ChemCatChem

Cover image for Vol. 4 Issue 8

August 2012

Volume 4, Issue 8

Pages 1021–1199

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireviews
    7. Highlight
    8. Conference Report
    9. Communications
    10. Full Papers
    11. Preview
    1. Cover Picture: Gold Nanoparticle-Catalyzed Formation of Nitrogen-containing Compounds—From Mechanistic Understanding to Synthetic Exploitation (ChemCatChem 8/2012) (page 1021)

      Jerrik Mielby, Søren Kegnæs and Prof. Peter Fristrup

      Article first published online: 2 AUG 2012 | DOI: 10.1002/cctc.201290030

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      One pot of catalysis at the end of the rainbow The cover picture shows a spectrum of nitrogen-containing compounds synthesized by supported gold nanoparticles. The Minireview by P. Fristrup et. al on p. 1037 ff. covers synthetic and mechanistic details of reactions including those of amines, and imine and amide syntheses. The benefits of gold-supported catalysis for these reactions include the absence of deactivation by N-adsorption, high activities and selectivities, and opportunities for tandem or one-pot reactions with simple catalyst recovery. The gold-catalyzed formation of nitrogen-containing compounds stands in excellent stead for further growth and improvement, for example in substrate scope, by increased mechanistic understanding. Research in this emerging field has boomed in recent years: could the road to industrial application be paved with gold?

    2. Cover Picture: Gold Nanoparticle-Catalyzed Formation of Nitrogen-containing Compounds—From Mechanistic Understanding to Synthetic Exploitation (ChemCatChem 8/2012) (page 1021)

      Jerrik Mielby, Søren Kegnæs and Prof. Peter Fristrup

      Article first published online: 27 JUL 2012 | DOI: 10.1002/cctc.201290026

      Thumbnail image of graphical abstract

      One pot of catalysis at the end of the rainbow The cover picture shows a spectrum of nitrogen-containing compounds synthesized by supported gold nanoparticles. The Minireview by P. Fristrup et. al on p. 1037 ff. covers synthetic and mechanistic details of reactions including those of amines, and imine and amide syntheses. The benefits of gold-supported catalysis for these reactions include the absence of deactivation by N-adsorption, high activities and selectivities, and opportunities for tandem or one-pot reactions with simple catalyst recovery. The gold-catalyzed formation of nitrogen-containing compounds stands in excellent stead for further growth and improvement, for example in substrate scope, by increased mechanistic understanding. Research in this emerging field has boomed in recent years: could the road to industrial application be paved with gold?

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireviews
    7. Highlight
    8. Conference Report
    9. Communications
    10. Full Papers
    11. Preview
    1. Graphical Abstract: ChemCatChem 8/2012 (pages 1023–1030)

      Article first published online: 27 JUL 2012 | DOI: 10.1002/cctc.201290027

  3. Corrigendum

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireviews
    7. Highlight
    8. Conference Report
    9. Communications
    10. Full Papers
    11. Preview
    1. You have free access to this content
      Corrigendum: Heterogeneous versus Homogeneous Palladium Catalysts for Cross-Coupling Reactions (page 1030)

      Dr. Mario Pagliaro, Dr. Valerica Pandarus, Dr. Rosaria Ciriminna, Dr. François Béland and Piera Demma Carà

      Article first published online: 27 JUL 2012 | DOI: 10.1002/cctc.201200410

      This article corrects:

      Heterogeneous versus Homogeneous Palladium Catalysts for Cross-Coupling Reactions

      Vol. 4, Issue 4, 432–445, Article first published online: 1 MAR 2012

  4. News

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireviews
    7. Highlight
    8. Conference Report
    9. Communications
    10. Full Papers
    11. Preview
  5. Minireviews

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireviews
    7. Highlight
    8. Conference Report
    9. Communications
    10. Full Papers
    11. Preview
    1. Gold Nanoparticle-Catalyzed Formation of Nitrogen-containing Compounds—From Mechanistic Understanding to Synthetic Exploitation (pages 1037–1047)

      Jerrik Mielby, Søren Kegnæs and Prof. Peter Fristrup

      Article first published online: 16 JUL 2012 | DOI: 10.1002/cctc.201200314

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      Don't be left out in the gold: Heterogeneous gold catalysis has recently been extended to nitrogencontaining compounds, which is a new and promising substrate class, as nitrogen is ubiquitous in both materials science and biology. This Minireview is meant to serve as an entry point for new researchers in this emerging field and is divided into sections based upon which nitrogen-containing products are synthesized using gold nanoparticles in the critical reaction step.

