ChemCatChem

Cover image for Vol. 2 Issue 10

October 11, 2010

Volume 2, Issue 10

Pages 1177–1327

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Highlights
    7. Communications
    8. Full Papers
    9. Preview
    1. Cover Picture: Enantiopure Monoprotected cis-1,2-Diaminocyclohexane: One-Step Preparation and Application in Asymmetric Organocatalysis (ChemCatChem 10/2010) (page 1177)

      Prof. Dr.  A. Berkessel, M.-C. Ong, M. Nachi and Dr.  J.-M. Neudörfl

      Article first published online: 5 OCT 2010 | DOI: 10.1002/cctc.201090039

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      The cover picture shows the desymmetrization of cis-1,2-diaminocyclohexane (cis-DACH) to its mono-allyloxycarbonyl (Alloc) derivative. In their communication on p 1215 ff., Berkessel and co-workers describe a highly efficient method for the preparation of mono-protected cis-DACH. By using the enzyme Candida antarctica lipase B as catalyst and diallyl carbonate as the acyl donor, mono-N-alloc cis-DACH is obtained in a single step with high yield and enantiopurity. Both enantiomeric forms of a cis-DACH-derived trifluoromethanesulfonamide are applied as highly selective organocatalysts in a direct aldol reaction. Cover design by Silvia Elfert, photo credits to cloudzilla.

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Highlights
    7. Communications
    8. Full Papers
    9. Preview
    1. Graphical Abstract: ChemCatChem 10/2010 (pages 1179–1184)

      Article first published online: 5 OCT 2010 | DOI: 10.1002/cctc.201090040

  3. News

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

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Highlights
    7. Communications
    8. Full Papers
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    1. Rhodium- and Iridium-Catalyzed Hydroamination of Alkenes (pages 1192–1207)

      Kevin D. Hesp and Mark Stradiotto

      Article first published online: 19 JUL 2010 | DOI: 10.1002/cctc.201000102

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      Transition metal-catalyzed hydroamination reactions represent atom-economical methods for the construction of new C[BOND]N bonds from readily available starting materials. This Review provides a brief historical account and an overview of current activity in the rapidly evolving area of rhodium- and iridium-catalyzed hydroamination of alkenes with a focus on catalyst composition and scope, as well as on mechanistic studies that have contributed to our understanding of these transformations.

  5. Highlights

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Highlights
    7. Communications
    8. Full Papers
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    1. Tandem Rh/Ru Hydroformylation/Hydrogenation of Terminal Olefins to Linear Alcohols (pages 1209–1211)

      Prof. Charles P. Casey

      Article first published online: 3 AUG 2010 | DOI: 10.1002/cctc.201000221

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      Growing chains: Kyoko Nozaki's group at the University of Tokyo recently reported the highest yielding tandem hydroformylation/hydrogenation system for the production of one carbon chain-extended linear alcohols from terminal alkenes in 90 % yield.

    2. Self-Assembled Molecular Reaction Vessels Reloaded (pages 1212–1214)

      Prof. Dr. Arne Lützen

      Article first published online: 27 JUL 2010 | DOI: 10.1002/cctc.201000198

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      Enzyme-like catalysis of Nazarov cyclizations has been achieved by encapsulation of pentadienols into a metallosupramolecular capsule. Constrictive binding of the substrate and functional-group activation give rise to a tremendous rate acceleration of up to a factor of 2.1×106, thus, pushing the efficiency of self-assembled molecular capsules as catalysts to a new level.

  6. Communications

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Highlights
    7. Communications
    8. Full Papers
    9. Preview
    1. Enantiopure Monoprotected cis-1,2-Diaminocyclohexane: One-Step Preparation and Application in Asymmetric Organocatalysis (pages 1215–1218)

      Prof. Dr.  A. Berkessel, M.-C. Ong, M. Nachi and Dr.  J.-M. Neudörfl

      Article first published online: 14 JUL 2010 | DOI: 10.1002/cctc.201000104

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      DACH to the future: A practical, one-step method for the highly enantioselective derivatization of cis-1,2-diaminocyclohexane (DACH), with diallyl carbonate as the acylating agent and Candida antarctica lipase B as catalyst is described. From the resulting enantiopure mono-N-alloc-cis-DACH, a series of derivatives are synthesized. The cis-DACH-derived sulfonamide catalysts gives high chemical yield, diastereo- and enantioselectivity in a direct aldol reaction.

