Chemistry - A European Journal

Cover image for Vol. 17 Issue 47

November 18, 2011

Volume 17, Issue 47

Pages 13105–13367

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Concept
    8. Communications
    9. Full Papers
    10. Preview
    1. Cover Picture: Is Electronegativity a Useful Descriptor for the Pseudo-Alkali Metal NH4? (Chem. Eur. J. 47/2011) (page 13105)

      Alexander Whiteside, Dr. Sotiris S. Xantheas and Prof. Maciej Gutowski

      Article first published online: 14 NOV 2011 | DOI: 10.1002/chem.201190241

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      The computational electronegativity of the ammonium radical reveals the differences between atoms and “pseudo-atoms” in a paper from A. Whiteside, S. S. Xantheas, and M. Gutowski on page 13197 ff. It is shown from simulations and experimental data that NH4 can behave like an alkali metal if its molecular properties are suppressed. Activating these properties, such as geometric flexibility, exposes their influence upon the pseudo-atom's behaviour. Four of the leading historical figures in this area of chemistry are depicted: clockwise from top left: J. J. Berzelius, R. S. Mulliken, G. Herzberg, and L. C. Pauling. Portrait credits: Berzelius from Wikimedia Commons, Mulliken and Pauling from G. Hund, Herzberg from University of Saskatchewan Archives (A-3234).

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Concept
    8. Communications
    9. Full Papers
    10. Preview
    1. Inside Cover: Interfacial Complexation Reactions of Sr2+ with Octyl(phenyl)-N,N-diisobutylcarbamoylmethylphosphine Oxide for Understanding Its Extraction in Reprocessing Spent Nuclear Fuels (Chem. Eur. J. 47/2011) (page 13106)

      Tom J. Stockmann, Yu Lu, Jing Zhang, Prof. Hubert H. Girault and Prof. Zhifeng Ding

      Article first published online: 14 NOV 2011 | DOI: 10.1002/chem.201190242

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      Stoichiometry and complexation equilibrium constants for the extraction of strontium from spent nuclear fuels at water|room-temperature ionic liquid (RTIL) interfaces are very important for medicinal use of radioisotopes and remediation of contaminated environments. In their Full Paper on page 13206 ff., Z. Ding et al. demonstrate their investigations on the working model by means of biphasic and normal electrospray ionization mass spectroscopy and electrochemistry at water|1,2-dichloroethane and water|RTIL micro-interfaces.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Concept
    8. Communications
    9. Full Papers
    10. Preview
    1. Graphical Abstract: Chem. Eur. J. 47/2011 (pages 13109–13118)

      Article first published online: 14 NOV 2011 | DOI: 10.1002/chem.201190243

  4. Corrigenda

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Concept
    8. Communications
    9. Full Papers
    10. Preview
    1. You have free access to this content
      Corrigendum: An Atomic-Level Strategy for Unraveling Gold Nanocatalysis from the Perspective of Aun(SR)m Nanoclusters (page 13117)

      Dr. Yan Zhu, Huifeng Qian and Prof. Rongchao Jin

      Article first published online: 14 NOV 2011 | DOI: 10.1002/chem.201103116

      This article corrects:

      An Atomic-Level Strategy for Unraveling Gold Nanocatalysis from the Perspective of Aun(SR)m Nanoclusters

      Vol. 16, Issue 37, 11455–11462, Article first published online: 16 AUG 2010

    2. You have free access to this content
      Corrigendum: Dispersing Carbon Nanotubes with Graphene Oxide in Water and Synergistic Effects between Graphene Derivatives (page 13117)

      Ling Qiu, Xiaowei Yang, Dr. Xinglong Gou, Dr. Wenrong Yang, Prof. Zi-Feng Ma, Prof. Gordon G. Wallace and Dr. Dan Li

      Article first published online: 14 NOV 2011 | DOI: 10.1002/chem.201103117

      This article corrects:

      Dispersing Carbon Nanotubes with Graphene Oxide in Water and Synergistic Effects between Graphene Derivatives

      Vol. 16, Issue 35, 10653–10658, Article first published online: 2 AUG 2010

    3. You have free access to this content
      Corrigendum: Synthesis of Diverse Indole-Containing Scaffolds by Gold(I)-Catalyzed Tandem Reactions of 3-Propargylindoles Initiated by 1,2-Indole Migrations: Scope and Computational Studies (page 13117)