    2. How to Control the Selectivity of Palladium-based Catalysts in Hydrogenation Reactions: The Role of Subsurface Chemistry (pages 1048–1063)

      Dr. Marc Armbrüster, Dr. Malte Behrens, Dr. Fabrizio Cinquini, Dr. Karin Föttinger, Prof. Dr. Yuri Grin, Dr. Andreas Haghofer, Prof. Dr. Bernhard Klötzer, Dr. Axel Knop-Gericke, Harald Lorenz, Antje Ota, Dr. Simon Penner, Jan Prinz, Dr. Christoph Rameshan, Dr. Zsolt Révay, Dr. Dirk Rosenthal, Prof. Dr. Günther Rupprechter, Prof. Dr. Philippe Sautet, Prof. Dr. Robert Schlögl, Dr. Lidong Shao, Dr. László Szentmiklósi, Dr. Detre Teschner, Dr. Daniel Torres, Dr. Ronald Wagner, Roland Widmer and Gregor Wowsnick

      Article first published online: 22 JUN 2012 | DOI: 10.1002/cctc.201200100

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      Find the beauty on the inside: Recent work is reviewed that shows how the modification of Pd surfaces by incorporation of foreign species X in the sub-surface of Pd metal (X=H, C, Ga) can be developed into a design tool for hydrogenation catalyst development.

  6. Highlight

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireviews
    7. Highlight
    8. Conference Report
    9. Communications
    10. Full Papers
    11. Preview
    1. Chiral Acyclic Diaminocarbene Complexes: a New Opportunity for Gold Asymmetric Catalysis (pages 1065–1066)

      Dr. Marion Barbazanges and Prof. Louis Fensterbank

      Article first published online: 18 JUN 2012 | DOI: 10.1002/cctc.201200224

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      Lucky bag: Suitably substituted acyclic diaminocarbene (ADC) ligands were demonstrated to generate a chiral pocket around linear gold(I) complexes. These new catalysts were used to perform the very first catalytic enantioselective cycloisomerization/ acetalization tandem reaction.

  7. Conference Report

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireviews
    7. Highlight
    8. Conference Report
    9. Communications
    10. Full Papers
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    1. Weimar—The Place to be for Catalysis in Germany (pages 1068–1069)

      Dr. Marcus Rose and Dr. Stephan Enthaler

      Article first published online: 26 JUN 2012 | DOI: 10.1002/cctc.201200259

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      Weimar—The place to be: In March 2012, the German Catalysis Society held their annual meeting. Beside homogeneous and heterogeneous catalysis, more specialized topics such as photocatalysis, electrocatalysis, biomass valorization, as well as novel catalyst materials and in situ characterization techniques were represented.

  8. Communications

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireviews
    7. Highlight
    8. Conference Report
    9. Communications
    10. Full Papers
    11. Preview
    1. Development of an Immobilized Transaminase Capable of Operating in Organic Solvent (pages 1071–1074)

      Dr. Matthew D. Truppo, Hallena Strotman and Dr. Gregory Hughes

      Article first published online: 12 JUN 2012 | DOI: 10.1002/cctc.201200228

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      I′m stuck on you: The development of a highly active and stable immobilized transaminase capable of operating in organic solvent has been applied to the synthesis of various amines including Januvia (sitagliptin).

    2. Aminovinylidene: A Stable Surface Intermediate in the Dehydrogenation of Ethylamine on Pt(1 1 1) (pages 1075–1078)

      Dr. Iradwikanari Waluyo, Joel D. Krooswyk, Dr. Jun Yin, Yuan Ren and Prof. Michael Trenary

      Article first published online: 13 JUN 2012 | DOI: 10.1002/cctc.201200170

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      The midway point: The dehydrogenation of ethylamine on Pt(1 1 1) generates a stable surface intermediate, which was identified by reflection absorption infrared spectroscopy and density functional theory calculations as aminovinylidene. It is a novel surface species with a π-bond delocalized across its three atomic centers.

