ChemCatChem

Cover image for Vol. 3 Issue 4

April 11, 2011

Volume 3, Issue 4

Pages 617–783

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Highlights
    9. Communications
    10. Full Papers
    11. Book Review
    12. Preview
    1. Cover Picture: Shaped RuO2/SnO2–Al2O3 Catalyst for Large-Scale Stable Cl2 Production by HCl Oxidation (ChemCatChem 4/2011) (page 617)

      Dr. Cecilia Mondelli, Amol P. Amrute, Dr. Frank Krumeich, Dr. Timm Schmidt and Prof. Javier Pérez-Ramírez

      Version of Record online: 5 APR 2011 | DOI: 10.1002/cctc.201190013

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      The cover picture shows the key stages in the development of a suitable heterogeneous catalyst for HCl oxidation (Deacon process), from fundamental studies to pilot-scale tests with shaped bodies. In their Communication on p. 657 ff., Pérez-Ramírez et al. report the design of a novel RuO2/SnO2-Al2O3 catalyst for HCl oxidation with outstanding activity and lifetime. This performance stems from the optimal nanostructuring of the active phase (RuO2) onto the support (SnO2) in combination with the stabilizing effect of Al2O3 at the mesoscale. The prompt implementation of this catalytic system for chlorine recycling in the chemical industry is expected.

  2. Editorial

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Highlights
    9. Communications
    10. Full Papers
    11. Book Review
    12. Preview
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      Editorial: Solving the Material and Energy Challenges of the Future (pages 619–621)

      Prof. Bert M. Weckhuysen, Prof. Luis A. Oro and Prof. Uwe T. Bornscheuer

      Version of Record online: 5 APR 2011 | DOI: 10.1002/cctc.201100094

  3. Graphical Abstract

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

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Highlights
    9. Communications
    10. Full Papers
    11. Book Review
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      Corrigendum: Fullerene-Mediated Activation of Dihydrogen: A New Method of Metal-Free Catalytic Hydrogenation (page 629)

      Jochen Niemeyer and Gerhard Erker

      Version of Record online: 5 APR 2011 | DOI: 10.1002/cctc.201190015

      This article corrects:

      Fullerene-Mediated Activation of Dihydrogen: A New Method of Metal-Free Catalytic Hydrogenation

      Vol. 2, Issue 5, 499–500, Version of Record online: 8 APR 2010

  5. News

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

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Highlights
    9. Communications
    10. Full Papers
    11. Book Review
    12. Preview
    1. Advances in the Catalytic Asymmetric Arylation of Imines using Organoboron Reagents: An Approach to Chiral Arylamines (pages 635–645)

      Carolina S. Marques and Prof. Anthony J. Burke

      Version of Record online: 17 MAR 2011 | DOI: 10.1002/cctc.201000369

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      A quest for amine treasure: The synthesis of chiral amines is a current challenge in the field of drug discovery. One process by which chiral amines can be produced is through asymmetric catalysis. The use of cheap, easy handled and low toxicity organoboron reagents can be easily combined with imine substrates, together with rhodium or palladium catalysts, to give the corresponding chiral amine products.

  7. Highlights

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Highlights
    9. Communications
    10. Full Papers
    11. Book Review
    12. Preview
    1. Metallopeptides for Enantioselective Catalysis (pages 647–648)

      Dr. Gerard Roelfes

      Version of Record online: 24 JAN 2011 | DOI: 10.1002/cctc.201000413

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      Helix the cat: Metalloenzymes are the benchmark catalysts for efficient enantioselective chemical transformations and, as such, a source of inspiration for catalyst design. Novel metallopeptides, comprising a dirhodium tetracarboxylate active site embedded in a helical peptide dimer, have been shown to catalyze highly enantioselective Si[BOND]H insertion reactions.

    2. Electronic Fine-Tuning of Carbene Ligands and its Impact on Gold Catalysis (pages 649–652)

      Philipp Klahn and Stefan F. Kirsch

      Version of Record online: 18 JAN 2011 | DOI: 10.1002/cctc.201000366

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      Playhouse NHC: Modulation of the π-acceptor properties of ancillary carbene ligands allows great control over competing pathways in gold(I)-catalyzed reactions. High selectivity can be achieved for the transformation of allenenes within a series of structurally similar but electronically different N-heterocyclic carbenes (NHCs). The experimental results are supported by DFT calculations.

