Angewandte Chemie International Edition

Cover image for Vol. 53 Issue 20

May 12, 2014

Volume 53, Issue 20

Pages 4979–5213

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlight
    11. Review
    12. Communications
    1. You have free access to this content
      Cover Picture: Metal- and Reagent-Free Highly Selective Anodic Cross-Coupling Reaction of Phenols (Angew. Chem. Int. Ed. 20/2014) (page 4979)

      Bernd Elsler, Dr. Dieter Schollmeyer, Dr. Katrin Marie Dyballa, Prof. Dr. Robert Franke and Prof. Dr. Siegfried R. Waldvogel

      Article first published online: 11 APR 2014 | DOI: 10.1002/anie.201401136

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      Neither leaving groups nor catalysts are required for the electrochemical phenol–phenol cross-coupling reaction that is described by S. Waldvogel et al. in their Communication on page 5210 ff. The key to this sustainable synthetic method is the combination of diamond electrodes and a solvent mixture that exhibits an unusual capability of hydrogen bonding. The desired nonsymmetric 2,2′-biphenols could be constructed from simple substrates without the generation of reagent waste.

    2. You have free access to this content
      Inside Cover: Asymmetric Catalysis on the Nanoscale: The Organocatalytic Approach to Helicenes (Angew. Chem. Int. Ed. 20/2014) (page 4980)

      Lisa Kötzner, Dr. Matthew J. Webber, Dr. Alberto Martínez, Dr. Claudia De Fusco and Prof. Dr. Benjamin List

      Article first published online: 23 APR 2014 | DOI: 10.1002/anie.201401125

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      The asymmetric synthesis of helicenes by a Fischer indolization catalyzed by a SPINOL-derived phosphoric acid is reported by B. List et al. in their Communication on page 5202 ff. The catalyst is designed for long-range control and bears extended π-surfaces at the 3,3′-position. It creates a chiral nanometer-sized pocket, which enables π–π stacking interactions between the substituents and the reactive intermediate. A variety of (di)azahelicenes were obtained with good to excellent yields and enentioselectivities.

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      Inside Back Cover: Programmable Polymer-Based Supramolecular Temperature Sensor with a Memory Function (Angew. Chem. Int. Ed. 20/2014) (page 5215)

      Léna Sambe, Victor R. de La Rosa, Khaled Belal, Dr. François Stoffelbach, Dr. Joel Lyskawa, Dr. François Delattre, Marc Bria, Prof. Graeme Cooke, Prof. Richard Hoogenboom and Prof. Patrice Woisel

      Article first published online: 11 APR 2014 | DOI: 10.1002/anie.201403560

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      The heat was on! In their Communication on page 5044 ff., P. Woisel, R. Hoogenboom, G. Cooke et al. describe the supramolecular host–guest interactions between a poly(N-isopropylacrylamide) copolymer with naphthalene side chains and the tetracationic macrocycle cyclobis(paraquat-p-phenylene), which enabled the development of a (re)programmable thermometer that memorizes the thermal history of the solution and provides an associated visible readout.

    4. You have free access to this content
      Back Cover: Phenotypic Screening to Identify Small-Molecule Enhancers for Glucose Uptake: Target Identification and Rational Optimization of Their Efficacy (Angew. Chem. Int. Ed. 20/2014) (page 5216)

      Dr. Minseob Koh, Dr. Jongmin Park, Ja Young Koo, Donghyun Lim, Dr. Mi Young Cha, Ala Jo, Prof. Dr. Jang Hyun Choi and Prof. Dr. Seung Bum Park

      Article first published online: 1 APR 2014 | DOI: 10.1002/anie.201401129

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      The phenotype-based discovery of novel therapeutic agents has suffered from the lengthy process of target deconvolution. In their Communication on page 5102 ff., S. B. Park et al. show that the convergent strategy of phenotype screening with early stage target identification can bridge the gap between phenotype-based hit discovery and rational drug discovery to generate a new class of therapeutic agents. They were able to identify a new small-molecule enhancer of cellular glucose uptake that targets PPARγ.

  2. Frontispiece

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlight
    11. Review
    12. Communications
    1. You have free access to this content
      Frontispiece: Point Decoration of Silicon Nanowires: An Approach Toward Single-Molecule Electrical Detection

      Jindong Wang, Fangxia Shen, Zhenxing Wang, Gen He, Jinwen Qin, Nongyi Cheng, Prof. Maosheng Yao, Prof. Lidong Li and Prof. Xuefeng Guo

      Article first published online: 8 MAY 2014 | DOI: 10.1002/anie.201482071

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      The real-time, label-free biodetection of H1N1 viruses with single-molecule sensitivity by using Si nanowires as local reporters in combination with microfluidics is presented by M. Yao, L. Li, X. Guo et al. in their Communication on pp. 5038 ff.

