Ionic liquids as reaction media in catalytic oxidations with manganese and iron pyridyl triazacyclononane complexes

被引:11
作者
Lentini, Sara [1 ]
Galloni, Pierluca [1 ]
Garcia-Bosch, Isaac [2 ]
Costas, Miquel [2 ]
Conte, Valeria [1 ]
机构
[1] Univ Roma Tor Vergata, Dipartimento Sci & Tecnol Chim, I-00133 Rome, Italy
[2] Univ Girona, Dept Quim, Girona 17071, Spain
关键词
Oxidation; Manganese; Iron; Bioinspired catalysis; Hydrogen peroxide; Ionic liquids; C-H GROUPS; NONHEME IRON; CIS-DIHYDROXYLATION; HYDROGEN-PEROXIDE; HIGHLY EFFICIENT; EPOXIDATION; H2O2; ALKENES; WATER; OLEFINS;
D O I
10.1016/j.ica.2013.10.016
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A family of bioinspired iron and manganese complexes of general formula [M-II(CF3SO3)(2)((Me, X)PyTACN)], where (Me,X)PyTACN = 1-[2 '-(6-Rpyridyl)methyl]-4,7-dimethyl-1,4,7-triazacyclononane, R=H, Me and M = Fe, and Mn has been studied as efficient catalytic systems for hydrogen peroxide oxidation reactions. Previous work revealed that the manganese derivative [Mn-II(CF3SO3)(2)((Me, H)PyTACN)], 1, in acetonitrile exhibits a high catalytic activity in the epoxidation of a wide range of olefins (TON: 810-4500), using acetic acid and hydrogen peroxide as primary oxidant. The analogous iron based complex [Fe-II(CF3SO3)(2) (Me, HPyTACN)], 2a and [Fe-II(CF3SO3)(2)((Me,Me)PyTACN)], 2b promote the high added value oxidation reaction of alkanes in mild conditions. In this work sustainability and selectivity of the oxidative system is improved with the use of the ionic liquids (ILs) as reaction medium. The possibility to recycle the catalytic phase without loss of the activity with respect to the original reaction in acetonitrile (MeCN) is reported. (C) 2013 Elsevier B. V. All rights reserved.
引用
收藏
页码:60 / 64
页数:5
相关论文
共 53 条
[1]   Improvement of ferrocene acylation. Conventional vs. microwave heating for scandium-catalyzed reaction in alkylmethylimidazolium-based ionic liquids [J].
Berardi, Serena ;
Conte, Valeria ;
Fiorani, Giulia ;
Floris, Barbara ;
Galloni, Pierluca .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (18) :3015-3020
[2]   Hydrophobic, highly conductive ambient-temperature molten salts [J].
Bonhote, P ;
Dias, AP ;
Papageorgiou, N ;
Kalyanasundaram, K ;
Gratzel, M .
INORGANIC CHEMISTRY, 1996, 35 (05) :1168-1178
[3]   Sustainable epoxidation of electron-poor Olefins with hydrogen peroxide in ionic liquids and recovery of the products with Supercritical CO2 [J].
Bortolini, O ;
Campestrini, S ;
Conte, V ;
Fantin, G ;
Fogagnolo, M ;
Maietti, S .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (24) :4804-4809
[4]  
Burrell AK, 2007, GREEN CHEM, V9, P449, DOI 10.1039/b615950h
[5]   Spin state tuning of non-heme iron-catalyzed hydrocarbon oxidations:: participation of FeIII-OOH and FeV=O intermediates [J].
Chen, K ;
Costas, M ;
Que, L .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2002, (05) :672-679
[6]   Ionic liquids: solvent properties and organic reactivity [J].
Chiappe, C ;
Pieraccini, D .
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2005, 18 (04) :275-297
[7]   Practical manganese-catalysed highly enantioselective cis-dihydroxylation of electron-deficient alkenes and detection of a cis-dioxomanganese(V) intermediate by high resolution ESI-MS analysis [J].
Chow, Toby Wai-Shan ;
Liu, Yungen ;
Che, Chi-Ming .
CHEMICAL COMMUNICATIONS, 2011, 47 (40) :11204-11206
[8]   cis-Dihydroxylation of Alkenes with Oxone Catalyzed by Iron Complexes of a Macrocyclic Tetraaza Ligand and Reaction Mechanism by ESI-MS Spectrometry and DFT Calculations [J].
Chow, Toby Wai-Shan ;
Wong, Ella Lai-Ming ;
Guo, Zhen ;
Liu, Yungen ;
Huang, Jie-Sheng ;
Che, Chi-Ming .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (38) :13229-13239
[9]   Chemistry goes green [J].
Clark, James H. .
NATURE CHEMISTRY, 2009, 1 (01) :12-13
[10]   A novel platform for modeling oxidative catalysis in non-heme iron oxygenases with unprecedented efficiency [J].
Company, Anna ;
Gomez, Laura ;
Fontrodona, Xavier ;
Ribas, Xavi ;
Costas, Miquel .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (19) :5727-5731