A high-valent iron-oxo corrolazine activates C-H bonds via hydrogen-atom transfer

Journal of the American Chemical Society

Volumn 134, Issue 17, 2012, Pages 7392-7399

  Cho, Kevin ^a   Leeladee, Pannee ^a   McGown, Amanda J ^a   Debeer, Serena ^b,c   Goldberg, David P ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b Department of Molecular Biology and Genetics   (United States)

^c MAX PLANCK INSTITUTE FOR CHEMICAL ENERGY CONVERSION   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION PARAMETER; C-H BOND; COMPOUND I; HYDROGEN-ATOM TRANSFER; INTRINSIC REACTIVITY; KINETIC DATA; LINEAR CORRELATION; PRODUCT ANALYSIS; REACTION TEMPERATURE;

HYDROGEN; HYDROGEN BONDS; PORPHYRINS; RADIOACTIVITY LOGGING; SUBSTRATES;

FREE RADICAL REACTIONS;

CARBON; HEME DERIVATIVE; HYDROGEN; IRON; OXIDIZING AGENT; PHENYL GROUP; XANTHENE;

ARTICLE; ATOM; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; COMPLEX FORMATION; DIMERIZATION; ELECTRON TRANSPORT; HYDROXYLATION; OXIDATION; PROTON TRANSPORT; REACTION ANALYSIS; TEMPERATURE;

DIMERIZATION; FERRIC COMPOUNDS; HYDROGEN; HYDROXYLATION; KINETICS; MODELS, MOLECULAR; OXIDANTS; OXIDATION-REDUCTION; OXYGEN; TEMPERATURE; XANTHENES;

EID: 84860822526     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3018658     Document Type: Article

References (74)

