Chemistry - A European Journal

Cover image for Vol. 16 Issue 12

March 22, 2010

Volume 16, Issue 12

Pages 3551–3865

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Communications
    8. Full Papers
    9. Preview
    1. Cover Picture: Selective Ruthenium-Catalyzed N-Alkylation of Indoles by Using Alcohols (Chem. Eur. J. 12/2010) (page 3551)

      Sebastian Bähn, Sebastian Imm, Kathleen Mevius, Lorenz Neubert, Annegret Tillack, Jonathan M. J. Williams and Matthias Beller

      Version of Record online: 16 MAR 2010 | DOI: 10.1002/chem.201090052

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      Borrowing hydrogen catalysis for an environmentally benign N-alkylation of indoles with alcohols is described in a joint effort by M. Beller, J. Williams, and co-workers in their Communication on page 3590 ff. This novel procedure occurs through an unusual “borrowing hydrogen” methodology by use of the Shvo catalyst. The protocol is operationally simple and mechanistically involves an in situ transfer hydrogenation of the indole.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Communications
    8. Full Papers
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    1. Inside Cover: Construction of SnIV Porphyrin/Trinuclear Ruthenium Cluster Dyads Linked by Pyridine Carboxylates: Photoinduced Electron Transfer in the Marcus Inverted Region (Chem. Eur. J. 12/2010) (page 3552)

      Takahiko Kojima, Kakeru Hanabusa, Kei Ohkubo, Motoo Shiro and Shunichi Fukuzumi

      Version of Record online: 16 MAR 2010 | DOI: 10.1002/chem.201090053

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      A series of conglomerates consisting of trinulcear RuIII clusters as electron acceptors and saddle-distorted SnIV–dodecaphenylporphyrin complexes as electron donors was synthesized. Photoinduced electron transfer was observed in which both forward and backward transfer occurred in the Marcus inverted region, to afford electron-transfer states of the conglomerates. For more details see the Full Paper by T. Kojima, S. Fukuzumi et al. on page 3646 ff.

  3. Graphical Abstract

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

    1. Top of page
    2. Cover Picture
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    4. Graphical Abstract
    5. News
    6. Review
    7. Communications
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  5. Review

    1. Top of page
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    4. Graphical Abstract
    5. News
    6. Review
    7. Communications
    8. Full Papers
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    1. Hydrophobic Effect

      Preparation and Characterisation of Super-Hydrophobic Surfaces (pages 3568–3588)

      Colin R. Crick and Ivan P. Parkin

      Version of Record online: 5 MAR 2010 | DOI: 10.1002/chem.200903335

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      Simply super! The interest in highly water-repellent surfaces has grown in recent years due to the desire for self-cleaning surfaces. This review identifies four methods for the construction of super-hydrophobic surfaces (see figure) along with a summation of the key properties of the surface that result in hydrophobicity. A summary of the different routes to super-hydrophobicity is also given.

  6. Communications

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

      Selective Ruthenium-Catalyzed N-Alkylation of Indoles by Using Alcohols (pages 3590–3593)

      Sebastian Bähn, Sebastian Imm, Kathleen Mevius, Lorenz Neubert, Annegret Tillack, Jonathan M. J. Williams and Matthias Beller

      Version of Record online: 5 MAR 2010 | DOI: 10.1002/chem.200903144

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      Alcohols for alkylation! The first homogeneous-catalyzed N-alkylations of indoles with aliphatic alcohols proceed under transfer hydrogenation conditions. By the use of the Shvo catalyst and p-toluenesulfonic acid (PTSA) this atom-efficient reaction occurs highly selectively with water formed as the only byproduct (see scheme).

    2. Biomimetic Synthesis

      Concise Access to a Model of the Marine Alkaloid Halicyclamine A through Macrocycle-Forming Addition of a 5-Aminopenta-2,4-dienal onto a 2,3-Dihydropyridinium Salt (pages 3594–3597)

      Isabelle Sinigaglia, Tuan Minh Nguyen, Jean-Charles Wypych, Bernard Delpech and Christian Marazano

      Version of Record online: 28 FEB 2010 | DOI: 10.1002/chem.201000142

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      A biomimetic synthesis of a model compound for the marine alkaloid halicyclamine A is reported that involves a macrocyclization through the intramolecular addition of a 5-aminopenta-2,4-dienal onto a 2,3-dihydropyridinium salt generated in situ (see scheme). In this way, a monomacrocyclic model, with the same relative stereochemistry as that of the natural product, was obtained.

