Angewandte Chemie International Edition

Cover image for Vol. 54 Issue 5

January 26, 2015

Volume 54, Issue 5

Pages 1371–1675

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Editorial
    5. Graphical Abstract
    6. Flashback
    7. News
    8. Author Profile
    9. Minireview
    10. Review
    11. Communications
    1. You have free access to this content
      Cover Picture: Magnetic Memory in an Isotopically Enriched and Magnetically Isolated Mononuclear Dysprosium Complex (Angew. Chem. Int. Ed. 5/2015) (page 1371)

      Dr. Fabrice Pointillart, Dr. Kevin Bernot, Dr. Stéphane Golhen, Dr. Boris Le Guennic, Thierry Guizouarn, Dr. Lahcène Ouahab and Dr. Olivier Cador

      Article first published online: 29 DEC 2014 | DOI: 10.1002/anie.201411877

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      The quantum tunneling in a mononuclear Dy-based single-molecule magnet (SMM) can be drastically reduced, improving the capability of the molecule to store magnetic information. As O. Cador and co-workers show in their Communication on page 1504 ff, this improvement is brought about by using isotopes of DyIII that do not have a nuclear magnetic moment and by dilution of the SMM in a diamagnetic matrix. Combined, these strategies lead to the opening of the hysteresis loop in zero field, and the relaxation time is increased.

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      Inside Cover: Quantitative Trace Analysis of Complex Mixtures Using SABRE Hyperpolarization (Angew. Chem. Int. Ed. 5/2015) (page 1372)

      Nan Eshuis, Bram J. A. van Weerdenburg, Dr. Martin C. Feiters, Prof. Dr. Floris P. J. T. Rutjes, Prof. Dr. Sybren S. Wijmenga and Dr. Marco Tessari

      Article first published online: 17 DEC 2014 | DOI: 10.1002/anie.201411678

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      Quantitative trace analysis by NMR spectroscopy is feasible with a nuclear spin hyperpolarization method, namely signal amplification by reversible exchange (SABRE), as described by M. Tessari and co-workers in their Communication on page 1481 ff. SABRE was combined with the standard-addition method to determine concentrations of dilute analytes in complex mixtures.

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      Inside Back Cover: The Reactivities of Iminoboranes with Carbenes: BN Isosteres of Carbene–Alkyne Adducts (Angew. Chem. Int. Ed. 5/2015) (page 1677)

      Prof. Dr. Holger Braunschweig, Dr. William C. Ewing, Dr. K. Geetharani and Marius Schäfer

      Article first published online: 12 DEC 2014 | DOI: 10.1002/anie.201411644

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      The reactions of imino boranes and singlet carbenes display expected as well as unexpected rectivity patterns. In their Communication on page 1662 ff., H. Braunschweig and co-workers report the formation of an iminoborane–carbene Lewis acid–base adduct, an aminoborane-functionalized carbene, and a bicyclic azaborolidine from the reactions of three different carbenes with the same iminoborane.

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      Back Cover: Impact of Pore Connectivity on the Design of Long-Lived Zeolite Catalysts (Angew. Chem. Int. Ed. 5/2015) (page 1678)

      Maria Milina, Dr. Sharon Mitchell, Dr. David Cooke, Dr. Paolo Crivelli and Prof. Javier Pérez-Ramírez

      Article first published online: 12 DEC 2014 | DOI: 10.1002/anie.201411639

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      The unique sensitivity of positron annihilation lifetime spectroscopy to subtleties in the pore connectivity of hierarchically structured MFI zeolites reveals the direct correlation with the catalyst longevity in the conversion of methanol to hydrocarbons, as shown by J. Pérez-Ramírez et al. in their Communication on page 1591 ff. Artwork: concept A. Gallardo, illustration M. Reich.

  2. Frontispiece

    1. Top of page
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    3. Frontispiece
    4. Editorial
    5. Graphical Abstract
    6. Flashback
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    8. Author Profile
    9. Minireview
    10. Review
    11. Communications
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      Frontispiece: Wettability-Regulated Extracellular Electron Transfer from the Living Organism of Shewanella loihica PV-4

      Dr. Chun-mei Ding, Mei-ling Lv, Prof. Ying Zhu, Prof. Lei Jiang and Prof. Huan Liu

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201580561

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      Electron Transfer Extracellular electron transfer from living microbes can be regulated by altering the surface wettability of the electrode. In their Communication on page 1446 ff., H. Liu, Y. Zhu, et al. report that the electron transfer activity on a hydrophilic electrode is more than five times higher than that on a hydrophobic one.

  3. Editorial

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    11. Communications
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  4. Graphical Abstract

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    11. Communications
    1. Graphical Abstract: Angew. Chem. Int. Ed. 5/2015 (pages 1377–1392)

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201590003

  5. Flashback

    1. Top of page
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    4. Editorial
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    10. Review
    11. Communications
    1. 50 Years Ago ... (page 1388)

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201580514

  6. News

    1. Top of page
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    3. Frontispiece
    4. Editorial
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    6. Flashback
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    9. Minireview
    10. Review
    11. Communications
  7. Author Profile

    1. Top of page
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    11. Communications
    1. Chunhai Fan (page 1400)

      Article first published online: 24 SEP 2014 | DOI: 10.1002/anie.201408272

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      “My favorite food is Mongolian-style barbeque lamb. If I won the lottery, I would go traveling. …” This and more about Chunhai Fan can be found on page 1400.

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  8. Minireview

    1. Top of page
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    11. Communications
    1. Symmetry Breaking

      Molecular Chirality in Meteorites and Interstellar Ices, and the Chirality Experiment on Board the ESA Cometary Rosetta Mission (pages 1402–1412)

      Iuliia Myrgorodska, Dr. Cornelia Meinert, Dr. Zita Martins, Dr. Louis Le Sergeant d'Hendecourt and Prof. Dr. Uwe J. Meierhenrich

      Article first published online: 27 NOV 2014 | DOI: 10.1002/anie.201409354

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      Back to where it all began: In November 2014, the Philae lander detached from the Rosetta orbiter to soft-land on the surface of a cometary nucleus. Philae is equipped with a device for the identification of chiral molecules in cometary ices. Crucial insight into the origin of the homochirality of biomolecules is expected (image: ESA/Rosetta/MPS for OSIRIS Team MPS/UPD/LAM/IAA/SSO/INTA/UPM/DASP/IDA).

