ChemCatChem

Cover image for Vol. 3 Issue 5

May 9, 2011

Volume 3, Issue 5

Pages 785–915

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Highlights
    7. Communications
    8. Full Papers
    9. Book Review
    10. Preview
    1. Cover Picture: Mechanistic Study of the Pd/TOMPP-Catalyzed Telomerization of 1,3-Butadiene with Biomass-Based Alcohols: On the Reversibility of Phosphine Alkylation (ChemCatChem 5/2011) (page 785)

      Peter J. C. Hausoul, Dr. Andrei N. Parvulescu, Dr. Martin Lutz, Prof. Dr. Anthony L. Spek, Dr. Pieter C. A. Bruijnincx, Prof. Dr. Robertus J. M. Klein Gebbink and Prof. Dr. Bert M. Weckhuysen

      Version of Record online: 4 MAY 2011 | DOI: 10.1002/cctc.201190018

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      The cover picture shows a view inside of the ‘black box’ of the Pd/TOMPP-catalyzed (TOMPP=tris(2-methoxyphenyl)phosphine) telomerization reaction of 1,3-butadiene with carbohydrate substrates. The detailed analysis of post-catalytic reaction mixtures, in the Full Paper on p. 845 ff., A. L. Spek, R. J. M. Klein Gebbink, B. M. Weckhuysen et al., revealed that the phosphine is converted to the phosphonium species and that this process is the main cause of catalyst deactivation. Coordination studies on the in situ formed phosphonium species show that this reaction is reversible and that the key catalytic intermediate [Pd(1,2,3,7,8-η5-octa-2,7-dien-1-yl)(TOMPP)]+ can be reformed. This illustrates that the ‘gears’ of the reaction mechanism can be rewound to study the reaction pathways and intermediates involved in phosphonium formation.

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Highlights
    7. Communications
    8. Full Papers
    9. Book Review
    10. Preview
  3. News

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Highlights
    7. Communications
    8. Full Papers
    9. Book Review
    10. Preview
  4. Review

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Highlights
    7. Communications
    8. Full Papers
    9. Book Review
    10. Preview
    1. Supported Transition Metal Catalysts for Hydrodechlorination Reactions (pages 800–821)

      Prof. Mark A. Keane

      Version of Record online: 12 APR 2011 | DOI: 10.1002/cctc.201000432

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      Critical discharge concerns: The presence of chloro-organics in effluent discharges is of increasing concern, owing to the mounting evidence of adverse stratospheric ozone, ecological effects, and the impact on public health. Catalytic hydrodechlorination represents a progressive means of detoxification and recycling. This Review sets out the benefits over separation/oxidation methodologies and, focuses on the transformation of chloro-aromatics

  5. Highlights

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Highlights
    7. Communications
    8. Full Papers
    9. Book Review
    10. Preview
    1. Protection–deprotection Methods Applied to Metal–Organic Frameworks for the Design of Original Single-Site Catalysts (pages 823–826)

      Dr. Jérôme Canivet and Dr. David Farrusseng

      Version of Record online: 23 FEB 2011 | DOI: 10.1002/cctc.201100002

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      Post-synthetic modification of metal–organic frameworks is carried out in a novel fashion for the synthesis of single-site catalysts. Protection–deprotection methodologies open new perspectives to “unlock” protected functionalities to obtain highly active and/or coordinating moieties on MOFs. This could facilitate the immobilization of organometallic catalysts inside MOF cavities.

    2. tert-Butoxide-Mediated C[BOND]H Bond Arylation of Aromatic Compounds with Haloarenes (pages 827–829)

      Shuichi Yanagisawa and Prof. Dr. Kenichiro Itami

      Version of Record online: 18 FEB 2011 | DOI: 10.1002/cctc.201000431

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      Say halo, wave goodbye: Recently, several research groups have reported that the C[BOND]H bond arylation of aromatic compounds with haloarenes can be promoted by potassium or sodium tert-butoxide, without the addition of any exogenous transition metal species. These serendipitous discoveries are highlighted and summarized.

  6. Communications

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Highlights
    7. Communications
    8. Full Papers
    9. Book Review
    10. Preview
    1. Ambient Fixation of Carbon Dioxide using a ZnIIsalphen Catalyst (pages 831–834)

      Dr. Antonello Decortes and Dr. Arjan W. Kleij

      Version of Record online: 2 MAR 2011 | DOI: 10.1002/cctc.201100031

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      Conditions matter: The cycloaddition of carbon dioxide to various epoxides catalyzed by Zn(salphen) complexes to selectively yield cyclic carbonates may be performed under ambient conditions. This newly developed process for cyclic carbonates meets the requirements of sustainable and green technology.

