ChemCatChem

Cover image for Vol. 5 Issue 10

October 2013

Volume 5, Issue 10

Pages 2729–3174

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Review
    7. Minireviews
    8. Highlights
    9. Communications
    10. Full Papers
    1. You have free access to this content
      Cover Picture: New Insights into the Oxidative Coupling of Methane from Spatially Resolved Concentration and Temperature Profiles (ChemCatChem 10/2013) (page 2729)

      Bahman Zohour, Daniel Noon and Prof. Dr. Selim Senkan

      Version of Record online: 1 OCT 2013 | DOI: 10.1002/cctc.201390048

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      Probing the fundamentals of oxidative coupling In their Communication on p. 2809 ff., B. Zohour, D. Noon, and S. Senkan reveal new insights into the oxidative coupling of methane. Spatial concentration profiles were measured in a La2O3/CeO nanofiber catalyst packed bed reactor using micro-capillary sampling coupled to on-line gas chromatography. These measurements revealed the early (i.e. prompt) formation of H2 in the oxidative coupling of methane (OCM) reaction, which has not been reported before. This discovery has important mechanistic implications for the development and refinement of fundamentally-based detailed chemical kinetic mechanisms (DCKM) for the OCM reaction. Once developed, DCKM are combined with the transport models for reactors to predict their behavior over a broad range of conditions, including conditions under which experimental data are not available or feasible. Consequently, DCKM play a vital role to evaluate different reactor configurations and process conditions, which are necessary to increase the yields for C2+ products, in order to bring the OCM process closer to commercial viability.

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      Inside Cover: Development of Mesoscopically Assembled Sulfated Zirconia Nanoparticles as Promising Heterogeneous and Recyclable Biodiesel Catalysts (ChemCatChem 10/2013) (page 2730)

      Dr. Swapan K. Das and Prof. Sherif A. El-Safty

      Version of Record online: 1 OCT 2013 | DOI: 10.1002/cctc.201390049

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      Biodiesel production for transportation The cover picture shows the use of a mesoscopic assembled zirconia nanoarchitecture as an effective catalyst in the biodiesel reaction. In their Full Paper on p. 3050 ff., S. A. El-Safty and S. K. Das report a simple fabrication of mesoscopic zirconia nanocatalysts. Owing to the open framework, large surface area, and the presence of ample acidic sites, the catalysts showed excellent catalytic activity in the biodiesel reaction for conversion of long-chain fatty acids to their methyl esters. The maximum biodiesel yield was ≈100%, even after multiple reuse cycles.

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      Back Cover: Simple and Efficient 1,3-Isomerization of Allylic Alcohols using a Supported Monomeric Vanadium-Oxide Catalyst (ChemCatChem 10/2013) (page 3176)

      Dr. Takato Mitsudome, Shoichiro Sueoka, Satoshi Ikeda, Dr. Tomoo Mizugaki, Prof. Dr. Koichiro Jitsukawa and Prof. Dr. Kiyotomi Kaneda

      Version of Record online: 1 OCT 2013 | DOI: 10.1002/cctc.201390052

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      Vanadium for victory The cover picture shows that an isolated monomeric vanadium-oxide species can promote the isomerization of allylic alcohols under liquid-phase conditions. In their Communication on p. 2879 ff., K. Kaneda et al. present the creation and characterization of the isolated monomeric vanadium species on silica surface (V/SiO2) and the high catalytic activity of V/SiO2 for various allylic alcohols, including under scaled-up and solvent-free reaction conditions. This heterogeneous catalyst also exhibits high reusability with no drop in activity. Our results highlight that the monomeric vanadium species plays a crucial role in the isomerization.

  2. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Review
    7. Minireviews
    8. Highlights
    9. Communications
    10. Full Papers
  3. Corrigendum

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Review
    7. Minireviews
    8. Highlights
    9. Communications
    10. Full Papers
    1. You have free access to this content
  4. News

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Review
    7. Minireviews
    8. Highlights
    9. Communications
    10. Full Papers
  5. Review

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Review
    7. Minireviews
    8. Highlights
    9. Communications
    10. Full Papers
    1. Terpene-Derived Bifunctional Thioureas in Asymmetric Organocatalysis (pages 2756–2773)

      Dr. Senthil Narayanaperumal, Prof. Daniel G. Rivera, Rodrigo C. Silva and Prof. Márcio W. Paixão

      Version of Record online: 15 APR 2013 | DOI: 10.1002/cctc.201200936

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      From pine resin to catalyst: The easily available rosin diterpene abietic acid has been transformed into a unique class of bifunctional thiourea catalysts that can also incorporate further substituents, thereby enabling either Lewis base or enamine activation modes. Their application in a wide range of stereoselective transformations has revealed the positive effect of this chiral and rigid skeleton on the catalytic performance of these hybrid thioureas.

  6. Minireviews

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Review
    7. Minireviews
    8. Highlights
    9. Communications
    10. Full Papers
    1. Powerful Amino Acid Derived Bifunctional Phosphine Catalysts Bearing a Hydrogen Bond Donor in Asymmetric Synthesis (pages 2775–2784)

      Prof. Dr. Li-Wen Xu

      Version of Record online: 21 MAY 2013 | DOI: 10.1002/cctc.201300198

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      Phosphines and hydrogen bonding are good collaborators! Air-stable α-amino acids or dipeptide derived chiral phosphines bearing hydrogen-bond-donating and silicon-based bulky groups are powerful and versatile catalysts for a range of enantioselective processes, including [3+2] and [4+2] cycloadditions, allylic alkylations, Morita–Baylis–Hillman reactions, and Michael addition reactions. They represent a class of novel, economical, and practical chiral phosphine-based organocatalysts.

    2. Binuclear Cooperative Catalysts for the Hydrogenation and Hydroformylation of Olefins (pages 2785–2793)

      Dr. Dennis G. H. Hetterscheid, Dr. Samir H. Chikkali, Prof. Dr. Bas de Bruin and Prof. Dr. Joost N. H. Reek

      Version of Record online: 16 APR 2013 | DOI: 10.1002/cctc.201300092

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      Let's cooperate! Cooperative bimetallic catalysis plays an important role in bioenzymatic conversions, and numerous examples are reported in (bio)inorganic and organic chemistry. In organometallic chemistry, this type of catalysis is rare. Here, the concept of cooperative binuclear substrate activation in hydrogenation and hydroformylation reactions is discussed.

