ChemCatChem

Cover image for Vol. 3 Issue 12

December 16, 2011

Volume 3, Issue 12

Pages 1833–1959

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Highlights
    6. Minireview
    7. Communications
    8. Full Papers
    9. Book Review
    10. Preview
    1. Cover Picture: The Catalytic Amination of Alcohols (ChemCatChem 12/2011) (page 1833)

      Sebastian Bähn, Sebastian Imm, Lorenz Neubert, Prof. Dr. Min Zhang, Dr. Helfried Neumann and Prof. Dr. Matthias Beller

      Article first published online: 8 DEC 2011 | DOI: 10.1002/cctc.201190050

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      Amination of Alcohols The cover picture shows the catalytic cycle for the environmentally benign amination of alcohols via the so-called Borrowing Hydrogen methodology. In their Minireview on p. 1853 ff., Beller and co-workers describe the actual developments for the synthesis of amines by amination of alcohols. Notably, compared to other synthetic methodologies for the synthesis of amines, this type of transformation is highly attractive because alcohols are readily available and the only side-product is water.

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Highlights
    6. Minireview
    7. Communications
    8. Full Papers
    9. Book Review
    10. Preview
    1. Graphical Abstract: ChemCatChem 12/2011 (pages 1835–1840)

      Article first published online: 8 DEC 2011 | DOI: 10.1002/cctc.201190051

  3. News

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Highlights
    6. Minireview
    7. Communications
    8. Full Papers
    9. Book Review
    10. Preview
  4. Highlights

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Highlights
    6. Minireview
    7. Communications
    8. Full Papers
    9. Book Review
    10. Preview
    1. Organocatalytic Asymmetric 1,6-Addition Reactions (pages 1847–1849)

      Dr. Akkattu T. Biju

      Article first published online: 23 SEP 2011 | DOI: 10.1002/cctc.201100279

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      A new door is open! Conceptually new organocatalytic enantioselective 1,6-addition reactions have recently been uncovered by the groups of Jørgensen, Alexakis, and Stephens. Key to their success was the design of appropriate organocatalyts and Michael acceptors with unique reactivities, which lead to highly regioselective and enantioselective products.

    2. Benzothiazoline: The Surrogate of Hantzsch Ester (pages 1850–1851)

      Dr. Chen Zhu and Prof. Dr. John Russell Falck

      Article first published online: 25 AUG 2011 | DOI: 10.1002/cctc.201100241

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      Versatile hydrogen source: A number of intriguing features of benzothiazoline are summarized to highlight its achievement in the reduction of C[DOUBLE BOND]N bonds. Its inherently versatile skeleton will allow benzothiazoline to become an important complement to the Hantzsch ester and find broad applications in the field of transfer hydrogenation.

  5. Minireview

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Highlights
    6. Minireview
    7. Communications
    8. Full Papers
    9. Book Review
    10. Preview
    1. You have free access to this content
      The Catalytic Amination of Alcohols (pages 1853–1864)

      Sebastian Bähn, Sebastian Imm, Lorenz Neubert, Prof. Dr. Min Zhang, Dr. Helfried Neumann and Prof. Dr. Matthias Beller

      Article first published online: 14 OCT 2011 | DOI: 10.1002/cctc.201100255

      Thumbnail image of graphical abstract

      Something borrowed, something new: The amination of alcohols is a valuable method for the synthesis of amines and is already used on an industrial scale. This elegant transformation makes use of readily available, in some cases bio-derived alcohols and produces water as the only by-product. In this Minireview, recent developments in the amination of alcohols by means of the so-called borrowing hydrogen methodology are presented.