  8. Communications

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Highlights
    9. Communications
    10. Full Papers
    11. Book Review
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    1. Dual Catalysis in Highly Enantioselective Multicomponent Reaction with Water: An Efficient Approach to Chiral β-Amino-α-Hydroxy Acid Derivatives (pages 653–656)

      Yu Qian, Changcheng Jing, Taoda Shi, Jingjing Ji, Min Tang, Jing Zhou, Changwei Zhai and Prof. Wenhao Hu

      Version of Record online: 25 JAN 2011 | DOI: 10.1002/cctc.201000437

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      Dual to the death: Catalyzed by [Rh2(OAc)4] and a chiral phosphoric acid, an enantioselective symmetric three-component reaction of diazo compounds with imines and water is reported to give β-amino-α-hydroxy acid derivatives in good yield (up to 86 %) with excellent diastereoselectivity (up to 98:2 d.r.) and enantioselectivity (up to 97 % ee).

    2. Shaped RuO2/SnO2–Al2O3 Catalyst for Large-Scale Stable Cl2 Production by HCl Oxidation (pages 657–660)

      Dr. Cecilia Mondelli, Amol P. Amrute, Dr. Frank Krumeich, Dr. Timm Schmidt and Prof. Javier Pérez-Ramírez

      Version of Record online: 18 JAN 2011 | DOI: 10.1002/cctc.201000424

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      Deacon process revisited: A shaped RuO2/SnO2–Al2O3 catalyst was designed for highly active and stable performance in HCl oxidation to Cl2. In addition to its binding effect, alumina acts as a stabilizer to prevent sintering, endowing the catalyst with extraordinary longevity. Pilot tests give solid prospects for industrial implementation of this catalytic system.

    3. CuO Nanoparticles on Ionic Polymer for Coupling Reactions of Aryl Bromides and Chlorides with Phenols (pages 661–665)

      Tongjie Hu, Xiaorong Chen, Prof. Dr. Jun Wang and Prof. Dr. Jun Huang

      Version of Record online: 15 FEB 2011 | DOI: 10.1002/cctc.201000416

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      Halides hooking up: A Cu nanocatalyst was prepared and applied for the coupling of various arylbromides and chlorides with phenols at low catalyst loading.

    4. A Facile and Efficient Iron-Catalyzed Reduction of Sulfoxides to Sulfides (pages 666–670)

      Dr. Stephan Enthaler

      Version of Record online: 27 JAN 2011 | DOI: 10.1002/cctc.201000400

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      SO it goes: A straightforward method for the deoxygenation of sulfoxides based on iron catalysts is presented. Excellent performance is demonstrated by a system composed of [Fe2(CO)9] as catalyst and polymethylhydrosiloxane (PMHS) or PhSiH3 as reducing reagent under non-inert conditions. The outstanding applicability of this procedure is shown in the reduction of various substrates with excellent yields and good functional-group tolerance.

    5. CO+NO versus CO+O2 Reaction on Monolayer FeO(111) Films on Pt(111) (pages 671–674)

      Dr. Yu Lei, Mikolaj Lewandowski, Ying-Na Sun, Yuichi Fujimori, Yulija Martynova, Dr. Irene M. N. Groot, Prof. Randall J. Meyer, Dr. Livia Giordano, Prof. Gianfranco Pacchioni, Dr. Jacek Goniakowski, Prof. Claudine Noguera, Dr. Shamil Shaikhutdinov and Prof. Hans-Joachim Freund

      Version of Record online: 4 JAN 2011 | DOI: 10.1002/cctc.201000388

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      Caught on film: NO exposed to monolayer FeO(111) film grown on Pt(111) at elevated pressures readily forms a trilayer OFeO film that is virtually identical to that formed with O2. However, CO2 production in the CO+NO reaction is negligible as compared to CO+O2, which is rationalized in terms of the replenishment of oxygen vacancies as the rate-limiting step that proceeds much faster with O2 than NO.

