Angewandte Chemie International Edition

Cover image for Vol. 53 Issue 34

August 18, 2014

Volume 53, Issue 34

Pages 8791–9093

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. Book Review
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. Cover Picture: [NiFe]Hydrogenase from Citrobacter sp. S-77 Surpasses Platinum as an Electrode for H2 Oxidation Reaction (Angew. Chem. Int. Ed. 34/2014) (page 8791)

      Dr. Takahiro Matsumoto, Shigenobu Eguchi, Dr. Hidetaka Nakai, Prof. Takashi Hibino, Dr. Ki-Seok Yoon and Prof. Seiji Ogo

      Article first published online: 6 JUN 2014 | DOI: 10.1002/anie.201405392

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      The construction of a fuel cell using the [NiFe]hydrogenase (H2ase) S-77 as the hydrogen anode is described by P. Ogo et al. in their Communication on page 8895 ff. The enzyme has a mass activity that is over 600 times greater than that of platinum, is stable to air, and can be recovered after CO poisoning.

    2. Inside Cover: Redox and Anion Exchange Chemistry of a Stibine–Nickel Complex: Writing the L, X, Z Ligand Alphabet with a Single Element (Angew. Chem. Int. Ed. 34/2014) (page 8792)

      James S. Jones, Casey R. Wade and Prof. Dr. François P. Gabbaï

      Article first published online: 13 AUG 2014 | DOI: 10.1002/anie.201405436

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      L, X, and Z are the three letters used for the classification of ligands in coordination chemistry. With phosphines (L), alkyls (X), and boranes (Z) as illustrative examples, the classification of a ligand in either of these three groups is usually defined by the nature of the ligating atom. In their Communication on page 8876 ff., F. P. Gabbaï et al. demonstrate that these three ligand types can be adopted by the same ligating element, in this case antimony.

    3. Inside Back Cover: Reversible Photochemical and Thermal Isomerization of Azaboratabisnorcaradiene to Azaborabenzotropilidene (Angew. Chem. Int. Ed. 34/2014) (page 9095)

      Ying-Li Rao, Dr. Christian Hörl, Prof. Dr. Holger Braunschweig and Prof. Dr. Suning Wang

      Article first published online: 24 JUN 2014 | DOI: 10.1002/anie.201405395

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      The chameleon-like ability of the boron atom to facilitate molecular transformations upon external stimuli has led to the isolation of the first example of azaborabenzotropilidenes. In their Communication on page 9086 ff., H. Braunschweig, S. Wang, et al. also describe the direct observation of an unprecedented photothermal interconversion between azaboratabisnorcaradiene and azaborabenzotropilidene.

    4. Back Cover: Selective Formation and Unusual Reactivity of Tetraarsabicyclo[1.1.0]butane Complexes (Angew. Chem. Int. Ed. 34/2014) (page 9096)

      Dr. Christoph Schwarzmaier, Prof. Dr. Alexey Y. Timoshkin, Dr. Gábor Balázs and Prof. Dr. Manfred Scheer

      Article first published online: 1 JUL 2014 | DOI: 10.1002/anie.201406160

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      White phosphorus and yellow arsenic can be selectively activated with dimeric metal complexes, as described by M. Scheer et al. in their Communication on page 9077 ff. The resulting P4 and As4 butterfly complexes of iron and chromium are unprecedented. Surprisingly, they dimerize after photolytic activation or even at room temperature to afford the first examples of As8 cuneane complexes.

  2. Frontispiece

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. Book Review
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. Frontispiece: Picket-Fence Polythiophene and its Diblock Copolymers that Afford Microphase Separations Comprising a Stacked and an Isolated Polythiophene Ensemble

      Chengjun Pan, Dr. Kazunori Sugiyasu, Dr. Junko Aimi, Akira Sato and Prof. Dr. Masayuki Takeuchi

      Article first published online: 13 AUG 2014 | DOI: 10.1002/anie.201483471

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      K. Sugiyasu, M. Takeuchi, et al. describe microphase separation in polythiophene copolymers with unfunctionalized and “fenced” blocks in their Communication on page 8870 ff. π–π stacking of the unfunctionalized block results in an ensemble of stacked and isolated polythiophenes.

  3. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. Book Review
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. Graphical Abstract: Angew. Chem. Int. Ed. 34/2014 (pages 8795–8809)

      Article first published online: 13 AUG 2014 | DOI: 10.1002/anie.201490032

  4. Corrigenda

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. Book Review
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. You have free access to this content
      Corrigendum: Total Synthesis of (−)-Lycoposerramine-S (page 8808)

      Naoaki Shimada, Dr. Yuzo Abe, Dr. Satoshi Yokoshima and Prof. Tohru Fukuyama

      Article first published online: 13 AUG 2014 | DOI: 10.1002/anie.201311008

      This article corrects:

      Total Synthesis of (−)-Lycoposerramine-S1

      Vol. 51, Issue 47, 11824–11826, Article first published online: 15 OCT 2012

    2. You have free access to this content
      Corrigendum: Total Synthesis of Tryprostatins A and B (page 8808)

      Takayuki Yamakawa, Eiji Ideue, Jun Shimokawa and Prof. Dr. Tohru Fukuyama

      Article first published online: 13 AUG 2014 | DOI: 10.1002/anie.201401055

      This article corrects:

      Total Synthesis of Tryprostatins A and B1

      Vol. 49, Issue 48, 9262–9265, Article first published online: 28 OCT 2010

    3. You have free access to this content
      Corrigendum: Egg White Varnishes on Ancient Paintings: A Molecular Connection to Amyloid Proteins (page 8809)

      Joseph Imbrogno, Dr. Arpan Nayak and Prof. Georges Belfort

      Article first published online: 13 AUG 2014 | DOI: 10.1002/anie.201406368

      This article corrects:

      Egg White Varnishes on Ancient Paintings: A Molecular Connection to Amyloid Proteins1

      Vol. 53, Issue 27, 7014–7017, Article first published online: 18 MAY 2014

  5. News

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

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. Book Review
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. Sergey Troyanov (page 8816)

      Article first published online: 6 MAY 2014 | DOI: 10.1002/anie.201403477

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      “My worst nightmare is to have to stop promising scientific work. The most exciting thing about my research is a lot of wonderful (chemical) surprises …” This and more about Sergey Troyanov can be found on page 8816.