  3. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlight
    11. Review
    12. Communications
    1. Graphical Abstract: Angew. Chem. Int. Ed. 20/2014 (pages 4983–4994)

      Article first published online: 8 MAY 2014 | DOI: 10.1002/anie.201490018

  4. Corrigenda

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlight
    11. Review
    12. Communications
    1. You have free access to this content
      Corrigendum: A Photocleavable Masked Nuclear-Receptor Ligand Enables Temporal Control of C. elegans Development (page 4994)

      M. Sc. Joshua C. Judkins, Dr. Parag Mahanti, Jacob B. Hoffman, Isaiah Yim, Prof. Dr. Adam Antebi and Prof. Dr. Frank C. Schroeder

      Article first published online: 8 MAY 2014 | DOI: 10.1002/anie.201402230

      This article corrects:

      A Photocleavable Masked Nuclear-Receptor Ligand Enables Temporal Control of C. elegans Development1

      Vol. 53, Issue 8, 2110–2113, Article first published online: 22 JAN 2014

    2. You have free access to this content
      Corrigendum: A Chimeric Siderophore Halts Swarming Vibrio (page 4994)

      Dr. Thomas Böttcher and Prof. Dr. Jon Clardy

      Article first published online: 8 MAY 2014 | DOI: 10.1002/anie.201403617

      This article corrects:

      A Chimeric Siderophore Halts Swarming Vibrio1

      Vol. 53, Issue 13, 3510–3513, Article first published online: 24 FEB 2014

  5. News

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlight
    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. News
    9. Book Review
    10. Highlight
    11. Review
    12. Communications
    1. Jan J. Weigand (page 5002)

      Article first published online: 30 JAN 2014 | DOI: 10.1002/anie.201311108

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      “My favorite saying is ‘Easy’ doesn't enter into grown-up life”. I admire prudence …” This and more about Jan J. Weigand can be found on page 5002.

  7. News

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

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlight
    11. Review
    12. Communications
    1. What is Chemistry? By Peter Atkins. (pages 5004–5005)

      Sason Shaik

      Article first published online: 26 MAR 2014 | DOI: 10.1002/anie.201400523

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      Oxford University Press, Oxford, 2013. 144 pp., hardcover, £ 11.99.—ISBN 978-0199683987

  9. Highlight

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

      Snapshot of Antidepressants at Work: The Structure of Neurotransmitter Transporter Proteins (pages 5008–5009)

      Dr. Serena Cuboni and Dr. Felix Hausch

      Article first published online: 11 APR 2014 | DOI: 10.1002/anie.201310567

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      In the sweet spot: Cocrystal structures of engineered neurotransmitter transporters reveal the binding mode of commonly prescribed antidepressants, providing a basis for a rational drug design for this class of proteins. The picture shows the structure of the dopamine transporter of Drosophila melanogaster in complex with the antidepressant nortriptyline.

  10. Review

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

      C[BOND]H Bond Functionalization through Intramolecular Hydride Transfer (pages 5010–5036)

      Michael C. Haibach and Prof. Dr. Daniel Seidel

      Article first published online: 6 APR 2014 | DOI: 10.1002/anie.201306489

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      Known for over a century, reactions based on intramolecular hydride transfer have experienced a recent resurgence. Hydride shifts represent an attractive avenue for C[BOND]H bond functionalization and the redox-neutral nature of these transformations makes them ideal for the development of sustainable reactions. This Review summarizes recent progress in this field and highlights key historical contributions.

  11. Communications

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

      Point Decoration of Silicon Nanowires: An Approach Toward Single-Molecule Electrical Detection (pages 5038–5043)

      Jindong Wang, Fangxia Shen, Zhenxing Wang, Gen He, Jinwen Qin, Nongyi Cheng, Prof. Maosheng Yao, Prof. Lidong Li and Prof. Xuefeng Guo

      Article first published online: 25 MAR 2014 | DOI: 10.1002/anie.201309438

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      A bioassay design involving lithographically integrating point scattering sites into electrical circuits is capable of realizing real-time, label-free biodetection of H1N1 viruses with single-molecule sensitivity and high selectivity by using Si nanowires as local reporters in combination with microfluidics. This architecture is complementary to conventional optical techniques but has the advantages of no bleaching or fluorescent labeling.

    2. Polymeric Thermometers

      Programmable Polymer-Based Supramolecular Temperature Sensor with a Memory Function (pages 5044–5048)

      Léna Sambe, Victor R. de La Rosa, Khaled Belal, Dr. François Stoffelbach, Dr. Joel Lyskawa, Dr. François Delattre, Marc Bria, Prof. Graeme Cooke, Prof. Richard Hoogenboom and Prof. Patrice Woisel

      Article first published online: 7 APR 2014 | DOI: 10.1002/anie.201402108

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      A polymeric thermometer with a visual read-out is based on the supramolecular interaction between a poly(N-isopropylacrylamide) copolymer with naphthalene side chains and the tetracationic macrocycle cyclobis(paraquat-p-phenylene) tetrachloride. This supramolecular thermometer is (re)programmable and exhibits a memory for the thermal history of the solution.

