[CuO]+ and [CuOH]2+ Complexes: Intermediates in Oxidation Catalysis?

Accounts of Chemical Research

Volumn 48, Issue 7, 2015, Pages 2126-2131

  Gagnon, Nicole ^a   Tolman, William B ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; COPPER; COPPER HYDROXIDE; CUPRIC OXIDE; HYDROXIDE; LIGAND; ORGANOMETALLIC COMPOUND; PYRIDINE DERIVATIVE;

CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION;

AMIDES; CATALYSIS; COPPER; HYDROXIDES; LIGANDS; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; PYRIDINES;

EID: 84937468972     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/acs.accounts.5b00169     Document Type: Article

References (55)

1. Solomon, E. I.; Heppner, D. E.; Johnston, E. M.; Ginsbach, J. W.; Cirera, J.; Qayyum, M.; Kieber-Emmons, M. T.; Kjaergaard, C. H.; Hadt, R. G.; Tian, L. Copper Active Sites in Biology Chem. Rev. 2014, 114, 3659-3853
2. Ryland, B. L.; Stahl, S. S. Practical Aerobic Oxidations of Alcohols and Amines with Homogeneous Copper/TEMPO and Related Catalyst Systems Angew. Chem., Int. Ed. 2014, 53, 8824-8838
3. Wendlandt, A. E.; Suess, A. M.; Stahl, S. S. Copper-Catalyzed Aerobic Oxidative C-H Functionalizations: Trends and Mechanistic Insights Angew. Chem., Int. Ed. 2011, 50, 11062-11087
4. Díaz-Requejo, M. M.; Pérez, P. J. Coinage Metal Catalyzed C-H Bond Functionalization of Hydrocarbons Chem. Rev. 2008, 108, 3379-3394
5. Mirica, L. M.; Ottenwaelder, X.; Stack, T. D. P. Sructure and Spectroscopy of Copper-Dioxygen Complexes Chem. Rev. 2004, 104, 1013-1045
6. Lewis, E. A.; Tolman, W. B. Reactivity of Copper-Dioxygen Systems Chem. Rev. 2004, 104, 1047-1076
7. 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
8. 2O by the Multicopper Oxidases Dalton Trans. 2008, 3921-3932
9. 2 Complexes: Geometries, Spectroscopic Properties, Electronic Structures, and Reactivity Acc. Chem. Res. 2007, 40, 601-608
10. Ginsbach, J. W.; Peterson, R. L.; Cowley, R. E.; Karlin, K. D.; Solomon, E. I. Correlation of the Electronic and Geometric Structures in Mononuclear Copper(II) Superoxide Complexes Inorg. Chem. 2013, 52, 12872-12874
11. II-Superoxo with Enhanced Reactivity J. Am. Chem. Soc. 2015, 137, 2796-2799 and references therein
12. Klinman, J. P. Mechanisms Whereby Mononuclear Copper Proteins Functionalize Organic Substrates Chem. Rev. 1996, 96, 2541-2561
13. 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
14. Balasubramanian, R.; Rosenzweig, A. Structural and Mechanistic Insights into Methane Oxidation by Particulate Methane Monooxygenase Acc. Chem. Res. 2007, 40, 573-580
15. Sono, M.; Roach, M. P.; Dawson, J. H. Heme-Containing Oxygenases Chem. Rev. 1996, 96, 2841-2887
16. Abu-Omar, M. M.; Loaiza, A.; Hontzeas, N. Reaction Mechanisms of Mononuclear Non-Heme Iron Oxygenases Chem. Rev. 2005, 105, 2227-2252
17. 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
18. Krebs, C.; Galoníc, D. F.; Fujimori, D.; Walsh, C.; Bollinger, J. Non-Heme Fe(IV)-Oxo Intermediates Acc. Chem. Res. 2007, 40, 484-492
