Chemistry - A European Journal

Cover image for Vol. 18 Issue 19

May 7, 2012

Volume 18, Issue 19

Pages 5781–6103

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Communications
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    1. You have free access to this content
      Cover Picture: Luminescent Blooming of Dendronic Carbon Nanotubes through Ion-Pairing Interactions with an EuIII Complex (Chem. Eur. J. 19/2012) (page 5781)

      Laura Maggini, Dr. Francesca Maria Toma, Dr. Luigi Feruglio, Joanna M. Malicka, Dr. Tatiana Da Ros, Dr. Nicola Armaroli, Prof. Maurizio Prato and Dr. Davide Bonifazi

      Version of Record online: 3 MAY 2012 | DOI: 10.1002/chem.201290074

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      Strongly emitting hybrids are obtained when lanthanide complexes are blended with carbon nanotubes, in which the structural and electronic properties of both constituents are preserved. In their Full paper on page 5889 ff., D. Bonifazi, M. Prato, N. Armaroli et al. describe how a multiwalled carbon-nanotube scaffold was covalently functionalized with a second-generation, positively charged polyamidoamine dendron, and eventually coupled with a negatively charged and highly luminescent EuIII complex through electrostatic interactions to afford a bright, luminescent, and stable hybrid material. The high dispersibility and the small amounts required to obtain intense luminescent outputs make it a promising hybrid luminophore for photonic applications.

  2. Graphical Abstract

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

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    4. News
    5. Review
    6. Communications
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  4. Review

    1. Top of page
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    1. Ring-Closing Metathesis

      Temporary Silicon-Tethered Ring-Closing Metathesis: Recent Advances in Methodology Development and Natural Product Synthesis (pages 5800–5824)

      Dr. Alen Čusak

      Version of Record online: 11 APR 2012 | DOI: 10.1002/chem.201103186

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      All in a tether! Temporary silicon-tethered ring-closing metathesis has been established as a versatile strategy for the construction of medium-sized silacycles. Based on the proper selection of structural requirements in close proximity of the reactive olefins, the RCM reaction can easily provide access to (Z)- or (E)-alkenes in eight-membered siloxacycles. The review displays the numerous applications of this rewarding strategy to the methodology development and target-directed synthesis (see figure).

  5. Communications

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    4. News
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    1. Synthetic Methods

      A Versatile Enantioselective Synthesis of Azabicyclic Ring Systems: A Concise Total Synthesis of (+)-Grandisine D and Unnatural Analogues (pages 5826–5831)

      Dr. Olugbeminiyi O. Fadeyi, Timothy J. Senter, Kristopher N. Hahn and Prof. Craig W. Lindsley

      Version of Record online: 30 MAR 2012 | DOI: 10.1002/chem.201200629

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      Closing in on azacines: We have developed a new six step approach for the rapid and enantioselective synthesis of indolizidine, pyrrolo[1,2-a]azepine, and pyrrolo[1,2-a]azocine azabicyclic systems and their respective lactam congeners, which are found in a host of natural products as well as pharmaceutical preparations. This protocol enables a concise enantioselective total synthesis of (+)-grandisine D in 16.4 % overall yield from commercial materials (see scheme).

    2. Molecular Recognition

      Experimental Evaluation of CH–π Interactions in a Protein Core (pages 5832–5836)

      Christopher J. Pace, Diane Kim and Prof. Jianmin Gao

      Version of Record online: 30 MAR 2012 | DOI: 10.1002/chem.201200334

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      CH–π stacks up! Using the protein α2D as a model system, we estimate that a CH–π contact between cyclohexylalanine (Cha) and phenylalanine (F) contributes approximately −0.7 kcal mol−1 to the protein stability. The stacking F–Cha pairs are sequestered in the core of the protein, where water interference does not exist (see figure). Therefore, the observed energetic gain should represent the inherent magnitude and upper limit of the CH–π interactions.

