Angewandte Chemie International Edition

Cover image for Vol. 54 Issue 37

September 7, 2015

Volume 54, Issue 37

Pages 10683–10984

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. Cover Picture: Template Synthesis of Linear-Chain Nanodiamonds Inside Carbon Nanotubes from Bridgehead-Halogenated Diamantane Precursors (Angew. Chem. Int. Ed. 37/2015) (page 10683)

      Yusuke Nakanishi, Dr. Haruka Omachi, Dr. Natalie A. Fokina, Prof. Dr. Peter R. Schreiner, Prof. Dr. Ryo Kitaura, Dr. Jeremy E. P. Dahl, Prof. Dr. Robert M. K. Carlson and Prof. Dr. Hisanori Shinohara

      Article first published online: 13 AUG 2015 | DOI: 10.1002/anie.201506980

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      Diamantane molecules form perfect linear-chain nanowires inside double-walled carbon nanotubes. In their Communication on page 10802 ff., H. Shinohara and co-workers describe how these nanowires are synthesized in a template reaction of dibrominated diamantane precursors in the hollow cavities of the carbon nanotubes. Under high vacuum and in the presence of iron nanocatalyst particles, the dehalogenated radical intermediates spontaneously form linear polymer chains within the nanotubes.

    2. Inside Cover: Vinylation of Unprotected Phenols Using a Biocatalytic System (Angew. Chem. Int. Ed. 37/2015) (page 10684)

      Dr. Eduardo Busto, Dr. Robert C. Simon and Prof. Dr. Wolfgang Kroutil

      Article first published online: 7 AUG 2015 | DOI: 10.1002/anie.201506939

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      Sliding down the enzymatic cascade Unprotected phenols were selectively para-vinylated using pyruvate as the reagent by W. Kroutil, E. Busto, and Robert C. Simon in their Communication on page 10899 ff. The cover illustrates the overall transformation starting from a substituted phenol, which passes the three involved enzymes on its way down, leading to the expulsion of water and CO2 (Cover image: Verena A. Resch).

    3. You have free access to this content
      Inside Back Cover: Single-Crystal Semiconductors with Narrow Band Gaps for Solar Water Splitting (Angew. Chem. Int. Ed. 37/2015) (page 10985)

      Assoc. Prof. Dr. Tuo Wang and Prof. Dr. Jinlong Gong

      Article first published online: 23 JUL 2015 | DOI: 10.1002/anie.201506277

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      Narrow-band-gap single-crystal semiconductors have been considered inappropriate for solar water splitting largely because of the photocorrosion issue. However, several exciting breakthroughs have shown that the instability and other drawbacks of these materials can be overcome. In their Minireview on page 10718 ff., T. Wang and J. Gong describe recent research advances and highlight the most important approaches to using these semiconductors as efficient photoelectrodes.

    4. Back Cover: Growth of High-Quality, Thickness-Reduced Zeolite Membranes towards N2/CH4 Separation Using High-Aspect-Ratio Seeds (Angew. Chem. Int. Ed. 37/2015) (page 10986)

      Yi Huang, Lei Wang, Zhuonan Song, Shiguang Li and Miao Yu

      Article first published online: 21 AUG 2015 | DOI: 10.1002/anie.201507477

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      Greatly improved zeolite membranes were prepared by using high-aspect-ratio zeolite seeds. In their Communication on page 10843 ff., S. Li, M. Yu, et al. report about slice-shaped seeds with a large aspect ratio that facilitate growth of thinner SAPO-34 membranes with much higher quality. These membranes show high performance in separating N2/CH4 mixtures. Fine tuning the crystal structure by changing the crystal composition might be a feasible way for further improving the separating performance.

  2. Frontispiece

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. Frontispiece: Coupling Mo2C with Nitrogen-Rich Nanocarbon Leads to Efficient Hydrogen-Evolution Electrocatalytic Sites

      Yipu Liu, Prof. Guangtao Yu, Prof. Guo-Dong Li, Yuanhui Sun, Prof. Tewodros Asefa, Prof. Wei Chen and Prof. Xiaoxin Zou

      Article first published online: 1 SEP 2015 | DOI: 10.1002/anie.201583761

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      Hydrogen Evolution. In their Communication on page 10751 ff., T. Asefa, W. Chen, X. Zou, et al. report an efficient hybrid hydrogen-evolution electrocatalyst consisting of molybdenum carbide nanoparticles embedded in nitrogen-rich carbon nanolayers. The synergistic effect between Mo2C and N dopants co-activates adjacent C atoms on the carbon nanolayers.

  3. Editorial

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. You have free access to this content
      Porous Materials and the Age of Gas (pages 10686–10687)

      Prof. Dr. Susumu Kitagawa

      Article first published online: 17 JUN 2015 | DOI: 10.1002/anie.201503835

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      “… Materials that achieve mass storage and highly efficient separation of gases cannot be realized by simply improving conventional technology. The achievements in the field of metal–organic frameworks have rapidly and significantly advanced materials research that is vital to addressing energy and environmental issues…” Read more in the Editorial by Susumu Kitagawa.

  4. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
  5. News

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
  6. Author Profile

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. Jose Luis Mascareñas (page 10710)

      Article first published online: 1 MAY 2015 | DOI: 10.1002/anie.201503243

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      “When I was eighteen I wanted to be an inventor. I advise my students to be open-minded and never stop questioning. ...” This and more about Jose Luis Mascareñas can be found on page 10710.

  7. News

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
  8. Highlight

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. Epigenetics

      N6-Methyladenine: A Potential Epigenetic Mark in Eukaryotic Genomes (pages 10714–10716)

      Dr. Daniel Summerer

      Article first published online: 17 JUL 2015 | DOI: 10.1002/anie.201504594

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      N6-methyladenine (6mA) is known to be an epigenetic mark in bacterial genomes. Three studies have now demonstrated the existence of significant levels of 6mA in the genomes of several phylogenetically distinct eukaryotes, along with findings that suggest that 6mA may act as a dynamic epigenetic mark in the regulation of eukaryotic gene expression.

