Angewandte Chemie International Edition

Cover image for Vol. 52 Issue 50

December 9, 2013

Volume 52, Issue 50

Pages 13107–13476

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Minireview
    11. Reviews
    12. Communications
    1. You have free access to this content
      Cover Picture: Proton Cascade in a Molecular Solid: H/D Exchange on Mobile and Immobile Water (Angew. Chem. Int. Ed. 50/2013) (page 13107)

      Dr. Silvia C. Capelli, Prof. Larry R. Falvello, Elena Forcén-Vázquez, Prof. Garry J. McIntyre, Prof. Fernando Palacio, Dr. Sergio Sanz and Dr. Milagros Tomás

      Article first published online: 25 NOV 2013 | DOI: 10.1002/anie.201309817

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      A reflection on the “Grotthuss mechanism” of proton transport observed in nonporous single crystals by L. R. Falvello, G. J. McIntyre, M. Tomás et al. in their Communication on page 13463 ff. The pirouette shows the rotation of water molecules, one step in the mechanism, and the grand jeté leap is a metaphor for proton hopping along the water wire, the other step. The backdrop shows two strands of the polymer in the crystal, whose unit cell outline provides a 3D frame for the scene.

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      Inside Cover: An Adaptable and Dynamically Porous Organic Salt Traps Unique Tetrahalide Dianions (Angew. Chem. Int. Ed. 50/2013) (page 13108)

      Dr. Javier Martí-Rujas, Dr. Lorenzo Meazza, Dr. Gin Keat Lim, Dr. Giancarlo Terraneo, Dr. Tullio Pilati, Prof. Dr. Kenneth D. M. Harris, Prof. Dr. Pierangelo Metrangolo and Prof. Dr. Giuseppe Resnati

      Article first published online: 26 NOV 2013 | DOI: 10.1002/anie.201309857

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      The discrete [I2Br2 ]2− dianion is obtained for the first time by dynamic rearrangement of a diammonium crystalline salt which loses diiodine vapors under thermal stimulus and thus displays adaptable porosity. In their Communication on page 13444 ff., K. D. M. Harris, P. Metrangolo, G. Resnati, et al. show that the process is driven by the cation/supramolecular anion size-matching, is general, as it affords also the rare [I2Cl2]2− and [I4]2− dianions, and is reversible.

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      Inside Back Cover: Structure-Based Design of an RNA-Binding p-Terphenylene Scaffold that Inhibits HIV-1 Rev Protein Function (Angew. Chem. Int. Ed. 50/2013) (page 13477)

      Luis González-Bulnes, Ignacio Ibáñez, Dr. Luis M. Bedoya, Manuela Beltrán, Dr. Silvia Catalán, Dr. José Alcamí, Prof. Santos Fustero and Dr. José Gallego

      Article first published online: 25 NOV 2013 | DOI: 10.1002/anie.201309856

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      Bilaterally substituted p-terphenyl molecules reproduce the interactions of an α-helix of the HIV-1 protein Rev with its RNA receptor and block Rev function and virus replication. In their Communication on page 13405 ff., J. Alcamí, S. Fustero, and J. Gallego et al. report the structure-based design of p-terphenyl molecules that inhibit the Rev-mediated transport of HIV-1 RNA from the nucleus to the cytoplasm by binding to the RNA loop that is recognized by Rev (image prepared with the help of M.C. Ibáñez).

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      Back Cover: Approaching White-Light Emission from a Phosphorescent Trinuclear Gold(I) Cluster by Modulating Its Aggregation Behavior (Angew. Chem. Int. Ed. 50/2013) (page 13478)

      Dr. Wen-Xiu Ni, Mian Li, Ji Zheng, Dr. Shun-Ze Zhan, Yu-Min Qiu, Prof. Dr. Seik Weng Ng and Prof. Dr. Dan Li

      Article first published online: 25 NOV 2013 | DOI: 10.1002/anie.201309815

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      Light up the world with white light from gold. In their Communication on page 13472 ff., D. Li and co-workers introduce an organic chromophore, thiophene, into a classical trinuclear gold(I) pyrazolate core that gives off aurophilic phosphorescence. The cooperation of dual emissions in the blue–green and orange–red regions underlies this solid-state white-light emitter, along with a red-emitting crystalline polymorph that assists the interpretation of this unusual observation in gold photochemistry.

  2. Editorial

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Minireview
    11. Reviews
    12. Communications
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      Learning a New Language: Moving Countries and Changing Subjects (pages 13110–13111)

      Prof. Dr. Wilhelm T. S. Huck

      Article first published online: 25 OCT 2013 | DOI: 10.1002/anie.201308116

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  3. Graphical Abstract

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

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

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Minireview
    11. Reviews
    12. Communications
    1. Robert Schlögl (pages 13140–13141)

      Article first published online: 28 AUG 2013 | DOI: 10.1002/anie.201305637

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      “My favorite time of day is the sunset. In a spare hour, I observe how people interact with their environment …” This and more about Robert Schlögl can be found on page 13140.

  6. News

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

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Minireview
    11. Reviews
    12. Communications
    1. Protein–Protein Interactions in Drug Discovery. (Series: Methods and Principles in Medicinal Chemistry, Vol. 56) Edited by Alexander Dömling. (pages 13143–13144)

      Joachim Rudolph

      Article first published online: 7 NOV 2013 | DOI: 10.1002/anie.201307711

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      Wiley-VCH, Weinheim, 2013. 334 pp., hardcover, € 138.00.—ISBN 978-3527331079

  8. Highlights

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

      New Endeavors in Gold Catalysis—Size Matters (pages 13146–13148)

      Dr. Rafael Gramage-Doria and Prof. Dr. Joost N. H. Reek

      Article first published online: 15 OCT 2013 | DOI: 10.1002/anie.201307205

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      Golden times: Recent breakthroughs in gold-catalyzed transformations using nanosized homogeneous gold catalysts are highlighted. These catalysts have activities and stabilities comparable to (or even surpassing) heterogeneous catalysts. Well-defined, ligand-supported gold clusters turned out to be active in homogeneous catalysis, a catalyst concept which holds potential for future studies.

    2. Asymmetric Catalysis

      Dual Catalysis Becomes Diastereodivergent (pages 13149–13152)

      Dr. Maria Teresa Oliveira, Dr. Marco Luparia, Dr. Davide Audisio and Dr. Nuno Maulide

      Article first published online: 15 OCT 2013 | DOI: 10.1002/anie.201305933

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      Diastereodivergent is cool: The development of catalytic systems able to generate each and every one of the possible product diastereoisomers from the same starting materials (i.e., that are “diastereodivergent”) is an emerging field in asymmetric catalysis. The possibility of designing such systems in a rational manner based on dual catalysis has now become reality.

  9. Minireview

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Minireview
    11. Reviews
    12. Communications
    1. Nucleic Acid Sequencing

      Nanopore-Based Sequencing and Detection of Nucleic Acids (pages 13154–13161)

      Yi-Lun Ying, Dr. Junji Zhang, Rui Gao and Prof. Yi-Tao Long

      Article first published online: 8 NOV 2013 | DOI: 10.1002/anie.201303529

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      Adopted from nature: The functions of natural ion channels can be mimicked with both biological and solid-state nanopores, which have attracted increasing attention for their possible use in the detection and sequencing of DNA. In this Minireview, background and latest progress in this area are summarized and a novel platform for nanopore-based detection is discussed.