    3. Template-Assisted Synthesis

      Designed Smart System of the Sandwiched and Concentric Architecture of RuO2/C/RuO2 for High Performance in Electrochemical Energy Storage (pages 3598–3603)

      Yu Wang, Ce Yao Foo, Tun Kai Hoo, Mark Ng and Jianyi Lin

      Version of Record online: 28 FEB 2010 | DOI: 10.1002/chem.200903133

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      Energy storage: A sandwiched and concentric architecture of RuO2/C/RuO2 has been successfully synthesized through a template-assisted approach. This architecture exhibits novelty and innovation in the designed synthesis of hierarchical and functional systems and performed well in electrochemical testing, especially presenting excellent specific capacitance over very high scan rates (see figure).

    4. Nanoparticles

      Switching On Luminescence in Nucleotide/Lanthanide Coordination Nanoparticles via Synergistic Interactions with a Cofactor Ligand (pages 3604–3607)

      Carole Aimé, Ryuhei Nishiyabu, Ryosuke Gondo and Nobuo Kimizuka

      Version of Record online: 28 FEB 2010 | DOI: 10.1002/chem.201000007

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      Coordination nanoparticles: Hydroxypicolinic acid (1) is easily incorporated into coordination nanoparticles (CNPs) self-assembled from nucleotides and terbium ions without impairing nanoparticle morphology. Compound 1 acts as a cofactor ligand that coordinates to Tb3+ ions that exist in the coordination networks, and this switches on the luminescence of CNPs (see graphic).

    5. Superparamagnetism

      Highly Water-Soluble Superparamagnetic Ferrite Colloidal Spheres with Tunable Composition and Size (pages 3608–3612)

      Wei Cheng, Kaibin Tang and Jie Sheng

      Version of Record online: 2 MAR 2010 | DOI: 10.1002/chem.201000014

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      From green to red: Highly water-soluble superparamagnetic monodisperse ferrite colloidal spheres with tunable size and composition have been prepared by a simple one-step hydrothermal method. The zinc ferrite colloidal spheres show composition-dependent saturation magnetization. Surprisingly, the Z0.41Fe0.59Fe2O4 colloidal sphere aqueous suspension can be used for constructing photonic crystals (see figure).

    6. Bioinorganic Chemistry

      Synthesis, Structural Characterisation and Quadruplex DNA Binding Studies of a New Gold(III) Pyrazolylpyridine Complex (pages 3613–3616)

      Kogularamanan Suntharalingam, Deepali Gupta, Pablo J. Sanz Miguel, Bernhard Lippert and Ramon Vilar

      Version of Record online: 24 FEB 2010 | DOI: 10.1002/chem.200903501

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      A golden quadruplex DNA: A new gold(III) pyrazolylpyridine complex has been synthesised and structurally characterised. The complex displays π–π interactions in the solid state. The DNA binding properties of the complex have been studied by fluorescent intercalator displacement assay, surface plasmon resonance and circular dichroism. These have shown that the complex interacts strongly with quadruplex DNA, in particular with c-myc. CD spectroscopy has also shown the ability of the complex to template the formation of a quadruplex structure from a singly stranded sequence of telomeric DNA (see picture for a qualitative docking of the complex on top of a quadruplex DNA structure).

    7. Single-Walled Nanotubes

      Label-Free Colorimetric Detection of Single Nucleotide Polymorphism by Using Single-Walled Carbon Nanotube Intrinsic Peroxidase-Like Activity (pages 3617–3621)

      Yujun Song, Xiaohui Wang, Chao Zhao, Konggang Qu, Jinsong Ren and Xiaogang Qu

      Version of Record online: 28 FEB 2010 | DOI: 10.1002/chem.200902643

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      SWNTs possess intrinsic peroxidase-like activity, catalyzing the reaction of peroxidase substrate 3,3,5,5-tetramethylbenzidene (TMB) in the presence of H2O2 to produce a color reaction. Here SWNTs have been used for label-free colorimetric detection of disease-associated single-nucleotide polymorphism with a direct detection limit of 1 nM.

