Mononuclear metal-O 2 complexes bearing macrocyclic N-tetramethylated cyclam ligands

Accounts of Chemical Research

Volumn 45, Issue 8, 2012, Pages 1321-1330

  Cho, Jaeheung ^a   Sarangi, Ritimukta ^b   Nam, Wonwoo ^a  

^a Ewha Womans University   (South Korea)

^b SLAC NATIONAL ACCELERATOR LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLAM; HETEROCYCLIC COMPOUND; LIGAND; MACROCYCLIC COMPOUND; ORGANOMETALLIC COMPOUND; OXYGEN;

CHEMISTRY; REVIEW; SYNTHESIS;

HETEROCYCLIC COMPOUNDS; LIGANDS; MACROCYCLIC COMPOUNDS; ORGANOMETALLIC COMPOUNDS; OXYGEN;

EID: 84865340571     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar3000019     Document Type: Article

References (47)

1. Nam, W. Dioxygen activation by metalloenzymes and models Acc. Chem. Res. 2007, 40, 465 and review articles in the special issue.
2. Bollinger, J. M., Jr.; Krebs, C. Enzymatic C-H activation by metal-superoxo intermediates Curr. Opin. Chem. Biol. 2007, 11, 151-158
3. 2+ dioxygenase superoxo, alkylperoxo, and bound product intermediates Science 2007, 316, 453-457
4. Karlsson, A.; Parales, J. V.; Parales, R. E.; Gibson, D. T.; Eklund, H.; Ramaswamy, S. Crystal structure of naphthalene dioxygenase: Side-on binding of dioxygen to iron Science 2003, 299, 1039-1042
5. Solomon, E. I.; Brunold, T. C.; Davis, M. I.; Kemsley, J. N.; Lee, S.-K.; Lehnert, N.; Neese, F.; Skulan, A. J.; Yang, Y.-S.; Zhou, J. Geometric and electronic structure/function correlations in non-heme iron enzymes Chem. Rev. 2000, 100, 235-349
6. Costas, M.; Mehn, M. P.; Jensen, M. P.; Que, L., Jr. Dioxygen activation at mononuclear nonheme iron active sites: Enzymes, models, and intermediates Chem. Rev. 2004, 104, 939-986
7. Mirica, L. M.; Ottenwaelder, X.; Stack, T. D. P. Structure and spectroscopy of copper-dioxygen complexes Chem. Rev. 2004, 104, 1013-1045
8. 2 complexes: Geometries, spectroscopic properties, electronic structures, and reactivity Acc. Chem. Res. 2007, 40, 601-608
9. Suzuki, M. Ligand effects on dioxygen activation by copper and nickel complexes: Reactivity and intermediates Acc. Chem. Res. 2007, 40, 609-617
10. Himes, R. A.; Karlin, K. D. Copper-dioxygen complex mediated C-H bond oxygenation: Relevance for particulate methane monooxygenase (pMMO) Curr. Opin. Chem. Biol. 2009, 13, 119-131
11. Yao, S.; Driess, M. Lessons from isolable nickel(I) precursor complexes for small molecule activation Acc. Chem. Res. 2012, 44, 276-287
12. 2 Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 3635-3640
13. Bakac, A. Kinetic and mechanistic studies of the reactions of transition metal-activated oxygen with inorganic substrates Coord. Chem. Rev. 2006, 250, 2046-2058
14. Wertz, D. L.; Valentine, J. S. Nucleophilicity of iron-peroxo porphyrin complexes Struct. Bonding (Berlin) 2000, 97, 37-60
15. Peterson, R. L.; Himes, R. A.; Kotani, H.; Suenobu, T.; Tian, L.; Siegler, M. A.; Solomon, E. I.; Fukuzumi, S.; Karlin, K. D. Cupric superoxo-mediated intermolecular C-H activation chemistry J. Am. Chem. Soc. 2011, 133, 1702-1705
16. Kunishita, A.; Kubo, M.; Sugimoto, H.; Ogura, T.; Sato, K.; Takui, T.; Itoh, S. Mononuclear copper(II)-superoxo complexes that mimic the structure and reactivity of the active center of PHM and D β M J. Am. Chem. Soc. 2009, 131, 2788-2789
17. Maiti, D.; Lee, D.-H.; Gaoutchenova, K.; Würtele, C.; Holthausen, M. C.; Narducci Sarjeant, A. A.; Sundermeyer, J.; Schindler, S.; Karlin, K. D. Reactions of a copper(II) superoxo complex lead to C-H and O-H substrate oxygenation: Modeling copper-monooxygenase C-H hydroxylation Angew. Chem., Int. Ed. 2008, 47, 82-85
18. Lee, Y.-M.; Hong, S.; Morimoto, Y.; Shin, W.; Fukuzumi, S.; Nam, W. Dioxygen activation by a nonheme iron(II) complex: Formation of an iron(IV)-oxo complex via C-H activation by a putative iron(III)-superoxo species J. Am. Chem. Soc. 2010, 132, 10668-10670
19. Wu, A. J.; Penner-Hahn, J. E.; Pecoraro, V. L. Structural, spectroscopic, and reactivity models for the manganese catalases Chem. Rev. 2004, 104, 903-938
20. VanAtta, R. B.; Strouse, C. E.; Hanson, L. K.; Valentine, J. S. Peroxo(tetraphenylporphinato)manganese(III) and chloro(tetraphenylporphinato) manganese(II) anions. Syntheses, crystal structures, and electronic structures J. Am. Chem. Soc. 1987, 109, 1425-1434
