ChemCatChem

Cover image for Vol. 4 Issue 11

November 2012

Volume 4, Issue 11

Pages 1685–1861

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. News
    6. Concept
    7. Minireview
    8. Highlight
    9. Communications
    10. Full Papers
    1. You have free access to this content
      Cover Picture: Single-Phase Heterogeneous Pt3Sn Catalyst Synthesized by Room-Temperature Self-Assembly (ChemCatChem 11/2012) (page 1685)

      Dr. Malika Boualleg, Prof. Jean-Marie Basset, Dr. Jean-Pierre Candy, Dr. Valérie Caps, Dr. Jean-Claude Jumas, Dr. Sébastien Norsic, Dr. Elsje Alessandra Quadrelli, Laurent Veyre and Dr. Chloé Thieuleux

      Article first published online: 25 OCT 2012 | DOI: 10.1002/cctc.201290039

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      The buzz about nanoparticles! The cover picture represents well-dispersed single-phase Pt3Sn bimetallic alloy nanoparticles of 2.4 nm diameter inside the pores of a honeycomb-structured mesoporous silica. The resulting material is a well-defined heterogeneous catalyst for preferential CO oxidation in the presence of H2 (PROX catalysis). In their communication on p. 1729 ff., Chloé Thieuleux et al. show how to control by sol–gel approach the growth of the silica matrix around preformed single-phase Pt3Sn nanoparticles, and how to remove the template and the stabilizing ligand around the metallic nanoparticles, so that the resulting material is a well-defined catalytic material active in isobutane dehydrogenation and in low-temperature CO PROX catalyses.

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      Inside Cover: A Computational Investigation of the Catalytic Properties of Graphene Oxide: Exploring Mechanisms by using DFT Methods (ChemCatChem 11/2012) (page 1686)

      Prof. Dr. Danil W. Boukhvalov, Daniel R. Dreyer, Prof. Dr. Christopher W. Bielawski and Prof. Dr. Young-Woo Son

      Article first published online: 25 OCT 2012 | DOI: 10.1002/cctc.201290040

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      Graphene for Hard Graft The cover picture shows a scheme of the two-step oxidation process of 1-phenylethanol to acetophenone over a graphene oxide surface realized by migration of hydrogen atoms from molecule to catalyst with its partial reduction proposed from DFT calculations. In their full paper on p. 1844 ff., Danil W. Boukhvalov et al. report on their computational investigation of the catalytic properties of graphene oxide. They used the oxidation of benzyl alcohol to benzaldehyde as their model reaction.

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      Back Cover: Perovskite NaCeTi2O6-Supported Ni Catalysts for CH4 Steam Reforming (ChemCatChem 11/2012) (page 1864)

      Dr. Shenghong Zhang, Dr. Satoshi Muratsugu, Nozomu Ishiguro, Prof. Dr. Shin-ichi Ohkoshi and Dr. Mizuki Tada

      Article first published online: 25 OCT 2012 | DOI: 10.1002/cctc.201290043

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      Getting a Head of Steam (Reforming) The cover picture shows a perovskite NaCeTi2O6-supported Ni catalyst being used for the steam reforming of methane (SRM). In their full paper on p. 1783 ff., Shenghong Zhang, Mizuki Tada et al. describe their perovskite catalyst and suggest that its characteristic performance is related to its basic character and oxygen conducting behavior. They also postulated that the basicity and oxygen conducting behavior of NaCeTi2O6 could regulate the affinity to H2O and the deactivative oxidation of Ni, resulting in the preferable SRM performances on the Ni/NCT catalyst.

  2. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. News
    6. Concept
    7. Minireview
    8. Highlight
    9. Communications
    10. Full Papers
    1. Graphical Abstract: ChemCatChem 11/2012 (pages 1687–1697)

      Article first published online: 25 OCT 2012 | DOI: 10.1002/cctc.201290041

  3. Corrigenda

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    3. Graphical Abstract
    4. Corrigenda
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    1. You have free access to this content
      Corrigendum: Advances in the Catalytic Production of Valuable Levulinic Acid Derivatives (page 1695)

      Dr. Jun Zhang, Prof. ShuBin Wu, Prof. Bo Li and Dr. HongDan Zhang

      Article first published online: 25 OCT 2012 | DOI: 10.1002/cctc.201200634

      This article corrects:

