ChemCatChem

Cover image for Vol. 4 Issue 9

September 2012

Volume 4, Issue 9

Pages 1201–1435

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Minireviews
    6. Highlight
    7. Communications
    8. Full Papers
    1. Cover Picture: On the Mechanism of Lewis Acid Catalyzed Glucose Transformations in Ionic Liquids (ChemCatChem 9/2012) (page 1201)

      Dr. Evgeny A. Pidko, Dr. Volkan Degirmenci and Prof. Dr. Emiel J. M. Hensen

      Version of Record online: 28 AUG 2012 | DOI: 10.1002/cctc.201290031

      Thumbnail image of graphical abstract

      Glucose Dehydration The cover picture shows that the distinctly different behavior of ionic liquid-mediated CrII, CuII, and FeII chlorides towards glucose conversion is determined at the stage of the initial coordination of the carbohydrate with the Lewis acidic catalytic complex. In the full paper on p. 1263 ff. E. A. Pidko, V. Degirmenci, and E. J. M. Hensen investigate the mechanism of Lewis acid-catalyzed glucose dehydration using DFT calculations complemented by catalytic experiments and in situ X-ray absorption spectroscopy. The unique ability of CrCl2 catalyst to selectively dehydrate glucose is related to the formation of a coordination complex with glucose that directs its isomerization to fructose. CuCl2 mainly promotes nonselective conversion routes initiated via the direct sugar deprotonation by the metal chloride complex, whereas coordination and activation of carbohydrates by FeCl2 are not possible. (Cover illustration: ICMS Animation Studio, TU/e)

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Minireviews
    6. Highlight
    7. Communications
    8. Full Papers
  3. News

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Minireviews
    6. Highlight
    7. Communications
    8. Full Papers
  4. Minireviews

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Minireviews
    6. Highlight
    7. Communications
    8. Full Papers
    1. Click Chemistry of Alkyne–Azide Cycloaddition using Nanostructured Copper Catalysts (pages 1217–1229)

      Prof. Dr. Tienan Jin, Mei Yan and Prof. Dr. Yoshinori Yamamoto

      Version of Record online: 7 AUG 2012 | DOI: 10.1002/cctc.201200193

      Thumbnail image of graphical abstract

      An opportunity to click: The increasing advances in nanotechnology offer new opportunities to design and synthesize “green”, efficient and sustainable nanostructured catalyst systems. This Minireview describes the recent advances of supported copper nanoparticles and new nanoporous copper catalysts on the click reaction of alkyne–azide cycloaddition.

    2. Advances in the Catalytic Production of Valuable Levulinic Acid Derivatives (pages 1230–1237)

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

      Version of Record online: 22 JUN 2012 | DOI: 10.1002/cctc.201200113

      Thumbnail image of graphical abstract

      Value-added biorefining: Levulinic acid can be used as a platform chemical for the production of a wide range of value-added compounds, such as levulinate esters and γ-valerolactone. This review mainly discusses the catalytic routes for synthesis of valuable levulinate esters and γ-valerolactone from biomass under different reaction systems.

      Corrected by:

      Corrigendum: Corrigendum: Advances in the Catalytic Production of Valuable Levulinic Acid Derivatives

      Vol. 4, Issue 11, 1695, Version of Record online: 25 OCT 2012

  5. Highlight

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Minireviews
    6. Highlight
    7. Communications
    8. Full Papers
    1. Understanding Nature—Towards the Enzymatic Degradation of Cellulose with Monooxygenases (pages 1239–1240)

      Katharina Neufeld and Prof. Jörg Pietruszka

      Version of Record online: 16 JUL 2012 | DOI: 10.1002/cctc.201200287

      Thumbnail image of graphical abstract

      Having a productive breakdown: Elucidation of a novel and promising enzymatic activity of polysaccharide degrading enzymes opens new directions for the development of an efficient biorefinery. Polysaccharide monooxygenases (PMOs) use oxidative biocatalysis for cleaving glycosidic bonds in crystalline cellulosic biomaterial, thereby synergistically enhancing the action of hydrolytic counterparts.

