Copper(II)-mediated aromatic orth-hydroxylation: A hybrid DFT and Ab initio exploration

Chemistry - A European Journal

Volumn 14, Issue 1, 2008, Pages 344-357

  Comba, Peter ^a   Knoppe, Stefan ^a   Martin, Bodo ^a   Rajaraman, Gopalan ^a   Rolli, Claudio ^a   Shapiro, Brett ^a   Stork, Timon ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Ab initio calculations; Copper; Hydroxylation; Reaction mechanisms; Solvent effects

Indexed keywords

AROMATIC COMPOUNDS; CARBOXYLIC ACIDS; DENSITY FUNCTIONAL THEORY; ELECTRONIC STRUCTURE; HYDROXYLATION; REACTION KINETICS;

AB INITIO CALCULATIONS; PCM MODEL; SOLVENT EFFECTS;

COPPER COMPOUNDS;

BORANE DERIVATIVE; COPPER; PHOSPHINE; PHOSPHINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; HYDROXYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TEMPERATURE; X RAY CRYSTALLOGRAPHY;

BORANES; COMPUTER SIMULATION; COPPER; CRYSTALLOGRAPHY, X-RAY; HYDROXYLATION; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHOSPHINES; TEMPERATURE;

EID: 84962367582     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700865     Document Type: Article

References (131)