19. McDonald, A. R.; Que, L., Jr. High-valent nonheme iron-oxo complexes: Synthesis, structure, and spectroscopy Coord. Chem. Rev. 2013, 257, 414-428
20. Reinaud, O.; Capdevielle, P.; Maumy, M. Copper(II) mediated aromatic hydroxylation by trimethylamine N-oxide J. Chem. Soc., Chem. Commun. 1990, 566-568
21. Blain, I.; Giorgi, M.; Riggi, I. D.; Réglier, M. Substrate-Binding Ligand Approach in Chemical Modeling of Copper-Containing Monooxygenases, 1. Intramolecular Stereoselective Oxygen Atom Insertion into a Non-Activated C-H Bond Eur. J. Inorg. Chem. 2000, 393-398
22. Kunishita, A.; Ishimaru, H.; Nakashima, S.; Ogura, T.; Itoh, S. Reactivity of Mononuclear Alkylperoxo Copper(II) Complex. O-O Bond Cleavage and C-H Bond Activation J. Am. Chem. Soc. 2008, 130, 4244-4245
23. Maiti, D.; Lee, D.-H.; Gaoutchenova, K.; Würtele, C.; Holthausen, M. C.; Sarjeant, A. A. N.; 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
24. Maiti, D.; Narducci Sarjeant, A. A.; Karlin, K. D. Copper-Hydroperoxo-Mediated N-Debenzylation Chemistry Mimicking Aspects of Copper Monooxygenases Inorg. Chem. 2008, 47, 8736-8747
25. + and Its Role in the Spin-Selective Hydrogen- and Oxygen-Atom Transfers in the Thermal Activation of Methane Angew. Chem., Int. Ed. 2011, 50, 4966-4969
26. + J. Phys. Chem. B 2004, 108, 14407-14416
27. Yoshizawa, K.; Kihara, N.; Kamachi, T.; Shiota, Y. Catalytic Mechanism of Dopamine β-Monooxygenase Mediated by Cu(III)-Oxo Inorg. Chem. 2006, 45, 3034-3041
28. Decker, A.; Solomon, E. I. Dioxygen Activation by Copper, Heme and Non-Heme Iron Enzymes: Comparison of Electronic Structures and Reactivities Curr. Opin. Chem. Biol. 2005, 9, 152-163
29. Crespo, A.; Marti, M. A.; Roitberg, A. E.; Amzel, L. M.; Estrin, D. A. The Catalytic Mechanism of Peptidylglycine α-Hydroxylating Monooxygenase Investigated by Computer Simulation J. Am. Chem. Soc. 2006, 128, 12817-12828
30. Kim, S.; Ståhlberg, J.; Sandgren, M. Quantum Mechanical Calculations Suggest That Lytic Polysaccharide Monooxygenases Use a Copper-Oxyl, Oxygen-Rebound Mechanism Proc. Natl. Acad. Sci. U.S.A. 2014, 111, 149-154
31. Gupta, A.; Tolman, W. B. Copper/α-Ketocarboxylate Chemistry With Supporting Peralkylated Diamines: Reactivity of Copper(I) Complexes and Dicopper-Oxygen Intermediates Inorg. Chem. 2010, 49, 3531-3539
32. 2+ Core: Structural Implications J. Am. Chem. Soc. 1999, 121, 5583-5584
33. Mahadevan, V.; Henson, M. J.; Solomon, E. I.; Stack, T. D. P. Differential Reactivity between Interconvertible Side-On Peroxo and Bis-μ-oxodicopper Isomers Using Peralkylated Diamine Ligands J. Am. Chem. Soc. 2000, 122, 10249-10250
34. 2 Reactions That Yield Copper-Oxygen Intermediates Capable of Hydroxylating Arenes J. Am. Chem. Soc. 2007, 129, 14190-14192
35. 2: In Silico Studies on Ligand Effects and C-H-Activation Reactivity Chem.-Eur. J. 2009, 15, 4886-4895
36. Comba, P.; Knoppe, S.; Martin, B.; Rajaraman, G.; Rolli, C.; Shapiro, B.; Stork, T. Copper(II)-Mediated Aromatic ortho -Hydroxylation: A Hybrid DFT and Ab Initio Exploration Chem.-Eur. J. 2008, 14, 344-357
