Hydrocarbon oxidation by β-halogenated dioxoruthenium(vi) porphyrin complexes: Effect of reduction potential (RuVI/V) and C-H bond-dissociation energy on rate constants

Chemistry - A European Journal

Volumn 11, Issue 23, 2005, Pages 7040-7053

  Che, Chi Ming ^a   Zhang, Jun Long ^a   Zhang, Rui ^a   Huang, Jie Sheng ^a   Lai, Tat Shing ^b   Tsui, Wai Man ^a   Zhou, Xiang Ge ^a   Zhou, Zhong Yuan ^c   Zhu, Nianyong ^a   Chang, Chi Kwong ^b  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

^c HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

Electrochemistry; Oxidation; Porphyrinoids; Ruthenium; Structure elucidation

Indexed keywords

AXIAL LIGANDS; HYDROCARBON OXIDATION; STRUCTURE ELUCIDATION;

HYDROCARBONS; OXIDATION; REACTION KINETICS; RUTHENIUM COMPOUNDS;

ORGANOMETALLICS;

PORPHYRIN; RUTHENIUM DERIVATIVE;

CHEMICAL STRUCTURE; CHEMISTRY; CONFERENCE PAPER; HYDROGEN BOND; INFRARED SPECTROPHOTOMETRY; KINETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; THERMODYNAMICS; ULTRAVIOLET SPECTROPHOTOMETRY; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; OXIDATION-REDUCTION; PORPHYRINS; RUTHENIUM COMPOUNDS; SPECTROPHOTOMETRY, INFRARED; SPECTROPHOTOMETRY, ULTRAVIOLET; THERMODYNAMICS;

EID: 27944472608     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200500814     Document Type: Conference Paper

References (102)

