ChemCatChem

Cover image for Vol. 2 Issue 11

November 15, 2010

Volume 2, Issue 11

Pages 1329–1487

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Review
    7. Minireview
    8. Highlights
    9. Communications
    10. Full Papers
    11. Preview
    1. Cover Picture: Aqueous-Phase Hydrogenation of Acetic Acid over Transition Metal Catalysts (ChemCatChem 11/2010) (page 1329)

      Hakan Olcay, Dr. Lijun Xu, Dr. Ye Xu and Prof. George W. Huber

      Article first published online: 9 NOV 2010 | DOI: 10.1002/cctc.201090043

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      The cover picture shows the conversion of acetic acid to ethanol through the formation of acetyl over metal particles. In the combined experimental and theoretical study reported by Xu, Huber et al. on p. 1420 ff., high activity and selectivity are obtained over supported metal catalysts, especially Ru, at mild temperature in aqueous phase. DFT calculations suggest that C–O bond scission to form acetyl is a key step in the reaction. A simple kinetic model captures the activity trend across the different metals, allowing the catalytic activity for acetic acid hydrogenation to be estimated based on acetyl binding energies.

  2. Editorial

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Review
    7. Minireview
    8. Highlights
    9. Communications
    10. Full Papers
    11. Preview
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      Nobel Prize Awarded for Catalysis (pages 1331–1332)

      Prof. Dr. Antonio M. Echavarren

      Article first published online: 9 NOV 2010 | DOI: 10.1002/cctc.201000370

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Review
    7. Minireview
    8. Highlights
    9. Communications
    10. Full Papers
    11. Preview
    1. Graphical Abstract: ChemCatChem 11/2010 (pages 1333–1338)

      Article first published online: 9 NOV 2010 | DOI: 10.1002/cctc.201090044

  4. News

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

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Review
    7. Minireview
    8. Highlights
    9. Communications
    10. Full Papers
    11. Preview
    1. Highlights of Transition Metal-Catalyzed Asymmetric Hydrogenation of Imines (pages 1346–1371)

      Dr. Nicolas Fleury-Brégeot, Verónica de la Fuente, Prof. Dr. Sergio Castillón and Prof. Dr. Carmen Claver

      Article first published online: 16 AUG 2010 | DOI: 10.1002/cctc.201000078

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      Imine business: An important method for the preparation of chiral imines, an important synthetic intermediate, is the asymmetric hydrogenation of C[DOUBLE BOND]N double bonds using chiral transition metal complexes as catalysts. In recent years, interest in this reaction has grown considerably, resulting in more efficient processes and higher selectivities. In this Review, important recent advances are discussed.

  6. Minireview

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Review
    7. Minireview
    8. Highlights
    9. Communications
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    1. Multicatalysis: Advancing Synthetic Efficiency and Inspiring Discovery (pages 1373–1380)

      Lisa M. Ambrosini and Prof. Tristan H. Lambert

      Article first published online: 17 SEP 2010 | DOI: 10.1002/cctc.200900323

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      Cutting out the middle man: Reaction processes involving the execution of multiple catalytic reactions in a single flask, without intermittent workup or purification, have become increasingly prevalent in recent years. This Minireview discusses some recent examples of multicatalytic processes.

  7. Highlights

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Review
    7. Minireview
    8. Highlights
    9. Communications
    10. Full Papers
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    1. The Aminohydroxylation of Alkenes Breaks New Ground (pages 1381–1383)

      Christiane E. I. Knappke and Dr. Axel Jacobi von Wangelin

      Article first published online: 26 AUG 2010 | DOI: 10.1002/cctc.201000255

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      Iron & copper: Impressive developments have recently been made in the field of direct aminohydroxylation of olefins for the synthesis of versatile β-amino alcohol building blocks. Oxaziridines as new sources of both N and O atoms exhibit excellent reactivity and substrate scope under copper and iron catalysis. The choice of catalyst governs regiocontrol in the addition to olefins. Best selectivities have been achieved with styrenes and 1,3-dienes.