  6. Communications

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Minireviews
    6. Highlight
    7. Communications
    8. Full Papers
    1. Low-Temperature Chemoselective Gold-Surface-Mediated Hydrogenation of Acetone and Propionaldehyde (pages 1241–1244)

      Ming Pan, Dr. Zachary D. Pozun, Adrian J. Brush, Prof. Graeme Henkelman and Prof.  C. Buddie Mullins

      Version of Record online: 17 JUL 2012 | DOI: 10.1002/cctc.201200311

      Thumbnail image of graphical abstract

      A golden opportunity: Chemoselective reactivity for the hydrogenation of acetone and propionaldehyde on H-covered gold is described. Propionaldehyde forms 1-propanol, whereas no hydrogenated product is detected from the interaction between acetone and hydrogen. Dissimilar energetic barriers and the polymerization of CH3CH2CHO are the basis of the chemoselective activity.

    2. Design of a Cobalt–Zeolite Catalyst for Semi-Linear Higher-Olefin Synthesis (pages 1245–1248)

      Dr. Joris Franken, Prof. Christine E. A. Kirschhock, Dr. Georges M. Mathys and Prof. Dr. Johan A. Martens

      Version of Record online: 20 JUL 2012 | DOI: 10.1002/cctc.201200267

      Thumbnail image of graphical abstract

      The tide is higher: Improved knowledge of the cation sites inside zeolite materials has led to the development of a tailor-made Co-based heterogeneous catalyst for the oligomerization of short olefins into semi-linear higher olefins.

    3. Reductive Amination of Ketones or Amination of Alcohols over Heterogeneous Cu Catalysts: Matching the Catalyst Support with the N-Alkylating Agent (pages 1249–1254)

      Federica Santoro, Rinaldo Psaro, Dr. Nicoletta Ravasio and Dr. Federica Zaccheria

      Version of Record online: 13 JUL 2012 | DOI: 10.1002/cctc.201200213

      Thumbnail image of graphical abstract

      The perfect match: Supported Cu catalysts can be used for the synthesis of aromatic secondary amines. The choice of catalyst support is tunable according to the alkylating agent that is used.

    4. An Autocatalytic Factor in the Loss of Efficiency in Dye-Sensitized Solar Cells (pages 1255–1258)

      Mingxing Wu, Yudi Wang, Xiao Lin, Prof. Anders Hagfeldt and Prof. Tingli Ma

      Version of Record online: 29 JUN 2012 | DOI: 10.1002/cctc.201200061

      Thumbnail image of graphical abstract

      The X-factor: The autocatalytic activity of some semiconductor oxides is a key factor behind the loss of efficiency in their dye-sensitized solar cells.

    5. Directed Evolution of the Enzyme Monoamine Oxidase (MAO-N): Highly Efficient Chemo-enzymatic Deracemisation of the Alkaloid (±)-Crispine A (pages 1259–1261)

      Dr. Ian Rowles, Dr. Kirk J. Malone, Dr. Laura L. Etchells, Dr. Simon C. Willies and Prof. Nicholas J. Turner

      Version of Record online: 16 JUL 2012 | DOI: 10.1002/cctc.201200202

      Thumbnail image of graphical abstract

      Crispine, at the double! Modification of the active site of the enzyme monoamine oxidase (MAO-N) allows the efficient deracemisation of the alkaloid crispine A. Microwave-enhanced chemical synthesis results in the rapid production of the racemic compound. Combining both techniques greatly shortens the time required for the synthesis of (R)-crispine A.

  7. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Minireviews
    6. Highlight
    7. Communications
    8. Full Papers
    1. On the Mechanism of Lewis Acid Catalyzed Glucose Transformations in Ionic Liquids (pages 1263–1271)

      Dr. Evgeny A. Pidko, Dr. Volkan Degirmenci and Prof. Dr. Emiel J. M. Hensen

      Version of Record online: 18 APR 2012 | DOI: 10.1002/cctc.201200111

      Thumbnail image of graphical abstract

      The pathfinders: The catalytic activity of ionic liquid-mediated CrII, CuII, and FeII chlorides in ionic liquids is controlled by their behavior toward the initial glucose coordination. The direct interaction of the sugar with the metal center (path I) results in the selective conversion to HMF. Alternatively, non-selective paths are initiated by the direct glucose deprotonation by a free metal chloride complex (path II).