1. 3tpp = 5,10,15,20-tetrakis(2,4,6-trime-thoxyphenyl)porphyrinato(2-).
2. J. T. Groves, T. E. Nemo, R. S. Myers, J. Am. Chem. Soc. 1979, 101, 1032.
3. a) B. Meunier, Chem. Rev. 1992, 92, 1411;
4. b) J. P. Collman, X. Zhang, V. J. Lee, E. S. Uffelman, J. I. Brauman, Science 1993, 261, 1404;
5. c) D. Mansuy, Coord. Chem. Rev. 1993, 125, 129.
6. D. Dolphin, T. G. Traylor, L. Y. Xie, Acc. Chem. Res. 1997, 30, 251.
7. C. K. Chang, F. Ebina, J. Chem. Soc. Chem. Commun. 1981, 778.
8. P. S. Traylor, D. Dolphin, T. G. Traylor. J. Chem. Soc. Chem. Commun. 1984, 279.
9. T. G. Traylor, S. Tsuchiya, Inorg. Chem. 1987, 26, 1338.
10. a) P.E. Ellis, Jr., J. E. Lyons, Catal. Lett. 1989, 3, 389;
11. b) P. E. Ellis, Jr., J. E. Lyons, Coord. Chem. Rev. 1990, 105, 181.
12. P. Hoffmann, G. Labat, A. Robert, B. Meunier, Tetrahedron Lett. 1990, 31, 1991.
13. J. F. Bartoli, O. Brigaud, P. Battioni, D. Mansuy, J. Chem. Soc. Chem. Commun. 1991, 440.
14. M. W. Grinstaff, M. G. Hill, J. A. Labinger, H. B. Gray, Science 1994, 264, 1311.
15. a) E. Porhiel, A. Bondon, J. Leroy, Tetrahedron Lett. 1998, 39, 4829;
16. b) E. Porhiel, A. Bondon, J. Leroy, Eur. J. Inorg. Chem. 2000, 1097.
17. F. Hino, D. Dolphin, Chem. Commun. 1999, 629.
18. E. Baciocchi, T. Boschi, L. Cassioli, C. Galli, L. Jaquinod, A. Lapi, R. Paolesse, K. M. Smith, P. Tagliatesta, Eur. J. Org. Chem. 1999, 3281.
19. F. G. Doro, J. R. L. Smith, A. G. Ferreira, M. D. Assis, J. Mol. Catal. A 2000, 164, 97.
20. 2tpp)Cl], respectively, as catalysts for PhIO hydrox ylation of ethylbenzene or cyclohexane (see: Z. Gross, L. Simkhovich, Tetrahedron Lett. 1998, 39, 8171).
21. T. Wijesekera, A. Matsumoto, D. Dolphin, D. Lexa, Angew. Chem. 1990, 102, 1073;
22. Angew. Chem. Int. Ed. Engl. 1990, 29, 1028.
23. P. Bhyrappa, V. Krishnan, Inorg. Chem. 1991, 30, 239.
24. E. R. Birnbaum, W. P. Schaefer, J. A. Labinger, J. E. Bercaw, H. B. Gray, Inorg. Chem. 1995, 34, 1751.
25. E. K. Woller, S. G. DiMagno, J. Org. Chem. 1997, 62, 1588.
26. In the case of β-chlorination or -bromination, a severe distortion of the porphyrin ligand could occur (see, for example, refs. [4] and [11]). Such porphyrin distortion is known to destabilize the HOMO of the porphyrin macrocycle, making the porphyrin ligand easier to oxidize (opposite to the inductive effect of the electron-withdrawing β-halogen substituents); however, the reduction of porphyrin ligands is little affected by the porphyrin distortion. See: a) M. O. Senge, in Porphyrin Handbook, Vol.1 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego, 2000, Chapter 6, p. 239;
27. b) K. M. Kadish, E. van Camelbecke, G. Royal, in Porphyrin Handbook, Vol.8 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego, 2000, Chapter 55, p. 1.
28. a) P. G. Gassman, A. Ghosh, J. Almlöf, J. Am. Chem. Soc. 1992, 114. 9990;
29. b) A. Ghosh, J. Am. Chem. Soc. 1995, 117, 4691;
30. c) A. Ghosh, Acc. Chem. Res. 1998, 31, 189.
31. H.L. Chen, P.E. Ellis, Jr., T. Wijesekera, T. E. Hagan, S. E. Groh, J. E. Lyons, D. P. Ridge, J. Am. Chem. Soc. 1994, 116, 1086.
32. a) J.T. Groves, W. J. Kruper Jr., J. Am. Chem. Soc. 1979, 101, 7613;
33. b) S. E. Creager, R. W. Murray, Inorg. Chem. 1985, 24, 3824;
34. c) J. M. Garrison, T. C. Bruice, J. Am. Chem. Soc. 1989, 111, 191;
35. d) J. M. Garrison, D. Ostovic, T. C. Bruice, J. Am. Chem. Soc. 1989, 111, 4960.