    2. Hydrogenation Reactions on Au/TiC(001): Effects of Au[BOND]C Interactions on the Dissociation of H2 (pages 1219–1222)

      Dr. Elizabeth Florez, Tatiana Gomez, Dr. Ping Liu, Dr. José A. Rodriguez and Prof. Francesc Illas

      Article first published online: 23 JUL 2010 | DOI: 10.1002/cctc.201000190

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      Density functional calculations carried out for realistic models evidence that Au particles supported on TiC(001) are very active towards H2 dissociation. The molecular mechanisms show that the support is not a mere spectator but plays a major role in the catalyzed reaction and acts as a reservoir of atomic H, making this system an excellent candidate as a catalyst for the hydrogenation of olefins and hydrodesulfurization reactions.

    3. Catalytic Addition of Aromatic C[BOND]H Bonds to Vinylsilanes in the Presence of Ru/CeO2 (pages 1223–1225)

      Hiroki Miura, Dr. Kenji Wada, Dr. Saburo Hosokawa and Prof. Dr. Masashi Inoue

      Article first published online: 25 JUN 2010 | DOI: 10.1002/cctc.201000144

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      Special addition: The addition of aromatic C[BOND]H bonds to vinylsilanes proceeds smoothly in the presence of Ru/CeO2. The choice of appropriate additive realizes catalysis on the solid surface. This catalytic reaction can be carried out without solvent on a large scale to achieve a high turnover number. Modification of Ru/CeO2 with PPh3 under a H2 atmosphere markedly increases the catalytic activity.

    4. A New Insight into Gold(I)-Catalyzed Hydration of Alkynes: Proton Transfer (pages 1226–1230)

      Caroline M. Krauter, Prof. Dr. A. Stephen K. Hashmi and Dr. Markus Pernpointner

      Article first published online: 29 JUL 2010 | DOI: 10.1002/cctc.201000136

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      Solvent molecules have a significant impact on the mechanism of the gold(I)-catalyzed hydration of alkynes as they enable an efficient proton transfer step. As an alternative to such a water-assisted proton transfer, the counterion can serve as a proton shuttle. However, it seems likely that solvent molecules play a vital role for the overall reaction mechanism in either case.

    5. Bifunctional Mesoporous Materials with Coexisting Acidic and Basic Sites for C[BOND]C Bond Formation in Co-operative Catalytic Reactions (pages 1231–1234)

      Dr. Sankaranarayanapillai Shylesh, Alex Wagener, Dr. Andreas Seifert, Prof. Stefan Ernst and Prof. Werner R. Thiel

      Article first published online: 21 JUL 2010 | DOI: 10.1002/cctc.201000086

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      Graftwerk: Primary amines grafted onto mesoporous aluminosilicas act as efficient, recyclable bifunctional catalysts for the one-step co-operative catalytic Henry reaction of substituted benzaldehydes and nitromethane, irrespective of the nature of solvents used for the grafting process.

    6. Investigation of Acid Centers in MIL-53(Al, Ga) for Brønsted-Type Catalysis: In Situ FTIR and Ab Initio Molecular Modeling (pages 1235–1238)

      Dr. Ugo Ravon, Dr. Gérald Chaplais, Dr. Céline Chizallet, Behnam Seyyedi , Dr. Francesca Bonino , Prof. Dr. Silvia Bordiga , Dr. Nicolas Bats and Dr. David Farrusseng

      Article first published online: 13 SEP 2010 | DOI: 10.1002/cctc.201000055

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      Run of the MIL: In contrast to MIL-53(Al), IM-19 (MIL-53 (Ga)) is extremely active and selective for the alkylation of aromatics. The reaction proceeds through the protonation of the aromatic substrate. CO adsorption and molecular modeling show that the bridging μ2-OH of IM-19 exhibits stronger Brønsted-type acidity than does MIL-53(Al).