  10. Reviews

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

      Graphene Analogues of Inorganic Layered Materials (pages 13162–13185)

      Prof. Dr. C. N. R. Rao, H. S. S. Ramakrishna Matte and Urmimala Maitra

      Article first published online: 11 OCT 2013 | DOI: 10.1002/anie.201301548

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      Single and few-layer MoS2, BN, and similar layered inorganic compounds are emerging as very interesting materials with numerous potential applications. This Review describes the synthesis and characterization of these graphene analogues and presents some of their physical properties and applications.

    2. Lithium–Sulfur Batteries

      Lithium–Sulfur Batteries: Electrochemistry, Materials, and Prospects (pages 13186–13200)

      Dr. Ya-Xia Yin, Sen Xin, Prof. Yu-Guo Guo and Prof. Li-Jun Wan

      Article first published online: 14 NOV 2013 | DOI: 10.1002/anie.201304762

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      Electrochemical cells with high energy densities are of great importance to satisfy the urgent demand for electronic vehicles and electricity storage. The Li-S battery is one promising candidate, yet it suffers from the low utilization of active materials and poor cycle stability. The electrochemistry and challenges facing Li-S batteries is addressed, and recent progress of materials related to Li-S batteries is summarized.

  11. Communications

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

      Melting at High Pressure: Can First-Principles Computational Chemistry Challenge Diamond-Anvil Cell Experiments? (pages 13202–13205)

      Dr. Jonas Wiebke, Dr. Elke Pahl and Prof. Dr. Peter Schwerdtfeger

      Article first published online: 7 NOV 2013 | DOI: 10.1002/anie.201308039

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      Putting the bite on argon: Ab initio Monte Carlo simulations of superheated argon crystals at up to 100 GPa suggest that theory can provide a more accurate picture of high-pressure melting than modern diamond-anvil cell experiments.

    2. Water Oxidation Catalysts

      Active Mixed-Valent MnOx Water Oxidation Catalysts through Partial Oxidation (Corrosion) of Nanostructured MnO Particles (pages 13206–13210)

      Dr. Arindam Indra, Dr. Prashanth W. Menezes, Dr. Ivelina Zaharieva, Elham Baktash, Johannes Pfrommer, Dr. Michael Schwarze, Prof. Dr. Holger Dau and Prof. Dr. Matthias Driess

      Article first published online: 31 OCT 2013 | DOI: 10.1002/anie.201307543

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      Yes, we CAN: Partial oxidation of inactive MnO nanoparticles by CeIV as oxidant gives active MnOx catalysts that are suitable for effective photochemical and electrochemical water oxidation. The active MnOx catalyst contains mixed-valent MnII, MnIII, and MnIV species (see picture; green and violet) interconnected through oxido bridges (red) with defects and disorders. MnOx is analogous to calcium–manganese oxide systems where the calcium sites are replaced by MnII or MnIII ions.

    3. Nanolaminates

      Controlling Size-Induced Phase Transformations Using Chemically Designed Nanolaminates (pages 13211–13214)

      Prof. Matt Beekman, Dr. Sabrina Disch, Prof. Sergei Rouvimov, Dr. Deepa Kasinathan, Dr. Klaus Koepernik, Dr. Helge Rosner, Dr. Paul Zschack, Prof. Dr. Wolfgang S. Neumann and Prof. David C. Johnson

      Article first published online: 16 OCT 2013 | DOI: 10.1002/anie.201305377

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      By dimensionally constraining crystalline layers in a non-epitaxial intergrowth, nanocrystal ensembles with well-defined and precisely controlled size are prepared. Synchrotron X-ray diffraction, electron microscopy, and density functional theory show that a size-induced second-order structural transition allows the crystal structure of a layered semiconductor (SnSe) to be continuously tuned by controlling the thickness of the individual layers.

    4. Polyketide Biosynthesis

      An Enzymatic Domain for the Formation of Cyclic Ethers in Complex Polyketides (pages 13215–13218)

      Petra Pöplau, Sarah Frank, Dr. Brandon I. Morinaka and Prof. Dr. Jörn Piel

      Article first published online: 4 NOV 2013 | DOI: 10.1002/anie.201307406

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      Champion cyclist: In vitro studies on the pederin biosynthetic pathway identify pyran synthases (PS) as a new family of polyketide synthase domains that stereoselectively form diverse five- and six-membered ether rings by oxa-conjugate cyclization during carbon-chain elongation. These domains could be useful tools for chemoenzymatic synthesis.

    5. Quantum Sieving

      A Cryogenically Flexible Covalent Organic Framework for Efficient Hydrogen Isotope Separation by Quantum Sieving (pages 13219–13222)

      Hyunchul Oh, Dr. Suresh Babu Kalidindi, Youngje Um, Dr. Sareeya Bureekaew, Dr. Rochus Schmid, Prof. Dr. Roland A. Fischer and Dr. Michael Hirscher

      Article first published online: 11 NOV 2013 | DOI: 10.1002/anie.201307443

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      Pyrdine incorporation into the covalent organic framework COF-1 resulted in a highly dense packing structure in which the pyridine occupies the hexagonal pore space between the COF layers. This optimizes pore aperture for quantum sieving of hydrogen isotopes and introduces flexibility at cryogenic temperatures into the system. The separation factor (Sinline image) is about 10 at 22 K, which is the highest reported to date.

    6. Cascade Reactions

      Asymmetric Palladium(II)-Catalyzed Cascade Reaction Giving Quaternary Amino Succinimides by 1,4-Addition and a Nef-Type Reaction (pages 13223–13227)

      Dipl.-Chem. Manuel Weber, Dr. Wolfgang Frey and Prof. Dr. René Peters

      Article first published online: 21 OCT 2013 | DOI: 10.1002/anie.201307334

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      Simple starting materials, high-value products: A dinuclear ferrocene-based PdII complex transforms mixtures of racemic N-benzoyl α-amino acids, nitroolefins, acetic anhydride, and manganese acetate into biologically interesting quaternary aminosuccinimides. The products are obtained as single diastereomers in enantioenriched form. Key steps of the cascade mechanism are a 1,4-addition of in situ generated azlactones to nitroolefins and a Nef-type reaction.

    7. Oxidative Coupling

      Synergistic Effect of Ketone and Hydroperoxide in Brønsted Acid Catalyzed Oxidative Coupling Reactions (pages 13228–13232)

      Bertrand Schweitzer-Chaput, Dr. Abhishek Sud, Dr. Áron Pintér, Stefanie Dehn, Dr. Philipp Schulze and Dr. Martin Klussmann

      Article first published online: 22 OCT 2013 | DOI: 10.1002/anie.201306752

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      Waste not wasted: A mechanistic study of the autoxidative coupling of xanthene with cyclopentanone uncovered an autoinductive effect of the waste product hydrogen peroxide. It generates radicals in the presence of acid and ketones, which accelerate the reaction by providing an additional pathway to the reactive hydroperoxide intermediate. This discovery could be applied to achieve other Brønsted acid catalyzed oxidative coupling reactions.