      Roberto Sanz, Delia Miguel, Mukut Gohain, Patricia García-García, Manuel A. Fernández-Rodríguez, Adán González-Pérez, Olalla Nieto-Faza, Ángel R. de Lera and Félix Rodríguez

      Article first published online: 14 NOV 2011 | DOI: 10.1002/chem.201103118

    4. You have free access to this content
      Corrigendum: Sonication-Triggered Instantaneous Gel-to-Gel Transformation (page 13117)

      Xudong Yu, Qian Liu, Junchen Wu, Mingming Zhang, Xinhua Cao, Song Zhang, Qi Wang, Liming Chen and Tao Yi

      Article first published online: 14 NOV 2011 | DOI: 10.1002/chem.201103119

      This article corrects:

      Sonication-Triggered Instantaneous Gel-to-Gel Transformation

      Vol. 16, Issue 30, 9099–9106, Article first published online: 22 JUN 2010

    5. You have free access to this content
      Corrigendum: High-Density DNA Functionalization by a Combination of Cu-Catalyzed and Cu-Free Click Chemistry (page 13118)

      Katrin Gutsmiedl, Danila Fazio and Thomas Carell

      Article first published online: 14 NOV 2011 | DOI: 10.1002/chem.201103120

      This article corrects:

      High-Density DNA Functionalization by a Combination of Cu-Catalyzed and Cu-Free Click Chemistry

      Vol. 16, Issue 23, 6877–6883, Article first published online: 10 MAY 2010

    6. You have free access to this content
    7. You have free access to this content
      Corrigendum: Photochemistry in Photonic Crystal Fiber Nanoreactors (page 13118)

      Jocelyn S. Y. Chen, Tijmen G. Euser, Nicola J. Farrer, Peter J. Sadler, Michael Scharrer and Philip St. J.  Russell

      Article first published online: 14 NOV 2011 | DOI: 10.1002/chem.201103122

      This article corrects:

      Photochemistry in Photonic Crystal Fiber Nanoreactors

      Vol. 16, Issue 19, 5607–5612, Article first published online: 12 APR 2010

    8. You have free access to this content
      Corrigendum: Catalytic Asymmetric 1,3-Dipolar Cycloaddition of α-Iminonitriles (page 13118)

      Rocío Robles-Machín, Inés Alonso, Javier Adrio and Juan C. Carretero

      Article first published online: 14 NOV 2011 | DOI: 10.1002/chem.201103123

      This article corrects:

      Catalytic Asymmetric 1,3-Dipolar Cycloaddition of α-Iminonitriles

      Vol. 16, Issue 18, 5286–5291, Article first published online: 31 MAR 2010

  5. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Concept
    8. Communications
    9. Full Papers
    10. Preview
  6. Concept

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Concept
    8. Communications
    9. Full Papers
    10. Preview
    1. Tertiary Boronic Esters

      Highly Enantioselective Synthesis of Tertiary Boronic Esters and their Stereospecific Conversion to other Functional Groups and Quaternary Stereocentres (pages 13124–13132)

      Helen K. Scott and Prof.  Varinder K. Aggarwal

      Article first published online: 3 NOV 2011 | DOI: 10.1002/chem.201102581

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      The boron supremacy: A highly enantioselective synthesis of tertiary boronic esters has been developed from the corresponding secondary alcohols. The tertiary boronic esters have been further transformed with high selectivity into a range of functional groups, including tertiary alcohols, C-tertiary amines, quaternary stereocentres and tertiary arylalkanes (see scheme).

  7. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Concept
    8. Communications
    9. Full Papers
    10. Preview
    1. Annulation

      General Au-Catalyzed Benzannulation Towards Naturally Occurring Carbazole Alkaloids from Methoxypropadiene (pages 13134–13137)

      Wangqing Kong, Chunling Fu and Prof. Dr. Shengming Ma

      Article first published online: 11 OCT 2011 | DOI: 10.1002/chem.201102251

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      Accessible alkaloids: Naturally occurring carbazole alkaloids, such as clauszoline-K, -L, -M, and -N, 3-formyl-7-hydroxycarbazole, and siamenol, were synthesized through a gold-catalyzed cyclization reaction of 1-(indol-2-yl)-2-methoxy-2,3-allenols, which are readily available from indolecarbaldehydes and methoxypropadiene (see scheme; R1=Me, carboxylic acid/ester, or aldehyde; R2=prenyl or H; R3=H or Me). The reaction demonstrates atom economy, high selectivity, and high yields, mostly with catalytic reactions.