    3. Ternary Nanocomposites of Porphyrin, Angular Au Nanoparticles and Reduced Graphene Oxide: Photocatalytic Synthesis and Enhanced Photocurrent Generation (pages 1079–1083)

      Dr. Haiyan Li, Dr. Sen Liu, Jingqi Tian, Lei Wang, Wenbo Lu, Yonglan Luo, Prof. Abdullah M. Asiri, Abdulrahman O. Al-Youbi and Prof. Xuping Sun

      Article first published online: 4 JUN 2012 | DOI: 10.1002/cctc.201200128

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      A noble strategy: A photocatalytic strategy toward organic–inorganic ternary nanocomposites of Sn-porphyrin (SnP), angular Au nanoparticles (AuNPs), and reduced graphene oxide (RGO) using SnP as an effective photocatalyst for the reduction of both GO and AuIII under visible-light irradiation. The synergistic effect of surface plasmon resonance excitation in AuNPs and SnP leads to a 27-fold increase in the photocurrent.

    4. Highly Selective Sorbitol Hydrogenolysis to Liquid Alkanes over Ni/HZSM-5 Catalysts Modified with Pure Silica MCM-41 (pages 1084–1087)

      Dr. Qing Zhang, Dr. Ting Jiang, Dr. Bing Li, Prof. Tiejun Wang, Dr. Xinghua Zhang, Dr. Qi Zhang and Prof. Longlong Ma

      Article first published online: 4 JUN 2012 | DOI: 10.1002/cctc.201100508

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      I can afford to be picky: Liquid alkanes can be easily generated by the selective hydrogenolysis of sorbitol over the catalyst Ni/HZSM-5. An appropriate amount of added MCM-41 can distinctly modify the structural properties of HZSM-5 and, subsequently, influence the catalytic performance of the catalyst.

    5. Iron(0) Particles: Catalytic Hydrogenations and Spectroscopic Studies (pages 1088–1093)

      Alice Welther, Prof. Dr. Matthias Bauer, Dr. Matthias Mayer and Prof. Dr. Axel Jacobi von Wangelin

      Article first published online: 14 JUN 2012 | DOI: 10.1002/cctc.201100400

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      Ironing it out: The simple pre-catalyst system FeCl3/EtMgCl was applied to the hydrogenation of various alkenes and alkynes at room temperature. Domino iron-catalyzed allylation/hydrogenation reactions were performed under 1–4 bar H2. Spectroscopic studies determined the heterogeneous nature of the active catalyst species, its oxidation state (Fe0), and the local structure and size of the formed particles.

  9. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireviews
    7. Highlight
    8. Conference Report
    9. Communications
    10. Full Papers
    11. Preview
    1. Theoretical Study of Asymmetric Transfer Hydrogenation of Ketones Catalyzed by Amino Acid-Derived Rhodium Complexes (pages 1095–1104)

      Mikael Nordin, Dr. Rong-Zhen Liao, Dr. Katrin Ahlford, Prof. Hans Adolfsson and Prof. Fahmi Himo

      Article first published online: 24 APR 2012 | DOI: 10.1002/cctc.201200045

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      DFT outsourcing: DFT methodology is employed to reveal sources of enantioselectivity in the asymmetric transfer hydrogenation of ketones. The ligand binding mode, configuration of metal hydride intermediate, and a stabilizing CH–π interaction at the transition state are revealed.

    2. Simultaneous Generation of Mesoxalic Acid and Electricity from Glycerol on a Gold Anode Catalyst in Anion-Exchange Membrane Fuel Cells (pages 1105–1114)

      Le Xin, Zhiyong Zhang, Zhichao Wang and Prof. Wenzhen Li

      Article first published online: 22 MAY 2012 | DOI: 10.1002/cctc.201200017

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      Gold rush: The efficient cogeneration of mesoxalic acid (with a selectivity of 46 %) and electricity (with a peak power density of 57.9 mW cm−2 at 80 °C) has been achieved from the electrocatalytic oxidation of glycerol on an Aunanoparticle anode catalyst in anionexchange membrane fuel cells.

