Angewandte Chemie International Edition

Cover image for Vol. 52 Issue 48

November 25, 2013

Volume 52, Issue 48

Pages 12455–12744

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Essay
    11. Minireview
    12. Review
    13. Communications
    1. You have free access to this content
      Cover Picture: Stereoselective Synthesis of Vinyl Triflones and Heteroaryl Triflones through Anionic O[RIGHTWARDS ARROW]Cvinyl and N[RIGHTWARDS ARROW]Cvinyl Trifluoromethanesulfonyl Migration Reactions (Angew. Chem. Int. Ed. 48/2013) (page 12455)

      Dr. Xiu-Hua Xu, Misaki Taniguchi, Xin Wang, Etsuko Tokunaga, Prof. Dr. Tomohiro Ozawa, Prof. Dr. Hideki Masuda and Prof. Dr. Norio Shibata

      Article first published online: 4 NOV 2013 | DOI: 10.1002/anie.201308947

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      Six transformations in one pot allow the stereoselective synthesis of various di- and trisubstituted vinyl triflones, and several heteroaryl triflones from gem-dibromovinyl substrates. In their Communication on page 12628 ff., N. Shibata et al. explore the key steps of this procedure. The cover picture shows a “Japanese-style painting” by Mami Shibata (a Tama Art University student), named “Kaze” (“breeze” in English). The six transformations in one pot proceed very smoothly, like birds in a breeze.

    2. You have free access to this content
      Inside Cover: Double-Decker-Type Dinuclear Nickel Catalyst for Olefin Polymerization: Efficient Incorporation of Functional Co-monomers (Angew. Chem. Int. Ed. 48/2013) (page 12456)

      Dr. Daisuke Takeuchi, Yuriko Chiba, Shigenaga Takano and Prof. Dr. Kohtaro Osakada

      Article first published online: 7 NOV 2013 | DOI: 10.1002/anie.201308948

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      A dinuclear nickel complex with a new double-decker structure, and its catalytic properties are described by D. Takeuchi, K. Osakada, et al. in their Communication on page 12536 ff. The complex promotes the copolymerization of ethylene with bifunctional monomers such as terminal dienes and unsaturated carboxylic esters. The close positioning of the nickel centers supported by the rigid macrocyclic ligand enhances the coordination of the bifunctional monomers and stabilize the growing polymer end.

    3. You have free access to this content
      Inside Back Cover: Identification of the HcgB Enzyme in [Fe]-Hydrogenase-Cofactor Biosynthesis (Angew. Chem. Int. Ed. 48/2013) (page 12745)

      Dr. Takashi Fujishiro, Dr. Haruka Tamura, Dr. Michael Schick, Jörg Kahnt, Dr. Xiulan Xie, Dr. Ulrich Ermler and Dr. Seigo Shima

      Article first published online: 12 NOV 2013 | DOI: 10.1002/anie.201308951

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      One reaction step of the biosynthesis of [Fe]-hydrogenase-cofactor is elucidated by S. Shima et al. in their Communication on page 12555 ff. A structural genomics approach, in combination with model reactions and thorough product analysis by X-ray crystallography of the protein–product complexes, revealed that HcgB is the enzyme that catalyzes guanylylpyridinol formation from a 2,4-dihydroxypyridine derivative and guanosine triphosphate.

    4. You have free access to this content
      Back Cover: S2 Fluorescence Dynamics of meso-Aryl-Substituted Subporphyrins (Angew. Chem. Int. Ed. 48/2013) (page 12746)

      Jooyoung Sung, Pyosang Kim, Shun Saga, Shin-ya Hayashi, Prof. Dr. Atsuhiro Osuka and Prof. Dr. Dongho Kim

      Article first published online: 18 NOV 2013 | DOI: 10.1002/anie.201309064

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      The S2 fluorescence and the photophysical behavior of the higher excited states of subporphyrins are described by A. Osuka, D. Kim, et al. in their Communication on page 12632 ff. The S2 fluorescence of subporphyrins had not been described to date. Similarly, the Big Dipper is recognized as an asterism of seven stars. However, the eighth star, Alcor, definitely exists, although its close proximity to the star Mizar renders it more difficult to resolve.

  2. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Essay
    11. Minireview
    12. Review
    13. Communications
    1. Graphical Abstract: Angew. Chem. Int. Ed. 48/2013 (pages 12459–12474)

      Article first published online: 18 NOV 2013 | DOI: 10.1002/anie.201390049

  3. News

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Essay
    11. Minireview
    12. Review
    13. Communications
  4. Author Profile

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Essay
    11. Minireview
    12. Review
    13. Communications
    1. Marina A. Petrukhina (page 12480)

      Article first published online: 5 JUL 2013 | DOI: 10.1002/anie.201304842

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      “My favorite saying is “yes, we can!” I can never resist travelling to new places …” This and more about Marina A. Petrukhina can be found on page 12480.

  5. News

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Essay
    11. Minireview
    12. Review
    13. Communications
  6. Obituary

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Essay
    11. Minireview
    12. Review
    13. Communications
    1. Manfred Schlosser (19342013) (page 12483)

      Frédéric Leroux

      Article first published online: 7 NOV 2013 | DOI: 10.1002/anie.201308231

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  7. Book Review

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Essay
    11. Minireview
    12. Review
    13. Communications
    1. Bioinspiration and Biomimicry in Chemistry. Reverse-Engineering Nature. Edited by Gerhard F. Swiegers. (page 12484)

      Zoe Schnepp

      Article first published online: 8 NOV 2013 | DOI: 10.1002/anie.201306735

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      John Wiley and Sons, Hoboken, 2012. 508 pp., hardcover, € 122.00.—ISBN 978-0470566671

  8. Highlights

    1. Top of page
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    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Essay
    11. Minireview
    12. Review
    13. Communications
    1. Cellular Transport

      Intracellular Transport Mechanisms: Nobel Prize for Medicine 2013 (pages 12486–12488)

      Jun.-Prof. Dr. Kirsten Bacia

      Article first published online: 8 NOV 2013 | DOI: 10.1002/anie.201308937

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      How are biomolecules transported between cellular compartments? James E. Rothman, Randy W. Schekman, and Thomas C. Südhof made seminal contributions to answering this question with their research into the molecular mechanism of intracellular vesicle transport. For their achievements, the researchers were awarded the Nobel Prize in Physiology or Medicine on October 7, 2013.