    2. Chirality

      Double Chirality Transmission in Trityl Amines: Sensing Molecular Dynamic Stereochemistry by Circular Dichroism and DFT Calculations (pages 13138–13141)

      Jacek Ściebura and Prof. Dr. Jacek Gawroński

      Article first published online: 18 OCT 2011 | DOI: 10.1002/chem.201101699

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      Con-figured out: The tert-butyl group can be formally seen as “less” sterically demanding (M) than the methyl group (L). This is the case when a CD-active trityl group at the nitrogen atom is used to report the chirality of the carbon substituent with two different sized groups (see scheme). The use of the trityl CD sensor allowed, in addition, the determination of the dominant absolute configuration of the nitrogen atom in chiral amines.

    3. Nanotechnology

      Glucose-Assisted Growth of MoS2 Nanosheets on CNT Backbone for Improved Lithium Storage Properties (pages 13142–13145)

      Dr. Shujiang Ding, Jun Song Chen and Prof. Xiong Wen (David) Lou

      Article first published online: 18 OCT 2011 | DOI: 10.1002/chem.201102480

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      Pour a little sugar on it: A simple glucose-assisted hydrothermal method to directly grow MoS2 nanosheets (NSs) on the CNT backbone is reported (see picture). Several features of these CNT@MoS2 structures, including high MoS2 content in the hybrid structure, large surface area provided by the nanosheet structure, and a conducting network of amorphous carbon and CNT backbone, lead to significantly improved lithium storage properties.

    4. Flow Chemistry

      A Two-Step Continuous-Flow Synthesis of N-(2-Aminoethyl)acylamides through Ring-Opening/Hydrogenation of Oxazolines (pages 13146–13150)

      Bernhard Gutmann, Dr. Jean-Paul Roduit, Dr. Dominique Roberge and Prof. Dr.  C. Oliver Kappe

      Article first published online: 14 OCT 2011 | DOI: 10.1002/chem.201102772

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      Harnessing hydrazoic acid in flow! 2-Oxazolines can be ring-opened in a very efficient manner by treatment with in situ generated hydrazoic acid. Despite the toxic and explosive nature of hydrazoic acid, this process can be conducted safely in a continuous-flow format with residence times as short as 5 min at 130 °C (see scheme).

    5. Carbenes

      An Ambidentate Janus-Type Ligand System Based on Fused Carbene and Imidato Functionalities (pages 13151–13155)

      Dr. Nadia Vujkovic, Dr. Vincent César, Dr. Noël Lugan and Dr. Guy Lavigne

      Article first published online: 13 OCT 2011 | DOI: 10.1002/chem.201102767

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      The new anionic heterocycleimidNHC (4,6-dioxo-1,3,5-triazin-2-ylidene-5-ide), combining a carbene and an anionic imidate, was readily prepared through a coupling reaction between 1,3-dimesityl formamidine and N-phenoxy carbonyl isocyanate followed by deprotonation. The donor properties of this switchable ligand were determined, whereas its ambidentate nature was established through the directed construction of exotic stacked polymetallic architectures.

    6. Synthetic Methods

      Skeletal Alkylcarbonation (SAC) Reactions as a Simple Design for Cluster–Carbon Insertion and Cross-Coupling: High-Yield Access to Substituted Tricarbollides from 6,9-Dicarba-arachno-decaborane(14) (pages 13156–13159)

      Prof. Dr. Bohumil Štíbr, Dr. Mario Bakardjiev, Dr. Josef Holub, Prof. Dr. Aleš Růžička, Dr. Zdeňka Padělková, Roman Olejník and Dr. Petr Švec

      Article first published online: 18 OCT 2011 | DOI: 10.1002/chem.201102016

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      A simple and high-yield route to a series of tricarbollide compounds 8-R-nido-7,8,9-C3B8H11 and [8-R-nido-7,8,9-C3B8H10] (exemplified by R=Me, Ph, and 1-naphthyl) was developed. The method is based on a new type of C-insertion cross-coupling through skeletal alkylcarbonation (SAC) reactions between acyl chlorides (RCOCl) and the arachno-6,9-C2B8H14 carborane (see scheme).