  6. Communications

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Highlights
    6. Minireview
    7. Communications
    8. Full Papers
    9. Book Review
    10. Preview
    1. Catalytic and Kinetic Studies of the Dehydrogenation of Dimethylamine Borane with an iPr Substituted Titanocene Catalyst (pages 1865–1868)

      Dr. Torsten Beweries, Johannes Thomas, Dr. Marcus Klahn, Prof. Dr. Axel Schulz, Prof. Dr. Detlef Heller and Prof. Dr. Uwe Rosenthal

      Article first published online: 11 OCT 2011 | DOI: 10.1002/cctc.201100283

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      iPr tips the scales: Simple introduction of an iPr group to the Cp ligand in titanocene alkyne complexes of the type [Cp′2Ti(η2-Me3SiC2SiMe3)] (Cp′= cyclopentadienyl) gives a highly active catalyst for dimethylamine borane dehydrogenation. In this communication, a detailed study of the scope of this complex and the reaction kinetics is presented.

    2. Synthesis of Titanium Chabazite: A New Shape Selective Oxidation Catalyst with Small Pore Openings and Application in the Production of Methyl Formate from Methanol (pages 1869–1871)

      Einar André Eilertsen, Prof. Silvia Bordiga, Prof. Carlo Lamberti, Dr. Alessandro Damin, Dr. Francesca Bonino, Dr. Bjørnar Arstad, Prof. Stian Svelle, Prof. Unni Olsbye and Prof. Karl Petter Lillerud

      Article first published online: 28 SEP 2011 | DOI: 10.1002/cctc.201100281

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      Take CHAnce on zeolites: A new titanium silicate oxidation catalyst (Ti-CHA) and a bifunctional titanium aluminum silicate catalyst (Ti-Al-CHA) with the chabazite (CHA) topology have been synthesized. The materials have a 3-dimensional channel system with small pore openings that enable shape selective oxidation catalysis. The new Ti-Al-CHA material facilitates a high conversion of methanol to methyl formate with a selectivity of 85 % at 60 °C, using H2O2 as the oxidation agent.

    3. Gold Catalysis Outside Nanoscale: Bulk Gold Catalyzes the Aerobic Oxidation of π-Activated Alcohols (pages 1872–1875)

      Dr. Hongfan Guo, Afnan Al-Hunaiti, Dr. Marianna Kemell, Sari Rautiainen, Prof. Dr. Markku Leskelä and Prof. Dr. Timo Repo

      Article first published online: 14 OCT 2011 | DOI: 10.1002/cctc.201100286

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      The incredible bulk: Although nano-sized Au is required in numerous reactions, π-activated alcohols, such as benzyl alcohol and cinnamyl alcohol, can be catalytically oxidized by unsupported bulk Au, which provides a promising starting point to explore the origin of Au catalysis.

    4. Dendralenes Preparation via Ene–Yne Cross-Metathesis from In Situ Generated 1,3-Enynes (pages 1876–1879)

      Hassan Srour, Kaouther Abidi, Zeyneb Sahli, Dr. Basker Sundararaju, Dr. Naceur Hamdi, Dr. Mathieu Achard and Dr. Christian Bruneau

      Article first published online: 11 OCT 2011 | DOI: 10.1002/cctc.201100251

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      The propargyl way: Various [3]dendralenes can be obtained from propargylic alcohols by means of a straightforward one-pot two-step reaction in the presence of ruthenium complexes, with water as the only side product.

    5. Recycling Chiral Copper Bis(oxazoline) Complexes in an Original Multireaction Procedure (pages 1880–1884)

      Dorian Didier and Dr. Emmanuelle Schulz

      Article first published online: 12 OCT 2011 | DOI: 10.1002/cctc.201100250

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      Precipitation–the solution? The recovery of a chiral copper(II) bis(oxazoline) catalyst by charge-transfer complexation and subsequent precipitation allows its efficient reuse in ene and cyclopropanation reactions for up to ten successive catalytic cycles and affords the desired products in high yields and enantioselectivities. The same catalyst batch is also successfully reused in three different asymmetric transformations in an original multireaction procedure.