    3. Biomimetic Nanocomposites

      Molecular Engineering of Fracture Energy Dissipating Sacrificial Bonds Into Cellulose Nanocrystal Nanocomposites (pages 5049–5053)

      Jason R. McKee, Johannes Huokuna, Lahja Martikainen, Mikko Karesoja, Dr. Antti Nykänen, Dr. Eero Kontturi, Prof. Heikki Tenhu, Prof. Janne Ruokolainen and Prof. Olli Ikkala

      Article first published online: 6 APR 2014 | DOI: 10.1002/anie.201401072

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      One-component nanocomposites involving colloidal nanorod cores bound together by polymeric grafts containing a set of supramolecular binding units were fabricated (see picture). This architecture demonstrates fracture energy dissipation for tough biomimetic materials.

    4. Multiplex Detection

      Plasmonic Liquid Marbles: A Miniature Substrate-less SERS Platform for Quantitative and Multiplex Ultratrace Molecular Detection (pages 5054–5058)

      Hiang Kwee Lee, Dr. Yih Hong Lee, Dr. In Yee Phang, Jiaqi Wei, Yue-E Miao, Prof. Tianxi Liu and Prof. Xing Yi Ling

      Article first published online: 1 APR 2014 | DOI: 10.1002/anie.201401026

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      Taking all the marbles: Plasmonic liquid marbles are used in conjunction with surface-enhanced Raman spectroscopy for the simultaneous multiplex quantification and identification of ultratrace analytes across separate phases (see picture) with a detection limit as low as 0.3 fmol, which corresponds to an analytical enhancement factor of 5×108. The results quantitatively tally with those obtained for the individual detection of the analytes.

    5. Nanocomposites

      Doubling the Capacity of Lithium Manganese Oxide Spinel by a Flexible Skinny Graphitic Layer (pages 5059–5063)

      Dr. Hyun Kuk Noh, Han-Saem Park, Prof. Hu Young Jeong, Prof. Sang Uck Lee and Prof. Hyun-Kon Song

      Article first published online: 6 APR 2014 | DOI: 10.1002/anie.201400490

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      Electroactive materials: By coating nanoparticular lithium manganese oxide (LMO) with a few graphitic layers (see picture; d=distance, h=height), the capacity of the material reached up to 220 mA h g−1 at a cutoff voltage of 2.5 V. The graphitic layers provided an electron-transfer highway without hindering ion access and stabilized the structural distortion in the 3 V region.

    6. Molecular Ferroelectrics

      A Molecular Ferroelectric Thin Film of Imidazolium Perchlorate That Shows Superior Electromechanical Coupling (pages 5064–5068)

      Dr. Yi Zhang, Prof. Yuanming Liu, Dr. Heng-Yun Ye, Dr. Da-Wei Fu, Wenxiu Gao, He Ma, Prof. Zhiguo Liu, Prof. Yunya Liu, Prof. Wen Zhang, Prof. Jiangyu Li, Prof. Guo-Liang Yuan and Prof. Ren-Gen Xiong

      Article first published online: 1 APR 2014 | DOI: 10.1002/anie.201400348

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      Molecular ferroelectric thin films and block crystals along crystal face (10equation image) of imidazolium perchlorate display perfect hexagonal domains similar to that of the trigonal crystal system LiNbO3. The high spontaneous polarization, high Curie temperature, low coercivity, and superior electromechanical coupling make it a molecular alternative to perovskite ferroelectric films.

    7. Protein NMR Spectroscopy

      Structural Mapping of a Chaperone–Substrate Interaction Surface (pages 5069–5072)

      Morgane Callon, Dr. Björn M. Burmann and Prof. Dr. Sebastian Hiller

      Article first published online: 2 APR 2014 | DOI: 10.1002/anie.201310963

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      Measurements of intermolecular NOEs between a well-folded chaperone molecule and its unfolded substrate ensemble permit determination of the interaction surface at the atomic level. Resolution of the peaks is enabled by a specialized isotope-labeling scheme for the two proteins. The approach is demonstrated on the Skp–tOmpA complex.

