Chemistry - A European Journal

Cover image for Vol. 16 Issue 31

Special Issue: Conference Issue: 3rd European Chemistry Congress, Nürnberg

August 16, 2010

Volume 16, Issue 31

Pages 9305–9691

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Concepts
    8. Reviews
    9. Minireviews
    10. Communications
    11. Full Papers
    12. Preview
    1. Cover Picture: Fullerene Derivatives That Bear Aliphatic Chains as Unusual Surfactants: Hierarchical Self-Organization, Diverse Morphologies, and Functions / Model Studies in Heterogeneous Catalysis / Functional Hybrid Materials with Polymer Nanoparticles as Templates / Systems Chemistry Approach in Organic Photovoltaics / Unraveling the Mechanism of the Singlet Oxygen Ene Reaction: Recent Computational and Experimental Approaches / Applied Biotransformations in Green Solvents / Nanoparticles for Cultural Heritage Conservation: Calcium and Barium Hydroxide Nanoparticles for Wall Painting Consolidation / Unifying Metal and Brønsted Acid Catalysis—Concepts, Mechanisms, and Classifications / Detection of Carbocationic Species in Zeolites: Large Crystals Pave the Way (Chem. Eur. J. 31/2010) (page 9305)

      Hidehiko Asanuma, Hongguang Li, Takashi Nakanishi, Helmuth Möhwald, H.-J. Freund, Anitha Ethirajan, Katharina Landfester, Frank Würthner, Klaus Meerholz, Mariza N. Alberti, Michael Orfanopoulos, María J. Hernáiz, Andrés R. Alcántara, José I. García, José V. Sinisterra, Rodorico Giorgi, Moira Ambrosi, Nicola Toccafondi, Piero Baglioni, Magnus Rueping, Rene M. Koenigs, Iuliana Atodiresei, Eli Stavitski, Evgeny A. Pidko, Marianne H. F. Kox, Emiel J. M. Hensen, Rutger A. van Santen and Bert M. Weckhuysen

      Article first published online: 12 AUG 2010 | DOI: 10.1002/chem.201090152

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      The cover picture shows the frontispieces of the Concept, Review, and Minireview articles published in this issue, highlighting the diverse range of chemistry that will be covered at the 3rd European Chemistry Congress in Nürnberg. They represent five of the seven main symposium topics: Innovative Materials, Catalysis, Molecular Life Sciences, Analysis, Manipulation and Simulation, and Advances in Organic and Inorganic Chemistry. In the top row from left to right: H. Möhwald, T. Nakanishi et al. (page 9330 ff.), H.-J. Freund (page 9384 ff.), and K. Landfester and A. Ethirajan (page 9398 ff.). In the middle row from left to right: F. Würthner and K. Meerholz (page 9366 ff), M. Orfanopoulos and M. N. Alberti (page 9414 ff), and J. V. Sinisterra et al. (page 9422 ff.). In the bottom row from left to right: P. Baglioni et al. (page 9374 ff), M. Rueping et al. (page 9350 ff.), and Bert Weckhuysen et al. (page 9340 ff.) (Cover designed by Heulwen M. M. Price).

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Concepts
    8. Reviews
    9. Minireviews
    10. Communications
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    1. Inside Cover: (Chem. Eur. J. 31/2010) (page 9306)

      Article first published online: 12 AUG 2010 | DOI: 10.1002/chem.201090153

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      ChemistryViews.org is a comprehensive free-to-view news and information site with an associated magazine, ChemViews, provided by ChemPubSoc Europe and its publisher, Wiley-VCH. The new site enhances ChemPubSoc Europe's and Wiley-VCH's suite of market-leading peer-reviewed journals like Chemistry—A European Journal. ChemViews offers news, commentary, opinion, and additional feature material from leading authors to the global chemistry community. Sign in for a free newsletter at www.ChemViews.org (cover by Heulwen M. M. Price).