    8. Electrochemical Lithium Deposition

      Microcalorimetric Measurements of the Solvent Contribution to the Entropy Changes upon Electrochemical Lithium Bulk Deposition (pages 13233–13237)

      Matthias J. Schmid, Katrin R. Bickel, Prof. Petr Novák and Prof. Rolf Schuster

      Article first published online: 24 OCT 2013 | DOI: 10.1002/anie.201305508

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      A strongly positive entropy of reaction for the bulk deposition of Li can be explained by the desolvation of Li+ ions, as revealed by microcalorimetric studies. From this the coordination number of Li+ can be derived. The positive entropy leads to cooling of the electrode, which may influence lithium plating in lithium-ion batteries.

    9. Rare-Earth-Metal Hydrides

      Methylaluminum-Supported Rare-Earth-Metal Dihydrides (pages 13238–13242)

      Christoph Schädle, Dorothea Schädle, Dr. Klaus Eichele and Prof. Dr. Reiner Anwander

      Article first published online: 16 OCT 2013 | DOI: 10.1002/anie.201306783

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      The super-bulky hydrotris(3-tert-butyl-5-methylpyrazolyl)borato ligand (TptBu,Me) allows the isolation of the monolanthanide complexes [TptBu,MeLn{(μ-H)AlMe3}2] (Ln=Y, Lu; see structure), which can be transformed into discrete non-agglomerated imide complexes [TptBu,MeLn{(μ-NC6H3Me2-2,6)(μ-H)AlMe2}] by reaction with dimethylaniline. Ln hydrido bonding is corroborated by 1H NMR spectroscopy through 1H–89Y coupling and 89Y DEPT45 NMR spectroscopy.

    10. Domino Reactions

      A Domino Approach to Dibenzopentafulvalenes by Quadruple Carbopalladation (pages 13243–13246)

      M. Sc. Jan Wallbaum, M. Sc. Roman Neufeld, Prof. Dr. Dietmar Stalke and Prof. Dr. Daniel B. Werz

      Article first published online: 7 NOV 2013 | DOI: 10.1002/anie.201307793

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      Four at one stroke: A quadruple domino carbopalladation reaction gives access to highly substituted dibenzopentafulvalenes and the complete pentafulvalene backbone is constructed in only one synthetic step. Structural and electronic properties have been evaluated by X-ray crystallography and cyclovoltammetry.

    11. CO Activation

      Carbonylation of Cyclotrisilenes (pages 13247–13250)

      Dr. Michael J. Cowley, Yu Ohmori, Dr. Volker Huch, Dr. Masaaki Ichinohe, Prof. Dr. Akira Sekiguchi and Prof. Dr. David Scheschkewitz

      Article first published online: 7 NOV 2013 | DOI: 10.1002/anie.201307450

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      Spontaneous reaction of carbon monoxide with cyclotrisilenes has been observed. Depending on the substitution pattern, the initial product of carbonylation either dimerizes or can be trapped to yield highly functionalized cyclic silenes.

    12. Spin Isomers

      Nuclear Spin Isomers of Ethylene: Enrichment by Chemical Synthesis and Application for NMR Signal Enhancement (pages 13251–13255)

      Dr. Vladimir V. Zhivonitko, Dr. Kirill V. Kovtunov, Prof. Pavel L. Chapovsky and Prof. Igor V. Koptyug

      Article first published online: 14 OCT 2013 | DOI: 10.1002/anie.201307389

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      Taking CH2CH2 for a spin: Enrichment of the nuclear spin isomers of ethylene was achieved by a catalytic reaction of acetylene with parahydrogen (see scheme). The spin isomers were used for NMR signal enhancement, both with and without subjecting them to a chemical reaction. The interconversion times of the nuclear spin isomers were evaluated at ambient pressure, thus revealing extremely long-lived spin states with lifetimes of (1000±400) s.

    13. Natural Product Synthesis

      Divergent Total Synthesis of Indoxamycins A, C, and F (pages 13256–13260)

      Chi He, Chenlong Zhu, Zhifeng Dai, Dr. Chih-Chung Tseng and Prof. Dr. Hanfeng Ding

      Article first published online: 31 OCT 2013 | DOI: 10.1002/anie.201307426

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      The concise and divergent total synthesis of (−)-indoxamycins A, C, and F has been completed for the first time by using a tricyclic enone as the common late-stage intermediate. The key steps of the strategy are based on an Ireland–Claisen rearrangement, a stereodivergent reductive 1,6-enyne cyclization, and a tandem 1,2-addition/oxa-Michael/methylenation reaction.

    14. Sequence-Controlled Oligomers

      Multifunctionalized Sequence-Defined Oligomers from a Single Building Block (pages 13261–13264)

      Dr. Pieter Espeel, Lieselot L. G. Carrette, Katarzyna Bury, Sven Capenberghs, Prof. José C. Martins, Prof. Filip E. Du Prez and Prof. Annemieke Madder

      Article first published online: 31 OCT 2013 | DOI: 10.1002/anie.201307439

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      Another link in the chain: A thiolactone-based approach for the preparation of multifunctionalized sequence-defined oligomeric structures on solid support was established. The iterative aminolysis/chain extension method with a single building block and a variety of commercial amines allowed for the protecting group free synthesis of various oligomeric motifs with a unique backbone and a preprogrammed organization of side chain functionalities.

    15. Synthetic Methods

      A Metal-Free Multicomponent Cascade Reaction for the Regiospecific Synthesis of 1,5-Disubstituted 1,2,3-Triazoles (pages 13265–13268)

      Dr. Guolin Cheng, Xiaobao Zeng, Jinhai Shen, Xuesong Wang and Prof. Xiuling Cui

      Article first published online: 13 NOV 2013 | DOI: 10.1002/anie.201307499

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      About specifics: A method for the regiospecific synthesis of the title compounds through an unprecedented Michael addition/deacylative diazo transfer/cyclization sequence has been established. The simple and practical method can be used for the modification of primary amines including chiral α-amines. The process involves the formation three covalent bonds and the cleavage of two covalent bonds (see scheme, Ts=4-toluenesulfonyl).

    16. Template Synthesis

      Synthesis of a [2]Catenane from the Sodium Ion Templated Orthogonal Arrangement of Two Diethylene Glycol Chains (pages 13269–13272)

      Shun-Te Tung, Prof. Chien-Chen Lai, Yi-Hung Liu, Prof. Shie-Ming Peng and Prof. Sheng-Hsien Chiu

      Article first published online: 13 NOV 2013 | DOI: 10.1002/anie.201307640

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      Take five: Two dialdehydes, two diamines, one Na+ ion have been used to generate a [2]catenane. This simple and efficient synthesis makes use of a Na+ ion as a template to align in an orthogonal manner two diethylene glycol chains between the two amine groups (see scheme, TFPB=tetrakis(3,5-trifluoromethylphenyl)borate).

    17. Total Synthesis

      Total Synthesis and Structural Revision of the Alkaloid Incargranine B (pages 13273–13275)

      Patrick D. Brown, Dr. Anthony C. Willis, Prof. Michael S. Sherburn and Dr. Andrew L. Lawrence

      Article first published online: 24 OCT 2013 | DOI: 10.1002/anie.201307875

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      Seeing double: Consideration of the biosynthetic origins of incargranine B, which was originally assigned an unprecedented indolo[1.7]naphthyridine structure, led to the proposal of a dipyrroloquinoline framework as a more biosynthetically feasible structure (see scheme; Piv=pivaloyl). This hypothesis was validated by a short biomimetic synthesis of incargranine B.