  7. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Highlights
    7. Communications
    8. Full Papers
    9. Preview
    1. Creating Cellulose-Binding Domain Fusions of the Coenzyme A Biosynthetic Enzymes to Enable Reactor-Based Biotransformations (pages 1239–1251)

      Ilse Rootman, Dr. Marianne de Villiers, Leisl A. Brand and Prof. Erick Strauss

      Article first published online: 2 SEP 2010 | DOI: 10.1002/cctc.201000197

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      Domain event: Coenzyme A (CoA) analogues are prepared by biotransformation of suitable pantothenamides using immobilized versions of three of the CoA biosynthetic enzymes. This transformation is achieved by fusing the enzymes to cellulose-binding domains (CBD), which allow for their simultaneous purification and immobilization. In this manner, batch and column reactors capable of continuous CoA analogue production can be prepared and successfully used.

    2. Kinetic Evaluation of Cooperative [Co(salen)] Catalysts in the Hydrolytic Kinetic Resolution of rac-Epichlorohydrin (pages 1252–1259)

      Dr. Xunjin Zhu, Dr. Krishnan Venkatasubbaiah, Prof. Marcus Weck and Prof. Christopher W. Jones

      Article first published online: 2 AUG 2010 | DOI: 10.1002/cctc.201000162

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      To compare the reactivity and selectivity of the different [Co(salen)] cooperative catalyst designs, 12 representative catalysts are employed in the hydrolytic kinetic resolution (HKR) of epichlorohydrin under identical conditions. The soluble cyclic oligomeric catalytic systems possess outstanding activity and enantioselectivity. A cross-linked polymer resin catalyst is identified as a promising, easily recyclable heterogeneous catalyst for HKR of epoxides.

    3. Silica-Immobilized Highly Dispersed Oxo–Rhenium and its Catalytic Activity for the Direct Synthesis of Nitrones (pages 1260–1264)

      Bhawan Singh, Dr. Suman L. Jain, Bharat S. Rana, Praveen K. Khatri, Dr. Anil K. Sinha and Dr. Bir Sain

      Article first published online: 20 AUG 2010 | DOI: 10.1002/cctc.201000121

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      Re-loaded: A covalently immobilized mesoporous silica-supported oxo–rhenium catalyst, in which the oxo–rhenium species is chemically bonded to the support to prevent leaching is prepared and found to be an efficient and recyclable catalyst for the direct synthesis of nitrones through condensation/oxidation of aldehydes and primary amines, using urea–hydrogen peroxide as an oxidant.

    4. Decomposition of Formic Acid Catalyzed by a Phosphine-Free Ruthenium Complex in a Task-Specific Ionic Liquid (pages 1265–1270)

      Jackson D. Scholten, Dr. Martin H. G. Prechtl and Prof. Dr. Jairton Dupont

      Article first published online: 2 AUG 2010 | DOI: 10.1002/cctc.201000119

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      Formic acid (FA) dehydrogenation is catalyzed by a phosphine-free Ru complex in an amine-functionalized ionic liquid (IL) at 80 °C (TOFs up to 1540 h−1). Preliminary kinetic insights, the activation energy of the process, and the ionic organometallic species involved in the transformation are also determined. Significant catalytic activity was observed during recycles, indicating the system's potential for hydrogen gas production.

    5. Telomerization of Myrcene and Catalyst Separation by Thermomorphic Solvent Systems (pages 1271–1277)

      Prof. Arno Behr, Leif Johnen and Andreas J. Vorholt

      Article first published online: 29 JUL 2010 | DOI: 10.1002/cctc.201000116

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      Lord have myrcene: The first telomerization of the monoterpene myrcene catalyzed by palladium complexes is demonstrated by using thermomorphic solvent systems. The reaction is carried out under monophasic conditions, and cooling down after reaction gives rise to a liquid two-phase system, which allows easy catalyst separation.

    6. Secondary Phosphane Oxides as Preligands in Rhodium-Catalyzed Hydroformylation (pages 1278–1285)

      Dr. Andrea Christiansen, Dr. Chuanzhao Li, Dr. Marc Garland, Dr. Detlef Selent, Prof. Dr. Ralf Ludwig, Dr. Robert Franke and Prof. Dr. Armin Börner

      Article first published online: 16 AUG 2010 | DOI: 10.1002/cctc.201000114

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      SPOs it's a ligand: Aryl-substituted secondary phosphane oxides (SPOs) have been successfully tested as preligands in rhodium-catalyzed hydroformylation, forming active hydroformylation catalysts through their phosphinous acid tautomers. Furthermore, proof is given that noncoordinated SPOs readily react with product aldehydes to form α-hydroxyphosphinic acids.