    3. Thermosensitive Dendrimers

      Amphiphilic Folded Dendrimer Discs and Their Thermosensitive Self-Assembly in Water (pages 5837–5842)

      Dr. Tamer El Malah, Simone Rolf, Dr. Steffen M. Weidner, Prof. Dr. Andreas F. Thünemann and Prof. Dr. Stefan Hecht

      Version of Record online: 29 MAR 2012 | DOI: 10.1002/chem.201200414

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      Folded dendrimers with peripheral ether side chains show a thermally induced hierarchical aggregation process, in which the transition temperature and the dimensions of the aggregates can readily be tuned via the generation number (see figure).

    4. Biosensors

      Functionalized Fe3O4 Nanoparticles for Detecting Zinc Ions in Living Cells and Their Cytotoxicity (pages 5843–5847)

      Gyusik Kang, Hyunjong Son, Jung Mi Lim, Dr. Hee-Seek Kweon, Prof. Dr. In Su Lee, Prof. Dr. Dongmin Kang and Prof. Dr. Jong Hwa Jung

      Version of Record online: 19 APR 2012 | DOI: 10.1002/chem.201200294

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      The zinc tank: A new fluoro-chromogenic chemosensor based on BODIPY-functionalized Fe3O4 nanoparticles (1) has been prepared. Chemoprobe 1 exhibits high selectivity for Zn2+ over other competing metal ions tested. Moreover, confocal microscopy experiments established that 1 can be used for detecting Zn2+ levels in living cells (see figure).

    5. Hybrid Materials

      Exciplex Formation and Energy Transfer in a Self-Assembled Metal–Organic Hybrid System (pages 5848–5852)

      Ritesh Haldar, K. Venkata Rao, Subi J. George and Tapas Kumar Maji

      Version of Record online: 19 APR 2012 | DOI: 10.1002/chem.201103827

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      Exciting assemblies: A metal–organic self-assembly of pyrenebutyric acid (PBA), 1,10-phenanthroline (o-phen), and MgII shows solid-state fluorescence originating from a 1:1 PBA–o-phen exciplex. This exciplex fluorescence is sensitized by another residual PBA chromophore through an excited-state energy-transfer process. The solvent polarity modulates the self-assembly and the corresponding exciplex as well as the energy transfer, resulting in tunable emission of the hybrid (see figure).

    6. Electrochemical Synthesis

      Electrochemical Synthesis of a Thiophene-Containing Cyclo[9]pyrrole (pages 5853–5859)

      Dr. Thanh-Tuan Bui, Adriana Iordache, Zhongrui Chen, Vladimir V. Roznyatovskiy, Prof. Eric Saint-Aman, Jong Min Lim, Byung Sun Lee, Sudip Ghosh, Prof. Jean-Claude Moutet, Prof. Jonathan L. Sessler, Prof. Dongho Kim and Dr. Christophe Bucher

      Version of Record online: 29 MAR 2012 | DOI: 10.1002/chem.201200196

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      A new member of the cyclo[n]pyrrole class of expanded porphyrins could be prepared from the corresponding thiophene-containing terpyrrole precursor through use of a mild electrochemical oxidative procedure. The isolated macrocycle, featuring nine heterocyclic subunits directly connected through their α,α′-positions, is the largest cyclo[n]pyrrole derivative reported to date (see figure).

    7. Iron Catalysis

      Iron Thiolate Complexes: Efficient Catalysts for Coupling Alkenyl Halides with Alkyl Grignard Reagents (pages 5860–5863)

      Dr. Gérard Cahiez, Dr. Olivier Gager, Dr. Julien Buendia and Cindy Patinote

      Version of Record online: 29 MAR 2012 | DOI: 10.1002/chem.201200184

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      Ironing out the kinks: Efficient new catalytic systems based on iron thiolates are described for the iron-catalyzed cross-coupling of alkyl Grignard reagents with alkenyl halides (see scheme). The reaction is highly chemo- and stereoselective. With this new procedure, the use of N-methylpyrrolidone as a co-solvent is no longer required.