36. a) J. T. Groves, R. C. Haushalter, M. Nakamura, T. E. Nemo, B. J. Evans, J. Am. Chem. Soc. 1981, 103, 2884;
37. b) S. Tsuchiya, J. Chem. Soc. Chem. Commun. 1991, 716;
38. c) K. Yamaguchi, Y. Watanabe, I. Morishima, J. Chem. Soc. Chem. Commun. 1992, 1721;
39. d) H. Fujii, J. Am. Chem. Soc. 1993, 115, 4641;
40. e) Z. Gross, S. Nimri, J. Am. Chem. Soc. 1995, 117, 8021;
41. f) Y. M. Goh, W. Nam, Inorg. Chem. 1999, 38, 914.
42. a) J. T. Groves, W. J. Kruper, Jr., R. C. Haushalter, J. Am. Chem. Soc. 1980, 102, 6375;
43. b) M. Schappacher, R. Weiss, Inorg. Chem. 1987, 26, 1189;
44. c) J. T. Groves, M. K. Stern, J. Am. Chem. Soc. 1987, 109, 3812;
45. d) J. T. Groves, M. K. Stern, J. Am. Chem. Soc. 1988, 110, 8628;
46. e) R. D. Arasasingham, G.-X. He, T. C. Bruice, J. Am. Chem. Soc. 1993, 115, 7985.
47. a) J. T. Groves, R. Quinn, J. Am. Chem. Soc. 1985, 107, 5790;
48. b) W.-H. Leung, C.-M. Che, J. Am. Chem. Soc. 1989, 111, 8812;
49. c) C. Ho. W.-H. Leung, C.-M. Che, J. Chem. Soc. Dalton Trans. 1991, 2933;
50. d) T.-S. Lai, R. Zhang, K.-K. Cheung, H.-L. Kwong, C.-M. Che, Chem. Commun. 1998, 1583;
51. e) C.-J. Liu, W.-Y. Yu, S.-M. Peng, T. C.W. Mak, C.-M. Che, J. Chem. Soc. Dalton Trans. 1998, 1805;
52. f) C.-J. Liu, W.-Y. Yu, C.-M. Che, C.-H. Yeung, J. Org. Chem. 1999, 64, 7365.
53. 2 at -80°C, but the reactivity of this oxoiron species toward hydrocarbon oxidations is not reported (see: P. Ochsenbein, D. Mandon, J. Fischer, R. Weiss, R. Austin, K. Jayaraj, A. Gold, J. Terner, E. Bill, M. Müther, A. X. Trautwein, Angew. Chem. 1993, 105, 1504;
54. Angew. Chem. Int. Ed. Engl. 1993, 32, 1437).
55. J. R. Bryant, J. M. Mayer, J. Am. Chem. Soc. 2003, 125, 10351.
56. a) M. Tsutsui, D. Ostfeld, L. M. Hoffman, J. Am. Chem. Soc. 1971, 93, 1820;
57. b) J. J. Bonnet, S. S. Eaton, G. R. Eaton, R. H. Holm, J. A. Ibers, J. Am. Chem. Soc. 1973, 95, 2141;
58. c) G. M. Brown, F. R. Hopf, J. A. Ferguson, T. J. Meyer, D. G. Whitten, J. Am. Chem. Soc. 1973, 95, 5939;
59. d) R. G. Little, J. A. Ibers, J. Am. Chem. Soc. 1973, 95, 8583;
60. e) D. P. Rillema, J. K. Nagle, L. F. Barringer, Jr., T. J. Meyer, J. Am. Chem. Soc. 1981, 103, 56;
61. f) J. P. Collman, C.E. Barnes, P.N. Swepston, J. A. Ibers, J. Am. Chem. Soc. 1984, 106, 3500.
62. a) S.-I. Murahashi, T. Naota, N. Komiya, Tetrahedron Lett. 1995, 36, 8059;
63. b) J. T. Groves, M. Bonchio, T. Carofiglio, K. Shalyaew, J. Am. Chem. Soc. 1996, 118, 8961.
64. a) S. S. Eaton, G. R. Eaton. J. Am. Chem. Soc. 1975, 97, 3660;
65. h) J. T. Groves, R. Quinn, Inorg. Chem. 1984, 23, 3844.
66. a) W.-C. Lo, C.-M. Che, K.-F. Cheng, T. C. W. Mak, Chem. Commun. 1997, 1205;
67. b) A. Berkessel, M. Frauenkron, J. Chem. Soc. Perkin Trans. 1 1997, 2265;
68. c) T.-S. Lai, H.-L. Kwong, R. Zhang, C.-M. Che, J. Chem. Soc. Dalton Trans. 1998, 3559.
69. E. R. Birnbaum, W. P. Schaefer, J. A. Labinger, J. E. Bercaw, H. B. Gray, Inorg. Chem. 1995, 34, 1751.
70. -1, see: a) references [30-34];^p^pb) J. P. Collman, C. E. Barnes, P. J. Brothers. T. J. Collins, T. Ozawa, J. C. Gallucci, J. A. Ibers, J. Am. Chem. Sac. 1984, 106, 5151;
71. c) C. Slebodnick, K. Kim, J. A. Ibers, Inorg. Chem. 1993, 32, 5338;
72. d) B. Scharbert, E. Zeisberger, E. Paulus, J. Organomet. Chem. 1995, 493, 143;
73. e) C. Slebodnick, W. K. Seok, K. M. Kim, J. A. Ibers, Inorg. Chim. Acta 1996, 243, 57;