    6. Glucose Oxidase-Mediated Reduction Processes: H2 Evolution, Hydrogenation of Acetylene, and Reduction of NO3 by Glucose (pages 1885–1888)

      Sara Raichlin, Omer Yehezkeli, Dr. Ran Tel-Vered and Prof. Itamar Willner

      Article first published online: 21 OCT 2011 | DOI: 10.1002/cctc.201100247

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      Glucose oxidase has it all: Under anaerobic conditions, glucose oxidase mediates H2 evolution, hydrogenation processes, and biocatalytic cascades reducing NO3. These processes may provide new biotechnological platforms for the generation of fuel products from biomass or for the synthesis of products.

    7. Comparison of Superparamagnetic Fe3O4-Supported N-Heterocyclic Carbene-Based Catalysts for Enantioselective Allylation (pages 1889–1891)

      Dr. Kalluri V. S. Ranganath, Dr. Andreas H. Schäfer and Prof. Dr. Frank Glorius

      Article first published online: 4 OCT 2011 | DOI: 10.1002/cctc.201100201

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      Once, twice, three times a catalyst: Iron oxide nanoparticles (NPs) were functionalized through a silane linker by a chiral imidazolium salt on the surface, a latent N-heterocyclic carbene precursor. This system was utilized in three ways in the enantioselective allylation of 4-nitrobenzaldehyde: as an organocatalyst (1); as a molecular metal complex catalyst (2), when together with [Pd(OAc)2]; and as a matrix for the formation of Pd NPs and, subsequently, as an active chiral NP catalyst (3). Enantiomeric excesses of up to 74 % were obtained.

  7. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Highlights
    6. Minireview
    7. Communications
    8. Full Papers
    9. Book Review
    10. Preview
    1. Impact of Co-Components on the State of Pd and the Performance of Supported Pd/TiO2 Catalysts in the Gas-Phase Acetoxylation of Toluene (pages 1893–1901)

      Suresh Gatla, Neetika Madaan, Dr. Jörg Radnik, Dr. Venkata Narayana Kalevaru, Prof. Bernhard Lücke, Dr. Andreas Martin, Dr. Ursula Bentrup and Prof. Angelika Brückner

      Article first published online: 11 OCT 2011 | DOI: 10.1002/cctc.201100225

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      A new twist for activity: Adding a second metal M to supported Pd/TiO2 catalysts modifies the state of Pd and improves the performance in the acetoxylation of toluene to benzyl acetate, but in a different way: The more noble the metal M, the higher the selectivity, but the lower the activity.

    2. Enzyme Surface Glycosylation in the Solid Phase: Improved Activity and Selectivity of Candida Antarctica Lipase B (pages 1902–1910)

      Dr. Melissa L. E. Gutarra, Oscar Romero, Dr. Olga Abian, Prof. Fernando A. G. Torres, Prof. Denise M. G. Freire, Dr. Aline M. Castro, Prof. Jose M. Guisan and Dr. Jose M. Palomo

      Article first published online: 11 OCT 2011 | DOI: 10.1002/cctc.201100211

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      Enzyme's sweet tooth: Incorporation of a sugar tag into an enzyme is an interesting methodology to improve its catalytic properties. Candida antarctica lipase (fraction B) modified with tailor-made oligosaccharides on a protein surface in the solid phase exhibits improved activity, selectivity, or regioselectivity values.

    3. Catalytic Aminolysis (Amide Formation) from Esters and Carboxylic Acids: Mechanism, Enhanced Ionic Liquid Effect, and its Origin (pages 1911–1920)

      Vanda Maria de Oliveira, Richard Silva de Jesus, Alexandre F. Gomes, Prof. Dr. Fábio C. Gozzo, Prof. Dr. Alexandre P. Umpierre, Prof. Dr. Paulo A. Z. Suarez, Prof. Dr. Joel C. Rubim and Prof. Dr. Brenno A. D. Neto

      Article first published online: 26 OCT 2011 | DOI: 10.1002/cctc.201100221

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      Amides ride the ionic liquid cycles: A novel catalytic method to perform amide bond formation from esters and carboxylic acids in ionic liquids is described. Mechanistic studies and the ionic liquid effect are also investigated. Recycling reactions are performed successfully. NMR and electrospray ionization–quadrupole time-of-flight experiments allowed for the proposition of a catalytic cycle to explain the reaction with Brønsted acids, such as SnCl2 and CdO.