    8. Chiral Amplification

      Autoamplification of Molecular Chirality through the Induction of Supramolecular Chirality (pages 5073–5077)

      Derk Jan van Dijken, Dr. John M. Beierle, Dr. Marc C. A. Stuart, Dr. Wiktor Szymański, Prof. Dr. Wesley R. Browne and Prof. Dr. Ben L. Feringa

      Article first published online: 23 FEB 2014 | DOI: 10.1002/anie.201311160

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      There and back again: Doping a mixture of rapidly interconverting prochiral, open diarylethenes (left) with their enantiopure, closed counterparts, led to formation of gel fibers of preferred helicity (center). This supramolecular chirality was transferred to the molecular level by photochemical ring closing, thus yielding a chiral product (right) which is enriched in the enantiomer originally used as a template.

    9. Alkene Difunctionalization

      Arylphosphonylation and Arylazidation of Activated Alkenes (pages 5078–5082)

      Dr. Wangqing Kong, Dr. Estíbaliz Merino and Prof. Dr. Cristina Nevado

      Article first published online: 1 APR 2014 | DOI: 10.1002/anie.201311241

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      Radical difunctionalization: The addition of heteroatom-centered radicals to the double bond of arylsulfonyl acrylamides furnishes alkyl radical intermediates. A reaction cascade is then triggered so that α-aryl-β-heterofunctionalized amides with a quaternary stereocenter are obtained by the simultaneous formation of C[BOND]C and C[BOND]P/C[BOND]N bonds across the double bond. Heterofunctionalized oxindoles can also be synthesized.

    10. Nanostructures

      Two-Dimensional CuSe Nanosheets with Microscale Lateral Size: Synthesis and Template-Assisted Phase Transformation (pages 5083–5087)

      Dr. Xue-Jun Wu, Dr. Xiao Huang, Dr. Juqing Liu, Dr. Hai Li, Jian Yang, Dr. Bing Li, Prof. Dr. Wei Huang and Prof. Dr. Hua Zhang

      Article first published online: 7 APR 2014 | DOI: 10.1002/anie.201311309

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      Not fazed by change: A facile solution-based strategy was used for the preparation of microsized CuSe nanosheets. As-prepared CuSe with a hexagonal phase was transformed into Cu2−xSe with a cubic phase through simple treatment with heat without damaging the shape of the original 2D nanosheets (see picture). The two kinds of nanosheets show different optical properties and are both promising building blocks for the construction of various devices.

    11. Mechanobiochemistry

      Mechanically Modulating the Photophysical Properties of Fluorescent Protein Biocomposites for Ratio- and Intensiometric Sensors (pages 5088–5092)

      Johnathan N. Brantley, Constance B. Bailey, Joe R. Cannon, Katie A. Clark, Prof. David A. Vanden Bout, Prof. Jennifer S. Brodbelt, Prof. Adrian T. Keatinge-Clay and Prof. Christopher W. Bielawski

      Article first published online: 8 APR 2014 | DOI: 10.1002/anie.201306988

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      Under pressure: Poly(methyl methacrylate) composites containing either enhanced yellow fluorescent protein (eYFP) or genetically modified green fluorescent protein (GFP; see scheme) exhibited changes in photophysical properties under pressure. Whereas the eYFP composites functioned as ratiometric sensors through shifts in their fluorescence emission wavelengths, the GFP composites were intensiometric and underwent fluorescence quenching under mechanical force.

    12. Nanoparticle Targeting

      Polyethylene Glycol Backfilling Mitigates the Negative Impact of the Protein Corona on Nanoparticle Cell Targeting (pages 5093–5096)

      Qin Dai, Carl Walkey and Prof. Warren C. W. Chan

      Article first published online: 2 APR 2014 | DOI: 10.1002/anie.201309464

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      The long and short of it: The adsorption of serum proteins (colored knots) onto targeted nanoparticles (orange circles) can lead to nonspecific cell binding (solid red arrows). Polyethylene glycol (PEG; grey curves) can be used to prevent this; however, long PEG chains can disrupt specific target binding. Shorter PEG chains prevent nonspecific binding without interfering with target recognition (solid green arrow).

    13. Electrocatalysts

      Electrochemical Synthesis of Tetrahexahedral Rhodium Nanocrystals with Extraordinarily High Surface Energy and High Electrocatalytic Activity (pages 5097–5101)

      Neng-Fei Yu, Dr. Na Tian, Dr. Zhi-You Zhou, Long Huang, Jing Xiao, Yu-Hua Wen and Prof. Shi-Gang Sun

      Article first published online: 1 APR 2014 | DOI: 10.1002/anie.201310597

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      Tetrahexahedral rhodium nanocrystals (THH Rh NCs) with {830} high-index facets and high surface energy were prepared for the first time by electrochemical square-wave-potential method. The THH Rh NCs exhibit greatly enhanced electrocatalytic activity over commercial Rh black catalyst for the electrooxidation of ethanol (see picture) and CO owing to the high density of step atoms.