1. R. A. Sheldon, J. K. Kochi, Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981.
2. Y. Lee, K. D. Karlin in Concepts and Models in Bioinorganic Chemistry (Eds.; H.-B. Kraatz, N. Metzler-Nolte), Wiley-VCH, Weinheim, 2006.
3. R. Ullrich, M. Hofrichter, Cell. Mol. Life Sci. 2007, 64, 271.
4. O. Toussaint, K. Lerch, Biochemistry 1987, 26, 8567.
5. L. Q. Hatcher, K. D. Karlin, J. Biol. Inorg. Chem. 2004, 9, 669.
6. E. A. Lewis, W. B. Tolman, Chem. Rev. 2004, 104, 1047.
7. L. M. Mirica, X. Ottenwaelder, T. D. P. Stack. Chem. Rev. 2004, 104, 1013.
8. K.-F. Wedemeyer in Methoden der Organischen Chemie (Eds. J. Houben, T. Weyl), Georg Thieme Verlag, Stuttgart, 1976, p. 4.
9. S. Udenfried, C. T. Clark, A. J. B. Brodie, J. Biol. Chem. 1954, 208, 731.
10. A. Leman, M. T. Montaigne, Acad. Sci. 1950, 231, 412.
11. H. Loebl, G. Stein, J. Weiss, J. Chem. Soc. 1951, 405.
12. H. J. H. Fenton, J. Chem. Soc. 1894, 65, 899.
13. W. W. Kaeding, G. R. Colling, J. Org. Chem. 1965, 30, 3750.
14. W. W. Kaeding, A. T. Shulgin, J. Chem. Soc. 1953, 288, 3551.
15. W. Buijs, DSM Res. Commun. 1993, 4.
16. W. Buijs, J. Mol. Catal. A 1999, 146, 237.
17. W. Buijs, P. Comba, D. Corneli, Y. Mengerink, H. Pritzkow, M. Schickedanz, Eur. J. Inorg. Chem. 2001, 3143.
18. G. S. Bull, G. H. Searle, J. Chem. Educ. 1986, 63, 902.
19. S. J. Lange, H. Miyake, L. Que, Jr., J. Am. Chem. Soc. 1999, 121, 6330.
20. M. P. Jensen, S. J. Lange, M. P. Mehn, L. E. Que, L. Que, Jr., J. Am. Chem.Soc. 2003, 125, 2113.
21. N. Kitajima, M. Ito, H. Fukui, Y. Moro-oka, J. Am. Chem. Soc. 1993, 115, 9335.
22. T. Funabiki, T. Yokomizo, S. Suzuki, S. Yoshida, Chem. Commun. 1997, 151.
23. S. Menage, J.-B. Galey, J. Dumats, G. Hussler, M. Seite, I. G. Luneau, G. Chottard, M. Fontecave, J. Am. Chem. Soc. 1998, 120, 13370.
24. Y. Mekmouche, S. Menage, C. Toia-Duboc, M. Fontecave, J.-B. Galey, C. Lebrun, J. Pecaut. Angew. Chem. 2001, 113, 975;
25. Angew. Chem. Int. Ed. 2001, 40, 949.
26. M. P. Mehn, K. Fujisawa, E. L. Hegg, L. Que, Jr., J. Am. Chem. Soc. 2003, 125, 7828.
27. F. Avenier, J. L. DuBois, J.-M. Latour, New J. Chem. 2004, 28, 782.
28. S. Taktak, M. Flook, B. M. Foxman, L. Que, Jr., E. V. Rybak-Akimova, Chem. Commun. 2005, 5301.
29. N. Y. Oh, M. S. Seo, M. H. Lim, M. B. Consugar, M. J. Park, J.-U. Rohde, J. Han, K.M. Kim, J. Kim, L. Que, Jr., W. Nam, Chem. Commun. 2005, 5644.
30. S. P. De Visser, K. Oh, A.-R. Han, W. Nam, Inorg. Chem. 2007, 46, 4632.
31. E. I. Solomon, T. C. Brunold, M. I. Davis, J. N. Kemsley, S.-K. Lee, N. Lehnert, F. Neese, A. J. Skulan, Y.-S. Yang, J. Zhou, Chem. Rev. 2000, 100, 235.
32. M. Costas, M. P. Mehn, M. P. Jensen, L. Que, Jr., Chem. Rev. 2004, 104, 939.
33. J.-U. Rohde, J.-H. In, M. H. Lim, W. W. Brennessel, M. R. Bukowski, A. Stubna, E. Münck, W. Nam. L. Que, Jr., Science 2003, 299, 1037.
34. M. R. Bukowski, P. Comba, A. Lienke, C. Limberg, C. Lopez de Laorden, R. Mas-Balleste, M. Merz, L. Que, Jr., Angew. Chem. 2006, 118, 3524;
35. Angew. Chem. Int. Ed. 2006, 45, 3446.
36. O. Reinaud, P. Capdevielle, M. Maumy, Synthesis 1990, 612.
37. O. Reinaud, P. Capdevielle, M. Maumy, J. Chem. Soc. Chem. Commun. 1990, 566.
38. P. Capdevielle, D. Sparfel, J. Baranne-Lafont, N. K. Cuong, M. Maumy, J. Chem. Soc. Chem. Commun. 1990, 565.
39. P. Capdevielle, M. Maumy, Tetrahedron Lett. 1982, 23, 1573.
40. O. Reinaud, P. Capdevielle, M. Maumy, J. Mol. Catal. 1991, 68, 13.
41. W. Buijs, P. Comba, D. Corneli, H. Pritzkow, J. Organomet. Chem. 2002, 641, 71.
42. J. P. Evans, K. Ahn, J. P. Kliman, J. Biol. Chem. 2003, 278, 49691.
43. T. Kamachi, N. Kihara, Y. Shiota, K. Yoshizawa, Inorg. Chem. 2005, 44, 4226.
44. K. Yoshizawa, Y. Shiota, J. Am. Chem. Soc. 2006, 128, 9873.
45. S. Miertus, E. Scrocco, J. Tomasi, Chem. Phys 1981, 55, 117.