    8. NMR Spectroscopy

      Residual Dipolar Couplings (RDCs) Analysis of Small Molecules Made Easy: Fast and Tuneable Alignment by Reversible Compression/Relaxation of Reusable PMMA Gels (pages 3622–3626)

      Chakicherla Gayathri, Nicolay V. Tsarevsky and Roberto R. Gil

      Version of Record online: 5 MAR 2010 | DOI: 10.1002/chem.200903378

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      Tuneable RDCs: A fast and tunable method for measuring anisotropic NMR parameters using variable compression/relaxation of clean and reusable PMMA gels in CDCl3 is introduced (see picture). No special devices are needed. The configuration and conformation of small molecules can be determined by using the RDC slopes without the need for performing a control experiment in isotropic conditions.

  7. Full Papers

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

      Stabilization of High-Valent FeIVS6-Cores by Dithiocarbamate(1−) and 1,2-Dithiolate(2−) Ligands in Octahedral [FeIV(Et2dtc)3−n(mnt)n](n−1)− Complexes (n=0, 1, 2, 3): A Spectroscopic and Density Functional Theory Computational Study (pages 3628–3645)

      Carsten Milsmann, Stephen Sproules, Eckhard Bill, Thomas Weyhermüller, Serena DeBeer George and Karl Wieghardt

      Version of Record online: 5 MAR 2010 | DOI: 10.1002/chem.200903381

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      High-valent iron: The electronic structures of [FeIII(Et2dtc)3−n(mnt)n]n (mnt=maleonitriledithiolate and Et2dtc=diethyldithiocarbamato; n=3, 2, 1, 0) and their one-electron oxidized analogues have been elucidated and correlated with the structural and spectroscopic parameters of the complexes (see figure). Despite the presence of noninnocent dithiolene ligands, the oxidized complexes are best described as genuine FeIV complexes.

    2. Donor–Accepor Systems

      Construction of SnIV Porphyrin/Trinuclear Ruthenium Cluster Dyads Linked by Pyridine Carboxylates: Photoinduced Electron Transfer in the Marcus Inverted Region (pages 3646–3655)

      Takahiko Kojima, Kakeru Hanabusa, Kei Ohkubo, Motoo Shiro and Shunichi Fukuzumi

      Version of Record online: 5 MAR 2010 | DOI: 10.1002/chem.200902939

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      Saddle up! Saddle-distorted SnIV porphyrin complexes form stable conglomerates with trinuclear Ru clusters with use of pyridine carboxylates as linkers (see figure). These novel dyads exhibit efficient photoinduced electron transfer, in which Sn porphyrin moieties act as electron donors and Ru clusters act as electron acceptors.

    3. Molecule-Based Magnets

      Three-Dimensional Antiferromagnetic Order of Single-Chain Magnets: A New Approach to Design Molecule-Based Magnets (pages 3656–3662)

      Hitoshi Miyasaka, Karin Takayama, Ayumi Saitoh, Sachie Furukawa, Masahiro Yamashita and Rodolphe Clérac

      Version of Record online: 11 FEB 2010 | DOI: 10.1002/chem.200902861

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      Chain gang: By controlling both intra- and interchain magnetic interactions in a new [MnIIINiII] single-chain magnet (SCM) system, an antiferromagnetic (AF) ordered phase has been stabilized below 9.4 K. In this remarkable AF phase, a magnet-type behavior is observed experimentally in direct relation with the intrinsic SCM properties of the isolated chains composing the material.

    4. Anomeric Effect

      Ligand Close Packing, Molecular Compactness, the Methyl Tilt, Molecular Conformations, and a New Model for the Anomeric Effect (pages 3663–3675)

      Ronald J. Gillespie, Edward A. Robinson and Julien Pilmé

      Version of Record online: 22 FEB 2010 | DOI: 10.1002/chem.200902599

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      A new concept: We introduced the concept of compactness (see figure), which states that the equilibrium structure of a molecule is the most compact one. The concept was used to find the lowest energy conformation for molecules with two or more low-energy conformations, including molecules that exhibit the anomeric effect, thus providing a new explanation of this effect. We also used the concept to explain the “methyl tilt”.

