Literature DB >> 24587695

An Iron(II)(1,3-bis(2'-pyridylimino)isoindoline) Complex as a Catalyst for Substrate Oxidation with H2O2. Evidence for a Transient Peroxodiiron(III) Species.

József S Pap1, Matthew A Cranswick2, E Balogh-Hergovich1, Gábor Baráth1, Michel Giorgi3, Gregory T Rohde2, József Kaizer1, Gábor Speier1, Lawrence Que2.   

Abstract

The complex [Fe(indH)(solvent)3](ClO4)2 (1) has been isolated from the reaction of equimolar amounts of 1,3-bis(2'-pyridylimino)isoindoline (indH) and Fe(ClO4)2 in acetonitrile and characterized by X-ray crystallography and several spectroscopic techniques. It is a suitable catalyst for the oxidation of thioanisoles and benzyl alcohols with H2O2 as the oxidant. Hammett correlations and kinetic isotope effect experiments support the involvement of an electrophilic metal-based oxidant. A metastable green species (2) is observed when 1 is reacted with H2O2 at -40 °C, which has been characterized to have a FeIII(μ-O)(μ-O2)FeIII core on the basis of UV-Vis, electron paramagnetic resonance, resonance Raman, and X-ray absorption spectroscopic data.

Entities:  

Keywords:  Catalytic oxidation; Iron-peroxo intermediate; Isoindoline; Nonheme iron complex; Tridentate ligand

Year:  2013        PMID： 24587695      PMCID： PMC3935335          DOI： 10.1002/ejic.201300162

Source DB:  PubMed          Journal:  Eur J Inorg Chem        ISSN： 1434-1948            Impact factor:   2.524


  46 in total

1.  Dioxygen Activation by Enzymes Containing Binuclear Non-Heme Iron Clusters.

Authors:  Bradley J. Wallar; John D. Lipscomb
Journal:  Chem Rev       Date:  1996-11-07       Impact factor: 60.622

2.  (Mu-1,2-peroxo)diiron(III/III) complex as a precursor to the diiron(III/IV) intermediate X in the assembly of the iron-radical cofactor of ribonucleotide reductase from mouse.

Authors:  Danny Yun; Ricardo García-Serres; Brandon M Chicalese; Young H An; Boi Hanh Huynh; J Martin Bollinger
Journal:  Biochemistry       Date:  2007-01-27       Impact factor: 3.162

3.  Combined experimental and theoretical study on aromatic hydroxylation by mononuclear nonheme iron(IV)-oxo complexes.

Authors:  Sam P de Visser; Kyungeun Oh; Ah-Rim Han; Wonwoo Nam
Journal:  Inorg Chem       Date:  2007-04-20       Impact factor: 5.165

4.  Regioselective arene hydroxylation mediated by a (mu-peroxo)diiron(III) complex: a functional model for toluene monooxygenase.

Authors:  Mai Yamashita; Hideki Furutachi; Takehiko Tosha; Shuhei Fujinami; Wataru Saito; Yonezo Maeda; Kenji Takahashi; Koji Tanaka; Teizo Kitagawa; Masatatsu Suzuki
Journal:  J Am Chem Soc       Date:  2007-01-10       Impact factor: 15.419

5.  Correlating structure with function in bacterial multicomponent monooxygenases and related diiron proteins.

Authors:  Matthew H Sazinsky; Stephen J Lippard
Journal:  Acc Chem Res       Date:  2006-08       Impact factor: 22.384

6.  Enantioselective Sulfoxidation as a Probe for a Metal-Based Mechanism in H(2)O(2)-Dependent Oxidations Catalyzed by a Diiron Complex.

Authors:  Carole Duboc-Toia; Stéphane Ménage; Raymond Y. N. Ho; Lawrence Que; Claude Lambeaux; Marc Fontecave
Journal:  Inorg Chem       Date:  1999-03-22       Impact factor: 5.165

Review 7.  Dioxygen activation in soluble methane monooxygenase.