  7. Book Review

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. Book Review
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. Photochemistry and Photophysics. Concepts, Research, Applications. By Vincenzo Balzani, Paola Ceroni and Alberto Juris. (page 8817)

      Xiang Ma and He Tian

      Article first published online: 27 JUL 2014 | DOI: 10.1002/anie.201405219

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      Wiley-VCH, Weinheim, 2014. 504 pp., hardcover, € 72.00.—ISBN 978-3527334797

  8. Highlight

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. Book Review
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. Si[DOUBLE BOND]O Bonds

      A Stable Silanone with a Three-Coordinate Silicon Atom: A Century-Long Wait is Over (pages 8820–8822)

      Dr. Sakya S. Sen

      Article first published online: 2 JUL 2014 | DOI: 10.1002/anie.201404793

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      Mission accomplished: More than 100 years after first attempts at isolating a stable silanone, this task has finally been completed with the isolation of a metallosilanone complex (see Scheme). The elusive bare Si[DOUBLE BOND]O bond was made accessible by utilizing the coordination sphere of an electron-rich chromium fragment in combination with a sterically demanding saturated N-heterocyclic carbene (NHC) to protect the reactive site.

  9. Minireview

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

      Practical Aerobic Oxidations of Alcohols and Amines with Homogeneous Copper/TEMPO and Related Catalyst Systems (pages 8824–8838)

      Bradford L. Ryland and Prof. Shannon S. Stahl

      Article first published online: 7 JUL 2014 | DOI: 10.1002/anie.201403110

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      Coming up for air: Cu/nitroxyl catalysts for aerobic alcohol oxidation have been developed that exhibit near-ideal reaction conditions: operation at room temperature, use of ambient air as the oxidant, and complete reaction within one hour. These methods, together with related amine oxidations, have the potential to be the first class of aerobic oxidation reactions widely used in organic chemistry.

  10. Review

    1. Top of page
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    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. Book Review
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. Antibiotic Development

      The Evolving Role of Chemical Synthesis in Antibacterial Drug Discovery (pages 8840–8869)

      Dr. Peter M. Wright, Dr. Ian B. Seiple and Prof. Dr. Andrew G. Myers

      Article first published online: 2 JUL 2014 | DOI: 10.1002/anie.201310843

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      Chemical synthesis enabled the development of the first antibacterial substances, but these were soon outshone by more powerful antibiotics from nature. Many antibiotics are now significantly less effective due to rapid evolution of resistance within pathogenic bacteria. It is believed that the strategic application of modern synthesis to antibacterial drug discovery can avert a crisis of potentially global proportions.

  11. Communications

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

      Picket-Fence Polythiophene and its Diblock Copolymers that Afford Microphase Separations Comprising a Stacked and an Isolated Polythiophene Ensemble (pages 8870–8875)

      Chengjun Pan, Dr. Kazunori Sugiyasu, Dr. Junko Aimi, Akira Sato and Prof. Dr. Masayuki Takeuchi

      Article first published online: 11 JUN 2014 | DOI: 10.1002/anie.201402813

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      Stack control: All-polythiophene diblock copolymers, comprising one unsheathed block (left) and one fenced block (right), were synthesized through catalyst-transfer polycondensation. The unsheathed block self-assembles through π-π stacking, thereby inducing microphase separation. As a consequence, a microphase separation is created with an ensemble of stacked and isolated polythiophenes.

    2. Coordination Chemistry

      Redox and Anion Exchange Chemistry of a Stibine–Nickel Complex: Writing the L, X, Z Ligand Alphabet with a Single Element (pages 8876–8879)

      James S. Jones, Casey R. Wade and Prof. Dr. François P. Gabbaï

      Article first published online: 20 JUN 2014 | DOI: 10.1002/anie.201404156

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      Pick a letter: A series of redox and anion exchange reactions carried out on a novel SbNi complex can be used to transform the starting stibine ligand (L-type) into a stiboranyl (X-type) and stiborane (Z-type) ligand without dissociation of the coordinated nickel atom (see picture). These results provide the first example of a complex in which the ligating atom can adopt all three ligand functions of the covalent bond classification.

    3. Mesoporous Materials

      Responsive Mesoporous Photonic Cellulose Films by Supramolecular Cotemplating (pages 8880–8884)

      Dr. Michael Giese, Dr. Lina K. Blusch, Dr. Mostofa K. Khan, Dr. Wadood Y. Hamad and Prof. Mark J. MacLachlan

      Article first published online: 30 JUN 2014 | DOI: 10.1002/anie.201402214

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      Eye-catching photonic origami: The invention of a supramolecular cotemplating method led to photonic cellulose material—an active form of “paper” with mesopores and dynamic structural colors. The high flexibility and rapid response upon swelling or pressing of these cellulose-based materials (see picture) make them suitable for applications in pressure or polarity sensing as well as for optical filters.