    2. Computational Chemistry

      Solving Chemical Problems with a Mixture of Quantum-Mechanical and Molecular Mechanics Calculations: Nobel Prize in Chemistry 2013 (pages 12489–12491)

      Dr. Gerrit Groenhof

      Article first published online: 7 NOV 2013 | DOI: 10.1002/anie.201309174

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      The significance of computer simulations in such varied fields as chemistry, biophysics, structural biology, and materials science is emphasized by the award of the Nobel Prize in Chemistry 2013 to three of the most important pioneers of computational chemistry. Computer simulations are widely used today to interpret experimental results, to test hypotheses, and as inspiration for experiments.

  9. Essay

    1. Top of page
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    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Essay
    11. Minireview
    12. Review
    13. Communications
    1. Homogenous Catalysis

      Oligomerization of Ethylene to α-Olefins: Discovery and Development of the Shell Higher Olefin Process (SHOP) (pages 12492–12496)

      Prof. Dr. Wilhelm Keim

      Article first published online: 15 OCT 2013 | DOI: 10.1002/anie.201305308

      Luck, talent, and hard work: Currently, over a million tons of α-olefins are manufactured per annum using the Shell Higher Olefin Process (SHOP). The discovery of the process was the result of correct model conceptions and lucky coincidence. W. Keim, one of the main participants in the development of SHOP, gives a personal account of the events.

  10. Minireview

    1. Top of page
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    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Essay
    11. Minireview
    12. Review
    13. Communications
    1. Nucleic Acid Modifications

      Artificial Genetic Sets Composed of Size-Expanded Base Pairs (pages 12498–12508)

      Dr. Malte Winnacker and Prof. Dr. Eric T. Kool

      Article first published online: 7 NOV 2013 | DOI: 10.1002/anie.201305267

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      Expanded horizons: Stretched nucleobases, which are larger than the bases of the natural Watson–Crick architecture, lead to the development of artificial genetic sets. These systems have properties that are useful for understanding fundamental biochemical questions as well as for the development of new biotechnological, biomedical, and nanostructural tools and methods.

  11. Review

    1. Top of page
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    4. News
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    7. Obituary
    8. Book Review
    9. Highlights
    10. Essay
    11. Minireview
    12. Review
    13. Communications
    1. Redox-Active Ligands

      Complexes with Nitrogen-Centered Radical Ligands: Classification, Spectroscopic Features, Reactivity, and Catalytic Applications (pages 12510–12529)

      Alma I. Olivos Suarez, Dr. Volodymyr Lyaskovskyy, Prof. Dr. Joost N. H. Reek, Dr. Ir. Jarl Ivar van der Vlugt and Prof. Dr. Bas de Bruin

      Article first published online: 8 NOV 2013 | DOI: 10.1002/anie.201301487

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      Radical character is found in many complexes with nitrogen ligands, as shown by studies of their electronic structure, spectroscopic features, and (catalytic) reactivity. The Review focuses on the reactivity of detectable aminyl ([M(.NR2)]), nitrene/imidyl ([M(.NR)]), and nitridyl radical complexes ([M(.N)]), and their application in the (catalytic) synthesis of nitrogen-containing organic molecules such as aziridines and amines.

  12. Communications

    1. Top of page
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    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Essay
    11. Minireview
    12. Review
    13. Communications
    1. Molecular Electronics

      Growth of Ultrathin Organic Semiconductor Microstripes with Thickness Control in the Monolayer Precision (pages 12530–12535)

      Dr. Liqiang Li, Dr. Peng Gao, Dr. Wenchong Wang, Prof. Klaus Müllen, Prof. Harald Fuchs and Prof. Lifeng Chi

      Article first published online: 31 OCT 2013 | DOI: 10.1002/anie.201306953

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      Organic semiconductors: Growth of ultrathin (<15 nm), continuous, and microstructured organic semiconductor (OSC) films at monolayer precision is important for organic electronics and a challenging task. Uniform monolayer to hexalayer (ca. 1.6–12 nm; see picture) dendritic OSC microstripes at monolayer precision are grown by a dip-coating process.

    2. Copolymerization

      Double-Decker-Type Dinuclear Nickel Catalyst for Olefin Polymerization: Efficient Incorporation of Functional Co-monomers (pages 12536–12540)

      Dr. Daisuke Takeuchi, Yuriko Chiba, Shigenaga Takano and Prof. Dr. Kohtaro Osakada

      Article first published online: 7 NOV 2013 | DOI: 10.1002/anie.201307741

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      A dinuclear Ni complex with a double-decker structure (see scheme) and a short Ni–Ni distance promotes the copolymerization of ethylene with functional monomers. Matching of the Ni–Ni distance with the co-monomer structure resulted in polymers containing a high density of the co-monomer unit.

    3. Lithium-Ion Batteries

      A Lithium-Rich Compound Li7Mn(BO3)3 Containing Mn2+ in Tetrahedral Coordination: A Cathode Candidate for Lithium-Ion Batteries (pages 12541–12544)

      Dr. Semih Afyon, Dr. Michael Wörle and Prof. Dr. Reinhard Nesper

      Article first published online: 14 OCT 2013 | DOI: 10.1002/anie.201307655

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      Filled to capacity: Li7Mn(BO3)3 is lithium-rich and fulfills the prerequisites for a high-capacity cathode for Li-ion batteries. It contains a framework of MnO4 tetrahedra (pink) and BO33− ions (B green, O red, Li black). By employing a nano-composite to enhance electronic conductivity, a first charge capacity of 280 mAh g−1, and a specific energy of 1135 W h kg−1 are obtained within 4.7–1.7 V at a rate of 10 mA g−1.