    6. Engineering the Environment of a Catalytic Metal–Organic Framework by Postsynthetic Hydrophobization (pages 675–678)

      Dr. Jerome Canivet, Dr. Sonia Aguado, Cecile Daniel and Dr. David Farrusseng

      Version of Record online: 3 JAN 2011 | DOI: 10.1002/cctc.201000386

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      Repel without a pause: A new metal–organic framework (MOF), the substituted imidazolate material SIM-1, is easily converted into the very hydrophobic SIM-2(C12) by post-synthetic modification with long alkyl chains. The new water-repellent MOF shows the highest catalytic activity ever found for a MOF in the Knoevenagel condensation.

    7. A Practical and Enantioselective Approach to Tetrahydrocarbazoles by Asymmetric Organocatalysis (pages 679–683)

      Xiao-Yu Zhu, Xiao-Lei An, Dr. Chang-Feng Li, Fu-Gen Zhang, Qiu-Lin Hua, Dr. Jia-Rong Chen and Prof. Wen-Jing Xiao

      Version of Record online: 29 DEC 2010 | DOI: 10.1002/cctc.201000379

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      A highly enantioselective intramolecular Friedel–Crafts-type alkylation of ω-indolyl α,β-unsaturated aldehydes has been disclosed. This reaction allows efficient access to functionalized tetrahydrocarbazoles in high yields (up to 95 %) with excellent enantioselectivities (up to 98 % ee). This procedure is also successful in the asymmetric synthesis of pyrrole-fused heterocycles (up to 88 % ee).

    8. Highly Efficient Alcohol Oxidation on Nanoporous VSB-5 Nickel Phosphate Catalyst Functionalized by NaOH Treatment (pages 684–689)

      Dr. Chunlin Li, Hirofumi Kawada, Xiaoyu Sun, Prof. Hengyong Xu, Dr. Yoshiharu Yoneyama and Prof. Noritatsu Tsubaki

      Version of Record online: 4 JAN 2011 | DOI: 10.1002/cctc.201000372

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      Your treating art: Selective catalytic oxidation of alcohols to corresponding aldehydes or ketones under mild conditions with molecular oxygen is the foundation of many important fine chemical processes. Functionalizing VSB-5 nickel phosphate by simple NaOH treatment generates an active phase of Ni(OH)2 inside the channels, leading to a shape-selective, environmentally friendly, additive-free heterogeneous catalyst for the selective oxidation of various alcohols.

    9. New Strategy for Enantioselective Heterogeneous Catalysis: Immobilization of both Metal Nanoparticles and Chiral Modifiers on Mesoporous Silica Nanoparticles (pages 690–694)

      Dr. Yulin Huang, Dr. Shu Xu and Prof. Dr. Victor S.-Y. Lin

      Version of Record online: 30 JAN 2011 | DOI: 10.1002/cctc.201000363

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      Are you a silican or a silican′t? By using a cocondensation method, well defined rhodium nanoparticles and chiral reagent (−)-cinchonidine were immobilized and stabilized on mesoporous silica nanoparticle surface simultaneously. For the enantioselective hydrogenation of ethyl pyruvate, the enantioselectivity was very well preserved during the catalyst recycling without any additional chiral reagent supplement.

    10. Selective Hydrogenations with Ag[BOND]Pd Catalysts Prepared by Galvanic Exchange Reactions (pages 695–697)

      Christina F. Calver, Dr. Priyabrat Dash and Prof. Robert W. J. Scott

      Version of Record online: 4 JAN 2011 | DOI: 10.1002/cctc.201000346

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      Treading on eggshells: AgPd nanoparticles were prepared by galvanic exchange reactions and used as hydrogenation catalysts for allylic alcohols. The results show that thin Pd shells on Ag cores leads to improved selectivity of hydrogenation reactions versus isomerization reactions. Extended X-ray absorption fine structure (EXAFS) spectroscopy was used to determine that nanoparticles were more accurately described as cluster-in-cluster structures with Pd clusters on a central Ag core.