    4. Drug Discovery

      A LecA Ligand Identified from a Galactoside-Conjugate Array Inhibits Host Cell Invasion by Pseudomonas aeruginosa (pages 8885–8889)

      Dr. Alexandre Novoa, Dr. Thorsten Eierhoff, Dr. Jérémie Topin, Dr. Annabelle Varrot, Dr. Sofia Barluenga, Dr. Anne Imberty, Prof. Winfried Römer and Prof. Nicolas Winssinger

      Article first published online: 7 JUL 2014 | DOI: 10.1002/anie.201402831

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      Optimal combination: Lectin LecA is a pathogenicity factor from P. aeruginosa involved in lung injury and cellular invasion. A novel divalent ligand identified from a focused glycan array binds to LecA with very high affinity and shows a strong inhibition of host cell invasion. Cocrystal structures provided a rationale for its binding affinity.

    5. Heterogeneous Catalysis

      Revealing the Dynamic Structure of Complex Solid Catalysts Using Modulated Excitation X-ray Diffraction (pages 8890–8894)

      Dr. Davide Ferri, Dr. Mark A. Newton, Dr. Marco Di Michiel, Dr. Gian Luca Chiarello, Dr. Songhak Yoon, Dr. Ye Lu and Dr. Jérôme Andrieux

      Article first published online: 5 JUN 2014 | DOI: 10.1002/anie.201403094

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      Take a good look: By combining time-resolved high-energy X-ray diffraction (XRD) with a modulation approach, the sensitivity can be increased so that subtle structural changes during a reaction become visible. Therefore, palladium particles with a diameter of approximately 2 nm could be detected by XRD, and their dynamic behavior under CO/O2 pulses was analyzed.

    6. Fuel Cells

      [NiFe]Hydrogenase from Citrobacter sp. S-77 Surpasses Platinum as an Electrode for H2 Oxidation Reaction (pages 8895–8898)

      Dr. Takahiro Matsumoto, Shigenobu Eguchi, Dr. Hidetaka Nakai, Prof. Takashi Hibino, Dr. Ki-Seok Yoon and Prof. Seiji Ogo

      Article first published online: 4 JUN 2014 | DOI: 10.1002/anie.201404701

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      Outperforming Pt: An electrode for the H2 oxidation reaction is based on [NiFe]Hydrogenase from Citrobacter sp. S-77 ([NiFe]S77). It has a 637 times higher mass activity than Pt at 50 mV in a hydrogen half-cell, is stable in air and, unlike Pt, can be recovered 100 % after poisoning by CO. A fuel cell comprising a [NiFe]S77 anode and Pt cathode was constructed and thus demonstrated a higher power density than that of Pt.

    7. C[BOND]C Bond Cleavage

      Coupling of Titanacyclopentadienes with a Cp Ligand and Elimination of One Substituent (pages 8899–8903)

      Yuki Mizukami, Dr. Haijun Li, Prof. Dr. Kiyohiko Nakajima, Dr. Zhiyi Song and Prof. Dr. Tamotsu Takahashi

      Article first published online: 1 JUL 2014 | DOI: 10.1002/anie.201403226

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      On the trail of the one that got away: 4,5,6-Trisubstituted indene derivatives were formed in good yields by the treatment of titanacyclopentadienes with PMe3 and then azobenzene. The coupling of a Cp ligand with the diene moiety of the complex was accompanied by the removal of one substituent, in sharp contrast to the formation of 4,5,6,7-tetrasubstituted indene derivatives without the loss of a substituent in the absence of PMe3 (see scheme).

    8. Platinum in Zeolites

      A Single-Site Platinum CO Oxidation Catalyst in Zeolite KLTL: Microscopic and Spectroscopic Determination of the Locations of the Platinum Atoms (pages 8904–8907)

      Dr. Joseph D. Kistler, Nutchapon Chotigkrai, Pinghong Xu, Dr. Bryan Enderle, Prof. Dr. Piyasan Praserthdam, Prof. Dr. Cong-Yan Chen, Prof. Dr. Nigel D. Browning and Prof. Dr. Bruce C. Gates

      Article first published online: 1 JUL 2014 | DOI: 10.1002/anie.201403353

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      In the right spot: A site-isolated mononuclear platinum catalyst is supported in the zeolite KLTL with a stable and well-defined structure. This catalyst was examined spectroscopically and imaged with STEM (see picture) to show locations of the platinum complexes (blue circles) within the zeolite pores.

    9. Doping Graphene

      Direct Observation of Atomic Dynamics and Silicon Doping at a Topological Defect in Graphene (pages 8908–8912)

      Dr. Zhiqing Yang, Dr. Lichang Yin, Dr. Jaekwang Lee, Dr. Wencai Ren, Prof. Hui-Ming Cheng, Prof. Hengqiang Ye, Prof. Sokrates T. Pantelides, Prof. Stephen J. Pennycook and Dr. Matthew F. Chisholm

      Article first published online: 30 JUN 2014 | DOI: 10.1002/anie.201403382

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      Atomic competition: The dynamic atomic processes during the formation of a rotary Si trimer in monolayer graphene were monitored using aberration-corrected scanning-transmission electron microscopy. An incoming Si atom competes with and replaces a metastable C dimer next to a pair of Si substitutional atoms at a topological defect in graphene, producing a Si trimer.

    10. Radiolabeling

      A Localized Tolerance in the Substrate Specificity of the Fluorinase Enzyme enables “Last-Step” 18F Fluorination of a RGD Peptide under Ambient Aqueous Conditions (pages 8913–8918)

      Stephen Thompson, Qingzhi Zhang, Mayca Onega, Stephen McMahon, Ian Fleming, Sharon Ashworth, James H. Naismith, Jan Passchier and David O'Hagan

      Article first published online: 2 JUL 2014 | DOI: 10.1002/anie.201403345

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      Leave it 'til the last minute: Direct “last-step” 18F radiolabeling of bioactive peptides is achieved by exploiting an “Achilles heel” in the substrate specificity of the fluorinase enzyme. These isotopically labeled biomolecules can be prepared under ambient pH neutral conditions using aqueous (H218O) cyclotron-generated [18F]fluoride and are suitable for application as tracers in positron emission tomography.