  7. Highlights

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Review
    7. Minireviews
    8. Highlights
    9. Communications
    10. Full Papers
    1. Efficient, Low Temperature Production of Hydrogen from Methanol (pages 2795–2797)

      Dr.  J. Johan Verendel and Dr. Peter Dinér

      Version of Record online: 26 AUG 2013 | DOI: 10.1002/cctc.201300498

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      Loads of hydrogen! Two catalytic systems for homogeneous, low temperature, aqueous-phase methanol dehydrogenation are described. The catalysts are able to produce three molecules of hydrogen per methanol molecule and open opportunities for new developments in sustainable hydrogen production.

    2. Channel Crossing by a Catalytic Nanomotor (pages 2798–2801)

      Prof. Geoffrey A. Ozin

      Version of Record online: 1 JUL 2013 | DOI: 10.1002/cctc.201300426

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      Change the channel: Chemically powered sub-microscale motors that displayed translation and rotation motional dynamics have evolved to include function and utility that render them active for cargo transport and delivery, sensing, and chemotaxis.

    3. Understanding the Atomic-scale Process of Catalytic Assembly of Si Nanowires through Al Injection (pages 2802–2804)

      Jiaqing Wang, Prof. Xinming Li and Prof. Hongwei Gu

      Version of Record online: 26 AUG 2013 | DOI: 10.1002/cctc.201300392

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      Don′t get your nanowires crossed: Aluminum, as an attractive catalyst, has exhibited an effective doping behavior during silicon nanowire growth, in which Al can not only ensure a novel and efficient route to adjust Si nanowire compositions, but also plays a critical role in shaping the structural morphologies of Si nanowires. The fundamental understanding of the catalytic processes is crucial to the development of advanced silicon nanowire-based devices.

    4. Simple Organic Molecules as Catalysts for the Enantioselective Synthesis of Amines and Alcohols (pages 2805–2808)

      Dr. Yi Cui and Prof. Dr. Shū Kobayashi

      Version of Record online: 5 AUG 2013 | DOI: 10.1002/cctc.201300380

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      Valiant catalysis: Hoveyda et al. have developed a set of catalysts derived from valine for enantioselective syntheses. Reagents are inexpensive, allyl additions are scalable, harsh conditions are avoided, and reactions can be performed with 0.25 mol % catalyst in under 6 h at room temperature. The efficiency, economy, selectivity, and simplicity of the transformations and the range of boron reagents look to have sustained impact on future progress in amine and alcohol syntheses.

  8. Communications

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Review
    7. Minireviews
    8. Highlights
    9. Communications
    10. Full Papers
    1. New Insights into the Oxidative Coupling of Methane from Spatially Resolved Concentration and Temperature Profiles (pages 2809–2812)

      Bahman Zohour, Daniel Noon and Prof. Dr. Selim Senkan

      Version of Record online: 18 SEP 2013 | DOI: 10.1002/cctc.201300401

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      It's all about Methane: Comprehensive spatial species and temperature profiles are reported for an oxidative coupling of methane (OCM) fixed-bed reactor. Profiles presented at different CH4/O2 ratios provide important new information that is necessary for the refinement and rigorous validation of detailed chemical kinetic mechanisms for this process. The data reveal new insights into the kinetics and mechanism of the OCM reaction.

    2. A First-Principles DFT Study on the Active Sites of Pd-Cu-Clx/Al2O3 Catalyst for Low-Temperature CO Oxidation (pages 2813–2817)

      Changli Shen, Dr. Huiying Li, Jun Yu, Prof. Guisheng Wu, Prof. Dongsen Mao and Prof. Guanzhong Lu

      Version of Record online: 24 JUL 2013 | DOI: 10.1002/cctc.201300356

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      A tandem cycle ride: The catalytic reaction mechanism of CO oxidation over Pd-Cu-Clx/γ-Al2O3 is proposed based on DFT studies. There are two catalytic cycles in the CO oxidation process, the palladium cycle ( (green)) and the copper cycle ( (red)).

    3. Selective Hydrogenation of Alkynes Catalyzed by Trinuclear Rhodium Hydride Complexes of the Type [{(Rh[PP*]H)32-H)33-H)}(BF4)2] (pages 2818–2821)

      Christina Kohrt, Gerrit Wienhöfer, Cornelia Pribbenow, Prof. Dr. Matthias Beller and Prof. Dr. Detlef Heller

      Version of Record online: 19 JUL 2013 | DOI: 10.1002/cctc.201300328

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      A clean win: A novel trinuclear rhodium(III)-hydride species allows for highly selective hydrogenation of diarylacetylenes under mild conditions (1 bar of hydrogen pressure at 30.0 °C in methanol) with low catalyst loadings (substrate/catalyst molar ratio≤10 000). In contrast to the mononuclear complex of the type [{Rh(PP*)(MeOH)2}BF4], no overhydrogenation of the diphenylacetylene to the alkane is observed. The hydrogen consumption follows Michaelis–Menten kinetics.

    4. Immobilized Ru Clusters in Nanosized Mesoporous Zirconium Silica for the Aqueous Hydrogenation of Furan Derivatives at Room Temperature (pages 2822–2826)

      Jiazhi Chen, Dr. Fang Lu, Junjie Zhang, Weiqiang Yu, Prof. Feng Wang, Prof. Jin Gao and Prof. Jie Xu

      Version of Record online: 17 JUN 2013 | DOI: 10.1002/cctc.201300316

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      Ru lonesome tonight? Immobilized ruthenium clusters (50 Ru atoms) in nanosized mesoporous zirconium silica were synthesized by using an impregnation method starting from an aqueous solution of RuCl3. The Ru cluster catalysts were thermally stable at 500 °C and showed remarkable activity for the hydrogenation of furan derivatives in water at room temperature under 5 bar hydrogen pressure.