    5. Supramolecular Chemistry

      Transcription of Chirality in the Organogel Systems Dictates the Enantiodifferentiating Photodimerization of Substituted Anthracene (pages 3676–3689)

      Arnab Dawn, Tomohiro Shiraki, Shuichi Haraguchi, Hiroki Sato, Kazuki Sada and Seiji Shinkai

      Version of Record online: 11 FEB 2010 | DOI: 10.1002/chem.200902936

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      It takes a soft touch: Photodimerization of an anthracene that bears a chiral organogelator in the gel state produces photodimers with high regio- and enantioselectivities (see figure). The degrees of selectivities are different in strong, moderately strong, and weak gels, depending upon microenvironments that are controlled by the nature of the solvent and the gelation temperature.

    6. Template Synthesis

      Control of Biocatalytic Transformations by Programmed DNA Assemblies (pages 3690–3698)

      Ronit Freeman, Etery Sharon, Carsten Teller and Itamar Willner

      Version of Record online: 11 FEB 2010 | DOI: 10.1002/chem.200902559

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      Controlled inhibition: Supramolecular complexes of aptamer subunits or Y-shaped nucleic acid structures act as templates for the programmed inhibition of enzymes or the activation of enzyme cascades (see picture). The modification of aptamer subunits causes the inhibition of the catalytic activity of choline oxidase (ChOx) by methylene blue. In another approach, the channeling of H2O2 from glucose oxidase (GOx) to horseradish peroxidase (HRP) was used to generate a reporter system. ABTS2−=azino[bis(3-ethylbenzthiazoline-6-sulfonic acid)].

    7. Dendrimers

      Aggregation-Controlled Excimer Emission from Anthracene-Containing Polyamidoamine Dendrimers (pages 3699–3706)

      P. K. Lekha and Edamana Prasad

      Version of Record online: 8 FEB 2010 | DOI: 10.1002/chem.200902391

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      Tunable excimer emission from anthracene-modified polyamidoamine (PAMAM) dendrimers was achieved by controlling their aggregation propensity in an acetonitrile–water mixture. Since the aggregates are pre-arranged in the ground state, they readily form excimers on photoexcitation. Different types of anthracene excimers can be generated by altering the excitation wavelength and pH of the medium (see schematic; CAC= critical aggregation concentration).

    8. Domino Reactions

      Synthesis of Benzo- and Naphthoquinonyl Boronic Acids: Exploring the Diels–Alder Reactivity (pages 3707–3719)

      Marcos Veguillas, Maria C. Redondo, Isabel García, María Ribagorda and M. Carmen Carreño

      Version of Record online: 19 FEB 2010 | DOI: 10.1002/chem.200902796

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      Highly reactive quinone dienophiles: The electron-withdrawing character of the boronic acid and its hydrogen bonding with the quinone carbonyl group are the key factors that induce high reactivity. The evolution of the Diels–Alder adducts through dehydroboration, protodeboronation or in situ oxidation provides a direct access to some otherwise elusive quinone adducts (see scheme).

    9. Sensors

      A Reversible Dual-Response Fluorescence Switch for the Detection of Multiple Analytes (pages 3720–3727)

      Junlong Geng, Ping Liu, Bianhua Liu, Guijian Guan, Zhongping Zhang and Ming-Yong Han

      Version of Record online: 11 FEB 2010 | DOI: 10.1002/chem.200902721

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      On or off? It's a result both ways: A reversible dual fluorescence switch was fabricated, by the modification of the surface of silica nanoparticles with a nitrobenzoxadiazole fluorophore and an organic amine, for the detection of the herbicide 2,4-dichlorophenoxyacetic acid and 2,4,6-trinitrotoluene with opposite-response results (see images; PET: photoinduced electron transfer; FRET: fluorescence resonance energy transfer).