    11. Upconversion Nanoparticles

      Versatile Synthetic Strategy for Coating Upconverting Nanoparticles with Polymer Shells through Localized Photopolymerization by Using the Particles as Internal Light Sources (pages 8919–8923)

      Selim Beyazit, Dr. Serena Ambrosini, Dr. Nataliya Marchyk, Emilia Palo, Vishal Kale, Prof. Tero Soukka, Dr. Bernadette Tse Sum Bui and Prof. Karsten Haupt

      Article first published online: 1 JUL 2014 | DOI: 10.1002/anie.201403576

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      An IRregular initiator: The UV or visible light emitted by photoexcited (by near-infrared light) upconverting nanoparticles (UCPs) was used to photopolymerize a thin polymer coating around the UCPs for their protection, functionalization, and conjugation (see picture). The method has the advantages of ease of application and rapid surface functionalization, and the polymer-encapsulated UCPs are suitable for applications in bioassays, imaging, and drug delivery.

    12. Noncovalent Interactions | Very Important Paper

      Search for a Strong, Virtually “No-Shift” Hydrogen Bond: A Cage Molecule with an Exceptional OH⋅⋅⋅F Interaction (pages 8924–8928)

      Mark D. Struble, Courtney Kelly, Dr. Maxime A. Siegler and Prof. Thomas Lectka

      Article first published online: 2 JUL 2014 | DOI: 10.1002/anie.201403599

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      Close encounters: The spectroscopic properties of a caged fluorine molecule with a strong C[BOND]F⋅⋅⋅H[BOND]O interaction were studied. While computations and NMR data afford evidence for a strong interaction, almost no shift of the OH stretch in the IR spectrum was detected. These data point to a rare no-shift hydrogen bond, in which the bond's red- and blue-shift character cancels.

    13. Nanostructures

      Copper-Based Ternary and Quaternary Semiconductor Nanoplates: Templated Synthesis, Characterization, and Photoelectrochemical Properties (pages 8929–8933)

      Dr. Xue-Jun Wu, Dr. Xiao Huang, Dr. Xiaoying Qi, Dr. Hai Li, Dr. Bing Li and Prof. Dr. Hua Zhang

      Article first published online: 27 JUN 2014 | DOI: 10.1002/anie.201403655

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      Step up to the nanoplate: A facile and general method was used to synthesize monodispersed copper-based ternary and quaternary semiconducting nanoplates (i.e., CuInxGa1−xS2 and Cu2ZnSnS4) with pre-synthesized ultrathin CuS nanoplates as a template. The obtained nanoplates had tunable optical properties, and a photoelectrochemical device based on Cu2ZnSnS4 nanoplates demonstrated promise for photovoltaic devices.

    14. Smart Polyacids

      A Borinic Acid Polymer with Fluoride Ion- and Thermo-responsive Properties that are Tunable over a Wide Temperature Range (pages 8934–8938)

      Dr. Wen-Ming Wan, Dr. Fei Cheng and Prof. Dr. Frieder Jäkle

      Article first published online: 1 JUL 2014 | DOI: 10.1002/anie.201403703

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      Reversibly multi-responsive: A new type of smart polymer with borinic acid moieties has been developed. Polymer PBA has an upper critical solution temperature (UCST) that is tunable from 20 to 100 °C; it also responds to the binding of fluoride to the Lewis acidic boron centers, enabling potential applications in trace water detection and anion recognition.

    15. Crystallization | Hot Paper

      “CLASSIC NMR”: An In-Situ NMR Strategy for Mapping the Time-Evolution of Crystallization Processes by Combined Liquid-State and Solid-State Measurements (pages 8939–8943)

      Dr. Colan E. Hughes, P. Andrew Williams and Prof. Kenneth D. M. Harris

      Article first published online: 7 JUL 2014 | DOI: 10.1002/anie.201404266

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      Killing two birds with one stone: A new in-situ NMR strategy (termed CLASSIC NMR) for mapping the evolution of crystallization processes is reported, involving simultaneous measurement of both liquid-state and solid-state NMR spectra as a function of time. This combined strategy allows complementary information to be obtained on the evolution of the solid phase during the crystallization process as well as the corresponding changes in the solution phase.

    16. Zintl Ions | Hot Paper

      Bi[BOND]Zn Bond Formation in Liquid Ammonia Solution: [Bi[BOND]Zn[BOND]Bi]4−, a Linear Polyanion that is Iso(valence)-electronic to CO2 (pages 8944–8948)

      Christian B. Benda, Tobias Köchner, Raphaela Schäper, Prof. Dr. Stephan Schulz and Prof. Dr. Thomas F. Fässler

      Article first published online: 2 JUL 2014 | DOI: 10.1002/anie.201404343

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      Metallic carbon dioxide: The metal atoms Bi and Zn form two isomers, molecular [Bi[BOND]Zn[BOND]Bi]4− and polymeric equation image{[ZnBi2]4−}, whereas iso(valence)-electronic CO2 and SiS2 adopt only one form under standard conditions. The linear anion [Bi[BOND]Zn[BOND]Bi]4− found in the compound K4[ZnBi2](NH3)12 is formed in the reaction of a low-valent ZnI compound with a solution of the neat solid K3Bi2 in liquid ammonia under mild reaction conditions.

    17. Zeolites

      Intraframework Migration of Tetrahedral Atoms in a Zeolite (pages 8949–8952)

      Dr. Jiho Shin, Nak Ho Ahn, Prof. Miguel A. Camblor, Prof. Sung June Cho and Prof. Suk Bong Hong

      Article first published online: 16 JUN 2014 | DOI: 10.1002/anie.201404379

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      Migration in natrolite: Clear experimental evidence for the intraframework migration of tetrahedral atoms (T-atoms) in natrolite-type zeolites is presented. This process is triggered by species in solution, accompanied by T-atom ordering, and occurs without Ostwald ripening or “classical” dissolution–recrystallization processes. δo=orthorhombic distortion.