      Advances in the Catalytic Production of Valuable Levulinic Acid Derivatives

      Vol. 4, Issue 9, 1230–1237, Article first published online: 22 JUN 2012

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      Corrigendum: Palladium(II)-Catalyzed Regioselective Ortho Arylation of sp2 C[BOND]H Bonds of N-Aryl-2-amino Pyridine Derivatives (page 1696)

      Dr. Moumita Koley, Navid Dastbaravardeh, Dr. Michael Schnürch and Prof. Dr. Marko D. Mihovilovic

      Article first published online: 26 SEP 2012 | DOI: 10.1002/cctc.201200621

      This article corrects:

      Palladium(II)-Catalyzed Regioselective Ortho Arylation of sp2 C[BOND]H Bonds of N-Aryl-2-amino Pyridine Derivatives

      Vol. 4, Issue 9, 1345–1352, Article first published online: 13 JUN 2012

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      Corrigendum: Mechanism of the Catalytic Oxidation of Glycerol on Polycrystalline Gold and Platinum Electrodes (page 1697)

      Youngkook Kwon, Klaas Jan P. Schouten and Prof. Marc T. M. Koper

      Article first published online: 17 SEP 2012 | DOI: 10.1002/cctc.201200548

      This article corrects:

      Mechanism of the Catalytic Oxidation of Glycerol on Polycrystalline Gold and Platinum Electrodes

      Vol. 3, Issue 7, 1176–1185, Article first published online: 27 MAY 2011

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  4. News

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    3. Graphical Abstract
    4. Corrigenda
    5. News
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  5. Concept

    1. Top of page
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    1. Recycling CO2? Computational Considerations of the Activation of CO2 with Homogeneous Transition Metal Catalysts (pages 1703–1712)

      Dr. Markus Drees, Dr. Mirza Cokoja and Prof. Dr. Fritz E. Kühn

      Article first published online: 10 AUG 2012 | DOI: 10.1002/cctc.201200145

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      CO2 all the way to the bank: This concept article highlights the efforts to elucidate the mechanisms of the activation of carbon dioxide with homogeneous transition metal catalysts by theoretical DFT methods.

  6. Minireview

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    4. Corrigenda
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    1. Recent Advances in Asymmetric Counteranion-directed Catalysis (ACDC) (pages 1713–1721)

      Eloah P. Ávila and Prof. Dr. Giovanni W. Amarante

      Article first published online: 25 SEP 2012 | DOI: 10.1002/cctc.201200422

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      Rockin′ the selective reactions: new asymmetric catalytic reactions based on new concepts are desired for use in the synthesis of chiral molecules. Recent uses of asymmetric counteraniondirected catalysis (ACDC) appear as excellent contributions towards asymmetric catalytic reactions with excellent enantioselectivities.

  7. Highlight

    1. Top of page
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    3. Graphical Abstract
    4. Corrigenda
    5. News
    6. Concept
    7. Minireview
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    9. Communications
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    1. Towards a Functional Model of the [FeFe]-Hydrogenase: Dihydrogen Oxidation (pages 1723–1724)

      Dr. Joseph A. Wright and Prof. Christopher J. Pickett

      Article first published online: 7 AUG 2012 | DOI: 10.1002/cctc.201200348

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      Hydrogen oxidation—irons do it, slowly: Camara and Rauchfuss have shown that dihydrogen can be oxidised by combining a {2Fe–2S} core, a basic amine group and an electron sink in the same molecule. This biomimetic approach turns over and may open the way for more active catalysts.

  8. Communications

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    10. Full Papers
    1. The Origin of the Activity of Amine-Functionalized Metal–Organic Frameworks in the Catalytic Synthesis of Cyclic Carbonates from Epoxide and CO2 (pages 1725–1728)

      Tristan Lescouet, Dr. Céline Chizallet and Dr. David Farrusseng

      Article first published online: 21 AUG 2012 | DOI: 10.1002/cctc.201200288

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      What a pair! MOF MIL-68(In)-NH2 was used to catalyze the synthesis of styrene carbonate from styrene oxide and CO2. Amine substitution on the linker of MIL-68(In) promotes the synthesis of cyclic carbonate from styrene epoxide and CO2. Ab initio calculations and in situ characterization indicate that ligand substitution has a larger impact through electronic effects on the Brønsted site than through CO2 activation.