  9. Full Papers

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Highlights
    9. Communications
    10. Full Papers
    11. Book Review
    12. Preview
    1. Confirmation of Chirality in Homogeneous and Heterogeneous Salen-Based Catalysts (pages 699–703)

      Alan J. McCue, Dr. Richard P. K. Wells and Prof. James A. Anderson

      Version of Record online: 27 JAN 2011 | DOI: 10.1002/cctc.201000387

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      It′s not all plain salen: Chiral, achiral, and supported [Mn(salen)] complexes are investigated in the epoxidation of α-pinene and limonene. Results show that the stereochemical outcome of the reaction is independent of the chirality surrounding the metal center, thus challenging the use of such substrates as a tool to assess chirality in a catalyst complex and, in particular, whether chirality is retained following immobilization.

    2. Catalytic Co-Homologation of Alkanes and Dimethyl Ether and Promotion by Adamantane as a Hydride Transfer Co-Catalyst (pages 704–718)

      Prof. Dante A. Simonetti, John H. Ahn and Dr. Enrique Iglesia

      Version of Record online: 15 FEB 2011 | DOI: 10.1002/cctc.201000383

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      It′s tough to be adamantane: The methylation of alkanes with C1 intermediates derived from dimethyl ether (DME) on acid BEA zeolites at low temperatures (<500 K) leads to larger branched alkanes without carbon rejection as arenes, a process required to provide H-atoms necessary to convert DME to alkanes. Adamantane acts as a hydride transfer co-catalyst and increases the rate of incorporation of alkanes into chain growth pathways.

    3. Autodisplay of Nitrilase from Alcaligenes faecalis in E. coli Yields a Whole Cell Biocatalyst for the Synthesis of Enantiomerically Pure (R)-Mandelic Acid (pages 719–725)

      Christian Detzel, Dr. Ruth Maas and Prof. Dr. Joachim Jose

      Version of Record online: 4 FEB 2011 | DOI: 10.1002/cctc.201000382

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      The enzyme factory: The Autodisplay-mediated surface display of a nitrilase provides an interesting new approach for immobilization of a multimeric enzyme on the surface of E. coli, which eliminates the need for costly enzyme preparations. With the production of 380 mg of pure (R)-mandelic acid the whole-cell biocatalyst showed its suitability for biocatalysis.

    4. Progress in Carbonylative-Heck Reactions of Aryl Bromides: Catalysis and DFT Studies (pages 726–733)

      Xiao-Feng Wu, Dr. Haijun Jiao, Dr. Helfried Neumann and Prof. Dr. Matthias Beller

      Version of Record online: 2 MAR 2011 | DOI: 10.1002/cctc.201000356

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      cHeck you out! A general and efficient palladium-catalyzed carbonylative Heck coupling reaction of aryl bromides with styrenes is described. In the presence of [{(cinnamyl)PdCl}2]/PPh3, 22 different chalcones have been synthesized in high yield.

    5. Highly Active Cobalt Oxide Catalysts Prepared by SACOP for the Preferential Oxidation of CO in Excess Hydrogen (pages 734–740)

      Dr. Irene López, Dr. Teresa Valdés-Solís and Dr. Gregorio Marbán

      Version of Record online: 3 FEB 2011 | DOI: 10.1002/cctc.201000351

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      Mitigating circumstances: The silica aquagel confined co-precipitation (SACOP) technique produces CoOOH of high specific surface area (up to 120 m2 g−1) that can be used as an extremely active catalyst under preferential oxidation (PROX) of residual CO conditions.

    6. Pore Structure and Surface Acidity Effects of Ordered Mesoporous Supports on Enantioselective Hydrogenation of Ethyl Pyruvate (pages 741–748)

      Stefan Böttcher, Claudia Hoffmann, Dr. Konstantin Räuchle and Prof. Dr. Wladimir Reschetilowski

      Version of Record online: 19 JAN 2011 | DOI: 10.1002/cctc.201000338

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      Had enough of a pore surface? Hydrogenation of ethyl pyruvate 1 (see scheme) is a model reaction in enantioselective heterogeneous catalysis. The effect of the support surface properties on the enantiodifferentiation is investigated by using Pt supported on a variety of ordered mesoporous silicas. The Pt/support catalysts gave enantioselectivities up to 94 % ee.

