Enhanced catalytic efficiency in the epoxidation of alkenes for manganese complex encapsulated in the hydrophobic interlayer region of layered double hydroxides

Industrial and Engineering Chemistry Research

Volumn 52, Issue 50, 2013, Pages 17821-17828

  Liu, Yuqing ^a   An, Zhe ^a   Zhao, Liwei ^a   Liu, Hui ^a   He, Jing ^a  

^a BEIJING UNIVERSITY OF CHEMICAL TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC EFFICIENCIES; ENZYMATIC CATALYSIS; EPOXIDATION OF ALKENES; HYDROPHOBIC ENVIRONMENT; HYDROPHOBIC REGIONS; INTERLAYER REGIONS; LAYERED DOUBLE HYDROXIDES; MANGANESE COMPLEXES;

CATALYSIS; CATALYST ACTIVITY; HYDROCARBONS; MANGANESE; PHOSPHOLIPIDS; STYRENE;

HYDROPHOBICITY;

EID: 84890689615     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie4026693     Document Type: Article

References (44)

1. Bedioui, F. Zeolite-encapsulated and Clay-intercalated Metal Porphyrin, Phthalocyanine and Schiff-base Complexes as Models for Biomimetic Oxidation Catalysts: An Overview Coord. Chem. Rev. 1995, 144, 39
2. Connon, S. J.; Blechert, S. Recent Advances in Alkene Metathesis; Topics in Organometallic Chemistry; Springer: New York, 2004; Vol. 11, p 93.
3. Over, H. Surface Chemistry of Ruthenium Dioxide in Heterogeneous Catalysis and Electrocatalysis: From Fundamental to Applied Research Chem. Rev. 2012, 112, 3356
4. Sweigert, P.; Xu, Z.; Hong, Y.; Swavey, S. Nickel, Copper, and Zinc Centered Ruthenium-substituted Porphyrins: Effect of Transition Metals on Photoinduced DNA Cleavage and Photoinduced Melanoma Cell Toxicity Dalton Trans. 2012, 41, 5201
5. Shilov, A. E.; Shul'pin, G. B. Activation of C-H Bonds by Metal Complexes Chem. Rev. 1997, 97, 2879
6. Yang, Y.; Zhang, Y.; Hao, S.; Kan, Q. Tethering of Cu(II), Co(II) and Fe(III) Tetrahydro-salen and Salen Complexes onto Amino-functionalized SBA-15: Effects of Salen Ligand Hydrogenation on Catalytic Performances for Aerobic Epoxidation of Styrene Chem. Eng. J. 2011, 171, 1356
7. Kockrick, E.; Lescouet, T.; Kudrik, E. V.; Sorokin, A. B.; Farrusseng, D. Synergistic Effects of Encapsulated Phthalocyanine Complexes in MIL-101 for the Selective Aerobic Oxidation of Tetralin Chem. Commun. 2011, 47, 1562
8. Chen, L.; Yang, Y.; Jiang, D. CMPs as Scaffolds for Constructing Porous Catalytic Frameworks: A Built-in Heterogeneous Catalyst with High Activity and Selectivity Based on Nanoporous Metalloporphyrin Polymers J. Am. Chem. Soc. 2010, 132, 9138
9. Merlau, M. L.; Mejia, M. P.; Nguyen, S. T.; Hupp, J. T. Artificial Enzymes Formed through Directed Assembly of Molecular Square Encapsulated Epoxidation Catalysts Angew. Chem., Int. Ed. 2001, 40, 4239
10. Engelman, D. M. Membranes Are More Mosaic than Fluid Nature 2005, 438, 578
11. Zhou, D.; Cam, L. L.; Laughton, C. A. Mutagenesis Study at a Postulated Hydrophobic Region Near the Active Site of Aromatase Cytochrome P45 J. Biol. Chem. 1994, 269, 19501
12. Zehmer, J. K.; Bartz, R.; Liu, P. Identification of a Novel N-terminal Hydrophobic Sequence that Targets Proteins to Lipid Droplets J. Cell Sci. 2008, 121, 1582
