ChemCatChem

Cover image for ChemCatChem

February 6, 2012

Volume 4, Issue 2

Pages 137–275

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Minireview
    6. Highlights
    7. Concept
    8. Communications
    9. Full Papers
    10. Preview
    1. Cover Picture: Thermochemistry and Reaction Barriers for the Formation of Levoglucosenone from Cellobiose (ChemCatChem 2/2012) (page 137)

      Dr. Rajeev S. Assary and Dr. Larry A. Curtiss

      Article first published online: 27 JAN 2012 | DOI: 10.1002/cctc.201290000

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      Pyrolysis of Cellobiose The cover picture shows a likely intra-molecular hydrogen shift during the gas phase pyrolysis of cellobiose, a subunit of cellulose. In the full paper on p. 200 ff., R. S. Assary and L. A. Curtiss report the application of high-level quantum chemical methods to compute the thermodynamics and reaction barriers for the formation of levoglucosenone from cellobiose, which is helpful in finding new experimental routes to this product. The computational studies predict that the ether bond cleavage in cellobiose occurs through internal hydrogen transfer in gas phase and that the activation energy required is similar to that required to activate cellulose. The initials IACT stand for the Institute for Atom-efficient Chemical Transformations, an Energy Frontier Research Center funded by the U.S. Department of Energy.

  2. Graphical Abstract

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    3. Graphical Abstract
    4. News
    5. Minireview
    6. Highlights
    7. Concept
    8. Communications
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    1. Graphical Abstract: ChemCatChem 2/2012 (pages 139–144)

      Article first published online: 27 JAN 2012 | DOI: 10.1002/cctc.201290001

  3. News

    1. Top of page
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    4. News
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    6. Highlights
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    1. Spotlights on our sister journals: ChemCatChem 2/2012 (pages 148–150)

      Article first published online: 27 JAN 2012 | DOI: 10.1002/cctc.201290002

  4. Minireview

    1. Top of page
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    3. Graphical Abstract
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    1. Organocatalytic Asymmetric Additions to meso-Anhydrides and Azlactones (pages 151–168)

      Dr. Zaida Rodriguez-Docampo and Prof. Stephen J. Connon

      Article first published online: 28 OCT 2011 | DOI: 10.1002/cctc.201100266

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      Cracking the nut: Two related but distinct organocatalytic ring-opening processes are discussed in this review, as renewed interest from researchers and advances in catalyst design have alerted the community to their potential utility.

  5. Highlights

    1. Top of page
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    3. Graphical Abstract
    4. News
    5. Minireview
    6. Highlights
    7. Concept
    8. Communications
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    1. Dyes as Visible Light Photoredox Organocatalysts (pages 169–171)

      Davide Ravelli and Prof. Maurizio Fagnoni

      Article first published online: 7 DEC 2011 | DOI: 10.1002/cctc.201100363

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      Tomorrow always dyes! Organic dyes (e.g., Rose Bengal, Eosin Y) have been recently used as versatile photoredox organocatalysts in place of metal complexes (e.g., Ru2+ salts). Accordingly, photoinduced electron transfer reactions induced by excited dyes were exploited in various synthetic processes. The reactions were performed under metal-free conditions and visible light irradiation.

    2. Single-Step Metallocatalyzed and Organocatalyzed Enantioselective Construction of Bicyclo[3.2.1]octanes (pages 172–174)

      Dr. Marc Presset, Dr. Yoann Coquerel and Prof. Dr. Jean Rodriguez

      Article first published online: 6 DEC 2011 | DOI: 10.1002/cctc.201100357

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      Pushing the dominos after 100 years: Almost a century has elapsed since the pioneer one-pot preparation of a racemic functionalized bicyclo[3.2.1]octane nucleus in 1903, and their first metal-catalyzed direct enantioselective synthesis from achiral precursors in 1999. Both metallic and organic catalytic domino transformations are pivotal developments in the direct construction of functionalized bicyclo[3.2.1]octanes from simple achiral precursors.

    3. Simple and Sustainable Copper–O2 Chemistry towards High-Value Products (pages 175–176)

      Dr. Miquel Costas

      Article first published online: 22 NOV 2011 | DOI: 10.1002/cctc.201100350

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      Oxygen meets its end, or does it? Straightforward Cu-catalyzed preparation of α-ketoamides has been recently achieved through oxidative coupling of aryl acetaldehydes and arylamines by using O2 as the terminal oxidant. The work represents a remarkable example of a simple and sustainable transformation to yield elaborate and more complex biologically relevant oxidized products from readily available reagents under mild conditions.

  6. Concept

    1. Top of page
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    4. News
    5. Minireview
    6. Highlights
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    8. Communications
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    1. Catalysis with In Situ-Generated (Hypo)iodite Ions for Oxidative Coupling Reactions (pages 177–185)

      Dr. Muhammet Uyanik and Prof. Dr. Kazuaki Ishihara

      Article first published online: 23 DEC 2011 | DOI: 10.1002/cctc.201100352

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      Hyping up the iodines: The discovery and development of oxidative coupling reactions catalyzed by inorganic iodine species (i.e., hypoiodite or iodite), which are generated in situ from an iodide ion and hydrogen peroxide or tert-butyl hydroperoxide as an environmentally benign oxidant is highlighted.