46. V. Barone, M. Cossi, J. Phys Chem. A 1998, 102, 1995.
47. A. Klamt, G. Schürmann, J. Chem. Soc., Perkin Trans. 2 1993, 799.
48. J. A. Pople, M. Head-Gordon, K. Raghavachari, J. Chem. Phys. 1987, 87, 5968.
49. J. Cizek, Adv. Chem. Phys. 1969, 14, 35.
50. G. D. Purvis, R. J. Bartlett, J. Chem. Phys. 1982, 76, 1910.
51. G. E. Scuseria, C. L. Janssen, H. F. Schaefer, J. Chem. Phys. 1988, 89, 7382.
52. G. E. Scuseria, H. F. Schaefer, J. Chem. Phys. 1989, 90, 3700.
53. M. J. Frisch, G.W. Trucks, H.B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D, K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen. M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision B.03, Vol. Gaussian Inc., Wallingford CT, 2003.
54. JAGUAR 5.5, Schrödinger Inc., Portland, OR.
55. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
56. A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
57. T. H. Dunning, Jr., P. J. Hay in Modern Theoretical Chemistry, Vol. 3 (Ed. : H. F. Schaefer III), Plenum, New York, 1976, pp. 1.
58. P. J. Hay, W. R. Wadt, J. Chem. Phys 1985, 82, 270.
59. W. R. Wadt, P. J. Hay, J. Chem. Phys. 1985, 82, 284.
60. P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 299.
61. R. Ditchfield, W. J. Hehre, J. A. Pople, J. Chem. Phys. 1971, 54, 724.
62. A. Schaefer, H. Horn, R. Ahlrichs, J. Chem. Phys. 1992, 97, 2571.
63. A. Schäfer, C. Huber, R. Ahlrichs, J. Chem. Phys. 1994, 100, 5829.
64. P. Flükiger, H. P. Lüthi, S. Portmann, J. Weber, MOLEKEL 4.3, Swiss Center for Scientific Computing, Manno, Switzerland, 2000.
65. S. Portmann, H. P. Lüthi. CHIMIA 2000, 54, 766.
66. M. T. Cancès, B. Mennucci, J. Tomasi, J. Chem. Phys. 1997, 107, 3032.
67. M. Cossi, B. Barone, B. Mennucci, J. Tomasi, Chem. Phys. Lett. 1998, 286, 253.
68. B. Mennucci, J. Tomasi, J. Chem. Phys. 1997, 106, 5151.
69. M. Cossi, G. Scalmani, N. Rega, V. Barone, J. Chem. Phys. 2002, 117, 43.
70. -1 at the Jaguar B3LYP/BSI level.
71. N. Kitajima, T. Koda, Y. Iwata, Y. Moro-oka, J. Am. Chem. Soc. 1990, 112, 8833.
72. N. Kitajima, Y. Moro-oka, Chem. Rev. 1994, 94, 737.
73. O. Kahn, Molecular Magnetism, Wiley, New York, 1993.
74. C. Würtele, E. Gaoutchenova, K. Harms, M. C. Holthausen, J. Sundermeyer, S. Schindler, Angew. Chem. 2006, 118, 3951;
75. Angew. Chem. Int. Ed. 2006, 45, 3867.
76. III-O converges to a closed-shell species.
77. J. M. Meyer, Comm. Inorg. Chem. 1998, 8, 125.
78. C. M. Barthelt, L. Ridder, A. J. Mulholland, J. N. Harvey, J. Am. Chem. Soc. 2005, 127, 12900.
79. In the mechanism of the related Fe=O-catalyzed aromatic hydroxylation by P450 two orientations of benzene with respect to the metal-oxo group have been described (see Ref. [75]). Here, we describe an intramolecular process in which only one of the orientations is possible., Vol.
80. 32 is the ground state for the reactant all energy barriers are given with respect to the ground state regardless of the spin surfaces.
81. P. Spuhler, M. C. Holthausen, Angew. Chem. 2003, 115, 6143;
82. Angew. Chem. Int. Ed. 2003, 42, 5961.
83. A. Fiedler, D. Schröder, S. Shaik, H. Schwarz, J. Am. Chem. Soc. 1994, 116, 10734.
84. S. Shaik, D. Danovich, A. Fiedler, D. Schröder, H. Schwarz, Helv. Chim. Acta 1995, 78, 1393.
85. D. Schröder, S. Shaik, H. Schwarz, Acc. Chem. Res. 2000, 33, 139.
86. S. Shaik, H. Hirao, D. Kumar, Acc. Chem. Res. 2007, 40, 532.
87. D. Schröder, M. C. Holthausen, H. Schwarz, J. Phys. Chem. B 2004, 108, 14407.
88. Y. Shiota, K. Yoshizawa, J. Chem. Phys. 2003, 118, 5872.
89. M. Kondo, K. Yoshizawa, Chem. Phys. Lett. 2003, 372, 519.
90. The intermediates and the transition state on the other spin surfaces have not been converged to the correct wave function and are, therefore, not included.