    18. Nanomachines

      Micromotor-Based High-Yielding Fast Oxidative Detoxification of Chemical Threats (pages 13276–13279)

      Dr. Jahir Orozco, Guanzhi Cheng, Diana Vilela, Dr. Sirilak Sattayasamitsathit, Prof. Rafael Vazquez-Duhalt, Dr. Gabriela Valdés-Ramírez, Dr. On Shun Pak, Prof. Alberto Escarpa, Prof. Chengyou Kan and Prof. Joseph Wang

      Article first published online: 24 OCT 2013 | DOI: 10.1002/anie.201308072

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      Oxidative decontamination: An effective strategy for the oxidative neutralization of organophosphorus nerve agents that is based on self-propelled micromotors has been developed. The movement of multiple motors across a peroxide-activated contaminated solution enhances the decontamination efficiency compared with common neutralization processes for chemical warfare agents.

    19. Hydroacylation

      You have full text access to this OnlineOpen article
      2-Aminobenzaldehydes as Versatile Substrates for Rhodium-Catalyzed Alkyne Hydroacylation: Application to Dihydroquinolone Synthesis (pages 13280–13283)

      Matthias Castaing, Sacha L. Wason, Beatriz Estepa, Dr. Joel F. Hooper and Prof. Michael C. Willis

      Article first published online: 12 NOV 2013 | DOI: 10.1002/anie.201308127

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      Amine for it! A cationic rhodium catalyst, which was assembled in situ from commercial components, promoted the reaction of a range of simple 2-aminobenzaldehydes with terminal and internal alkynes in a series of intermolecular hydroacylation reactions. The products of this reaction, amino-substituted enones, were efficiently converted into the corresponding dihydro-4-quinolones.

    20. Asymmetric Catalysis

      Chiral Copper(II) Phosphate Catalyzed Enantioselective Synthesis of Isochromene Derivatives by Sequential Intramolecular Cyclization and Asymmetric Transfer Hydrogenation of o-Alkynylacetophenones (pages 13284–13288)

      Dr. Kodai Saito, Yuki Kajiwara and Prof. Dr. Takahiko Akiyama

      Article first published online: 13 NOV 2013 | DOI: 10.1002/anie.201308303

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      A good mix: The title reaction of o-alkynylacetophenones with the Hantzsch ester in the presence of a chiral copper/phosphate catalyst proceeds in good yields with excellent enantioselectivities. The key intermediate for enantiocontrol is the ion pair of the carbonyl ylide with a chiral phosphate anion, and this process provides straight forward access to highly enantioriched chiral isochromenes.

    21. Photochemistry

      Synthesis of 6-Alkylated Phenanthridine Derivatives Using Photoredox Neutral Somophilic Isocyanide Insertion (pages 13289–13292)

      Heng Jiang, Yuanzheng Cheng, Ruzhi Wang, Mengmeng Zheng, Prof. Dr. Yan Zhang and Prof. Dr. Shouyun Yu

      Article first published online: 12 NOV 2013 | DOI: 10.1002/anie.201308376

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      Bring to light: The first visible-light-promoted somophilic isocyanide insertion occurs using an iridium photocatalyst. This efficient synthetic approach provides a rapid entry to 6-alkylated phenanthridine derivatives (see scheme). The reactions proceed at room temperature in good to excellent yields with broad substrate scope and under environmentally friendly conditions.

    22. Boron Cations

      A Di-Substituted Boron Dication and Its Hydride-Induced Transformation to an NHC-Stabilized Borabenzene (pages 13293–13297)

      Chao-Tang Shen, Yi-Hung Liu, Prof. Shie-Ming Peng and Prof. Ching-Wen Chiu

      Article first published online: 8 NOV 2013 | DOI: 10.1002/anie.201308385

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      Give me a B: A stepwise chloride abstraction of [Cp*BCl2(IMes)] resulted in the linear di-substituted boron dication [Cp*B(IMes)]2+. The hypercoordinated boron dication, stabilized in the pentagonal pyramidal [C5B]2+ cluster, reacts with superhydride to yield the N-heterocyclic carbene-stabilized borabenzene, [C5Me5B(IMes)] (see scheme).

    23. Supercritical CO2

      Supercritical Carbon Dioxide: A Promoter of Carbon–Halogen Bond Heterolysis (pages 13298–13301)

      Thais Delgado-Abad, Dr. Jaime Martínez-Ferrer, Prof. Dr. Ana Caballero, Dr. Andrea Olmos, Prof. Dr. Rossella Mello, Prof. Dr. María Elena González-Núñez, Prof. Dr. Pedro J. Pérez and Prof. Dr. Gregorio Asensio

      Article first published online: 15 OCT 2013 | DOI: 10.1002/anie.201303819

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      Amazing reaction medium: Supercritical carbon dioxide, with zero dipole moment, lower dielectric constant than pentane, and non-hydrogen-bonding behavior, ionizes carbon–halogen bonds, dissociates the resulting ion pairs, and escapes from capture by the carbocation intermediates at temperatures above 40 °C. These properties allow the observation of carbocation chemistry in the absence of acids.

    24. Synthetic Methods

      Gold-Catalyzed Oxidative Rearrangement Involving 1,2-Acyl Migration: Efficient Synthesis of Functionalized Dihydro-γ-Carbolines from α-(2-Indolyl) Propargylic Alcohols and Imines (pages 13302–13306)

      Lu Wang, Xin Xie and Prof. Yuanhong Liu

      Article first published online: 3 SEP 2013 | DOI: 10.1002/anie.201304700

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      Smooth moves with a nifty side step: A gold-catalyzed transformation of α-(2-indolyl) propargylic alcohols with imines in the presence of the oxidant 8-isopropylquinoline N-oxide provided rapid access to highly functionalized dihydro-γ-carbolines (see scheme). The reaction mechanism is proposed to involve intermolecular trapping of an α-carbonyl gold carbenoid intermediate, followed by cyclization and a novel gold-assisted 1,2-acyl migration.

    25. Dynamic Nuclear Polarization

      Dynamic Nuclear Polarization with Photoexcited Triplet Electrons in a Glassy Matrix (pages 13307–13310)

      Dr. Kenichiro Tateishi, Dr. Makoto Negoro, Dr. Akinori Kagawa and Prof. Dr. Masahiro Kitagawa

      Article first published online: 18 NOV 2013 | DOI: 10.1002/anie.201305674

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      Utilizing photoexcited triplet electrons, dynamic nuclear polarization (DNP) has achieved, in a glassy matrix at 0.40 T and 120 K, a 1H spin polarization of 1.45 %, which is 4250 times larger than the thermal 1H spin polarization. In a glassy matrix, various molecules of interest, including 2,3,4-trifluorobenzoic acid and 5-fluorouracil can be co-doped with polarizing agents; polarizing these co-dopants with DNP was also successful.

