Substrate oxidation by copper-dioxygen adducts: Mechanistic considerations

Journal of the American Chemical Society

Volumn 127, Issue 15, 2005, Pages 5469-5483

  Shearer, Jason ^a   Zhang, Christiana Xin ^a   Zakharov, Lev N ^b   Rheingold, Arnold L ^b,c   Karlin, Kenneth D ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; DISSOCIATION; ENTHALPY; OXIDATION; REACTION KINETICS; REDOX REACTIONS; THERMODYNAMICS;

1R TETRAHYDROFURAN (THF); ELECTRON-TRANSFER PROTON-TRANSFER (ETPT); N,N′-DIMETHYLANILINE (DMA); N-CYCLOPROPYL-N-METHYLANILINE (CMA); PROTON-COUPLED ELECTRON-TRANSFER (PCET);

COPPER COMPOUNDS;

ANILINE DERIVATIVE; COPPER; LIGAND; OXYGEN; PYRIDINE DERIVATIVE; TETRAHYDROFURAN;

ARTICLE; CHEMICAL BOND; DISSOCIATION CONSTANT; ELECTRON TRANSPORT; ENTHALPY; LIGAND BINDING; MOLECULAR INTERACTION; MOLECULAR MECHANICS; OXIDATION KINETICS; OXIDATION REDUCTION REACTION; STRUCTURE ANALYSIS; THERMODYNAMICS;

ANILINE COMPOUNDS; COPPER; CRYSTALLOGRAPHY, X-RAY; ELECTRON SPIN RESONANCE SPECTROSCOPY; FURANS; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; OXYGEN; PYRIDINES; THERMODYNAMICS;

EID: 17644419940     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045191a     Document Type: Article

References (98)