37. Hong, S.; Gupta, A. K.; Tolman, W. B. Intermediates in Reactions of Copper(I) Complexes with N-Oxides: From the Formation of Stable Adducts to Oxo Transfer Inorg. Chem. 2009, 48, 6323-6325
38. 2 Reactivity: Unique Copper-Superoxo and Bis(μ-oxo) Complexes J. Am. Chem. Soc. 2002, 124, 2108-2809
39. Levason, W.; M.D. Spicer, M. D. The Chemistry of Copper and Silver in Their Higher Oxidation States Coord. Chem. Rev. 1987, 76, 45-120
40. Anson, F. C.; Collins, T. J.; Richmond, T. G.; Santarsiero, B. D.; Toth, J. E.; Treco, B. G. R. T. Highly Stabilized Copper(III) Complexes J. Am. Chem. Soc. 1987, 109, 2974-2979
41. II Bridged Site J. Am. Chem. Soc. 2010, 132, 4693-4701
42. Donoghue, P. J.; Tehranchi, J.; Cramer, C. J.; Sarangi, R.; Solomon, E. I.; Tolman, W. B. Rapid C-H Bond Activation by a Monocopper(III)-Hydroxide Complex J. Am. Chem. Soc. 2011, 133, 17602-17605
43. II-Cyanomethides Eur. J. Inorg. Chem. 2013, 2013, 4077-4084
44. IV=O complexes towards C-H bond Cleavage Inorg. Chem. 2013, 52, 3976-3984
45. Kundu, S.; Van Kirk Thompson, J.; Shen, L. Q.; Mills, M. R.; Brominaar, E. L.; Ryabov, A. D.; Collins, T. J. Activation Parameters as Mechanistic Probes in the TAML Iron(V)-Oxo Oxidations of Hydrocarbons Chem.-Eur. J. 2015, 21, 1803-1810
46. Warren, J. J.; Tronic, T. A.; Mayer, J. M. Thermochemistry of Proton-Coupled Electron Transfer Reagents and its Implications Chem. Rev. 2010, 110, 6961-7001
47. Dhar, D.; Tolman, W. B. Hydrogen Atom Abstraction from Hydrocarbons by a Copper(III)-Hydroxide Complex J. Am. Chem. Soc. 2015, 137, 1322-1329
48. Barrón, D.; Barbosa, J. Acid-Base Behaviour of Substituted Phenolic Substances and Resolution of Acid Strength in Tetrahydrofuran Analyt. Chim. Acta 2000, 403, 339-347
49. Yosca, T. H.; Rittle, J.; Krest, C. M.; Onderko, E. L.; Silakov, A.; Calixto, J. C.; Behan, R. K.; Green, M. T. Iron(IV)hydroxide pKa and the Role of Thiolate Ligation in C-H Bond Activation by Cytochrome P450 Science 2013, 342, 825-829
50. Wang, X.; Ullrich, R.; Hofrichter, M.; Groves, J. T. Heme-Thiolate Ferryl of Aromatic Peroxygenase Is Basic and Reactive Proc. Natl. Acad. Sci. U.S.A. 2015, 112, 3686-3691
51. Prokop, K. A.; de Visser, S. P.; Goldberg, D. P. Unprecedented Rate Enhancements of Hydrogen-Atom Transfer to a Manganese(V)-Oxo Corrolazine Complex Angew. Chem., Int. Ed. 2010, 49, 5091-5095
52. Borovik, A. S. Role of Metal-Oxo Complexes in the Cleavage of C-H Bonds Chem. Soc. Rev. 2011, 40, 1870-1874
53. Borovik, A. Bioinspired Hydrogen Bond Motifs in Ligand Design: The Role of Noncovalent Interactions in Metal Ion Mediated Activation of Dioxygen Acc. Chem. Res. 2005, 38, 54-61
54. Litwinienko, G.; Ingold, K. U. Solvent Effects on the Rates and Mechanisms of Reaction of Phenols with Free Radicals Acc. Chem. Res. 2007, 40, 222-230
55. Usharani, D.; Lacy, D. C.; Borovik, A. S.; Shaik, S. Dichotomous Hydrogen Atom Transfer vs Proton-Coupled Electron Transfer during Activation of X-H Bonds (X = C, N, O) by Nonheme Iron-Oxo Complexes of Variable Basicity J. Am. Chem. Soc. 2013, 135, 17090-17104