  9. Review

    1. Top of page
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    11. Communications
    1. Micro- and Nanomotors

      Chemically Powered Micro- and Nanomotors (pages 1414–1444)

      Dr. Samuel Sánchez, Dr. Lluís Soler and Jaideep Katuri

      Article first published online: 12 DEC 2014 | DOI: 10.1002/anie.201406096

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      Moving down in the world: Chemically powered micro- and nanomotors are small devices that are self-propelled by catalytic reactions in fluids. Remotely guided nanomotors can transport cargo to desired targets, drill into biomaterials, sense their environment, mix or pump fluids, and clean polluted water.

  10. Communications

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

      Wettability-Regulated Extracellular Electron Transfer from the Living Organism of Shewanella loihica PV-4 (pages 1446–1451)

      Dr. Chun-mei Ding, Mei-ling Lv, Prof. Ying Zhu, Prof. Lei Jiang and Prof. Huan Liu

      Article first published online: 2 DEC 2014 | DOI: 10.1002/anie.201409163

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      Hydrophobic or hydrophilic: The electron flow from living microbes can be simply regulated by altering the surface wettability of the electrodes at a fixed external potential. The extracellular electron transfer activity on a hydrophilic electrode is shown to be more than five times higher than that on a hydrophobic one. TCA=tricarboxylic acid.

    2. Colloid Chemistry | Very Important Paper

      Emulsion Ripening through Molecular Exchange at Droplet Contacts (pages 1452–1455)

      Dr. Kevin Roger, Prof. Dr. Ulf Olsson, Dr. Ralf Schweins and Dr. Bernard Cabane

      Article first published online: 10 DEC 2014 | DOI: 10.1002/anie.201407858

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      Another pathway for coarsening of emulsion is uncovered, besides coalescence and Ostwald ripening, that is termed contact ripening (top). Its mechanism consists of an exchange of oil molecules during collisions of droplets (middle). The key step is the synchronous thinning of each surfactant layer, through which oil molecules can cross the interface (bottom).

    3. Liquid–Liquid Interfaces

      Particle-Stabilized Water Droplets that Sprout Millimeter-Scale Tubes (pages 1456–1460)

      Miglė Graužinytė, Joe Forth, Katherine A. Rumble and Dr. Paul S. Clegg

      Article first published online: 8 DEC 2014 | DOI: 10.1002/anie.201408365

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      Sprouting droplets: With increasing time, tubes are observed to sprout from water droplets with rigid membranes formed from colloidal particles trapped on the liquid–liquid interface. This is driven by an internal over-pressure which arises as a result of a minority constituent on the outside of the droplet that preferentially partitions into the water inside the membrane.

    4. Bioconjugation

      Targeted Antithrombotic Protein Micelles (pages 1461–1465)

      Dr. Wookhyun Kim, Dr. Carolyn Haller, Dr. Erbin Dai, Xiowei Wang, Dr. Christoph E. Hagemeyer, Prof. David R. Liu, Prof. Karlheinz Peter and Prof. Elliot L. Chaikof

      Article first published online: 10 DEC 2014 | DOI: 10.1002/anie.201408529

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      Site-specific: An activated platelet-specific antibody and antithrombotic protein were site-specifically conjugated to the corona of protein nanomicelles for efficient detection and inhibition of thrombus formation. These multifunctional protein micelles provide a promising approach to the site-specific delivery of a potent antithrombotic agent, thus reducing the dose and bleeding risk. aPC=activated protein C, Th=thrombin.

    5. Cell-Surface Engineering | Hot Paper

      Long-Lived Engineering of Glycans to Direct Stem Cell Fate (pages 1466–1470)

      Abigail Pulsipher, Matthew E. Griffin, Shannon E. Stone and Prof. Linda C. Hsieh-Wilson

      Article first published online: 4 DEC 2014 | DOI: 10.1002/anie.201409258

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      Sweet display: A method for the long-lived presentation of specific glycans on cell surfaces is reported. HaloTag proteins (HTP) were utilized to covalently attach defined heparan sulfate (HS) structures to embryonic stem cell membranes. Highly sulfated HS induced differentiation into neuronal cell types, thus demonstrating the potential of glycan engineering to drive important physiological processes.

    6. Noble Gas Clathrates

      Extreme Confinement of Xenon by Cryptophane-111 in the Solid State (pages 1471–1475)

      Akil I. Joseph, Dr. Saul H. Lapidus, Christopher M. Kane and Prof. K. Travis Holman

      Article first published online: 11 DEC 2014 | DOI: 10.1002/anie.201409415

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      Imprisoning a noble: Xenon gas is effectively imprisoned, at temperatures of up to 300 °C, by a trigonal crystalline phase of the discrete container molecule (±)-cryptophane-111. The seemingly unprecedented kinetic stability of the gas clathrate can be attributed in part to its crystal packing.

    7. Chemical Bonding

      Assessing the Viability of Extended Nonmetal Atom Chains in MnF4n+2 (M=S and Se) (pages 1476–1480)

      Ivan A. Popov, Boris B. Averkiev, Alyona A. Starikova, Prof. Dr. Alexander I. Boldyrev, Prof. Dr. Ruslan M. Minyaev and Prof. Dr. Vladimir I. Minkin

      Article first published online: 4 DEC 2014 | DOI: 10.1002/anie.201409418

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      No end in sight: The viability of extended chains of nonmetal atoms was assessed theoretically on the basis of molecular models MnF4n+2 (M=S or Se, yellow; F turquoise) and corresponding solid-state systems exhibiting direct S[BOND]S or Se[BOND]Se bonding. The proposed molecules were found to be minima for SnF4n+2 systems with n=2–9 and for selenium analogues with n≤6, and the -(SF4–SF4)- structure, unlike -(SeF4–SeF4)-, was found to be dynamically stable.