    7. Supported Ionic Liquid Phase Containing Palladium Nanoparticles on Functionalized Multiwalled Carbon Nanotubes: Catalytic Materials for Sequential Heck Coupling/Hydrogenation Process (pages 749–754)

      Dr. Laura Rodríguez-Pérez, Christian Pradel, Prof. Philippe Serp, Prof. Montserrat Gómez and Dr. Emmanuelle Teuma

      Version of Record online: 27 JAN 2011 | DOI: 10.1002/cctc.201000321

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      A smart bifunctional ligand leads to well-dispersed palladium nanoparticles in ionic liquid, which size remains unchanged upon immobilization on ionic functionalized multiwalled carbon nanotubes. This original heterogeneous system efficiently catalyzes a sequential Heck coupling/hydrogenation process, allowing its reuse.

    8. Gram-Scale Synthesis of Magnetically Separable and Recyclable Co@SiO2 Yolk-Shell Nanocatalysts for Phenoxycarbonylation Reactions (pages 755–760)

      Dr. Ji Chan Park, Hyun Ju Lee, Hyun Seok Jung, Mijong Kim, Dr. Hae Jin Kim, Prof. Kang Hyun Park and Prof. Hyunjoon Song

      Version of Record online: 27 DEC 2010 | DOI: 10.1002/cctc.201000318

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      What came first, the catalyst or the egg? Co@SiO2 yolk-shell nanocatalysts were synthesized by simple reduction of CoO@SiO2 core-shell nanoparticles without using an etching step (see figure). The catalysts exhibited high conversion efficiency and recyclability for the phenoxycarbonylation of iodobenzene.

    9. Effects of Acidity and Pore Size Constraints on Supported Niobium Oxide Catalysts for the Selective Formation of Glycerol Monolaurate (pages 761–770)

      Rajitha Radhakrishnan, Jiang Wu, Prof. Stephan Jaenicke and Prof. Gaik Khuan Chuah

      Version of Record online: 3 FEB 2011 | DOI: 10.1002/cctc.201000300

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      Green catalysts: A combination of suitable pore size and acidity in MCM-41-supported niobium oxides results in highly efficient solid-acid catalysts for esterification. Glycerol monolaurate, a useful surfactant used in cosmetics, pharmaceuticals, and food sectors, is formed with >90 % yield. These green catalysts are active in solventless esterification reactions of a variety of acids and alcohols and are easily recyclable.

    10. Oxidation of Polycyclic Aromatic Hydrocarbons with Hydrogen Peroxide in the Presence of Transition Metal Mono-Substituted Keggin-Type Polyoxometalates (pages 771–779)

      Dr. Ana C. Estrada, Dr. Mário M. Q. Simões, Dr. Isabel C. M. S. Santos, Prof. M. Graça P. M. S. Neves, Prof. José A. S. Cavaleiro and Prof. Ana M. V. Cavaleiro

      Version of Record online: 10 JAN 2011 | DOI: 10.1002/cctc.201000264

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      PAHs' Oxidation: The oxidation with hydrogen peroxide, in the presence of Fe and Mn substituted polyoxotungstates, of anthracene, naphthalene, 1-ethylnaphthalene, and 2-ethylnaphthalene has been studied. Anthracene has been selectively oxidized to 9,10-anthraquinone, with high conversion, whereas the oxidation of the ethylnaphthalenes occurs mainly at the alkyl substituent.

  10. Book Review

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Highlights
    9. Communications
    10. Full Papers
    11. Book Review
    12. Preview
    1. Catalysis without Precious Metals. Edited by R. Morris Bullock (page 780)

      Dr. Hans-Ulrich Blaser

      Version of Record online: 25 FEB 2011 | DOI: 10.1002/cctc.201000430

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      Wiley-VCH, Weinheim, 2010. 290 pp., Hardcover € 129.00—ISBN 978-3-527-32354-8

  11. Preview

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Highlights
    9. Communications
    10. Full Papers
    11. Book Review
    12. Preview
    1. You have free access to this content
      Preview: ChemCatChem 5/2011 (page 783)

      Version of Record online: 5 APR 2011 | DOI: 10.1002/cctc.201190017

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