    10. Solid-State Structures

      Synthesis and Molecular Structure of β-Phosphinoyl Carboxamides: An Unexpected Case of Chiral Discrimination of Hydrogen-Bonded Dimers in the Solid State (pages 3728–3735)

      Mateo Alajarín, Carmen López-Leonardo, Ángel Álvarez-García, Pilar Llamas-Lorente, Pilar Sánchez-Andrada, José Berná, Aurelia Pastor, Delia Bautista and Peter G. Jones

      Version of Record online: 16 FEB 2010 | DOI: 10.1002/chem.200901845

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      Only heterodimerisation! Diastereoisomeric β-phosphinoyl propionamides were obtained by the addition of aminophosphanes to diphenylcyclopropenone. An efficient method for the diastereoisomer interconversion has also been implemented. These compounds associate in the solid state, exclusively forming heterodimers of enantiomeric units linked by two bifurcated hydrogen bonds. The oxygen atom of the phosphoryl group of a molecule acts as a dual acceptor of the NH and CH of a neighbouring molecule (see figure).

    11. Asymmetric Catalysis

      Catalytic Asymmetric Synthesis of 3-(α-Hydroxy-β-carbonyl) Oxindoles by a ScIII-Catalyzed Direct Aldol-Type Reaction (pages 3736–3742)

      Ke Shen, Xiaohua Liu, Ke Zheng, Wei Li, Xiaolei Hu, Lili Lin and Xiaoming Feng

      Version of Record online: 19 FEB 2010 | DOI: 10.1002/chem.200903471

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      Easy access: The direct catalytic asymmetric aldol-type reaction of 3-substituted-2-oxindoles with glyoxal derivatives and ethyl trifluoropyruvate was successfully established through ScIII-based enolate activation. 3-(α-Hydroxy-β-carbonyl) oxindoles with vicinal quaternary–tertiary or quaternary–quaternary stereocenters were delivered in up to 93 % yield, 99:1 diastereomeric ratio (dr), and >99 % enantiomeric excess (ee) under mild conditions (see scheme).

    12. Polymers

      Synthesis and Photovoltaic Properties of Cyclopentadithiophene-Based Low-Bandgap Copolymers That Contain Electron-Withdrawing Thiazole Derivatives (pages 3743–3752)

      In Hwan Jung, Jinyoung Yu, Eunjae Jeong, Jinseck Kim, Sooncheol Kwon, Hoyoul Kong, Kwanghee Lee, Han Young Woo and Hong-Ku Shim

      Version of Record online: 16 FEB 2010 | DOI: 10.1002/chem.200903064

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      Mind the bandgap: Four types of cyclopentadithiophene (CDT)-based low-bandgap copolymers with two thiazole derivatives based on thiazolothiazole (TZ) and bithiazole (BT) structures have been synthesized (see picture for examples). The internal charge-transfer interaction between the electron-sufficient CDT unit and electron-deficient TZ or BT units in the polymeric backbone induces a low bandgap.

    13. Energetic Materials

      Energetic Salts Based on Monoanions of N,N-Bis(1H-tetrazol-5-yl)amine and 5,5′-Bis(tetrazole) (pages 3753–3762)

      Yong Guo, Guo-Hong Tao, Zhuo Zeng, Haixiang Gao, Damon A. Parrish and Jean'ne M. Shreeve

      Version of Record online: 11 FEB 2010 | DOI: 10.1002/chem.200902951

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      An explosive discovery: Salts based on the 5-(tetrazol-5-ylamino)tetrazolate (HBTA) anion were fully characterized (see scheme), including solid-state 13C NMR spectroscopy. Predicted detonation pressures and detonation velocities are 19.4–33.6 GPa and 7677–9487 m s−1.

    14. Hydrogen Storage

      Amminelithium Amidoborane Li(NH3)NH2BH3: A New Coordination Compound with Favorable Dehydrogenation Characteristics (pages 3763–3769)

      Guanglin Xia, Xuebin Yu, Yanhui Guo, Zhu Wu, Chuanzhen Yang, Huangkun Liu and Shixue Dou

      Version of Record online: 15 FEB 2010 | DOI: 10.1002/chem.200903220

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      Hydrogen storage system: Lithium amidoborane, LiNH2BH3, has been shown to absorb/desorb ammonia at room temperature in a reversible manner. The product amminelithium amidoborane, Li(NH3)NH2BH3, started to release hydrogen at about 40 °C and reached its peak at 71 °C, a much lower temperature than in the case of the pure LiNH2BH3.