    8. NMR Spectroscopy | Very Important Paper

      Quantitative Trace Analysis of Complex Mixtures Using SABRE Hyperpolarization (pages 1481–1484)

      Nan Eshuis, Bram J. A. van Weerdenburg, Dr. Martin C. Feiters, Prof. Dr. Floris P. J. T. Rutjes, Prof. Dr. Sybren S. Wijmenga and Dr. Marco Tessari

      Article first published online: 2 DEC 2014 | DOI: 10.1002/anie.201409795

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      Quantitative trace analysis: Nuclear spin hyperpolarization of small molecules in complex mixtures is achieved by signal amplification by reversible exchange (SABRE). The resulting signal enhancements allow quantification of compounds present at low micromolar concentrations in a few single-scan NMR experiments.

    9. Photochemistry

      X-Ray Characterization of an Electron Donor–Acceptor Complex that Drives the Photochemical Alkylation of Indoles (pages 1485–1489)

      Dr. Sandeep R. Kandukuri, Ana Bahamonde, Dr. Indranil Chatterjee, Dr. Igor D. Jurberg, Eduardo C. Escudero-Adán and Prof. Dr. Paolo Melchiorre

      Article first published online: 4 DEC 2014 | DOI: 10.1002/anie.201409529

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      Mutual aid: The electron-rich indole 1 and the electron-accepting bromide 2 readily aggregate to form the photoactive electron donor–acceptor (EDA) complex I. Upon irradiation with light, the alkylation product 3 is formed with high yield (see scheme; CFL=compact fluorescence lamp). The synthetic consequences of this discovery along with the X-ray structure of the relevant EDA complex are discussed.

    10. Lithium-Ion Batteries | Hot Paper

      A Hierarchical Tin/Carbon Composite as an Anode for Lithium-Ion Batteries with a Long Cycle Life (pages 1490–1493)

      Dr. Xingkang Huang, Dr. Shumao Cui, Dr. Jingbo Chang, Peter B. Hallac, Christopher R. Fell, Yanting Luo, Bernhard Metz, Junwei Jiang, Patrick T. Hurley and Prof. Junhong Chen

      Article first published online: 10 DEC 2014 | DOI: 10.1002/anie.201409530

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      High capacity anodes: A tin/carbon hierarchical structure was designed, in which some of the nanosized Sn particles are anchored on the tips of carbon nanotubes that are rooted on the surfaces of microsized hollow carbon cubes while other Sn nanoparticles are encapsulated in the hollow carbon cubes. Such a unique structure allows the Sn particles to accommodate the volume change upon lithiation.

    11. Heterogeneous Catalysis

      Ionic Liquids as Precursors for Efficient Mesoporous Iron-Nitrogen-Doped Oxygen Reduction Electrocatalysts (pages 1494–1498)

      Dr. Zelong Li, Dr. Guanglan Li, Prof. Luhua Jiang, Jinlei Li, Prof. Gongquan Sun, Prof. Chungu Xia and Prof. Fuwei Li

      Article first published online: 10 DEC 2014 | DOI: 10.1002/anie.201409579

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      N-enriched and Fe-embedded ordered mesoporous carbon electrocatalysts were fabricated from an ionic liquid precursor by hard template synthesis. This strategy provides a high surface area and populated Fe-N active sites with synergetic interaction for an optimized Fe10@NOMC catalyst. The catalyst shows excellent electrocatalytic efficiency and durability for the oxygen reduction in alkaline media.

    12. Iron Clusters

      Dinitrogen Activation Upon Reduction of a Triiron(II) Complex (pages 1499–1503)

      Yousoon Lee, Forrest T. Sloane, Dr. Geneviève Blondin, Dr. Khalil A. Abboud, Dr. Ricardo García-Serres and Prof. Dr. Leslie J. Murray

      Article first published online: 11 DEC 2014 | DOI: 10.1002/anie.201409676

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      A trinuclear iron(II) complex, Fe3Br3L in which L is a cyclophane bridged by three β-diketiminate arms, reacts with KC8 under a dinitrogen atmosphere to form complex Fe3(NH)3L among other products. Reactions with 14N2 and 15N2 confirm atmospheric N2 reduction, and ammonia was detected by the indophenol assay. IR and Mössbauer spectroscopy as well as elemental analysis support the assignment that the reduction product contains protonated N-atom bridges.

    13. Single-Molecule Magnets

      Magnetic Memory in an Isotopically Enriched and Magnetically Isolated Mononuclear Dysprosium Complex (pages 1504–1507)

      Dr. Fabrice Pointillart, Dr. Kevin Bernot, Dr. Stéphane Golhen, Dr. Boris Le Guennic, Thierry Guizouarn, Dr. Lahcène Ouahab and Dr. Olivier Cador

      Article first published online: 8 DEC 2014 | DOI: 10.1002/anie.201409887

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      DIY magnetism: The quantum tunneling in a mononuclear Dy-based complex, which already behaves as a single-molecule magnet (SMM), can be drastically reduced, improving the capability of the molecule to store magnetic information. This improvement is brought about by using isotopes of DyIII without a nuclear magnetic moment, thus suppressing the hyperfine interaction, and by dilution of the SMM in a diamagnetic matrix, thus cancelling the internal field.