    4. Contact Electrification

      Water–Solid Surface Contact Electrification and its Use for Harvesting Liquid-Wave Energy (pages 12545–12549)

      Dr. Zong-Hong Lin, Dr. Gang Cheng, Long Lin, Dr. Sangmin Lee and Prof. Zhong Lin Wang

      Article first published online: 7 OCT 2013 | DOI: 10.1002/anie.201307249

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      Electrical wave mechanics: A newly designed triboelectric nanogenerator is based on the contact electrification between a patterned polydimethylsiloxane pyramid array and water. Cost-effective and simple, the prototype triboelectric nanogenerator shows the potential to harvest energy from liquid waves and serve as chemical and temperature sensors.

    5. Self-Assembly

      A Supramolecular Gel from a Quadruple Zwitterion that Responds to Both Acid and Base (pages 12550–12554)

      Dr. Yosuke Hisamatsu, Dr. Supratim Banerjee, M. B. Avinash, Prof. Dr.  T. Govindaraju and Prof. Dr. Carsten Schmuck

      Article first published online: 2 OCT 2013 | DOI: 10.1002/anie.201306986

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      Four arms: A quadruple zwitterion based on a pentaerythritol core forms thermoreversible gels in DMSO driven by the formation of ion-paired dimers between the zwitterionic units. Furthermore, it exhibits reversible gel–sol transitions in response to both acid and base.

    6. Cofactor Biosynthesis

      Identification of the HcgB Enzyme in [Fe]-Hydrogenase-Cofactor Biosynthesis (pages 12555–12558)

      Dr. Takashi Fujishiro, Dr. Haruka Tamura, Dr. Michael Schick, Jörg Kahnt, Dr. Xiulan Xie, Dr. Ulrich Ermler and Dr. Seigo Shima

      Article first published online: 7 NOV 2013 | DOI: 10.1002/anie.201306745

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      [Fe]-Hydrogenase requires the iron guanylylpyridinol (FeGP) cofactor for activity. The function of HcgB, an enzyme in the biosynthesis of the FeGP cofactor, was predicted by structural genomics and confirmed by model reactions and various analytical methods: HcgB catalyzes the terminal guanylyltransferase reaction for the formation of guanylylpyridinol. GMP=guanosine monophosphate.

    7. Synthetic Methods

      You have full text access to this OnlineOpen article
      Selective Reduction of Barbituric Acids Using SmI2/H2O: Synthesis, Reactivity, and Structural Analysis of Tetrahedral Adducts (pages 12559–12563)

      Dr. Michal Szostak, Brice Sautier, Malcolm Spain, Maike Behlendorf and Prof. Dr. David J. Procter

      Article first published online: 9 OCT 2013 | DOI: 10.1002/anie.201306484

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      Making a mark: Since the 1864 landmark discovery by Adolf von Baeyer, barbituric acids have played a prominent role in organic synthesis. Herein, the first chemoselective monoreduction of barbituric acids to the corresponding hemiaminals is described. The method delivers mono- and bicyclic hemiaminal products by a general single-electron-transfer polarity reversal mechanism.

    8. Helical Structures

      Structural Characterization of α/β-Peptides having Alternating Residues: X-ray Structures of the 11/9-Helix from Crystals of Racemic Mixtures (pages 12564–12567)

      Mihye Lee, Jihyun Shim, Philjae Kang, Dr. Ilia A. Guzei and Prof. Dr. Soo Hyuk Choi

      Article first published online: 2 OCT 2013 | DOI: 10.1002/anie.201306404

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      Twisted (crystal)sisters: The structures of the α/β-peptide 11/9-helix were determined by single-crystal X-ray crystallography. The racemic compounds adopt centrosymmetric crystal packing, and display fully folded 11/9-helical conformations. The helical parameters of the 11/9-helix are analogous to those of the 310-helix, despite different hydrogen-bonding types.

    9. Pigment Discoloration

      Formation of Metallic Mercury During Photodegradation/Photodarkening of α-HgS: Electrochemical Evidence (pages 12568–12571)

      Willemien Anaf, Prof. Dr. Koen Janssens and Prof. Dr. Karolien De Wael

      Article first published online: 2 OCT 2013 | DOI: 10.1002/anie.201303977

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      The red pigment α-HgS tends to blacken in the presence of light and chloride ions. Hypotheses exist for the decomposition and discoloration, including formation of β-HgS (black) or of metallic mercury, but these have not been detected on naturally or synthetically degraded HgS paint. Electrochemical experiments now demonstrate the formation of metallic mercury in the presence of light and chloride ions.

    10. Imaging Agents

      PEGylation and Zwitterionization: Pros and Cons in the Renal Clearance and Tumor Targeting of Near-IR-Emitting Gold Nanoparticles (pages 12572–12576)

      Dr. Jinbin Liu, Dr. Mengxiao Yu, Xuhui Ning, Dr. Chen Zhou, Dr. Shengyang Yang and Prof. Dr. Jie Zheng

      Article first published online: 9 OCT 2013 | DOI: 10.1002/anie.201304465

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      Got it PEGged: PEGylation and zwitterionization have distinct effects on the pharmacokinetic and tumor-targeting properties of luminescent gold nanoparticles (AuNPs), although both strategies lead to effective renal clearance. High tumor-targeting efficiency and specificity were obtained with PEGylated AuNPs, whereas rapid tumor detection was more readily achieved with zwitterionic AuNPs. HD=hydrodynamic diameter, GS=glutathione.