1. Kitajima, N.; Moro-oka, Y. Chem. Rev. 1994, 94, 737-757.
2. Solomon, E. I.; Sundaram, U. M.; Machonkin, T. E. Chem. Rev. 1996, 96, 2563-2605.
3. Klinman, J. P. Chem. Rev. 1996, 96, 2541-2561.
4. Kopf, M.-A.; Karlin, K. D. In Biomimetic Oxidations; Meunier, B., Ed.; Imperial College Press: London, 2000; Chapter 7, pp 309-362.
5. Solomon, E. I.; Chen, P.; Metz, M.; Lee, S.-K.; Palmer, A. E. Angew. Chem., Int. Ed. 2001, 40, 4570-4590.
6. Que, L., Jr.; Tolman, W. B. Angew. Chem., Int. Ed. 2002, 41, 1114-1137.
7. Quant Hatcher, L.; Karlin, K. D. J. Biol. Inorg. Chem. 2004, 9, 669-683.
8. Mirica, L. M.; Ottenwaelder, X.; Stack, T. D. P. Chem. Rev. 2004, 104, 1013-1045.
9. Lewis, E. A.; Tolman, W. B. Chem. Rev. 2004, 104, 1047-1076.
10. Decker, H.; Dillinger, R.; Tuczek, F. Angew. Chem., Int. Ed. 2000, 39, 1591-1595.
11. Gerdemann, C.; Eicken, C.; Krebs, B. Acc. Chem. Res. 2002, 35, 183-191.
12. Evans, J. P.; Ahn, K.; Klinman, J. P. J. Biol. Chem. 2003, 278, 49691-49698.
13. Chen, P.; Bell, J.; Eipper, B. A.; Solomon, E. I. Biochemistry 2004, 43, 5735-5747.
14. (a) Chen, P.; Solomon, E. I. J. Am Chem. Soc. 2004, 126, 4991-5000.
15. (b) Chen, P.; Solomon, E. I. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 13105-13110.
16. Prigge, S. T.; Eipper, B.; Mains, R.; Amzel, L. M. Science 2004, 304, 864-867.
17. Sanchez-Ferrer, A.; Rodriguez-Lopez, J. N.; Garcia-Canovas, F.; Garcia-Carmona, F. Biochim. Biophys. Acta 1995, 1247, 1-11.
18. Pidcock, E.; Obias, H. V.; Zhang, C. X.; Karlin, K. D.; Solomon, E. I. J. Am. Chem. Soc. 1998, 120, 7841-7847.
19. Itoh, S.; Kumei, H.; Taki, M.; Nagatomo, S.; Kitagawa, T.; Fukuzumi, S. J. Am. Chem. Soc. 2001, 123, 6708-6709.
20. Yamazaki, S.-i.; Itoh, S. J. Am Chem. Soc. 2003, 125, 13034-13035.
21. Klabunde, T.; Eicken, C.; Sacchettini, J. C.; Krebs, B. Nat. Struct. Biol. 1998, 5, 1084-1090.
22. Stack, T. D. P. Dalton Trans. 2003, 1881-1889.
23. Karlin, K. D.; Gultneh, Y. Prog. Inorg. Chem. 1987, 35, 219-327.
24. Oxidation in Organic Chemistry; Trahanovsky, W. S., Ed.; Academic Press: New York, 1973; Vol. Part B, Chapter 1.
25. Sprecher, C. A.; Zuberbühler, A. D. Angew. Chem., Int. Ed. Engl. 1977, 16, 189.
26. Gampp, H.; Zuberbühler, A. D. Met. Ions Biol. Syst. 1981, 12, 133-189.
27. Zuberbühler, A. D. In Copper Coordination Chemistry: Biochemical and Inorganic Perspectives; Karlin, K. D., Zubieta, J., Eds.; Adenine: Guilderland, NY, 1983; pp 237-258.
28. Reglier, M.; Amadei, E.; Alilou, E. H.; Eydoux, F.; Pierrot, M.; Waegell, B. Bioinorg. Chem. Copper 1993, 348-362.
29. Mahapatra, S.; Young, V. G., Jr.; Kaderli, S.; Zuberbühler, A. D.; Tolman, W. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 130-133.
30. Mahadevan, V.; Hou, Z.; Cole, A. P.; Root, D. E.; Lal, T. K.; Solomon, E. I.; Stack, T. D. P. J. Am. Chem. Soc. 1997, 119, 11996-11997.
31. Taki, M.; Itoh, S.; Fukuzumi, S. J. Am. Chem. Soc. 2001, 123, 6203-6204.
32. Mahapatra, S.; Halfen, J. A.; Tolman, W. B. J. Am. Chem. Soc. 1996, 118, 11575-11586.
33. Cramer, C. J.; Kinsinger, C. R.; Pak, Y. THEOCHEM 2003, 632, 111-120.
34. Cramer, C. J.; Pak, Y. Theor. Chem. Acc. 2001, 105, 477-480.
35. Cukier, R. I. J. Phys. Chem. B 2002, 106, 10089-10100.