    14. Molecular Dynamics

      Water-Mediated Recognition of Simple Alkyl Chains by Heart-Type Fatty-Acid-Binding Protein (pages 1508–1511)

      Dr. Shigeru Matsuoka, Dr. Shigeru Sugiyama, Dr. Daisuke Matsuoka, Mika Hirose, Dr. Sébastien Lethu, Hikaru Ano, Dr. Toshiaki Hara, Dr. Osamu Ichihara, Dr. S. Roy Kimura, Dr. Satoshi Murakami, Hanako Ishida, Dr. Eiichi Mizohata, Dr. Tsuyoshi Inoue and Dr. Michio Murata

      Article first published online: 9 DEC 2014 | DOI: 10.1002/anie.201409830

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      Distinguishing fatty acids: The heart-type fatty-acid-binding protein was shown to preferentially incorporate U-shaped fatty acids of C10–C18 by using a chain-length-limiting water cluster. This mechanism was uncovered by ultrahigh-resolution X-ray crystallography as well as energy calculations of the coexisting water molecules with the WaterMap program.

    15. Enzyme Catalysis

      Excited-State Charge Separation in the Photochemical Mechanism of the Light-Driven Enzyme Protochlorophyllide Oxidoreductase (pages 1512–1515)

      Dr. Derren J. Heyes, Dr. Samantha J. O. Hardman, Tobias M. Hedison, Robin Hoeven, Dr. Greg M. Greetham, Prof. Michael Towrie and Prof. Nigel S. Scrutton

      Article first published online: 8 DEC 2014 | DOI: 10.1002/anie.201409881

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      Shining light on enzyme catalysis: Time-resolved spectroscopy has shown how light energy is harnessed to power catalysis in the light-driven enzyme protochlorophyllide oxidoreductase. Excited-state interactions between the enzyme and substrate result in a polarized and highly reactive double bond to trigger a subsequent nucleophilic attack of NADPH.

    16. Redox-Active Ligands

      Redox-Active Ligand-Induced Homolytic Bond Activation (pages 1516–1520)

      Daniël L. J. Broere, Lotte L. Metz, Prof. Dr. Bas de Bruin, Prof. Dr. Joost N. H. Reek, Dr. Maxime A. Siegler and Dr. Jarl Ivar van der Vlugt

      Article first published online: 27 NOV 2014 | DOI: 10.1002/anie.201410048

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      PNO duet: The redox-active pincer ligand PNO, which has a flanking phosphine group, can coordinate to PdII in various oxidation states. One-electron reduction from paramagnetic [PdCl(PNO)] generates a competent reagent for the homolytic bond activation of disulfides through ligand-to-substrate single-electron transfer. The resulting dinuclear Pd species, which has a monothiolate bridgehead, shows well-defined ligand mixed valency in the solid state.

    17. Organoiron Complexes

      Elementary Steps of Iron Catalysis: Exploring the Links between Iron Alkyl and Iron Olefin Complexes for their Relevance in C[BOND]H Activation and C[BOND]C Bond Formation (pages 1521–1526)

      Dr. Alicia Casitas, Helga Krause, Dr. Richard Goddard and Prof. Alois Fürstner

      Article first published online: 10 DEC 2014 | DOI: 10.1002/anie.201410069

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      Trio con brio: Several unorthodox complexes of high relevance for the understanding of iron-catalyzed C–H activation and C–C bond formation have been obtained. These include a surrogate of an intermediate in [2+2+2] cycloaddition reactions, a 14 e [L2Fe(X)R] species that is (meta)stable despite its potential for β-H elimination, and an iron allyl hydride complex formed by two consecutive C–H activation events mediated by a single iron center.

    18. Photochemistry

      The Profound Effect of the Ring Size in the Electrocyclic Opening of Cyclobutene-Fused Bicyclic Systems (pages 1527–1531)

      Michael J. Ralph, Prof. Dr. David C. Harrowven, Dr. Steven Gaulier, Dr. Sean Ng and Prof. Dr. Kevin I. Booker-Milburn

      Article first published online: 5 DEC 2014 | DOI: 10.1002/anie.201410115

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      cis­ or­ trans? The thermal electrocyclic ring opening of a homologous series of [n.2.0]-fused bicyclic systems proceeds via cyclic cis,trans-dienes, in accordance with the Woodward–Hoffmann rules. Highly strained smaller cyclic dienes (≤9 members) undergo isomerization to the stable cis,cis system, while larger cyclic cis,trans dienes (≥10 members) are isolable.

    19. Phase Transitions

      Photoliquefiable Ionic Crystals: A Phase Crossover Approach for Photon Energy Storage Materials with Functional Multiplicity (pages 1532–1536)

      Keita Ishiba, Dr. Masa-aki Morikawa, Chie Chikara, Dr. Teppei Yamada, Katsunori Iwase, Mika Kawakita and Prof. Dr. Nobuo Kimizuka

      Article first published online: 5 DEC 2014 | DOI: 10.1002/anie.201410184

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      Going through a phase: ICs of azobenzene derivatives show a photoinduced IC–IL phase transition (photoliquefaction) upon UV irradiation, and the resulting cis-azobenzene ILs are reversibly photocrystallized by illumination with visible light. The photoliquefaction of ICs is accompanied by a significant increase in ionic conductivity at ambient temperature and holds potential as energy storage materials.

    20. Radical Reactions | Hot Paper

      Decarbonylative Radical Coupling of α-Aminoacyl Tellurides: Single-Step Preparation of γ-Amino and α,β-Diamino Acids and Rapid Synthesis of Gabapentin and Manzacidin A (pages 1537–1541)

      Dr. Masanori Nagatomo, Hayato Nishiyama, Haruka Fujino and Prof. Dr. Masayuki Inoue

      Article first published online: 10 DEC 2014 | DOI: 10.1002/anie.201410186

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      Upon activation by Et3B and O2 at ambient temperature, α-aminoacyl tellurides were readily converted into α-amino carbon radicals through facile decarbonylation, which then reacted intermolecularly with acrylates or glyoxylic oxime ethers to generate various γ-amino and α,β-diamino acids. This mild and powerful coupling method was also applied to the synthesis of gabapentin and the natural product (−)-manzacidin A.