    7. Domino Reactions

      Yb(OTf)3- or AuI-Catalyzed Domino Intramolecular Hydroamination and Ring-Opening of Sulfonamide-Substituted 1,1-Vinylidenecyclopropanediesters (pages 13160–13165)

      Lei Wu and Prof. Min Shi

      Article first published online: 18 OCT 2011 | DOI: 10.1002/chem.201102159

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      Hard or soft determines the outcome: Five-membered N,O-heterocyclic compounds containing an alkyne moiety or a carbonyl group were efficiently synthesized from sulfonamide-substituted vinylidenecyclopropanediesters, catalyzed by a hard Lewis acid Yb(OTf)3 and a soft Lewis acid AuI complex, respectively (see scheme). The products were obtained in moderate to excellent yields under mild conditions and the reaction mechanisms were discussed on the basis of control and 18O-labeling experiments.

    8. Molecular Electronics

      Molecular Junctions Bridged by Metal Ion Complexes (pages 13166–13169)

      Dong Xiang, Feliks Pyatkov, Florian Schröper, Prof. Andreas Offenhäusser, Prof. Yi Zhang and Dr. Dirk Mayer

      Article first published online: 14 OCT 2011 | DOI: 10.1002/chem.201102915

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      A bridged version: Molecular junctions bridged by metal ion complexes were investigated by mechanically controllable break junction experiments on the level of individual molecules. The electrical conductance of the junctions varied strongly with the kind of bonded metal ion, in the order: Ca2+≫Zn2+>Ni2+ (see figure).

    9. Drug Delivery

      Selective Recognition of Co-assembled Thrombin Aptamer and Docetaxel on Mesoporous Silica Nanoparticles against Tumor Cell Proliferation (pages 13170–13174)

      Liang Gao, Dr. Yue Cui, Prof. Dr. Qiang He, Dr. Yang Yang, Dr. Jinbo Fei and Prof. Dr. Junbai Li

      Article first published online: 19 OCT 2011 | DOI: 10.1002/chem.201101658

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      Delivery plan: Thrombin binding aptamer tethered to lipid-coated mesoporous silica nanoparticles (TBA A15–lipid–MSN, above arrow) were rationally designed to deliver docetaxel for combined tumor cell suppression. The dual function of the bioconjugates in the extracellular matrix and cytoplasm of HeLa cells was demonstrated. This hybrid system could be extended for combined anticancer treatment when PAR-1 is over-expressed.

    10. Photochemistry

      A Family of Visible-Light Responsive Photocatalysts Obtained by Dispersing CrO6 Octahedra into a Hydrotalcite Matrix (pages 13175–13181)

      Yufei Zhao, Shitong Zhang, Bei Li, Dr. Hong Yan, Shan He, Lei Tian, Wenying Shi, Prof. Jing Ma, Prof. Min Wei, Prof. David G. Evans and Prof. Xue Duan

      Article first published online: 11 OCT 2011 | DOI: 10.1002/chem.201101874

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      Visibly clear: A family of visible-light-responsive MCr–layered double hydroxides (LDHs; M=Cu, Ni, Zn) were synthesized. These show remarkable photocatalytic activity with visible-light irradiation. Experimental and computational studies revealed that the visible-light response of MCr[BOND]NO3–LDHs originates from a d–d transition in the orderly dispersed CrO6 octahedra in the hydrotalcite layer.