    2. Phase-switching Homogeneous Catalysis for Clean Production of Biodiesel and Glycerol from Soybean and Microbial Lipids (pages 1272–1278)

      Xuefeng Cao, Prof. Haibo Xie, Zhilian Wu, Hongwei Shen and Prof. Bo Jing

      Version of Record online: 4 JUN 2012 | DOI: 10.1002/cctc.201200150

      Thumbnail image of graphical abstract

      Switch on and separate out: By using a range of “switchable solvents” from 1,8-diazabicyclo[5.4.0] undec-7-ene to methanol, CO2, a recognized greenhouse gas, can be used as a trigger to catalyze the methanolysis of soybean and microbial lipids, and facilitate the separation of fatty acid methyl esters and glycerol, in a good yield and purity.

    3. Rational Co-Immobilization of Bi-Enzyme Cascades on Porous Supports and their Applications in Bio-Redox Reactions with In Situ Recycling of Soluble Cofactors (pages 1279–1288)

      Javier Rocha-Martín, Blanca de las Rivas, Rosario Muñoz, Prof. José M Guisán and Dr. Fernando López-Gallego

      Version of Record online: 15 JUN 2012 | DOI: 10.1002/cctc.201200146

      Thumbnail image of graphical abstract

      Better together: Co-immobilization was used to assemble three bio-redox orthogonal cascades with in situ cofactor-regeneration. These procedures were more efficient than if the dehydrogenases were immobilized on different carriers.

    4. Isomerization and Dimerization of Pinene using Al-Incorporated MCM-41 Mesoporous Materials (pages 1289–1297)

      Prof. Ji-Jun Zou, Na Chang, Prof. Xiangwen Zhang and Prof. Li Wang

      Version of Record online: 22 MAY 2012 | DOI: 10.1002/cctc.201200106

      Thumbnail image of graphical abstract

      An aluminating approach: Aluminum-incorporated MCM-41 synthesized by a hydrothermal method is highly active for the isomerization and dimerization of pinene. Both α- and β-pinenes are isomerized before coupling to form homo- and heterodimers. The yield of dimer is closely related to the concentration of acid sites and the ordered mesoporous structure.

    5. Rhodium(I) Complexes with Hemilabile Phosphines: Rational Design for Efficient Oxidative Amination Catalysts (pages 1298–1310)

      Dr. M. Victoria Jiménez, Dr. M. Isabel Bartolomé, Prof. Dr. Jesús J. Pérez-Torrente, Prof. Dr. Fernando J. Lahoz and Prof. Dr. Luis A. Oro

      Version of Record online: 29 MAY 2012 | DOI: 10.1002/cctc.201200101

      Thumbnail image of graphical abstract

      Hemilabile ligands at work: Rhodium(I) catalysts that were based on P,O-functionalized ligands with a 3-ethoxy-propyl hemilabile moiety allowed the attainment of unprecedented turnover frequencies (up to 80 h−1) and excellent selectivity in the catalytic anti-Markovnikov oxidative amination of styrene with piperidine to afford enamine (E)-1-styrylpiperidine (96 %).

    6. DFT Study of Steam Reforming of Formaldehyde on Cu, PdZn, and Ir (pages 1311–1320)

      Xiang Li and Prof. Kok Hwa Lim

      Version of Record online: 25 MAY 2012 | DOI: 10.1002/cctc.201200028

      Thumbnail image of graphical abstract

      The energy to preserve us: The binding and reaction energies of formaldehyde steam reforming on Cu (1 0 0), Cu (2 2 1), PdZn (1 0 0), and Ir (1 0 0) surfaces are calculated. Adsorption complexes (e.g., CH2O, H2COOH, H2COO, HCOO, COOH) in formaldehyde steam reforming and dehydrogenation are characterized. Competition with desorption varies, depending on the nature and regularity of the surface sites.