    21. Solid-State NMR Spectroscopy

      A Method for Dynamic Nuclear Polarization Enhancement of Membrane Proteins (pages 1542–1546)

      Adam N. Smith, Dr. Marc A. Caporini, Prof. Gail E. Fanucci and Prof. Joanna R. Long

      Article first published online: 10 DEC 2014 | DOI: 10.1002/anie.201410249

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      Large signal enhancements were observed for a membrane-embedded peptide throughout the lipid bilayer in dynamic nuclear polarization (DNP) magic-angle spinning solid-state NMR experiments when spin-labeled lipids were used as a polarizing agent. The enhancement gradient typically observed with the use of water-soluble biradicals was diminished.

    22. Gas-Phase Ion Chemistry

      Nuclear Magnetic Resonance Structure Elucidation of Peptide b2 Ions (pages 1547–1550)

      Pengyuan Liu, Prof. Dr. R. Graham Cooks and Prof. Dr. Hao Chen

      Article first published online: 10 DEC 2014 | DOI: 10.1002/anie.201410250

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      Fragmentation of peptide ions: Atmospheric pressure thermal dissociation- (APTD) based preparative mass spectrometry was used to collect gas-phase peptide b2 fragments for structural elucidation by NMR spectroscopy. This strategy will be applicable to the elucidation of many difficult fragment ion structures in both fundamental ion chemistry studies and in applied proteomics research.

    23. Drug discovery

      Multidimensional De Novo Design Reveals 5-HT2B Receptor-Selective Ligands (pages 1551–1555)

      Dr. Tiago Rodrigues, Nadine Hauser, Daniel Reker, Dr. Michael Reutlinger, Tiffany Wunderlin, Dr. Jacques Hamon, Dr. Guido Koch and Prof. Dr. Gisbert Schneider

      Article first published online: 4 DEC 2014 | DOI: 10.1002/anie.201410201

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      Multi-objective design: Multidimensional de novo design generated innovative and nanomolar-potent 5-HT2B-selective antagonists. Computational bioaffinity prediction for full target panels and microfluidics-assisted synthesis facilitated their discovery. Our results suggest that such integrated discovery platforms will find further applicability in swift prototyping of drug candidates.

    24. Natural Product Synthesis

      Total Synthesis and Biological Evaluation of the Antibiotic Lysocin E and Its Enantiomeric, Epimeric, and N-Demethylated Analogues (pages 1556–1560)

      Dr. Motoki Murai, Takuya Kaji, Dr. Takefumi Kuranaga, Dr. Hiroshi Hamamoto, Prof. Dr. Kazuhisa Sekimizu and Prof. Dr. Masayuki Inoue

      Article first published online: 11 DEC 2014 | DOI: 10.1002/anie.201410270

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      The antibacterial macrocyclic peptide lysocin E and its enantiomeric, epimeric, and N-demethylated analogues were synthesized by a full solid-phase strategy. Significantly, the antibacterial activity of the unnatural enantiomer was comparable to that of the natural isomer, suggesting the absence of chiral recognition in its mode of action.

    25. Binding Modes in Peptides

      Multi-Frequency, Multi-Technique Pulsed EPR Investigation of the Copper Binding Site of Murine Amyloid β Peptide (pages 1561–1564)

      Donghun Kim, Dr. Jeong Kyu Bang and Dr. Sun Hee Kim

      Article first published online: 10 DEC 2014 | DOI: 10.1002/anie.201410389

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      Pulsed EPR spectroscopy in conjunction with specific isotope labeling was employed to investigate the structure of copper-murine amyloid peptides. This first detailed structural characterization shows that Ala2, Glu3, His6, and His14 are directly coordinated with the copper ion in murine amyloid β peptides at pH 8.5.

    26. C[BOND]H Functionalization

      Direct α-Arylation of Ethers through the Combination of Photoredox-Mediated C[BOND]H Functionalization and the Minisci Reaction (pages 1565–1569)

      Dr. Jian Jin and Prof. Dr. David W. C. MacMillan

      Article first published online: 2 DEC 2014 | DOI: 10.1002/anie.201410432

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      Use visible light! The direct α-arylation of cyclic and acyclic ethers with heteroarenes can be achieved at room temperature through a photoredox-mediated C[BOND]H functionalization pathway. This mild, visible-light-driven protocol allows direct access to medicinal pharmacophores of broad utility using feedstock substrates and a commercial photocatalyst. SET=single-electron transfer.

    27. Phosphorescent Complexes

      Near-IR Phosphorescent Ruthenium(II) and Iridium(III) Perylene Bisimide Metal Complexes (pages 1570–1573)

      Marcus Schulze, Dr. Andreas Steffen and Prof. Dr. Frank Würthner

      Article first published online: 12 DEC 2014 | DOI: 10.1002/anie.201410437

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      The attachment of a ruthenium(II) or iridium(III) metal complex to the perylene core of an azabenzannulated perylene bisimide (ab-PBI) leads to strong phosphorescence out of the PBI triplet state after visible-light absorption. The near-IR phosphorescence of the ruthenium complex has a quantum yield (Φp) of 11 %, which is remarkably high in comparison to other NIR emitters.

    28. Hybrid Materials

      Synergetic Spin Crossover and Fluorescence in One-Dimensional Hybrid Complexes (pages 1574–1577)

      Chun-Feng Wang, Dr. Ren-Fu Li, Prof. Dr. Xue-Yuan Chen, Dr. Rong-Jia Wei, Prof. Dr. Lan-Sun Zheng and Prof. Dr. Jun Tao

      Article first published online: 10 DEC 2014 | DOI: 10.1002/anie.201410454

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      Two hybrid materials assembled from a 1D spin-crossover structure and the fluorophores 1-pyrenecarboxaldehyde and Rhodamine B were prepared. A synergetic effect between spin crossover and fluorescence was proposed.