    11. Nanocomposites

      Smectic-Layer Alignments of Surface-Modified Gold Nanoparticles in the Nanocomposite Induced by a Hydrogen-Bonded Bent-Core Liquid Crystalline Host under Electric Fields (pages 13182–13187)

      Wei-Hong Chen, Yi-Ting Chang, Jey-Jau Lee, Wei-Tsung Chuang and Prof. Hong-Cheu Lin

      Article first published online: 18 OCT 2011 | DOI: 10.1002/chem.201102607

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      Packing tips: The layer spacing of 5.5 nm (see TEM image) of the nanocomposite VPy-SiA/AuNPs-S (5 wt %) under DC/AC electric fields perfectly matches the d spacing of 5.5 nm obtained by in situ XRD measurements under a DC electric field. TEM images revealed that the well-organized packing of layers of surface-modified gold NPs could be induced in the nanocomposite under electric fields.

  8. Full Papers

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Concept
    8. Communications
    9. Full Papers
    10. Preview
    1. Dendrimers

      Dendritic, Nanosized Building Block for Siloxane-Based Materials: A Spherosilicate Dendrimer (pages 13188–13196)

      Kazufumi Kawahara, Dr. Yoshiaki Hagiwara and Prof. Kazuyuki Kuroda

      Article first published online: 28 OCT 2011 | DOI: 10.1002/chem.201102205

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      Small but perfectly formed: A well-defined spherosilicate dendrimer (DMS-1, see scheme), consisting of 40 Si atoms with 24 Si[BOND]H groups on the surface, was synthesized by stepwise silylation of double-four-ring (D4R) silicate. The dendrimer can be regarded as the smallest precisely controlled silica nanoparticle, about 1.5 nm in size. It is a versatile scaffold for siloxane-based materials due to the presence of the reactive Si[BOND]H groups.

    2. Electronegativity

      Is Electronegativity a Useful Descriptor for the Pseudo-Alkali Metal NH4? (pages 13197–13205)

      Alexander Whiteside, Dr. Sotiris S. Xantheas and Prof. Maciej Gutowski

      Article first published online: 19 SEP 2011 | DOI: 10.1002/chem.201101949

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      Molecules as atoms: Can some molecular ions be described as “pseudo-atoms” with well-defined electronegativities? A suitable definition for electronegativity exists, but molecules have abilities that atoms lack. In this paper, a discussion on how well the electronegativity of ammonium describes its behaviour, and how its molecular nature complicates this picture (see figure) is presented.

    3. Facilitated Ion Transfer

      Interfacial Complexation Reactions of Sr2+ with Octyl(phenyl)-N,N-diisobutylcarbamoylmethylphosphine Oxide for Understanding Its Extraction in Reprocessing Spent Nuclear Fuels (pages 13206–13216)

      Tom J. Stockmann, Yu Lu, Jing Zhang, Prof. Hubert H. Girault and Prof. Zhifeng Ding

      Article first published online: 24 OCT 2011 | DOI: 10.1002/chem.201102491

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      The extraction of strontium at a liquid|liquid microinterface, housed at the tip of a pulled capillary is described using “classical” octyl(phenyl)-N,N-diisobutylcarbamoylmethylphosphine oxide as a ligand. This system has wide applications as a sensor technology; in the recovery of fissile material and radioisotopes for medicinal use from nuclear waste; or in environmental recovery/reclamation projects. The thermodynamics of simple and facilitated ion transfer at the aqueous| ionic liquid interface are discussed.

    4. Carboranes

      Design of Dinuclear Copper Species with Carboranylcarboxylate Ligands: Study of Their Steric and Electronic Effects (pages 13217–13229)

      Mònica Fontanet, Adrian-Radu Popescu, Xavier Fontrodona, Dr. Montserrat Rodríguez, Dr. Isabel Romero, Prof. Francesc Teixidor, Prof. Clara Viñas, Dr. Núria Aliaga-Alcalde and Dr. Eliseo Ruiz

      Article first published online: 18 OCT 2011 | DOI: 10.1002/chem.201101929

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      Reinventing the wheel: A family of new carboranylcarboxylate-bridged dinuclear CuII compounds with paddle-wheel structure (see figure) have been synthesized and characterized by spectroscopic and magnetic techniques. Computational studies were used to study their magnetic properties and their stability on the basis of the strength of the bond between each CuII and the terminal ligand.