  7. Communications

    1. Top of page
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    1. para-Selective Aerobic Oxidative C[BOND]H Olefination of Aminobenzenes Catalyzed by Palladium/Molybdovanadophosphoric acid/2,4,6-Trimethylbenzoic Acid System (pages 187–191)

      Yohei Mizuta, Dr. Yasushi Obora, Yosuke Shimizu and Prof. Yasutaka Ishii

      Article first published online: 12 DEC 2011 | DOI: 10.1002/cctc.201100375

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      Pick of the bunch: Oxidative C[BOND]H olefination of aminobenzenes with acrylates was achieved using a palladium/molybdovanadophosphoric acid (HPMoV)/2,4,6-trimethylbenzoic acid (TMBA) system under O2 (1 atm) in DMF. The highly regio- and stereoselective C[BOND]H olefination of basic substrates such as aminobenzenes is important in organic synthesis; (E)-para-alkenyl-substituted aminobenzenes were produced in high yields.

    2. The Direct Arylation of Unactivated Arenes with Aryl Halides Catalyzed by a Magnetically Recyclable Fe-Ni Alloy (pages 192–195)

      Rongzhao Zhang, Dr. Cheng-Xia Miao, Shoufeng Wang, Prof. Dr. Chungu Xia and Prof. Dr. Wei Sun

      Article first published online: 15 DEC 2011 | DOI: 10.1002/cctc.201100320

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      Alloy, alloy! A cheap magnetic Fe-Ni alloy is prepared using a simple method and applied to the direct arylation of unactivated arenes with aryl halides. The catalyst exhibits excellent activity and can be reused at least eight times without a significant loss of catalytic activity.

    3. Chemoenzymatic Reduction of Conjugated C[DOUBLE BOND]C Double Bonds (pages 196–199)

      Julie Bernard, Prof. Dr. Esta van Heerden, Prof. Dr. Isabel W. C. E. Arends, Dr. Diederik J. Opperman and Dr. Frank Hollmann

      Article first published online: 6 DEC 2011 | DOI: 10.1002/cctc.201100312

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      An addiction to rhodium: A nicotinamide-independent regeneration approach for enoate reductases is proposed. The transition metal complex [Cp*Rh(bpy)(H2O)]2+ can replace both the nicotinamide cofactor and a corresponding enzymatic regeneration system, which results in a simplified reaction system. This system is characterized and applied to the chemoenzymatic reduction of various conjugated C[DOUBLE BOND]C double bonds.

    4. Thermochemistry and Reaction Barriers for the Formation of Levoglucosenone from Cellobiose (pages 200–205)

      Dr. Rajeev S. Assary and Dr. Larry A. Curtiss

      Article first published online: 19 OCT 2011 | DOI: 10.1002/cctc.201100280

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      Cellobiose jumps the barrier: High-level quantum mechanical studies show that the ether bond cleavage in cellobiose occurs through internal hydrogen transfer in the gas phase and that the activation energy required is similar to that required for activating cellulose. The reaction barriers are computed for various pathways for the formation of levoglucosenone from levoglucosan, and the most likely pathway requires a relatively low activation barrier compared to that for the activation of cellobiose.

    5. Pd/Al(OTf)3 Catalyzed Methoxycarbonylation: On the Importance of Counterions and the Acid Source (pages 206–208)

      Prof. D. Bradley G. Williams and Tyler Bredenkamp

      Article first published online: 29 NOV 2011 | DOI: 10.1002/cctc.201100238

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      The unnatural selection: The use of aluminum triflate as a promoter for the Pd catalyzed methoxycarbonylation of 1-octene allowed an investigation into the role of the acid and counterion on the activity and selectivity of the catalyst. With this promoter there is no counterion effect at all for AcO, p-TsO, MsO, or TfO counterions. The results imply that the nature of the acid determines catalyst activity, assuming the presence of a weakly coordinating counterion.

  8. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Minireview
    6. Highlights
    7. Concept
    8. Communications
    9. Full Papers
    10. Preview
    1. Sr–Mg Mixed Oxides as Biodiesel Production Catalysts (pages 209–216)

      Dr. Kajornsak Faungnawakij, Dr. Boonyawan Yoosuk, Dr. Supawadee Namuangruk, Pawnprapa Krasae, Dr. Nawin Viriya-empikul and Buppa Puttasawat

      Article first published online: 6 DEC 2011 | DOI: 10.1002/cctc.201100346

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      Build a base in your base: The synergistic effect of Sr and Mg species acting as heterogeneous catalysts is observed in biodiesel production as it enhances the activity, which is attributable to new strong basic sites as evidenced by using CO2-TPD measurements and DFT calculations.