91. A. Kunishita, J. Teraoka, J. D. Scanlon, T. Matsumoto, M. Suzuki, C. J. Cramer, S. Itoh. J. Am. Chem.Soc 2007, 129, 7248.
92. H. Li, H. Jemsen, J. Comput. Chem. 2004, 25, 1449.
93. D. F. Raffa, G. A. Rickard, A. Rauk, J. Biol. Inorg. Chem. 2007, 12, 147.
94. J. P. Holland, J. C. Green, J. R. Dilworth, Dalton Trans. 2006, 783.
95. L. Barrio, J. M. Campos-Martin, J. L. G. Fierro, J. Phys. Chem. A 2007, 111, 2166.
96. W. H. Lam, E. C. Cheng, V. W. Yam. Inorg. Chem. 2006, 45, 9434.
97. A. A. Jarzecki, A. D. Anbar, T. G. Spiro, J. Phys. Chem. A 2004, 108, 2726.
98. K. Sugimori, T. Shuku, A. Sugiyama, H. Nagao, T. Sakurai, K. Nishikawa, Polyhedron 2005, 24, 2671.
99. J. M. H. Lo, M. Klobukowski, Inorg. Chim. Acta 2003, 353, 15.
100. See Supporting Information for the computed energies of the solvated species with different solvation models in comparison with the gas-phase energies.
101. 13 surface could not be successfully optimized by using the CPCM solvation model.
102. D. L. Reid, G. V. Shustov, D. A. Armstrong, A. Rauk, M. N. Schuchmann, M. S. Akhlaq. M. Shahid, C. von Sonntag, Phys. Chem. 2002, 4, 2965.
103. S. Wolfe, C.-K. Kim, K. Yang, N. Weingerg, Z. Shi, J. Am. Chem. Soc. 1995, 117, 4240.
104. S. Wolfe, Z. Shi, K. Yang, S. Ro, N. Weingerg, C.-K. Kim, Can. J. Chem. 1998, 76, 114.
105. S. P. de Visser, F. Ogliaro, N. Harris, S. Shaik, J. Am. Chem. Soc 2001, 123, 3037.
106. A. Bassan, M. R. A. Blomberg, P. E. M. Siegbahn, Chem. Eur. J. 2003, 9, 4055.
107. A. Bassan, M. R. A. Blomberg, P. E. M. Siegbahn, J. Biol. Inorg. Chem. 2004, 9, 439.
108. A. Bassan, M. R. A. Blomberg, P. E. M. Siegbahn, L. Que, Jr., Chem. Eur. J. 2005, 11, 692.
109. D. Quinonero, K. Morokuma, D. G. Musaev, K. Morokuma, R. Mas-Balleste, L. Que, Jr., J. Am. Chem. Soc. 2005, 126, 6548.
110. J. N. Harvey, Annu. Rep. Prog. Chem. Sed. C 2006, 102, 203.
111. P. E. M. Siegbahn, T. Borowski, Acc. Chem. Res. 2006, 39, 729.
112. S. Shaik, D. Kumar, S. P. De Visser, A. Altum, W. Thiel. Chem. Rev. 2005, 105, 2279.
113. B. Meunier, S. P. de Visser, S. Shaik, Chem. Rev. 2004, 104, 3947.
114. B. F. Gherman, C. J. Cramer, Inorg. Chem. 2004. 43, 7281.
115. E. Ruiz, S. Alvarez, A. Rodriguez-Fortea, P. Alemany, Y. Pouillon, C. Massobrio, Magnetism: Molecules to Materials Vol. 3 (Eds.: J. S. Miller, M. Drillon), Wiley-VCH, Weinheim, 2001.
116. P. E. M. Siegbahn, J. Biol. Inorg. Chem. 2006, 11, 695.
117. F. Neese, J. Inorg. Biochem. 2006, 100, 716.
118. F. Neese, J. Biol. Inorg. Chem. 2006, 11, 702.
119. A. Ghosh, J. Biol. Inorg. Chem. 2006, 11, 712.
120. T. J. Lee, A. P. Rendell, P. R. Taylor. J. Phys. Chem. 1990, 94, 5463.
121. S. Niu, M. B. Hall, J. Phys. Chem. A 1997, 101, 1360.
122. B. G. Johnson, P. M. W. Gill, J. A. Pople, J. Chem. Phys. 1993, 98, 5612.
123. Therefore, the reported barrier for the model complex using DFT, QCISD and CCSD calculations does not include ZPE or free-energy corrections.
124. M. Atanasov, P. Comba, B. Martin, V. Müller, G. Rajaraman, H. Rohwer, S. Wunderlich, J. Comput. Chem. 2006, 27, 1263.
125. R. K. Szilagyi, M. Metz, E. I. Solomon. J. Phys. Chem. A 2002, 106, 2994.
126. S. DeBeer George, L. Basumallick, R. K. Szilagyi, D.W. Randall, M. G. Hill, A. M. Nersissian, J. S. Valentine, B. Hedman, K. O. Hodgson, E. I. Solomon, J. Am. Chem. Soc. 2003, 125, 11314.
127. R. J. Deeth, J. Chem. Soc. Dalton Trans. 2001, 664.
128. J. H. Harvey, Struct. Bonding 2004, 112, 151.
129. J. K. Kang, C. B. Musgrave, J. Chem. Phys. 2001, 115, 11040.
130. B. J. Lynch, P. L. Fast, M. Harris, D. G. Truhlar, J. Phys. Chem. A 2000, 104, 4811.
131. Note that it is not unlikely that the B3LYP calculations are more reliable than the CCSD results because of the use of a minimal basis set for the CCSD calculations.