    2. Functionalized Grignard Reagents in Kumada Cross-Coupling Reactions (pages 1384–1386)

      Dr. Javier Adrio and Prof. Dr. Juan C. Carretero

      Article first published online: 16 AUG 2010 | DOI: 10.1002/cctc.201000237

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      Hakuna Kumada: Several efficient Kumada cross-coupling protocols of functionalized arylmagnesium halides and functionalized aryl and alkyl halides have been recently reported, including the first examples of the catalytic asymmetric Kumada coupling of racemic secondary alkyl halides. These procedures dramatically improve the synthetic potential of the Kumada cross-coupling reaction.

    3. Reactions within Molecular Single Crystals of Inorganic and Organometallic Compounds: Recent Advances and Implications for Catalysis (pages 1387–1389)

      Dr. Christian M. Frech

      Article first published online: 9 NOV 2010 | DOI: 10.1002/cctc.201000222

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      Find the answer within: Transformations within molecular single crystals of organometallic compounds are very rare and usually involve (reversible) loss of solvent molecules or ligands. A great stride forward in the field of such transformations was recently made, involving the first selective catalytic transformation within single crystals, which neither was on surface or surface sites, nor in solution.

  8. Communications

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Review
    7. Minireview
    8. Highlights
    9. Communications
    10. Full Papers
    11. Preview
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      Thermal Activation of Methane by Diatomic Metal Oxide Radical Cations: PbO+⋅ as One of the Missing Pieces (pages 1391–1394)

      Dr. Xinhao Zhang and Prof. Dr. Helmut Schwarz

      Article first published online: 26 AUG 2010 | DOI: 10.1002/cctc.201000259

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      Missing in action: Based on the high computed hydrogen atom affinities and the oxygen-centered radical characters, group IVA metal monoxide radical cations are predicted to be the missing pieces in the thermal activation of methane, and combined experimental and computational studies show that the group IVA metal oxide PbO+⋅ is indeed capable of abstracting a hydrogen atom from methane at room temperature.

    2. Dimethoxydibenzophosphepine: An Axially Chiral Monophosphane for Efficient Asymmetric Catalysis (pages 1395–1398)

      Dr. Elisabetta Alberico, Dr. Satyajit Karandikar and Prof. Serafino Gladiali

      Article first published online: 26 AUG 2010 | DOI: 10.1002/cctc.201000252

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      A novel axially chiral phosphepine constructed on a diphenyl template is prepared in four steps. Resolution with the aid of menthyl chloroformate at the intermediate bisphenol stage affords the pure (R)-enantiomer, the cationic RhI complex of which is an active and stereoselective catalyst for the hydrogenation and transfer hydrogenation of α,β-unsaturated acid derivatives with 94–96 % ee.

    3. Ultra-Low-Temperature Water–Gas Shift Catalysis using Supported Ionic Liquid Phase (SILP) Materials* (pages 1399–1402)

      Sebastian Werner, Dr. Normen Szesni, Melanie Kaiser, Dr. Richard W. Fischer, Dr. Marco Haumann and Prof. Dr. Peter Wasserscheid

      Article first published online: 9 NOV 2010 | DOI: 10.1002/cctc.201000245

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      SILP inside the eye of your mind: A new class of water–gas shift catalyst system that outperforms commercial shift catalysts under ultra-low-temperature real gas conditions (T<160 °C) has been developed. The new catalysts consist of [{RuCl2(CO)3}2] dissolved in a chloride ionic liquid and dispersed on a porous basic support using the SILP approach. Its robustness and recyclability make it highly attractive for industrial hydrogen production.

    4. Oxidative Nickel–Air Catalysis in C[BOND]H Arylation: Direct Cross-Coupling of Azoles with Arylboronic Acids using Air as Sole Oxidant (pages 1403–1406)

      Hitoshi Hachiya, Dr. Koji Hirano, Prof. Dr. Tetsuya Satoh and Prof. Dr. Masahiro Miura

      Article first published online: 16 AUG 2010 | DOI: 10.1002/cctc.201000223

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      Something in the air: An efficient Ni–air catalyst system for the direct C[BOND]H arylation of azoles has been developed. The catalytic system is simple and practical, and shows the high potential of nickel–oxygen catalysis in the field of direct C[BOND]H functionalization chemistry.