    11. Electrocatalysis

      Biomimetic Synthesis of an Ultrathin Platinum Nanowire Network with a High Twin Density for Enhanced Electrocatalytic Activity and Durability (pages 12577–12581)

      Lingyan Ruan, Enbo Zhu, Yu Chen, Zhaoyang Lin, Xiaoqing Huang, Prof. Xiangfeng Duan and Prof. Yu Huang

      Article first published online: 2 OCT 2013 | DOI: 10.1002/anie.201304658

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      Structure-enhanced catalytic activity: An ultrathin platinum multiple-twinned nanowire network is shown to be an efficient electrocatalyst (see picture). This material has a higher electrochemical surface area and exhibits a much improved activity toward both the oxygen reduction reaction and the methanol oxidation reaction relative to commercial Pt/C catalysts.

    12. Liquid Coordination Complexes

      Liquid Coordination Complexes Formed by the Heterolytic Cleavage of Metal Halides (pages 12582–12586)

      Dr. Fergal Coleman, Dr. Geetha Srinivasan and Dr. Małgorzata Swadźba-Kwaśny

      Article first published online: 11 OCT 2013 | DOI: 10.1002/anie.201306267

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      Confused complexes: Reaction of a range of donor molecules with AlCl3 or GaCl3, gives mobile liquids with very high metal contents. They contain statistically distributed mixtures of anionic, cationic, and neutral complexes in equilibrium. These liquid coordination complexes (LCCs), have high conductivity, tunable Lewis acidity, and low vapor pressure.

    13. Ligand–Protein Complexes

      Dissociation Kinetics of a Binary Complex in Solution by Protein Displacement (pages 12587–12591)

      Dr. Helene Launay, Dr. Benjamin Parent, Dr. Adeline Page, Dr. Xavier Hanoulle and Dr. Guy Lippens

      Article first published online: 7 OCT 2013 | DOI: 10.1002/anie.201306253

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      Kinetics determined by NMR: Whereas most measurements of kinetic parameters of a ligand–protein complex use displacement of the ligand, protein displacement can give accurate off-rates in solution (see picture). Analytical and simulation results are given for the apparent off-rate obtained by protein displacement.

    14. Bioconjugation

      Rapid, Stable, Chemoselective Labeling of Thiols with Julia–Kocieński-like Reagents: A Serum-Stable Alternative to Maleimide-Based Protein Conjugation (pages 12592–12596)

      Dr. Narihiro Toda, Dr. Shigehiro Asano and Prof. Dr. Carlos F. Barbas III

      Article first published online: 2 OCT 2013 | DOI: 10.1002/anie.201306241

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      Exquisite chemoselectivity for cysteine has been found for methylsulfonylphenyloxadiazole compounds under various buffer conditions. Furthermore, the resulting protein conjugates have superior stability to cysteine–maleimide conjugates in human plasma (HSA=human serum albumin, MBP-C-HA=maltose-binding protein). This new thiol-click reaction offers a new approach to generate stable protein conjugates and Pegylated proteins.

    15. G-Quadruplexes

      Real-Time Optical Detection of Stabilized Artificial G-Quadruplexes Under Confined Conditions (pages 12597–12601)

      Bogdan George Rusu, Dr. Frédérique Cunin and Dr. Mihail Barboiu

      Article first published online: 2 OCT 2013 | DOI: 10.1002/anie.201306230

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      The color of self-assembly: Porous silicon (pSi) can be used as a scaffolding matrix to stabilize G-quadruplexes under confined conditions. When G-quadruplexes were infused into the pores, a change in the film color was observed, so that confinement and stabilization of the G-quadruplexes can be easily observed.

    16. Rotational Dynamics

      Modulating the Rotation of a Molecular Rotor through Hydrogen-Bonding Interactions between the Rotator and Stator (pages 12602–12605)

      Qian-Chong Zhang, Fang-Ting Wu, Hui-Min Hao, Hang Xu, Hai-Xia Zhao, Prof. Dr. La-Sheng Long, Prof. Rong-Bin Huang and Prof. Dr. Lan-Sun Zheng

      Article first published online: 2 OCT 2013 | DOI: 10.1002/anie.201306193

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      Two molecular rotors were synthesized (see picture). An investigation of the rotator rotation based on the imaginary parts of the complex dielectric constant (ε′′) for each molecular rotor at various frequencies and temperatures revealed that the rotation of the mono-component molecular rotor could be modulated through hydrogen-bonding interactions between the rotator and the stator.

    17. Mesoporous Materials

      Crystallization of Tungsten Trioxide Having Small Mesopores: Highly Efficient Photoanode for Visible-Light-Driven Water Oxidation (pages 12606–12609)

      Dr. Debraj Chandra, Prof. Kenji Saito, Prof. Tatsuto Yui and Prof. Masayuki Yagi

      Article first published online: 7 OCT 2013 | DOI: 10.1002/anie.201306004

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      Small mesopores are more efficient: A mesoprous oxide semiconductor (tungsten trioxide) having small mesopores was crystallized at high temperature (550 °C) by a simple one-step procedure. The highly crystalline mesoporous WO3 has an extremely high surface area which improves the visible-light-driven photoelectrochemical performance of water oxidation (see picture) relative to WO3 having interparticle mesopores.

    18. Fullerides

      Counterintuitive Anisotropy of Electron Transport Properties in KC60(THF)5⋅2 THF Fulleride (pages 12610–12614)

      Dr. A. Kromer, Dr. U. Wedig, Prof. E. Roduner, Prof. M. Jansen and Dr. Konstantin Yu. Amsharov

      Article first published online: 2 OCT 2013 | DOI: 10.1002/anie.201305808

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      Spin and charge transport: The electronic and structural properties obtained from KC60(THF)5⋅2 THF single crystals are reported (see picture). An important finding is the presence of one-dimensional electric conductivity and the observation of counterintuitive anisotropy for electron transport.

    19. Vapor Sensing

      Three-Dimensional Solvent-Vapor Map Generated by Supramolecular Metal-Complex Entrapment (pages 12615–12618)

      Avishek Saha, Zack Panos, Ty Hanna, Kewei Huang, Mayra Hernández-Rivera and Prof. Angel A. Martí

      Article first published online: 2 OCT 2013 | DOI: 10.1002/anie.201305762

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      Whodunit? [Re(phen)(CO)3Cl] (phen=1,10-phenanthroline) has been entrapped within a faujasite zeolite. For this material, changes in the photoluminescence intensity, wavelength, and lifetime are observed upon exposure to solvent vapors. Every solvent vapor produces a unique combination of photophysical parameters that can be used as a fingerprint of the vapor.

