Remarkable solvent, porphyrin ligand, and substrate effects on participation of multiple active oxidants in manganese(III) porphyrin catalyzed oxidation reactions

Chemistry - A European Journal

Volumn 19, Issue 5, 2013, Pages 1810-1818

  Hyun, Min Young ^a   Jo, Young Dan ^a   Lee, Jun Ho ^b   Lee, Hong Gyu ^a   Park, Hyun Min ^a   Hwang, In Hong ^a   Kim, Kyeong Beom ^a   Lee, Suk Joong ^b   Kim, Cheal ^a  

^a Seoul National University of Science and Technology   (South Korea)

^b Korea University   (South Korea)

Author keywords

manganese; oxidation; oxido ligands; porphyrinoids; solvent effects

Indexed keywords

1-OCTENE; ACTIVE SPECIES; APROTIC SOLVENTS; CATALYTIC REACTIONS; CATALYZED OXIDATION; CYCLOHEXENES; ELECTRON-DONATING SUBSTITUENTS; ELECTRON-WITHDRAWING SUBSTITUENTS; ELECTRONWITHDRAWING; HETEROLYTIC CLEAVAGE; HOMOLYSIS; MANGANESEPORPHYRINS; MECHANISTIC PROBES; OLEFIN EPOXIDATION; PORPHYRINOIDS; PROTIC SOLVENTS; REACTIVE SPECIES; SOLVENT EFFECTS; SOLVENT SYSTEM; SUBSTRATE CONCENTRATIONS; SUBSTRATE EFFECTS;

CATALYSIS; CATALYTIC OXIDATION; CHLORINE COMPOUNDS; EPOXIDATION; ETHYLBENZENE; LIGANDS; MANGANESE; MANGANESE OXIDE; OLEFINS; ORGANIC SOLVENTS; OXIDANTS; OXIDATION; PORPHYRINS; REACTION INTERMEDIATES; REACTION KINETICS; SOLVENTS; THERMOMECHANICAL PULPING PROCESS; TOLUENE;

SUBSTRATES;

ALKENE; CYCLOHEXENE DERIVATIVE; LIGAND; MANGANESE(III) PORPHYRIN; METALLOPORPHYRIN; OXIDIZING AGENT; PORPHYRIN; SOLVENT;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; OXIDATION REDUCTION REACTION;

ALKENES; CATALYSIS; CYCLOHEXENES; KINETICS; LIGANDS; METALLOPORPHYRINS; MOLECULAR STRUCTURE; ORGANIC CHEMISTRY PROCESSES; OXIDANTS; OXIDATION-REDUCTION; PORPHYRINS; SOLVENTS;

EID: 84872698630     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201202640     Document Type: Article

References (89)