    5. Selective Hydrolysis of Diphenyl Ether in Supercritical Water Catalyzed by Alkaline Carbonates (pages 1407–1410)

      Dr. Virginia M. Roberts, Dr. Richard T. Knapp, Dr. Xuebing Li and Prof. Dr. Johannes A. Lercher

      Article first published online: 17 SEP 2010 | DOI: 10.1002/cctc.201000181

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      Supercritical thinking: Diphenyl ether (DPE) can be hydrolyzed catalytically in supercritical water with high selectivity and efficiency using zirconia-supported potassium carbonate. The product spectrum of DPE treatment in supercritical water can be adjusted by increasing the density of supercritical water.

    6. Synthesis of Secondary Amines by Iron-Catalyzed Reductive Amination (pages 1411–1415)

      Dr. Stephan Enthaler

      Article first published online: 9 NOV 2010 | DOI: 10.1002/cctc.201000180

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      Iron awe: For the first time, a straightforward reductive amination procedure based on iron catalysts is presented. Excellent performance is demonstrated by a system composed of FeCl3 and poly(methylhydrosiloxane) as a cheap hydride source under non-inert conditions. The procedure is also versatile, allowing for the amination of a wide range of substrates in yields up to 99 %.

    7. Hydrothermal Method Prepared Ce-P-O Catalyst for the Selective Catalytic Reduction of NO with NH3 in a Broad Temperature Range (pages 1416–1419)

      Fei Li, Yibo Zhang, Dehai Xiao, Deqiang Wang, Xiqiang Pan and Prof. Dr. Xiangguang Yang

      Article first published online: 18 AUG 2010 | DOI: 10.1002/cctc.201000179

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      NO your enemy: A new type of Ce-P-O catalyst has been developed for the selective catalytic reduction of NO with NH3 (NH3-SCR). The Ce-P-O catalyst prepared by a hydrothermal method shows excellent deNOx activity and prominent resistance to the poisonous effect of K2O and SO2/H2O in a broad temperature range.

    8. Aqueous-Phase Hydrogenation of Acetic Acid over Transition Metal Catalysts (pages 1420–1424)

      Hakan Olcay, Dr. Lijun Xu, Dr. Ye Xu and Prof. George W. Huber

      Article first published online: 9 NOV 2010 | DOI: 10.1002/cctc.201000134

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      Vision in scission: Catalytic hydrogenation of acetic acid to ethanol has been carried out in aqueous phase on several metals, with ruthenium being the most active and selective. DFT calculations suggest that the initial C[BOND]O bond scission yielding acetyl is the key step and that the intrinsic reactivity of the metals accounts for the observed activity.

  9. Full Papers

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Review
    7. Minireview
    8. Highlights
    9. Communications
    10. Full Papers
    11. Preview
    1. Structure–Activity Relationships of Oligocationic, Ammonium-Functionalized Triarylphosphines as Ligands in the Pd-Catalyzed Suzuki–Miyaura Reaction (pages 1425–1437)

      Dr. Dennis J. M. Snelders, Cornelis van der Burg, Dr. Martin Lutz, Prof. Dr. Anthony L. Spek, Prof. Dr. Gerard van Koten and Prof. Dr. Robertus J. M. Klein Gebbink

      Article first published online: 1 SEP 2010 | DOI: 10.1002/cctc.201000232

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      Ligands in charge: The catalytic activity in the Pd-catalyzed Suzuki–Miyaura reaction upon the use of oligocationic, ammonium-functionalized triarylphosphine ligands is governed by the number of cationic charges in the ligand structure, rather than by their steric or electronic properties. Increasing the number of charges increases the preference for the formation of coordinatively unsaturated phosphine–palladium species, which leads to a higher catalytic activity through faster catalyst activation.

    2. Aerobic Oxidation of Benzyl Amines to Benzyl Imines Catalyzed by Metal–Organic Framework Solids (pages 1438–1443)

      Dr. Amarajothi Dhakshinamoorthy, Dr. Mercedes Alvaro and Prof. Dr. Hermenegildo Garcia

      Article first published online: 19 AUG 2010 | DOI: 10.1002/cctc.201000175

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      The frame game:N-Hydroxyphthalimide (NHPI) incorporated on an FeIII-based metal–organic framework [NHPI/Fe(BTC); BTC=1,3,5-benzenetricarboxylate] is used as a heterogeneous catalyst for the aerobic oxidation of benzylamine and its derivatives to their corresponding benzyl imines under neat conditions with molecular oxygen as the only oxidant at 100 °C.