    14. Target Identification

      Phenotypic Screening to Identify Small-Molecule Enhancers for Glucose Uptake: Target Identification and Rational Optimization of Their Efficacy (pages 5102–5106)

      Dr. Minseob Koh, Dr. Jongmin Park, Ja Young Koo, Donghyun Lim, Dr. Mi Young Cha, Ala Jo, Prof. Dr. Jang Hyun Choi and Prof. Dr. Seung Bum Park

      Article first published online: 1 APR 2014 | DOI: 10.1002/anie.201310618

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      A phenotype-based discovery of initial hits enhances the cellular glucose uptake in myotubes and adipocytes. The target identification and rational optimization of initial hits can generate lead compounds with high potency for PPARγ transactivation and cellular glucose uptake. The chirality of optimized ligands differentiated their biophysical and biochemical activities toward PPARγ.

    15. Photocatalysis

      Designing p-Type Semiconductor–Metal Hybrid Structures for Improved Photocatalysis (pages 5107–5111)

      Lili Wang, Jing Ge, Ailun Wang, Mingsen Deng, Xijun Wang, Song Bai, Rui Li, Prof. Jun Jiang, Prof. Qun Zhang, Prof. Yi Luo and Prof. Yujie Xiong

      Article first published online: 2 APR 2014 | DOI: 10.1002/anie.201310635

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      Surface facets matter: Palladium-decorated Cu2O microcrystals exhibit a capability of producing hydrogen from pure water under visible irradiation with well-designed surface facets. This feat is otherwise hard to attain by other Cu2O-based counterparts.

    16. Synthetic Biology

      Reversible Re-programing of Cell–Cell Interactions (pages 5112–5116)

      Kari Gabrielse, Amit Gangar, Dr. Nigam Kumar, Dr. Jae Chul Lee, Dr. Adrian Fegan, Jing Jing Shen, Dr. Qing Li, Dr. Daniel Vallera and Dr. Carston R. Wagner

      Article first published online: 2 APR 2014 | DOI: 10.1002/anie.201310645

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      Lipid chemically self-assembled nanorings (lipid-CSANs) can be used for the stable and reversible modification of any cell surface with a molecular reporter or targeting ligand. In the presence of the antibacterial drug trimethoprim the nanorings were quickly disassembled and the cell–cell interactions reversed.

    17. Mesostructures

      Random-Graft Polymer-Directed Synthesis of Inorganic Mesostructures with Ultrathin Frameworks (pages 5117–5121)

      Dr. Changbum Jo, Dr. Yongbeom Seo, Dr. Kanghee Cho, Jaeheon Kim, Hye Sun Shin, Munhee Lee, Jeong-Chul Kim, Prof. Sang Ouk Kim, Prof. Jeong Yong Lee, Prof. Hyotcherl Ihee and Prof. Ryong Ryoo

      Article first published online: 1 APR 2014 | DOI: 10.1002/anie.201310748

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      In the right direction: Mesostructured inorganic materials, such as zeolite nanosponge, TiO2 nanosheets, and nanosponges of TiO2, SnO2, and ZrO2 were synthesized using amorphous polymers as the structure-directing agent. Many of these materials possessed quite uniform mesopores. Some of them even exhibited small-angle X-ray diffraction. The structure-directing mechanism is also presented.

    18. Hydrogen Bonds

      Hydrogen Bonding Switches the Spin State of Diphenylcarbene from Triplet to Singlet (pages 5122–5125)

      Paolo Costa and Prof. Dr. Wolfram Sander

      Article first published online: 2 APR 2014 | DOI: 10.1002/anie.201400176

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      Carbene solvation: Unlike the triplet, the singlet state of diphenylcarbene forms an exceptionally strong hydrogen bond with methanol (see picture). This leads to an unprecedented triplet-to-singlet ground-state spin switching.

    19. Porous Cage Catenanes

      A Shape-Persistent Quadruply Interlocked Giant Cage Catenane with Two Distinct Pores in the Solid State (pages 5126–5130)

      Dr. Gang Zhang, Dr. Oliver Presly, Dr. Fraser White, Prof. Dr. Iris M. Oppel and Prof. Dr. Michael Mastalerz

      Article first published online: 6 APR 2014 | DOI: 10.1002/anie.201400285

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      Two is better than one: During the crystallization of a giant shape-persistent organic cage compound, a dimeric catenated structure is formed by a 96-fold condensation reaction of 40 molecular subunits. The crystals of the molecular catenane contain one intrinsic mesopore (2.0 nm) and one extrinsic micropore (1.3 nm).