1. B. Meunier, Chem. Rev. 1992, 92, 1411-1456
2. I. G. Denisov, T. M. Makris, S. G. Sligar, I. Schlichting, Chem. Rev. 2005, 105, 2253-2277
3. P. R. Ortiz de Montellano, Ed. Cytochrome P450 Structure, Mechanism, and Biochemistry 3 rd ed.; Kluwer Academic/Plenum: New York, 2005
4. P. R. Ortiz de Montellano, Chem. Rev. 2010, 110, 932-948
5. J. T. Groves, J. Inorg. Biochem. 2006, 100, 434-447
6. M. Costas, Coord. Chem. Rev. 2011, 255, 2912-2932
7. W. Liu, J. T. Groves, J. Am. Chem. Soc. 2010, 132, 12847-12849
8. S. H. Kim, H. Park, M. S. Seo, M. Kubo, T. Ogura, J. Klajn, D. T. Gryko, J. S. Valentine, W. Nam, J. Am. Chem. Soc. 2010, 132, 14030-14032
9. J. Annaraj, J. Cho, Y.-M. Lee, S. Y. Kim, R. Latifi, S. P. de Visser, W. Nam, Angew. Chem. 2009, 121, 4214-4217
10. Angew. Chem. Int. Ed. 2009, 48, 4150-4153
11. T. P. Umile, J. T. Groves, Angew. Chem. 2011, 123, 721-724
12. Angew. Chem. Int. Ed. 2011, 50, 695-698
13. M. Costas, M. P. Mehn, M. P. Jensen, L. Que, Jr., Chem. Rev. 2004, 104, 939-986
14. E. Y. Tshuva, S. J. Lippard, Chem. Rev. 2004, 104, 987-1012
15. S. V. Kryatov, E. V. Rybak-Akimova, Chem. Rev. 2005, 105, 2175-2226
16. M. Newcomb, R. Zhang, R. E. P. Chandrasena, J. A. Halgrimson, J. H. Horner, T. M. Makris, S. G. Sligar, J. Am. Chem. Soc. 2006, 128, 4580-4581
17. W. Nam, Acc. Chem. Res. 2007, 40, 522-531
18. D. Dolphin, T. G. Traylor, L. Y. Xie, Acc. Chem. Res. 1997, 30, 251-259
19. C. Kim, Y. Watanabe, in Encyclopedia of Catalysis 2002, Wiley, New York, pp. 593-643
20. R. Zhang, M. Newcomb, Acc. Chem. Res. 2008, 41, 468-477
21. P. H. Toy, M. Newcomb, M. J. Coon, A. D. N. Vaz, J. Am. Chem. Soc. 1998, 120, 9178-9179
22. S. Shaik, W. Lai, H. Chen, Y. Wang, Acc. Chem. Res. 2010, 43, 1154-1165
23. A. S. Borovik, Chem. Soc. Rev. 2011, 40, 1870-1874.
24. J. P. Collman, J. I. Brauman, B. Meunier, T. Hayashi, T. Kodadek, S. A. Raybuck, J. Am. Chem. Soc. 1985, 107, 2000-2005
25. B. Meunier, E. Guilmet, M.-E. De Carval, R. Poilblanc, J. Am. Chem. Soc. 1984, 106, 6668-6676
26. J. A. Smegal, B. C. Schardt, C. L. Hill, J. Am. Chem. Soc. 1983, 105, 3510-3515
27. L.-C. Yuan, T. C. Bruice, J. Am. Chem. Soc. 1986, 108, 1643-1650
28. E. Porhiel, A. Bondon, J. Leroy, Eur. J. Inorg. Chem. 2000, 1097-1105
29. E. Baciocchi, T. Boschi, L. Cassioli, C. Galli, L. Jaquinod, A. Lapi, R. Paolesse, K. M. Smith, P. Tagliatesta, Eur. J. Org. Chem. 1999, 3281-3286
30. J. P. Collman, T. Kodadek, J. I. Brauman, J. Am. Chem. Soc. 1986, 108, 2588-2594
31. P. Battioni, J. P. Renaud, J. F. Bartoli, M. Reina-Artiles, M. Fort, D. Mansuy, J. Am. Chem. Soc. 1988, 110, 8462-8470.
32. J. T. Groves, J. Lee, S. S. Marla, J. Am. Chem. Soc. 1997, 119, 6269-6273