  9. Minireview

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. Sustainable Chemistry

      Single-Crystal Semiconductors with Narrow Band Gaps for Solar Water Splitting (pages 10718–10732)

      Assoc. Prof. Dr. Tuo Wang and Prof. Dr. Jinlong Gong

      Article first published online: 23 JUL 2015 | DOI: 10.1002/anie.201503346

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      With suitable band gaps and low bulk recombination, single-crystal semiconductors with narrow band gaps have shown excellent performance in solar water splitting. This Minireview describes recent research advances in using these semiconductors as efficient photoelectrodes, where surface protection, co-catalyst loading, surface energetics matching, and surface texturization are proposed as the most important approaches to realized high activity.

  10. Review

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. Supported Graphene

      The Covalent Functionalization of Graphene on Substrates (pages 10734–10750)

      Dr. Alejandro Criado, Dr. Michele Melchionna, Dr. Silvia Marchesan and Prof. Maurizio Prato

      Article first published online: 4 AUG 2015 | DOI: 10.1002/anie.201501473

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      Covalent modification of graphene on substrates allows fine control of its chemical structure and opening of the bandgap for electronic applications. The graphene type and morphology, the nature of the substrate, and mechanical forces are key factors affecting reactivity. Analysis of these parameters and comparison of the different functionalization routes is essential to make an informed choice when working with functionalized graphene on a support.

  11. Communications

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. Hydrogen-Evolution Reaction

      Coupling Mo2C with Nitrogen-Rich Nanocarbon Leads to Efficient Hydrogen-Evolution Electrocatalytic Sites (pages 10752–10757)

      Yipu Liu, Prof. Guangtao Yu, Prof. Guo-Dong Li, Yuanhui Sun, Prof. Tewodros Asefa, Prof. Wei Chen and Prof. Xiaoxin Zou

      Article first published online: 23 JUL 2015 | DOI: 10.1002/anie.201504376

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      Hybrid catalyst: An efficient hybrid hydrogen-evolution electrocatalyst containing molybdenum carbide nanoparticles embedded in nitrogen-rich carbon nanolayers has been synthesized in one-step from inexpensive precursors. The synergistic effect between Mo2C and N dopants was found to yield very active nonmetallic HER catalytic sites on the carbon nanolayers.

    2. CO2 Reduction

      Metal-Doped Nitrogenated Carbon as an Efficient Catalyst for Direct CO2 Electroreduction to CO and Hydrocarbons (pages 10758–10762)

      Dr. Ana Sofia Varela, Dr. Nastaran Ranjbar Sahraie, Julian Steinberg, Wen Ju, Dr. Hyung-Suk Oh and Prof. Dr. Peter Strasser

      Article first published online: 29 JUL 2015 | DOI: 10.1002/anie.201502099

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      The kinetics, mechanism, and active sites of the CO2 electroreduction reaction (CO2RR) to syngas and hydrocarbons on solid carbon-based catalysts doped with nitrogen, Fe, and/or Mn are explored. The solid powder catalysts are active and highly CO selective in CO2RR to CO/H2 mixtures, outperforming a low-area polycrystalline gold benchmark.

    3. Reaction Intermediates | Very Important Paper

      Time-Resolved Crystallography of the Reaction Intermediate of Nitrile Hydratase: Revealing a Role for the Cysteinesulfenic Acid Ligand as a Catalytic Nucleophile (pages 10763–10767)

      Dr. Yasuaki Yamanaka, Dr. Yuki Kato, Dr. Koichi Hashimoto, Dr. Keisuke Iida, Prof. Kazuo Nagasawa, Dr. Hiroshi Nakayama, Dr. Naoshi Dohmae, Prof. Keiichi Noguchi, Prof. Takumi Noguchi, Prof. Masafumi Yohda and Prof. Masafumi Odaka

      Article first published online: 14 AUG 2015 | DOI: 10.1002/anie.201502731

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      Visualizing enzyme reactions: The catalytic reaction of nitrile hydratase is monitored by time-resolved crystallography (see picture; C gray, N blue, O red, S yellow, Fe orange). Upon light-induced release of NO, the substrate observed in the pocket turned to bind to the Fe ion to form a cyclic reaction intermediate. The structure of the intermediate shows that the coordinated substrate is attacked by the sulfenate ligand.

    4. Organoborane Macrocycles

      Versatile Design Principles for Facile Access to Unstrained Conjugated Organoborane Macrocycles (pages 10768–10772)

      Dr. Pangkuan Chen, Dr. Xiaodong Yin, Nurcan Baser-Kirazli and Prof. Dr. Frieder Jäkle

      Article first published online: 26 JUN 2015 | DOI: 10.1002/anie.201503219

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      Changing shapes: Guided by theoretical calculations, the conjugated fluorene bridges or the borane moieties in a strained tetramer are partially replaced with carbazoles, resulting in hybrid macrocycles with new shapes and sizes. These macrocycles are ambipolar and show interesting emission characteristics and anion response, including anion-triggered geometry changes.

    5. Fluorination

      Diphenyliodonium-Catalyzed Fluorination of Arynes: Synthesis of ortho-Fluoroiodoarenes (pages 10773–10777)

      Dr. Yuwen Zeng, Dr. Guangyu Li and Prof. Dr. Jinbo Hu

      Article first published online: 23 JUL 2015 | DOI: 10.1002/anie.201503308

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      iCatalysis: A diphenyliodonium salt proved to be a privileged catalyst for nucleophilic fluorination of arynes using CsF as a fluorine source. A subsequent electrophilic iodination with C4F9I was also found to be crucial to ensure the efficient fluorination step.