    5. Spatial Distribution of Zeolite ZSM-5 within Catalyst Bodies Affects Selectivity and Stability of Methanol-to-Hydrocarbons Conversion (pages 2827–2831)

      Dr. Pedro Castaño, Dr. Javier Ruiz-Martínez, Eva Epelde, Prof. Dr. Ana G. Gayubo and Prof. Dr. Bert M. Weckhuysen

      Version of Record online: 2 JUL 2013 | DOI: 10.1002/cctc.201300218

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      Implicated in the catalysis crime: The spatial distribution of zeolite ZSM-5 aggregates within industrial-like catalyst bodies has a vast impact on the methanol-to-olefin selectivity and overall stability of the catalyst. Catalyst bodies with smaller ZSM-5 aggregates yield more olefins, less paraffins, and significantly less coke than catalyst bodies containing less dispersed ZSM-5 crystals. This result has direct implications on the way catalysts are prepared and manufactured.

    6. Direct Synthesis of Amides from Carboxylic Acids and Amines by Using Heterogeneous Catalysts: Evidence of Surface Carboxylates as Activated Electrophilic Species (pages 2832–2834)

      Dr. Chiara Deiana, Dr. Yuriy Sakhno, Marco Fabbiani, Dr. Marco Pazzi, Prof. Marco Vincenti and Prof. Gianmario Martra

      Version of Record online: 1 JUL 2013 | DOI: 10.1002/cctc.201300164

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      Amide synthesis: In situ IR spectroscopy and HRMS provided evidence of the activation of surface carboxylates at mild temperatures (about 323 K) for the direct synthesis of amides from carboxylic acids and amines.

    7. A Widely Applicable Regioselective Aerobic α-Cyanation of Tertiary Amines Heterogeneously Catalyzed by Manganese Oxides (pages 2835–2838)

      Dr. Kazuya Yamaguchi, Dr. Ye Wang and Prof. Dr. Noritaka Mizuno

      Version of Record online: 23 JUL 2013 | DOI: 10.1002/cctc.201300477

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      A fit catalyst for some aerobic exercise: A manganese oxide-based octahedral molecular sieve, OMS-2, could act as an efficient heterogeneous catalyst for the regioselective α-cyanation of various tertiary amines, including trialkyl, benzylic, and N,N-dialkylaniline derivatives using trimethylsilyl cyanide (TMSCN) as the cyano source and molecular oxygen as the terminal oxidant.

    8. Palladium-Catalyzed C[BOND]H ortho Arylation of Benzoic Acids with Diaryliodonium Salts in Water (pages 2839–2842)

      Zhiqing Wu, Si Chen, Chenxu Hu, Dr. Zhengkai Li, Dr. Haifeng Xiang and Prof. Dr. Xiangge Zhou

      Version of Record online: 9 AUG 2013 | DOI: 10.1002/cctc.201300470

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      Get down with the func(tionalization): An efficient and practical protocol for the C[BOND]H ortho arylation of benzoic acids with diaryliodonium salts by using water as an environmentally benign, nontoxic reaction medium is developed. The choice of water as the solvent is crucial for this reaction, which sets the stage for the broad application of aqueous conditions in C[BOND]H functionalization reactions.

    9. The First Continuous Flow Hydrogenation of Amides to Amines (pages 2843–2847)

      Dr. Jacorien Coetzee, Dr. Haresh G. Manyar, Prof. Dr. Christopher Hardacre and Prof. Dr. David J. Cole-Hamilton

      Version of Record online: 19 AUG 2013 | DOI: 10.1002/cctc.201300431

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      Hydrogen goes with the flow: Conversion of amides into amines is usually achieved with stoichiometric amounts of metal hydrides, which generate large amounts of waste. Catalytic hydrogenation represents an environmentally benign alternative for this conversion, whereas flow catalysis allows catalyst separation and high throughput. Here, we combine amide hydrogenation and flow catalysis for the first time.

    10. A Highly Active Cationic Ruthenium Complex for Alkene Isomerisation: A Catalyst for the Synthesis of High Value Molecules (pages 2848–2851)

      Simone Manzini, Dr. David J. Nelson and Prof. Dr. Steven P. Nolan

      Version of Record online: 5 JUL 2013 | DOI: 10.1002/cctc.201300396

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      You′ve been valorized! A novel cationic ruthenium complex is shown to be efficient in the isomerization of important feedstocks derived from essential oils, which can then be functionalized through olefin metathesis.

    11. An Improved Method for the Complete Hydrogenation of Aromatic Compounds under 1 Bar H2 with Platinum Nanowires (pages 2852–2855)

      Tingting Yu, Jiaqing Wang, Prof. Xinming Li, Prof. Xueqin Cao and Prof. Hongwei Gu

      Version of Record online: 24 JUL 2013 | DOI: 10.1002/cctc.201300394

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      A little pressure for a lot of gain: An efficient method has been developed for the controlled hydrogenation of phenol using a platinum nanowire catalyst under mild conditions (>98.4 %, 1 atm H2, 60 °C). The catalyst also exhibited high levels of activity and selectivity towards other selected aromatic compounds bearing a variety of different substituents, demonstrating its generality towards the hydrogenation of aromatic compounds.

    12. Enantioselective Reduction of α-Cyano and α-Nitro Substituted Acetophenones Promoted by a Bifunctional Mesoporous Silica (pages 2856–2860)

      Boxin Deng, Tanyu Cheng, Meng Wu, Jinyu Wang and Prof. Guohua Liu

      Version of Record online: 28 JUN 2013 | DOI: 10.1002/cctc.201300340

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      Pores that put your reaction in a spin! A recoverable mesoporous silica exhibits excellent catalytic activity and enhanced enantioselectivity for the reduction of α-cyano and α-cyanoacetophenones that ascribes the synergistic effect of its phase-transfer functionalized cetyltrimethylammonium bromide and confined chiral organoiridium catalytic nature.

    13. Nickel-Catalysed Reductive Amination with Hydrosilanes (pages 2861–2864)

      Jianxia Zheng, Dr. Thierry Roisnel, Prof. Dr. Christophe Darcel and Dr. Jean-Baptiste Sortais

      Version of Record online: 24 JUL 2013 | DOI: 10.1002/cctc.201300338

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      That's just silyl! Selective nickel-catalyzed reductive amination of aldehydes under hydrosilylation conditions is achieved by using a one pot, two step procedure. By using an in situ-generated catalyst (5 mol %) from Ni(OAc)2 and tricyclohexylphosphine with tetramethyldisiloxane (TMDS) as the hydrosilane at 70 °C, the corresponding secondary amines were obtained in moderate to good isolated yields.