33. W. Nam, I. Kim, M. H. Lim, H. J. Choi, J. S. Lee, H. G. Jang, Chem. Eur. J. 2002, 8, 2067-2071
34. W. J. Song, M. S. Seo, S. D. George, T. Ohta, R. Song, M.-J. Kang, T. Tosha, T. Kitagawa, E. I. Solomon, W. Nam, J. Am. Chem. Soc. 2007, 129, 1268-1277
35. N. Jin, M. Ibrahim, T. G. Spiro, J. T. Groves, J. Am. Chem. Soc. 2007, 129, 12416-12417
36. Z. Gross, Angew. Chem. 2008, 120, 2777-2779
37. Angew. Chem. Int. Ed. 2008, 47, 2737-2739
38. J. T. Groves, M. K. Stern, J. Am. Chem. Soc. 1988, 110, 8628-8638
39. M. E. Crestoni, S. Fornarini, F. Lanucara, Chem. Eur. J. 2009, 15, 7863-7866
40. J. Y. Lee, Y.-M. Lee, H. Kotani, W. Nam, S. Fukuzumi, Chem. Commun. 2009, 704-706.
41. R. Zhang, J. H. Horner, M. Newcomb, J. Am. Chem. Soc. 2005, 127, 6573-6582
42. C. Arunkumar, Y.-M. Lee, J. Y. Lee, S. Fukuzumi, W. Nam, Chem. Eur. J. 2009, 15, 11482-11489
43. R. Latifi, L. Tahsini, B. Karamzadeh, N. Safari, W. Nam, S. P. de Visser, Arch. Biochem. Biophys. 2011, 507, 4-13
44. J. Bernadou, A.-S. Eabiano, A. Robert, B. Meunier, J. Am. Chem. Soc. 1994, 116, 9375-9376
45. R. Zhang, M. Newcomb, J. Am. Chem. Soc. 2003, 125, 12418-12419.
46. S.-E. Park, W. J. Song, Y. O. Ryu, M. H. Lim, R. Song, K. M. Kim, W. Nam, J. Inorg. Biochem. 2005, 99, 424-431
47. J. T. Groves, Y. Watanabe, T. J. McMurry, J. Am. Chem. Soc. 1983, 105, 4489-4490.
48. S. H. Lee, L. Xu, B. K. Park, Y. V. Mironov, S. H. Kim, Y. J. Song, C. Kim, Y. Kim, S. J. Kim, Chem. Eur. J. 2010, 16, 4678-4685
49. Y. J. Song, S. H. Lee, H. M. Park, S. H. Kim, H. G. Goo, G. H. Eom, J. H. Lee, M. S. Lah, Y. Kim, S.-J. Kim, J. E. Lee, H.-I. Lee, C. Kim, Chem. Eur. J. 2011, 17, 7336-7344.
50. S. H. Lee, J. H. Han, H. Kwak, S. J. Lee, E. Y. Lee, H. J. Kim, J. H. Lee, C. Bae, S. N. Lee, Y. Kim, C. Kim, Chem. Eur. J. 2007, 13, 9393-9398
51. Y. J. Song, M. Y. Hyun, J. H. Lee, H. G. Lee, J. H. Kim, S. P. Jang, J. Y. Noh, Y. Kim, S.-J. Kim, S. J. Lee, C. Kim, Chem. Eur. J. 2012, 18, 6094-6101
52. M. Y. Hyun, S. H. Kim, Y. J. Song, H. G. Lee, Y. D. Jo, J. H. Kim, I. H. Hwang, J. Y. Noh, J. Kang, C. Kim, J. Org. Chem. 2012, 77, 7307-7312.
53. N. Suzuki, T. Higuchi, T. Nagano, J. Am. Chem. Soc. 2002, 124, 9622-9628.
54. 3CN (1:4).
55. 2 was reported by Groves and Watanabe:, J. T. Groves, Y. Watanabe, Inorg. Chem. 1986, 25, 4808-4810.
56. W. Nam, H. J. Han, S.-Y. Oh, Y. J. Lee, M.-H. Choi, S.-Y. Han, C. Kim, S. K. Woo, W. Shin, J. Am. Chem. Soc. 2000, 122, 8677-8684
57. J. T. Groves, Y. Watanabe, J. Am. Chem. Soc. 1986, 108, 7834-7836
58. J. T. Groves, Y. Watanabe, J. Am. Chem. Soc. 1986, 108, 7836-7837