    7. Pseudo-C2-Symmetric Bimetallic Bissalen Catalysts for Efficient and Enantioselective Ring-Opening of meso-Epoxides (pages 1321–1329)

      Dr. Da-You Ma, Dr. Ze-Yun Xiao, Julen Etxabe and Prof. Kenneth Wärnmark

      Version of Record online: 8 JUN 2012 | DOI: 10.1002/cctc.201200018

      Thumbnail image of graphical abstract

      Stapler catalysts: Hetero- and homobimetallic bissalen complexes based on Jacobsen's bissalen ligand motif are used as catalysts in the asymmetric ring-opening of mesoepoxides by TMSN3. The former are the first examples of pseudo-C2-symmetric complexes, owing to the presence of two different metal ions. They afford ring-opened products with the highest ee values to date in excellent yields. A proposed activation mode of the catalyst, used neat at loadings as low as 0.01 mol % at RT, is shown.

    8. Significant Formation of Adipic Acid by Direct Oxidation of Cyclohexane Using Supported Nano-Gold Catalysts (pages 1330–1336)

      Dr. Ahmad Alshammari, Dr. Angela Koeckritz, Dr. Venkata Narayana Kalevaru, Dr. Abdulaziz Bagabas and Dr. Andreas Martin

      Version of Record online: 23 JUL 2012 | DOI: 10.1002/cctc.201200008

      Thumbnail image of graphical abstract

      One step for adipic acid: The one-step synthesis of adipic acid from cyclohexane was achieved over supported nano-gold catalysts using a “green” route (Xcyclohexane>25 %, Sadipic acid>25 %, and SKA oil=70 %). Moreover, good correlations between Au particle size, surface composition, and catalytic activity were established.

    9. The Effects of SCILL Catalyst Modification on the Competitive Hydrogenation of 1-Octyne and 1,7-Octadiene versus 1-Octene (pages 1337–1344)

      Stuart F. Miller, Prof. Holger B. Friedrich and Prof. Cedric W. Holzapfel

      Version of Record online: 10 JUL 2012 | DOI: 10.1002/cctc.201100482

      Thumbnail image of graphical abstract

      A SCILLed approach: Solid catalysts with an ionic layer liquid (SCILL) have been applied to the competitive hydrogenation of 1-octyne and 1,7-octadiene under trickle bed conditions. The results highlight the importance of potential site-specific interactions by the ionic liquid. They also indicate the importance of the cation for these effects.

    10. You have full text access to this OnlineOpen article
      Palladium(II)-Catalyzed Regioselective Ortho Arylation of sp2 C[BOND]H Bonds of N-Aryl-2-amino Pyridine Derivatives (pages 1345–1352)

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

      Version of Record online: 13 JUN 2012 | DOI: 10.1002/cctc.201200155

      Thumbnail image of graphical abstract

      Anilinate, anilinate! A method for arylation of anilines directed by an N-2-pyridyl group is developed. The reaction is tolerant towards a large number of substituents on both the aniline and the boronic acid, which is used as aryl donor. Although often considered a permanent directing group, the pyridine group is removed efficiently to give ortho-arylated aniline derivatives.

      Corrected by:

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

      Vol. 4, Issue 11, 1696, Version of Record online: 26 SEP 2012

    11. Enhanced Interfacial Charge Transfer and Visible Photocatalytic Activity for Hydrogen Evolution from a Ta2O5-based Mesoporous Composite by the Incorporation of Quantum-Sized CdS (pages 1353–1359)

      Dr. Leilei Xu, Prof. Jianguo Guan and Dr. Weidong Shi

      Version of Record online: 15 JUN 2012 | DOI: 10.1002/cctc.201200137

      Thumbnail image of graphical abstract

      Ta Ta for now: Ordered mesoporous Ta2O5, sensitized with quantum-sized CdS, exhibits enhanced visible-light-driven photocatalytic activity for hydrogen evolution from simulant waste water that contains methylene blue in the absence of any co-catalysts.