    2. Single-Phase Heterogeneous Pt3Sn Catalyst Synthesized by Room-Temperature Self-Assembly (pages 1729–1732)

      Dr. Malika Boualleg, Prof. Jean-Marie Basset, Dr. Jean-Pierre Candy, Dr. Valérie Caps, Dr. Jean-Claude Jumas, Dr. Sébastien Norsic, Dr. Elsje Alessandra Quadrelli, Laurent Veyre and Dr. Chloé Thieuleux

      Article first published online: 31 AUG 2012 | DOI: 10.1002/cctc.201200276

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      The silica matrix revolutions: A single-phase bimetallic Pt3Sn catalyst, which was obtained by a “ship-in-a-bottle” synthesis of a mesoporous-silica matrix around single-phase preformed colloids, is very selective in the dehydrogenation of isobutane and very active in the low-temperature oxidation of CO under preferential oxidation conditions.

    3. Ruthenium-Catalyzed Carbonylation of ortho C[BOND]H Bonds in Arylacetamides: C[BOND]H Bond Activation Utilizing a Bidentate-Chelation System (pages 1733–1736)

      Kaname Shibata, Nao Hasegawa, Dr. Yoshiya Fukumoto and Prof. Naoto Chatani

      Article first published online: 28 AUG 2012 | DOI: 10.1002/cctc.201200352

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      Karma karma karma chelation: Direct carbonylation of C[BOND]H bonds in arylacetamides was achieved using a bidentate-chelation system. The use of 2-pyridynylmethyl amino moiety is essential for the reaction to proceed. For achieving an efficient reaction, the presence of both ethylene (for a hydrogen acceptor) and H2O (probably for an efficient generation of catalytic active species) are required.

    4. DNA-Mediated Palladium Nanoparticles as an Efficient Catalyst for Hydrogenation- and Suzuki–Miyaura Coupling Reactions (pages 1737–1740)

      Hisanori Itoh, Hironori Maeda, Shinya Yamada and Dr. Yoji Hori

      Article first published online: 23 SEP 2012 | DOI: 10.1002/cctc.201200351

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      Waste DNA gets a second life: A Pd/DNA catalyst, which was prepared by a facile method, has high activity for the selective hydrogenation of carbon[BOND]carbon triple bonds, carbon–carbon double bonds, and nitro groups, as well as for the Suzuki–Miyaura coupling reaction.

      Corrected by:

      Corrigendum: Corrigendum: DNA-Mediated Palladium Nanoparticles as an Efficient Catalyst for Hydrogenation- and Suzuki–Miyaura Coupling Reactions

      Vol. 5, Issue 1, 21, Article first published online: 23 DEC 2012

    5. Highly Stable, Recyclable Copper Nanoparticles as Catalysts for the Formation of C[BOND]N Bonds (pages 1741–1745)

      Bingfeng Chen, Dr. Fengbo Li, Zhijun Huang, Fei Xue, Tao Lu, Yin Yuan and Prof. Guoqing Yuan

      Article first published online: 2 AUG 2012 | DOI: 10.1002/cctc.201200312

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      Running with copper: 4-dimethylaminopryidine-stabilized Cu nanoparticles (DMAP-CuNPs) are used to catalyze the formation of C[BOND]N bonds. The catalytic reaction proceeds as in a homogeneous system, whereas, the catalyst can be separated and recycled as in heterogeneous catalysis. A five-run test demonstrates that DMAP-CuNPs have high stability and recyclability.

    6. Towards Artificial Photosynthesis of CO2-Neutral Fuel: Homogenous Catalysis of CO2-Selective Reduction to Methanol Initiated by Visible-Light-Driven Multi-Electron Collector (pages 1746–1750)

      Dr. Yong Na, Prof. Per Lincoln, Johan R. Johansson and Prof. Bengt Nordén

      Article first published online: 24 JUL 2012 | DOI: 10.1002/cctc.201200209

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      And there was light! Electrochemical studies demonstrated the activation of CO2 by two-electron-reduced ruthenium complex [(bpy)2Ru(Q)]2+ (1). The CO2-reduction cycle was initiated by complex 1 as a photoactive electron mediator. MeOH was afforded with good selectivity from the multicomponent system, which also consisted of cobalt catalyst [Co(NDS)2]2−, a primary alcohol as a co-catalyst, and ascorbic acid in aqueous solution.