    8. Tandem Catalysis

      Synergistic Effect of Palladium and Copper Catalysts: Catalytic Cyclizative Dimerization of ortho-(1-Alkynyl)benzamides Leading to Axially Chiral 1,3-Butadienes (pages 5864–5868)

      Dr. Bo Yao, Carole Jaccoud, Dr. Qian Wang and Prof. Dr. Jieping Zhu

      Version of Record online: 4 APR 2012 | DOI: 10.1002/chem.201200215

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      Two is better than one: In the presence of Pd(OAc)2 and Cu(OAc)2, o-(1-alkynyl)benzamides 1 were converted into bis-iminobenzoisofurans with an axially chiral 1,3-diene 2 unit. The coexistence of both Pd and Cu catalysts was found to be essential for both the cyclizative dimerization process and for the observed unusual cyclization mode.

    9. Asymmetric Catalysis

      Chiral Phosphoric Acid-Catalyzed Enantioselective Three-Component Povarov Reaction Using Cyclic Enethioureas as Dienophiles: Stereocontrolled Access to Enantioenriched Hexahydropyrroloquinolines (pages 5869–5873)

      Guillaume Dagousset, Dr. Pascal Retailleau, Dr. Géraldine Masson and Prof. Dr. Jieping Zhu

      Version of Record online: 29 MAR 2012 | DOI: 10.1002/chem.201200523

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      Three become one: Phosphoric acid-catalyzed enantioselective three-component Povarov reactions of aldehydes, anilines, and endocyclic enethioureas have been developed (see scheme). This process afforded hexahydropyrroloquinolines in high yields with excellent diastereo- and enantioselectivities. The presence of the thiourea functionality is crucial for the enantioselectivity of the reaction.

    10. Hybrid Nanostructures

      Synthesis and Photocatalytic Properties of Cu2S–Pd4S Hybrid Nanoplates (pages 5874–5878)

      Kyu-Hwan Park, Young Wook Lee, Dongheun Kim, Kyungwon Lee, Prof. Dr. Sang Bok Lee and Prof. Dr. Sang Woo Han

      Version of Record online: 29 MAR 2012 | DOI: 10.1002/chem.201200025

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      Hex appeal! Cu2S–Pd4S hybrid nanocrystals with a novel hexagonal nanoplate structure were prepared in high yield by a simple one-pot synthetic method (see figure). Successful synthesis of this unique structure was achieved through a consecutive thermolysis process. The Cu2S–Pd4S hybrid nanoplates exhibited substantially higher photocatalytic activities than pure Cu2S nanoplates.

  6. Full Papers

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

      Rapid Preparation of Multifunctional Surfaces for Orthogonal Ligation by Microcontact Chemistry (pages 5880–5888)

      Christian Wendeln, Stefan Rinnen, Christian Schulz, Tobias Kaufmann, Prof. Dr. Heinrich F. Arlinghaus and Prof. Dr. Bart Jan Ravoo

      Version of Record online: 16 APR 2012 | DOI: 10.1002/chem.201103422

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      Printing revolution: Self-assembled monolayers on glass can be patterned by microcontact printing to provide arrays of up to four different functional groups, each of which can be addressed independently (see figure).

    2. Luminescent Materials

      Luminescent Blooming of Dendronic Carbon Nanotubes through Ion-Pairing Interactions with an EuIII Complex (pages 5889–5897)

      Laura Maggini, Dr. Francesca Maria Toma, Dr. Luigi Feruglio, Joanna M. Malicka, Dr. Tatiana Da Ros, Dr. Nicola Armaroli, Prof. Maurizio Prato and Dr. Davide Bonifazi

      Version of Record online: 4 APR 2012 | DOI: 10.1002/chem.201200237

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      Red light from the dark: Combining a positively charged dendronic carbon nanotube (CNT) and a negatively charged EuIII complex, a unique hybrid material characterized by an intense luminescence has been prepared, proving for the first time that ion-pairing interactions are a potent supramolecular tool to assemble CNT materials with potentially relevant applicative perspectives (see figure).