    14. Synthesis of Air-Stable and Recyclable CpCoI-Complexes (pages 2865–2868)

      Indre Thiel, Dr. Anke Spannenberg and Dr. Marko Hapke

      Version of Record online: 12 JUL 2013 | DOI: 10.1002/cctc.201300294

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      An open-air ligand concerto: Air-stable and recyclable CpCoI-complexes, which are active in the [2+2+2] cycloaddition reaction, are synthesized. The application of heteroleptic complexes with one electron-poor olefin and one phosphite ligand proved to be the superior catalysts to other ligand combinations with regard to activity and stability.

    15. Single-Crystalline-Phase Mo3VOx: An Efficient Catalyst for the Partial Oxidation of Acrolein to Acrylic Acid (pages 2869–2873)

      Assoc. Prof. Dr. Chen Chen, Nakatani Kosuke, Assist. Prof. Dr. Toru Murayama and Prof. Dr. Wataru Ueda

      Version of Record online: 21 JUN 2013 | DOI: 10.1002/cctc.201300268

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      Being single (crystalline): Four single-crystalline-phase Mo3VOx materials are utilized as catalysts for the partial oxidation of acrolein to acrylic acid. The crystalline structure has a clear effect on catalytic performance. Mo3VOx with a trigonal crystalline structure is the most efficient catalyst: 99.8 % conversion with 93.9 % selectivity for acrylic acid is obtained at a temperature (217.3 °C) much lower than that previously reported.

    16. Organic Structure Directing Agent-Free and Seed-Induced Synthesis of Enriched Intracrystal Mesoporous ZSM-5 Zeolite for Shape-Selective Reaction (pages 2874–2878)

      Hongbin Zhang, Kunshan Song, Lei Wang, Hongxia Zhang, Prof. Yahong Zhang and Prof. Yi Tang

      Version of Record online: 23 JUL 2013 | DOI: 10.1002/cctc.201300242

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      Sowing the seeds: A sub-micron single-crystal-like ZSM-5 catalyst with enriched intracrystal mesopores is synthesized through a facile organic structure-directing agent-free and seed-induced route. The special crystal structure leads to significantly improved catalytic activity, well-preserved shape selectivity, and slow deactivation in the isomerization of o-xylene to p-xylene.

    17. Simple and Efficient 1,3-Isomerization of Allylic Alcohols using a Supported Monomeric Vanadium-Oxide Catalyst (pages 2879–2882)

      Dr. Takato Mitsudome, Shoichiro Sueoka, Satoshi Ikeda, Dr. Tomoo Mizugaki, Prof. Dr. Koichiro Jitsukawa and Prof. Dr. Kiyotomi Kaneda

      Version of Record online: 14 JUN 2013 | DOI: 10.1002/cctc.201300200

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      Promotion by group high five: Silica-supported monomeric vanadium-oxide promoted the isomerization of various allylic alcohols, including under scaled-up and solvent-free reaction conditions. This catalyst also exhibited high reusability with no drop in activity.

    18. Asymmetric Aldol Reaction of Glyoxal Catalyzed by Diarylprolinol (pages 2883–2885)

      Prof. Dr. Yujiro Hayashi and Masahiro Kojima

      Version of Record online: 18 JUN 2013 | DOI: 10.1002/cctc.201300247

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      All selection should be this­ eeasy: The direct asymmetric aldol reaction of commercial aqueous glyoxal is catalyzed by trifluoromethyl-substituted diarylprolinol 1 to afford a β-formyl-β-hydroxy-α-substituted aldehyde in good yield with excellent anti selectivity and excellent enantioselectivity.

  9. Full Papers

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Review
    7. Minireviews
    8. Highlights
    9. Communications
    10. Full Papers
    1. Diarylprolinol in an Asymmetric, Direct Cross-Aldol Reaction with Alkynyl Aldehydes (pages 2887–2892)

      Prof. Dr. Yujiro Hayashi, Masahiro Kojima, Yusuke Yasui, Yuta Kanda, Takasuke Mukaiyama, Hiroki Shomura, Daichi Nakamura, Dr. Ritmaleni and Dr. Itaru Sato

      Version of Record online: 26 JUL 2013 | DOI: 10.1002/cctc.201300390

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      Reacts like a Pro: The asymmetric, direct cross-aldol reaction of alkynyl aldehydes catalyzed by a trifluoromethylated diarylprolinol provides a practical and highly enantioselective synthesis of chiral β-alkynyl-β-hydroxy aldehydes. Good anti selectivity and excellent enantioselectivity are obtained in the reactions of silylpropynals, which afford synthetically useful chiral building blocks.

    2. 1,2,3-Trimethoxypropane and Glycerol Ethers as Bio-Sourced Solvents from Glycerol. Synthesis by Solvent-Free Phase-Transfer Catalysis and Utilization as an Alternative Solvent in Chemical Transformations (pages 2893–2904)

      Marc Sutter, Dr. Wissam Dayoub, Dr. Estelle Métay, Dr. Yann Raoul and Prof. Marc Lemaire

      Version of Record online: 24 JUL 2013 | DOI: 10.1002/cctc.201300458

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      Bio-sourced sorcery: 1,2,3-Trimethoxypropane (1,2,3-TMP) was prepared in one step from glycerol in good yield and selectivity by phase-transfer catalysis. No solvent or heating were required and the process was adapted to a series of glycerol monoethers to afford a family of polar aprotic, glycerol-based solvents. 1,2,3-TMP was evaluated as a solvent in transesterifications, organometallic, and carbon–carbon coupling reactions.

    3. Direct Amination of Bio-Alcohols Using Ammonia (pages 2905–2912)

      Dr. Dennis Pingen, Dr. Olivier Diebolt and Prof. Dr. Dieter Vogt

      Version of Record online: 3 JUL 2013 | DOI: 10.1002/cctc.201300407

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      Alcohol or no alcohol? The presented catalytic system is able to selectively convert various bio-alcohols and diols to primary amines using ammonia. Parameter optimization showed the importance of ammonia concentration and Ru/P ratio. Single batches up to 4.5 g of substrates were converted in 99 % selectivity. The catalyst is very robust and can be re-used at least six times without significant loss of activity or selectivity.