  3. Editorial

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    7. Concepts
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    9. Minireviews
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  4. Graphical Abstract

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    4. Editorial
    5. Graphical Abstract
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    7. Concepts
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    1. Graphical Abstract: Chem. Eur. J. 31/2010 (pages 9313–9323)

      Article first published online: 12 AUG 2010 | DOI: 10.1002/chem.201090154

  5. News

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  6. Concepts

    1. Top of page
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    4. Editorial
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    7. Concepts
    8. Reviews
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    1. Hydrophobic Surfactants

      Fullerene Derivatives That Bear Aliphatic Chains as Unusual Surfactants: Hierarchical Self-Organization, Diverse Morphologies, and Functions (pages 9330–9338)

      Hidehiko Asanuma, Hongguang Li, Takashi Nakanishi and Helmuth Möhwald

      Article first published online: 25 JUN 2010 | DOI: 10.1002/chem.201000835

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      Uncommonly good: An unusual amphiphile composed strictly of hydrophobic units, fullerene (C60), and long aliphatic chains behaves as an uncommon surfactant in organic media. Slight differences in the polarity and the chemical nature among these groups allow them to exhibit amphiphilicity. Their material aspects were also investigated (see graphic).

    2. Heterogeneous Catalysis

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      Detection of Carbocationic Species in Zeolites: Large Crystals Pave the Way (pages 9340–9348)

      Eli Stavitski, Evgeny A. Pidko, Marianne H. F. Kox, Emiel J. M. Hensen, Rutger A. van Santen and Bert M. Weckhuysen

      Article first published online: 6 JUL 2010 | DOI: 10.1002/chem.201000995

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      Molecules, line up! Synchrotron-based IR and UV/Vis microspectroscopic data and complementary theoretical calculations can be used to unambiguously identify transient carbocationic species generated in the acid-catalyzed oligomerization of styrene derivatives within ZSM-5. Polarization dependence of the IR and UV/Vis spectra is rationalized in terms of the vibrational and electronic transitions occurring in the confined molecules (see figure).

    3. Domino Reactions

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      Unifying Metal and Brønsted Acid Catalysis—Concepts, Mechanisms, and Classifications (pages 9350–9365)

      Magnus Rueping, Rene M. Koenigs and Iuliana Atodiresei

      Article first published online: 21 JUL 2010 | DOI: 10.1002/chem.201001140

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      Combining acids and metals! The combination of chiral Brønsted acids and achiral or chiral transition-metal complexes emerged as a new strategy in asymmetric synthesis. The merged catalytic approach provides practical synthetic protocols that enable the synthesis of a broad range of compounds in a highly enantioselective fashion (see graphic).

    4. Organic Photovoltaics

      Systems Chemistry Approach in Organic Photovoltaics (pages 9366–9373)

      Frank Würthner and Klaus Meerholz

      Article first published online: 19 JUL 2010 | DOI: 10.1002/chem.201001153

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      Get organized! The recent successful utilization of highly dipolar merocyanine dyes in bulk heterojunction organic photovoltaic materials provides a convincing example for illustrating the importance of supramolecular organization principles in multifunctional organic materials.

    5. Nanotechnology

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      Nanoparticles for Cultural Heritage Conservation: Calcium and Barium Hydroxide Nanoparticles for Wall Painting Consolidation (pages 9374–9382)

      Rodorico Giorgi, Moira Ambrosi, Nicola Toccafondi and Piero Baglioni

      Article first published online: 23 JUL 2010 | DOI: 10.1002/chem.201001443

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      Paint the town red! Sulfation of wall paintings produces flaking and powdering of the paint layer. The combined action of calcium and barium hydroxide nanoparticles provides complete immobilisation of salts, and a durable re-cohesion effect on the paint layer (see graphic). The original carbonation process is re-generated to perfectly match the original physicochemical properties of the painting.

  7. Reviews

    1. Top of page
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    4. Editorial
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    1. Heterogeneous Catalysis

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      Model Studies in Heterogeneous Catalysis (pages 9384–9397)

      H.-J. Freund

      Article first published online: 28 JUL 2010 | DOI: 10.1002/chem.201001724

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      Scratching the surface: In this Review models for heterogeneous catalysis are discussed based on a surface-science approach (see figure). It is shown that models catching part of the complexity of the real system, which is connected with the finite size of active components and the flexibility of the arrangement of atoms in the active component, play an important part in determining the activity and selectivity of the system.