21. 3 J. Am. Chem. Soc. 1994, 116, 11596-11597
22. RCo-dioxygen complexes Coord. Chem. Rev. 2000, 198, 61-87
23. Dickman, M. H.; Pope., M. T. Peroxo and superoxo complexes of chromium, molybdenum, and tungsten Chem. Rev. 1994, 94, 569-584
24. Tiné, M. R. Cobalt complexes in aqueous solutions as dioxygen carriers Coord. Chem. Rev. 2012, 256, 316-327
25. 2 for the specific oxidation of organic substrates with cobalt(II) catalysts Coord. Chem. Rev. 1987, 79, 321-332
26. Barefield, E. K. Coordination chemistry of N-tetraalkylated cyclam ligands-A status report Coord. Chem. Rev. 2010, 254, 1607-1627
27. Cho, J.; Woo, J.; Nam, W. An "end-on" chromium(III)-superoxo complex: Crystallographic and spectroscopic characterization and reactivity in C-H bond activation of hydrocarbons J. Am. Chem. Soc. 2010, 132, 5958-5959
28. +: A side-on peroxido manganese(III) complex bearing a non-heme ligand Angew. Chem., Int. Ed. 2007, 46, 377-380
29. Annaraj, J.; Cho, J.; Lee, Y.-M.; Kim, S. Y.; Latifi, R.; de Visser, S. P.; Nam, W. Structural characterization and remarkable axial ligand effect on the nucleophilic reactivity of a nonheme manganese(III)-peroxo complex Angew. Chem., Int. Ed. 2009, 48, 4150-4153
30. Annaraj, J.; Suh, Y.; Seo, M. S.; Kim, S. O.; Nam, W. Mononuclear nonheme ferric-peroxo complex in aldehyde deformylation Chem. Commun. 2005, 4529-4531
31. Cho, J.; Jeon, S.; Wilson, S. A.; Liu, L. V.; Kang., E. A.; Braymer, J. J.; Lim, M. H.; Hedman, B.; Hodgson, K. O.; Valentine, J. S.; Solomon, E. I.; Nam, W. Structure and reactivity of a mononuclear non-haem iron(III)-peroxo complex Nature 2011, 478, 502-505
32. Jo, Y.; Annaraj, J.; Seo, M. S.; Lee, Y.-M.; Kim, S. Y.; Cho, J.; Nam, W. Reactivity of a cobalt(III)-peroxo complex in oxidative nucleophilic reactions J. Inorg. Biochem. 2008, 102, 2155-2159
33. Cho, J.; Sarangi, R.; Kang, H. Y.; Lee, J. Y.; Kubo, M.; Ogura, T.; Solomon, E. I.; Nam, W. Synthesis, structural and spectroscopic characterization, and reactivities of mononuclear cobalt(III)-peroxo complexes J. Am. Chem. Soc. 2010, 132, 16977-16986
34. + J. Am. Chem. Soc. 2006, 128, 14230-14231
35. Cho, J.; Sarangi, R.; Annaraj, J.; Kim, S. Y.; Kubo, M.; Ogura, T.; Solomon, E. I.; Nam, W. Geometric and electronic structure and reactivity of a mononuclear "side-on" nickel(III)-peroxo complex Nat. Chem. 2009, 1, 568-572
36. 2 systems Inorg. Chem. 2011, 50, 614-620
37. Kieber-Emmons, M. T.; Riordan, C. G. Dioxygen activation at monovalent nickel Acc. Chem. Res. 2007, 40, 618-625
38. Rohde, J.-U.; In, J.-H.; Lim, M. H.; Brennessel, W. W.; Bukowski, M. R.; Stubna, A.; Münck, E.; Nam, W.; Que, L., Jr. Crystallographic and spectroscopic characterization of a nonheme Fe(IV)=O complex Science 2003, 229, 1037-1039
39. Fukuzumi, S.; Morimoto, Y.; Kotani, H.; Naumov, P.; Lee, Y.-M.; Nam, W. Crystal structure of a metal ion-bound oxoiron(IV) complex and implications for biological electron transfer Nat. Chem. 2010, 2, 756-759
40. Cho, J.; Woo, J.; Han, J. E.; Kubo, M.; Ogura, T.; Nam, W. Chromium(V)-oxo and chromium(III)-superoxo complexes bearing a macrocyclic TMC ligand in hydrogen atom abstraction reactions Chem. Sci. 2011, 2, 2057-2062
41. Qin, K.; Incarvito, C. D.; Rheingold, A. L.; Theopold, K. H. A structurally characterized chromium(III) superoxide complex features "side-on" bonding Angew. Chem., Int. Ed. 2002, 41, 2333-2335
42. IV=O complex J. Am. Chem. Soc. 2011, 133, 7256-7259
43. 2NiL] Angew. Chem., Int. Ed. 2008, 47, 7110-7113
44. MacBeth, C. E.; Gupta, R.; Mitchell-Koch, K. R.; Young, V. G., Jr.; Lushington, G. H.; Thompson, W. H.; Hendrich, M. P.; Borovik, A. S. Utilization of hydrogen bonds to stabilize M-O(H) units: Synthesis and properties of monomeric iron and manganese complexes with terminal oxo and hydroxo ligands J. Am. Chem. Soc. 2004, 126, 2556-2567
45. 2) complex: Reactivity patterns for C-H activation, aromatic hydroxylation and heteroatom oxidation Chem. Commun. 2011, 47, 10674-10676
46. n+ (M = Ni(III) or Pd(II)) cores Chem. Commun. 2004, 1716-1717
47. Nam, W. High-valent iron(IV)-oxo complexes of heme and non-heme ligands in oxygenation reactions Acc. Chem. Res. 2007, 40, 522-531