  9. Full Papers

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. News
    6. Concept
    7. Minireview
    8. Highlight
    9. Communications
    10. Full Papers
    1. Carbon Dioxide Fixation by Cycloaddition with Epoxides, Catalyzed by Biomimetic Metalloporphyrins (pages 1752–1758)

      Dongsheng Bai, Shuhui Duan, Long Hai and Prof. Dr. Huanwang Jing

      Article first published online: 13 AUG 2012 | DOI: 10.1002/cctc.201200204

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      A healthy fixation: Several main group metalloporphyrin complexes are prepared and used in CO2 fixation in a “green” synthesis of cyclic carbonates from epoxides and CO2. The catalytic activity order of biomimetic metalloporphyrinoids was AlIII>MgII>SnIV>SnII, which is attributable to the Lewis acidity of the metal center.

    2. Ternary Polymer Composite of Graphene, Carbon Nitride, and Poly(3-hexylthiophene): an Efficient Photocatalyst (pages 1759–1763)

      Sandeep Gawande and Dr. Sanjay R. Thakare

      Article first published online: 10 AUG 2012 | DOI: 10.1002/cctc.201200277

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      A bolt into the blue: A ternary polymer composite of graphene, carbon nitride, and poly(3-hexylthiophene) (G-g-C3N4-P3HT) is synthesized and proves an effective photocatalyst for the degradation of methylene blue under visible light in water. The G-g-C3N4-P3HT composite photocatalyzes the rate of degradation of this model pollutant at a rate three times higher than that with a g-C3N4-P3HT composite and could be applied to the treatment of waste water.

    3. Ga-Pd/Ga2O3 Catalysts: The Role of Gallia Polymorphs, Intermetallic Compounds, and Pretreatment Conditions on Selectivity and Stability in Different Reactions (pages 1764–1775)

      Liandi Li, Dr. Bingsen Zhang, Dr. Edward Kunkes, Dr. Karin Föttinger, Dr. Marc Armbrüster, Dr. Dang Sheng Su, Dr. Wei Wei, Prof. Dr. Robert Schlögl and Dr. Malte Behrens

      Article first published online: 30 AUG 2012 | DOI: 10.1002/cctc.201200268

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      Pretty polymorph: Pd/Ga2O3 catalysts consisting of metallic nanoparticles on porous polymorphs of Ga2O3 (α-, β-, and γ-Ga2O3) are synthesized by co-precipitation of Pd and Ga. The effects of formation of Ga-Pd intermetallic compounds (IMCs) in methanol steam reforming, hydrogenation of acetylene, and methanol synthesis from CO and CO2 are studied. IMC formation promotes selectivity in the catalytic hydrogenation of C2H2 and CO2, but not of CO.

    4. Palladium-Catalyzed Carbonylation of Chloroacetates to Afford Malonates: Controlling the Selectivity of the Product in a Buffer (pages 1776–1782)

      Jianglin Hu, Qi Zhang, Zhenhong Guan, Prof. Dr. Yanlong Gu, Dr. Wanling Mo, Prof. Dr. Tao Li and Prof. Guangxing Li

      Article first published online: 12 JUL 2012 | DOI: 10.1002/cctc.201200245

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      A select few: Malonates were obtained in excellent yields and selectivities from the palladium-catalyzed carbonylation of chloroacetates in a weakly alkaline buffer solution without the formation of Pd black.

    5. Perovskite NaCeTi2O6-Supported Ni Catalysts for CH4 Steam Reforming (pages 1783–1790)

      Dr. Shenghong Zhang, Dr. Satoshi Muratsugu, Nozomu Ishiguro, Prof. Dr. Shin-ichi Ohkoshi and Dr. Mizuki Tada

      Article first published online: 13 AUG 2012 | DOI: 10.1002/cctc.201200239

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      Reform meets resistance: A perovskite NaCeTi2O6-supported Ni catalyst was found to be active for methane steam reforming reactions with a low H2O/CH4 ratio (1:1) and superior resistance to carbon deposition was observed on Ni/NaCeTi2O6 compared to Ni/CeO2.

