Angewandte Chemie International Edition

Cover image for Vol. 53 Issue 17

Early View (Online Version of Record published before inclusion in an issue)

Editor: Peter Gölitz, Deputy Editors: Neville Compton, Haymo Ross

Online ISSN: 1521-3773

Associated Title(s): Angewandte Chemie, Chemistry - A European Journal, Chemistry – An Asian Journal, Zeitschrift für Chemie

  1. Communications

    1. Iron–Sulfur Clusters

      Low-Spin Pseudotetrahedral Iron(I) Sites in Fe2(μ-S) Complexes

      John S. Anderson and Prof. Jonas C. Peters

      Article first published online: 17 APR 2014 | DOI: 10.1002/anie.201401018

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      A new spin on FeI:FeI centers: A unique series of diiron [(L3Fe)2(μ-S)] complexes were isolated and characterized in the low-valent oxidation states FeII[BOND]S[BOND]FeII, FeII[BOND]S[BOND]FeI, and FeI[BOND]S[BOND]FeI as nearly isostructural but electronically distinct species. Structural, magnetic, and spectroscopic studies indicated a transition of the pseudotetrahedral iron centers to low-spin S=1/2 states upon reduction from FeII to FeI (see scheme).

    2. Synthetic Methods

      A Biomimetic Catalytic Aerobic Functionalization of Phenols

      Kenneth Virgel N. Esguerra, Dr. Yacoub Fall and Prof. Jean-Philip Lumb

      Article first published online: 17 APR 2014 | DOI: 10.1002/anie.201311103

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      The direct approach: Polyfunctional aromatic rings have been generated by direct functionalization of C[BOND]H bonds to C[BOND]O, C[BOND]N, and C[BOND]S bonds at the sole expense of reducing O2 to H2O. The method hinges on a regio- and chemoselective, copper-catalyzed aerobic oxygenation of phenols to provide ortho-quinones (see scheme), thus mimicking the ubiquitous biosynthetic pathway of melanogenesis.

    3. Mass Spectrometry

      On-Line Reaction Monitoring and Mechanistic Studies by Mass Spectrometry: Negishi Cross-Coupling, Hydrogenolysis, and Reductive Amination

      Xin Yan, Ewa Sokol, Dr. Xin Li, Guangtao Li, Dr. Shiqing Xu and Prof. R. Graham Cooks

      Article first published online: 17 APR 2014 | DOI: 10.1002/anie.201310493

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      Fast and simple: A reaction monitoring system based on inductive ESI mass spectrometry provides a fast and simple way to monitor chemical reactions, including air-/moisture-sensitive reactions, continuously. It also provides information on solution-phase organic reaction mechanisms as shown by the observation of short-lived intermediates in Pd/C-catalyzed hydrogenolysis and several intermediates in Negishi cross-coupling reactions.

    4. Reactive Intermediates

      Nucleophilic Reactivity of a Copper(II)–Superoxide Complex

      Paolo Pirovano, Adriana M. Magherusan, Ciara McGlynn, Andrew Ure, Amy Lynes and Dr. Aidan R. McDonald

      Article first published online: 17 APR 2014 | DOI: 10.1002/anie.201311152

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      Nucleophilic superoxide: A copper(II)-superoxide complex has been found to be a highly reactive nucleophile. The complex reacts readily with certain electrophiles and is capable of the nucleophilic deformylation of electron-rich aldehydes (Baeyer–Villiger oxidation). These observations provide experimental support for the postulated nucleophilic reactivity of metal-superoxide intermediates in the catalytic cycles of certain nonheme iron enzymes.

    5. Chirality in Complexes

      Aza[6]helicene Platinum Complexes: Chirality Control of cis–trans Isomerism

      Daniele Mendola, Dr. Nidal Saleh, Dr. Nicolas Vanthuyne, Prof. Christian Roussel, Dr. Loïc Toupet, Dr. Franca Castiglione, Prof. Tullio Caronna, Prof. Andrea Mele and Dr. Jeanne Crassous

      Article first published online: 17 APR 2014 | DOI: 10.1002/anie.201401004

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      Controlled by the ligand: The cis and trans isomerism in the complex [PtIICl2(4-aza[6]helicene)PPh3] is unexpectedly controlled by the racemic and enantiopure forms of the starting 4-aza[6]helicene ligand.