    4. Electrosteric Activation by using Ion-Tagged Prolines: A Combined Experimental and Computational Investigation (pages 2913–2924)

      Prof. Andrea Bottoni, Prof. Marco Lombardo, Dr. Gian Pietro Miscione, Dr. Elisa Montroni, Dr. Arianna Quintavalla and Prof. Claudio Trombini

      Version of Record online: 15 AUG 2013 | DOI: 10.1002/cctc.201300399

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      Stack attack! The asymmetric aldol reaction between cyclohexanone and benzaldehyde in the presence of tagged 4-hydroxy-prolines is modeled to elucidate the empirical concept of electrosteric activation, introduced to account for the much higher activity of cis-ion-tagged prolines. A complex interplay of hydrogen bonds and π-stacking interactions is found to give rise to the observed enhanced activity.

    5. Regioselective Deacetylation of Disaccharides via Immobilized Aspergillus niger Esterase(s)-catalyzed Hydrolysis in Aqueous and Non-aqueous Media (pages 2925–2931)

      Dr. Teodora Bavaro, Dr. Pamela Torres-Salas, Nicola Antonioli, Dr. Carlo F. Morelli, Prof. Giovanna Speranza and Prof. Marco Terreni

      Version of Record online: 26 JUL 2013 | DOI: 10.1002/cctc.201300388

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      A deprotection racket: From Aspergillus niger lipase extract, a new esterase fraction was immobilized by covalent attachment on epoxy-acrylic resin. The obtained biocatalyst is able to catalyze regioselective deprotections of peracetylated β-methyl lactoside and β-methyl lactosaminide at the C-2 and C-3' positions, respectively.

    6. Palladium Supported Catalysts for Nitrocyclohexane Hydrogenation to Cyclohexanone Oxime with High Selectivity (pages 2932–2938)

      Prof. Ping-Le Liu, Hai-Ke Zhang, Si-Hua Liu, Zheng-Jie Yao, Dr. Fang Hao, Hong-Guang Liao, Dr. Kui-Yi You and Prof. He-An Luo

      Version of Record online: 24 JUL 2013 | DOI: 10.1002/cctc.201300377

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      Brilliance in the performance: Carbon nanotube-supported palladium catalysts demonstrate better catalytic performance than activated carbon-supported palladium catalysts in general because of their mesoporous structures, which are favorable supports for the accessibility of the reactants to the active sites and the product desorption from the catalyst.

    7. Bifunctional Iron Complexes: Efficient Catalysts for C[DOUBLE BOND]O and C[DOUBLE BOND]N Reduction in Water (pages 2939–2945)

      Delphine S. Mérel, Margaux Elie, Jean-François Lohier, Dr. Sylvain Gaillard and Prof. Jean-Luc Renaud

      Version of Record online: 17 JUN 2013 | DOI: 10.1002/cctc.201300325

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      Is this the iron age? Well-defined iron-complex-catalyzed reduction of aldehydes, ketones, and imines using molecular hydrogen in water is presented. Under mild conditions, good yields for a broad range of substrates are achieved.

    8. N,N-Diphospholylamines—A New Family of Ligands for Highly Active, Chromium-Based, Selective Ethene Oligomerisation Catalysts (pages 2946–2954)

      Tom E. Stennett, Dr. Thomas W. Hey, Liam T. Ball, Stephanie R. Flynn, James E. Radcliffe, Dr. Claire L. McMullin, Dr. Richard L. Wingad and Prof. Dr. Duncan F. Wass

      Version of Record online: 21 JUN 2013 | DOI: 10.1002/cctc.201300306

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      Top hole phosphole! New diphosphazane ligands based on phosphole donors produce highly active catalysts with chromium for the selective oligomerization of ethene. Modification of the backbone nitrogen substituent gives excellent control over the C6/C8 selectivity. MAO=methylaluminoxane.

    9. Ligand-Modified Rhodium Catalysts on Porous Silica in the Continuous Gas-Phase Hydroformylation of Short-Chain Alkenes–Catalytic Reaction in Liquid-Supported Aldol Products (pages 2955–2963)

      Andreas Schönweiz, Jonas Debuschewitz, Simon Walter, Dr. René Wölfel, Hanna Hahn, Katrin M. Dyballa, Prof. Dr. Robert Franke, Dr. Marco Haumann and Prof. Dr. Peter Wasserscheid

      Version of Record online: 16 AUG 2013 | DOI: 10.1002/cctc.201300305

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      It's all in the pores! Ligand-modified Rh complexes are physically adsorbed onto the surface of porous silica and the resulting solid materials are subjected to continuous gas-phase hydroformylation of C2 and C4 alkenes. The catalyst materials were surprisingly active and, in particular, exhibited similar selectivity to liquid-phase reactions.

    10. Carbon Nanofiber Supported Transition-Metal Carbide Catalysts for the Hydrodeoxygenation of Guaiacol (pages 2964–2972)

      Anna L. Jongerius, Robert W. Gosselink, Jelmer Dijkstra, Dr. Johannes H. Bitter, Dr. Pieter C. A. Bruijnincx and Prof. Bert M. Weckhuysen

      Version of Record online: 16 JUL 2013 | DOI: 10.1002/cctc.201300280

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      Get off O′Me: Hydrodeoxygenation of guaiacol over W2C and Mo2C supported on carbon nanofibers was studied. These catalysts display high activities and selectivities towards phenol and cresols in comparison to previously reported CoMo/Al2O3 catalysts. Catalyst recycling experiments showed that the Mo2C/CNF catalyst is stable under reaction conditions and can be reused without further treatment (CNF=carbon nanofiber).

    11. Plasmon-Enhanced Photocatalysis on Anisotropic Gold Nanorod Arrays (pages 2973–2977)

      Levent Kubus, Hakan Erdogan, Dr. S. Sebnem Cetin, Prof. Dr. Erhan Biskin and Prof. Dr. Gokhan Demirel

      Version of Record online: 14 JUN 2013 | DOI: 10.1002/cctc.201300279

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      A nanorod to guide the way: Directional gold nanorod arrays with optical anisotropy are fabricated through an oblique-angle deposition technique. By employing them as a plasmonic catalyst, we observe a clear improvement and control of the catalytic reduction of o-nitroaniline (o-NA) to 1,2-benzenediamine (BDA), depending on the directionalities and anisotropic plasmonic properties of the gold nanorods.