    2. Biomimetic Mineralization

      Functional Hybrid Materials with Polymer Nanoparticles as Templates (pages 9398–9412)

      Anitha Ethirajan and Katharina Landfester

      Article first published online: 26 JUL 2010 | DOI: 10.1002/chem.201001477

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      Close to the bone! Polymer nanoparticles can be used as versatile biomimetic templates to produce hybrid particles by employing either the volume or the surface of the polymer nanoparticle as templates (see picture). Such a concept is used to produce nanoparticles containing the bone mineral hydroxyapatite as the inorganic material. These particles could find application as regenerative fillers or as a scaffold for nucleation and growth of new bone material.

  8. Minireviews

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    1. Reaction Mechanisms

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      Unraveling the Mechanism of the Singlet Oxygen Ene Reaction: Recent Computational and Experimental Approaches (pages 9414–9421)

      Mariza N. Alberti and Michael Orfanopoulos

      Article first published online: 9 JUL 2010 | DOI: 10.1002/chem.201000752

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      Concerted or stepwise? Recently, the mechanism of the singlet oxygen ene reaction has been a subject of renewed interest, particularly, whether the reaction is concerted or involves discrete intermediates. The majority of experimental and computational studies support a traditional stepwise mechanism involving a perepoxide-like intermediate (see scheme). This Minireview highlights some of the classical and most recent theoretical and experimental results relating to the mechanism of the 1O2 ene oxyfunctionalization.

    2. Green Chemistry

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      Applied Biotransformations in Green Solvents (pages 9422–9437)

      María J. Hernáiz, Andrés R. Alcántara, José I. García and José V. Sinisterra

      Article first published online: 28 JUL 2010 | DOI: 10.1002/chem.201000798

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      The future is bio, the future is green: Interest in implementing sustainable industrial technologies has propelled the use of biocatalysts (enzymes or cells), leading to high chemo-, regio- and stereoselectivity under mild conditions. We focus on different attempts to combine the valuable properties of green solvents with the advantages of using biocatalysts for developing cleaner synthetic processes (see figure).

  9. Communications

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    1. Natural Products

      First Enantioselective Synthesis of the Diazatricyclic Core of Madangamine Alkaloids (pages 9438–9441)

      Mercedes Amat, Maria Pérez, Stefano Proto, Teresa Gatti and Joan Bosch

      Article first published online: 8 APR 2010 | DOI: 10.1002/chem.201000421

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      En route to madangamines: A unified strategy has been developed for the enantioselective assembly of functionalized diazatricyclic synthetic precursors of madangamines (see scheme; Bn=benzyl, Boc=tert-butoxycarbonyl, Mbs=para-methoxybenzenesulfonyl).

    2. Asymmetric Synthesis

      Lewis Base Catalyzed Enantioselective Allylation of α,β-Unsaturated Aldehydes (pages 9442–9445)

      Aneta Kadlčíková, Irena Valterová, Lucie Ducháčková, Jana Roithová and Martin Kotora

      Article first published online: 20 JUL 2010 | DOI: 10.1002/chem.201001523

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      Being selective: The catalytic allylation of α,β-unsaturated aldehydes with allyltrichlorosilane in the presence of chiral 3,3′-unsymmetrically substituted bis(tetrahydroisoquinoline) N,N-dioxides was explored. The allylation of various aldehydes proceeded under mild reaction conditions (−78 °C) with high yields and enantioselectivity (see scheme). This allylation was applied in the synthesis of (S)-(−)-goniothalamin.

    3. Uranium Complexes

      UIII-Induced Reductive Co-Coupling of NO and CO to Form UIV Cyanate and Oxo Derivates (pages 9446–9448)

      Alistair S. P. Frey, F. Geoffrey N. Cloke, Martyn P. Coles and Peter B. Hitchcock

      Article first published online: 20 JUL 2010 | DOI: 10.1002/chem.201001231

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      CO and NO give NCO and O! Sequential treatment of [U(η-C8H6{SiiPr3-1,4}2)(η-Cp*)] with CO followed by NO (or vice versa) affords a mixture of the bridging cyanate complex [{U(η-C8H6{SiiPr3-1,4}2)(η-Cp*)}2(μ-OCN)2] and the bridging oxo complex [{U(η-C8H6{SiiPr3-1,4}2)(η-Cp*)}2(μ-O)], both of which have been structurally characterised (see scheme).