    29. Drug Discovery

      Multitarget Drug Discovery for Alzheimer's Disease: Triazinones as BACE-1 and GSK-3β Inhibitors (pages 1578–1582)

      Federica Prati, Dr. Angela De Simone, Dr. Paola Bisignano, Dr. Andrea Armirotti, Dr. Maria Summa, Dr. Daniela Pizzirani, Dr. Rita Scarpelli, Dr. Daniel I. Perez, Prof. Dr. Vincenza Andrisano, Dr. Ana Perez-Castillo, Prof. Dr. Barbara Monti, Francesca Massenzio, Dr. Letizia Polito, Prof. Dr. Marco Racchi, Dr. Angelo D. Favia, Dr. Giovanni Bottegoni, Prof. Dr. Ana Martinez, Prof. Dr. Maria Laura Bolognesi and Prof. Dr. Andrea Cavalli

      Article first published online: 11 DEC 2014 | DOI: 10.1002/anie.201410456

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      Two for one: Alzheimer's disease is a complex multifactorial syndrome which calls for the development of multitarget drugs. Accordingly, triazinones are reported here as the first molecule class which is able to simultaneously modulate BACE-1 and GSK-3β activity. Such dual-target inhibitors, by acting against two crucial enzymes in the neurotoxic pathways, might represent a breakthrough in the quest for disease-modifying drugs.

    30. C[BOND]H Activation

      Synthesis of Annelated Phospholes through Intramolecular C[BOND]H Activation by Monovalent Phosphorus (pages 1583–1586)

      Xinda Wei, Zongming Lu, Xu Zhao, Prof. Dr. Zheng Duan and Prof. Dr. Francois Mathey

      Article first published online: 9 DEC 2014 | DOI: 10.1002/anie.201410603

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      Proximity matters: Electrophilic terminal phosphinidene complexes (left, with Ar-Ar being biaryl or an analogue thereof) undergo a spontaneous insertion of the P atom into the vicinal C[BOND]H bond to give annelated phospholes. The latter compounds are valuable precursors for the preparation of a variety of optoelectronic devices.

    31. RNA Modification

      High-Resolution N6-Methyladenosine (m6A) Map Using Photo-Crosslinking-Assisted m6A Sequencing (pages 1587–1590)

      Kai Chen, Zhike Lu, Xiao Wang, Dr. Ye Fu, Dr. Guan-Zheng Luo, Nian Liu, Dr. Dali Han, Dr. Dan Dominissini, Dr. Qing Dai, Prof. Tao Pan and Prof. Chuan He

      Article first published online: 9 DEC 2014 | DOI: 10.1002/anie.201410647

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      Modification sites at N6-methyladenosine (m6A) can be more accurately defined with a photo-crosslinking-assisted m6A sequencing strategy. It was used to obtain a high-resolution map of m6A in a human transcriptome. 4SU=4-thiouridine, IP=immunoprecipitation.

    32. Heterogeneous Catalysis

      Impact of Pore Connectivity on the Design of Long-Lived Zeolite Catalysts (pages 1591–1594)

      Maria Milina, Dr. Sharon Mitchell, Dr. David Cooke, Dr. Paolo Crivelli and Prof. Javier Pérez-Ramírez

      Article first published online: 5 NOV 2014 | DOI: 10.1002/anie.201410016

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      Well connected? The sensitivity of positron annihilation lifetime spectroscopy (PALS) to subtleties in the pore connectivity of hierarchical zeolite catalysts that arise from variations in the synthesis enables rationalization of their distinct lifetime in the conversion of methanol to hydrocarbons (MTH). The findings have huge implications for the manufacturing efficiency and performance of these and other advanced porous materials.

    33. Asymmetric Catalysis

      PyBidine–Cu(OTf)2-Catalyzed Asymmetric [3+2] Cycloaddition with Imino Esters: Harmony of Cu–Lewis Acid and Imidazolidine-NH Hydrogen Bonding in Concerto Catalysis (pages 1595–1599)

      Prof. Dr. Takayoshi Arai, Hiroki Ogawa, Dr. Atsuko Awata, Dr. Makoto Sato, Megumi Watabe and Prof. Dr. Masahiro Yamanaka

      Article first published online: 9 DEC 2014 | DOI: 10.1002/anie.201410782

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      Dual activation system: A bis(imidazolidine)pyridine (PyBidine)–Cu(OTf)2 complex catalyzes the endo-selective [3+2] cycloaddition of methyleneindolinones with imino esters to afford spiro[pyrrolidin-3,3′-oxindole]s in up to 98 % ee. X-ray analysis and DFT calculations suggest that an intermediate Cu enolate of the imino ester reacts with the methyleneindolinone, which is activated by NH-hydrogen bonding with the PyBidine–Cu(OTf)2 catalyst.

    34. Lipids

      Self-Assembly Structure Formation during the Digestion of Human Breast Milk (pages 1600–1603)

      Dr. Stefan Salentinig, Stephanie Phan, Dr. Adrian Hawley and Prof. Ben J. Boyd

      Article first published online: 5 DEC 2014 | DOI: 10.1002/anie.201408320

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      Baby fat: An infant′s complete diet, human breast milk, is the key to its development and survival. The self-assembly of the lipid digestion products inside the breast milk fat droplet drives structure formation with a high internal surface area. The structure formation is necessarily linked to its function as a carrier for poorly water-soluble molecules in the digestive tract of the infant.

    35. Asymmetric Catalysis

      Highly Diastereo- and Enantioselective Palladium-Catalyzed [3+2] Cycloaddition of Vinyl Aziridines and α,β-Unsaturated Ketones (pages 1604–1607)

      Chao-Fan Xu, Bao-Hui Zheng, Jia-Jia Suo, Dr. Chang-Hua Ding and Prof. Dr. Xue-Long Hou

      Article first published online: 10 DEC 2014 | DOI: 10.1002/anie.201409467

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      Ring to ring: The title reaction of vinyl aziridines and alkenes with a single activator was realized. The presence of the substituent on the vinyl group of the vinyl aziridine plays a key role in determining the stereochemical outcome of the reaction. dba=dibenzylidene acetone, Ts=4-toluenesulfonyl.