    12. Efficient Copper-Catalyzed Ullmann Reaction of Aryl Bromides with Imidazoles in Water Promoted by a pH-Responsive Ligand (pages 2978–2982)

      Rui Lv, Yangxin Wang, Dr. Chunshan Zhou, Dr. Liuyi Li and Prof. Ruihu Wang

      Version of Record online: 21 JUN 2013 | DOI: 10.1002/cctc.201300257

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      You can′t hold back the power of water: pH-Responsive 4,7-dihydroxy-1,10-phenanthroline exhibits an excellent promoting effect in copper-catalyzed Ullmann cross-coupling reaction of aryl bromides and imidazoles with different steric hindrance in neat water.

    13. Hydrogen Transfer Processes Mediated by Supported Iridium Oxide Nanoparticles (pages 2983–2990)

      Dr. Ceri Hammond, Martin T. Schümperli, Sabrina Conrad and Prof. Dr. Ive Hermans

      Version of Record online: 10 JUN 2013 | DOI: 10.1002/cctc.201300253

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      An idea in transit: Iridium oxide, supported on nanoparticulate cerium oxide, is reported to catalyze the oxidative dehydrogenation of alcohols via β-hydride elimination. The catalyst surface can be reoxidized with either a molecular oxygen or a ketone, which completes the transfer hydrogenation cycle.

    14. Recyclable Catalyst Reservoir: Oxidation of Alcohols Mediated by Noncovalently Supported Bis(imidazolium)-Tagged 2,2,6,6-Tetramethylpiperidine 1-Oxyl (pages 2991–2999)

      Hazi Ahmad Beejapur, Dr. Francesco Giacalone, Prof. Renato Noto, Dr. Paola Franchi, Prof. Marco Lucarini and Prof. Michelangelo Gruttadauria

      Version of Record online: 3 JUN 2013 | DOI: 10.1002/cctc.201300234

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      Catch and release: Why spend money on covalent immobilization or ionic liquids with bulky cations? A bis(imidazolium)-modified 2,2,6,6-tetramethylpiperidine 1-oxyl catalyst can be adsorbed on an imidazolium-modified support, then released in the presence of a proper organic solvent and recaptured at the end of the reaction on removal of the solvent.

    15. Metal–Organic Framework Supported Bimetallic Ni[BOND]Pt Nanoparticles as High-performance Catalysts for Hydrogen Generation from Hydrazine in Aqueous Solution (pages 3000–3004)

      Dr. Ashish Kumar Singh and Prof. Qiang Xu

      Version of Record online: 10 JUL 2013 | DOI: 10.1002/cctc.201300233

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      Highly dispersed bimetallic Ni[BOND]Pt nanoparticles with different Ni[BOND]Pt compositions have been successfully immobilized on the zeolitic metal–organic framework ZIF-8 by a simple liquid impregnation method, which show high catalytic activity and durability for hydrogen generation from decomposition of hydrazine in aqueous alkaline solution at 323 K.

    16. Addition of Sulfonic Acids to Terminal Alkynes Catalyzed by a Rhodium Complex: Ligand Concentration-Controlled Reaction Selectivity (pages 3005–3013)

      Dr. Yong Yang, Dr. Eric G. Moschetta and Prof. Robert M. Rioux

      Version of Record online: 8 AUG 2013 | DOI: 10.1002/cctc.201300228

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      Trying to concentrate: The concentration of the exogenous phosphine ligand in the Rh-catalyzed hydrosulfonation of alkynes with sulfonic acids controls the selectivity of the final products. High concentrations of ligand lead to the formation of vinylphosphonium salts, whereas low concentrations of ligand lead to the formation of vinyl sulfonate esters. cod=1,5-cyclooctadiene, DCE=1,2-dichloroethane.

    17. Versatile Pd-Catalyzed C[BOND]H Oxidative Cyclization of Homoallylhydrazones to Pyrazolines and Tetrahydropyridazines (pages 3014–3021)

      Cleve Dionel Mboyi, Dr. Ibrahim Abdellah, Carine Duhayon, Dr. Yves Canac and Prof. Remi Chauvin

      Version of Record online: 12 JUL 2013 | DOI: 10.1002/cctc.201300220

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      X marks the spot: Pd-catalyzed C[BOND]H oxidative cyclization of C-homoallyl-N-sulfonylhydrazones can follow two routes depending on the nature of the X ligand in the PdX2/BIPHIMIP system. If the ligand is an acetate (X=OAc), a 6-endo-trig process is favored to form 6-methylidene-1,4,5,6-tetrahydropyridazines, and if noncoordinating anions such tosylates and triflates (X=OTs, OTf) are present, a 5-exo-trig process affords 5-vinylpyrazolines.

    18. Heteropoly Acid Catalysts for the Synthesis of Fragrance Compounds from Biorenewables: Cycloaddition of Crotonaldehyde to Limonene, α-Pinene, and β-Pinene (pages 3022–3026)

      Vinícius V. Costa, Dr. Kelly A. da Silva Rocha, Rafaela A. Mesquita, Dr. Elena F. Kozhevnikova, Prof. Ivan V. Kozhevnikov and Prof. Elena V. Gusevskaya

      Version of Record online: 14 JUN 2013 | DOI: 10.1002/cctc.201300208

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      Low-cost and smells good! Widespread monoterpenes, which are cheap biomass-based substrates available from coniferous trees or citric fruits, can be transformed in fragrant polycyclic products through a simple catalytic process using heteropoly acid H3PW12O40 (HPW) and its cesium salt Cs0.5H0.5PW12O40 (CsPW) as efficient and environmentally benign heterogeneous catalysts.

    19. Expanding the Scope of Laccase-Mediator Systems (pages 3027–3032)

      Dr. Paul Könst, Dr. Selin Kara, Svenja Kochius, Dr. Dirk Holtmann, Prof. Dr. Isabel W. C. E. Arends, Dr. Roland Ludwig and Dr. Frank Hollmann

      Version of Record online: 3 JUL 2013 | DOI: 10.1002/cctc.201300205

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      Laccase gets a look-in: The laccase-mediator system (LMS) for the regeneration of oxidized nicotinamide co-factors is revisited to broaden the mediator scope. The LMS based on the laccase from Myceliophthora thermophila and acetosyringone is applied to promote the oxidation of glucose and the oxidative lactonization of 1,4-butanediol to the corresponding γ-butyrolactone.