    12. Samarium-exchanged Heteropoly Tungstate: An Efficient Solid Acid Catalyst for the Synthesis of Glycerol Carbonate from Glycerol and Benzylation of Anisole (pages 1360–1367)

      Ch. Ramesh Kumar, K. Jagadeeswaraiah, Dr. P. S. Sai Prasad and Dr. N. Lingaiah

      Version of Record online: 5 JUN 2012 | DOI: 10.1002/cctc.201200110

      Thumbnail image of graphical abstract

      It′s all about the exchange: Smexchanged heteropoly tungstate catalyzes the synthesis of glycerol carbonate from glycerol and urea. The catalyst activity is related to the Lewis and Brønsted acidity, which depends on the Sm content in the catalysts. Partially exchanged SmxTPA catalyst showed high activity, owing to a higher number of Lewis acidic sites. The catalyst also exhibited high activity in the acidcatalyzed benzylation of anisole.

    13. Tailored Noble Metal Nanoparticles on γ-Al2O3 for High Temperature CH4 Conversion to Syngas (pages 1368–1375)

      Claudia Berger-Karin, Michael Sebek, Dr. Marga-Martina Pohl, Dr. Ursula Bentrup, Dr. Vita A. Kondratenko, Dr. Norbert Steinfeldt and Dr. Evgenii V. Kondratenko

      Version of Record online: 22 JUN 2012 | DOI: 10.1002/cctc.201200096

      Thumbnail image of graphical abstract

      Noble metals for a noble cause: Supporting tailored Rh nanoparticles (NP, 0.005 wt %) on Al2O3 yields active, selective, and stable catalysts for partial oxidation of methane to syngas. Transient mechanistic analysis reveals the origins of the superior performance of supported Rh NP compared with conventionally prepared Rh/Al2O3 catalysts with the same metal loading.

    14. The Unique Role of CaO in Stabilizing the Pt/Al2O3 Catalyst for the Dehydrogenation of Cyclohexane (pages 1376–1381)

      Dr. Jiafeng Yu, Dr. Rui Wang, Shiyuan Ren, Xiaoyan Sun, Chunlin Chen, Dr. Qingjie Ge, Dr. Wen Fang, Prof. Jian Zhang, Prof. Hengyong Xu and Prof. Dang Sheng Su

      Version of Record online: 21 MAY 2012 | DOI: 10.1002/cctc.201200067

      Thumbnail image of graphical abstract

      Catalyst body modification: The stability of the traditional Pt/Al2O3 catalyst was improved by doping with Ca, which effectively suppressed the deep dehydrogenation of H-rich carbonaceous components in the graphitic structure. Ca also promoted coke desorption by increasing the H/C ratio of H-deficient coke, thus favoring superior stability.

    15. Palladium-Catalyzed Allylic Oxidation of Monoterpenic Alkenes with Molecular Oxygen (pages 1382–1388)

      Dr. Aline C. Bueno, Ágatha O. de Souza and Prof. Elena V. Gusevskaya

      Version of Record online: 22 JUN 2012 | DOI: 10.1002/cctc.201200066

      Thumbnail image of graphical abstract

      A biomass bouquet, well-aerated: Highly valuable fragrance compounds can be obtained in good to excellent yields from renewable biomass-based substrates by a simple catalytic method, which uses the PdII/p-benzoquinone combination as a catalyst and molecular oxygen as a final oxidant.

    16. Tin(II) Antimonates with Adjustable Compositions: Effects of Band-Gaps and Nanostructures on Visible-Light-Driven Photocatalytic H2 Evolution (pages 1389–1396)

      Jinwen Shi, Lijing Ma, Po Wu, Zhaohui Zhou, Jiangang Jiang, Xiaokang Wan, Dr. Dengwei Jing and Prof. Dr. Liejin Guo

      Version of Record online: 29 JUN 2012 | DOI: 10.1002/cctc.201200063

      Thumbnail image of graphical abstract

      Everlas-tin love: A series of tin(II) antimonates with varied Sn content were found to be stable and efficient photocatalysts for visible-light-driven H2-evolution. Moreover, the relationships between their physicochemical properties—in particular their band-gaps (see figure) and nanostructures—and their photocatalytic activities were comprehensively investigated.