    6. Total Hydrogenation of Furfural over a Silica-Supported Nickel Catalyst Prepared by the Reduction of a Nickel Nitrate Precursor (pages 1791–1797)

      Dr. Yoshinao Nakagawa, Hiroya Nakazawa, Dr. Hideo Watanabe and Prof. Dr. Keiichi Tomishige

      Article first published online: 16 JUL 2012 | DOI: 10.1002/cctc.201200218

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      Tiny one works: Silica-supported nickel nanoparticles that are approximately 3 nm in size are highly active in the gas-phase total hydrogenation of furfural to tetrahydrofurfuryl alcohol. Particles with a larger size are less active in the hydrogenation step of the furfuryl alcohol intermediate to tetrahydrofurfuryl alcohol.

    7. Pore Morphology Control of Mesostructured SO42−/ZrO2-Based Hybrid Catalysts Functionalized by Alkyl-Bridged Organosilica Moieties for Biodiesel Production From Non-Edible Oil (pages 1798–1807)

      Wei Li, Fengyan Ma, Fang Su, Ling Ma, Shengqu Zhang and Prof. Dr. Yihang Guo

      Article first published online: 10 JUL 2012 | DOI: 10.1002/cctc.201200199

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      Eruca! We struck biodiesel! SO42−/ZrO2-SiO2(Ph/Et) hybrid materials with different structural ordering and pore geometries are prepared. The different pore morphologies lead to materials with different porosities, which in turn influence the catalytic performance in the transesterification of Eruca sativa Gars. oil to produce biodiesel. FAMEs: fatty acid monoalkyl esters (e.g., methyl palmitin, methyl stearate, methyl oleate, and methyl linoleate).

    8. Ruthenium(IV)–Bis(methallyl) Complexes as UV-Latent Initiators for Ring-Opening Metathesis Polymerization (pages 1808–1812)

      Dr. Dongren Wang, Jörg Unold, Martina Bubrin, Wolfgang Frey, Prof. Wolfgang Kaim and Prof. Michael R. Buchmeiser

      Article first published online: 16 JUL 2012 | DOI: 10.1002/cctc.201200183

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      One ring to [Ru]le them all: The RuIV-based catalysts [Ru(η33-C10H16)Cl2(PPh3)] (1) and [Ru(η33-C10H16)(CF3COO)2(PPh3)] (3) were applied as photo-latent initiators in the ring-opening metathesis polymerization of norborn-2-ene.

    9. High-Surface-Area SiO2–ZrO2 Mixed Oxides as Catalysts for the Friedel–Crafts-Type Alkylation of Arenes with Alcohols and Tandem Cyclopropanation Reactions (pages 1813–1818)

      Dr. Helena Kaper, Karim Bouchmella, Prof. Dr. P. Hubert Mutin and Dr. Frédéric Goettmann

      Article first published online: 2 JUL 2012 | DOI: 10.1002/cctc.201200175

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      In the mix: High-surface-area ZrO2–SiO2 mixed oxides synthesized by using non-hydrolytic sol–gel chemistry show good catalytic activity for the Friedel–Crafts-alkylation reaction. The catalyst can also be used in a tandem intra-Friedel–Crafts-alkylation/trans-hydrogenation process for the synthesis of substituted cyclopropanes.

    10. Improved Photocatalytic Hydrogen Production by Structure Optimized Nonstoichiometric Y2Ti2O7 (pages 1819–1827)

      Oliver Merka, Prof. Dr. Detlef W. Bahnemann and Prof. Dr. Michael Wark

      Article first published online: 13 JUL 2012 | DOI: 10.1002/cctc.201200148

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      There be pyrochlores on the horizon: Cationic lattice distortion and interchange are reduced dramatically by increasing the Ti/Y ratio in the pyrochlore, Y2Ti2O7. The chemical composition changes from the “stuffed” pyrochlore Y2(Ti2−xYx)O7−0.5 x via (Y2−zTiz)(Ti2−zYz)O7 to Y2−vTi2O7−1.5 v. Reduced distortion results in exclusive occupation of the B-site by titanium, which greatly increases photocatalytic activity.