36. Since the specifics of these reactions are unknown from a theoretical standpoint (i.e., we do not know if the electron and proton are going to the same (a hydrogen atom transfer (HAT)) or different (a concerted PCET) acceptor orbitals), we prefer to use Cukier's more general nomenclature (ref 34) for thermodynamically coupled proton/electron-transfer reactions. Here, "ETPT" means that the ET and PT occur in one kinetically irresolvable step, while "ET/PT" designates that the ET and PT processes can be broken down into two kinetically resolvable steps, with the ET event occurring prior to proton transfer (PT).
37. Fukuzumi, S.; Ohtsu, H.; Ohkubo, K.; Itoh, S.; Imahori, H. Coord. Chem. Rev. 2002, 226, 71-80.
38. Mahadevan, V.; Henson, M. J.; Solomon, E. I.; Stack, T. D. P. J. Am. Chem. Soc. 2000, 122, 10249-10250.
39. Mahadevan, V.; DuBois, J. L.; Hedman, B.; Hodgson, K. O.; Stack, T. D. P. J. Am. Chem. Soc. 1999, 121, 5583-5584.
40. Osako, T.; Ohkubo, K.; Taki, M.; Tachi, Y.; Fukuzumi, S.; Itoh, S. J. Am. Chem. Soc. 2003, 125, 11027-11033.
41. Itoh, S.; Kumei, H.; Nagatomo, S.; Kitagawa, T.; Fukuzumi, S. J. Am. Chem. Soc. 2001, 123, 2165-2175.
42. Taki, M.; Teramae, S.; Nagatomo, S.; Tachi, Y.; Kitagawa, T.; Itoh, S.; Fukuzumi, S. J. Am. Chem. Soc. 2002, 124, 6367-6377.
43. (a) Zhang, C. X.; Liang, H.-C.; Kim, E.-i.; Shearer, J.; Helton, M. E.; Kim, E.; Kaderli, S.; Incarvito, C. D.; Zuberbühler, A. D.; Rheingold, A. L.; Karlin, K. D. J. Am Chem. Soc. 2003, 125, 634-635.
44. (b) Liang, H.-C.; Karlin, K. D.; Dyson, R.; Kaderli, S.; Jung, B.; Zuberbühler, A. D. Inorg. Chem. 2000, 39, 5884-5894.
45. Henson, M. J.; Vance, M. A.; Zhang, C. X.; Liang, H.-C.; Karlin, K. D.; Solomon, E. I. J. Am. Chem. Soc. 2003, 125, 5186-5192.
46. Shearer, J.; Zhang, C. X.; Hatcher, L. Q.; Karlin, K. D. J. Am. Chem. Soc. 2003, 125, 12670-12671.
47. Shaffer, C. L.; Harriman, S.; Koen, Y. M.; Hanzlik, R. P. J. Am. Chem. Soc. 2002, 124, 8268-8274.
48. Baciocchi, E.; Bietti, M.; Lanzalunga, O. Acc. Chem. Res. 2000, 33, 243-251.
49. Shaffer, C. L.; Morton, M. D.; Hanzlik, R. P. J. Am. Chem. Soc. 2001, 123, 349-350.
50. Baciocchi, E.; Bietti, M.; Putignani, L.; Steenken, S. J. Am. Chem. Soc. 1996, 118, 5952-5960.
51. Mader, E. A.; Larsen, A. S.; Mayer, J. M. J. Am. Chem. Soc. 2004, 126, 8066-8067.
52. Cui, W.; Loeppky, R. N. Tetrahedron 2001, 57, 2953-2956.
53. Smyth, T. P.; Corby, B. W. J. Org. Chem. 1998, 63, 8946-8951.
54. Hammond, P. R. U.S. Patent Appl. 566,924, November 9, 1984.
55. LeSuer, R. J.; Geiger, W. E. Angew. Chem., Int. Ed. 2000, 39, 248-250.
56. Armarego, C. Purification of Laboratory Chemicals, 5th ed.; Butterworth Heinemann: New York, 2003.
57. Gampp, H.; Maeder, M.; Meyer, C. J.; Zuberbühler, A. D. Talanta 1985, 32, 95-110.
58. Wilkins, R. G. Kinetics and Mechanism of Reactions of Transition Metal Complexes, 2nd ed.; VCH: New York, 1991.
59. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry, 5th ed.; Pearson Education Ltd.: Essex, England, 1989.
60. Thorp, H. H.; Sarneski, J. E.; Brudvig, G. W.; Crabtree, R. H. J. Am. Chem. Soc. 1989, 111, 9249-9250.
61. Obias, H. V.; Lin, Y.; Murthy, N. N.; Pidcock, E.; Solomon, E. I.; Ralle, M.; Blackburn, N. J.; Neuhold, Y.-M.; Zuberbühler, A. D.; Karlin, K. D. J. Am. Chem. Soc. 1998, 120, 12960-12961.
62. Berkowitz, J.; Ellison, G. B.; Gutman, D. J. Phys. Chem. 1994, 98, 2744-2765.
63. Laarhoven, L. J. J.; Mulder, P. J. Phys. Chem. B 1997, 101, 73-77.
64. Due to the low yields and low molecular weights of products in diethyl ether oxidations, we were only able to confirm that an aldehyde was produced. This suggests an oxidative O-dealkylation through a rebound-like process.