    4. Ring-Closing Metathesis

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      A Simple and Effective Co-Catalyst for Ring-Closing Enyne Metathesis Using Grubbs I type Catalysts: A Practical Alternative to “Mori’s Conditions” (pages 9449–9452)

      Guy C. Lloyd-Jones, Alan J. Robinson, Laurent Lefort and Johannes G. de Vries

      Article first published online: 21 JUL 2010 | DOI: 10.1002/chem.201001510

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      “Catch-and-release”: Simple alk-1-enes are effective at liberating buta-1,3-dienes from vinyl alkylidene ruthenium complexes, as well as undergoing alkene–alkylidene exchange with enyne substrates to regenerate the alk-1-ene. This ability to “catch-and-release” ruthenium alkylidenes allows alk-1-enes higher than ethylene (“Mori's conditions”) to be used as a co-catalysts in terminal enyne metathesis with the Grubbs generation I complex (L=PCy3).

    5. Asymmetric Synthesis

      Asymmetric Synthesis of 4-Amino-4H-Chromenes by Organocatalytic Oxa-Michael/Aza-Baylis–Hillman Tandem Reactions (pages 9453–9456)

      José Alemán, Alberto Núñez, Leyre Marzo, Vanesa Marcos, Cuauhtémoc Alvarado and José Luis García Ruano

      Article first published online: 26 JUL 2010 | DOI: 10.1002/chem.201001293

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      Quick off the mark! In this work we present the first highly enatioselective oxa-Michael/aza-Baylis–Hillman tandem reaction between 2-alkynals and salicyl N-tosylimine leading to optically active 4-amino-4H-chromenes (see scheme). This reaction takes place in less than 2 h with high yields and excellent enantioselectivities.

      Corrected by:

      Corrigendum: Corrigendum: Asymmetric Synthesis of 4-Amino-4H-Chromenes by Organocatalytic Oxa-Michael/Aza-Baylis–Hillman Tandem Reactions

      Vol. 17, Issue 44, 12228, Article first published online: 17 OCT 2011

    6. Hypervalent Iodine

      Ethynyl-1,2-benziodoxol-3(1 H)-one (EBX): An Exceptional Reagent for the Ethynylation of Keto, Cyano, and Nitro Esters (pages 9457–9461)

      Davinia Fernández González, Jonathan P. Brand and Jérôme Waser

      Article first published online: 19 JUL 2010 | DOI: 10.1002/chem.201001539

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      Hot alkyne! The in situ generation of ethynyl-1,2-benziodoxol-3(1H)-one (EBX) from a silyl-protected reagent by using TBAF is reported. EBX displayed exceptional acetylene transfer ability onto stabilized enolates (see scheme), even at −78 °C. The mild reaction conditions allowed the first ethynylation reactions of linear keto, cyano, and nitro esters in high yields to give all-carbon quaternary centers or non-natural amino acids after selective reduction of the nitro group.

    7. Nanoparticles

      Growing Au/Ag Nanoparticles within Microgel Colloids for Improved Surface-Enhanced Raman Scattering Detection (pages 9462–9467)

      Rafael Contreras-Cáceres, Isabel Pastoriza-Santos, Ramón A. Alvarez-Puebla, Jorge Pérez-Juste, Antonio Fernández-Barbero and Luis M. Liz-Marzán

      Article first published online: 19 JUL 2010 | DOI: 10.1002/chem.201001261

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      Microgel grow-bags: Surface-enhanced Raman scattering (SERS)-active bimetallic core–shell spheres can be grown inside poly(N-isopropylacrylamide) (pNIPAM) microgels (see figure).

  10. Full Papers

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    4. Editorial
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    1. Platinum

      Proton-Transfer Reactions on Hexanuclear Platinum Clusters: Reversible Heterolytic Cleavage of H2 and C[BOND]H Activation Affording a Linear, Cluster-Containing Polymer (pages 9468–9477)

      Piero Leoni, Lorella Marchetti, Veronica Bonuccelli, Swagat K. Mohapatra, Alberto Albinati and Silvia Rizzato

      Article first published online: 22 JUN 2010 | DOI: 10.1002/chem.201000809

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      Chemical clusters: The reversible reaction of Brønsted acids, HA, with the hexanuclear dihydride {Pt6}H2 ({Pt6}=Pt6(μ-PtBu2)(CO)4) affords anion-bonded {Pt6}A2, which reacts with dimethoxyethane to give the linear, cluster-containing polymer [Pt6(μ-PtBu2)4(CO)4(CH2OCH2CH2OCH2)]x (see figure).