    3. Radical Chemistry

      Extraordinary Radical Scavengers: 4-Mercaptostilbenes (pages 5898–5905)

      Xiao-Yan Cao, Jie Yang, Dr. Fang Dai, De-Jun Ding, Yan-Fei Kang, Fu Wang, Xiu-Zhuang Li, Guo-Yun Liu, Sha-Sha Yu, Dr. Xiao-Ling Jin and Prof. Dr. Bo Zhou

      Version of Record online: 27 MAR 2012 | DOI: 10.1002/chem.201103897

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      Scavenger in the rye: This work demonstrates that 4-mercaptostilbenes are extraordinary radical scavengers, and that the substitution of a 4-SH for a 4-OH group in the stilbene scaffold is an important strategy to improve the radical-scavenging activity of naturally occurring resveratrol (see scheme). Surprisingly, in methanol, some of the new compounds are 104-times more active than resveratrol. The detailed radical-scavenging mechanisms were discussed based on acidified-kinetic analysis.

    4. Magnetic Properties

      What Controls the Magnetic Interaction in bis-μ-Alkoxo MnIII Dimers? A Combined Experimental and Theoretical Exploration (pages 5906–5918)

      Nelly Berg, Thayalan Rajeshkumar, Stephanie M. Taylor, Prof. Euan K. Brechin, Dr. Gopalan Rajaraman and Dr. Leigh F. Jones

      Version of Record online: 29 MAR 2012 | DOI: 10.1002/chem.201102828

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      Dimer?‥Dozens! The synthesis, magnetic characterisation and theoretical studies of a series of bis-μ-alkoxide bridged MnIII dinuclear complexes of general formula [MnIII2(μ-OR)2(biphen)2(ROH)x(L)y] (where R=Me, Et; H2biphen=2,2′-biphenol and L=terminally bonded N-donor ligand) is described. Building on these findings we have categorised all known μ-OR bridged MnIII dinuclear complexes into one of three classifications (see figure).

    5. Corroles

      Synthesis of Nickel(II) Azacorroles by Pd-Catalyzed Amination of α,α′-Dichlorodipyrrin NiII Complex and Their Properties (pages 5919–5923)

      Miki Horie, Yosuke Hayashi, Dr. Shigeru Yamaguchi and Prof. Dr. Hiroshi Shinokubo

      Version of Record online: 27 MAR 2012 | DOI: 10.1002/chem.201200485

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      Synthesis ofmeso-aryl azacorroles was achieved by Buchwald–Hartwig amination of a dipyrrin NiII complex through C[BOND]N and C[BOND]C coupling (see scheme). The structure of azacorrole was elucidated by X-ray diffraction analysis, which revealed azacorrole to be aromatic with [17]triaza-annulene 18π conjugation. Azacorrole underwent site-selective N- and C-acylation as depicted.

    6. Photomagnetism

      Photomagnetism of a sym-cis-Dithiocyanato Iron(II) Complex with a Tetradentate N,N′-Bis(2-pyridylmethyl)1,2-ethanediamine Ligand (pages 5924–5934)

      Dr. Jean-François Létard, Dr. Saket Asthana, Helena J. Shepherd, Dr. Philippe Guionneau, Dr. André E. Goeta, Naohiko Suemura, Ryuta Ishikawa and Prof. Sumio Kaizaki

      Version of Record online: 27 MAR 2012 | DOI: 10.1002/chem.201102637

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      A photomagnetic personality: cis-[Fe(picen)(NCS)2] (picen=N,N′-bis(2-pyridylmethyl)1,2-ethanediamine) was characterized by an extremely slow spin-equilibration in the vicinity of the thermal spin-transition. Single-crystal X-ray diffraction as a function of speed-cooling at 30 K revealed the mechanism of the spin-crossover in this complex as well as some direct relationships between its structural properties and its spin state.