    2. High-Selectivity Hydrogenation of Chloronitrobenzene to Chloroaniline Over Magnesium Fluoride-Supported Bimetallic Ruthenium-Copper Catalysts (pages 835–838)

      Dr. Mariusz Pietrowski, Michał Zieliński and Maria Wojciechowska

      Version of Record online: 17 FEB 2011 | DOI: 10.1002/cctc.201100009

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      An aniline exclusive: The introduction of copper to a Ru/MgF2 catalyst results in the strong inhibition of the side reaction of hydrodechlorination during the hydrogenation of ortho-chloronitrobenzene and allows ortho-chloroaniline to be produced at 100 % selectivity.

    3. Insight into Copper-Based Catalysts: Microwave-Assisted Morphosynthesis, In Situ Reduction Studies, and Dehydrogenation of Ethanol (pages 839–843)

      Diogo P. Volanti, André G. Sato, Prof. Dr. Marcelo O. Orlandi, Prof. Dr. José M. C. Bueno, Prof. Dr. Elson Longo and Prof. Dr. Juan Andrés

      Version of Record online: 14 FEB 2011 | DOI: 10.1002/cctc.201000462

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      Form an orderly Cu: Copper-based catalysts obtained by microwave-assisted morphosynthesis were correlated with the dehydrogenation of ethanol. The degree of reduction was monitored using time-resolved in situ XANES during TPR under H2. A semiquantitative estimation of the different chemical forms (Cu2+, Cu+, and/or Cu0) was obtained. The results suggest intrinsic particularities due to different morphologies at the active state in reduction kinetics.

  7. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Highlights
    7. Communications
    8. Full Papers
    9. Book Review
    10. Preview
    1. Mechanistic Study of the Pd/TOMPP-Catalyzed Telomerization of 1,3-Butadiene with Biomass-Based Alcohols: On the Reversibility of Phosphine Alkylation (pages 845–852)

      Peter J. C. Hausoul, Dr. Andrei N. Parvulescu, Dr. Martin Lutz, Prof. Dr. Anthony L. Spek, Dr. Pieter C. A. Bruijnincx, Prof. Dr. Robertus J. M. Klein Gebbink and Prof. Dr. Bert M. Weckhuysen

      Version of Record online: 23 MAR 2011 | DOI: 10.1002/cctc.201100048

      Thumbnail image of graphical abstract

      Rewind reversible: Analysis of post-catalytic mixtures of Pd/TOMPP-catalyzed telomerization reactions revealed that the ligand is alkylated during catalysis. Coordination reactions show that this process is reversible and an extension to the Pd/TOMPP-catalyzed telomerization mechanism is proposed. The influence of this route is discussed with respect to the hemi-acetal induced catalyst deactivation observed for carbohydrate substrates. (TOMPP=tris(2-methoxyphenyl)phosphine)

    2. Amidases Have a Hydrogen Bond that Facilitates Nitrogen Inversion, but Esterases Have Not (pages 853–860)

      Per-Olof Syrén and Prof. Karl Hult

      Version of Record online: 23 FEB 2011 | DOI: 10.1002/cctc.201000448

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      Amidase or esterase: By using molecular modeling we found a hydrogen bond donated by the scissile NH-group of the peptide substrate in the transition state facilitating nitrogen inversion in the active site of amidases. The interaction, which is missing in esterases, was found in sixteen analyzed amidases representing ten different reaction mechanisms and eleven folding families.

    3. Insight into the Mechanism of Dihydrogen-Heterolysis at Cyclopentadienone Iron Complexes and Subsequent C[DOUBLE BOND]X Hydrogenation (pages 861–867)

      Adrian von der Höh and Prof. Dr. Albrecht Berkessel

      Version of Record online: 21 FEB 2011 | DOI: 10.1002/cctc.201000428

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      Fast on the uptake: Bifunctional cyclopentadienone-iron complexes catalyze the hydrogenation of carbonyl C[DOUBLE BOND]O and imine C[DOUBLE BOND]N double bonds. The mechanism of hydrogen uptake and hydrogen transfer was investigated by DFT methods. The latter was found to be different for C[DOUBLE BOND]O (single-step concerted) and C[DOUBLE BOND]N (two-step via iminium intermediate) hydrogenation.

    4. Low-temperature CH4 Catalytic Combustion over Pd Catalyst Supported on Co3O4 Nanocrystals with Well-Defined Crystal Planes (pages 868–874)

      Dr. Linhua Hu, Dr. Qing Peng and Prof. Yadong Li

      Version of Record online: 8 MAR 2011 | DOI: 10.1002/cctc.201000407

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      It's all on the surface: The structure–property relationship for the low-temperature combustion of methane on supported Pd catalysts has been investigated by tuning the shape and the exposed crystal planes of the supporting Co3O4-nanocrystals. The strong surface interaction between Pd2+ and the cobalt–oxygen group in Pd/Co3O4 nanosheets has been analyzed by using HRTEM and temperature programmed reduction experiments.