    20. Asymmetric Catalysis

      Organocatalytic Asymmetric Conjugate Addition of Aldehydes to Nitroolefins: Identification of Catalytic Intermediates and the Stereoselectivity-Determining Step by ESI-MS (pages 12619–12623)

      Florian Bächle, Dr. Jörg Duschmalé, Dr. Christian Ebner, Prof. Dr. Andreas Pfaltz and Prof. Dr. Helma Wennemers

      Article first published online: 2 OCT 2013 | DOI: 10.1002/anie.201305338

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      Looking back: The asymmetric organocatalytic 1,4-addition of aldehydes to nitroolefins was studied by ESI-MS. Analysis of the back reaction starting from quasienantiomeric mass-labeled 1,4-adducts (see scheme) provided conclusive evidence for an enamine rather than an enol mechanism, and allowed identification of the enantioselectivity-determining step.

    21. Synthetic Methods

      3-Methyl-4-oxa-5-azahomoadamantane: Alkoxyamine-Type Organocatalyst for Alcohol Oxidation (pages 12624–12627)

      Yusuke Sasano, Keiichi Murakami, Tomohiro Nishiyama, Dr. Eunsang Kwon and Prof. Dr. Yoshiharu Iwabuchi

      Article first published online: 11 OCT 2013 | DOI: 10.1002/anie.201307144

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      Strong, silent type: A novel alkoxyamine-type organocatalyst has been discovered for alcohol oxidation (see scheme). The alkoxyamine exhibits a high catalytic activity for the oxidation of alcohols to afford the corresponding carbonyl compounds in high yield by oxidative transformation into an oxoammonium ion, which is proposed to serve as an active species.

    22. Stereoselective Synthesis of Vinyl Triflones and Heteroaryl Triflones through Anionic O[RIGHTWARDS ARROW]Cvinyl and N[RIGHTWARDS ARROW]Cvinyl Trifluoromethanesulfonyl Migration Reactions (pages 12628–12631)

      Dr. Xiu-Hua Xu, Misaki Taniguchi, Xin Wang, Etsuko Tokunaga, Prof. Dr. Tomohiro Ozawa, Prof. Dr. Hideki Masuda and Prof. Dr. Norio Shibata

      Article first published online: 15 OCT 2013 | DOI: 10.1002/anie.201307535

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      Six transformations, one pot: Various di- and trisubstituted vinyl triflones, as well as several heteroaryl triflones, were stereoselectively synthesized from easily accessible gem-dibromovinyl substrates (see scheme, Boc=tert-butoxycarbonyl). The highlights of this synthetic method lie in the remote O[RIGHTWARDS ARROW]Cvinyl or N[RIGHTWARDS ARROW]Cvinyl triflyl migrations and the one-pot, three-step protocol.

    23. Subporphyrins

      S2 Fluorescence Dynamics of meso-Aryl-Substituted Subporphyrins (pages 12632–12635)

      Jooyoung Sung, Pyosang Kim, Shun Saga, Shin-ya Hayashi, Prof. Dr. Atsuhiro Osuka and Prof. Dr. Dongho Kim

      Article first published online: 25 OCT 2013 | DOI: 10.1002/anie.201307566

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      S2 Fluorescence: Subporphyrins are intriguing compounds, but the behavior of their higher excited states has not been studied thus far. The S2 fluorescence of subporphyrins has now been investigated; internal conversion from the S2 to the S1 state was revealed to occur within approximately 300 fs. The two transition dipole moments of the degenerate S2 states are orthogonally oriented despite the C3 symmetry of the subporphyrin.

    24. Photochemistry

      Concerted Two-Electron Transfer and High Selectivity of TiO2 in Photocatalyzed Deoxygenation of Epoxides (pages 12636–12640)

      Dr. Yue Li, Prof. Hongwei Ji, Prof. Chuncheng Chen, Prof. Wanhong Ma and Prof. Jincai Zhao

      Article first published online: 7 OCT 2013 | DOI: 10.1002/anie.201307374

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      No two ways about it: In the photocatalytic deoxygenation of epoxides, the TiO2 particle concertedly transfers two stored electrons to generate a carbanion intermediate, which dissociates to the alkene product. This pathway ensures the higher alkene and stereoselectivity of the photocatalytic deoxygenation than those involving a single-electron transfer.

    25. Asymmetric Catalysis

      Enantioselective Copper-Catalyzed [3+3] Cycloaddition of Azomethine Ylides with Azomethine Imines (pages 12641–12645)

      Prof. Dr. Hongchao Guo, Honglei Liu, Fu-Lin Zhu, Dr. Risong Na, Hui Jiang, Yang Wu, Lei Zhang, Zhen Li, Hao Yu, Bo Wang, Dr. Yumei Xiao, Prof. Dr. Xiang-Ping Hu and Prof. Dr. Min Wang

      Article first published online: 2 OCT 2013 | DOI: 10.1002/anie.201307317

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      The more dipoles, the merrier: An asymmetric [3+3] cycloaddition of azomethine ylides derived from imines 1 with azomethine imines 2 in the presence of a chiral ferrocenylphosphine–copper catalyst afforded highly functionalized heterocyclic products 3 in high yield with excellent enantio- and diastereoselectivity (see scheme; DBU=1,8-diazabicyclo[5.4.0]undec-7-ene). The 1,3-dipolar reaction partners can be readily prepared from aldehydes.