    26. Homoallylic Amines

      Palladium(II)-Catalyzed Intramolecular Hydroamination of 1,3-Dienes to Give Homoallylic Amines (pages 13311–13313)

      Justin M. Pierson, Erica L. Ingalls, Richard D. Vo and Prof. Dr. Forrest E. Michael

      Article first published online: 24 OCT 2013 | DOI: 10.1002/anie.201305766

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      A pincer for high selectivity: A mild palladium-catalyzed hydroamination of protected amino-1,3-dienes is possible. This highly regioselective reaction employs a tridentate PNP pincer ligand and leads to cyclic and homoallylic protected amines in high yields. Substrates with a wide array of amine protecting groups and diene substitution patterns were cyclized to form five- and six-membered heterocycles. PG=protecting group.

    27. Surface Functionalization

      Enhanced Reactivity of a Biomimetic Iron(II) α-Keto Acid Complex through Immobilization on Functionalized Gold Nanoparticles (pages 13314–13318)

      Debobrata Sheet, Dr. Partha Halder and Dr. Tapan Kanti Paine

      Article first published online: 18 OCT 2013 | DOI: 10.1002/anie.201305994

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      Immobilized biomimetic iron complex: An iron(II) benzoylformate complex of a thiol-appended N4 ligand immobilized on gold nanoparticles activates dioxygen to carry out oxidative decarboxylation of benzoylformic acid to benzoic acid catalytically.

    28. PET/MRI Agents

      Chelator-Free Synthesis of a Dual-Modality PET/MRI Agent (pages 13319–13323)

      Dr. Feng Chen, Dr. Paul A. Ellison, Christina M. Lewis, Dr. Hao Hong, Dr. Yin Zhang, Sixiang Shi, Reinier Hernandez, Prof.  M. Elizabeth Meyerand, Dr. Todd E. Barnhart and Prof. Weibo Cai

      Article first published online: 24 OCT 2013 | DOI: 10.1002/anie.201306306

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      Old technique, new application: A simple and efficient chelator-free strategy for the synthesis of a novel dual-modality PET/MRI agent has been developed. Labeling of radioarsenic (*AsIII and *AsV, *=71, 72, 74, 76) at the surface of superparamagnetic iron oxide nanoparticles (SPIONs) resulted in *As-SPIONs that can be used for simultaneous PET/MRI in cancer diagnosis, lymph-node mapping, and potentially for internal radiotherapy.

    29. Nitrogen Heterocycles

      Copper-Mediated Synthesis of 1,2,3-Triazoles from N-Tosylhydrazones and Anilines (pages 13324–13328)

      Zhengkai Chen, Qiangqiang Yan, Zhanxiang Liu, Yiming Xu and Prof. Dr. Yuhong Zhang

      Article first published online: 15 OCT 2013 | DOI: 10.1002/anie.201306416

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      NNNifty targets: In a straightforward copper-mediated synthesis of 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles, readily available aniline and N-tosylhydrazone substrates underwent cyclization through C[BOND]N and N[BOND]N bond formation (see scheme; Piv=pivaloyl, Ts=p-toluenesulfonyl). This method enables the preparation of 1,2,3-triazoles with high efficiency under mild conditions without the use of azides.

    30. Cross-Coupling

      Hindered Aryllithium Reagents as Partners in Palladium-Catalyzed Cross-Coupling: Synthesis of Tri- and Tetra-ortho-Substituted Biaryls under Ambient Conditions (pages 13329–13333)

      Massimo Giannerini, Dr. Valentín Hornillos, Dr. Carlos Vila, Dr. Martín Fañanás-Mastral and Prof. Dr. Ben L. Feringa

      Article first published online: 7 NOV 2013 | DOI: 10.1002/anie.201306427

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      Elegant like a butterfly, stings like a lithium reagent: Mono- and di-ortho-substituted aryllithium reagents were coupled through palladium catalysis with hindered aryl bromides to form highly congested tri- and tetra-ortho-substituted biaryls. The reaction allows the use of easily accessible ortho-functionalized aryllithium compounds. The high reactivity of organolithium reagents facilitates a fast process under ambient conditions.

    31. Actinide Zintl Compounds

      You have full text access to this OnlineOpen article
      An Actinide Zintl Cluster: A Tris(triamidouranium)μ3222-Heptaphosphanortricyclane and Its Diverse Synthetic Utility (pages 13334–13337)

      Dr. Dipti Patel, Dr. Floriana Tuna, Prof. Eric J. L. McInnes, Dr. William Lewis, Prof. Alexander J. Blake and Prof. Stephen T. Liddle

      Article first published online: 14 OCT 2013 | DOI: 10.1002/anie.201306492

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      A diuranium(V) arene complex reductively cleaves P4 to give a triuranium heptaphosphanortricyclane cluster (see picture; U green, P purple, N blue, Si orange). This cluster is the first example of a molecular actinide [P7] Zintl complex and the first example of uranium-promoted catenation of P4. This complex undergoes a wide range of reactions under mild conditions to afford liberated P7R3 phosphanortricyclanes.

    32. Heterocycles

      Intramolecular Polar [4+2] Cycloadditions of Aryl-1-aza-2-azoniaallene Salts: Unprecedented Reactivity Leading to Polycyclic Protonated Azomethine Imines (pages 13338–13341)

      Dr. Daniel A. Bercovici, Dr. Jodi M. Ogilvie, Dr. Nikolay Tsvetkov and Prof. Matthias Brewer

      Article first published online: 11 NOV 2013 | DOI: 10.1002/anie.201306553

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      Charged up: In the first example of the title salts undergoing a [4+2] cycloaddition reaction, the azo bond and one aromatic π bond make up the 4π component. This reaction appears to be concerted and provides high yields of protonated azomethine imine products. Substituted alkenes provided products containing all-carbon or nitrogen-bearing quaternary centers in high yield.

    33. Radical Reactions

      Photoredox Transformations with Dimeric Gold Complexes (pages 13342–13345)

      Dr. Guillaume Revol, Terry McCallum, Mathieu Morin, Dr. Fabien Gagosz and Prof. Louis Barriault

      Article first published online: 16 OCT 2013 | DOI: 10.1002/anie.201306727

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      Let the sunshine in! Unactivated alkyl and aryl bromides underwent a light-enabled reductive radical cyclization in the presence of a dimeric phosphine–gold complex as a photocatalyst (see scheme; X=C(CO2Et)2, NR, O). Sunlight can be used as the energy source for this simple and efficient radical reaction, which does not require potentially hazardous and toxic chemical reagents, such as organostannanes and chemical initiators.

    34. Molecular Rectification

      Rectification in Nanoscale Devices Based on an Asymmetric Five-Coordinate Iron(III) Phenolate Complex (pages 13346–13350)

      Lanka D. Wickramasinghe, Meeghage Madusanka Perera, Li Li, Prof. Guangzhao Mao, Prof. Zhixian Zhou and Prof. Cláudio N. Verani

      Article first published online: 14 OCT 2013 | DOI: 10.1002/anie.201306765

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      One-way street: An asymmetric iron(III) phenolate complex with amphiphilic and redox properties was used in the formation of Langmuir–Blodgett (LB) films. These were used as a basis for nanoscale Au|LB film|Au devices that are capable of current rectification.