    3. Electrogenerated Polymers as Efficient and Robust Heterogeneous Catalysts for the Hydrolytic Kinetic Resolution of Terminal Epoxides (pages 1115–1121)

      Xiang Hong, Dr. Mohamed Mellah, Franck Bordier, Dr. Régis Guillot and Dr. Emmanuelle Schulz

      Article first published online: 13 MAY 2012 | DOI: 10.1002/cctc.201200085

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      An electrogenerated thiophene–salen–cobalt polymer, which was formed from a CoII complex in a CH2Cl2/AcOH/nBu4NBF4 electrolytic mixture, promoted the dynamic hydrolytic kinetic resolution of epibromohydrin into the expected bromoacetal in up to >99 % yield and 87 % ee. Conditions: X=OAc or BF4, 2 mol %, THF, RT, 48 h.

    4. Study on RuO2/SnO2: Novel and Active Catalysts for CO and CH4 Oxidation (pages 1122–1132)

      Jing Yu, Dr. Dan Zhao, Dr. Xianglan Xu, Prof. Dr. Xiang Wang and Prof. Dr. Ning Zhang

      Article first published online: 23 APR 2012 | DOI: 10.1002/cctc.201200038

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      A tale of two metal oxides: SnO2supported RuO2 catalysts are found to be very active and stable for CO and CH4 oxidation, owing to a synergetic effect between RuO2 and SnO2. RuO2 supported on uncalcined SnO2 is less active than if supported on calcined SnO2, owing to the possible formation of a new Ru[BOND]Sn[BOND]O compound, which weakens the synergetic effect.

    5. Dopamine-Modified Trititanate Nanotubes with UV- and Visible-Light Photocatalytic Activity: Coordinative Self-Assembly into a Recyclable Absorber (pages 1133–1138)

      Dr. Graham Dawson, Jinghai Liu, Dr. Luhua Lu and Prof. Wei Chen

      Article first published online: 19 APR 2012 | DOI: 10.1002/cctc.201200030

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      Clash of the trititanates: The search for a simple method to bestow trititanate nanotubes with visible-light activity for applications as solar-driven photocatalysts remains a challenge. Self-assembled-surface modification by dopamine imparted trititanate nanotubes with stable, recyclable photocatalytic activity under UV/Vis illumination. The controlled surface modification shifted the absorption onset into the visible region.

    6. Asymmetric aza-Diels–Alder and Cation–olefin Cyclization Sequence: a Concise Way to Fused Chiral Cyclopenta[b]piperidines (pages 1139–1142)

      Qing-Zhu Li, Lei Ma, Dr. Lin Dong and Prof. Dr. Ying-Chun Chen

      Article first published online: 4 APR 2012 | DOI: 10.1002/cctc.201200020

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      Aza buddies: A sequential asymmetric aza-Diels–Alder and cation–olefin reaction of 5-enals and N-Ts-1-aza-1,3-butadienes has been developed to construct fused cyclopenta[b]piperidine skeletons with moderate yields and excellent stereoselectivities (see scheme). 1)  amine (10 mol%), OFBA (10 mol%), MeCN/H2O, RT; 2)  TMSOTf (20 mol%), DCM, RT.

    7. Formation of Hierarchical Pore Structures in Zn/ZSM-5 to Improve the Catalyst Stability in the Aromatization of Branched Olefins (pages 1143–1153)

      Yeon Ho Kim, Prof. Kyung Hee Lee, Prof. Chang-Mo Nam and Prof. Jae Sung Lee

      Article first published online: 9 MAY 2012 | DOI: 10.1002/cctc.201200007

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      A maze of pores: The effect of hierarchical pore systems on the stability of the catalyst when the same amount of coke was formed on the external surface of the catalysts was investigated. Externally connected mesopores were not completely blocked by the coke.

    8. Promotion of PdCu/C Catalysts for Ethanol Oxidation in Alkaline Solution by SnO2 Modifier (pages 1154–1161)

      Prof. Kuan-Wen Wang, Wei-Da Kang, Dr. Yu-Chen Wei, Chen-Wei Liu, Pai-Cheng Su, Hung-Shuo Chen and Prof. Shu-Ru Chung

      Article first published online: 19 APR 2012 | DOI: 10.1002/cctc.201100500

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      Giving more than 100 %: In the presence of a PdSn phase and surface SnO2, the EOR activity of catalyst PdCuSn10 (10 wt % SnO2 addition) is enhanced to 230 % of that of PdCu/C, as evidenced by chronoamperometric measurements. This is attributable to the significant amount of PdSn phase in the bulk and SnO2 species on the surface, which enhance the CO oxidation ability and electrochemical surface area.