    26. Uranium Siloxides

      Controlled Thermolysis of Uranium (Alkoxy)siloxy Complexes: A Route to Polymetallic Complexes of Low-Valent Uranium (pages 12646–12650)

      Clément Camp, Dr. Christos E. Kefalidis, Dr. Jacques Pécaut, Prof. Laurent Maron and Dr. Marinella Mazzanti

      Article first published online: 9 OCT 2013 | DOI: 10.1002/anie.201307291

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      Decomposition into higher species: Intramolecular UIII-mediated homolytic C[BOND]O bond cleavage in UIII (alkoxy)siloxy complexes at low temperature and subsequent reduction with KC8 led to unprecedented polymetallic complexes containing siloxy, silanediolate, and silanetriolate ligands (see example: U green, Si yellow, K blue, O red). Such compounds may be useful precursors to uranium ceramics relevant for catalysis and the storage of spent nuclear fuel.

    27. Synthetic Methods

      Bis(amino)cyclopropenylidenes as Organocatalysts for Acyl Anion and Extended Umpolung Reactions (pages 12651–12654)

      Myron M. D. Wilde and Prof. Michel Gravel

      Article first published online: 2 OCT 2013 | DOI: 10.1002/anie.201307167

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      Back to BACs: In the pursuit of novel carbene organocatalysts, bis(amino)cyclopropenylidenes (BACs) were explored as alternatives to N-heterocyclic carbenes. They were effective in catalyzing the Stetter reaction, and displayed unique advantages over the commonly used thiazolylidenes and triazolylidenes. They also mediated extended umpolung reactions of enals. In addition, chiral analogues can be accessed readily for applications in enantioselective catalysis.

      Corrected by:

      Corrigendum: Corrigendum: Bis(amino)cyclopropenylidenes as Organocatalysts for Acyl Anion and Extended Umpolung Reactions

      Vol. 53, Issue 4, 912, Article first published online: 21 JAN 2014

    28. Enantioselective Functionalization of Radical Intermediates in Redox Catalysis: Copper-Catalyzed Asymmetric Oxytrifluoromethylation of Alkenes (pages 12655–12658)

      Rong Zhu and Prof. Dr. Stephen L. Buchwald

      Article first published online: 16 OCT 2013 | DOI: 10.1002/anie.201307790

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      Something radical: An efficient enantioselective oxytrifluoromethylation of alkenes has been developed using a copper catalyst system. Mechanistic studies are consistent with a metal-catalyzed redox radical addition mechanism in which a C[BOND]O bond is formed by the copper-mediated enantioselective trapping of a prochiral alkyl radical intermediate derived from the initial trifluoromethyl radical addition.

    29. Hydrogen Storage

      Immobilization of Aluminum Borohydride Hexammoniate in a Nanoporous Polymer Stabilizer for Enhanced Chemical Hydrogen Storage (pages 12659–12663)

      Ziwei Tang, Yingbin Tan, Xiaowei Chen, Prof. Liuzhang Ouyang, Prof. Min Zhu, Prof. Dalin Sun and Prof. Xuebin Yu

      Article first published online: 2 OCT 2013 | DOI: 10.1002/anie.201306083

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      Caught in a trap: The well-distributed Al(BH4)3⋅6 NH3/PSDB (PSDB=poly(styrene-co-divinylbenzene)) nanocomposite was synthesized by the stabilization of volatile Al(BH4)3 within a porous polymer and subsequent treatment with ammonia. This material showed a hydrogen-storage performance that was significantly improved over that of its bulk counterpart. Partial regeneration using hydrazine in ammonia is also described.

    30. Asymmetric Catalysis

      Highly Enantioselective Dearomatizing Formal [3+3] Cycloaddition Reactions of N-Acyliminopyridinium Ylides with Electrophilic Enol Carbene Intermediates (pages 12664–12668)

      Dr. Xinfang Xu, Dr. Peter Y. Zavalij and Prof. Michael P. Doyle

      Article first published online: 2 OCT 2013 | DOI: 10.1002/anie.201305539

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      Extrusion of dinitrogen from enol diazoacetates with a RhII catalyst generates metal enol carbenes. Subsequent vinylogous addition of these to N-acyliminopyridinium ylides results in an effective formal [3+3] cycloaddition to give highly substituted 1,2,3,6-tetrahydropyridazines in up to 98 % ee and high yield.

    31. Heterocycle Synthesis

      Palladium-Catalyzed Synthesis of Benzofurans and Coumarins from Phenols and Olefins (pages 12669–12673)

      Dr. Upendra Sharma, Togati Naveen, Arun Maji, Srimanta Manna and Prof. Debabrata Maiti

      Article first published online: 11 OCT 2013 | DOI: 10.1002/anie.201305326

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      Triple C[BOND]H functionalization: Palladium-catalyzed synthesis of benzofurans and coumarins by reacting phenols and unactivated olefins is described. The reaction comprises sequential C[BOND]H functionalization and shows diverse functional group compatibility. Preliminary mechanistic studies shed light into the possible mechanisms.

    32. Reductive Bond Cleavage

      Selective Reductive Cleavage of Inert Aryl C[BOND]O Bonds by an Iron Catalyst (pages 12674–12678)

      Dr. Yunlai Ren, Mengjie Yan, Jianji Wang, Z. Conrad Zhang and Kaisheng Yao

      Article first published online: 7 OCT 2013 | DOI: 10.1002/anie.201305342

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      Breaking point: An effective reductive cleavage of inert aryl C[BOND]O bonds with an inexpensive iron catalyst has been developed. During this process, the reduction of the arene rings was not observed. This catalytic system also enabled the selective cleavage of the β-O-4 linkage of lignin model compounds under an atmosphere of hydrogen, thus offering an opportunity for the depolymerization of lignin.

    33. Modular Synthesis

      You have full text access to this OnlineOpen article
      Palladium-Catalyzed Three-Component Diaryl Sulfone Synthesis Exploiting the Sulfur Dioxide Surrogate DABSO (pages 12679–12683)

      Edward J. Emmett, Dr. Barry R. Hayter and Prof. Michael C. Willis

      Article first published online: 2 OCT 2013 | DOI: 10.1002/anie.201305369

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      SO(2) efficient: A three-component palladium-catalyzed coupling of aryl lithium compounds; sulfur dioxide (provided by the easy-to-handle solid surrogate, DABSO); and aryl, heteroaryl, and alkenyl (pseudo)halides yields a diverse library of sulfones. An electron-poor XantPhos-type ligand suppresses aryl–aryl exchange and is key to obtaining high yields.