    18. Spintronics

      Spin Selectivity in Electron Transfer in Photosystem I (pages 8953–8958)

      Dr. Itai Carmeli, Dr. Karuppannan Senthil Kumar, Omri Heifler, Prof. Chanoch Carmeli and Prof. Ron Naaman

      Article first published online: 2 JUL 2014 | DOI: 10.1002/anie.201404382

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      Unexpected influence: By using a newly developed spintronic device it is shown that the electron transfer (ET) efficiency of photosystem I (PSI) is affected by the electrons' spin. High-spin selectivity is found throughout the entire ET path, and the spins of the electrons being transferred are aligned parallel to their momenta.

    19. Helical Self-Assembly

      Enantioselective Assembly of a Ruthenium(II) Polypyridyl Complex into a Double Helix (pages 8959–8962)

      Prof. Kristof Van Hecke, Dr. Thomas Cardinaels, Dr. Peter Nockemann, Jeroen Jacobs, Louis Vanpraet, Prof. Tatjana N. Parac-Vogt, Prof. Rik Van Deun, Prof. Koen Binnemans and Prof. Luc Van Meervelt

      Article first published online: 7 JUL 2014 | DOI: 10.1002/anie.201404496

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      Unprecedented crystal structures of a ruthenium(II) complex were obtained, showing a left-handed double helical assembly of only the Λ-enantiomer, leading to an alternating tread stairs-like arrangement, which mimics the DNA double helix structure. Two different polymorphs could be distinguished: a crossed woodpile structure versus a parallel columnar stacking.

    20. Sodium-Ion Batteries | Hot Paper

      An Ultrastable Anode for Long-Life Room-Temperature Sodium-Ion Batteries (pages 8963–8969)

      Dr. Haijun Yu, Dr. Yang Ren, Dongdong Xiao, Shaohua Guo, Dr. Yanbei Zhu, Dr. Yumin Qian, Prof. Lin Gu and Prof. Haoshen Zhou

      Article first published online: 24 JUN 2014 | DOI: 10.1002/anie.201404549

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      Cycle stability: When a novel and ultrastable P2-type titanium-based material was used as the anode, a sodium-ion battery with a long cycle life was obtained. A capacity retention of 84.84 % after 3000 cycles and a small volume contraction of only 0.046 % after 500 cycles lead to the outstanding cycle stability.

    21. Dye-Labeled Ts1 toxin | Hot Paper

      Total Chemical Synthesis of Biologically Active Fluorescent Dye-Labeled Ts1 Toxin (pages 8970–8974)

      Bobo Dang, Dr. Tomoya Kubota, Prof. Dr. Ana M. Correa, Prof. Dr. Francisco Bezanilla and Prof. Dr. Stephen B. H. Kent

      Article first published online: 2 JUL 2014 | DOI: 10.1002/anie.201404438

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      Modern ligation methods were used to establish the total chemical synthesis of the Ts1 protein. By using click chemistry the synthetic Ts1 molecule was site-specifically labeled with fluorescent dyes. Dye-labeled Ts1 protein bound to the voltage-gated sodium channel Nav and modified its voltage dependence.

    22. Nanomedicine | Hot Paper

      Development of Multinuclear Polymeric Nanoparticles as Robust Protein Nanocarriers (pages 8975–8979)

      Dr. Jun Wu, Dr. Nazila Kamaly, Dr. Jinjun Shi, Lili Zhao, Dr. Zeyu Xiao, Geoffrey Hollett, Rohit John, Shaunak Ray, Dr. Xiaoyang Xu, Dr. Xueqing Zhang, Prof. Philip W. Kantoff and Prof. Omid C. Farokhzad

      Article first published online: 2 JUL 2014 | DOI: 10.1002/anie.201404766

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      Polymer–polycation nanoparticles have been used as nuclei to readily adsorb large amounts of protein (>20 % of the nanoparticles by weight) to form new hybrid nanospheres with diameters <200 nm in aqueous solutions without organic solvents through electrostatic interactions. This model system was used to demonstrate the relationships between nanosphere size, surface charge, polymer–polycation composition, and protein loading.

    23. Ketenes | Hot Paper

      The Ketene-Surrogate Coupling: Catalytic Conversion of Aryl Iodides into Aryl Ketenes through Ynol Ethers (pages 8980–8984)

      Wenhan Zhang and Dr. Joseph M. Ready

      Article first published online: 27 JUN 2014 | DOI: 10.1002/anie.201405036

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      Setting a trap: Coupling of a terminal ynol ether with aryl iodides enables a catalytic synthesis of aryl ketenes. In situ trapping with nucleophiles provides a wide array of aryl acetic acids and benzyl ketones with only HI and isobutylene as chemical waste. The aryl ketenes additionally participate in electrocyclic ring closure to yield naphthols and quinolines.

    24. Artificial Chaperones

      Maintenance of Amyloid β Peptide Homeostasis by Artificial Chaperones Based on Mixed-Shell Polymeric Micelles (pages 8985–8990)

      Fan Huang, Jianzu Wang, Aoting Qu, Liangliang Shen, Dr. Jinjian Liu, Jianfeng Liu, Dr. Zhenkun Zhang, Yingli An and Prof. Linqi Shi

      Article first published online: 1 JUL 2014 | DOI: 10.1002/anie.201400735

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      Maintaining homeostasis: Mixed-shell polymeric micelles (MSPMs) with tunable surface properties can act as an artificial chaperone. These chaperones can maintain amyloid β (Aβ) homeostasis by inhibiting Aβ fibrillation and facilitating Aβ aggregate clearance, and can also reduce Aβ-mediated neurotoxicity.

