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Date: 13-01-15 19:15:41
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FULL PAPER
[20] W. Nam, Acc. Chem. Res. 2007, 40, 522–531.
30 min to remove excess m-CPBA, and the m-chlorobenzoic acid
by-product. After filtration and removal of the solvent, the re-
sulting crude product (0.14 g, 67% yield) was dissolved in a mini-
mal amount of MeOH and recrystallized at –30 °C to give the ana-
lytically pure product. Crystals suitable for X-ray analysis were
grown from a CH2Cl2 solution layered with hexane. FTIR (in hex-
[21] B. Meunier, S. P. de Visser, S. Shaik, Chem. Rev. 2004, 104,
3947–3980.
[22] T. Jiang, W. Wang, B. Han, New J. Chem. 2013, 37, 1654–1664.
[23] P. Borah, X. Ma, K. T. Nguyen, Y. Zhao, Angew. Chem. Int.
Ed. 2012, 51, 7756–7761.
[24] F. Shi, L. Mu, P. Yu, J. Hu, L. Zhang, J. Mol. Catal. A 2014,
ane): ν(CO): 2082, 2043, 2020, 1997, 1988 cm–1. 1H NMR
˜
391, 66–73.
(400 MHz, CDCl3): δ = 3.20 (m, 1 H, SCH), 2.10 (m, 1 H, SCH),
[25] C. Guo, W. Du, G. Chen, L. Shi, Q. Sun, Catal. Commun.
2013, 37, 19–22.
3
3
1.61 (d, JH,H = 6.4 Hz, 3 H, CH3C), 1.39 (d, JH,H = 6.4 Hz, 3 H,
CH3C) ppm. C10H8Fe2O7S2 (415.99): calcd. C 28.87, H 1.94, O
26.92; found C 28.79, H 2.02, O 26.83.
[26] R. Bal, M. Tada, T. Sasaki, Y. Iwasawa, Angew. Chem. Int. Ed.
2006, 45, 448–452; Angew. Chem. 2006, 118, 462.
[27] Y. Ichihashi, T. Taniguchi, H. Amano, T. Atsumi, S. Nishi-
yama, S. Tsuruya, Top. Catal. 2008, 47, 98–100.
[28] W. Lubitz, H. Ogata, O. Rüdiger, E. Reijerse, Chem. Rev. 2014,
114, 4081–4148.
[29] M. E. Carroll, B. E. Barton, T. B. Rauchfuss, P. J. Carroll, J.
Am. Chem. Soc. 2012, 134, 18843–18852.
[30] R. D. Bethel, M. L. Singleton, M. Y. Darensbourg, Angew.
Chem. Int. Ed. 2010, 49, 8567–8569.
Hydroxylation of benzene and other aromatic substrates with H2O2
was carried out in a 25 mL round-bottomed flask equipped with a
reflux condenser and a magnetic stirrer. In a typical reaction, the
model complex 1 was dissolved in CH3CN. After the mixture was
heated to the desired temperature, benzene or other substrates were
added to the mixture. Finally, a certain amount of H2O2 was added
to initiate the hydroxylation, and the mixture was stirred for several
hours. All the experiments were carried out at ambient pressure.
[31] C. Tard, C. J. Pickett, Chem. Rev. 2009, 109, 2245–2274.
[32] J. M. Camara, T. B. Rauchfuss, J. Am. Chem. Soc. 2011, 133,
8098–8101.
[33] J. M. Camara, T. B. Rauchfuss, Nat. Chem. 2012, 4, 26–30.
[34] T. Liu, B. Li, M. L. Singleton, M. B. Hall, M. Y. Darensbourg,
J. Am. Chem. Soc. 2009, 131, 8296–8307.
[35] J. Messelhäuser, K. U. Gutensohn, I.-P. Lorenz, W. Hiller, J.
Organomet. Chem. 1987, 321, 377–388.
[36] E. Y. Tshuva, S. J. Lippard, Chem. Rev. 2004, 104, 987–1012.
[37] D. Lee, S. J. Lippard, Inorg. Chem. 2002, 41, 2704–2719.
[38] M.-H. Baik, M. Newcomb, R. A. Friesner, S. J. Lippard, Chem.
Rev. 2003, 103, 2385–2419.
Acknowledgments
This work was supported by the National Natural Science Founda-
tion of China (NSFC) (grant numbers 21103121, 21276187,
21236001), the Research Fund for the Doctoral Program of Higher
Education of China (grant number 20110032120011), and the Tian-
jin Municipal Natural Science Foundation (grant number
13JCQNJC05800).
[39] C. E. Tinberg, S. J. Lippard, Acc. Chem. Res. 2011, 44, 280–
288.
[1] O. Shoji, T. Kunimatsu, N. Kawakami, Y. Watanabe, Angew.
Chem. Int. Ed. 2013, 52, 6606–6610.
[2] Z. Long, Y. Zhou, G. Chen, P. Zhao, J. Wang, Chem. Eng. J.
2014, 239, 19–25.
[3] R. Navarro, S. Lopez-Pedrajas, D. Luna, J. M. Marinas, F. M.
Bautista, Appl. Catal. A 2014, 474, 272–279.
