Catalytic hydroxylation of benzene and toluene by an iron complex bearing a chelating di-pyridyl-di-NHC ligand

被引:89
作者
Raba, Andreas [1 ]
Cokoja, Mirza [1 ]
Herrmann, Wolfgang A. [1 ]
Kuehn, Fritz E. [1 ]
机构
[1] Tech Univ Munich, Catalysis Res Ctr, Chair Inorgan Chem Mol Catalysis, D-85747 Garching, Germany
关键词
AROMATIC HYDROXYLATION; POLYAZADENTATE COMPLEXES; IRON(IV)-OXO COMPLEXES; OXIDATION CATALYSIS; HYDROGEN-PEROXIDE; NONHEME; REGIOSELECTIVITY; EFFICIENCY; CLEAVAGE; INSIGHTS;
D O I
10.1039/c4cc02178a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This work reports on iron-catalysed hydroxylation of benzene and toluene using aqueous H2O2. While benzene is hydroxylated with a high selectivity to phenol, toluene is hydroxylated to cresols with a high selectivity for the ortho and para-position. An inverse KIE indicates the presence of a high valent Fe=O species during catalysis.
引用
收藏
页码:11454 / 11457
页数:4
相关论文
共 33 条
[1]   Transition-Metal-Catalyzed Synthesis of Hydroxylated Arenes [J].
Alonso, Diego A. ;
Najera, Carmen ;
Pastor, Isidro M. ;
Yus, Miguel .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (18) :5274-5284
[2]   Mechanistic Insights on the ortho-Hydroxylation of Aromatic Compounds by Non-heme Iron Complex: A Computational Case Study on the Comparative Oxidative Ability of Ferric-Hydroperoxo and High-Valent FeIV=O and FeV=O Intermediates [J].
Ansari, Azaj ;
Kaushik, Abhishek ;
Rajaraman, Gopalan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (11) :4235-4249
[3]   Non-heme iron polyazadentate complexes as catalysts for oxidations by H2O2:: particular efficiency in aromatic hydroxylations and beneficial effects of a reducing agent [J].
Balland, V ;
Mathieu, D ;
Pons-Y-Moll, N ;
Bartoli, JF ;
Banse, F ;
Battioni, P ;
Girerd, JJ ;
Mansuy, D .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 215 (1-2) :81-87
[4]  
Bianchi D, 2000, ANGEW CHEM INT EDIT, V39, P4321, DOI 10.1002/1521-3773(20001201)39:23<4321::AID-ANIE4321>3.0.CO
[5]  
2-5
[6]   A hybrid density functional study of O-O bond cleavage and phenyl ring hydroxylation for a biomimetic non-heme iron complex [J].
Borowski, T ;
Bassan, A ;
Siegbahn, PEM .
INORGANIC CHEMISTRY, 2004, 43 (10) :3277-3291
[7]   Concepts in homogeneous catalysis: the industrial view [J].
Cornils, B ;
Herrmann, WA .
JOURNAL OF CATALYSIS, 2003, 216 (1-2) :23-31
[8]   Combined experimental and theoretical study on aromatic hydroxylation by mononuclear nonheme iron(IV)-oxo complexes [J].
de Visser, Sam P. ;
Oh, Kyungeun ;
Han, Ah-Rim ;
Nam, Wonwoo .
INORGANIC CHEMISTRY, 2007, 46 (11) :4632-4641
[9]   Radical and non-radical chemistry of the Fenton-like systems in the presence of organic substrates [J].
Gozzo, F .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2001, 171 (1-2) :1-22
[10]   Understanding the M-(NHC) (NHC = N-heterocyclic carbene) bond [J].
Jacobsen, Heiko ;
Correa, Andrea ;
Poater, Albert ;
Costabile, Chiara ;
Cavallo, Luigi .
COORDINATION CHEMISTRY REVIEWS, 2009, 253 (5-6) :687-703