59. I. V. Khavrutskii, D. G. Musaev, K. Morokuma, Inorg. Chem. 2005, 44, 306-315
60. T. G. Traylor, S. Tsuchiya, Y. S. Byun, C. Kim, J. Am. Chem. Soc. 1993, 115, 2775-2781
61. L. C. Yuan, T. C. Bruice, Inorg. Chem. 1985, 24, 986-987
62. T. G. Traylor, J. P. Ciccone, J. Am. Chem. Soc. 1989, 111, 8413-8420
63. N. Jin, D. E. Lahaye, J. T. Groves, Inorg. Chem. 2010, 49, 11516-11524.
64. A. Franke, C. Fertinger, R. van Eldik, Angew. Chem. 2008, 120, 5316-5320
65. Angew. Chem. Int. Ed. 2008, 47, 5238-5242
66. W. Nam, R. Ho, J. S. Valentine, J. Am. Chem. Soc. 1991, 113, 7052-7054
67. K. Machii, Y. Watanabe, I. Morishima, J. Am. Chem. Soc. 1995, 117, 6691-6697
68. Y. Watanabe, K. Yamaguchi, I. Morishima, K. Takehiro, M. Shimizu, T. Hayakawa, H. Orita, Inorg. Chem. 1991, 30, 2581-2582
69. W. Adam, K. J. Roschmann, C. R. Saha-Moller, D. Seebach, J. Am. Chem. Soc. 2002, 124, 5068-5073
70. J. P. Collman, L. Zeng, J. I. Brauman, Inorg. Chem. 2004, 43, 2672-2679
71. K. P. Bryliakov, D. E. Babushkin, E. P. Talsi, J. Mol. Catal. A J. Mol. Catal. A: Chem. 2000, 158, 19-35
72. A. Mahammed, Z. Gross, J. Am. Chem. Soc. 2005, 127, 2883-2887
73. R. V. Ottenbacher, K. P. Bryliakov, E. P. Talsi, Inorg. Chem. 2010, 49, 8620-8628
74. A. Kumar, I. Goldberg, M. Botoshansky, Y. Buchman, Z. Gross, J. Am. Chem. Soc. 2010, 132, 15233-15245
75. I. Garcia-Bosch, A. Company, X. Fontrodona, X. Ribas, M. Costas, Org. Lett. 2008, 10, 2095-2098
76. M. Newcomb, P. H. Toy, Acc. Chem. Res. 2000, 33, 449-455
77. T. Tano, M. Z. Ertem, S. Yamaguchi, A. Kunishita, H. Sugimoto, N. Fujieda, T. Ogura, C. J. Cramer, S. Itoh, Dalton Trans. 2011, 40, 10326.
78. B. R. Cook, T. J. Reinert, K. S. Suslick, J. Am. Chem. Soc. 1986, 108, 7281-7286.
79. J. P. Collman, L. Zeng, R. A. Decréau, Chem. Commun. 2003, 2974-2975.
80. W. Nam, M. H. Lim, H. J. Lee, C. Kim, J. Am. Chem. Soc. 2000, 122, 6641-6647
81. J. P. Collman, L. Zeng, H. J. H. Wang, A. Lei, J. I. Brauman, Eur. J. Org. Chem. 2006, 2707-2714.
82. - species were not formed in these solvent systems.
83. J. H. Dawson, Science 1988, 240, 433-439
84. M. Sono, M. P. Roach, E. D. Coulter, J. H. Dawson, Chem. Rev. 1996, 96, 2841-2887
85. I. Schlichting, J. Berendzen, K. Chu, A. M. Stock, S. A. Maves, D. E. Benson, R. M. Sweet, D. Ringe, G. A. Petsko, S. G. Sligar, Science 2000, 287, 1615-1622.
86. J. S. Lindsey, R. W. Wagner, J. Org. Chem. 1989, 54, 828-836
87. L. Kaustov, M. E. Tal, A. I. Shames, Z. Gross, Inorg. Chem. 1997, 36, 3503-3511
88. H. C. Sacco, Y. Iamamoto, J. R. Lindsay Smith, J. Chem. Soc. Perkin Trans. 2 2001, 2, 181-190
89. H. Tamiaki, N. Matsumoto, S. Unno, S. Shinoda, H. Tsukube, Inorg. Chim. Acta 2000, 302, 243-249.