc. 1983, 105, 6728;
79. c) J. P. Mahy, G. Bedi, P. Battioni, D. Mansuy, Tetrahedron Lett. 1988, 29, 1927;
80. d) J. Yang, R. Weinberg, R. Breslow, Chem. Commun. 2000, 531.
81. a) C. G. Espino, P. M. Wehn, J. Chow, J. Du Bois, J. Am. Chem. Soc. 2001, 123, 6935;
82. b) P. M. Wehn, J. Du Bois, J. Am. Chem. Soc. 2002, 724, 12950;
83. c) P. M. Wehn, J. Lee, J. Du Bois, Org. Lett. 2003, 5, 4823;
84. d) A. Hinman, J. Du Bois, J. Am. Chem. Soc. 2003, 125, 11510.
85. a) J. M. Harris, Poly(ethylene glycol) Chemistry: Biotechnical and Biomedical Applications. Plenum, New York, 1992;
86. b) Metal Complexes and Metals in Macromolecules: Synthesis, Structure and Properties, (Eds.: D. Wöhrle, A. D. Pomogailo), Wiley-VCH, Weinheim, 2003;
87. c) Polymeric Materials in Organic Synthesis and Catalysis (Ed.: M. R. Buchmeiser), Wiley-VCH, Weinheim, 2003.
88. a) R. Breslow, Acc. Chem. Res. 1991, 24, 159;
89. b) X.-K. Jiang, Y.-Z. Hui, Z.-X. Fei, J. Am. Chem. Soc. 1987, 109, 5862;
90. c) W.-Q. Fan, X.-K. Jiang, J. Am. Chem. Soc. 1985, 107, 7680.
91. a) K. Persson, G. Wang, G. Olofsson, J. Chem. Soc. Faraday Trans. 1994, 90, 3555;
92. b) H. Zhang, J. Pan, T. E. Hogen-Esch, Macromolecules 1998, 31, 2815;
93. c) M. Valentini, A. Vaccaro, A. Rehor, A. Napoli, J. A. Hubbell, N. Tirelli, J. Am. Chem. Soc. 2004, 126, 2142.
94. a) C.-M. Che, J.-L. Zhang, L.-R. Lin, Chem. Commun. 2002, 2556;
95. b) N. J. Turro, PL. Kuo, Langmuir 1986, 2, 438;
96. c) A. Pendri, A. Martinez, J. Xia, R. G. L. Shorr, R. B. Greenwald, Bioconjugate Chem. 1995, 6, 596.
97. R. J. Rousseau, R. K. Robins, J. Heterocycl. Chem. 1965, 2, 196.
98. Y. Yamada, T. Yamamoto, M. Okawara, Chem. Lett. 1975, 361.
99. C.-M. Che, J.-L. Zhang, R. Zhang, J.-S. Huang, T.-S. Lai, W.-M. Tsui, X.-G. Zhou, Z.-Y. Zhou, N. Zhu, C. K. Chang, Client. Eur. J. 2005, 11, 7040.