    5. Biaryl Synthesis

      Aryl–Aryl Bond Formation by the Fluoride-Free Cross-Coupling of Aryldisiloxanes with Aryl Bromides (pages 13230–13239)

      Dr. Christine M. Boehner, Elizabeth C. Frye, Kieron M. G. O'Connell, Dr. Warren R. J. D. Galloway, Dr. Hannah F. Sore, Dr. Patricia Garcia Dominguez, Dr. David Norton, Dr. David G. Hulcoop, Dr. Martin Owen, Dr. Gillian Turner, Dr. Claire Crawford, Dr. Helen Horsley and Dr. David R. Spring

      Article first published online: 11 OCT 2011 | DOI: 10.1002/chem.201102285

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      An attractive alternative: Biaryl synthesis, involving the fluoride-free cross-coupling of aryl bromides with aryldisiloxanes, is reported. This methodology is an attractive alternative to the traditional transition-metal-catalysed routes typically used to generate molecules containing the privileged biaryl scaffold (see scheme). As such, it is anticipated that this cross-coupling strategy could prove valuable in a wide synthetic context.

    6. Organocatalysis

      Organocatalytic Strategies for the Construction of Optically Active Imidazoles, Oxazoles, and Thiazoles (pages 13240–13246)

      Dr. Łukasz Albrecht, Lars Krogager Ransborg, Dr. Anna Albrecht, Lennart Lykke and Prof. Dr. Karl Anker Jørgensen

      Article first published online: 20 OCT 2011 | DOI: 10.1002/chem.201101817

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      Asymmetric organocatalytic one-pot strategies for the construction of biologically relevant hydroxyalkyl- or aminoalkyl-substituted 1,3-azoles are described (see scheme). These multi-bond-forming organocatalytic reaction cascades proceed with high efficiency and the target heterocycles are formed in a highly enantioselective manner under mild reaction conditions.

    7. Energy Transfer

      Oligo(p-phenylene ethynylene)–BODIPY Derivatives: Synthesis, Energy Transfer, and Quantum-Chemical Calculations (pages 13247–13257)

      Dr. Shouchun Yin , Dr. Volker Leen, Carine Jackers , Prof. David Beljonne, Dr. Bernard Van Averbeke, Prof. Mark Van der Auweraer , Prof. Noël Boens and Prof. Wim Dehaen

      Article first published online: 11 OCT 2011 | DOI: 10.1002/chem.201100454

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      Acceptor–donor–acceptor systems in which oligo(p-phenylene ethynylene)s with different conjugated chain lengths (OPEn, where n is the number of phenyl acetylene units) as the energy-donor subunit are capped at both ends with BODIPY chromophores as the energy-acceptor subunits (OPEBn) were synthesized. Energy transfer from OPEn to BODIPY in OPEBn is very efficient and the energy-transfer efficiency decreases somewhat with increasing n (see picture).

    8. Dyes/Pigments

      Click Assembly of Dye-Functionalized Octasilsesquioxanes for Highly Efficient and Photostable Photonic Systems (pages 13258–13268)

      M. Eugenia Pérez-Ojeda, Beatriz Trastoy, Prof. Dr. Íñigo López-Arbeloa, Dr. Jorge Bañuelos, Prof. Dr. Ángel Costela, Prof. Dr. Inmaculada García-Moreno and Dr. Jose Luis Chiara

      Article first published online: 20 OCT 2011 | DOI: 10.1002/chem.201100512

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      Hybrid dyes: Fluorescently labeled mono- or octa-substituted octasilsesquioxanes can be efficiently obtained from the corresponding octa-azido silsesquioxane by click chemistry (see scheme). Attachment to the inorganic core significantly improves the laser performance of the dye in both the liquid phase and solid matrices.

    9. Heterogeneous Catalysis

      Small Pd Nanoparticles Supported in Large Pores of Mesocellular Foam: An Excellent Catalyst for Racemization of Amines (pages 13269–13273)

      Dr. Mozaffar Shakeri, Dr. Cheuk-wai Tai, Dr. Emmanuelle Göthelid, Prof. Sven Oscarsson and Prof. Jan-E. Bäckvall

      Article first published online: 20 OCT 2011 | DOI: 10.1002/chem.201101265

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      Crystals in foams: A Pd-nanocatalyst (1–2 nm) was synthesized in large-pore-size mesocellular foam (MCF) and has been characterized by TEM, powder XRD and XPS. The Pd-nanocatalyst/MCF showed an excellent activity and selectivity toward racemization of (S)-1-phenylethylamine (see figure). The activity of the Pd-nanocatalyst/MCF increased over time with use despite an increase in Pd nanoparticle size.