    5. Ionic Liquid-Inspired Cations Covalently Bound to Formate Dehydrogenase Improve its Stability and Activity in Ionic Liquids (pages 875–882)

      Mourad Bekhouche, Prof. Dr. Loïc J. Blum and Dr. Bastien Doumèche

      Version of Record online: 18 FEB 2011 | DOI: 10.1002/cctc.201000390

      Thumbnail image of graphical abstract

      Formate dehydrogenase in ionic liquid: Chemical modification of a formate dehydrogenase by hydroxyalkyl imidazolium, hydroxyalkyl pyrrolidinium, or cholinium cations prevents its unfolding in the presence of [MMIm][Me2PO4] (MMIm: 1-methyl-3-methyl imidazolium dimethylphosphate) according to the B coefficient of the cations.

    6. Stereoselective Palladium Catalyzed Allylic Phosphination (pages 883–886)

      Dr. Amélie Duraud, Dr. Olivier Jacquet, Prof. Jean-Claude Fiaud, Dr. Régis Guillot and Dr. Martial Toffano

      Version of Record online: 14 MAR 2011 | DOI: 10.1002/cctc.201000458

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      Chiral enantiopure 2,5-diphenylphospholane borane (1) is an interesting nucleophile for allylic phosphination in the presence of palladium complexes to form C[BOND]P bonds. A highly diastereoselective allylic phosphination reaction was performed using a chiral palladium-DACH-naphthyl ligand as the catalyst. The secondary phosphine-borane complex could be classified as a NuL type nucleophile.

    7. Electronic Effects in the Catalytic Hydrosilylation with In-Situ Generated Iron(II)-Catalysts (pages 887–892)

      Keven Muller, Anett Schubert, Dr. Thomas Jozak, Annegret Ahrens-Botzong, Prof. Dr. Volker Schünemann and Prof. Dr. Werner R. Thiel

      Version of Record online: 23 MAR 2011 | DOI: 10.1002/cctc.201000449

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      Electronic effects in electronic worlds: Pyrazole and pyrimidine derived bidentate ligands enable iron(II) catalyzed hydrosilylation of carbonyl compounds in nonpolar solvents with cheap polymethylhydrosiloxane as the silane source.

    8. Palladium-Catalyzed Direct Benzylation of Xanthines (pages 893–897)

      Sophian Sahnoun, Dr. Samir Messaoudi, Prof. Jean-Daniel Brion and Dr. Mouâd Alami

      Version of Record online: 17 MAR 2011 | DOI: 10.1002/cctc.201000439

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      An efficient and versatile synthetic palladium-catalyzed sp2 C[BOND]H bond activation approach for the preparation of a series of C8-benzyl xanthines is developed using benzyl chlorides as coupling partners. The reactions take place rapidly in 1,4-dioxane and proceed in the presence of [PdCl2(MeCN)2]/P(o-tolyl)3 as a catalyst system and Cs2CO3 as a base to afford the corresponding C8-benzylated xanthines in good to excellent yields.

    9. DFT Comparison of N-Nitrosodimethylamine Decomposition Pathways Over Ni and Pd (pages 898–903)

      Dr. V. A. Ranea, Prof. T. J. Strathmann, Prof. J. R. Shapley and Prof. W. F. Schneider

      Version of Record online: 8 MAR 2011 | DOI: 10.1002/cctc.201000398

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      Figure it out: DFT calculations are used to contrast the contributions of N[BOND]N and N[BOND]O bond cleavage to the catalytic reduction of the environmental pollutant N-nitrosodimethylamine (NDMA).

    10. Ruthenium Carbene Siloxide Complexes Immobilized on Silica: Synthesis and Catalytic Activity in Olefin Metathesis (pages 904–910)

      Prof. Dr. Bogdan Marciniec, Dr. Szymon Rogalski, Prof. Dr. Marek J. Potrzebowski and Dr. Cezary Pietraszuk

      Version of Record online: 14 JAN 2011 | DOI: 10.1002/cctc.201000376

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      Busting out ruthenium complexes: Ruthenium complexes based on second generation Hoveyda–Grubbs catalysts, directly attached to silica (see scheme) were synthesized and characterized by using cross polarization magic angle spinning 13C NMR (CP MAS 13C NMR) spectroscopy. The complexes exhibit catalytic activity in selected metathesis reactions and can be recycled up to 15 times.

  8. Book Review

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Highlights
    7. Communications
    8. Full Papers
    9. Book Review
    10. Preview
    1. Catalytic Asymmetric Synthesis, 3rdEdition. Edited by Iwao Oljima (pages 911–912)

      Professor Pat Guiry

      Version of Record online: 8 MAR 2011 | DOI: 10.1002/cctc.201100053

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      John Wiley & Sons, Inc. 2010. 985 pp., Hardcover € 152.00—ISBN 978-0-470-17577-4

  9. Preview

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Highlights
    7. Communications
    8. Full Papers
    9. Book Review
    10. Preview
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      Preview: ChemCatChem 6/2011 (page 915)

      Version of Record online: 4 MAY 2011 | DOI: 10.1002/cctc.201190021

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