    4. Enantiopure Triazolium Salts: Chemoenzymatic Synthesis and Applications in Organocatalysis (pages 1921–1928)

      Nicolás Ríos-Lombardía, Raúl Porcar, Dr. Eduardo Busto, Dr. Ignacio Alfonso, Dr. Jose Montejo-Bernardo, Prof. Santiago García-Granda, Prof. Vicente Gotor, Prof. Santiago V. Luis, Dr. Eduardo García-Verdugo and Dr. Vicente Gotor-Fernández

      Article first published online: 14 OCT 2011 | DOI: 10.1002/cctc.201100218

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      Pure as the driven salt: A straightforward chemoenzymatic synthesis and organocatalytic applications of a new family of enantiopure triazolium salts are demonstrated. The influence of the different structural design vectors is discussed, and a broad range of conversions and some degree of enantiopreference for all catalysts tested is observed.

    5. The Iron-Catalyzed Oxidation of Alkynes—1,2-Dione Formation Versus Oxidative Cleavage—A Matter of Temperature (pages 1929–1934)

      Dr. Stephan Enthaler

      Article first published online: 14 OCT 2011 | DOI: 10.1002/cctc.201100206

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      Inexpensive and environmentally friendly! In this study, the iron-catalyzed oxidation of 1,2-substituted alkynes with hydrogen peroxide is investigated. Two different pathways can be observed: First, the formation of 1,2-diones, and second, the oxidative cleavage of the triple bond to obtain carboxylic acids. The reaction temperature is found to be crucial in determining the path.

    6. Statistical Analysis of Past Catalytic Data on Oxidative Methane Coupling for New Insights into the Composition of High-Performance Catalysts (pages 1935–1947)

      Dr. Ulyana Zavyalova, Dr. Martin Holena, Prof. Dr. Robert Schlögl and Prof. Dr. Manfred Baerns

      Article first published online: 29 SEP 2011 | DOI: 10.1002/cctc.201100186

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      The more the merrier: This paper discusses the contributions of significant combinations of elements to the mean values of selectivity and yield in the oxidative coupling of methane (OCM) reaction derived from the statistical analysis of about 1870 past catalytic data sets (see figure). The applied methodology allows the identification of the main prerequisites in catalyst compositions for advanced design of high-performance OCM catalysts. Correlation coefficients, decision trees, and analysis of variance are most useful tools.

    7. Application of Hierarchical Porous Silica with a Stable Large Porosity for β-Galactosidase Immobilization (pages 1948–1954)

      Claudia Bernal, Prof. Ligia Sierra and Prof. Monica Mesa

      Article first published online: 23 SEP 2011 | DOI: 10.1002/cctc.201100174

      Thumbnail image of graphical abstract

      Pin that enzyme down: Hierarchical porous silica, synthesized by using sodium silicate, is used as support for immobilization of β-galactosidase by the adsorption pathway. Their loading capacity and enzyme retention are explained in terms of their large mesopores and macropores and the surface silanol groups. Under extreme conditions, the hybrid biocatalyst is more stable than the soluble β-galactosidase.

  8. Book Review

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Highlights
    6. Minireview
    7. Communications
    8. Full Papers
    9. Book Review
    10. Preview
    1. On Catalysis. Edited by Wladimir Reschetilowski and Wolfgang Hönle (page 1955)

      Prof. Wolfgang Grünert

      Article first published online: 14 OCT 2011 | DOI: 10.1002/cctc.201100217

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      VWB Verlag für Wissenschaft und Bildung Berlin 2010, (Edition Ostwald, volume 2), 268 pages, € 34, ISBN 978-3-86135-232-7

  9. Preview

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Highlights
    6. Minireview
    7. Communications
    8. Full Papers
    9. Book Review
    10. Preview
    1. You have free access to this content
      Preview: ChemCatChem 1/2012 (page 1959)

      Article first published online: 8 DEC 2011 | DOI: 10.1002/cctc.201190053

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