    7. Drug Delivery

      Biocompatible Triplex Ag@SiO2@mTiO2 Core–Shell Nanoparticles for Simultaneous Fluorescence-SERS Bimodal Imaging and Drug Delivery (pages 5935–5943)

      Dr. Yunqing Wang, Prof. Lingxin Chen and Ping Liu

      Version of Record online: 29 MAR 2012 | DOI: 10.1002/chem.201103571

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      Armored core–shell: Ag@SiO2@mTiO2 core-shell nanoparticles were synthesized for simultaneous fluorescence-surface-enhanced Raman scattering (F-SERS) bimodal imaging and doxorubicin delivery. The drug-loaded F-SERS dots retained their activity toward tumor cells and exhibited strong fluorescence when excited at 460 nm. Characteristic 4-mercaptopyridine SERS signals were detected when excited at 632.8 nm, both in solution and inside living cells.

    8. Glycoproteins

      Homogeneous Human Complex-Type Oligosaccharides in Correctly Folded Intact Glycoproteins: Evaluation of Oligosaccharide Influence On Protein Folding, Stability, and Conformational Properties (pages 5944–5953)

      Dr. Yasuhiro Kajihara, Yasutaka Tanabe, Shun Sasaoka and Dr. Ryo Okamoto

      Version of Record online: 23 MAR 2012 | DOI: 10.1002/chem.201103428

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      Sugar rush: The influence of human complex-type oligosaccharides on protein conformation was carried out by using crambin (shown in figure) and ovomucoide model glycoproteins. Glycosylation was carried out on secondary structures at selected positions. Glycosylation of the α-helix and β-sheets did not disturb the protein folding process or conformation, but glycosylation at the loop position between the antiparallel β-strands did.

    9. Luminescence

      Phase- and Size-Controllable Synthesis of Hexagonal Upconversion Rare-Earth Fluoride Nanocrystals through an Oleic Acid/Ionic Liquid Two-Phase System (pages 5954–5969)

      Meng He, Dr. Peng Huang, Dr. Chunlei Zhang, Jiebing Ma, Prof. Rong He and Prof. Daxiang Cui

      Version of Record online: 27 MAR 2012 | DOI: 10.1002/chem.201102419

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      Two-phase synthesis: A facile, user- and environmentally friendly (n-octanol-induced) oleic acid (OA)/ionic liquid (IL) two-phase system for the phase- and size-controllable synthesis of small (<50 nm) water-soluble hexagonal rare earth (La, Gd, and Y) fluoride nanocrystals with uniform morphologies is described (see figure).

    10. Niobium Oxynitrides

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      Niobium(V) Oxynitride: Synthesis, Characterization, and Feasibility as Anode Material for Rechargeable Lithium-Ion Batteries (pages 5970–5978)

      Dr. Xiao-Jun Wang, Dr. Frank Krumeich, Dr. Michael Wörle, Prof. Dr. Reinhard Nesper, Dr. Laurent Jantsky and Prof. Dr. Helmer Fjellvåg

      Version of Record online: 29 MAR 2012 | DOI: 10.1002/chem.201102653

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      Choose O or N? Nanoparticles of NbON (see figure) have been synthesized and the composition was determined as NbO1.3(1)N0.7(1) and not NbON. Carbon-coated oxynitride nanoparticles showed promising electrochemical behavior versus Li; the measured capacity was 500 and 100 A h kg−1 during first discharge and stabilized at 250 and 80 A h kg−1 in subsequent cycles when the cutoff potential was set at 0.05 and 1 V, respectively.