Authors:  Christine E Tinberg; Stephen J Lippard
Journal:  Acc Chem Res       Date:  2011-03-10       Impact factor: 22.384

8.  Revisiting the mechanism of dioxygen activation in soluble methane monooxygenase from M. capsulatus (Bath): evidence for a multi-step, proton-dependent reaction pathway.

Authors:  Christine E Tinberg; Stephen J Lippard
Journal:  Biochemistry       Date:  2009-12-29       Impact factor: 3.162

9.  Role of carboxylate bridges in modulating nonheme diiron(II)/O(2) reactivity.

Authors:  Miquel Costas; Clyde W Cady; Sergey V Kryatov; Manabendra Ray; Meghan J Ryan; Elena V Rybak-Akimova; Lawrence Que
Journal:  Inorg Chem       Date:  2003-11-17       Impact factor: 5.165

10.  Oxygen activation by nonheme iron(II) complexes: alpha-keto carboxylate versus carboxylate.

Authors:  Mark P Mehn; Kiyoshi Fujisawa; Eric L Hegg; Lawrence Que
Journal:  J Am Chem Soc       Date:  2003-07-02       Impact factor: 15.419
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  7 in total

Review 1.  Dioxygen Activation by Nonheme Diiron Enzymes: Diverse Dioxygen Adducts, High-Valent Intermediates, and Related Model Complexes.

Authors:  Andrew J Jasniewski; Lawrence Que
Journal:  Chem Rev       Date:  2018-02-05       Impact factor: 60.622

2.  Nonheme Diiron Oxygenase Mimic That Generates a Diferric-Peroxo Intermediate Capable of Catalytic Olefin Epoxidation and Alkane Hydroxylation Including Cyclohexane.

Authors:  Williamson N Oloo; Miklós Szávuly; József Kaizer; Lawrence Que
Journal:  Inorg Chem       Date:  2021-12-11       Impact factor: 5.165

3.  Explorations of the nonheme high-valent iron-oxo landscape: crystal structure of a synthetic complex with an [FeIV2(μ-O)2] diamond core relevant to the chemistry of sMMOH.

Authors:  Gregory T Rohde; Genqiang Xue; Lawrence Que
Journal:  Faraday Discuss       Date:  2022-05-18       Impact factor: 4.394

4.  A Carboxylate Shift Regulates Dioxygen Activation by the Diiron Nonheme β-Hydroxylase CmlA upon Binding of a Substrate-Loaded Nonribosomal Peptide Synthetase.

Authors:  Andrew J Jasniewski; Cory J Knoot; John D Lipscomb; Lawrence Que
Journal:  Biochemistry       Date:  2016-10-07       Impact factor: 3.162

5.  Hydrogen-Atom Transfer Oxidation with H2O2 Catalyzed by [FeII(1,2-bis(2,2'-bipyridyl-6-yl)ethane(H2O)2]2+: Likely Involvement of a (μ-Hydroxo)(μ-1,2-peroxo)diiron(III) Intermediate.

Authors:  Alexander M Khenkin; Madhu Vedichi; Linda J W Shimon; Matthew A Cranswick; Johannes E M N Klein; Lawrence Que; Ronny Neumann
Journal:  Isr J Chem       Date:  2017-09-13       Impact factor: 3.333

6.  Unprecedented (μ-1,1-Peroxo)diferric Structure for the Ambiphilic Orange Peroxo Intermediate of the Nonheme N-Oxygenase CmlI.

Authors:  Andrew J Jasniewski; Anna J Komor; John D Lipscomb; Lawrence Que
Journal:  J Am Chem Soc       Date:  2017-07-19       Impact factor: 15.419

7.  X-ray absorption spectroscopic characterization of the diferric-peroxo intermediate of human deoxyhypusine hydroxylase in the presence of its substrate eIF5a.

Authors:  Andrew J Jasniewski; Lisa M Engstrom; Van V Vu; Myung Hee Park; Lawrence Que
Journal:  J Biol Inorg Chem       Date:  2016-07-05       Impact factor: 3.358
  7 in total

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