    6. Imaging Agents

      Synthesis and Evaluation of GdIII-Based Magnetic Resonance Contrast Agents for Molecular Imaging of Prostate-Specific Membrane Antigen (pages 10778–10782)

      Dr. Sangeeta Ray Banerjee, Dr. Ethel J. Ngen, Matthew W. Rotz, Dr. Samata Kakkad, Ala Lisok, Richard Pracitto, Mrudula Pullambhatla, Dr. Zhengping Chen, Dr. Tariq Shah, Dr. Dmitri Artemov, Dr. Thomas J. Meade, Dr. Zaver M. Bhujwalla and Dr. Martin G. Pomper

      Article first published online: 23 JUL 2015 | DOI: 10.1002/anie.201503417

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      Good visibility: The relaxometric properties of a rationally designed high-affinity trimeric GdIII-based contrast agent were evaluated in prostate cancer cells and in an in vivo experimental model (see picture; ΔR1 measures contrast enhancement from 0 % (blue) to 50 % (red)) to demonstrate the feasibility of magnetic resonance molecular imaging of cells and tissues expressing prostate-specific membrane antigen (PSMA).

    7. Magnetic Anisotropy

      Spectroscopic and Crystal Field Consequences of Fluoride Binding by [Yb⋅DTMA]3+ in Aqueous Solution (pages 10783–10786)

      Dr. Octavia A. Blackburn, Dr. Nicholas F. Chilton, Katharina Keller, Dr. Claudia E. Tait, Dr. William K. Myers, Prof. Eric J. L. McInnes, Dr. Alan M. Kenwright, Prof. Paul D. Beer, Prof. Christiane R. Timmel and Prof. Stephen Faulkner

      Article first published online: 27 JUL 2015 | DOI: 10.1002/anie.201503421

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      F makes the difference: [Yb⋅DTMA⋅OH2]3+ and [Yb⋅DTMA⋅F]2+ are in slow exchange on the NMR timescale (kex<2000 s−1), and profound differences are observed in the NMR and EPR spectra of these species. This behavior is explained by changes in the magnetic anisotropy of the YbIII ground state from easy-axis to easy-plane type (see picture).

    8. Lithium-Ion Batteries

      Hydrothermal Synthesis of Unique Hollow Hexagonal Prismatic Pencils of Co3V2O8n H2O: A New Anode Material for Lithium-Ion Batteries (pages 10787–10791)

      Dr. Fangfang Wu, Prof. Shenglin Xiong, Prof. Yitai Qian and Prof. Shu-Hong Yu

      Article first published online: 23 JUL 2015 | DOI: 10.1002/anie.201503487

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      Hydrothermal synthesis: A new phase of Co3V2O8n H2O hollow hexagonal prismatic pencils has been synthesized hydrothermally by varying the amount of NaOH in the reaction in the presence of NH4+ ions and absence of any template or surfactant (see picture). The excellent electrochemical activity results from the unique structure of Co3V2O8n H2O and probably from synergetic effects of different metal ions.

    9. Fused-Ring Systems

      Extended Corannulenes: Aromatic Bowl/Sheet Hybridization (pages 10792–10796)

      Dr. Amit K. Dutta, Prof. Dr. Anthony Linden, Dr. Laura Zoppi, Prof. Dr. Kim K. Baldridge and Prof. Dr. Jay S. Siegel

      Article first published online: 24 JUL 2015 | DOI: 10.1002/anie.201503553

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      Caught and bowled: Photophysical and voltammetric studies together with high-level computations have been carried out on polynuclear aromatic hydrocarbons with distinct planar and bowl regions. A buckybowl–graphene hybrid was synthesized (see X-ray structure) as a model by activation of a C(Ar)[BOND]F bond. Curvature and extended π-effects were found to affect the properties of such materials.

    10. Reaction Yields

      A Priori Estimation of Organic Reaction Yields (pages 10797–10801)

      Dr. Fateme S. Emami, Dr. Amir Vahid, Elizabeth K. Wylie, Sara Szymkuć, Dr. Piotr Dittwald, Karol Molga and Prof. Bartosz A. Grzybowski

      Article first published online: 21 JUL 2015 | DOI: 10.1002/anie.201503890

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      Getting to grips with yields: A thermodynamically guided calculation of free energies of substrate and product molecules allows the a priori estimation of the yields of organic reactions to be made. The model is first trained on a diverse set of reactions and reaction yields, and can then estimate the yields of other reactions with the accuracy of ±15 %.

    11. Carbon Nanotubes | Hot Paper

      Template Synthesis of Linear-Chain Nanodiamonds Inside Carbon Nanotubes from Bridgehead-Halogenated Diamantane Precursors (pages 10802–10806)

      Yusuke Nakanishi, Dr. Haruka Omachi, Dr. Natalie A. Fokina, Prof. Dr. Peter R. Schreiner, Prof. Dr. Ryo Kitaura, Dr. Jeremy E. P. Dahl, Prof. Dr. Robert M. K. Carlson and Prof. Dr. Hisanori Shinohara

      Article first published online: 12 AUG 2015 | DOI: 10.1002/anie.201504904

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      Long diamonds: A simple method for the synthesis of linear-chain diamond-like nanomaterials, so-called diamantane polymers, is described. This synthetic approach is primarily based on a template reaction of dihalogen-substituted diamantane precursors in the hollow cavities of carbon nanotubes. The present strategy may be used for the design and synthesis of other one-dimensional nanomaterials.

    12. Foldamers

      Fine Tuning of β-Peptide Foldamers: a Single Atom Replacement Holds Back the Switch from an 8-Helix to a 12-Helix (pages 10807–10810)

      Dr. Amandine Altmayer-Henzien, Dr. Valérie Declerck, Dr. Jonathan Farjon, Prof. Dr. Denis Merlet, Dr. Régis Guillot and Prof. Dr. David J. Aitken

      Article first published online: 23 JUL 2015 | DOI: 10.1002/anie.201504126

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      Keep it long and slim: Although a stable 12-helix conformer is available to oligo-β-peptides constructed from cyclic monomers, when an aza-adapted N terminus is incorporated, the resulting hydrazino turn feature leads the foldamer to preferentially adopt a more slimline 8-helix. This effect illustrates atomic-level programmable design for the fine tuning of peptide foldamer architectures.