    34. Free-Radical Scavengers

      Atypical Structural and π-Electron Features of a Melanin Polymer That Lead to Superior Free-Radical-Scavenging Properties (pages 12684–12687)

      Dr. Lucia Panzella, Dr. Gennaro Gentile, Dr. Gerardino D'Errico, Dr. Nicola F. Della Vecchia, Dr. Maria E. Errico, Prof. Dr. Alessandra Napolitano, Prof. Dr. Cosimo Carfagna and Prof. Dr. Marco d'Ischia

      Article first published online: 7 OCT 2013 | DOI: 10.1002/anie.201305747

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      The black we wear: Why nature selected 5,6-dihydroxyindole-2-carboxylic acid (DHICA) to synthesize (photo)protective eumelanin pigments is an enigma. Synthetic DHICA eumelanin has now been shown to be a highly efficient free-radical scavenger in the solid state, which is due to a conformationally interrupted π-electron network associated with atypical optical, paramagnetic, and aggregation properties.

    35. Mechanochemical Activation

      An Orders-of-Magnitude Increase in the Rate of the Solid-Catalyzed CO Oxidation by In Situ Ball Milling (pages 12688–12691)

      Sarah Immohr, Dr. Michael Felderhoff, Dr. Claudia Weidenthaler and Prof. Dr. Ferdi Schüth

      Article first published online: 23 SEP 2013 | DOI: 10.1002/anie.201305992

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      Shaken, not stirred: CO oxidation was carried out continuously in a shaker ball mill. During milling, the reaction rate increases dramatically, but drops rapidly to zero when the mill is stopped. Compared to a conventional experiment in a plug-flow reactor, the rate of a ball-mill reaction catalyzed by Cr2O3 is three orders of magnitude higher at room temperature and one order of magnitude higher at 100°C.

    36. Water Splitting

      Hematite-Based Water Splitting with Low Turn-On Voltages (pages 12692–12695)

      Chun Du, Dr. Xiaogang Yang, Dr. Matthew T. Mayer, Henry Hoyt, Jin Xie, Dr. Gregory McMahon, Gregory Bischoping and Prof. Dr. Dunwei Wang

      Article first published online: 7 OCT 2013 | DOI: 10.1002/anie.201306263

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      Power up: The photoelectrochemical performance of hematite in a water-splitting device was improved significantly through surface modification with amorphous NiFeOx (see graph showing the large cathodic shift observed; FTO=fluorine-doped tin oxide). The measured photovoltage increased from 0.24 to 0.61 V, which yielded a record-low turn-on potential of 0.62 V (versus the reversible hydrogen electrode, RHE).

    37. Photochemistry

      A Visible-Light-Mediated Synthesis of Carbazoles (pages 12696–12700)

      Augusto C. Hernandez-Perez and Prof. Dr. Shawn K. Collins

      Article first published online: 7 OCT 2013 | DOI: 10.1002/anie.201306920

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      The photosynthetic preparation of N-aryl- and N-alkyl-bearing carbazoles utilizes continuous flow, visible light, and an in situ formed Cu-based sensitizer (see picture). The method is mild and efficient, and allows the straightforward synthesis of a variety of carbazoles with different substituents, heterocycles, and complex carbon architectures.

    38. Asymmetric Catalysis

      Enantioselective Copper-Catalyzed Conjugate Addition of Trimethylaluminum to β,γ-Unsaturated α-Ketoamides: Efficient Access to γ-Methyl-Substituted Carbonyl Compounds (pages 12701–12704)

      Dr. Sylvie Goncalves-Contal, Dr. Ludovic Gremaud and Prof. Alexandre Alexakis

      Article first published online: 11 OCT 2013 | DOI: 10.1002/anie.201306541

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      Picture perfect: By using the reagent trimethylaluminium and β,γ-unsaturated α-ketoamides, 1,4-adducts were obtained with perfect 1,4-regioselectivity and good to excellent yields and ee values. The potential synthetic utility of the methodology was highlighted by preparation of γ-methyl-substituted carbonyls, key synthons to many natural products. binap=2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, TC=thiophene carboxylate.

    39. Hydroamination

      Diversity-Oriented Synthesis of Hydrazine-Derived Compounds from Amino Isocyanates Generated In Situ (pages 12705–12708)

      Christian Clavette, Jean-François Vincent Rocan and Prof. Dr. André M. Beauchemin

      Article first published online: 7 OCT 2013 | DOI: 10.1002/anie.201306379

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      Behind the mask: Nitrogen-substituted isocyanates are rare and their synthetic potential is virtually untapped. Simple masked precursors can form amphoteric amino isocyanate intermediates in situ, and allows the synthesis of complex hydrazine derivatives upon addition with amines. This reactivity was used in a cascade substitution/hydroamination sequence, and in the assembly of azadipeptide analogues.

    40. Nanocrystal Sensors

      Polyhedral Au–Pd Core–Shell Nanocrystals as Highly Spectrally Responsive and Reusable Hydrogen Sensors in Aqueous Solution (pages 12709–12713)

      Chun-Ya Chiu and Prof. Michael H. Huang

      Article first published online: 7 OCT 2013 | DOI: 10.1002/anie.201306363

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      Absorption signals absorption: The surface plasmon resonance absorption band of tetrahexahedral, octahedral, and cubic Au–Pd core–shell nanocrystals with gold nanocrystal cores was strongly red shifted upon hydrogen absorption into the Pd shell. This reversible spectral shift makes the nanocrystals promising recyclable hydrogen-gas sensors. Hydrogen absorption could even be detected visually with smaller core–shell octahedra (see picture).