13. Singh, A. K.; Singh, N.; Tiwari, A. First Structural Evidence for the Mode of Diffusion of Aromatic Ligands and Ligand-induced Closure of the Hydrophobic Channel in Heme Peroxidases J. Biol. Inorg. Chem. 2010, 15, 1099
14. Dong, Z. Y.; Huang, X.; Mao, S. Z. Cyclodextrin-Derived Mimic of Glutathione Peroxidase Exhibiting Enzymatic Specificity and High Catalytic Efficiency Chem.-Eur. J. 2006, 12, 3575
15. Chan, W. K.; Yu, W. Y.; Che, C. M. A Cyclodextrin-Modified Ketoester for Stereoselective Epoxidation of Alkenes J. Org. Chem. 2003, 68, 6576
16. Marinescu, L. G.; Bols, M. Very High Rate Enhancement of Benzyl Alcohol Oxidation by an Artificial Enzyme Angew. Chem., Int. Ed. 2006, 45, 4590
17. Astruc, D.; Boisselier, E.; Ornelas, C. Dendrimers Designed for Functions: From Physical, Photophysical, and Supramolecular Properties to Applications in Sensing, Catalysis, Molecular Electronics, Photonics, and Nanomedicine Chem. Rev. 2010, 110, 1857
18. Hayashi, Y.; Aratake, S.; Okano, T.; Takahashi, J.; Sumiya, T.; Shoji, M. Combined Proline-Surfactant Organocatalyst for the Highly Diastereo- and Enantioselective Aqueous Direct Cross-Aldol Reaction of Aldehydes Angew. Chem., Int. Ed. 2006, 45, 5527
19. Mase, N.; Nakai, Y.; Ohara, N.; Yoda, H.; Takabe, cK.; Tanaka, F.; Barbas, C. F., III Organocatalytic Direct Asymmetric Aldol Reactions in Water J. Am. Chem. Soc. 2006, 128, 734
20. Zhao, M.; Helms, B.; Slonkina, E.; Friedle, S.; Lee, D.; DuBois, J.; Hedman, B.; Hodgson, K. O.; Fréchet, J. M. J.; Lippard, S. J. Iron Complexes of Dendrimer- Appended Carboxylates for Activating Dioxygen and Oxidizing Hydrocarbons J. Am. Chem. Soc. 2008, 130, 4352
21. Yoshizawa, M.; Klosterman, J. K.; Fujita, M. Functional Molecular Flasks: New Properties and Reactions within Discrete, Self-Assembled Hosts Angew. Chem., Int. Ed. 2009, 48, 3418
22. Pluth, M. D.; Bergman, R. G.; Raymond, K. N. Proton-Mediated Chemistry and Catalysis in a Self-Assembled Supramolecular Host Acc. Chem. Res. 2009, 42, 1650
23. Hastings, C. J.; Pluth, M. D.; Bergman, R. G.; Raymond, K. N. Enzymelike Catalysis of the Nazarov Cyclization by Supramolecular Encapsulation J. Am. Chem. Soc. 2010, 132, 6938
24. Hu, S.; Li, J.; Xiang, J.; Pan, J.; Luo, S.; Cheng, J. Asymmetric Supramolecular Primary Amine Catalysis in Aqueous Buffer: Connections of Selective Recognition and Asymmetric Catalysis J. Am. Chem. Soc. 2010, 132, 7216
25. 2-Paradigm Chem. Rev. 2001, 101, 2613
26. Weng, K. C.; StaÌŠlgren, J. J. R.; Duval, D. J.; Risbud, S. H.; Frank, C. W. Fluid Biomembranes Supported on Nanoporous Aerogel/Xerogel Substrates Langmuir 2004, 20, 7232
27. Atanasov, V.; Atanasova, P. P.; Vockenroth, I. K.; Knorr, N.; Köper, I. A Molecular Toolkit for Highly Insulating Tethered Bilayer Lipid Membranes on Various Substrates Bioconjugate Chem. 2006, 17, 631
28. Groves, J. T.; Neumann, R. Regioselective Oxidation Catalysis in Synthetic Phospholipid Vesicles. Membrane-Spanning Steroidal Metalloporphyrins J. Am. Chem. Soc. 1989, 111, 2900