    20. Electrocatalysis

      Engineering Non-sintered, Metal-Terminated Tungsten Carbide Nanoparticles for Catalysis (pages 5131–5136)

      Sean T. Hunt, Tarit Nimmanwudipong and Prof. Yuriy Román-Leshkov

      Article first published online: 2 APR 2014 | DOI: 10.1002/anie.201400294

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      A removable ceramic coating method is used to generate metal-terminated transition-metal carbide nanoparticles with strict control over size, composition, and crystal phase. Tungsten carbide and molybdenum tungsten carbide nanoparticles in the 1–4 nm range achieve activities 100-fold higher than commercial carbides and within an order of magnitude of platinum-based catalysts for the hydrogen evolution and methanol electrooxidation reactions.

    21. Multifunctional Nanocapsules

      Fabrication of Multiresponsive Bioactive Nanocapsules through Orthogonal Self-Assembly (pages 5137–5141)

      Yi-Cheun Yeh, Rui Tang, Rubul Mout, Youngdo Jeong and Prof. Vincent M. Rotello

      Article first published online: 1 APR 2014 | DOI: 10.1002/anie.201400559

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      Multifunctional nanocapsules: Multifunctional nanoparticle-stabilized capsules (NPSCs) have been fabricated by using a set of orthogonal supramolecular interactions. The resultant supramolecular nanocapsules feature dual-delivery capability of proteins and hydrophobic endosome-disrupting agents to allow stimuli-responsive protein release into the cytosol with fluorescence monitoring.

    22. Heterocycle Synthesis

      Rhodium(II)-Catalyzed Intramolecular Annulation of 1-Sulfonyl-1,2,3-Triazoles with Pyrrole and Indole Rings: Facile Synthesis of N-Bridgehead Azepine Skeletons (pages 5142–5146)

      Jin-Ming Yang, Cheng-Zhi Zhu, Dr. Xiang-Ying Tang and Prof. Dr. Min Shi

      Article first published online: 3 APR 2014 | DOI: 10.1002/anie.201400881

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      Heads up: A convenient and efficient synthetic method of highly functionalized N-bridgehead azepine skeletons was developed using a rhodium(II)-catalyzed intramolecular annulation of pyrrolyl and indolyl triazoles. Several interesting transformations of the products into poly-heterocyclic products and the reaction mechanism are disclosed. Ts=4-toluenesulfonyl.

    23. C[BOND]H Activation

      Intermolecular Domino Reaction of Two Aryl Iodides Involving Two C[BOND]H Functionalizations (pages 5147–5151)

      Dr. Marcel Sickert, Dr. Harald Weinstabl, Brendan Peters, Xiao Hou and Prof. Dr. Mark Lautens

      Article first published online: 3 APR 2014 | DOI: 10.1002/anie.201400807

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      Pendulum Reaction: 1 Pd complex catalyzes the intermolecular reaction of 2 aryl iodides to form 3 new C[BOND]C bonds through 2 C[BOND]H activations and 1 carbopalladation. The intermolecular domino reaction of two aryl iodides gives fused biaryls with a high level of convergence and efficiency. The key to success lies in the choice of an appropriate bulky Pd catalyst, which allows the aryl iodides to be distinguished in the key step.

    24. Electrocatalysis

      NHC-Containing Manganese(I) Electrocatalysts for the Two-Electron Reduction of CO2 (pages 5152–5155)

      Dr. Jay Agarwal, Travis W. Shaw, Charles J. Stanton III, Prof. Dr. George F. Majetich, Prof. Dr. Andrew B. Bocarsly and Prof. Dr. Henry F. Schaefer III

      Article first published online: 2 APR 2014 | DOI: 10.1002/anie.201311099

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      Catalytic manganese N-heterocyclic carbene complexes have been synthesized and characterized: [MnBrL(CO)3] (see scheme; L=N-methyl-N′-2-pyridylbenzimidazol-2-ylidine or N-methyl-N′-2-pyridylimidazol-2-ylidine). Both species mediate the reduction of CO2 to CO following two-electron reduction of the MnI center at a single potential, as observed with preparative scale electrolysis and verified with 13CO2.

    25. Cluster Compounds

      High Yielding Synthesis of Carboranes Under Mild Reaction Conditions Using a Homogeneous Silver(I) Catalyst: Direct Evidence of a Bimetallic Intermediate (pages 5156–5160)

      Dr. Mohamed E. El-Zaria, Kunal Keskar, Dr. Afaf R. Genady, Dr. Joseph A. Ioppolo, Dr. James McNulty and Dr. John F. Valliant

      Article first published online: 2 APR 2014 | DOI: 10.1002/anie.201311012

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      Cluster around: Current methods to prepare carboranes require heating to high temperatures, thereby limiting the range of derivatives which can be prepared from functionalized alkynes. By using a AgI catalyst it is possible to prepare carboranes from substituted alkynes in good to excellent yields at temperatures below 40 °C, including room temperature. The approach provides an important new synthetic strategy for the preparation of functionalized boron clusters.