    25. Photochemistry | Hot Paper

      [2+2] Cycloaddition of 1,3-Dienes by Visible Light Photocatalysis (pages 8991–8994)

      Anna E. Hurtley, Dr. Zhan Lu and Prof. Tehshik P. Yoon

      Article first published online: 1 JUL 2014 | DOI: 10.1002/anie.201405359

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      Square dance: A convenient and highly functional-group-tolerant [2+2] cycloaddition of 1,3-dienes that operates under visible light irradiation is reported. The vinylcyclobutane products serve as versatile synthetic intermediates in a range of further transformations as illustrated by a concise synthesis of the marine natural product (±)-epiraikovenal. bpy=bipyridyl, ppy=phenylpyridyl.

    26. Reaction Mechanisms

      Insights into the Decomposition of Olefin Metathesis Precatalysts (pages 8995–8999)

      Simone Manzini, Dr. Albert Poater, Dr. David J. Nelson, Prof. Dr. Luigi Cavallo, Prof. Dr. Alexandra M. Z. Slawin and Prof. Dr. Steven P. Nolan

      Article first published online: 2 JUN 2014 | DOI: 10.1002/anie.201403770

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      Ligands make a difference: The decomposition of olefin metathesis precatalysts in isopropyl alcohol leads to a series of differing complexes. Bis(tricyclohexylphosphane)-bearing complexes decompose to yield [RuCl(H)(H2)(PCy3)2], while bis(triphenylphosphane) and bis(iBu-Phoban)-bearing indenylidene complexes yield η5-(3-phenyl)indenyl complexes. The (3-phenyl)indenylidene to η5-indenyl rearrangement for three complexes has been probed using DFT calculations.

    27. Lamellae from Rods | Hot Paper

      “Raft” Formation by Two-Dimensional Self-Assembly of Block Copolymer Rod Micelles in Aqueous Solution (pages 9000–9003)

      Dr. Georgios Rizis, Prof. Theo G. M. van de Ven and Prof. Adi Eisenberg

      Article first published online: 2 JUL 2014 | DOI: 10.1002/anie.201404089

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      A novel mechanism of lamella formation is described, which involves the hierarchical self-assembly of poly(ethylene oxide)-block-polycaprolactone micelles in water. Spheres transform first into rods, which then align spontaneously and associate laterally to form extended lamellar sheets. These self-assembled lamellar “rafts” are thus quite different from the traditional chain-folded crystalline lamellae.

    28. Nanographenes

      From Perylene to a 22-Ring Aromatic Hydrocarbon in One-Pot (pages 9004–9006)

      Bruno Schuler, Sara Collazos, Dr. Leo Gross, Dr. Gerhard Meyer, Dr. Dolores Pérez, Prof. Dr. Enrique Guitián and Dr. Diego Peña

      Article first published online: 1 JUL 2014 | DOI: 10.1002/anie.201403707

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      A threefold symmetric nanographene was synthesized by following a simple procedure based on two sequential aryne cycloadditions in solution starting from perylene. The clover-shaped graphene molecule was characterized with atomic resolution by scanning probe microscopy.

    29. C[BOND]C Coupling

      Copper-Catalyzed Borylative Allyl–Allyl Coupling Reaction (pages 9007–9011)

      Prof. Dr. Kazuhiko Semba, Naoto Bessho, Prof. Dr. Tetsuaki Fujihara, Prof. Dr. Jun Terao and Prof. Dr. Yasushi Tsuji

      Article first published online: 1 JUL 2014 | DOI: 10.1002/anie.201404173

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      All in all: Borylative allyl–allyl coupling using allenes, bis(pinacolato)diboron, and allyl phosphates has been developed in the presence of a copper catalyst bearing an N-heterocyclic carbene (NHC) ligand. The reaction affords boryl-substituted 1,5-diene derivatives in good to high yields with high regioselectivity and Z selectivity.

    30. Natural Product Synthesis

      Bioinspired Total Synthesis of Sespenine (pages 9012–9016)

      Yu Sun, Pengxi Chen, Deliang Zhang, Martin Baunach, Prof. Dr. Christian Hertweck and Prof. Dr. Ang Li

      Article first published online: 24 JUN 2014 | DOI: 10.1002/anie.201404191

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      Being crafty: The first total synthesis of sespenine has been accomplished by using a bioinspired aza-Prins/Friedel–Crafts/retro Friedel–Crafts cascade reaction as the key step.

    31. Cascade Reaction

      Cascade Nitration/Cyclization of 1,7-Enynes with tBuONO and H2O: One-Pot Self-Assembly of Pyrrolo[4,3,2-de]quinolinones (pages 9017–9020)

      Yu Liu, Jia-Ling Zhang, Dr. Ren-Jie Song, Peng-Cheng Qian and Prof. Dr. Jin-Heng Li

      Article first published online: 12 JUN 2014 | DOI: 10.1002/anie.201404192

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      Nitration cascade: The pyrrolo[4,3,2-de]quinolinone scaffold was synthesized by a metal-free reaction of N-(2-(ethynyl)aryl)acrylamides, tert-butyl nitrite and H2O. This cascade reaction is triggered by alkene nitration followed by 1,7-enyne 6-exo-trig cyclization, C[BOND]H nitrations, and redox cyclization and forms the product in good yields.

    32. Reactivity of Diazo Compounds

      A New Reactivity Mode for the Diazo Group: Diastereoselective 1,3-Aminoalkylation Reaction of β-Amino-α-Diazoesters To Give Triazolines (pages 9021–9025)

      Alexey Kuznetsov, Dr. Anton V. Gulevich, Prof. Dr. Donald J. Wink and Prof. Dr. Vladimir Gevorgyan

      Article first published online: 1 JUL 2014 | DOI: 10.1002/anie.201404352

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      Tetrasubstituted 1,2,3-triazolines were synthesized from β-amino-α-diazoesters. This aminoalkylation proceeds through the unusual 1,3-addition of a nucleophile and an electrophile to the diazo group. The reactions exhibit a broad scope and good functional group tolerance as well as excellent diastereoselectivity.