    6. Bioimaging | Hot Paper

      DNA Nanoflowers for Multiplexed Cellular Imaging and Traceable Targeted Drug Delivery

      Rong Hu, Prof. Xiaobing Zhang, Dr. Zilong Zhao, Dr. Guizhi Zhu, Dr. Tao Chen, Ting Fu and Prof. Weihong Tan

      Article first published online: 17 APR 2014 | DOI: 10.1002/anie.201400323

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      Colorful technique: A facile approach for making aptamer-conjugated FRET nanoflowers (NFs) by rolling circle replication for single-excitation multiplexed imaging and traceable targeted drug delivery was reported. NF assembly is independent of template sequences, avoiding the complicated design of DNA base-pairing in conventional nanostructure assembly.

    7. Stimulated Raman Scattering

      Live-Cell Stimulated Raman Scattering Imaging of Alkyne-Tagged Biomolecules

      Senlian Hong, Tao Chen, Yuntao Zhu, Ang Li, Prof. Yanyi Huang and Prof. Xing Chen

      Article first published online: 17 APR 2014 | DOI: 10.1002/anie.201400328

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      Raman imaging: In addition to the clickable chemical reactivity, alkynes possess a unique Raman scattering within the Raman-silent region of a cell (see picture). Coupling this spectroscopic signature with Raman microscopy yields a new imaging modality beyond fluorescence and label-free microscopies.

    8. Amide Activation | Very Important Paper

      Chemoselective Intermolecular α-Arylation of Amides

      Dr. Bo Peng, Dr. Danny Geerdink, Dr. Christophe Farès and Prof. Dr. Nuno Maulide

      Article first published online: 16 APR 2014 | DOI: 10.1002/anie.201402229

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      Arylating me softly: A new approach for the fully chemoselective α-arylation of amides has been developed. When electrophilic amide activation is employed, aryl groups can be regioselectively introduced in the position α- to the amide, and that even in the presence of esters or alkyl ketones. Mechanistic studies emphasize a remarkably subtle base effect in this transformation.

    9. Organophotocatalysis

      Enantioselective Organo-Photocatalysis Mediated by Atropisomeric Thiourea Derivatives

      Nandini Vallavoju, Dr. Sermadurai Selvakumar, Dr. Steffen Jockusch, Prof. Dr. Mukund P. Sibi and Prof. Dr. Jayaraman Sivaguru

      Article first published online: 16 APR 2014 | DOI: 10.1002/anie.201310940

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      Organo-photocatalysts that are based on atropisomeric thioureas and display lower excited-state energies than the reactive substrates have been developed. These photocatalysts were found to be efficient in promoting the [2+2] photocycloaddition of 4-alkenyl-substituted coumarins, which led to the corresponding products with high enantioselectivity (77–96 % ee) at low catalyst loading (1–10 mol %).

    10. Drug Delivery | Very Important Paper

      Sequential Intra-Intercellular Nanoparticle Delivery System for Deep Tumor Penetration

      Dr. Caoyun Ju, Dr. Ran Mo, Jingwei Xue, Lei Zhang, Zekai Zhao, Dr. Lingjing Xue, Prof. Qineng Ping and Dr. Can Zhang

      Article first published online: 16 APR 2014 | DOI: 10.1002/anie.201311227

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      Special delivery: A nanoparticle delivery system consisting of a reversible swelling–shrinking nanogel allows deep tumor penetration of chemotherapeutics. It shows efficient drug release and intracellular trafficking to kill cancer cells, and after being released from the dead cells, can continue infecting neighboring cancer cells closer to the center of the tumor.

    11. Thermoresponsive Membranes

      Temperature-Modulated Water Filtration Using Microgel-Functionalized Hollow-Fiber Membranes

      Daniel Menne, Fee Pitsch, Dr. John E. Wong, Prof. Andrij Pich and Prof. Matthias Wessling

      Article first published online: 16 APR 2014 | DOI: 10.1002/anie.201400316

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      Hollow-fiber membranes can be modified in a straightforward fashion with thermoresponsive microgels when the microgels are infiltrated into the porous structure of the membrane in dead-end mode at constant flux. The resulting membranes show thermoresponsive properties in terms of resistance and retention.

    12. Molecular Imaging

      DNA-Templated Assembly of a Heterobivalent Quantum Dot Nanoprobe For Extra- and Intracellular Dual-Targeting and Imaging of Live Cancer Cells

      Wei Wei, Xuewen He and Prof. Nan Ma

      Article first published online: 16 APR 2014 | DOI: 10.1002/anie.201400428

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      Put two and two together: Two spatially isolated cancer markers (nucleolin and mRNA) present on the cell surface and in cell cytosol, respectively, have been targeted with a DNA-templated heterobivalent quantum dot (QD) nanoprobe. Fluorescence resonance energy transfer based confocal microscopy allows imaging and unambiguous signal deconvolution of the mRNA-targeting QD nanoprobes inside cancer cells.