    2. Organocatalysis

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      Asymmetric One-Pot Sequential Organo- and Gold Catalysis for the Enantioselective Synthesis of Dihydropyrrole Derivatives (pages 9478–9484)

      David Monge, Kim L. Jensen, Patrick T. Franke, Lennart Lykke and Karl Anker Jørgensen

      Article first published online: 2 JUL 2010 | DOI: 10.1002/chem.201001123

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      A golden combination: A direct asymmetric one-pot synthesis of optically active 2,3-dihydropyrroles from simple precursors is presented. The approach is based on a bifunctional organocatalytic Mannich-type reaction followed by AuI-catalyzed alkyne hydroamination (see scheme; TFA=trifluoroacetic acid). To highlight the synthetic potential of the accessed heterocyclic compounds, their transformation into 1-pyrrolines is presented.

    3. Alkane Functionalisation

      Mild, Single-Pot Hydrocarboxylation of Gaseous Alkanes to Carboxylic Acids in Metal-Free and Copper-Promoted Aqueous Systems (pages 9485–9493)

      Marina V. Kirillova, Alexander M. Kirillov and Armando J. L. Pombeiro

      Article first published online: 7 MAY 2010 | DOI: 10.1002/chem.201000352

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      Active alkanes: Gaseous alkanes (ethane, propane and n-butane) efficiently react with carbon monoxide and water to give selectively, in a single-pot, the corresponding carboxylic acids in a metal-free and acid-solvent-free aqueous medium, under mild conditions (see figure).

    4. Reaction Mechanisms

      DFT Investigation of the Palladium-Catalyzed Ene–Yne Coupling (pages 9494–9501)

      Signe Teuber Henriksen, David Tanner, Troels Skrydstrup and Per-Ola Norrby

      Article first published online: 19 JUL 2010 | DOI: 10.1002/chem.201001158

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      The perfect couple! The mechanism of the palladium-catalyzed intermolecular ene–yne coupling (see scheme) has been characterized by DFT. The absence of potential by-products from homocoupling could be fully rationalized.

    5. Molecular Recognition

      Active Transport of Amino Acids by a Guanidiniocarbonyl–Pyrrole Receptor (pages 9502–9510)

      Christian Urban and Carsten Schmuck

      Article first published online: 17 MAY 2010 | DOI: 10.1002/chem.201000509

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      An amphiphilic receptor (1) transports N-acetylated amino acid carboxylates across a bulk liquid membrane (see graphic). In single experiments the release of the substrate determines the transport rate, whereas in competition experiments the affinity towards the receptor is decisive. Since 1 can only bind carboxylates in its protonated form, an overall symport of the amino acid carboxylate and a proton occurs. This allows for pH gradient driven active transport of the substrate.

    6. Halogen Bonding

      Structure–Function Relationships in Liquid-Crystalline Halogen-Bonded Complexes (pages 9511–9524)

      Duncan W. Bruce, Pierangelo Metrangolo, Franck Meyer, Tullio Pilati, Carsten Präsang, Giuseppe Resnati, Giancarlo Terraneo, Stephen G. Wainwright and Adrian C. Whitwood

      Article first published online: 21 JUL 2010 | DOI: 10.1002/chem.201000717

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      Clear as liquid crystals! New liquid-crystalline materials (see figure) were prepared by self-assembly driven by halogen bonding (XB) between a range of alkoxystilbazoles (XB acceptors) and derivatives of the 4-iodotetrafluorophenyl unit (XB donors). Despite the fact that the starting materials are not mesomorphic, the dimeric, halogen-bonded complexes obtained exhibited nematic and SmA phases, depending on the length of the alkyl chains present on the components.

    7. Enzymatic Synthesis

      Enzymatic Synthesis of Enantiomerically Pure β-Amino Ketones, β-Amino Esters, and β-Amino Alcohols with Baeyer–Villiger Monooxygenases (pages 9525–9535)

      Jessica Rehdorf, Marko D. Mihovilovic, Marco W. Fraaije and Uwe T. Bornscheuer

      Article first published online: 21 JUL 2010 | DOI: 10.1002/chem.201001480

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      Nature's diversity: Kinetic resolution of structurally different aliphatic β-amino ketones was performed by using a collection of 16 different Baeyer–Villiger monooxygenases from various bacterial origins (see scheme). Excellent enantioselectivities for both normal and antipodal esters were observed and hydrolysis of Baeyer–Villiger esters yielded enantiopure β-amino alcohols.