1. Shaik, S.; Kumar, D.; de Visser, S. P.; Altun, A.; Thiel, W. Chem. Rev. 2005, 105, 2279-2328
2. Meunier, B.; de Visser, S. P.; Shaik, S. Chem. Rev. 2004, 104, 3947-3980
3. Rittle, J.; Green, M. T. Science 2010, 330, 933-937
4. Makris, T. M.; von Koenig, K.; Schlichting, I.; Sligar, S. G. J. Inorg. Biochem. 2006, 100, 507-518
5. Groves, J. T. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 3569-3574
6. McLain, J. L.; Lee, J.; Groves, J. T. In Biomimetic Oxidations Catalyzed by Transition Metal Complexes; Meunier, B., Ed.; Imperial College Press: Cambridge, U.K., 2000; Chapter 3, pp 91-169.
7. Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314-320
8. Groves, J. T. J. Inorg. Biochem. 2006, 100, 434-447
9. Nam, W. Acc. Chem. Res. 2007, 40, 522-531
10. Goh, Y. M.; Nam, W. Inorg. Chem. 1999, 38, 914-920
11. Bell, S. R.; Groves, J. T. J. Am. Chem. Soc. 2009, 131, 9640-9641
12. Kang, Y.; Chen, H.; Jeong, Y. J.; Lai, W.; Bae, E. H.; Shaik, S.; Nam, W. Chem.-Eur. J. 2009, 15, 10039-10046
13. Hessenauer-Ilicheva, N.; Franke, A.; Wolak, M.; Higuchi, T.; van Eldik, R. Chem.-Eur. J. 2009, 15, 12447-12559
14. Hessenauer-Ilicheva, N.; Franke, A.; Meyer, D.; Woggon, W.-D.; van Eldik, R. Chem.-Eur. J. 2009, 15, 2941-2959
15. Parsell, T. H.; Yang, M. Y.; Borovik, A. S. J. Am. Chem. Soc. 2009, 131, 2762-2763
16. Yin, G. C.; Danby, A. M.; Kitko, D.; Carter, J. D.; Scheper, W. M.; Busch, D. H. J. Am. Chem. Soc. 2007, 129, 1512
17. Garcia-Bosch, I.; Company, A.; Cady, C. W.; Styring, S.; Browne, W. R.; Ribas, X.; Costas, M. Angew. Chem., Int. Ed. 2011, 50, 5648-5653
18. Kurahashi, T.; Kikuchi, A.; Shiro, Y.; Hada, M.; Fujii, H. Inorg. Chem. 2010, 49, 6664-6672
19. Jeong, Y. J.; Kang, Y.; Han, A. R.; Lee, Y. M.; Kotani, H.; Fukuzumi, S.; Nam, W. Angew. Chem., Int. Ed. 2008, 47, 7321-7324
20. Goldberg, D. P. Acc. Chem. Res. 2007, 40, 626-634
21. Kerber, W. D.; Goldberg, D. P. J. Inorg. Biochem. 2006, 100, 838-857
22. McGown, A. J.; Badiei, Y. M.; Leeladee, P.; Prokop, K. A.; DeBeer, S.; Goldberg, D. P. In Handbook of Porphyrin Science; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; World Scientific Press: Singapore, 2011; Vol. 14, pp 525-599.
23. McGown, A. J.; Kerber, W. D.; Fujii, H.; Goldberg, D. P. J. Am. Chem. Soc. 2009, 131, 8040-8048
24. Prokop, K. A.; de Visser, S. P.; Goldberg, D. P. Angew. Chem., Int. Ed. 2010, 49, 5091-5095
25. Lansky, D. E.; Goldberg, D. P. Inorg. Chem. 2006, 45, 5119-5125
26. Lansky, D. E.; Mandimustra, B.; Ramdhanie, B.; Clausén, M.; Penner-hahn, J.; Zvyagin, S. A.; Tesler, J.; Krzystek, J.; Zhan, R.; Ou, Z.; Kadish, K. M.; Zakharov, L.; Rheingold, A. L.; Goldberg, D. P. Inorg. Chem. 2005, 44, 4485-4498
27. Cho, K.; Kerber, W. D.; Lee, S. R.; Wan, A.; Batteas, J. D.; Goldberg, D. P. Inorg. Chem. 2010, 49, 8465-8473
28. Fukuzumi, S.; Kotani, H.; Prokop, K. A.; Goldberg, D. P. J. Am. Chem. Soc. 2011, 133, 1859-1869
29. Gross, Z. J. Biol. Inorg. Chem. 2001, 6, 733-738
30. Aviv, I.; Gross, Z. Chem. Commun. 2007, 1987-1999
31. Gryko, D. T.; Fox, J. P.; Goldberg, D. P. J. Porphyrins Phthalocyanines 2004, 8, 1091-1105
32. Paolesse, R. Synlett 2008, 15, 2215-2230
33. Guilard, R.; Barbe, J. M.; Stern, C.; Kadish, K. M. In The Porphyrin Handbook; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; Elsevier: San Diego, 2003; Vol. 18, pp 303-349.
34. Zdilla, M. J.; Dexheimer, J. L.; Abu-Omar, M. M. J. Am. Chem. Soc. 2007, 129, 11505-11511
35. Matsuo, T.; Hayashi, A.; Abe, M.; Matsuda, T.; Hisaeda, Y.; Hayashi, T. J. Am. Chem. Soc. 2009, 131, 15124-15125
36. Harischandra, D. N.; Zhang, R.; Newcomb, M. J. Am. Chem. Soc. 2005, 127, 13776-13777
37. Gross, Z.; Simkhovich, L.; Galili, N. Chem. Commun. 1999, 599-600
38. Golubkov, G.; Bendix, J.; Gray, H. B.; Mahammed, A.; Goldberg, I.; DiBilio, A. J.; Gross, Z. Angew. Chem., Int. Ed. 2001, 40, 2132-2134
39. Liu, H. Y.; Lai, T. S.; Yeung, L. L.; Chang, C. K. Org. Lett. 2003, 5, 617-620