    7. Catalytic Aerobic Dehydrogenative Coupling of Primary Alcohols and Water to Acids Promoted by a Rhodium(I) Amido N-Heterocyclic Carbene Complex (pages 1286–1295)

      Samuel Annen, Dr. Theo Zweifel, Dr. Federica Ricatto and Prof. Dr. Hansjörg Grützmacher

      Article first published online: 10 SEP 2010 | DOI: 10.1002/cctc.201000100

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      As good acid gets: With a RhI amido olefin complex with an N-heterocyclic carbene ligand as catalyst, the chemoselective aerobic oxidation of primary alcohols to the corresponding carboxylic acids proceeds in aqueous alkaline medium with good to moderate yields under mild conditions. Dimethylsulfoxide serves as stoichiometric co-oxidant.

    8. Green Catalytic Baeyer–Villiger Oxidation with Hydrogen Peroxide in Water Mediated by PtII Catalysts (pages 1296–1302)

      Alessandra Cavarzan, Dr. Alessandro Scarso, Dr. Paolo Sgarbossa, Prof. Rino A. Michelin and Prof. Giorgio Strukul

      Article first published online: 21 JUL 2010 | DOI: 10.1002/cctc.201000088

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      BV wonder: Baeyer–Villiger oxidation of cyclic ketones with 35 % hydrogen peroxide as a green oxidant mediated by monomeric PtII complexes bearing alkyl diphosphines greatly benefits from the employment of water with anionic surfactants. Under such conditions, the reaction shows enhanced catalytic activity compared to that with organic solvents.

    9. Pt Nanoparticles Supported on Highly Dispersed Alumina Coated inside SBA-15 for Enantioselective Hydrogenation (pages 1303–1311)

      Hongna Wang, Dr. Xiaohong Li, Prof. Yi Meng Wang and Prof. Peng Wu

      Article first published online: 7 JUL 2010 | DOI: 10.1002/cctc.201000081

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      Everything's aluminated: A series of Al2O3@SBA-15 composites with different Al2O3 loadings are prepared by a solvent-free solid-state grinding method. The composites retain the mesostructure of SBA-15 and the alumina is uniformly coated inside the mesopores. Furthermore, the Al2O3@SBA-15 composites serve as remarkable supports for Pt nanoparticle catalysts in the enantioselective hydrogenation of ethyl pyruvate.

    10. Cu Nanoparticles in PEG: A New Recyclable Catalytic System for N-Arylation of Amines with Aryl Halides (pages 1312–1317)

      Prof. Mazaahir Kidwai, Neeraj Kumar Mishra, Saurav Bhardwaj, Anwar Jahan, Ajeet Kumar and Dr. Subho Mozumdar

      Article first published online: 21 JUL 2010 | DOI: 10.1002/cctc.201000062

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      Cu around: A new protocol for the N-arylation of aryl halides with anilines using Cu nanoparticles in PEG400 as an efficient and reusable catalytic system has been developed. The reaction does not require any cocatalyst. The present methodology offers several advantages, such as excellent yields, short reaction times, and milder reaction conditions.

    11. Silica-Encapsulated Pd Nanoparticles as a Regenerable and Sintering-Resistant Catalyst (pages 1318–1324)

      Arnold J. Forman, Dr. Jung-Nam Park, Dr. Wei Tang, Dr. Yong-Sheng Hu, Prof. Galen D. Stucky and Prof. Eric W. McFarland

      Article first published online: 7 JUL 2010 | DOI: 10.1002/cctc.201000015

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      In silica catalysis: In comparison to a conventional Pd catalyst deposited on the outside of an identical silica support (Pd/SiO2), silica-encapsulated Pd (Pd@SiO2) shows higher catalytic activity and stability and is readily regenerated without severe Pd sintering over multiple reaction and regeneration cycles for acetylene hydrogenation as the test reaction.

  8. Preview

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Highlights
    7. Communications
    8. Full Papers
    9. Preview
    1. Preview: ChemCatChem 11/2010 (page 1327)

      Article first published online: 5 OCT 2010 | DOI: 10.1002/cctc.201090042

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