74. f) R. Salzmann, C. J. Ziegler, N. Godbout, M. T. McMahon, K. S. Suslick, E. Oldfield.y. Am. Chem. Soc. 1998, 120, 11 323.
75. 28-tpp ligand are sparse, see, for example: a) V. V. Smirnov, E. K. Woller, S. G. Di-Magno, Inorg. Chem. 1998, 37, 4971;
76. b) A. P. Nelson, S. G. DiMagno, J. Am. Chem. Soc. 2000, 122, 8569;
77. c) H. Sun, V. V. Smirnov, S. G. DiMagno, Inorg. Chem. 2003, 42, 6032;
78. d) S.-W. Lai, Y.-J. Hou, C.-M. Che, H.-L. Pang, K.-Y. Wong. C. K. Chang, N. Zhu, Inorg. Chem. 2004, 43, 3724.
79. 2O·MeOH is surprising, since previously reported structurally characterized carbonylruthenium(II) porphyrin complexes crystallized from alcohol-containing solvents exclusively bind an alcohol molecule at an axial site (see refs [30b] and [33a]).
80. a) J. T. Groves, Y. Han. D. V. Engen. J. Chem. Soc. Chem. Commun. 1990, 436;
81. b) P. Le Maux, H. Bahri, G. Simonneaux, L. Toupet, Inorg. Chem. 1995, 34, 4691;
82. c) P. G. Jene, J. A. Ibers, J. Porphyrins Phthalocyanines 2001, 5, 419.
83. II(tpp)(CO)(1-MeIm)] (1-MeIm = 1-methylimidazole) was reported to have a short C-O bond of 1.061(3) Å (ref. [35f]), coupled with a normal Fe-C(CO) bond of 1.793(3) Å.
84. K. M. Kadish, Y. Hu, X. H. Mu, J. Heterocycl. Chem. 1991, 28, 1821.
85. 2O·) distances of 3.07 Å (see ref. [40]).
86. T. C. W. Mak, C.-M. Che, K.-Y. Wong, J. Chem. Soc. Chem. Commun. 1985, 986.
87. a) R. G. Ball, G. Domazetis, D. Dolphin, B. R. James, J. Trotter, Inorg. Chem. 1981, 20, 1556;
88. b) S. Ariel, D. Dolphin, G. Domazetis, B. R. James, T. W. Leung, S. J. Rettig, J. Trotter, G. M. Williams, Can. J. Chem. 1984, 62, 755;
89. c) E. Stulz, M. Maue, N. Feeder, S. J. Teat, Y.-F. Ng, A. D. Bond, S. L. Darling, J. K. M. Sanders, Inorg. Chem. 2002, 41, 5255.
90. For example, the reactions of 2b,c with styrene exhibited isosbestic points at 405, 430 nm for 2b and 396, 480 nm for 2c. In the absence of pyrazole, no isosbestic points were observed.
91. We found that the rate constants obtained are not dependent on the concentration of pyrazole present in the reaction mixtures. For example, varying the concentration of pyrazole within the range of 1-10% w/w did not cause appreciable change in the rate constants. In the absence of hydrocarbon substrates, the dioxo complexes 2 a-f exhibit no appreciable reaction with pyrazole under the same conditions on the time scale of the kinetic studies.
92. J.-L. Zhang, C.-M. Che, Chem. Eur. J. 2005, 11, 3899.
93. J. Leroy, A. Bondon, L. Toupet, Acta Crystallogr. Sect. C 1999, 55, 464.
94. a) J. Leroy, A. Bondon, L. Toupet, C. Rolando, Chem. Eur. J. 1997, 3, 1890;
95. b) V. V. Smirnov, E. K. Woller, D. Tatman, S. G. DiMagno, Inorg. Chem. 2001, 40, 2614.
96. X.-K. Jiang, Acc. Chem. Res. 1997, 30, 283.
97. L. K. Stultz, M. H. V. Huynh, R. A. Binstead, M. Curry, T. J. Meyer, J. Am. Chem. Soc. 2000, 122, 5984.
98. K. A. Gardner, L. L. Kuehnert, J. M. Mayer, Inorg. Chem. 1997, 36, 2069.
99. J. Kaizer, E. J. Klinker, N. Y. Oh, J.-U. Rohde, W. J. Song, A. Stubna, J. Kim, E. Münck, W. Nam, L. Que Jr., J. Am. Chem. Soc. 2004, 126, 472.
100. H. Lindler, R. Dubuis, Org. Synth. Collect. 1973, 5, 880.
101. a) R. L. Halterman, S.-T. Jan, J. Org. Chem. 1991, 56, 5253;
102. b) R. L. Halterman, S.-T. Jan, H. L. Nimmons, D. J. Standlee, M. A. Khan, Tetrahedron 1997, 55, 11257.