    8. Surface Chemistry

      Contributions of Electron Microscopy to Understanding CO Adsorption on Powder Au/Ceria–Zirconia Catalysts (pages 9536–9543)

      José María Cíes, Juan José Delgado, Miguel López-Haro, Ratchaneekorn Pilasombat, José Antonio Pérez-Omil, Susana Trasobares, Serafin Bernal and José Juan Calvino

      Article first published online: 22 JUN 2010 | DOI: 10.1002/chem.201000866

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      Model behaviour: A nanostructural model for the adsorption of CO on powder Au/ceria–zirconia catalysts, under conditions relevant to catalysis, is proposed by combining electron microscopy, computer modelling (see figure) and chemical analysis. This model highlights the key role of CO spillover in the adsorption on ceria–zirconia.

    9. Specific-Ion Effects

      Sodium Effect on Self-Organization of Amphiphilic Carboxylates: Formation of Structured Micelles and Superlattices (pages 9544–9554)

      Karin Rosenlehner, Boris Schade, Christoph Böttcher, Christof M. Jäger, Timothy Clark, Frank W. Heinemann and Andreas Hirsch

      Article first published online: 23 JUL 2010 | DOI: 10.1002/chem.201001150

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      Stick together! The aggregation of amphiphilic polycarboxylates in water to structured micelles is strongly determined by the nature of the counterion. Sodium ions show the most pronounced counterion effect, favoring both intra- and intermicellar aggregation (see figure).

      Corrected by:

      Corrigendum: Corrigendum: Sodium Effect on Self-Organization of Amphiphilic Carboxylates: Formation of Structured Micelles and Superlattices

      Vol. 17, Issue 44, 12228, Article first published online: 17 OCT 2011

    10. Enantioselective Catalysis

      Enantioselective Reduction of Ketones and Imines Catalyzed by (CN-Box)ReV–Oxo Complexes (pages 9555–9562)

      Kristine A. Nolin, Richard W. Ahn, Yusuke Kobayashi, Joshua J. Kennedy-Smith and F. Dean Toste

      Article first published online: 7 JUL 2010 | DOI: 10.1002/chem.201001164

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      High-oxidation state bis-oxazoline rhenium(V)–oxo complexes (see scheme) catalyze the enantioselective reduction of ketones and imines under open-flask conditions. Additionally, the oxo complexes promote a tandem [3,3]-rearrangement–enantioselective reduction of propargyl and allenic alcohols.

    11. Synthetic Methods

      Synthesis of Small Molecules with High Scaffold Diversity: Exploitation of Metathesis Cascades in Combination with Inter- and Intramolecular Diels–Alder Reactions (pages 9563–9571)

      Catherine O'Leary-Steele, Palle J. Pedersen, Thomas James, Thomas Lanyon-Hogg, Stuart Leach, Jerome Hayes and Adam Nelson

      Article first published online: 2 JUN 2010 | DOI: 10.1002/chem.201000707

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      In search of scaffold diversity: The synthesis of a library of small molecules with high scaffold diversity is described. Initially, metathesis substrates were assembled from combinations of two or three building blocks. The range of scaffolds was extended through the subsequent exploitation of inter- and intramolecular Diels–Alder reactions. Fluorous tagging was used to facilitate the synthesis and functionalisation of the products (see scheme).

    12. Hydrogen Peroxide Epoxidation

      Olefin Epoxidation by H2O2/MeCN Catalysed by Cyclopentadienyloxidotungsten(VI) and Molybdenum(VI) Complexes: Experiments and Computations (pages 9572–9584)

      Chiara Dinoi, Marco Ciclosi, Eric Manoury, Laurent Maron, Lionel Perrin and Rinaldo Poli

      Article first published online: 21 MAY 2010 | DOI: 10.1002/chem.201000298

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      Tungsten is better: Compound [Cp*2W2O5] is 50 times more active than [Cp*2Mo2O5] for the quantitative and selective epoxidation of cyclooctene by H2O2 in acetonitrile (see scheme). A DFT study traces this difference to the greater oxophilicity of tungsten, which plays a determining role in the transition-state stabilisation.