    35. Carbon-Fiber Memory Devices

      Preparation of Weavable, All-Carbon Fibers for Non-Volatile Memory Devices (pages 13351–13355)

      Dr. Gengzhi Sun, Dr. Juqing Liu, Prof. Lianxi Zheng, Prof. Wei Huang and Prof. Hua Zhang

      Article first published online: 5 NOV 2013 | DOI: 10.1002/anie.201306770

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      Woven into your memories: Aligned multi-walled carbon nanotube (MWCNT) fibers are coated by a thin layer of graphene oxide (GO). The MWCNT fibers work as the top and bottom electrodes while the GO acts as the active layer. By simply cross-stacking two MWCNT@GO fibers, the memory cell obtained shows a write-once-read-many-times effect (see picture).

    36. C[BOND]H Functionalization

      Enantioselective Palladium(II) Phosphate Catalyzed Three-Component Reactions of Pyrrole, Diazoesters, and Imines (pages 13356–13360)

      Dan Zhang, Huang Qiu, Dr. Liqin Jiang, Fengping Lv, Chaoqun Ma and Prof. Dr. Wenhao Hu

      Article first published online: 4 NOV 2013 | DOI: 10.1002/anie.201306824

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      Reaction trio: The title reaction delivers C[BOND]H functionalized pyrrole derivatives in moderate to good yields. This novel three-component reaction provides both syn- and anti-pyrrole derivatives having two contiguous stereocenters with good regio-, diastereo-, and enantioselectivity. This process represents the first highly enantioselective palladium-carbenoid-mediated reaction.

    37. Strained Metallacycles

      Synthesis of Five-Membered Osmacycloallenes and Conversion into Six-Membered Osmacycloallenes (pages 13361–13364)

      Tongdao Wang, Dr. Jun Zhu, Feifei Han, Chen Zhou, Hanyu Chen, Dr. Hong Zhang and Prof. Dr. Haiping Xia

      Article first published online: 16 OCT 2013 | DOI: 10.1002/anie.201306911

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      Highly stable five-membered metallacycloallenes were synthesized under mild conditions. Calculations revealed that the incorporation of transition-metal moieties relieves considerable strain and indicates a trend toward ring enlargement in the five-membered metallacycloallenes. Conversion into six-membered metallacycloallenes was confirmed experimentally.

    38. Asymmetric Synthesis

      Palladium-Catalyzed Asymmetric Hydrogenolysis of N-Sulfonyl Aminoalcohols via Achiral Enesulfonamide Intermediates (pages 13365–13368)

      Dr. Chang-Bin Yu and Prof. Yong-Gui Zhou

      Article first published online: 12 NOV 2013 | DOI: 10.1002/anie.201307036

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      Giving the cat complete control: A stereoconvergent formal hydrogenolysis of N-sulfonyl aminoalcohols in the presence of a chiral Pd catalyst and trifluoroacetic acid (TFA) gave chiral amines with two contiguous stereocenters (see scheme; TFE=trifluoroethanol, Ts=p-tosyl). The products were formed with up to 94 % ee by acid-catalyzed dehydration to afford an enesulfonamide, enamine/imine isomerization, and Pd-catalyzed asymmetric hydrogenation.

    39. Molecular Dynamics

      Controlling and Predicting Crystal Shapes: The Case of Urea (pages 13369–13372)

      Dr. Matteo Salvalaglio, Dr. Thomas Vetter, Prof. Dr. Marco Mazzotti and Prof. Dr. Michele Parrinello

      Article first published online: 24 OCT 2013 | DOI: 10.1002/anie.201304562

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      Understanding crystal growth from solution is crucial to control the evolution of crystal morphologies. Experiments, molecular simulations, and theory were combined to examine the morphology of urea crystals grown in different solutions. To get a rational representation of all the possible habits a shape diagram (see picture) is introduced in which the habit dependence on the relative growth rates is illustrated.

    40. Natural Product Synthesis

      Total Synthesis and Biological Evaluation of Jerantinine E (pages 13373–13376)

      Dr. Reto Frei, Davide Staedler, Aruna Raja, Dr. Raimo Franke, Dr. Florenz Sasse, Dr. Sandrine Gerber-Lemaire and Prof. Dr. Jérôme Waser

      Article first published online: 14 OCT 2013 | DOI: 10.1002/anie.201305533

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      Nature's beauty: The first total synthesis of the alkaloid natural product jerantinine E is based on a selective cyclization of an aminocyclopropane. Preliminary investigations show that it inhibits the polymerization of tubulin, displaying significant cytotoxicity and antimigratory activity against both breast and lung cancer cell lines.

    41. Electrochromic Materials

      Facile Deposition of Multicolored Electrochromic Metal–Organic Framework Thin Films (pages 13377–13381)

      Dr. Casey R. Wade, Minyuan Li and Prof. Mircea Dincă

      Article first published online: 16 OCT 2013 | DOI: 10.1002/anie.201306162

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      Metal–organic frameworks: The solvothermal reaction of Zn2+ ions and bis- (pyrazolyl)naphthalene diimide readily affords strongly adhering, electroactive metal–organic framework thin films on conductive glass substrates (see picture). Electrochemical cycling of these films followed by in situ UV/Vis spectroscopy reveals striking multicolored electrochromic responses.

    42. Zeolites

      Intergrowth Structure and Aluminium Zoning of a Zeolite ZSM-5 Crystal as Resolved by Synchrotron-Based Micro X-Ray Diffraction Imaging (pages 13382–13386)

      Zoran Ristanović, Dr. Jan P. Hofmann, Dr. Upakul Deka, Dr. Tobias U. Schülli, Dr. Marcus Rohnke, Dr. Andrew M. Beale and Prof. Dr. Ir. Bert M. Weckhuysen

      Article first published online: 15 OCT 2013 | DOI: 10.1002/anie.201306370

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      Crystallographic microscopy: Zeolite ZSM-5 is one of the most used solid acid catalysts in the oil refining and chemical industries. Synchrotron-based micro X-ray diffraction imaging has been used to spatially resolve the internal crystallographic 3D architecture of ZSM-5 intergrowths and to visualize the zoning of aluminium at the single-catalyst-particle level.

    43. Nanomaterials

      Charged Metallopolymers as Universal Precursors for Versatile Cobalt Materials (pages 13387–13391)

      Jiuyang Zhang, Dr. Yi Yan, Michael W. Chance, Dr. Jihua Chen, Jeffery Hayat, Dr. Shuguo Ma and Prof. Dr. Chuanbing Tang

      Article first published online: 16 OCT 2013 | DOI: 10.1002/anie.201306432

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      A facile phase-transfer ion-exchange strategy was used to prepare cationic cobaltocenium-containing polyelectrolytes with different counterions. These cobalt-containing polymers were used to prepare cobalt-based materials, including cobalt metal, cobalt phosphide, cobalt monoxide, cobalt–iron hybrids, and cobalt ferrite. Block copolymers and polymer brushes were also used to prepare cobalt-based nanoparticles and nanowires.