    33. Synthetic Methods

      Lithiation of a Silyl Ether: Formation of an ortho-Fries Hydroxyketone (pages 9026–9029)

      Dr. Hong-Jay Lo, M. Sc. Chin-Yin Lin, Dr. Mei-Chun Tseng and Prof. Rong-Jie Chein

      Article first published online: 27 JUN 2014 | DOI: 10.1002/anie.201404495

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      Me gets a move on: The hydroxy-directed alkylation of an N,N-diethylarylamide through an anionic Si[RIGHTWARDS ARROW]C alkyl migration was developed using a simple reagent combination of LDA (lithium diisopropylamide) and chlorosilane. This reaction was applied to the anionic Snieckus–Fries rearrangement and employed in a highly efficient synthesis of a phosphatidyl-inositol 3-kinase inhibitor.

    34. Carbonylation

      Palladium-Catalyzed Alkoxycarbonylation of Conjugated Dienes under Acid-Free Conditions: Atom-Economic Synthesis of β,γ-Unsaturated Esters (pages 9030–9034)

      Xianjie Fang, Haoquan Li, Dr. Ralf Jackstell and Prof. Dr. Matthias Beller

      Article first published online: 1 JUL 2014 | DOI: 10.1002/anie.201404563

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      Away with acid: A benign palladium-based catalyst system for the alkoxycarbonylation of 1,3-dienes to selectively form β,γ-unsaturated esters under acid-free conditions has been developed. This atom-efficient process is demonstrated in the straightforward synthesis of adipates from 1,3-butadiene.

    35. Mesoporous Materials

      Highly Ordered Mesoporous Tungsten Oxides with a Large Pore Size and Crystalline Framework for H2S Sensing (pages 9035–9040)

      Yuhui Li, Wei Luo, Nan Qin, Dr. Junping Dong, Jing Wei, Wei Li, Shanshan Feng, Junchen Chen, Prof. Dr. Jiaqiang Xu, Dr. Ahmed A. Elzatahry, Dr. Mahir H. Es-Saheb, Prof. Dr. Yonghui Deng and Prof. Dr. Dongyuan Zhao

      Article first published online: 2 JUL 2014 | DOI: 10.1002/anie.201403817

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      Good sense: Ordered mesoporous WO3 materials with a crystalline framework and large pore size (ca. 11 nm) were synthesized by a template-carbonization strategy by using a high-molecular weight amphiphilic block copolymer as the structure-directing agent. The materials exhibit excellent performance for H2S gas sensing.

    36. Lithium Storage | Very Important Paper

      General Synthesis of Multi-Shelled Mixed Metal Oxide Hollow Spheres with Superior Lithium Storage Properties (pages 9041–9044)

      Dr. Genqiang Zhang and Prof. Xiong Wen (David) Lou

      Article first published online: 24 JUN 2014 | DOI: 10.1002/anie.201404604

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      Three steps and you're there: A general “penetration–solidification–annealing” method was developed to synthesize multi-shelled hollows spheres of CoxMn2−xO4 with controllable Co/Mn molar ratios. The method can be easily extended to the synthesis of other mixed metal oxide spheres, such as ZnMn2O4, ZnCo2O4 and NiCo2O4. The carbon-coated CoMn2O4 triple-shelled spheres exhibit excellent lithium storage properties with nearly 100 % capacity retention after 200 cycles.

    37. Catalytic DNA

      DNA-Catalyzed Lysine Side Chain Modification (pages 9045–9050)

      Benjamin M. Brandsen, Tania E. Velez, Dr. Amit Sachdeva, Nora A. Ibrahim and Prof. Scott K. Silverman

      Article first published online: 30 JUN 2014 | DOI: 10.1002/anie.201404622

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      The trick for nitrogen: DNA-catalyzed modification of the lysine (Lys) side chain is achieved. The key to success is the provision of a rather reactive electrophile, 5′-phosphorimidazolide (5′-Imp; see figure). This approach is effective even without preorganization of the two substrates.

    38. Glycopeptide Synthesis

      Chemical Synthesis of Syndecan-3 Glycopeptides Bearing Two Heparan Sulfate Glycan Chains (pages 9051–9058)

      Keisuke Yoshida, Bo Yang, Weizhun Yang, Zeren Zhang, Jicheng Zhang and Xuefei Huang

      Article first published online: 30 JUN 2014 | DOI: 10.1002/anie.201404625

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      Sweet peptides: The large size and tremendous structural complexity of glycosaminoglycan family glycopeptides poses many challenges for their synthesis. A successful strategy for the synthesis of a syndecan-3 glycopeptide (see chemical formula) was established by constructing the partially deprotected single glycan chain containing glycopeptides first, followed by union of the glycan-bearing fragments and cleavage of the ester-type protecting groups.

    39. Heterogeneous Catalysis | Hot Paper

      Trinuclear Gold Clusters Supported by Cyclic (alkyl)(amino)carbene Ligands: Mimics for Gold Heterogeneous Catalysts (pages 9059–9063)

      Dr. Liqun Jin, David S. Weinberger, Dr. Mohand Melaimi, Dr. Curtis E. Moore, Prof. Arnold L. Rheingold and Prof. Guy Bertrand

      Article first published online: 1 JUL 2014 | DOI: 10.1002/anie.201404665

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      Well-defined clusters supported by three cyclic (alkyl)(amino)carbenes (CAACs), or two CAACs and a phosphine, can be prepared by ligand exchange. These mixed-valence gold(I)/gold(0) clusters promote the catalytic carbonylation of amines by the formation of di- or trinuclear gold(I) complexes, which can be isolated.