    9. Selective Catalytic Oxidation of Ammonia into Dinitrogen over a Zeolite-Supported Ruthenium Dioxide Catalyst (pages 1162–1166)

      Steven Heylen, Nele Delcour, Prof. Christine E. A. Kirschhock and Prof. Johan A. Martens

      Article first published online: 19 APR 2012 | DOI: 10.1002/cctc.201100489

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      Yay or Na-Y? Na-Y zeolite supported ruthenium dioxide is an excellent catalyst for the selective catalytic oxidation of NH3 into N2 at low temperatures.

    10. Key Amino Acid Residues for Reversed or Improved Enantiospecificity of an ω-Transaminase (pages 1167–1172)

      Dr. Maria Svedendahl Humble, Karim Engelmark Cassimjee, Dr. Vahak Abedi, Dr. Hans-Jürgen Federsel and Prof. Per Berglund

      Article first published online: 13 APR 2012 | DOI: 10.1002/cctc.201100487

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      Must be a rational explanation: By homology modeling, key amino acid residues in an ω-transaminase from Chromobacterium violaceum are rationally assigned. Variants with either improved enantiospecificity or reversed enantiomeric preference with E values >50 are achieved. One mutation improves the enantiospecificity up to 15-fold; two other mutations reverse the enantiopreference for 2-aminotetralin.

    11. Oxidative Cyanation of Tertiary Amines with Ethyl Cyanoformate over a Niobia-Supported Iron-Exchanged Molybdophosphoric Acid Catalyst (pages 1173–1178)

      Kasanneni Tirumala Venkateswara Rao, Bathula Haribabu, Dr. Potharaju S. Sai Prasad and Dr. Nakka Lingaiah

      Article first published online: 19 APR 2012 | DOI: 10.1002/cctc.201100478

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      Mo money, Mo problems: An efficient heterogeneous catalyst was used for the oxidative cyanation of tertiary amines with a less-toxic cyanide source. The catalyst was highly active and reusable without any loss in activity.

    12. The Kinetic Features of the Palladium-Catalyzed Hydrogenolysis of Nitriles and Amines (pages 1179–1184)

      Aaron J. Yap, Prof. Anthony F. Masters and Prof. Thomas Maschmeyer

      Article first published online: 30 MAR 2012 | DOI: 10.1002/cctc.201100472

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      An old friend revisited: A model of the kinetics underlying the hydrogenolysis of nitriles and amines, catalysed by Pd/C, has been derived. The kinetic features of these reactions were determined, enabling the investigation of the reasons behind the unusual preference for the continued hydrogenolysis observed under our mild conditions (80 °C, 1 atm H2).

    13. Evidence of Scrambling over Ruthenium-based Catalysts in Supercritical-water Gasification (pages 1185–1189)

      Dr. Andrew A. Peterson, Marian Dreher, Dr. Jörg Wambach, Dr. Maarten Nachtegaal, Prof. Søren Dahl, Prof. Jens K. Nørskov and Dr. Frédéric Vogel

      Article first published online: 4 JUN 2012 | DOI: 10.1002/cctc.201100450

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      Got to scramble eggs to make an omelet: Experimental evidence of scrambling confirms theoretical predictions that fully- and 3/4-substituted species (CD4 and CHD3) are preferentially formed from CH4 and supercritical D2O over Ru catalysts, providing insight into the catalytic mechanism.

    14. Vanadium Catalyzed Synthesis of Cyclic Organic Carbonates (pages 1190–1196)

      Alessia Coletti, Dr. Christopher J. Whiteoak, Prof. Dr. Valeria Conte and Prof. Dr. Arjan W. Kleij

      Article first published online: 13 APR 2012 | DOI: 10.1002/cctc.201100398

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      Somewhere over the vanadyl: The use of vanadyl complexes (as-synthesized and commercial) as (pre)catalysts for the formation of cyclic organic carbonates is described. The most active system in the series is linked with a decavanadate structure derived from [VO(acac)2] and is active under mild reaction conditions in this CO2 fixation process. The formation of this catalytically active polyoxometalate is supported by a range of analytical techniques.

  10. Preview

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireviews
    7. Highlight
    8. Conference Report
    9. Communications
    10. Full Papers
    11. Preview
    1. You have free access to this content
      Preview: ChemCatChem 9/2012 (page 1199)

      Article first published online: 27 JUL 2012 | DOI: 10.1002/cctc.201290029

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