    11. Metal–Organic Frameworks

      Controlled Construction of Metal–Organic Frameworks: Hydrothermal Synthesis, X-ray Structure, and Heterogeneous Catalytic Study (pages 5979–5986)

      Dr. Rupam Sen, Debraj Saha and Dr. Subratanath Koner

      Version of Record online: 27 MAR 2012 | DOI: 10.1002/chem.201102953

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      A systematic approach was used to prepare metal–organic framework compounds with increasing dimensionality by tuning the pH of the medium. By changing the pH from 4 to 8, it has been possible to build-up a novel series of five magnesium-based carboxylate systems from zero-dimensional (0D) to three-dimensional (3D) frameworks (see scheme). The 3D framework compound shows catalytic activity in carbon–carbon bond-forming reactions of various aromatic aldehydes with acetone under heterogeneous conditions.

    12. DNA

      Quadracyclic Adenine: A Non-Perturbing Fluorescent Adenine Analogue (pages 5987–5997)

      Anke Dierckx, Dr. Francois-Alexandre Miannay, Dr. Nouha Ben Gaied, Søren Preus, Markus Björck, Prof. Dr. Tom Brown and Prof. Dr. L. Marcus Wilhelmsson

      Version of Record online: 21 MAR 2012 | DOI: 10.1002/chem.201103419

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      I can't believe it's not adenine: Fluorescent-base analogues are very important tools for investigating the structure and dynamics of nucleic acid-containing systems. An excellent, thymine-selective adenine analogue, quadracyclic adenine (qA; see figure), which preserves the natural B-form of DNA and has interesting emissive properties, is presented.

    13. DNA Sequencing

      Synthesis, Physicochemical Properties, and Hydrogen Bonding of 4(5)-Substituted 1-H-Imidazole-2-carboxamide, a Potential Universal Reader for DNA Sequencing by Recognition Tunneling (pages 5998–6007)

      Dr. Feng Liang, Dr. Shengqing Li, Prof. Stuart Lindsay and Prof. Peiming Zhang

      Version of Record online: 29 MAR 2012 | DOI: 10.1002/chem.201103306

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      Universal reader is a chemical reagent capable of recognizing all DNA bases and generating distinctive electrical signatures for DNA sequencing by recognition tunneling in nanopores. 1-H-Imidazole-2-carboxamide is designed to be such a molecule owing to its multiple hydrogen bonding sites and variable conformations as well as its π-excessive nature (see figure).

    14. Nucleosides

      Diffusion and Birefringence of Bioactive Dyes in a Supramolecular Guanosine Hydrogel (pages 6008–6014)

      Rabindra Nath Das, Y. Pavan Kumar, Sreenivasarao Pagoti, Dr. Avinash J. Patil and Dr. Jyotirmayee Dash

      Version of Record online: 29 MAR 2012 | DOI: 10.1002/chem.201103814

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      Old before I dye: The K+-ion-mediated self-association of two simple nucleoside building blocks, guanosine and bromoguanosine, produced transparent self-standing supramolecular hydrogels with dendritic nanoarchitectures (see figure) that diffused and released bioactive small molecules and exhibited strong birefringence in the presence of dyes.

    15. Living Radical Polymerization

      Controlled Bimodal Molecular-Weight-Distribution Polymers: Facile Synthesis by RAFT Polymerization (pages 6015–6021)

      Jian Qin, Dr. Lifen Zhang, Hongjuan Jiang, Dr. Jian Zhu, Dr. Zhengbiao Zhang, Dr. Wei Zhang, Dr. Nianchen Zhou, Dr. Zhenping Cheng and Dr. Xiulin Zhu

      Version of Record online: 4 APR 2012 | DOI: 10.1002/chem.201103914

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      Launching a RAFT: A pair of reversible addition–fragmentation chain-transfer (RAFT) agents were used for RAFT polymerization to synthesize well-defined bimodal molecular-weight-distribution (MWD) polymers (see figure). Bimodal higher-molecular-weight polymers and block copolymers with both well-controlled molecular weight and MWD could be prepared easily due to the “living” features of RAFT polymerization.