    40. C[BOND]H Activation | Hot Paper

      Access to β-Lactams by Enantioselective Palladium(0)-Catalyzed C(sp3)[BOND]H Alkylation (pages 9064–9067)

      Julia Pedroni, Michele Boghi, Dr. Tanguy Saget and Prof. Dr. Nicolai Cramer

      Article first published online: 1 JUL 2014 | DOI: 10.1002/anie.201405508

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      Strain away: Chiral β-lactams are obtained from readily accessible chloroacetamides by an asymmetric palladium(II)-catalyzed C[BOND]H functionalization in high yields and excellent enantioselectivities. Important aspects of this transformation are the challenging strain-building C(sp3)[BOND]C(sp3) reductive elimination to form the four-membered ring. Ad=adamanyl.

    41. P,N Ligands

      Facile Synthesis of Phosphaamidines and Phosphaamidinates using Nitrilium Ions as an Imine Synthon (pages 9068–9071)

      Tom van Dijk, Dr. Sebastian Burck, Mark K. Rong, Amos J. Rosenthal, Dr. Martin Nieger, Dr. J. Chris Slootweg and Prof. Dr. Koop Lammertsma

      Article first published online: 27 JUN 2014 | DOI: 10.1002/anie.201405027

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      P bridges: Readily accessible nitrilium triflates are convenient imine building blocks for the expedient synthesis of phosphaamidines as demonstrated for the reaction with primary phosphanes (see Scheme). Lithiation of these species provides access to phosphaamidinates, of which the coordination to [AuCl(tht)] gives a unique P-bridged gold trimer, while [{RhCl(cod)}2] gives bidentate coordination. cod=1,5-cyclooctadiene, tht=tetrahydrothiophene.

    42. Synthetic Methods

      Regiocontrolled Gold-Catalyzed [2+2+2] Cycloadditions of Ynamides with Two Discrete Nitriles to Construct 4-Aminopyrimidine Cores (pages 9072–9076)

      Somnath Narayan Karad and Prof. Dr. Rai-Shung Liu

      Article first published online: 2 JUL 2014 | DOI: 10.1002/anie.201405312

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      In addition: A novel gold-catalyzed intermolecular [2+2+2] cycloaddition of ynamides with two discrete nitriles leads to monomeric 4-aminopyrimidines. The utility of this cycloaddition is demonstrated by the excellent regioselectivity obtained by using a variety of ynamides and nitriles. DCE=1,2-dichloroethane, EWG=electron-withdrawing group.

    43. As4 Activation

      Selective Formation and Unusual Reactivity of Tetraarsabicyclo[1.1.0]butane Complexes (pages 9077–9081)

      Dr. Christoph Schwarzmaier, Prof. Dr. Alexey Y. Timoshkin, Dr. Gábor Balázs and Prof. Dr. Manfred Scheer

      Article first published online: 13 AUG 2014 | DOI: 10.1002/anie.201404653

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      As a butterfly: The selective formation of the dinuclear butterfly complexes [{Cp′′′Fe(CO)2}2(μ,η1:1-E4)] and [{Cp*Cr(CO)3}2(μ,η1:1-E4)] (E=P, As) results from the reaction of E4 with the corresponding dimeric carbonyl complexes. The As complexes are the first As4 butterfly compounds with a bridging coordination mode. First studies of their reactivity show the formation of unprecedented As8 cuneane complexes.

    44. Cumulenes | Hot Paper

      Diborabutatriene: An Electron-Deficient Cumulene (pages 9082–9085)

      Julian Böhnke, Prof. Dr. Holger Braunschweig, Dr. William C. Ewing, Dr. Christian Hörl, Thomas Kramer, Dr. Ivo Krummenacher, Dr. Jan Mies and Dr. Alfredo Vargas

      Article first published online: 23 MAY 2014 | DOI: 10.1002/anie.201403888

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      The use of π-acidic carbenes as stabilizing ligands on a central diboron unit has enabled the synthesis and characterization of a diborabutatriene, an inorganic/organic electron-deficient cumulene with a linear CBBC core. Structural characterization, theoretical analysis, and electrochemical investigation each indicated even sharing of electrons across the four-membered center.

    45. Photoisomerization

      Reversible Photochemical and Thermal Isomerization of Azaboratabisnorcaradiene to Azaborabenzotropilidene (pages 9086–9089)

      Ying-Li Rao, Dr. Christian Hörl, Prof. Dr. Holger Braunschweig and Prof. Dr. Suning Wang

      Article first published online: 18 JUN 2014 | DOI: 10.1002/anie.201404435

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      Boron chameleon: The exceptional ability of the boron atom to facilitate molecular transformations upon external stimuli has led to the isolation of the first example of azaborabenzotropilidenes and the direct observation of an unprecedented photothermal interconversion between azaboratabisnorcaradiene and azaborabenzotropilidene.

    46. Helical Packing

      Helical Packing of Nanoparticles Confined in Cylindrical Domains of a Self-Assembled Block Copolymer Structure (pages 9090–9093)

      Sunita Sanwaria, Dr. Andriy Horechyy, Dr. Daniel Wolf, Dr. Che-Yi Chu, Prof. Dr. Hsin-Lung Chen, Dr. Petr Formanek, Prof. Dr. Manfred Stamm, Prof. Dr. Rajiv Srivastava and Prof. Dr. Bhanu Nandan

      Article first published online: 2 JUL 2014 | DOI: 10.1002/anie.201403565

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      Packing makes coated screws: Silver nanoparticles confined in the self-assembled cylindrical domains of polystyrene-block-poly(4-vinylpyridine) (PS-b-P4VP) pack in an interesting helical morphology. This observation opens up possibilities for the discovery of novel hierarchical structures in such composite systems and also provides new opportunities for the application of such materials in nanotechnology.

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