    26. Asymmetric Catalysis

      Desymmetrization of Diolefinic Diols by Enantioselective Amino-thiocarbamate-Catalyzed Bromoetherification: Synthesis of Chiral Spirocycles (pages 5161–5164)

      Daniel Weiliang Tay, Dr. Gulice Y. C. Leung and Prof. Dr. Ying-Yeung Yeung

      Article first published online: 6 APR 2014 | DOI: 10.1002/anie.201310136

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      Seeing double: A facile, efficient, and highly diastereo- and enantioselective bromoetherification of diolefinic diols has been developed using an amino-thio-carbamate catalyst. Further manipulations of the bromoether products enabled entry into a new class of spirocycles, having three stereogenic quaternary carbon centers, which are distinctively lacking in the literature.

    27. Anode Materials

      Scalable Synthesis of Interconnected Porous Silicon/Carbon Composites by the Rochow Reaction as High-Performance Anodes of Lithium Ion Batteries (pages 5165–5169)

      Zailei Zhang, Dr. Yanhong Wang, Wenfeng Ren, Prof. Qiangqiang Tan, Prof. Yunfa Chen, Prof. Hong Li, Dr. Ziyi Zhong and Prof. Dr. Fabing Su

      Article first published online: 2 APR 2014 | DOI: 10.1002/anie.201310412

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      Digging pores: A scalable synthesis route was developed to prepare interconnected porous Si/C composites by the commercialized Rochow reaction using Si microparticles and CH3Cl gas over the various Cu-based catalysts under the mild reaction conditions. The obtained porous Si/C materials as anodes of Li ion batteries exhibit high electrochemical performance.

    28. Synthetic Methods

      Intramolecular Aminocyanation of Alkenes by N[BOND]CN Bond Cleavage (pages 5170–5174)

      Zhongda Pan, Sarah M. Pound, Naveen R. Rondla and Prof. Dr. Christopher J. Douglas

      Article first published online: 9 APR 2014 | DOI: 10.1002/anie.201310983

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      Break free: A Lewis acid promoted intramolecular aminocyanation of alkenes is described. Activation of N-sulfonyl cyanamides by B(C6F5)3 leads to cleavage of the N[BOND]CN bond in conjunction with vicinal addition of sulfonamide and nitrile groups across an alkene. This method enables rapid and atom-economical access to heterocycles in excellent yields. Mechanistic studies indicate that this transformation proceeds without dissociation of the nitrile.

    29. Negative Thermal Expansion

      Interpenetration as a Mechanism for Negative Thermal Expansion in the Metal–Organic Framework Cu3(btb)2 (MOF-14) (pages 5175–5178)

      Yue Wu, Dr. Vanessa K. Peterson, Emily Luks, Dr. Tamim A. Darwish and Prof. Cameron J. Kepert

      Article first published online: 1 APR 2014 | DOI: 10.1002/anie.201311055

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      When push comes to pull: A new mechanism for negative thermal expansion is reported. In the metal–organic framework Cu3(btb)2 (MOF-14; btb=4,4′,4′′-benzene-1,3,5-triyl-tribenzoate), the large thermal expansion of the weak interactions that hold the two interpenetrating networks together results in a low-energy contractive distortion of the overall framework structure.

    30. C[BOND]H Functionalization

      Redox-Neutral α,β-Difunctionalization of Cyclic Amines (pages 5179–5182)

      Weijie Chen, Dr. YoungKu Kang, Dr. Richard G. Wilde and Prof. Dr. Daniel Seidel

      Article first published online: 1 APR 2014 | DOI: 10.1002/anie.201311165

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      An unprecedented α,β-difunctionalization reaction of amines affords polycyclic N,O-acetals from simple 1-(aminomethyl)-β-naphthols or 2-(aminomethyl)-phenols. These transformations are redox-neutral and proceed in the absence of any additives.

    31. Water Oxidation

      A Molecular Approach to Self-Supported Cobalt-Substituted ZnO Materials as Remarkably Stable Electrocatalysts for Water Oxidation (pages 5183–5187)

      Johannes Pfrommer, Dr. Michael Lublow, Anahita Azarpira, Dr. Caren Göbel, Marcel Lücke, Dr. Alexander Steigert, Martin Pogrzeba, Dr. Prashanth W. Menezes, Dr. Anna Fischer, Dr. Thomas Schedel-Niedrig and Prof. Dr. Matthias Driess

      Article first published online: 28 APR 2014 | DOI: 10.1002/anie.201400243

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      To be self-made: A cobalt-substituted zinc oxide (Co:ZnO) precatalyst was synthesized by low-temperature solvolysis of molecular heterobimetallic Co4−xZnxO4 (x=1–3) precursors. Electrophoretic deposition onto fluorinated tin oxide (FTO) electrodes leads, after oxidative conditioning, to an amorphous self-supported water-oxidation electrocatalyst that performs at very low overpotentials and with high current density for several hours.