65. Bordwell, F. G.; Liu, W.-Z. J. Am. Chem. Soc. 1996, 118, 10819-10823.
66. R).
67. Bordwell, F. G.; Cheng, J.; Ji, G. Z.; Satish, A. V.; Zhang, X. J. Am. Chem. Soc. 1991, 113, 9790-9795.
68. Izutsu, K. Acid-Base Dissociation Constants in Dipolar Aprotic Solvents; Blackwell Scientific Publications: Oxford, U.K., 1990; Chemical Data Series, No. 35.
69. Pidcock, E.; DeBeer, S.; Obias, H. V.; Hedman, B.; Hodgson, K. O.; Karlin, K. D.; Solomon, E. I. J. Am. Chem. Soc. 1999, 121, 1870-1878.
70. Chan, S. I.; Chen, K. H. C.; Yu, S. S. F.; Chen, C. L.; Kuo, S. S. J. Biochemistry 2004, 43, 4421-4430.
71. Zhang, C. X. Johns Hopkins University, 2001.
72. Obias, H. V. Johns Hopkins University, 1998.
73. 42
74. (a) Karlin, K. D.; Kaderli, S.; Zuberbühler, A. D. Acc. Chem. Res. 1997, 30, 139-147.
75. (b) Zhang, C. X.; Kaderli, S.; Costas, M.; Kim, E.-i.; Neuhold, Y.-M.; Karlin, K. D.; Zuberbühler, A. D. Inorg. Chem. 2003, 42, 1807-1824.
76. eq values, which leads to uncertainty in the calculated ΔS° term. See further details in the Discussion.
77. Ambundo, E. A.; Friesner, R. A.; Lippard, S. J. J. Am. Chem. Soc. 2002, 124, 8770-8771.
78. Shaffer, C. L.; Harriman, S.; Koen, Y. M.; Hanzlik, R. P. J. Am. Chem. Soc. 2002, 124, 8268-8274.
79. Bhakta, M. N.; Wimalasena, K. J. Am. Chem. Soc. 2002, 124, 1844-1845.
80. Attempts were made to obtain a pure standard of PMA. These attempts all yielded impure material which quickly decomposed into a brown polymeric substance, presumably due to inter- and intramolecular iminium formation between the aldehyde and methylamine moiety.
81. No change in product distributions is noted if the reaction temperature is increased to -60°C, which is the highest temperature at which these complexes will cleanly oxidize substrates.
82. Addison, A. W.; Rao, T. N.; Reedijk, J.; van Rijn, J.; Verschoor, G. C. J. Chem. Soc., Dalton Trans. 1984, 1349-1356.
83. Machonkin, T. E.; Mukherjee, P.; Henson, M. J.; Stack, T. D. P.; Solomon, E. I. Inorg. Chim. Acta 2002, 341, 39-44.
84. Cole, A. P.; Root, D. E.; Mukherjee, P.; Solomon, E. I.; Stack, T. D. P. Science 1996, 273, 1848-1850.
85. Root, D. E.; Henson, M. J.; Machonkin, T.; Mukherjee, P.; Stack, T. D. P.; Solomon, E. I. J. Am. Chem. Soc. 1998, 120, 4982-4990.
86. (a) Mayer, J. M. Acc. Chem. Res. 1998, 31, 441-450.
87. (b) Roth, J. P.; Yoder, J. C.; Won, T.-J.; Mayer, J. M. Science 2001, 294, 2524-2526.
88. Kim, H.-s.; Chung, T. D.; Kim, H. J. Electroanal. Chem. 2001, 498, 209-215.
89. Itoh, S.; Kumei, H.; Taki, M.; Nagatomo, S.; Kitagawa, T.; Fukuzumi, S. J. Am. Chem. Soc. 2001, 123, 6708-6709.
90. The phenolate oxidations reported by Itoh were carried out in acetone. This solvent may compete somewhat with phenolate coordination, which could suppress phenolate binding constants in this system.
91. -Ea/RT.
92. Shaffer, C. L.; Morton, M. D.; Hanzlik, R. P. J. Am. Chem. Soc. 2001, 123, 8502-8508.
93. Sato, H.; Guengerich, F. P. J. Am. Chem. Soc. 2000, 122, 8099-8100.
94. Hall, L. R.; Hanzlik, R. P. J. Biol. Chem. 1990, 265, 12349-12355.
95. Bryant, J. R.; Taves, J. E.; Mayer, J. M. Inorg. Chem. 2002, 41, 2769-2776.
96. Mahapatra, S.; Halfen, J. A.; Wilkinson, E. C.; Pan, G.; Wang, X.; Young, V. G., Jr.; Cramer, C. J.; Que, L., Jr.; Tolman, W. B. J. Am. Chem. Soc. 1996, 118, 11555-11574.
97. Henson, M. J.; Mukherjee, P.; Root, D. E.; Stack, T. D. P.; Solomon, E. I. J. Am. Chem. Soc. 1999, 121, 10332-10345.
98. Me2N.