    13. Hybrid Materials

      Room-Temperature, Strain-Tunable Orientation of Magnetization in a Hybrid Ferromagnetic Co Nanorod–Liquid Crystalline Elastomer Nanocomposite (pages 10811–10815)

      Dr. Ophélie Riou, Dr. Barbara Lonetti, Dr. Reasmey P. Tan, Justine Harmel, Dr. Katerina Soulantica, Dr. Patrick Davidson, Dr. Anne-Françoise Mingotaud, Dr. Marc Respaud, Dr. Bruno Chaudret and Dr. Monique Mauzac

      Article first published online: 17 JUL 2015 | DOI: 10.1002/anie.201504320

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      A highly anisotropic magnetic material with a strain tunable orientation of the magnetic direction was synthesized. In this material Co nanorods are aligned through a cross-linking process performed in the presence of an external magnetic field. The nanorod alignment can be switched at will at room temperature.

    14. Lipid Bilayers

      Amphiphilic Nanoparticles Control the Growth and Stability of Lipid Bilayers with Open Edges (pages 10816–10820)

      Sun Hae Ra Shin, Prof. Hee-Young Lee and Prof. Kyle J. M. Bishop

      Article first published online: 23 JUL 2015 | DOI: 10.1002/anie.201504362

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      Nanoparticle surfactants that present mixtures of hydrophilic and hydrophobic ligands on their surface bind selectively at the open edge of bilayer membranes to stabilize amphiphile assemblies and control their growth. This general mechanism can be applied to inhibit formation of undesired assemblies such as cholesterol gallstones and to direct the growth of lipid nanostructures.

    15. Imaging Probes | Hot Paper

      A Small-Molecule Probe for Selective Profiling and Imaging of Monoamine Oxidase B Activities in Models of Parkinson’s Disease (pages 10821–10825)

      Dr. Lin Li, Dr. Cheng-Wu Zhang, Dr. Jingyan Ge, Linghui Qian, Bing-Han Chai, Prof. Dr. Qing Zhu, Prof. Dr. Jun-Seok Lee, Prof. Dr. Kah-Leong Lim and Prof. Dr. Shao Q. Yao

      Article first published online: 21 JUL 2015 | DOI: 10.1002/anie.201504441

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      Seeing is believing: A dual-purpose small-molecule activity-based probe (M2) was developed for imaging the activity of monoamine oxidase B (MAO-B). In situ proteome profiling and live-cell bioimaging of endogenous MAO-B activities from a variety of biological samples, including Parkinson’s disease models, can thus be carried out simultaneously.

    16. Biomolecular Self-Assembly

      A Single Stereodynamic Center Modulates the Rate of Self-Assembly in a Biomolecular System (pages 10826–10832)

      Yitao Zhang, Roy M. Malamakal and Prof. David M. Chenoweth

      Article first published online: 23 JUL 2015 | DOI: 10.1002/anie.201504459

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      The influence of asymmetric carbon on biopolymer folding is of great importance as a general pre-organizing element in life processes. It is shown that a single C to N mutation in a collagen model peptide leads to a higher order structure with similar thermal unfolding but drastically different kinetic refolding behavior.

    17. Polymorphism

      Structure Elucidation and Characterization of Different Thyroxine Polymorphs (pages 10833–10837)

      Santanu Mondal and Prof. Dr. Govindasamy Mugesh

      Article first published online: 24 JUL 2015 | DOI: 10.1002/anie.201505281

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      You’d better shape up: Two new polymorphs of the thyroid hormone thyroxine were characterized and it was found that polymorphism has a significant effect on the solubility and stability of this clinically useful compound. The conformational changes alter the electronic properties of the iodine atoms and the reactivity of the C[BOND]I bonds, which could have a significant effect on the hormone activity.

    18. Microfluidics

      High-Throughput, Label-Free Isolation of Cancer Stem Cells on the Basis of Cell Adhesion Capacity (pages 10838–10842)

      Yuanqing Zhang, Minhao Wu, Xin Han, Ping Wang and Lidong Qin

      Article first published online: 15 JUL 2015 | DOI: 10.1002/anie.201505294

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      Stick with this one: When cancer cells were driven by hydrodynamic forces to flow through microchannels coated with basement membrane extract, highly adhesive cells were captured by the microchannels, and less adhesive cells were collected from the outlets (see picture). The less adhesive phenotype of two cancer cell lines was found to have a higher percentage of cancer stem cells, higher motility, and higher resistance to chemotherapeutic drugs.

    19. Membranes

      Growth of High-Quality, Thickness-Reduced Zeolite Membranes towards N2/CH4 Separation Using High-Aspect-Ratio Seeds (pages 10843–10847)

      Yi Huang, Lei Wang, Zhuonan Song, Shiguang Li and Miao Yu

      Article first published online: 6 AUG 2015 | DOI: 10.1002/anie.201503782

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      Slice-shaped zeolites: Thin SAPO-34 membranes of high quality were grown by using high-aspect-ratio SAPO-34 crystal seeds (see picture). A simultaneous increase in the N2 permeance and N2/CH4 separation selectivity of the membranes was achieved. Incorporation of more Si into the crystal structure of these thin membranes resulted in a significantly increased N2 permeance, while the N2/CH4 selectivity was maintained.

    20. Zeolite Catalysts | Very Important Paper

      Self-Pillared, Single-Unit-Cell Sn-MFI Zeolite Nanosheets and Their Use for Glucose and Lactose Isomerization (pages 10848–10851)

      Dr. Limin Ren, Dr. Qiang Guo, Prashant Kumar, Marat Orazov, Dandan Xu, Prof. Saeed M. Alhassan, Prof. K. Andre Mkhoyan, Prof. Mark E. Davis and Prof. Michael Tsapatsis

      Article first published online: 23 JUL 2015 | DOI: 10.1002/anie.201505334

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      The adventures of thin tin: Sn is introduced in the framework of single-unit-cell (2 nm thick) zeolite MFI lamellae, which are intergrown in a self-pillared arrangement to obtain a hierarchical micro/mesoporous Lewis acid catalyst. Its conversion and selectivity are better than those of other micro- and mesoporous Sn-containing catalysts for isomerization of mono- and disacharides.