    10. G-Quadruplexes

      Tridentate N-Donor Palladium(II) Complexes as Efficient Coordinating Quadruplex DNA Binders (pages 13274–13283)

      Eric Largy, Dr. Florian Hamon, Dr. Frédéric Rosu, Dr. Valérie Gabelica, Prof. Edwin De Pauw, Aurore Guédin, Dr. Jean-Louis Mergny and Dr. Marie-Paule Teulade-Fichou

      Article first published online: 18 OCT 2011 | DOI: 10.1002/chem.201102300

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      Package deal: Complexes of Pd2+, Pt2+, and Cu2+ were prepared to test their G-quadruplex DNA (G4 DNA) binding properties (see figure). A striking positive effect of palladium on the G4 DNA stabilization was observed. Palladium complexes efficiently coordinated G4 DNA at room temperature on a minute scale.

    11. Deprotocupration

      Deprotonative Metalation of Chloro- and Bromopyridines Using Amido-Based Bimetallic Species and Regioselectivity-Computed CH Acidity Relationships (pages 13284–13297)

      Dr. Katia Snégaroff, Tan Tai Nguyen, Nada Marquise, Dr. Yury S. Halauko, Philip J. Harford, Dr. Thierry Roisnel, Dr. Vadim E. Matulis, Prof. Oleg A. Ivashkevich, Dr. Floris Chevallier, Dr. Andrew E. H. Wheatley, Dr. Philippe C. Gros and Prof. Florence Mongin

      Article first published online: 18 OCT 2011 | DOI: 10.1002/chem.201101993

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      Getting your Li's mixed up: Various chloro- and bromopyridines have been functionalized after deprotometalation using 2,2,6,6-tetramethylpiperidino (TMP)-based mixed lithium–zinc, lithium–cadmium, and lithium–copper combinations (see scheme). The outcome has been discussed in light of the CH acidities of the substrates, determined both in the gas phase and as a solution in THF by using the DFT B3LYP method.

    12. Carboranylamidinate Complexes

      Versatile Reactivity of Half-Sandwich Ir and Rh Complexes toward Carboranylamidinates and Their Derivatives: Synthesis, Structure, and Catalytic Activity for Norbornene Polymerization (pages 13298–13307)

      Dr. Zi-Jian Yao, Ge Su and Prof. Dr. Guo-Xin Jin

      Article first published online: 18 OCT 2011 | DOI: 10.1002/chem.201101638

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      A selection of sandwiches: Three kinds of half-sandwich Ir and Rh complexes based on carboranylamidinate ligands have been synthesized and characterized (see scheme; Cp*=η5-C5Me5). The catalytic activity of one of the Ir complexes in norbornene polymerization was investigated.

    13. Metal Catalysis

      Pt–Sn/γ-Al2O3-Catalyzed Highly Efficient Direct Synthesis of Secondary and Tertiary Amines and Imines (pages 13308–13317)

      Wei He, Liandi Wang, Prof. Chenglin Sun, Kaikai Wu, Dr. Songbo He, Prof. Dr. Jiping Chen, Ping Wu and Prof. Dr. Zhengkun Yu 

      Article first published online: 13 OCT 2011 | DOI: 10.1002/chem.201101725

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      Bimetallic cat tricks: Efficient Pt–Sn/γ-Al2O3-catalyzed synthesis of secondary and tertiary amines by direct N-alkylation of primary and secondary amines, respectively, with alcohols or by deaminative self-coupling of amines has been realized (see scheme). Under an oxygen atmosphere, imines were also efficiently prepared by the same reactions.