    16. Cleavage Reactions

      Mechanistic Insight into the N[DOUBLE BOND]N Bond-Cleavage of Azo-Compounds that was Induced by an Al[BOND]Al-bonded Compound [L2−AlII[BOND]AlIIL2−] (pages 6022–6030)

      Yanxia Zhao, Dr. Yanyan Liu, Dr. Ling Yang, Prof. Dr. Jian-Guo Yu, Dr. Shaoguang Li, Prof. Dr. Biao Wu and Prof. Dr. Xiao-Juan Yang

      Version of Record online: 29 MAR 2012 | DOI: 10.1002/chem.201103607

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      Cleaving Las Vegas: An Al[BOND]Al-bonded compound that was ligated by a dianionic α-diimine ligand behaved as a 4e-reductant toward azo-compounds to afford dinuclear Al complexes with bridging arylimido groups through cleavage of the N[DOUBLE BOND]N double bond.

    17. Lithium-Ion Batteries

      Carbon-Decorated Single-Crystalline Ni2P Nanotubes Derived from Ni Nanowire Templates: A High-Performance Material for Li-Ion Batteries (pages 6031–6038)

      Yi Lu, Prof. Jiangping Tu, Qinqin Xiong, Yanqiang Qiao, Jun Zhang, Dr. Changdong Gu, Dr. Xiuli Wang and Prof. Scott X. Mao

      Version of Record online: 29 MAR 2012 | DOI: 10.1002/chem.201103724

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      Batteries not included: Single-crystalline Ni2P/C nanotubes were synthesized for the application of Li-ion batteries by using a Ni nanowire template. They exhibit improved electrochemical performance owing to the stable nanotubular Ni2P structure and the carbon shell.

    18. Reductive Cross-Coupling

      Nickel-Mediated Inter- and Intramolecular Reductive Cross-Coupling of Unactivated Alkyl Bromides and Aryl Iodides at Room Temperature (pages 6039–6048)

      Chang-Song Yan, Prof. Dr. Yu Peng, Xiao-Bo Xu and Prof. Dr. Ya-Wen Wang

      Version of Record online: 30 MAR 2012 | DOI: 10.1002/chem.201200190

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      Nickel coupling: A nickel-mediated intermolecular reductive cross-coupling of unactivated alkyl bromides and aryl iodides at room temperature has been developed and successfully extended to less explored intramolecular versions and tandem cyclizations (see scheme). Highly stereoselective (or stereospecific) synthesis of linear-fused perhydrofuro[2,3-b]furan (pyran) and spiroketal skeletons allows rapid access to medicinally useful building blocks.

    19. Nanostructures

      Ag Nanobelts: Synthesis, Morphological Evolution, and Their Use as Electrocatalysts for Oxygen Reduction (pages 6049–6054)

      Dr. Ning Wang, Dr. Xia Cao, Dr. Quanjing Chen and Prof. Guo Lin

      Version of Record online: 27 MAR 2012 | DOI: 10.1002/chem.201103926

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      Tightening your belt: Ag nanomaterials were synthesized and encapsulated in a poly(o-anisidine) (POA) sheath to form Ag@POA through a redox reaction between AgI ions and an OA monomer. OA acts as a capping agent and as a monomer to form the POA sheath.

    20. Carbene Catalysts

      PEPPSI-Type Palladium Complexes Containing Basic 1,2,3-Triazolylidene Ligands and Their Role in Suzuki–Miyaura Catalysis (pages 6055–6062)

      Daniel Canseco-Gonzalez, Dr. Andrzej Gniewek, Michal Szulmanowicz, Dr. Helge Müller-Bunz, Prof. Dr. Anna M. Trzeciak and Prof. Dr. Martin Albrecht

      Version of Record online: 29 MAR 2012 | DOI: 10.1002/chem.201103719

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      Going nano: PEPPSI-type triazolylidene–palladium complexes containing an easily removable ligand were synthesized and evaluated in aryl–aryl cross-coupling catalysis. Mechanistic investigations revealed an operationally homogeneous catalyst that originates from heterogeneous nanoparticles as the catalyst resting state (see scheme).