    21. Protein Profiling

      Proteome-Wide Profiling of Targets of Cysteine reactive Small Molecules by Using Ethynyl Benziodoxolone Reagents (pages 10852–10857)

      Daniel Abegg, Dr. Reto Frei, Luca Cerato, Dr. Durga Prasad Hari, Chao Wang, Prof. Dr. Jerome Waser and Prof. Dr. Alexander Adibekian

      Article first published online: 24 JUL 2015 | DOI: 10.1002/anie.201505641

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      Good grip: Alkynyl benziodoxolones (EBX reagents) swiftly and highly selectively react with cysteine residues in cellular lysates and in living cells under physiological conditions. A “clickable” EBX probe allowed identification of the biological targets of natural product curcumin. This new method for cysteine labeling is particularly useful for various chemical proteomics applications.

    22. EPR Spectroscopy

      g-Engineering in Hybrid Rotaxanes To Create AB and AB2 Electron Spin Systems: EPR Spectroscopic Studies of Weak Interactions between Dissimilar Electron Spin Qubits (pages 10858–10861)

      Dr. Antonio Fernandez, Dr. Eufemio Moreno Pineda, Dr. Christopher A. Muryn, Dr. Stephen Sproules, Dr. Fabrizio Moro, Dr. Grigore A. Timco, Prof. Eric J. L. McInnes and Prof. Richard E. P. Winpenny

      Article first published online: 24 JUL 2015 | DOI: 10.1002/anie.201504487

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      Spin control: Hybrid [2]rotaxanes and pseudorotaxanes, such as {[Cu(hfac)2][PyCH2NH2CH2CH2Ph][Cr7Ni(μ-F)8(O2CtBu)16]} (see picture; Hhfac=1,1,1,6,6,6-hexafluoroacetylacetone), are reported where the magnetic interaction between dissimilar spins is controlled to create AB and AB2 electron spin systems, allowing independent control of weakly interacting S=1/2 centers. Atom colors: Cr=green, Ni=purple, Cu=dark blue, F=yellow, O=red, C=gray, N=pale blue.

    23. Light-Emitting Diodes | Hot Paper

      Waterproof Alkyl Phosphate Coated Fluoride Phosphors for Optoelectronic Materials (pages 10862–10866)

      Dr. Hoang-Duy Nguyen, Dr. Chun Che Lin and Prof. Dr. Ru-Shi Liu

      Article first published online: 23 JUL 2015 | DOI: 10.1002/anie.201504791

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      The moisture instability of fluoride phosphors has limited their application in optoelectronic devices. Their waterproof properties can be improved by a hydrophobic coating layer, such as an alkyl phosphate. The luminous efficacy of warm white-light-emitting diodes (WLEDs) based on such coated phosphors is remarkably stable even under high-humidity and high-temperature conditions.

    24. Protein Folding

      Frustration Sculpts the Early Stages of Protein Folding (pages 10867–10869)

      Dr. Eva Di Silvio, Prof. Maurizio Brunori and Prof. Stefano Gianni

      Article first published online: 23 JUL 2015 | DOI: 10.1002/anie.201504835

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      Diverging demands between folding and function cause a pattern of local frustration in proteins. By comparing the folding of proteins sharing nearly identical sequence and structure but displaying different frustration, it may be observed how frustration sculpts the early stages of folding whereas the late stages are more robust and biased by native topology.

    25. Perovskites | Hot Paper

      Rattling in the Quadruple Perovskite CuCu3V4O12 (pages 10870–10874)

      Dr. Yasuhide Akizuki, Dr. Ikuya Yamada, Dr. Koji Fujita, Kazuya Taga, Dr. Takateru Kawakami, Dr. Masaichiro Mizumaki and Prof. Katsuhisa Tanaka

      Article first published online: 23 JUL 2015 | DOI: 10.1002/anie.201504784

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      Oversize me: CuCu3V4O12 is synthesized using a high-pressure technique. This compound adopts the cubic A-site ordered perovskite-type structure (space group Imequation image) with a valence distribution of Cu2+Cu2+3V4+4O12. It has oversized icosahedral cages in which loosely bound A-site Cu2+ ions rattle with a characteristic temperature (Einstein temperature) of ΘE≈55 K. This is the first demonstration of rattling in perovskites.

    26. Total Synthesis

      Biomimetic Total Synthesis of (−)-Penibruguieramine A Using Memory of Chirality and Dynamic Kinetic Resolution (pages 10875–10878)

      Jae Hyun Kim, Seokwoo Lee and Prof. Dr. Sanghee Kim

      Article first published online: 21 JUL 2015 | DOI: 10.1002/anie.201504954

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      Chiral survival: The fully stereocontrolled total synthesis of (−)-penibruguieramine A is described. The principles of “memory of chirality” (MOC) and “dynamic kinetic resolution” (DKR) are applied to the biomimetic aldol reaction for the asymmetric synthesis, using proline as the only chiral source.

    27. Biodegradable Polymers

      Acid-Labile Thermoresponsive Copolymers That Combine Fast pH-Triggered Hydrolysis and High Stability under Neutral Conditions (pages 10879–10883)

      Dr. Qilu Zhang, Zhanyao Hou, Benoit Louage, Dr. Dingying Zhou, Nane Vanparijs, Prof. Dr. Bruno G. De Geest and Prof. Dr. Richard Hoogenboom

      Article first published online: 24 JUL 2015 | DOI: 10.1002/anie.201505145

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      Breaking the rules: Thermoresponsive polymers with both dimethyldioxolane and hydroxyethyl side chains were hydrolyzed rapidly under slightly acidic conditions while being stable at pH 7.4 or during storage: important properties for biomedical applications. Thus, hydrolysis of the acid-labile cyclic-acetal groups was accelerated by the presence of hydroxy groups, which led to enhanced hydration of the collapsed copolymer globules (see picture).