    44. Ionic Liquids

      Distillable Ionic Liquids: Reversible Amide O Alkylation (pages 13392–13396)

      Dr. Zheng-Jian Chen, Dr. Hong-Wei Xi, Prof. Kok Hwa Lim and Prof. Jong-Min Lee

      Article first published online: 31 OCT 2013 | DOI: 10.1002/anie.201306476

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      Put it in reverse: The recycling of ionic liquids (ILs) by distillation of the regenerated volatile precursors was demonstrated to be feasible by using low-cost amide-cation-derived aprotic ionic liquids prepared from reversible O alkylation. The low viscosity (21.6 cP at 25 °C), high conductivity (15.45 mS cm−1 at 25 °C), and wide electrochemical windows (ca. 4.5 V) of the ILs show potential for electrochemical applications.

      Corrected by:

      Corrigendum: Corrigendum: Distillable Ionic Liquids: Reversible Amide O Alkylation

      Vol. 53, Issue 40, 10567, Article first published online: 22 SEP 2014

    45. Synthetic Biology

      A Remarkable Self-Organization Process as the Origin of Primitive Functional Cells (pages 13397–13400)

      M. Sc. Pasquale Stano, M. Sc. Erica D'Aguanno, Prof. Dr. Jürgen Bolz, Prof. Dr. Alfred Fahr and Prof. Dr. Pier Luigi Luisi

      Article first published online: 15 OCT 2013 | DOI: 10.1002/anie.201306613

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      Encapsulation: The emergence of primitive cells remains an enigma of the origin of life. By modeling this key process as the encapsulation of a complex multimolecular mixture inside liposomes, a remarkable self-organization process has been revealed that brings about solute-rich compartments in which protein synthesis can take place.

    46. Light-up Probes

      Contact-Mediated Quenching for RNA Imaging in Bacteria with a Fluorophore-Binding Aptamer (pages 13401–13404)

      Dr. Murat Sunbul and Prof. Dr. Andres Jäschke

      Article first published online: 16 OCT 2013 | DOI: 10.1002/anie.201306622

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      Bind and shine: Sulforhodamine B was converted into a very efficient fluorescence turn-on probe exclusively by contact quenching. The fluorescence of the probe increases more than 100-fold upon binding to a sulforhodamine-binding RNA aptamer (SRB-2). The probe and the SRB-2 aptamer were used to monitor transcriptions in real-time and to image RNA in live bacteria.

    47. RNA-Binding Agents

      Structure-Based Design of an RNA-Binding p-Terphenylene Scaffold that Inhibits HIV-1 Rev Protein Function (pages 13405–13409)

      Luis González-Bulnes, Ignacio Ibáñez, Dr. Luis M. Bedoya, Manuela Beltrán, Dr. Silvia Catalán, Dr. José Alcamí, Prof. Santos Fustero and Dr. José Gallego

      Article first published online: 8 NOV 2013 | DOI: 10.1002/anie.201306665

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      Rev(ersing) RNA binding: RNA-binding inhibitors based on a bilaterally substituted p-terphenylene scaffold (green) project their substituents in a broad spatial angle and reproduce the interactions of a protein α-helix (red) embedded in its RNA receptor. These terphenyls can mimic one α-helix of the HIV-1 protein Rev and inhibit Rev function and HIV-1 replication in cells. This scaffold may open new avenues for targeting nucleic acids with small molecules.

    48. Synthetic Transcription Activators

      A Synthetic Small Molecule for Targeted Transcriptional Activation of Germ Cell Genes in a Human Somatic Cell (pages 13410–13413)

      Le Han, Ganesh N. Pandian, Syed Junetha, Shinsuke Sato, Chandran Anandhakumar, Junichi Taniguchi, Abhijit Saha, Toshikazu Bando, Hiroki Nagase and Prof. Hiroshi Sugiyama

      Article first published online: 18 OCT 2013 | DOI: 10.1002/anie.201306766

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      Germ cell gene switch: The dynamic epigenome coordinates the timely genome-wide transcriptional activation that governs interindividual diversity, for example, in germ cells, which differ from somatic cells through their ability to undergo meiosis. Now, an epigenetically active synthetic small molecule can trigger unusual activation of the typically conserved PIWI gene that regulates the meiotic process in a human somatic cell.

    49. Noncovalent Porous Materials

      Permanent Porosity Derived From the Self-Assembly of Highly Luminescent Molecular Zinc Carbonate Nanoclusters (pages 13414–13418)

      Kamil Sokołowski, Dr. Wojciech Bury, Dr. Iwona Justyniak, Dr. David Fairen-Jimenez, Katarzyna Sołtys, Dr. Daniel Prochowicz, Dr. Sihai Yang, Prof. Martin Schröder and Prof. Janusz Lewiński

      Article first published online: 14 OCT 2013 | DOI: 10.1002/anie.201306785

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      Hungry hungry micropores: Reaction of [Zn43-OH)2(L)4(tBu)2] (LH=8-hydroxyquinoline) with CO2 forms a 3D microporous material with spherical zinc carbonate nanoclusters packed in a diamondoid manner in the solid state. This compound exhibits one of the highest Brunauer—Emmett—Teller surface areas for a noncovalent porous material, with high H2, CO2, and CH4 uptake.

    50. Multishell Nanostructures

      Upconverting Near-Infrared Light through Energy Management in Core–Shell–Shell Nanoparticles (pages 13419–13423)

      Dr. Hongli Wen, Hai Zhu, Xian Chen, Tak Fu Hung, Beilei Wang, Prof. Guangyu Zhu, Prof. Siu Fung Yu and Prof. Feng Wang

      Article first published online: 16 OCT 2013 | DOI: 10.1002/anie.201306811

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      Blue emission at NIR excitation: A strategy, based on energy management in nanostructured materials, is reported for photon upconversion of near-infrared light. Several optical processes can be integrated into a single nanoparticle (see picture). The effect offers upconversion emissions spanning from ultraviolet to the visible spectral region by excitation at 808 nm.

    51. Organocatalysis

      Thiophosphoramide-Based Cooperative Catalysts for Brønsted Acid Promoted Ionic Diels–Alder Reactions (pages 13424–13428)

      Alina Borovika, Pui-In Tang, Seth Klapman and Prof. Dr. Pavel Nagorny

      Article first published online: 18 OCT 2013 | DOI: 10.1002/anie.201307133

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      Three's a crowd: The combination of a Brønsted acid and a hydrogen-bond donor cocatalyst was found to promote various ionic [2+4] cycloadditions under mild reaction conditions (see scheme; Ts=4-toluenesulfonyl). Thiophosphoramides are the most effective cocatalysts because of the stronger counterion activation effect resulting from three, rather than two, hydrogen bonds involved in anion binding.

    52. Optical Chemical Sensor

      A Noble-Metal-Free Porous Coordination Framework with Exceptional Sensing Efficiency for Oxygen (pages 13429–13433)

      Rui-Biao Lin, Fang Li, Si-Yang Liu, Xiao-Lin Qi, Prof. Dr. Jie-Peng Zhang and Prof. Dr. Xiao-Ming Chen

      Article first published online: 16 OCT 2013 | DOI: 10.1002/anie.201307217

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      Light material: By virtue of the unique framework structure and very high oxygen permeability, a noble-metal-free, highly fluorescent, porous coordination polymer demonstrates a rapid, reversible, efficient, stable, and selective fluorescence-quenching response toward oxygen.