29. Parton, R. F.; Vankelecom, I. F. J.; Tas, D.; Janssen, K. B. M.; K.-Gerrits, P. P.; Jacobs, P. A. Membrane Occluded Catalysts: a Higher Order Mimic with Improved Performance J. Mol. Catal A: Chem. 1996, 113, 283
30. Liu, Z.; Ma, R.; Osada, M.; Iyi, N.; Ebina, Y.; Takada, K.; Sasaki, T. Synthesis, Anion Exchange, and Delamination of Co-Al Layered Double Hydroxide: Assembly of the Exfoliated Nanosheet/Polyanion Composite Films and Magneto-Optical Studies J. Am. Chem. Soc. 2006, 128, 4872
31. Pagano, M. A.; Forano, C.; Besse, J. P. Delamination of layered double hydroxides by use of surfactants Chem. Commun. 2000, 91
32. Yu, X. Q.; Huang, J. S.; Yu, W. Y.; Che, C. M. Polymer-Supported Ruthenium Porphyrins: Versatile and Robust Epoxidation Catalysts with Unusual Selectivity J. Am. Chem. Soc. 2000, 122, 5337
33. Cheng, R. J.; Lin, S. H.; Mo, H. M. Spectroscopic and Oxidation Studies of meso -Tetraphenyltetrabenzoporphyrin Carbonyl Complexes of Ruthenium (II): CO as the Probe to Elucidate the Bonding Characteristics of Porphyrins Organometallics 1997, 16, 2121
34. Chen, W.; Qu, B. Structural Characteristics and Thermal Properties of PE-g-MA/MgAl-LDH Exfoliation Nanocomposites Synthesized by Solution Intercalation Chem. Mater. 2003, 15, 3208
35. Li, B.; He, J. Multiple Effects of Dodecanesulfonate in the Crystal Growth Control and Morphosynthesis of Layered Double Hydroxides J. Phys. Chem. C 2008, 112, 10909
36. Drezdzon, M. A. Synthesis of Isopolymetalate-pillared Hydrotalcite via Organic-anion-pillared Precursors Inorg. Chem. 1988, 27, 4628
37. Meyn, M.; Beneke, K.; Lagaly, G. Anion-exchange Reactions of Layered Double Hydroxides Inorg. Chem. 1990, 29, 5201
38. Nagano, S.; Tosha, T.; Ishimori, K.; Morishima, I.; Poulos, T. L. Crystal Structure of the Cytochrome P450cam Mutant That Exhibits the Same Spectral Perturbations Induced by Putidaredoxin Binding J. Biol. Chem. 2004, 279, 42844
39. Kafunkova, E.; Lang, K.; Kubat, P.; Klementova, M.; Mosinger, J.; Slouf, M.; Thuilliez, A.; Leroux, F.; Verney, V.; Taviot-Guého, C. Porphyrin-Layered Double Hydroxide/Polymer Composites as Novel Ecological Photoactive Surfaces J. Mater. Chem. 2010, 20, 9423
40. Rebelo, S. L. H.; Goncalves, A. R.; Pereira, M. M.; Simoes, M. M. Q.; Neves, M. G. P. M. S.; Cavaleiro, J. A. S. Epoxidation Reactions with Hydrogen Peroxide Activated by a Novel Heterogeneous Metalloporphyrin Catalyst J. Mol. Catal. A: Chem. 2006, 256, 321
41. Iwasawa, T.; Hooley, R. J.; Rebek, J., Jr. Stabilization of Labile Carbonyl Addition Intermediates by a Synthetic Receptor Science 2007, 317, 493
42. Kellogg, G. E.; Abraham, D. J. Hydrophobicity: is LogPo/w More Than the Sum of Its Parts? Eur. J. Med. Chem. 2000, 35, 651
43. Tong, Z.; Shichi, T.; Takagi, K. Oxidation Catalysis of a Manganese(III)porphyrin Intercalated in Layered Double Hydroxide Clays Mater. Lett. 2003, 57, 2258
44. Halma, M.; Castro, K. A. D. F.; Taviot-Gueho, C.; Prévot, V.; Forano, K.; Wypych, F.; Nakagaki, S. Synthesis, Characterization, and Catalytic Activity of Anionic Iron(III) Porphyrins Intercalated into Layered Double Hydroxides J. Catal. 2008, 257, 233