    14. Carbonylation

      Carbonylation of Nitrobenzene in Methanol with Palladium Bidentate Phosphane Complexes: An Unexpectedly Complex Network of Catalytic Reactions, Centred around a Pd–imido Intermediate (pages 13318–13333)

      Tiddo J. Mooibroek, Lodi Schoon, Prof. Dr. Elisabeth Bouwman and Prof. Dr. Eite Drent

      Article first published online: 18 OCT 2011 | DOI: 10.1002/chem.201100923

      Thumbnail image of graphical abstract

      Pd-catalyzed carbonylation of PhNO2 with CO in CH3OH has been studied. PhNO2 is reduced by CO and, surprisingly, also by CH3OH as (co-)reductant, leading to a proposed Pd[DOUBLE BOND]NPh complex. This Pd–imido compound is thought to be the key intermediate in a complex network of catalytic reactions, linking together the formation of all observed CH3OH oxidation products and PhNO2 reduction products (see scheme).

    15. Natural Products

      Total Synthesis of Pamamycin-649B (pages 13334–13340)

      Dr. Petra Fischer, Dr. Margit Gruner, Anne Jäger, Dr. Olga Kataeva and Prof. Dr. Peter Metz

      Article first published online: 20 OCT 2011 | DOI: 10.1002/chem.201102093

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      Sultones in action: The first total synthesis of the title macrodiolide antibiotic was achieved by using sultone methodology. Since the final lactonization with formation of the ester linkage between C1′ and the C8 oxygen proceeded with complete C2′ epimerization, the more readily available C2′ epimeric smaller fragment could be used to streamline the synthetic sequence.

    16. Biotransformations

      Studies on the Biodegradation of Fosfomycin: Synthesis of 13C-Labeled Intermediates, Feeding Experiments with Rhizobium huakuii PMY1, and Isolation of Labeled Amino Acids from Cell Mass by HPLC (pages 13341–13348)

      Dr. John W. McGrath, Prof. Dr. Friedrich Hammerschmidt, Prof. Dr. Hanspeter Kählig, Dr. Frank Wuggenig, Prof. Dr. Günther Lamprecht and Dr. John P. Quinn

      Article first published online: 20 OCT 2011 | DOI: 10.1002/chem.201100725

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      Biodegradation of fosfomycin: Racemic (1R*,2R*)-1,2-dihydroxypropylphosphonic acid and hydroxyacetone, both 13C-labeled at C-1, are degraded by R. huakuii PMY1 and incorporated into cell mass. Alanine and valine were found to be labeled in their carboxyl groups (see scheme). Therefore, hydroxyacetone is on the biodegradation pathway of fosfomycin in R. huakuii PMY1.

    17. Natural Products

      Synthesis of Chondramide A Analogues with Modified β-Tyrosine and Their Biological Evaluation (pages 13349–13357)

      Dipl.-Chem. Alexander Zhdanko, Dr. Anke Schmauder, Dr. Christopher I. Ma, Prof. Dr. L. David Sibley, Prof. Dr. David Sept, Dr. Florenz Sasse and Prof. Dr. Martin E. Maier

      Article first published online: 20 OCT 2011 | DOI: 10.1002/chem.201101978

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      SUB-units: Ten different chondramide A analogues were prepared with different substituents at the 3-amino-2-methoxy-propanoate subunit. The modified β-tyrosines were obtained from the corresponding cinnamates. From Mitsunobu esterification, acyclic depsipeptides were obtained that were cyclized by macrolactam formation. Almost all analogues were at least as active as chondramide A itself. However, an amide group reduced the cytotoxicity significantly.

    18. Bioinorganic Chemistry

      Transformation of the {Fe(NO)2}9 Dinitrosyl Iron Complexes (DNICs) into S-Nitrosothiols (RSNOs) Triggered by Acid–Base Pairs (pages 13358–13366)

      Chih-Chin Tsou and Prof. Dr. Wen-Feng Liaw

      Article first published online: 18 OCT 2011 | DOI: 10.1002/chem.201100253

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      Trigger happy: Transformation of {Fe(NO)2}9 dinitrosyl iron complexes (or Roussin's red esters) into S-nitrosothiols (RSNOs) along with {Fe(NO)}7 mononitrosyl iron complex [(NO)Fe(S2CNMe2)2] facilitated by (S2CNMe2)2 and Brønsted acid (see scheme) demonstrates that Brønsted acids may play a critical role in triggering S-nitrosation.

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      Preview: Chem. Eur. J. 48/2011 (page 13367)

      Article first published online: 14 NOV 2011 | DOI: 10.1002/chem.201190245

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