40. Kumar, A.; Goldberg, I.; Botoshansky, M.; Buchman, Y.; Gross, Z. J. Am. Chem. Soc. 2010, 132, 15233-15245
41. Gross, Z.; Gray, H. B. Comments Inorg. Chem. 2006, 27, 61-72
42. Fukuzumi, S.; Tokuda, Y.; Kitano, T.; Okamoto, T.; Otera, J. J. Am. Chem. Soc. 1993, 115, 8960-8968
43. George, G. N. EXAFSPAK Software; Stanford Synchrotron Radiation Laboratory, Stanford Linear Accelerator Center, Stanford University: Stanford, CA, 2000.
44. Tenderholt, A. PySpline; Stanford Synchrotron Radiation Laboratory, Stanford Linear Accelerator Center, Stanford University: Stanford, CA, 2005.
45. Mustre de Leon, J.; Rehr, J. J.; Zabinsky, S. I.; Albers, R. C. Phys. Rev. B 1991, 44, 4146-4156
46. Rehr, J. J.; Mustre de Leon, J.; Zabinsky, S. I.; Albers, R. C. J. Am. Chem. Soc. 1991, 113, 5135-5140
47. Badejo, I. T.; Karaman, R.; Pinkerton, A. A.; Fry, J. L. J. Org. Chem. 1990, 55, 4327-4332
48. Stein, S. E.; Brown, R. L. J. Am. Chem. Soc. 1991, 113, 787-793
49. Bordwell, F. G.; Cheng, J. P.; Ji, G. Z.; Satish, A. V.; Zhang, Z. M. J. Am. Chem. Soc. 1991, 113, 9790-9795
50. Laarhoven, L. J. J.; Mulder, P.; Wayner, M. Acc. Chem. Res. 1999, 32, 342-349
51. Zhu, X. Q.; Li, H. R.; Li, Q.; Ai, T.; Lu, J. Y.; Yang, Y.; Cheng, J. P. Chem.-Eur. J. 2003, 9, 871-880
52. Lente, G.; Fabian, I.; Poe, A. J. New J. Chem. 2005, 29, 759-760
53. Stone, K. L.; Behan, R. K.; Green, M. T. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 16563-16565
54. Penner-Hahn, J. E.; Eble, K. S.; McMurry, T. J.; Renner, M.; Balch, A. L.; Groves, J. T.; Dawson, J. H.; Hodgson, K. O. J. Am. Chem. Soc. 1986, 108, 7819-7825
55. Wolter, T.; Meyer-Klaucke, W.; Muther, M.; Mandon, D.; Winkler, H.; Trautwein, A. X.; Weiss, R. J. Inorg. Biochem. 2000, 78, 117-122
56. III corrole, see: Hocking, R. K.; DeBeer George, S.; Gross, Z.; Walker, F. A.; Hodgson, K. O.; Hedman, B.; Solomon, E. I. Inorg. Chem. 2009, 48, 1678-1688
57. Rohde, J. U.; Torelli, S.; Shan, X. P.; Lim, M. H.; Klinker, E. J.; Kaizer, J.; Chen, K.; Nam, W.; Que, L., Jr. J. Am. Chem. Soc. 2004, 126, 16750-16761
58. Lim, M. H.; Rohde, J.-U.; Stubna, A.; Bukowski, M. R.; Costas, M.; Ho, R. Y. N.; Münck, E.; Nam, W.; Que, L., Jr. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 3665-3670
59. Klinker, E. J.; Kaizer, J.; Brennessel, W. W.; Woodrum, N. L.; Cramer, C. J.; Que, L., Jr. Angew. Chem., Int. Ed. 2005, 44, 3690-3694
60. Rohde, J.-U.; In, J.-H.; Lim, M. H.; Brennessel, W. W.; Bukowski, M. R.; Stubna, A.; Münck, E.; Nam, W.; Que, L., Jr. Science 2003, 199, 1037-1039
61. DeBeer George, S.; Brant, P.; Solomon, E. I. J. Am. Chem. Soc. 2005, 127, 667-674
62. Pan, Z. Z.; Horner, J. H.; Newcomb, M. J. Am. Chem. Soc. 2008, 130, 7776-7777
63. Bryant, J. R.; Mayer, J. M. J. Am. Chem. Soc. 2003, 125, 10351-10361
64. Mayer, J. M. Acc. Chem. Res. 1998, 31, 441-450
65. Wang, K.; Mayer, J. M. J. Am. Chem. Soc. 1997, 119, 1470-1471
66. Goldsmith, C. R.; Cole, A. P.; Stack, T. D. P. J. Am. Chem. Soc. 2005, 127, 9904-9912
67. Goldsmith, C. R.; Stack, T. D. P. Inorg. Chem. 2006, 45, 6048-6055
68. Li, F. F.; England, J.; Que, L., Jr. J. Am. Chem. Soc. 2010, 132, 2134-2135
69. 3+ where a rebound mechanism is not involved, see: Arunkumar, C.; Lee, Y. M.; Lee, J. Y.; Fukuzumi, S.; Nam, W. Chem.-Eur. J. 2009, 15, 11482-11489
70. Green, M. T. Curr. Opin. Chem. Biol. 2009, 13, 84-88
71. Sastri, C. V.; Lee, J.; Oh, K.; Lee, Y. J.; Lee, J.; Jackson, T. A.; Ray, K.; Hirao, H.; Shin, W.; Halfen, J. A.; Kim, J.; Que, L., Jr.; Shaik, S.; Nam, W. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 19181-19186
72. Bukowski, M. R.; Koehntop, K. D.; Stubna, A.; Bominaar, E. L.; Halfen, J. A.; Münck, E.; Nam, W.; Que, L., Jr. Science 2005, 310, 1000-1002
73. Saltsman, I.; Goldberg, I.; Gross, Z. J. Porphyrins Phthalocyanines 2010, 14, 615-620
74. Golubkov, G.; Gross, Z. J. Am. Chem. Soc. 2005, 127, 3258-3259