    28. Cross-Coupling

      Catalytic Synthesis of N-Unprotected Piperazines, Morpholines, and Thiomorpholines from Aldehydes and SnAP Reagents (pages 10884–10888)

      Michael U. Luescher and Prof. Dr. Jeffrey W. Bode

      Article first published online: 23 JUL 2015 | DOI: 10.1002/anie.201505167

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      SnAPcat! The identification of new ligands and reaction conditions provides a robust catalytic method for the synthesis of N-unprotected heterocycles using SnAP reagents. This catalytic variant expands the substrate scope to include previously inaccessible piperazines, morpholines, and thiomorpholines and establishes the basis for a catalytic enantioselective process through the use of chiral ligands.

    29. Metal–Organic Frameworks

      Hollow Zn/Co ZIF Particles Derived from Core–Shell ZIF-67@ZIF-8 as Selective Catalyst for the Semi-Hydrogenation of Acetylene (pages 10889–10893)

      Jian Yang, Fengjun Zhang, Haiyuan Lu, Xun Hong, Hailong Jiang, Yuen Wu and Yadong Li

      Article first published online: 5 AUG 2015 | DOI: 10.1002/anie.201504242

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      A mild phase transformation of ZIF-67@ZIF-8 core–shell structures is achieved under solvothermal conditions to generate unique hollow Zn/Co ZIF particles, which were used to generate Pd@MOF yolk-shell composites. They exhibit enhanced gas storage and high catalytic activity and selectivity in the semi-hydrogenation of acetylene.

    30. Glycosylations

      Stereoselective Synthesis of α-3-Deoxy-D-manno-oct-2-ulosonic Acid (α-Kdo) Glycosides Using 5,7-O-Di-tert-butylsilylene-Protected Kdo Ethyl Thioglycoside Donors (pages 10894–10898)

      Jia-Sheng Huang, Wei Huang, Xue Meng, Xin Wang, Peng-Cheng Gao and Prof. Dr. Jin-Song Yang

      Article first published online: 23 JUL 2015 | DOI: 10.1002/anie.201505176

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      A Kdo K.O.: The title compound is a common structural constituent of polysaccharides present in bacteria. An approach to stereospecific synthesis of α-Kdo glycosides was developed by using 5,7-O-di-tert-butylsilylene-protected Kdo ethyl thioglycoside donors (1). Various α-Kdo glycosidic linkages were constructed in good to excellent chemical yields with complete α-selectivity (2). M.S.=molecular sieves, NIS=N-iodosuccinimide, Tf=trifluoromethanesulfonyl.

    31. Biocatalysis

      Vinylation of Unprotected Phenols Using a Biocatalytic System (pages 10899–10902)

      Dr. Eduardo Busto, Dr. Robert C. Simon and Prof. Dr. Wolfgang Kroutil

      Article first published online: 29 JUL 2015 | DOI: 10.1002/anie.201505696

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      Make it simple! A biocatalytic system for the selective para vinylation of substituted phenols provides the desired products with >99 % conversion in water. An efficient metal-free method for the atom-economic preparation of para-vinylphenols under mild reaction conditions has thus been developed.

    32. Cyclizations

      Gold(I)-Catalyzed Tandem Transformation with Diynes: Rapid Access to Linear Cyclopentenone-Fused Polycyclic Molecules (pages 10903–10907)

      Congjun Yu, Bin Chen, Tian Zhou, Qingshan Tian and Prof. Dr. Guozhu Zhang

      Article first published online: 16 JUL 2015 | DOI: 10.1002/anie.201503599

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      Linear cycles: An efficient and convenient synthesis of the title compounds has been achieved through a gold(I)-catalyzed transformation of diynes. A novel mechanism involving gold vinylidene formation, methoxy group migration, and a Nazarov-type cyclization is postulated. DCE=1,2-dichloroethane, IPr=1,3-bis(diisopropylphenyl)imidazol-2-ylidene, Tf=trifluoromethanesulfonyl.

    33. Expanded Porphyrins

      A Stable Organic π-Radical of a Zinc(II)–Copper(I)–Zinc(II) Complex of Decaphyrin (pages 10908–10911)

      Dr. Yasuo Tanaka, Dr. Tomoki Yoneda, Prof. Dr. Ko Furukawa, Dr. Taro Koide, Hirotaka Mori, Dr. Takayuki Tanaka, Prof. Dr. Hiroshi Shinokubo and Prof. Dr. Atsuhiro Osuka

      Article first published online: 17 JUL 2015 | DOI: 10.1002/anie.201505130

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      Radical racetrack: CuII metalation of a [46]decaphyrin bis(ZnII) complex gave a ZnII-CuI-ZnII heterotrimetal complex of decaphyrin consisting of a central CuI ion and a monoanionic 45π radical of decaphyrin. Despite the radical nature, the complex is fairly stable under ambient conditions. This stability is probably due to the effective delocalization of an unpaired electron over the whole π-conjugation network of the decaphyrin.

    34. Synthetic Methods

      Palladium-Catalyzed Dearomative Cyclocarbonylation by C[BOND]N Bond Activation (pages 10912–10916)

      Hui Yu, Guoying Zhang and Prof. Dr. Hanmin Huang

      Article first published online: 21 JUL 2015 | DOI: 10.1002/anie.201504805

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      Dearomatization: A highly efficient dearomative cyclocarbonylation reaction proceeds by palladium-catalyzed C[BOND]N bond activation, dearomatization, CO insertion, and a Heck reaction. This transformation represents the first general catalytic method for the synthesis of valuable bioactive quinolizinones.