    3. Sonogashira Coupling Catalyzed by Gold Nanoparticles: Does Homogeneous or Heterogeneous Catalysis Dominate? (pages 1444–1449)

      Dr. Georgios Kyriakou, Simon K. Beaumont, Dr. Simon M. Humphrey, Claudia Antonetti and Prof. Richard M. Lambert

      Article first published online: 16 AUG 2010 | DOI: 10.1002/cctc.201000154

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      Some kind of 'geneous: Gold nanoparticles catalyze the Sonogashira cross coupling of iodobenzene with phenylacetylene. Large particles are much more selective than small ones and gold species leached into solution are catalytically inert, consistent with the view that the dominant reaction pathway is heterogeneous.

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      DFT-Based Coverage-Dependent Model of Pt-Catalyzed NO Oxidation (pages 1450–1460)

      Rachel B. Getman and William F. Schneider

      Article first published online: 26 AUG 2010 | DOI: 10.1002/cctc.201000146

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      Coverage control: Because of its small ΔHrxn (−60 kJ mol−1), catalytic NO oxidation to NO2 favors products only at high O2 pressures and high coverages of catalyst O. DFT calculations on Pt(111) models show that O2 dissociation barriers are more strongly coverage dependent than are O[BOND]NO bond formation kinetics, indicating the former are rate limiting at relevant conditions.

    5. Recyclable Dirhodium Catalysts Embedded in Nanoporous Surface-Functionalized Organosilica Hosts for Carbenoid-Mediated Cyclopropanation Reactions (pages 1461–1466)

      Evgeny V. Dikarev, D. Krishna Kumar, Alexander S. Filatov, Abhishek Anan, Youwei Xie, Tewodros Asefa and Marina A. Petrukhina

      Article first published online: 16 AUG 2010 | DOI: 10.1002/cctc.201000142

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      An efficient synthetic strategy to immobilize dirhodium(II,II) paddlewheel complexes of varied electrophilicity into a nanoporous organosilica host has been developed. The resulting rhodium- containing solid products have been evaluated as catalysts in intermolecular cyclopropanation reactions of styrene with ethyl diazoacetate and methyl phenyldiazoacetate.

    6. Acceleration of the Rate of the Heck Reaction through UV- and Visible-Light-Induced Palladium(II) Reduction (pages 1467–1476)

      Margaret Anne Fredricks, Dr. Markus Drees and Prof. Dr. Klaus Köhler

      Article first published online: 16 AUG 2010 | DOI: 10.1002/cctc.201000137

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      The speed of light: UV and visible light increase the rate of the Heck reaction with homogeneous and heterogeneous PdII catalysts precursors. PdII reduction is significantly faster (minutes versus hours) under light irradiation than in the dark and the same species are active with and without irradiation. These species include Pd halides, which can undergo PdII reduction, as shown by DFT calculations and UV/Vis spectroscopy.

    7. A Covalently Immobilized Triphenylphosphine Rhodium Complex: Synthesis, Characterization, and Application in Catalytic Olefin Hydrogenation (pages 1477–1482)

      Lei Wang, Prof. Dr. Mingjun Jia, Dr. Sankaranarayanapillai Shylesh, Thomas Philippi, Dr. Andreas Seifert, Prof. Dr. Stefan Ernst, Dr. Anand Pal Singh and Prof. Dr. Werner R. Thiel

      Article first published online: 20 AUG 2010 | DOI: 10.1002/cctc.201000133

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      Covalently grafting a trimethoxysilane functionalized triphenylphosphine rhodium(I) complex to the silica surface of a mesoporous SBA-15 support gives a highly active, selective, stable, and recyclable catalyst for olefin hydrogenation.

  10. Preview

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Review
    7. Minireview
    8. Highlights
    9. Communications
    10. Full Papers
    11. Preview
    1. You have free access to this content
      Preview: ChemCatChem 12/2010 (page 1487)

      Article first published online: 9 NOV 2010 | DOI: 10.1002/cctc.201090046

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