    17. Catalytic NO Oxidation Pathways and Redox Cycles on Dispersed Oxides of Rhodium and Cobalt (pages 1397–1404)

      Dr. Brian M. Weiss, Dr. Nancy Artioli and Prof. Enrique Iglesia

      Version of Record online: 22 MAY 2012 | DOI: 10.1002/cctc.201200050

      Thumbnail image of graphical abstract

      NO catalyst is an island: The oxidation of NO on RhO2 and Co3O4 is limited by the activation of O2 at vacancies on oxygen-saturated surfaces. Oxygen-binding energies set the vacancy densities and turnover rates. Oneelectron reductions that are accessible to RhO2 and Co3O4 facilitate O2 activation and allow faster 16O218O2 exchange and NO oxidation than expected from their oxygen-binding strengths.

    18. Aqueous Solutions of Mo-V-Phosphoric Heteropoly Acids as Bifunctional Catalysts For Preparation of 9,10-Anthraquinone and its Hydrogenated Derivatives (pages 1405–1410)

      Prof. Elena G. Zhizhina and Dr. Viktor F. Odyakov

      Version of Record online: 8 JUN 2012 | DOI: 10.1002/cctc.201200039

      Thumbnail image of graphical abstract

      Struck by a smooth quiminal: A catalytic one-pot process was realized in aqueous Mo-V-phosphoric heteropoly acid solutions. Acid-catalyzed condensations of 1,4-benzoquinone and 1,4-naphthoquinone with 1,3-butadiene are combined smoothly with oxidative dehydrogenation of generated adducts.

    19. Re-dispersion of Cobalt on a Model Fischer–Tropsch Catalyst During Reduction–Oxidation–Reduction Cycles (pages 1411–1419)

      M. M. Hauman, Dr. A. Saib, Dr. D. J. Moodley, Dr. E. du Plessis, Prof. Dr. M. Claeys and Prof. Dr. E. van Steen

      Version of Record online: 12 JUL 2012 | DOI: 10.1002/cctc.201200034

      Thumbnail image of graphical abstract

      A gradual break-up: The oxidation of metallic cobalt results in the formation of smaller Co3O4 crystallites, which, upon re-reduction, leads to an enhanced dispersion of the metallic cobalt phase. This method is suitable to regenerate sintered cobalt-based Fischer–Tropsch catalysts.

    20. Molecular Understanding of Enyne Hydrogenation over Palladium and Copper Catalysts (pages 1420–1427)

      Dr. Blaise Bridier, Dr. David Karhánek, Prof. Javier Pérez-Ramírez and Prof. Núria López

      Version of Record online: 26 JUN 2012 | DOI: 10.1002/cctc.201200021

      Thumbnail image of graphical abstract

      Eny-thing is possible: Selectivitydirecting factors during the gas phase hydrogenation of enyne compounds on palladium and copper catalysts is derived by combining catalytic tests at ambient pressure and density functional theory simulations. An extended Brønsted–Evans–Polanyi relationship is evidenced for the vinylacetylene and valylene substrates and the active metals in the hydrogenation mechanism.

    21. Methanol-to-Olefin Conversion Catalyzed by Low-Silica AlPO-34 with Traces of Brønsted Acid Sites: Combined Catalytic and Spectroscopic Investigations (pages 1428–1435)

      Dr. Weili Dai, Dr. Xin Wang, Dr. Guanjun Wu, Prof. Landong Li, Prof. Dr. Naijia Guan and Prof. Dr. Michael Hunger

      Version of Record online: 10 JUL 2012 | DOI: 10.1002/cctc.201100503

      Thumbnail image of graphical abstract

      Less silicon, more action: Chabazite-type silicoaluminophosphate with low molar silicon content is a methanol-to-olefin conversion catalyst with high activity and prolonged lifetime. Traces of Brønsted acid sites and benzene-based carbenium ions are responsible for this interesting catalytic property.

SEARCH

SEARCH BY CITATION