    13. Lipopeptides

      Solid-Phase Synthesis of Lipidated Ras Peptides Employing the Ellman Sulfonamide Linker (pages 9585–9591)

      Gemma Triola, Marc Gerauer, Kristina Görmer, Lucas Brunsveld and Herbert Waldmann

      Article first published online: 20 JUL 2010 | DOI: 10.1002/chem.201001642

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      Safety catch: The solid-phase synthesis of differently lipidated peptides from the N-Ras family with the safety-catch sulfonamide linker has been established, including amino acid loading, peptide assembly and peptide release. The key step is the release of a pre-peptide from the solid support with the C-terminal amino acid methyl ester under microwave irradiation (see scheme).

    14. Push–Pull Chromophores

      Proaromaticity: Organic Charge-Transfer Chromophores with Small HOMO–LUMO Gaps (pages 9592–9605)

      Yi-Lin Wu, Filip Bureš, Peter D. Jarowski, W. Bernd Schweizer, Corinne Boudon, Jean-Paul Gisselbrecht and François Diederich

      Article first published online: 20 JUL 2010 | DOI: 10.1002/chem.201001051

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      When charge transfer meets aromaticity: Charge transfer across quinoid and expanded quinoid π spacers was found to be highly efficient in conjunction with the aromatization of the spacer units based on experimental and theoretical evidence. A push–pull tetrakis(ethynediyl)-expanded quinoid compound (see figure) represents the first proaromatic radiaannulene, featuring a 14 π-electron perimeter in the charge-transfer geometry.

    15. Iron Catalysis

      Efficient Synthesis of Biologically Interesting 3,4-Diaryl-Substituted Succinimides and Maleimides: Application of Iron-Catalyzed Carbonylations (pages 9606–9615)

      Saisuree Prateeptongkum, Katrin Marie Driller, Ralf Jackstell, Anke Spannenberg and Matthias Beller

      Article first published online: 2 JUN 2010 | DOI: 10.1002/chem.201000369

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      A novel synthetic strategy involving palladium-catalyzed Sonogashira reactions and iron-catalyzed double carbonylations allows for the synthesis of biologically interesting 3,4-diaryl-substituted succinimides and maleimides (see scheme).

    16. Total Synthesis

      Syntheses and Antibacterial Properties of iso-Platencin, Cl-iso-Platencin and Cl-Platencin: Identification of a New Lead Structure (pages 9616–9622)

      Konrad Tiefenbacher, Andreas Gollner and Johann Mulzer

      Article first published online: 18 MAY 2010 | DOI: 10.1002/chem.201000706

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      The unnatural antibiotic iso-platencin, which is about as active as natural platencin (a novel antibiotic which is active against multiresistant pathogens), but much more selective, is presented as a new antibiotic lead structure (see figure). We describe efficient syntheses of three platencin analogues of varying activities, which allow further conclusions about the pharmacophoric part of the molecule.

    17. Actinide Chemistry

      Covalency in CeIV and UIV Halide and N-Heterocyclic Carbene Bonds (pages 9623–9629)

      Polly L. Arnold, Zoë R. Turner, Nikolas Kaltsoyannis, Panagiota Pelekanaki, Ronan M. Bellabarba and Robert P. Tooze

      Article first published online: 23 JUL 2010 | DOI: 10.1002/chem.201001471

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      Accessing CeIV: The tetravalent oxidation state of cerium is unusual and often associated with multiconfigurational behaviour. Analysis of the bonding in tetravalent, rather than more conventional trivalent, f-block complexes shows the 5f metal bonds to softer ligands are stronger and more covalent than 4f analogues (see scheme). The use of trityl chloride as a simple oxidant to access CeIV is also shown.

    18. Molecular Modeling

      Multistep Virtual Screening for Rapid and Efficient Identification of Non-Nucleoside Bacterial Thymidine Kinase Inhibitors (pages 9630–9637)

      Johannes Zander, Markus Hartenfeller, Volker Hähnke, Ewgenij Proschak, Silke Besier, Thomas A. Wichelhaus and Gisbert Schneider

      Article first published online: 20 JUL 2010 | DOI: 10.1002/chem.201001347

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      Resistance is futile! Computer-assisted protein modeling and parallel virtual screening led to the identification of antibiotic agents that combat clinically relevant drug-resistant Staphylococcus aureus. The non-nucleoside inhibitors target bacterial thymidine kinase (see figure).