    35. Asymmetric Catalysis

      An Enantioselective Synthesis of Spirobilactams through Copper-Catalyzed Intramolecular Double N-Arylation and Phase Separation (pages 10917–10920)

      Jianguang Liu, Yingying Tian, Jialing Shi, Shasha Zhang and Prof. Dr. Qian Cai

      Article first published online: 23 JUL 2015 | DOI: 10.1002/anie.201504589

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      Spirocyclic structures are versatile building blocks for functional chiral molecules. A copper-catalyzed double N-arylation was developed for the enantioselective synthesis of chiral spirobilactams. Enantioenriched spirobilactams were obtained with excellent ee values through precipitation of the racemate and simple solid–solution phase separation.

    36. Cluster Compounds

      From Mesomorphic Phosphine Oxide to Clustomesogens Containing Molybdenum and Tungsten Octahedral Cluster Cores (pages 10921–10925)

      Dr. Viorel Cîrcu, Dr. Yann Molard, Dr. Maria Amela-Cortes, Ahmed Bentaleb, Dr. Philippe Barois, Dr. Vincent Dorcet and Dr. Stéphane Cordier

      Article first published online: 21 JUL 2015 | DOI: 10.1002/anie.201503205

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      Clustomesogens are metal atom clusters containing liquid-crystalline materials. They have been obtained by grafting neutral cyanobiphenyl- or cholesteryl-containing tailor-made dendritic mesomorphic triphenylphosphine oxide ligands on luminescent (M6Cli8)4+ octahedral cluster cores (M=Mo, W).

    37. Heterocycle Synthesis

      Synthesis of 3,4,5-Trisubstituted Isoxazoles from Morita–Baylis–Hillman Acetates by an NaNO2/I2-Mediated Domino Reaction (pages 10926–10930)

      Shashikant U. Dighe, Sushobhan Mukhopadhyay, Shivalinga Kolle, Dr. Sanjeev Kanojiya and Sanjay Batra

      Article first published online: 23 JUL 2015 | DOI: 10.1002/anie.201504529

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      An efficient synthesis of highly substituted isoxazoles from the reaction of allyl acetates with NaNO2 by using I2 under oxidative conditions is demonstrated. The reactions proceed through an I2-assisted activation of the C[BOND]H bond α to the nitro group, nucleophilic addition, and subsequent [3+2] cycloaddition. DMF=N,N-dimethylformamide, DMSO=dimethylsulfoxide.

    38. Peptide Macrocyclization

      A Thiol–Ene Coupling Approach to Native Peptide Stapling and Macrocyclization (pages 10931–10934)

      Dr. Yuanxiang Wang and Prof. Dr. Danny Hung-Chieh Chou

      Article first published online: 17 JUL 2015 | DOI: 10.1002/anie.201503975

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      The selective modification of cysteine residues in native, unprotected peptides with a variety of stapling modifications for helix stabilization or general macrocyclization is achieved by a new peptide stapling and macrocyclization method. This method uses thiol–ene reactions between two cysteine residues and a diene and gives high yields.

    39. Carbohydrates

      Regioselective and 1,2-cis-α-Stereoselective Glycosylation Utilizing Glycosyl-Acceptor-Derived Boronic Ester Catalyst (pages 10935–10939)

      Akira Nakagawa, Masamichi Tanaka, Shun Hanamura, Dr. Daisuke Takahashi and Prof. Dr. Kazunobu Toshima

      Article first published online: 23 JUL 2015 | DOI: 10.1002/anie.201504182

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      Donors and acceptors: The title reaction of 1α,2α-anhydro glycosyl donors and diol glycosyl acceptors proceeded smoothly to give the corresponding 1,2-cis-α-glycosides with high stereo- and regioselectivities. The glycosylation method was successfully applied to the synthesis of an isoflavone glycoside.

    40. Natural Products

      Enantioselective Total Synthesis of (−)-Hosieine A (pages 10940–10943)

      Jie Ouyang, Rui Yan, Xianwei Mi and Prof. Dr. Ran Hong

      Article first published online: 21 JUL 2015 | DOI: 10.1002/anie.201505251

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      An unprecedented nitroso-ene cyclization to construct the 2-azabicyclo[3.2.1]octane ring system was developed during the first total synthesis of (−)-Hosieine A, a novel Lupin alkaloid possessing high affinity towards the α4β2 receptor with nanomolar level potency. Noteworthy transformations are the phosphine-enabled stereoselective bromohydrination and facile radical debromination initiated by Et3B/air.

    41. Pseudoreversible Reactions

      Ruthenium-Catalyzed O- to S-Alkyl Migration: A Pseudoreversible Barton–McCombie Pathway (pages 10944–10948)

      William Mahy, Dr. Pawel Plucinski, Dr. Jesús Jover and Prof. Dr. Christopher G. Frost

      Article first published online: 27 JUL 2015 | DOI: 10.1002/anie.201505280

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      A radical step in a new direction: A practical ruthenium-catalyzed O- to S-alkyl migration affords structurally diverse thiooxazolidinones in excellent yields. Experimental and computational studies suggest a pseudoreversible radical pathway drawing mechanistic parallels to the classic Barton–McCombie reaction.

    42. Asymmetric Annulation

      Hydroxoiridium/Chiral Diene Complexes as Effective Catalysts for Asymmetric Annulation of α-Oxo- and Iminocarboxamides with 1,3-Dienes (pages 10949–10952)

      Miyuki Hatano and Dr. Takahiro Nishimura

      Article first published online: 27 JUL 2015 | DOI: 10.1002/anie.201505382

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      [3+2] annulation: The asymmetric [3+2] annulation of α-oxo- and α-iminocarboxamides with 1,3-dienes catalyzed by hydroxoiridium/chiral diene complexes was achieved. The reaction gives the corresponding γ-lactams in high yields with high enantioselectivity.