    53. Carborane Clusters

      Variable Photophysical Properties of Phosphorescent Iridium(III) Complexes Triggered by closo- and nido-Carborane Substitution (pages 13434–13438)

      Chao Shi, Huibin Sun, Xiao Tang, Wen Lv, Prof. Dr. Hong Yan, Qiang Zhao, Jingxia Wang and Wei Huang

      Article first published online: 16 OCT 2013 | DOI: 10.1002/anie.201307333

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      Phosphorescent iridium(III) complexes with three bidentate carborane-functionalized ligands have been synthesized. The luminescent efficiency of the o-carborane-based facial complex fac-o shows solvent-molecule dependence both in solution and solid state that is related to the dielectric constant. The water-soluble and high phosphorescence-efficient nido complex nido-fac-o can be used in fluorescence lifetime bioimaging.

    54. Synthetic Receptors

      Bidirectional Regulation of Halide Binding in a Heterometallic Supramolecular Cube (pages 13439–13443)

      William J. Ramsay, Dr. Tanya K. Ronson, Dr. Jack K. Clegg and Dr. Jonathan R. Nitschke

      Article first published online: 14 NOV 2013 | DOI: 10.1002/anie.201307478

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      Complex cubes: In a cationic supramolecular cube, coordinatively unsaturated metal centers in the walls of the host provided binding sites for neutral or negatively charged guests. The binding of an initial guest (CF3CO2, OPMe3, NH3, or NMe3) either cooperatively enhanced or competitively inhibited the binding of a second guest (halide ion).

    55. Polyhalogen Anions

      An Adaptable and Dynamically Porous Organic Salt Traps Unique Tetrahalide Dianions (pages 13444–13448)

      Dr. Javier Martí-Rujas, Dr. Lorenzo Meazza, Dr. Gin Keat Lim, Dr. Giancarlo Terraneo, Dr. Tullio Pilati, Prof. Dr. Kenneth D. M. Harris, Prof. Dr. Pierangelo Metrangolo and Prof. Dr. Giuseppe Resnati

      Article first published online: 7 NOV 2013 | DOI: 10.1002/anie.201307552

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      Bis(I2) adducts of hexamethonium dihalides are pre-organized to respond dynamically to heating and reach a functional structure that favors the formation of the poorly stable and virtually unknown [I2Br2]2− and [I2Cl2]2− tetrahalides which could not be obtained in solution (see picture). The cavity-directed reactivity affords new opportunities for synthesis and interconversion of polyhalogen anions.

    56. OLED Triplet Emitters

      Metal-Free OLED Triplet Emitters by Side-Stepping Kasha’s Rule (pages 13449–13452)

      Dr. Debangshu Chaudhuri, Dr. Eva Sigmund, Annemarie Meyer, Lisa Röck, Philippe Klemm, Sebastian Lautenschlager, Agnes Schmid, Shane R. Yost, Prof. Dr. Troy Van Voorhis, Dr. Sebastian Bange, Prof. Dr. Sigurd Höger and Prof. Dr. John M. Lupton

      Article first published online: 7 NOV 2013 | DOI: 10.1002/anie.201307601

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      Keeping it light: Most organic fluorophores do not show useful emission from the triplet excited state. A new class of materials is presented for organic light-emitting diodes that exhibit phosphorescence under electrical excitation, even at room temperature, without employing the heavy-atom effect. Blocking of internal conversion is so effective that emission from higher-lying triplet states, above the singlet, can be observed at low temperature.

    57. Flexible Materials

      A Highly Stretchable, Fiber-Shaped Supercapacitor (pages 13453–13457)

      Zhibin Yang, Jue Deng, Xuli Chen, Jing Ren and Prof. Huisheng Peng

      Article first published online: 8 NOV 2013 | DOI: 10.1002/anie.201307619

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      Superstretchy: A supercapacitor with high stretchability has been developed by wrapping two layers of sheets built of aligned carbon nanotubes, which serve as two electrodes, on an elastic fiber. The use of these sheets offers high flexibility, tensile strength, electrical conductivity, and mechanical and thermal stability. The supercapacitor shows and maintains a high specific capacitance after stretching for many cycles.

    58. Polymer Materials

      Seawater Uranium Sorbents: Preparation from a Mesoporous Copolymer Initiator by Atom-Transfer Radical Polymerization (pages 13458–13462)

      Dr. Yanfeng Yue, Dr. Richard T. Mayes, Dr. Jungseung Kim, Dr. Pasquale F. Fulvio, Dr. Xiao-Guang Sun, Dr. Costas Tsouris, Dr. Jihua Chen, Dr. Suree Brown and Prof. Dr. Sheng Dai

      Article first published online: 31 OCT 2013 | DOI: 10.1002/anie.201307825

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      From the sea to the reactor: Nanoporous template-free initiators for atom-transfer radical polymerization (ATRP) were synthesized with surface and framework initiator sites and tailorable pore structures. Polyacrylonitrile grown on one initiator was converted into polyamidoxime to generate a uranium sorbent for seawater extraction with a high uptake rate and capacity relative to those of nonwoven irradiation-grafted polyethylene-fiber composites.

    59. Proton Hopping in Crystals

      Proton Cascade in a Molecular Solid: H/D Exchange on Mobile and Immobile Water (pages 13463–13467)

      Dr. Silvia C. Capelli, Prof. Larry R. Falvello, Elena Forcén-Vázquez, Prof. Garry J. McIntyre, Prof. Fernando Palacio, Dr. Sergio Sanz and Dr. Milagros Tomás

      Article first published online: 7 NOV 2013 | DOI: 10.1002/anie.201307994

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      Working without pores: In non-porous, channel-free crystals of a manganese citrate coordination polymer, neutron diffraction reveals that the water molecules, both metal-bound and co-crystallized, undergo full hydrogen/deuterium exchange. Neutron diffraction analyses show a pattern of hydrogen disorder that can be interpreted in terms of the Grotthuss proton-cascade mechanism (see scheme).

    60. Heterocycles

      You have full text access to this OnlineOpen article
      Gold-Catalyzed Synthesis of Tetrazoles from Alkynes by C[BOND]C Bond Cleavage (pages 13468–13471)

      Morgane Gaydou and Prof. Antonio M. Echavarren

      Article first published online: 13 NOV 2013 | DOI: 10.1002/anie.201308076

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      Golden duality: Tetrazoles are formed by the reaction of alkynes with TMSN3 (TMS=trimethylsilyl) in the presence of iPrOH and the gold(I) catalyst [JohnPhosAu(MeCN)]SbF6. In this transformation gold plays a dual role, first activating the alkyne and then generating a Brønsted acid in situ.

    61. Gold Photochemistry

      Approaching White-Light Emission from a Phosphorescent Trinuclear Gold(I) Cluster by Modulating Its Aggregation Behavior (pages 13472–13476)

      Dr. Wen-Xiu Ni, Mian Li, Ji Zheng, Dr. Shun-Ze Zhan, Yu-Min Qiu, Prof. Dr. Seik Weng Ng and Prof. Dr. Dan Li

      Article first published online: 19 NOV 2013 | DOI: 10.1002/anie.201308135

      Thumbnail image of graphical abstract

      White light: [{Au(L)}3] (L=3-(2-thienyl)pyrazolate) gives dual emission, one from an organic chromophore the other from aurophilic stacking interactions. The resulting blue–green and orange–red emissions can be tuned to approach white-light by modulating the aggregation behavior of the cluster.

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