    32. Chemical Protein Synthesis

      Total Chemical Synthesis and Biological Activities of Glycosylated and Non-Glycosylated Forms of the Chemokines CCL1 and Ser-CCL1 (pages 5188–5193)

      Prof. Dr. Ryo Okamoto, Dr. Kalyaneswar Mandal, Dr. Morris Ling, Prof. Dr. Andrew D. Luster, Prof. Dr. Yasuhiro Kajihara and Prof. Dr. Stephen B. H. Kent

      Article first published online: 18 MAR 2014 | DOI: 10.1002/anie.201310574

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      Man-made: Total chemical synthesis was used to prepare glycosylated and non-glycosylated forms of the chemokines CCL1 and Ser-CCL1. In a chemotaxis assay using a CCR8-transfected cell line, non-glycosylated CCL1 was more active than glycosylated CCL1; both non-glycosylated and glycosylated Ser-CCL1 had only minimal activity in the same assay.

    33. Glycoprotein X-ray Structure

      (Quasi-)Racemic X-ray Structures of Glycosylated and Non-Glycosylated Forms of the Chemokine Ser-CCL1 Prepared by Total Chemical Synthesis (pages 5194–5198)

      Prof. Dr. Ryo Okamoto, Dr. Kalyaneswar Mandal, Dr. Michael R. Sawaya, Prof. Dr. Yasuhiro Kajihara, Prof. Dr. Todd O. Yeates and Prof. Dr. Stephen B. H. Kent

      Article first published online: 1 APR 2014 | DOI: 10.1002/anie.201400679

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      Look into the mirror: The X-ray structure of the chemically synthesized glycoprotein Ser-CCL1 (right in picture) was determined by crystallization as the quasi-racemate with the non-glycosylated mirror image protein D-Ser-CCL1 (left). This enabled comparison of the glycoprotein structure with the corresponding non-glycosylated form of the same protein molecule and showed that glycosylation had no effect on the tertiary structure of the protein moiety.

    34. Atom Economy

      Reductive Amination without an External Hydrogen Source (pages 5199–5201)

      Dr. Denis Chusov and Prof. Benjamin List

      Article first published online: 14 MAR 2014 | DOI: 10.1002/anie.201400059

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      Look, no H2! Reductive amination without an external hydrogen source has been developed using carbon monoxide as the reductant and rhodium acetate (0.2–1 mol %) as catalyst. The method tolerates a variety of functional groups and provides target amines in good to excellent yields.

    35. Helicenes

      Asymmetric Catalysis on the Nanoscale: The Organocatalytic Approach to Helicenes (pages 5202–5205)

      Lisa Kötzner, Dr. Matthew J. Webber, Dr. Alberto Martínez, Dr. Claudia De Fusco and Prof. Dr. Benjamin List

      Article first published online: 15 APR 2014 | DOI: 10.1002/anie.201400474

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      Twisting indoles: A novel chiral Brønsted acid, specifically designed for long-range control on a nanoscale, catalyzes the asymmetric synthesis of azahelicenes through a Fischer indolization. The method has the advantage of starting from simple achiral starting materials, which can be modified by changing the protecting group (R2) or the terminal substituents (R1, R3). The products can be further oxidized to polyaromatic systems.

    36. Direct fluorination

      Synthesis of Tris- and Tetrakis(pentafluoroethyl)silanes (pages 5206–5209)

      Simon Steinhauer, Dr. Julia Bader, Dr. Hans-Georg Stammler, Dr. Nikolai Ignat‘ev and Prof. Dr. Berthold Hoge

      Article first published online: 1 APR 2014 | DOI: 10.1002/anie.201400291

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      Special eFfects: functional and highly Lewis acidic tris(pentafluoroethyl)silanes as well as the tetrakis(perfluoroalkyl)silanes Si(C2F5)4 and Si(C2F5)3CF3 are prepared. The two tetrakis species were formed in the direct fluorination of tris-(pentafluoroethyl)ethyl- and methylsilane. Si(C2F5)4 was characterized by X-ray crystallography (see figure).

    37. Oxidative Phenol Cross-Coupling

      Metal- and Reagent-Free Highly Selective Anodic Cross-Coupling Reaction of Phenols (pages 5210–5213)

      Bernd Elsler, Dr. Dieter Schollmeyer, Dr. Katrin Marie Dyballa, Prof. Dr. Robert Franke and Prof. Dr. Siegfried R. Waldvogel

      Article first published online: 18 MAR 2014 | DOI: 10.1002/anie.201400627

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      Current synthesis: In a highly sustainable access to mixed biphenols, electric current makes the use of reagents, catalysts, and leaving groups obsolete. Solvents with a strong tendency to act as hydrogen-bond donors lead to a unique selectivity for the cross-coupling product.

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