    15. Salen Ligands

      Photoisomerization of a Maleonitrile-Type Salen Schiff Base and Its Application in Fine-Tuning Infinite Coordination Polymers (pages 3770–3782)

      Chun-Wei Lin, Pi-Tai Chou, Yong-Hong Liao, Ying-Chih Lin, Ching-Ting Chen, Yu-Chun Chen, Chin-Hung Lai, Bo-So Chen, Yi-Hung Liu, Chih-Chieh Wang and Mei-Lin Ho

      Version of Record online: 16 FEB 2010 | DOI: 10.1002/chem.200902500

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      The absence or presence of light determines whether the synthesis of salen ligand 1 affords the Z or E isomer (1Z or 1E, respectively; see upper images in the picture), which have distinctly different photophysical properties. Photoinduced 1Z[RIGHTWARDS ARROW]1E isomerization takes place due to a charge-transfer reaction. Compound 2, a strategically designed analogue of 1 bearing carboxyl groups, was also prepared, and its isomers 2Z and 2E exhibited remarkable differences in the morphology (nanostructure) of their infinite coordination polymers with ZnII (lower images).

    16. C[BOND]C Coupling

      Transition-Metal-Free Formal Sonogashira Coupling and α-Carbonyl Arylation Reactions (pages 3783–3790)

      Birgit Prüger, Gretchen E. Hofmeister, Christian Borch Jacobsen, David G. Alberg, Martin Nielsen and Karl Anker Jørgensen

      Version of Record online: 19 FEB 2010 | DOI: 10.1002/chem.200902911

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      Metal-free coupling: Transition-metal-free formal Sonogashira coupling and α-carbonyl arylation reactions have been developed (see scheme; EWG=electron-withdrawing group, BT=benzothiazol-2-yl). Both transformations proceed through a key intermediate, which is generated by nucleophilic aromatic substitution (SNAr) of β-carbonyl sulfones to electron-deficient aryl fluorides.

    17. Micelles

      DNA-Based Micelles: Synthesis, Micellar Properties and Size-Dependent Cell Permeability (pages 3791–3797)

      Haipeng Liu, Zhi Zhu, Huaizhi Kang, Yanrong Wu, Kwame Sefan and Weihong Tan

      Version of Record online: 16 FEB 2010 | DOI: 10.1002/chem.200901546

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      Amphiphilic DNA spontaneously self-assembles into monodispersed micelle structures with a lipid core and a DNA corona in water. Experimental testing showed that these micelles have excellent thermal stability and cell membrane permeability (see scheme).

    18. Natural Product Hybrids

      Two Versatile and Parallel Approaches to Highly Symmetrical Open and Closed Natural Product-Based Structures (pages 3798–3814)

      Héctor E. Montenegro, Pedro Ramírez-López, María C. de la Torre, María Asenjo and Miguel A. Sierra

      Version of Record online: 16 FEB 2010 | DOI: 10.1002/chem.200903264

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      Natural product hybrid structures: Monoaddition of bis(alkynyl) dilithium reagents to various natural products bearing a carbonyl group has been used to obtain the scaffolds needed to access diverse natural product hybrids. Oligomeric steroid-, terpene-, and alkaloid-based derivatives incorporating diverse spacers to join these natural product scaffolds have been readily prepared from different alkynyl substrates in high-yielding Cu-mediated single-step reactions (see scheme).

    19. Ionic Liquids

      Speciation of Aluminium in Mixtures of the Ionic Liquids [C3mpip][NTf2] and [C4mpyr][NTf2] with AlCl3: An Electrochemical and NMR Spectroscopy Study (pages 3815–3826)

      Theo Rodopoulos, Leanne Smith, Michael D. Horne and Thomas Rüther

      Version of Record online: 9 FEB 2010 | DOI: 10.1002/chem.200902753

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      Who's responsible? Aluminium speciation in two bis(trifluoromethylsulfonyl)amide (NTf2)-based ionic liquids (ILs) containing AlCl3 was investigated by electrochemistry and NMR spectroscopy. Numerous Al-containing species were detected in solution (see figure), but [AlCl3(NTf2)] is believed to be the one responsible for Al electrodeposition in both ILs.