    36. Catalytic Asymmetric Intramolecular Homologation of Ketones with α-Diazoesters: Synthesis of Cyclic α-Aryl/Alkyl β-Ketoesters (pages 1608–1611)

      Dr. Wei Li, Fei Tan, Xiaoyu Hao, Gang Wang, Yu Tang, Prof. Dr. Xiaohua Liu, Dr. Lili Lin and Prof. Dr. Xiaoming Feng

      Article first published online: 8 DEC 2014 | DOI: 10.1002/anie.201409572

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      A chiral­ N,N′-dioxide–Sc(OTf)3 complex catalyzes the asymmetric intramolecular homologation of simple ketones with α-diazoesters. This method gives access to chiral cyclic α-aryl/alkyl β-ketoesters with an all-carbon quaternary stereocenter. The reaction proceeds under mild reaction conditions through an intramolecular addition/rearrangement process, thereby generating the β-ketoesters in high yield and enantiomeric excess.

    37. [3+2] Cycloaddition Reactions

      Addition of Nitromethane to a Disilene and a Digermene: Comparison to Surface Reactivity and the Facile Formation of 1,3,2-Dioxazolidines (pages 1612–1615)

      Nada Y. Tashkandi, Frederick Parsons, Jiacheng Guo and Prof. Kim M. Baines

      Article first published online: 8 DEC 2014 | DOI: 10.1002/anie.201409707

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      Nitromethane addition to tetramesityldisilene and tetramesityldigermene leads to the formation of 1,3,2,4,5-dioxazadisil- and digermolidine ring systems, respectively. The 1,3,2,4,5-dioxazadisilolidine isomerizes to the 1,4,2,3,5-dioxazadisilolidine ring system, whereas the 1,3,2,4,5-dioxazadigermolidine undergoes ring opening to the isomeric oxime.

    38. Asymmetric Catalysis

      Rhodium-Catalyzed Asymmetric Synthesis of Silicon-Stereogenic Dibenzosiloles by Enantioselective [2+2+2] Cycloaddition (pages 1616–1620)

      Dr. Ryo Shintani, Chihiro Takagi, Tomoaki Ito, Dr. Masanobu Naito and Prof. Dr. Kyoko Nozaki

      Article first published online: 9 DEC 2014 | DOI: 10.1002/anie.201409733

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      Silicon cycles: An axially chiral monophosphine ligand is employed in the Rh-catalyzed reaction between silicon-containing prochiral triynes and internal alkynes to form silicon-stereogenic dibenzosiloles with high yields and enantioselectivities. A germanium-stereogenic dibenzogermole is also prepared by this method.

    39. Rauhut–Currier Reaction

      Highly Enantioselective Intermolecular Cross Rauhut–Currier Reaction Catalyzed by a Multifunctional Lewis Base Catalyst (pages 1621–1624)

      Xuelin Dong, Ling Liang, Erqing Li and Prof. Dr. You Huang

      Article first published online: 9 DEC 2014 | DOI: 10.1002/anie.201409744

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      A cat. with handles: A multifunctional chiral Lewis base catalyst mediates the highly enantioselective intermolecular cross Rauhut–Currier (RC) reaction of different active olefins. The RC products were obtained in excellent yields and high chemo- and enantioselectivity. The reaction could be performed on a gram scale with a catalyst loading of 1 mol %.

    40. Synthetic Methods

      Redox-Neutral α-Allylation of Amines by Combining Palladium Catalysis and Visible-Light Photoredox Catalysis (pages 1625–1628)

      Jun Xuan, Ting-Ting Zeng, Zhu-Jia Feng, Qiao-Hui Deng, Prof. Dr. Jia-Rong Chen, Dr. Liang-Qiu Lu, Prof. Dr. Wen-Jing Xiao and Prof. Dr. Howard Alper

      Article first published online: 10 DEC 2014 | DOI: 10.1002/anie.201409999

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      Double up: The title reaction was accomplished by merging palladium catalysis and visible-light photoredox catalysis. The catalytic generation of an allyl radical from the corresponding π-allylpalladium intermediate was realized without additional metal reducing reagents for the first time. Various α-allylation products of amines were achieved in high yields by radical cross-coupling under mild reaction conditions. SET=single-electron transfer.

    41. Lactone Synthesis

      Intermolecular Dynamic Kinetic Resolution Cooperatively Catalyzed by an N-Heterocyclic Carbene and a Lewis Acid (pages 1629–1633)

      Zijun Wu, Fangyi Li and Prof. Dr. Jian Wang

      Article first published online: 28 NOV 2014 | DOI: 10.1002/anie.201410030

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      Enantioenriched δ-lactones were accessed by an intermolecular dynamic kinetic resolution of β-halo-α-ketoesters in an oxidation/lactonization sequence. The process generates two contiguous stereocenters with remarkable diastereoselectivity through the cooperative catalysis of an N-heterocyclic carbene and a Lewis acid. DQ=3,3′,5,5′-tetra-tert-butyldiphenoquinone (oxidant).

    42. Diradicals

      Nitrogen Analogues of Thiele’s Hydrocarbon (pages 1634–1637)

      Yuanting Su, Dr. Xingyong Wang, Yuantao Li, Prof. You Song, Yunxia Sui and Prof. Xinping Wang

      Article first published online: 11 DEC 2014 | DOI: 10.1002/anie.201410256

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      Dications: A series of bis[N,N-di-(4-methoxylphenyl)amino]arene dications have been synthesized and characterized. It was found that they are singlets in the ground state and that their diradical character is dependent on the bridging moiety. The work provides a nitrogen analogue of Thiele's hydrocarbon with a considerable diradical character.

    43. Asymmetric Synthesis

      Enantioselective Synthesis of α-Aminosilanes by Copper-Catalyzed Hydroamination of Vinylsilanes (pages 1638–1641)

      Nootaree Niljianskul, Dr. Shaolin Zhu and Prof. Dr. Stephen L. Buchwald

      Article first published online: 4 DEC 2014 | DOI: 10.1002/anie.201410326

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      Versatile vinylsilanes: The use of a Cu catalyst, diethoxymethylsilane as a stoichiometric reductant, and O-benzoylhydroxylamines as the electrophilic nitrogen source allows the synthesis of α-aminosilanes. This highly enantio- and regioselective hydroamination reaction is compatible with differentially substituted vinylsilanes, thereby providing access to amino acid mimics and other valuable chiral organosilicon compounds.