    20. Ionically Tagged Ru–Alkylidenes for Metathesis Reactions under Biphasic Liquid–Liquid Conditions (pages 3033–3040)

      Benjamin Autenrieth, Felix Willig, Dominik Pursley, Stefan Naumann and Prof. Michael R. Buchmeiser

      Version of Record online: 14 JUN 2013 | DOI: 10.1002/cctc.201300199

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      Perfect for ionic liquids: Two new ionically tagged Ru–alkylidene complexes have been synthesized and successfully applied to various metathesis reactions under biphasic liquid–liquid conditions. Both catalysts have also performed well under supported liquid–liquid conditions.

    21. Hydrodeoxygenation of Guaiacol over Carbon-Supported Metal Catalysts (pages 3041–3049)

      Dr. Jie Chang, Dr. Tanate Danuthai, Silvia Dewiyanti, Dr. Chuan Wang and Dr. Armando Borgna

      Version of Record online: 2 JUL 2013 | DOI: 10.1002/cctc.201300096

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      Convert hard, strike oil: The hydrodeoxygenation of guaiacol, a model reaction for bio-oil upgrading, is investigated. Carbon-supported ruthenium and molybdenum catalysts show promising activity and selectivity, although the reaction occurs following different reaction pathways.

    22. Development of Mesoscopically Assembled Sulfated Zirconia Nanoparticles as Promising Heterogeneous and Recyclable Biodiesel Catalysts (pages 3050–3059)

      Dr. Swapan K. Das and Prof. Sherif A. El-Safty

      Version of Record online: 21 JUN 2013 | DOI: 10.1002/cctc.201300192

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      Fasten your nanoparticles! Monodisperse nanoparticles are used as building blocks for a mesoscopic ZrO2 nanoarchitecture by using the template as a fastening agent. Successive integration of the sulfate functionality into the porous framework makes the material a heterogeneous and recyclable catalyst for biodiesel production with a maximum biodiesel yield of 100 %.

    23. Reduced Graphene Oxide: Control of Water Miscibility, Conductivity, and Defects by Photocatalysis (pages 3060–3067)

      Dr. Jung-Ho Yun, Dr. Yun Hau Ng, Roong Jien Wong and Prof. Rose Amal

      Version of Record online: 10 JUL 2013 | DOI: 10.1002/cctc.201300419

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      A graphitic water baby: A TiO2-based photocatalytic reaction is demonstrated to synthesize water highly conductive pure reduced graphene oxide sheets with conductivity comparable to that of bulk graphite. Controlling water miscibility and conductivity of reduced graphene oxide are of great importance for various aqueous-solution based applications.

    24. A Copper Metal–Organic Framework as an Efficient and Recyclable Catalyst for the Oxidative Cross-Dehydrogenative Coupling of Phenols and Formamides (pages 3068–3077)

      Dr. Nam T. S. Phan, Tung T. Nguyen and Phuong H. L. Vu

      Version of Record online: 23 AUG 2013 | DOI: 10.1002/cctc.201300400

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      A perfect match: The crystalline porous metal–organic framework Cu2(BPDC)2(BPY) (BPDC=4,4′-biphenyldicarboxylate, BPY=4,4′-bipyridine) proves to be an efficient and reusable catalyst for the synthesis of organic carbamates through the copper-catalyzed cross-dehydrogenative coupling reaction of DMF with 2-substituted phenols.

    25. Highly Recyclable Self-Supported Chiral Catalysts for the Enantioselective α-Hydrazination of β-Ketoesters (pages 3078–3085)

      Maria Torres, Dr. Aline Maisse-François and Dr. Stéphane Bellemin-Laponnaz

      Version of Record online: 15 AUG 2013 | DOI: 10.1002/cctc.201300395

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      Support group: Multitopic bis(oxazoline)-based chiral ligands are used with copper to generate efficient catalysts for the enantioselective α-hydrazination of β-ketoesters. The catalysts are achieved through the aggregation of copper(II) ions with polytopic ligands. The formation of the metallopolymers has been studied by UV/Vis titrations and nonlinear effect experiments.

    26. Facile Synthesis of a Nanocrystalline Metal–Organic Framework Impregnated with a Phosphovanadomolybdate and Its Remarkable Catalytic Performance in Ultradeep Oxidative Desulfurization (pages 3086–3091)

      Yiwei Liu, Dr. Shumei Liu, Prof. Dr. Shuxia Liu, Dr. Dadong Liang, Shujun Li, Qun Tang, Xingquan Wang, Jun Miao, Dr. Zhan Shi and Prof. Dr. Zhiping Zheng

      Version of Record online: 10 JUL 2013 | DOI: 10.1002/cctc.201300378

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      MOF-encased POMS: Nanocrystalline catalysts (i.e., NENU-9N) consisting of polyoxometalates (POMs) encased by metal–organic frameworks (MOFs) are synthesized. The catalysts can preconcentrate organic substrates and are able to disperse in nonpolar media by using the aromatic ligands in the MOFs as hydrophobic groups. The catalysts exhibit excellent activity in the oxidative desulfurization of dibenzothiophene (DBT).

    27. One-Pot Multifunctional Catalysis with NNN-Pincer Zr-MOF: Zr Base Catalyzed Condensation with Rh-Catalyzed Hydrogenation (pages 3092–3100)

      Antonia M. Rasero-Almansa, Prof. Avelino Corma, Prof. Marta Iglesias and Prof. Félix Sánchez

      Version of Record online: 26 JUL 2013 | DOI: 10.1002/cctc.201300371

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      Preparation wins half the battle: Multifunctional catalysts based on Zr-based metal organic frameworks containing guest-accessible NNN-pincer groups have been prepared. The combination of acid, basic, and hydrogenation active sites leads to a hybrid material that behaves as a multifunctional Zr–base–transition metal catalyst for one-pot cascade condensation–hydrogenation reactions.