    20. NMR Spectroscopy

      3-Mercapto-2,6-Pyridinedicarboxylic Acid: A Small Lanthanide-Binding Tag for Protein Studies by NMR Spectroscopy (pages 3827–3832)

      Bradley Man, Xun-Cheng Su, Haobo Liang, Shane Simonsen, Thomas Huber, Barbara A. Messerle and Gottfried Otting

      Version of Record online: 16 FEB 2010 | DOI: 10.1002/chem.200902904

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      Small is beautiful: 3-Mercapto-2,6-pyridinedicarboxylic acid (3MDPA) is a novel tag for site-specific attachment of lanthanides and Co2+ to proteins, (see figure). It is the smallest lanthanide-binding tag yet reported and produces very different pseudocontact shifts than the previously published 4MMDPA tag. Its small size and rigidity make the 3MDPA tag a powerful tool for structural investigations of proteins by NMR spectroscopy.

    21. Polyhedral Oligosilsesquioxanes

      Octakis(3-azidopropyl)octasilsesquioxane: A Versatile Nanobuilding Block for the Efficient Preparation of Highly Functionalized Cube-Octameric Polyhedral Oligosilsesquioxane Frameworks Through Click Assembly (pages 3833–3841)

      Beatriz Trastoy, M. Eugenia Pérez-Ojeda, Roberto Sastre and Jose Luis Chiara

      Version of Record online: 16 FEB 2010 | DOI: 10.1002/chem.200902422

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      Clickety click! A one-step synthesis of an octaazidesilsesquioxane with perfect 3D cubic symmetry has been realized from a commercially available silsesquioxane by using an efficient diazo-transfer reaction under very mild conditions (see scheme). This compound is an excellent nanobuilding block that can be readily octafunctionalized with a range of terminal alkynes by copper(I)-catalyzed 1,3-dipolar azide–alkyne cycloaddition to provide new functional nanocages, maintaining a perfect 3D cubic symmetry.

    22. Asymmetric Synthesis

      Water—More Than Just a Green Solvent: A Stereoselective One-Pot Access to All-Chiral Tetrahydronaphthalenes in Aqueous Media (pages 3842–3848)

      Bin Tan, Di Zhu, Lihong Zhang, Pei Juan Chua, Xiaofei Zeng and Guofu Zhong

      Version of Record online: 11 FEB 2010 | DOI: 10.1002/chem.200902932

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      A key role for water: A facile and highly stereoselective means of constructing heavily functionalized chiral tetrahydronaphthalene skeletons fused with an oxazolidine moiety has been developed. The strategy is based on an organocatalytic tandem Michael/nitrone formation/intramolecular [3+2] nitrone–olefin cycloaddition in aqueous media using rationally designed substrates. The water used as the reaction medium not only represents an environmentally benign solvent, but also helps to improve the reactivity and stereoselectivity.

    23. Green Catalysis

      Microwave Irradiation for the Facile Synthesis of Transition-Metal Nanoparticles (NPs) in Ionic Liquids (ILs) from Metal–Carbonyl Precursors and Ru-, Rh-, and Ir-NP/IL Dispersions as Biphasic Liquid–Liquid Hydrogenation Nanocatalysts for Cyclohexene (pages 3849–3858)

      Christian Vollmer, Engelbert Redel, Khalid Abu-Shandi, Ralf Thomann, Haresh Manyar, Christopher Hardacre and Christoph Janiak

      Version of Record online: 24 FEB 2010 | DOI: 10.1002/chem.200903214

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      Recycle and reuse: Cr, Mo, W, Mn, Re, Fe, Ru, Os, Co, Rh, and Ir metal nanoparticles (M-NPs) have been obtained by microwave, thermal, or photolytic decomposition from [Mx(CO)y] in the ionic liquid (IL) 1-butyl-3-methylimidazolium tetrafluoroborate. Ru-, Rh-, and Ir-NP/IL dispersions function as highly active and easily recyclable hydrogenation catalysts (see graphic).

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      Version of Record online: 16 MAR 2010 | DOI: 10.1002/chem.201090056

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