    44. Synthetic Methods

      Hydrogen-Borrowing and Interrupted-Hydrogen-Borrowing Reactions of Ketones and Methanol Catalyzed by Iridium (pages 1642–1645)

      Di Shen, Darren L. Poole, Camilla C. Shotton, Anne F. Kornahrens, Dr. Mark P. Healy and Prof. Timothy J. Donohoe

      Article first published online: 9 DEC 2014 | DOI: 10.1002/anie.201410391

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      On loan: [{Ir(cod)Cl}2] facilitates hydrogen-borrowing reactions of ketone enolates with methanol at 65 °C as described. Performing the reaction under an oxygen atmosphere aids the process, and when combined with a bulky monodentate phosphine ligand, interrupts the catalytic cycle by preventing enone reduction. The addition of pro-nucleophiles to the reaction mixture completes a one-pot methylenation/conjugate addition method.

    45. C[BOND]H Activation

      Palladium-Catalyzed Intramolecular C[BOND]H Difluoroalkylation: Synthesis of Substituted 3,3-Difluoro-2-oxindoles (pages 1646–1650)

      Dr. Shi-Liang Shi and Prof. Dr. Stephen L. Buchwald

      Article first published online: 4 DEC 2014 | DOI: 10.1002/anie.201410471

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      Scoped out: An efficient synthesis of the title compounds by a palladium-catalyzed C[BOND]H difluoroalkylation is described. This method features a broad substrate scope, operational simplicity, and utilizes readily available starting materials. BrettPhos was found to facilitate this transformation with unique efficiency. CPME=cyclopentyl methyl ether, dba=dibenzylidene acetone.

    46. Microporous Materials

      Turn-On Luminescence Sensing and Real-Time Detection of Traces of Water in Organic Solvents by a Flexible Metal–Organic Framework (pages 1651–1656)

      Antigoni Douvali, Dr. Athanassios C. Tsipis, Dr. Svetlana V. Eliseeva, Prof. Stéphane Petoud, Dr. Giannis S. Papaefstathiou, Dr. Christos D. Malliakas, Dr. Ioannis Papadas, Dr. Gerasimos S. Armatas, Dr. Irene Margiolaki, Prof. Mercouri G. Kanatzidis, Dr. Theodore Lazarides and Dr. Manolis J. Manos

      Article first published online: 8 DEC 2014 | DOI: 10.1002/anie.201410612

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      Testing the water: A Mg2+ metal–organic framework (MOF) is reported. It has the extraordinary capability to detect, in real time, trace water concentrations (0.05–5 %) in various organic solvents through an unusual turn-on luminescence sensing mechanism. The sensitivity and fast response of this MOF for water, and its reusability, make it one of the most powerful water sensors known.

    47. Heterocycles

      Rhodium(III)-Catalyzed Cyclative Capture Approach to Diverse 1-Aminoindoline Derivatives at Room Temperature (pages 1657–1661)

      Dr. Dongbing Zhao, Suhelen Vásquez-Céspedes and Prof. Dr. Frank Glorius

      Article first published online: 15 DEC 2014 | DOI: 10.1002/anie.201410342

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      Buckle up! The nucleophilic addition of C(sp3)–Rh species to polarized double bonds is the key step in a RhIII-catalyzed C–H activation/cyclative capture reaction. This constitutes the first intermolecular catalytic method to directly access the 1-aminoindoline core with a broad substituent scope under mild conditions (Boc=tert-butoxycarbonyl, DG=directing group).

    48. Iminoborane Adducts

      The Reactivities of Iminoboranes with Carbenes: BN Isosteres of Carbene–Alkyne Adducts (pages 1662–1665)

      Prof. Dr. Holger Braunschweig, Dr. William C. Ewing, Dr. K. Geetharani and Marius Schäfer

      Article first published online: 4 DEC 2014 | DOI: 10.1002/anie.201409699

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      A B in C's clothing: The isolation and characterization of a set of carbene adducts of iminoboranes indicates diverse reactivity patterns. Simple adducts present “boraimine” structures, which mimic the organic imine functionality. Rearrangements of these simple adducts yield backbone-substituted carbenes as well as 1,2-azaborolidines.

    49. Gold Catalysis | Very Important Paper

      CO Extrusion in Homogeneous Gold Catalysis: Reactivity of Gold Acyl Species Generated through Water Addition to Gold Vinylidenes (pages 1666–1670)

      M. Sc. Janina Bucher, B. Sc. Tim Stößer, Dr. Matthias Rudolph, Dr. Frank Rominger and Prof. Dr. A. Stephen K. Hashmi

      Article first published online: 15 DEC 2014 | DOI: 10.1002/anie.201409859

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      Gold acyl intermediates are generated through the addition of water to gold vinylidene intermediates. The hitherto barely known gold acyl species are shown to undergo an extrusion of CO, an elementary step so far unknown in homogeneous gold catalysis. The reaction sequence constitutes a new gold-catalyzed decarbonylative indene synthesis.

    50. Protein Phosporylation | Hot Paper

      Screening for Protein Phosphorylation Using Nanoscale Reactions on Microdroplet Arrays (pages 1671–1675)

      Simon K. Küster, Dr. Martin Pabst, Prof. Renato Zenobi and Prof. Petra S. Dittrich

      Article first published online: 12 DEC 2014 | DOI: 10.1002/anie.201409440

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      Phosphopeptide screening: A mass spectrometry-based screening method detects protein phosphorylation in complex protein mixtures without extensive MS/MS experiments. The method employs droplet microfluidics to integrate nanoliter phosphatase reactions in a nano-LC-MALDI-MS workflow. The selective dephosphorylation of every second LC fraction induces characteristic peak fluctuations that can be used to identify even low-abundant phosphopeptides.

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