    2. On the Microdistributions of Cr-Ion Complexes within mm-Sized γ-Al2O3 Catalyst Bodies upon Impregnation as Studied by UV/Vis and Raman Microspectroscopy (pages 217–227)

      Dr. Mathijs W. Zandbergen, Dr. Andrew M. Beale and Prof. Dr. ir. Bert M. Weckhuysen

      Article first published online: 6 DEC 2011 | DOI: 10.1002/cctc.201100333

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      Livin′ on the edge: The microdistributions of the Cr-ion complexes were altered by exploiting the opposite charge of the CrIII and CrVI complexes. The microdistributions of the Cr-ion complexes were altered by exploiting the opposite charge of the CrIII and CrVI complexes.

    3. Metal Oxide-Supported Platinum Overlayers as Proton-Exchange Membrane Fuel Cell Cathodes (pages 228–235)

      Dr. Vladimir Tripković, Dr. Frank Abild-Pedersen, Dr. Felix Studt, Dr. Isotta Cerri, Dr. Tetsuo Nagami, Dr. Thomas Bligaard and Prof. Jan Rossmeisl

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cctc.201100308

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      Rule of the platinum overlayer: Several rutile metal oxide-supported n=(1,2,3) platinum overlayers prove, by means of density functional theory calculations, active catalysts for oxygen reduction reaction, with some candidates even surpassing Pt. Catalyst performance is evaluated against Pt(111) skins on Pt3X (X=Ni, Co, Fe, Ti, Sc and Y), the best known catalysts for the reaction.

    4. The Dynamic Structure of Gold Supported on Ceria in the Liquid Phase Hydrogenation of Nitrobenzene (pages 236–242)

      Christiane Kartusch, Martin Makosch, Jacinto Sá, Prof. Dr. Konrad Hungerbuehler and Prof. Dr. Jeroen A. van Bokhoven

      Article first published online: 12 DEC 2011 | DOI: 10.1002/cctc.201100187

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      The dynamism of gold: The oxidation state of gold in Au/CeO2 catalysts is determined in situ in the slurry phase of the hydrogenation of nitrobenzene by means of high-resolution X-ray absorption spectroscopy. No evidence has been found that the detected cationic gold contributes to the catalytic activity.

    5. You have full text access to this OnlineOpen article
      Single Site Supported Cationic Rhodium(I) Complexes for the Selective Redox Isomerization of Allylic Alcohols (pages 243–250)

      Dr. Suman Sahoo, Helena Lundberg, Assoc. Prof. Mattias Edén, Nanna Ahlsten, Dr. Wei Wan, Prof. Xiaodong Zou and Assoc. Prof. Belén Martín-Matute

      Article first published online: 9 JAN 2012 | DOI: 10.1002/cctc.201100321

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      Stuck in the middle with rhodium: The isomerization of allylic alcohols using a rhodium complex immobilized on mesoporous silica materials was studied. The efficiency of the heterogeneous catalyst was influenced by the nature of the ligands and of the material used. Immobilization of the metal complex on AlSBA-15 resulted in a highly active and selective catalyst that can be recycled several times.

    6. On the Role of Residual Ag in Nanoporous Au Catalysts for CO Oxidation: A Combined Microreactor and TAP Reactor Study (pages 251–259)

      Dr. L. C. Wang, Y. Zhong, D. Widmann, Prof. Dr. J. Weissmüller and Prof. Dr. R. J. Behm

      Article first published online: 12 DEC 2011 | DOI: 10.1002/cctc.201100297

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      The silver that got left behind: The oxidation of CO on nanoporous Au, in particular the activation of molecular O2, was investigated by a combination of kinetic and TAP measurements. For the stable catalyst, the amount of adsorbed active oxygen is linearly related to the surface Ag content.

    7. Oxidative Dehydrogenation of Propane over MoOx and POx Supported on Carbon Nanotube Catalysts (pages 260–264)

      Zhenwei Bai, Peng Li, Liping Liu and Prof. Dr. Guang Xiong

      Article first published online: 13 JAN 2012 | DOI: 10.1002/cctc.201100242

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      And the best supporting catalyst is… The addition of both POx and MoOx can improve the selectivity at the same conversion rate and maintain the stability of the carbon nanotube catalyst. Catalytic performance for the oxidative dehydrogenation of propane is investigated.

    8. SBA-16-Supported Cobalt Catalyst with High Activity and Stability for Fischer–Tropsch Synthesis (pages 265–272)

      Yanxi Zhao, Yuhua Zhang, Jian Chen, Prof. Jinlin Li, Prof. Kongyong Liew and Mohd Ridzuan Bin Nordin

      Article first published online: 5 DEC 2011 | DOI: 10.1002/cctc.201100223

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      The importance of being SBA-16: Co/SBA-16 catalysts are prepared by means of the incipient wetness impregnation method for Fischer–Tropsch synthesis (FTS). Most of the Co3O4 nanoparticles are introduced into the SBA-16 cages. High FTS activity and stability are observed on the SBA-16-supported catalyst. SBA-16 support can efficiently prevent the aggregation and sintering of cobalt nanoparticles.

  9. Preview

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Minireview
    6. Highlights
    7. Concept
    8. Communications
    9. Full Papers
    10. Preview
    1. You have free access to this content
      Preview: ChemCatChem 3/2012 (page 275)

      Article first published online: 27 JAN 2012 | DOI: 10.1002/cctc.201290003

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