    41. Organocatalysis

      Catalytic Enantioselective Michael Addition of α-Aryl-α-Isocyanoacetates to Vinyl Selenone: Synthesis of α,α-Disubstituted α-Amino Acids and (+)- and (−)-Trigonoliimine A (pages 12714–12718)

      Thomas Buyck, Dr. Qian Wang and Prof. Dr. Jieping Zhu

      Article first published online: 11 OCT 2013 | DOI: 10.1002/anie.201306663

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      Be like Mike: The title reaction in the presence of the catalyst 1 afforded Michael adducts in excellent yields and enantioselectivities. The adducts were readily converted into α,α′-disubstituted α-amino acids. The enantioselective total synthesis of both (+)- and (−)-trigonoliimine A was accomplished using one of the Michael adducts derived from this methodology. M.S.=molecular sieves.

    42. Cross-Coupling

      Copper(I)-Catalyzed Alkylation of Aryl- and Alkenylsilanes Activated by Intramolecular Coordination of an Alkoxide (pages 12719–12722)

      Dr. Akira Tsubouchi, Daisuke Muramatsu and Prof. Dr. Takeshi Takeda

      Article first published online: 9 OCT 2013 | DOI: 10.1002/anie.201306882

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      Let's coordinate: Copper(I)-catalyzed cross-coupling of alkenyl- and arylsilanes with primary alkyl iodides as well as allylic and benzylic halides as C(sp3)[BOND]X electrophilic coupling partners has been realized by intramolecular activation through alkoxide coordination. This alkylation tolerates a range of functional groups including a free hydroxy group. IPr=1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene.

    43. Ammonia Synthesis

      The Haber–Bosch Process Revisited: On the Real Structure and Stability of “Ammonia Iron” under Working Conditions (pages 12723–12726)

      Timur Kandemir, Dr. Manfred E. Schuster, Dr. Anatoliy Senyshyn, Dr. Malte Behrens and Prof. Dr. Robert Schlögl

      Article first published online: 9 OCT 2013 | DOI: 10.1002/anie.201305812

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      In situ neutron diffraction was used to study the structural properties of an industrial ammonia synthesis catalyst under working conditions similar to those of the Haber–Bosch process. Despite favorable thermodynamics, no indications of reversible bulk nitridation of the iron catalyst was observed in a self-generated ammonia concentration of 12 vol % at 425 °C and 75 bar after 88 h on stream.

    44. Heterocycle Synthesis

      Metal-Free Oxidative Cyclization of Alkynyl Aryl Ethers to Benzofuranones (pages 12727–12731)

      Dipl.-Chem. Katharina Graf, Carmen L. Rühl, Dr. Matthias Rudolph, Dr. Frank Rominger and Prof. Dr.  A. Stephen K. Hashmi

      Article first published online: 7 OCT 2013 | DOI: 10.1002/anie.201304813

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      Readily available phenols can be converted into substituted aryl alkynyl ethers, which react with an N-oxide as an oxidant and catalytic amounts of a Brønsted acid to provide benzofuranones. If non-terminal alkynyl ethers are applied, a 1,2-hydride shift takes place and phenyl acrylates are obtained. Thus activated alkynes can serve as α-oxy carbene precursors even in the absence of a metal catalyst.

    45. Polyinterhalides

      Iodine–Iodine Bonding makes Tetra(diiodine)chloride, [Cl(I2)4], Planar (pages 12732–12735)

      Dr. Christine Walbaum, M. Sc. Mark Richter, Dipl.-Chem. Ulf Sachs, Dr. Ingo Pantenburg, Prof. Dr. Sebastian Riedel, Prof. Dr. Anja-Verena Mudring and Prof. Dr. Gerd Meyer

      Article first published online: 2 OCT 2013 | DOI: 10.1002/anie.201305412

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      All square: The polyinterhalide [Cl(I2)4] is square-planar in the crystal structure of [(H5O2)(I2b15c5)2][Cl(I2)4] (I2b15c5=diiodobenzo-15-crown-5), although it would be tetrahedral in the gas phase. Along with other effects, such as electrostatic attractions between the cationic and planar anionic layers, iodine–iodine bonding with σ-hole interactions plays a considerable role is stabilizing the square-planar configuration.

      Corrected by:

      Corrigendum: Corrigendum: Iodine–Iodine Bonding makes Tetra(diiodine)chloride, [Cl(I2)4]−, Planar

      Vol. 53, Issue 21, 5233, Article first published online: 14 MAY 2014

    46. β-Peptides

      Alternating Asymmetric Self-Induction in Functionalized Pyrrolidine Oligomers (pages 12736–12740)

      Prof. Dr. Konstantin V. Kudryavtsev, Dipl.-Chem. Polina M. Ivantcova, Dr. Andrei V. Churakov, Steffen Wiedmann, Prof. Dr. Burkhard Luy, Dr. Claudia Muhle-Goll, Prof. Dr. Nikolay S. Zefirov and Prof. Dr. Stefan Bräse

      Article first published online: 10 OCT 2013 | DOI: 10.1002/anie.201302862

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      Rainbow of pyrrolidines: Red, orange, yellow, green, blue (indigo, violet).

    47. Solid-State NMR Spectroscopy

      The Conformation of the Prion Domain of Sup35 p in Isolation and in the Full-Length Protein (pages 12741–12744)

      Nina Luckgei, Dr. Anne K. Schütz, Dr. Luc Bousset, Dr. Birgit Habenstein, Yannick Sourigues, Dr. Carole Gardiennet, Prof. Dr. Beat H. Meier, Dr. Ronald Melki and Dr. Anja Böckmann

      Article first published online: 9 OCT 2013 | DOI: 10.1002/anie.201304699

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      The whole is not the sum of the parts: Fibrils form both from the full-length Sup35 prion protein and also from its isolated NM domain. A conformation analysis of both shows that Sup35NM and fragments thereof, which are often used as convenient models for prion fibril assembly, have a very different conformation of the prion domains.

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