    21. Metallacycles

      Synthesis of Planar Chiral Iridacycles by Cationic Metal π-Coordination: Facial Selectivity, and Conformational and Stereochemical Consequences (pages 6063–6078)

      Dr. Jean-Pierre Djukic, Wissam Iali, Dr. Michel Pfeffer and Dr. Xavier-Frédéric Le Goff

      Version of Record online: 30 MAR 2012 | DOI: 10.1002/chem.201103577

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      Planar sailing: Facial selectivity in the π-coordination of racemic pseudo-tetrahedral iridacycles by neutral, monocationic, and biscationic metal centers was influenced by Coulombic imbalance in the coordination sphere of the Ir center. Persistence of the planar chiral iridacycles was ensured by the presence of an electron-donating group, the conformational behavior of which was affected such that it could be considered as another stereogenic center (see figure).

    22. Chemical Vapour Deposition

      Gallium Hydride Complexes Stabilised by Multidentate Alkoxide Ligands: Precursors to Thin Films of Ga2O3 at Low Temperatures (pages 6079–6087)

      Dr. David Pugh, Leanne G. Bloor, Prof. Ivan P. Parkin and Prof. Claire J. Carmalt

      Version of Record online: 27 MAR 2012 | DOI: 10.1002/chem.201103380

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      Wired by hydrides! Molecular precursors derived from gallium hydrides for the deposition of gallium oxide thin films are reported. Using aerosol-assisted chemical vapour deposition techniques, films grown from the hydride-derived precursors are visibly crystalline at unprecedentedly low temperatures (450 °C) and also show the growth of microscopic wires (pictured) close to the aerosol inlet.

    23. Triazole Synthesis

      Amine-Catalyzed [3+2] Huisgen Cycloaddition Strategy for the Efficient Assembly of Highly Substituted 1,2,3-Triazoles (pages 6088–6093)

      Lei Wang, Shiyong Peng, Lee Jin Tu Danence, Yaojun Gao and Prof. Dr. Jian Wang

      Version of Record online: 29 MAR 2012 | DOI: 10.1002/chem.201103393

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      Organocatalyzed triazole synthesis: An enamine-catalyzed strategy has been utilized to fully promote the Huisgen [3+2] cycloaddition on a broad spectrum of unmodified carbonyl compounds and azides, thereby permitting the efficient assembly of a vast pool of highly substituted 1,2,3-triazoles (see scheme). Most importantly, the reaction process exhibited complete regioselectivity with the formation of only one regioisomer.

    24. Cobalt Catalysts

      Amide-Based Nonheme Cobalt(III) Olefin Epoxidation Catalyst: Partition of Multiple Active Oxidants CoV[DOUBLE BOND]O, CoIV[DOUBLE BOND]O, and CoIII[BOND]OO(O)CR (pages 6094–6101)

      Young Joo Song, Min Young Hyun, Jun Ho Lee, Hong Gyu Lee, Jin Hoon Kim, Seung Pyo Jang, Jin Young Noh, Dr. Youngmee Kim, Prof. Dr. Sung-Jin Kim, Prof. Dr. Suk Joong Lee and Prof. Dr. Cheal Kim

      Version of Record online: 29 MAR 2012 | DOI: 10.1002/chem.201103916

      Thumbnail image of graphical abstract

      Split personality: A cobalt complex shows partitioning between the heterolytic and homolytic cleavage of an O[BOND]O bond to afford CoV[DOUBLE BOND]O and CoIV[DOUBLE BOND]O intermediates (see scheme). Under extreme conditions, in which the concentration of an active substrate is very high, the Co[BOND]OOC(O)R species is involved in an epoxidation reaction. In protic solvents, this species undergoes predominantly heterolytic cleavage to produce a CoV[DOUBLE BOND]O species as the dominant epoxidizing intermediate.

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      Preview: Chem. Eur. J. 20/2012 (page 6103)

      Version of Record online: 3 MAY 2012 | DOI: 10.1002/chem.201290077

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