    19. Heptamethine Cyanines

      Efficient Utilization of Higher-Lying Excited States to Trigger Charge-Transfer Events (pages 9638–9645)

      Pierre-Antoine Bouit, Fabian Spänig, Gregory Kuzmanich, Evangelos Krokos, Christian Oelsner, Miguel A. Garcia-Garibay, Juan Luis Delgado, Nazario Martín and Dirk M. Guldi

      Article first published online: 26 JUL 2010 | DOI: 10.1002/chem.201001613

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      The higher the better: We have realized the rarely found scenario of a charge transfer that commences in a higher-energy excited state (see image), through the careful choice of electron donor and electron acceptor.

    20. Green Phosphors

      Material Properties and Structural Characterization of M3Si6O12N2:Eu2+ (M=Ba, Sr)—A Comprehensive Study on a Promising Green Phosphor for pc-LEDs (pages 9646–9657)

      Cordula Braun, Markus Seibald, Saskia L. Börger, Oliver Oeckler, Teak D. Boyko, Alexander Moewes, Gerhard Miehe, Andreas Tücks and Wolfgang Schnick

      Article first published online: 28 JUL 2010 | DOI: 10.1002/chem.201000660

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      Give it the green light! The luminescence properties of M3Si6O12N2:Eu2+ (M=Ba,Sr) render this layered Ba–oxonitridosilicate an interesting phosphor for pc-LEDs. Various improved syntheses lead to highly crystalline products as well as single crystals suitable for precise structure determination (see figure). In situ high-pressure and high-temperature investigations indicate the best sintering conditions. XES and XAS spectra were conducted for a better understanding of the electronic structure.

    21. Catalysis

      Asymmetric C[BOND]C Bond-Formation Reaction with Pd: How to Favor Heterogeneous or Homogeneous Catalysis? (pages 9658–9668)

      Sven Reimann, Jan-Dierk Grunwaldt, Tamas Mallat and Alfons Baiker

      Article first published online: 21 JUL 2010 | DOI: 10.1002/chem.201000833

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      Homogeneous or heterogeneous? A combined approach by using catalytic experiments and in situ XANES spectroscopy was used to clarify the heterogeneous or homogeneous nature of the Pd/Al2O3[BOND](R)-BINAP catalyst system (see graphic) applied in the enantioselective allylic alkylation of (E)-1,3-diphenylallyl acetate. Crucial factors that cause leaching were identified.

    22. O[BOND]O Activation

      Dioxygenase-Like Reactivity of an Isolable Superoxo–Nickel(II) Complex (pages 9669–9675)

      Anna Company, Shenglai Yao, Kallol Ray and Matthias Driess

      Article first published online: 19 JUL 2010 | DOI: 10.1002/chem.201001138

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      Superoxo magic: The oxidizing ability of an isolable and thermally stable superoxo–nickel(II) towards exogenous organic substrates has been studied for the first time in detail (see scheme). The complex is suitable to oxidize O[BOND]H and N[BOND]H bonds and even shows a unique dioxygenase-like reactivity towards phenols to give unexpected oxidation products.

    23. Direct C[BOND]H Functionalisation

      PdII-Catalysed C[BOND]H Functionalisation of Indoles and Pyrroles Assisted by the Removable N-(2-Pyridyl)sulfonyl Group: C2-Alkenylation and Dehydrogenative Homocoupling (pages 9676–9685)

      Alfonso García-Rubia, Beatriz Urones, Ramón Gómez Arrayás and Juan Carlos Carretero

      Article first published online: 22 JUL 2010 | DOI: 10.1002/chem.201001126

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      Temporary control: The easily installed and removed N-(2-pyridyl)sulfonyl group directs the C[BOND]H functionalisation of indoles with complete regiocontrol for C2 and allows the final N deprotection by facile, reductive N[BOND]S cleavage (see scheme). This concept has been successfully applied to the C2[BOND]H alkenylation of indoles and pyrroles as well as to the dehydrogenative intermolecular homocoupling of indoles to afford 2,2′-biindoles.

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      Preview: Chem. Eur. J. 32/2010 (page 9691)

      Article first published online: 12 AUG 2010 | DOI: 10.1002/chem.201090156

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