    11. A Simple Phosphine–Diolefin-Promoted Copper-Catalysed N-Arylation of Pyrazoles with (Hetero)aromatic Bromides: The Case of Chloroarenes Revisited (pages 1828–1835)

      Vincent Rampazzi, Dr. Alexandre Massard, Dr. Philippe Richard, Dr. Michel Picquet, Prof. Dr. Pierre Le Gendre and Prof. Dr. Jean-Cyrille Hierso

      Article first published online: 30 AUG 2012 | DOI: 10.1002/cctc.201200368

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      At the copper, coppercubana… A new phosphine–diolefin combined with CuI promotes the coupling of pyrazoles to aryl and heteroaryl C2- and C3-bromides with different functional groups to selectively produce pyridinyl- and pyrimidinyl-pyrazoles, and furyl-, thienyl-, and thiazolyl-substituted pyrazoles. Conversely, for activated chloroarenes, nucleophilic aromatic substitution is achieved without copper or ligand.

    12. Ru–Cd/Bentonite for the Partial Hydrogenation of Benzene: A Catalyst without Additives (pages 1836–1843)

      Weitao Wang, Dr. Huizhen Liu, Guodong Ding, Peng Zhang, Dr. Tianbin Wu, Prof. Dr. Tao Jiang and Prof. Dr. Buxing Han

      Article first published online: 16 JUL 2012 | DOI: 10.1002/cctc.201200272

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      Bento-nite box: Ru–Cd/bentonite catalysts that were prepared with environmentally benign clay were active, selective, and recyclable for the partial hydrogenation of benzene into cyclohexene without the need for any additives in the reaction system. Easy preparation √ ; Low cost √ ; Supported additive √

    13. A Computational Investigation of the Catalytic Properties of Graphene Oxide: Exploring Mechanisms by using DFT Methods (pages 1844–1849)

      Prof. Dr. Danil W. Boukhvalov, Daniel R. Dreyer, Prof. Dr. Christopher W. Bielawski and Prof. Dr. Young-Woo Son

      Article first published online: 13 JUL 2012 | DOI: 10.1002/cctc.201200210

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      Understanding carbocatalysts: A computational study is undertaken to elucidate the reaction mechanisms behind experimentally observed oxidations and hydrations catalyzed by graphene oxide. Functional group-free carbon materials, such as graphite, are calculated to have substantially higher reaction barriers, which indicates that the high chemical potential and rich functionality of GO are desirable for the observed reactivity.

    14. Electrode-driven Regioselective Oxidation of Cinnamyl Alcohol by use of Thin Biologically Active Chloroperoxidase Composite Films (pages 1850–1855)

      Haitao Tian, Shilei Mu, Prof. Hexing Li, Prof. Xiaqin Wu and Dr. Zhongqing Lu

      Article first published online: 7 AUG 2012 | DOI: 10.1002/cctc.201200172

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      A film worth watching: A composite film modified glassy carbon electrode comprising chitosan, chloroperoxidase, didodecyldimethylammonium bromide, and Nafion is used with in situ-generated H2O2 as a bio-electrocatalytic system for the oxidation of cinnamyl alcohol. A total cinnamyl alcohol yield of 51.8 % (cf. 7.6 % with the conventional biological system with equivalent enzyme consumption) and a total turnover number of 80 500 are achieved.

    15. Volcano Relations for Oxidation of Hydrogen Halides over Rutile Oxide Surfaces (pages 1856–1861)

      Dr. Anja Toftelund, Dr. Isabela C. Man, Dr. Heine A. Hansen, Dr. Frank Abild-Pedersen, Dr. Thomas Bligaard, Prof. Jan Rossmeisl and Dr. Felix Studt

      Article first published online: 20 JUL 2012 | DOI: 10.1002/cctc.201200140

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      An explosive relationship: DFT calculations are used to establish volcano relationships for the heterogeneously catalyzed oxidation of hydrogen halides over rutile oxide surfaces. RuO2 is found to be closest to the top for all three processes. The activity generally increases from chlorine to bromine to iodine.

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