    28. A Catalyst for One-step Isoparaffin Production via Fischer–Tropsch Synthesis: Growth of a H-Mordenite Shell Encapsulating a Fused Iron Core (pages 3101–3106)

      Qihang Lin, Guohui Yang, Prof. Xiaonian Li, Yoshiharu Yoneyama, Prof. Huilin Wan and Prof. Noritatsu Tsubaki

      Version of Record online: 16 JUL 2013 | DOI: 10.1002/cctc.201300336

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      Capsule catalyst: A H-mordenite (HMOR) zeolite shell is directly synthesized, without an organic template, on a silicalite-1 coated fused iron catalyst. When applied to Fischer–Tropsch synthesis (FTS), the selectivity of the prepared capsule catalyst to middle isoparaffins is significantly better than a physical mixture catalyst.

    29. The Effect of Substituents in PNPN[BOND]H Ligands on Activity and Selectivity of a Chromium-Based Catalyst System for Highly Selective Ethylene Trimerization (pages 3107–3113)

      Stefan Heinig, Dr. Anina Wöhl, Dr. Wolfgang Müller, Dr. Mohammed H. Al-Hazmi, Dr. Bernd H. Müller, Dr. Normen Peulecke and Prof. Dr. Uwe Rosenthal

      Version of Record online: 19 JUL 2013 | DOI: 10.1002/cctc.201300324

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      A family competition between selected ligands with a PNPN[BOND]H motive turns out to be a neck-and-neck race. A highly selective trimerization catalyst for ethylene is optimized through fine-tuning of structural and electronic properties.

    30. Optimizing Nanoscale TiO2 for Adsorption-Enhanced Photocatalytic Degradation of Low-Concentration Air Pollutants (pages 3114–3123)

      Jinze Lyu, Prof. Lizhong Zhu and Prof. Clemens Burda

      Version of Record online: 12 AUG 2013 | DOI: 10.1002/cctc.201300308

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      Fight pollution! A comparison of the adsorption and photodegradation of gas phase toluene under realistic indoor air purification conditions with the nature of microporous amorphous TiO2 and mesoporous anatase catalysts

    31. Heterogeneous Silica-Supported Ruthenium Phosphine Catalysts for Selective Formic Acid Decomposition (pages 3124–3130)

      Weijia Gan, Prof. Paul J. Dyson and Prof. Gábor Laurenczy

      Version of Record online: 21 JUN 2013 | DOI: 10.1002/cctc.201300246

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      Good things come in threes: Heterogeneous RuII-mTPPTS (mTPPTS=meta-trisulfonated triphenylphosphine) catalysts are prepared from a RuII-mTPPTS complex and phosphine-modified mesoporous silica. The optimized system MCM41-Si-(CH2)2PPh2/Ru-mTPPTS selectively decomposes HCOOH into H2 and CO2. Activity and stabilities are comparable or superior to those of the homogeneous catalyst precursor: a turnover frequency of 2780 h−1 was obtained at 110 °C. No Ru leaching was detected after turnover numbers of 71 000.

    32. From Homogeneous to Heterogeneous Catalysis of the Three-Component Coupling of Oxysulfonyl Azides, Alkynes, and Amines (pages 3131–3138)

      Tao Yang, Hao Cui, Changhe Zhang, Prof. Li Zhang and Prof. Cheng-Yong Su

      Version of Record online: 5 JUL 2013 | DOI: 10.1002/cctc.201300241

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      Azide-ways manoeuver: Oxysulfonyl azide is developed for the formation of N-oxysulfonyl amidines. Three kinds of CuI catalysts are tested, which include CuI, Cu2I2(PDIN) without micropores, and Cu2I2(BTTP4) with micropores (PDIN=1,4-phenylene diisonicotinate, BTTP4=benzene-1,3,5-triyltriisonicotinate). Both homogeneous CuI and heterogeneous Cu2I2(BTTP4) are catalytically efficient and provide N-oxysulfonyl amidines in good yields.

    33. The Effect of Noncatalytic Cations on the Activity and Selectivity of Nickel-Exchanged X Zeolites for Propene Oligomerization (pages 3139–3147)

      Anton N. Mlinar, Otto C. Ho, Gerry G. Bong and Prof. Alexis T. Bell

      Version of Record online: 14 JUN 2013 | DOI: 10.1002/cctc.201300232

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      Give me some space! The presence of alkali metal and alkaline earth cations increases the available space within high aluminum content faujasite zeolites, which leads to higher propene oligomerization activity and increased branching in dimer products.

    34. Effect of Organic Capping Agents on Ruthenium-Nanoparticle-Catalyzed Aqueous-Phase Fischer–Tropsch Synthesis (pages 3148–3155)

      Dr. Xian-Yang Quek, Dr. Robert Pestman, Prof. Dr. Rutger A. van Santen and Prof. Dr. Emiel J. M. Hensen

      Version of Record online: 13 AUG 2013 | DOI: 10.1002/cctc.201300231

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      Captivating chemistry: The effect of capping agents on a carbon-nanofiber-supported Ru catalyst for the Fischer–Tropsch (FT) reaction was investigated. The activity depended on the strength of the interactions between the organic capping agent and the Ru particles. Kinetic data suggest that the FT mechanism was largely unaffected by the capping agents. The use of an apolar solvent increased the rate of formation of hydrocarbons, but not that of oxygenates.

    35. TUD-1-Encapsulated HY Zeolite: A New Hierarchical Microporous/Mesoporous Composite with Extraordinary Performance in Benzylation Reactions (pages 3156–3163)

      Dr. Mohamed S. Hamdy and Prof. Dr. Guido Mul

      Version of Record online: 12 AUG 2013 | DOI: 10.1002/cctc.201300457

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      Performance extraordinaire: HY/TUD-1 is a new hierarchical microporous/mesoporous composite that is easy to synthesize by adding HY zeolite to the synthesis mixture of TUD-1. This composite demonstrates higher activity and improved stability in the Friedel–Crafts benzylation of benzene than does HY zeolite.

    36. Mechanistic Study of the Oxidative Steam Reforming of EtOH on Rh(111): The Importance of the Oxygen Effect (pages 3164–3174)

      Cih-Ying Syu and Prof. Jeng-Han Wang

      Version of Record online: 2 JUL 2013 | DOI: 10.1002/cctc.201200964

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      On top form: Understanding the mechanism and oxygen effect in the catalytic oxidative steam reforming (OSR) of EtOH can help the design of better catalysts and control of the operational conditions for efficient and no-pollutant hydrogen production.

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