    43. Oligosaccharides

      Synthetic Enterobacterial Common Antigen (ECA) for the Development of a Universal Immunotherapy for Drug-Resistant Enterobacteriaceae (pages 10953–10957)

      Dr. Lin Liu, Jingying Zha, Dr. Antonio DiGiandomenico, Dr. Douglas McAllister, Dr.  C. Kendall Stover, Dr. Qun Wang and Prof. Geert-Jan Boons

      Article first published online: 24 JUL 2015 | DOI: 10.1002/anie.201505420

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      Hitting the sweet spot: All Enterobacteriaceae express the polysaccharide enterobacterial common antigen (ECA), which is an attractive target for the development of universally acting immunotherapies. ECA-derived oligosaccharides were chemically synthesized and used to uncover immunodominant epitopes and develop a monoclonal antibody showing broad recognition of Enterobacteriaceae.

    44. Aza-Diels–Alder Reactions

      Regio- and Enantioselective Aza-Diels–Alder Reactions of 3-Vinylindoles: A Concise Synthesis of the Antimalarial Spiroindolone NITD609 (pages 10958–10962)

      Haifeng Zheng, Prof. Dr. Xiaohua Liu, Chaoran Xu, Yong Xia, Dr. Lili Lin and Prof. Dr. Xiaoming Feng

      Article first published online: 23 JUL 2015 | DOI: 10.1002/anie.201505717

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      An asymmetric aza-Diels–Alder reaction of 3-vinylindoles with isatin-derived ketimines leads to spiroindolone derivatives with high regio-, diastereo-, and enantioselectivity and also provides facile access to the valuable antimalarial drug NITD609. The stereoselectivity is thought to arise from π–π interactions between the two reactants and the chiral N,N′-dioxide ligand.

    45. Domino Reactions

      Stereoselective Retentive Domino Transmetalations of Secondary Alkyllithium Compounds to Functionalized Secondary Alkylcopper Reagents (pages 10963–10967)

      Kohei Moriya, Meike Simon, Rasmus Mose, Prof. Dr. Konstantin Karaghiosoff and Prof. Dr. Paul Knochel

      Article first published online: 14 AUG 2015 | DOI: 10.1002/anie.201505740

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      Configurationally retentive domino transmetalations of nonstabilized functionalized secondary alkyllithium compounds with Me3SiCH2ZnBr⋅LiBr and CuBr⋅ 2 LiCl⋅Me2S allow the preparation of secondary alkylcopper compounds with retention of configuration (TBDPS=tert-butyldiphenylsilyl). Trapping with a range of electrophiles (acid chlorides, ethylene oxide, alkynyl esters, ketals, allylic chlorides) afford various open-chain acyclic products.

    46. Pyrotechnics | Hot Paper

      Chlorine-Free Red-Burning Pyrotechnics (pages 10968–10970)

      Dr. Jesse J. Sabatini, Dr. Ernst-Christian Koch, Dr. Jay C. Poret, Dr. Jared D. Moretti and Seth M. Harbol

      Article first published online: 6 AUG 2015 | DOI: 10.1002/anie.201505829

      Thumbnail image of graphical abstract

      Seeing red: The emission from SrOH(g) alone is responsible for the red color of a chlorine-free high-intensity flare based on magnesium, strontium nitrate, 5-amino-1H-tetrazole or hexamine, and Epon binder. The detrimental orange emission from SrO(g) could be successfully suppressed. The new formulations avoid any risk of forming carcinogenic polychlorinated aromatic compounds and will positively impact civilian and military pyrotechnics.

    47. Molecular Evolution

      A Versatile Approach Towards Nucleobase-Modified Aptamers (pages 10971–10974)

      Fabian Tolle, Dr. Gerhard M. Brändle, Daniel Matzner and Prof. Dr. Günter Mayer

      Article first published online: 23 JUL 2015 | DOI: 10.1002/anie.201503652

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      Click to select: A versatile method for modular expansion of the chemical space of nucleic acid libraries has been developed. This method enables the generation of nucleobase-modified aptamers with unprecedented recognition properties. In situ reintroduction of the modification after enzymatic replication gives broad access to many chemical modifications, thus enabling the application of in vitro selection approaches beyond what is feasible to date.

    48. C[BOND]H Activation

      RhIII-Catalyzed C[BOND]H Activation with Pyridotriazoles: Direct Access to Fluorophores for Metal-Ion Detection (pages 10975–10979)

      Dr. Ju Hyun Kim, Tobias Gensch, Dr. Dongbing Zhao, Linda Stegemann, Priv.-Doz. Dr. Cristian A. Strassert and Prof. Dr. Frank Glorius

      Article first published online: 23 JUL 2015 | DOI: 10.1002/anie.201504757

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      Form(ation) follows function: The first C[BOND]H bond activation with pyridotriazoles as a coupling partner is made possible by using a RhIII catalyst. The pyridotriazoles serve as new carbene precursors in C[BOND]H activation allowing direct access to fluorescent scaffolds bearing a pyridine-type ligating group. These fluorophores can be applied as dual sensors for colorimetric sensing of Cu2+ ions and fluorescence sensing for Zn2+ ions.

    49. Peptides

      Design of Decorin-Based Peptides That Bind to Collagen I and their Potential as Adhesion Moieties in Biomaterials (pages 10980–10984)

      Dr. Stefania Federico, Dr. Benjamin F. Pierce, Dr. Susanna Piluso, Dr. Christian Wischke, Prof. Dr. Andreas Lendlein and Dr. Axel T. Neffe

      Article first published online: 23 JUL 2015 | DOI: 10.1002/anie.201505227

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      The ties that bind: The highly repetitive structure of the collagen-binding protein decorin allowed the design of peptides representative of each of its two distinct sides. Strongly binding peptides (red) derived from the inner surface were conjugated to a dye or dimerized. These peptides bind to collagen and provide a biomimetic tool for tailoring biomaterials by controlling mechanical properties or compound diffusion in collagen gels.

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