[4] S. Niwa, M. Eswaramoorthy, J. Nair, A. Raj, N. Itoh, H. Shoji,
T. Namba, F. Mizukami, Science 2002, 295, 105–107.
[5] X. Chen, J. Zhang, X. Fu, M. Antonietti, X. Wang, J. Am.
Chem. Soc. 2009, 131, 11658–11659.
[6] V. M. Zakoshansky, Petroleum Chemistry 2007, 47, 273–284.
[7] L. Chen, Y. Xiang, T. Feng, Appl. Organomet. Chem. 2012, 26,
108–113.
[40] A. I. Stewart, I. P. Clark, M. Towrie, S. K. Ibrahim, A. W. Par-
ker, C. J. Pickett, N. T. Hunt, J. Phys. Chem. B 2008, 112,
10023–10032.
[41] S. Munery, J.-F. Capon, L. D. Gioia, C. Elleouet, C. Greco,
F. Y. Pétillon, P. Schollhammer, J. Talarmin, G. Zampella,
Chem. Eur. J. 2013, 19, 15458–15461.
[42] F. Quentel, G. Passard, F. Gloaguen, Chem. Eur. J. 2012, 18,
13473–13479.
[43] C. M. Thomas, O. Rüdiger, T. Liu, C. E. Carson, M. B. Hall,
M. Y. Darensbourg, Organometallics 2007, 26, 3976–3984.
[44] L. C. Song, C. G. Li, J. H. Ge, Z. Y. Yang, H. T. Wang, J.
Zhang, Q. M. Hu, J. Inorg. Biochem. 2008, 102, 1973–1979.
[45] R. Mejia-Rodriguez, D. Chong, J. H. Reibenspies, M. P. Sori-
aga, M. Y. Darensbourg, J. Am. Chem. Soc. 2004, 126, 12004–
12014.
[46] P. Li, M. Wang, C. He, G. Li, X. Liu, C. Chen, B. Åkermark,
L. Sun, Eur. J. Inorg. Chem. 2005, 2506–2513.
[47] D. Chong, I. P. Georgakaki, R. Mejia-Rodriguez, J. Sanabria-
Chinchilla, M. P. Soriaga, M. Y. Darensbourg, Dalton Trans.
2003, 4158–4163.
[48] I. P. Georgakaki, M. L. Miller, M. Y. Darensbourg, Inorg.
Chem. 2003, 42, 2489–2494.
[49] X. Zhao, I. P. Georgakaki, M. L. Miller, R. Mejia-Rodriguez,
C.-Y. Chiang, M. Y. Darensbourg, Inorg. Chem. 2002, 41,
3917–3928.
[8] Y. Li, H. Xia, F. Fan, Z. Feng, R. A. van Santen, E. J. M.
Hensen, C. Li, Chem. Commun. 2008, 774–776.
[9] S. Yang, G. Liang, A. Gu, H. Mao, Ind. Eng. Chem. Res. 2012,
51, 15593–15600.
[10] C. Walling, R. A. Johnson, J. Am. Chem. Soc. 1975, 97, 363–
367.
[11] C. L. Sun, B. J. Li, Z. J. Shi, Chem. Rev. 2011, 111, 1293–1314.
[12] C. Bolm, J. Legros, J. L. Paih, L. Zani, Chem. Rev. 2004, 104,
6217–6254.
[13] C. M. Krest, E. L. Onderko, T. H. Yosca, J. C. Calixto, R. F.
Karp, J. Livada, J. Rittle, M. T. Green, J. Biol. Chem. 2013,
288, 17074–17081.
[14] S. Friedle, E. Reisner, S. J. Lippard, Chem. Soc. Rev. 2010, 39,
[50] W. Dong, M. Wang, T. Liu, X. Liu, K. Jin, L. Sun, J. Inorg.
Biochem. 2007, 101, 506–513.
2768–2779.
[15] M. Costas, M. P. Mehn, M. P. Jensen, L. Que Jr., Chem. Rev.
2004, 104, 939–986.
[16] M. A. Culpepper, G. E. Cutsail, B. M. Hoffman, A. C. Ro-
senzweig, J. Am. Chem. Soc. 2012, 134, 7640–7643.
[17] G. Gopakumar, P. Belanzoni, E. J. Baerends, Inorg. Chem.
2012, 51, 63–75.
[18] S. J. Lee, M. S. McCormick, S. J. Lippard, U. S. Cho, Nature
2013, 494, 380–384.
[19] H. Sun, M. Wang, F. Li, P. Li, Z. Zhao, L. Sun, Appl. Or-
ganomet. Chem. 2008, 22, 573–576.
[51]
[52]
[53]
J. Windhager, R. A. Seidel, U.-P. Apfel, H. Görls, G. Linti, W.
Weigand, Chem. Biodiversity 2008, 5, 2023–2041.
M. Y. Darensbourg, W. Weigand, Eur. J. Inorg. Chem. 2011,
994–1004.
J. Windhager, M. Rudolph, S. Bräutigam, H. Görls, W. Wei-
gand, Eur. J. Inorg. Chem. 2007, 2748–2760.
T. Vannelli, A. B. Hooper, Biochemistry 1995, 34, 11743–11749.
G. Sheldrick, SHELXS-97, Program for Crystal Structure Solu-
tion, University of Göttingen, Germany, 1997.
[54]
[55]
Eur. J. Inorg. Chem. 0000, 0–0
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