    13. Protein Aggregation | Hot Paper

      Co-existence of Two Different α-Synuclein Oligomers with Different Core Structures Determined by Hydrogen/Deuterium Exchange Mass Spectrometry

      Dr. Wojciech Paslawski, Simon Mysling, Karen Thomsen, Dr. Thomas J. D. Jørgensen and Prof. Dr. Daniel E. Otzen

      Article first published online: 16 APR 2014 | DOI: 10.1002/anie.201400491

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      On-pathway or off-pathway? α-Synuclein oligomers are widely accepted to be cytotoxic species in Parkinson’s disease. There is debate as to whether they are intermediate species of fibril formation or the distinct end product of aggregation. Data indicate that both are correct and two different types of α-synuclein oligomers are formed: one that can be elongated by monomers and form fibrils and a second that stacks together to form more amorphous structures.

    14. Synthetic Methods

      CO/C-H as an Acylating Reagent: A Palladium-Catalyzed Aerobic Oxidative Carbonylative Esterification of Alcohols

      Lu Wang, Yanxia Wang, Dr. Chao Liu and Prof. Aiwen Lei

      Article first published online: 16 APR 2014 | DOI: 10.1002/anie.201400612

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      New choice: A palladium-catalyzed oxidative carbonylative esterification of a variety of functionalized alcohols under base- and ligand-free conditions is demonstrated, and a CO/olefin combination is utilized as the acylating reagent with O2 as a benign oxidant. Notably, scope of the substrate alcohols has been greatly broadened.

    15. Organ Repair | Hot Paper

      You have full text access to this OnlineOpen article
      Organ Repair, Hemostasis, and In Vivo Bonding of Medical Devices by Aqueous Solutions of Nanoparticles

      Prof. Dr. Anne Meddahi-Pellé , Aurélie Legrand, Dr. Alba Marcellan , Liliane Louedec, Prof. Dr. Didier Letourneur and Prof. Dr. Ludwik Leibler

      Article first published online: 16 APR 2014 | DOI: 10.1002/anie.201401043

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      Nanobridging is obtained by spreading a drop of aqueous nanoparticle solution on a wound edge and bringing edges into contact. In less than a minute, a strong closure and hemostasis can be achieved even within a wet and dynamic environment. Nanoparticle solutions can be also used to attach medical devices to organs.

    16. Anti-Aging Membranes

      Ending Aging in Super Glassy Polymer Membranes

      Dr. Cher Hon Lau, Dr. Phuc Tien Nguyen, Dr. Matthew R. Hill, Dr. Aaron W. Thornton, Dr. Kristina Konstas, Dr. Cara M. Doherty, Dr. Roger J. Mulder, Dr. Laure Bourgeois, Dr. Amelia C. Y. Liu, Dr. David J. Sprouster, Prof. James P. Sullivan, Dr. Timothy J. Bastow, Dr. Anita J. Hill, Prof. Douglas L. Gin and Prof. Richard D. Noble

      Article first published online: 16 APR 2014 | DOI: 10.1002/anie.201402234

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      Forever young: Like stringed beads, polymer chains of a permeable membrane are intercalated within the pores of PAF-1 particles thus inhibiting polymer chain relaxation and stopping aging. PAF-1 incorporation also drastically enhanced gas permeabilities (see picture).

    17. Asymmetric Catalysis

      Direct Catalytic Asymmetric Vinylogous Conjugate Addition of Unsaturated Butyrolactones to α,β-Unsaturated Thioamides

      Dr. Liang Yin, Dr. Hisashi Takada, Shaoquan Lin, Dr. Naoya Kumagai and Prof. Dr. Masakatsu Shibasaki

      Article first published online: 16 APR 2014 | DOI: 10.1002/anie.201402332

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      Soft spot: Soft Lewis acid/Brønsted base cooperative catalysts have enabled the title reaction of α,β- and β,γ-unsaturated butyrolactones with perfect atom economy. When using α-angelica lactone and its derivatives as pronucleophiles, a 0.5 mol % catalyst loading was sufficient to complete the reaction to construct consecutive tri- and tetrasubstituted stereogenic centers in a highly diastereo- and enantioselective fashion.

    18. Coil–Helix Transition

      Unravelling Secondary Structure Changes on Individual Anionic Polysaccharide Chains by Atomic Force Microscopy

      Larissa Schefer, Dr. Jozef Adamcik and Prof. Dr. Raffaele Mezzenga

      Article first published online: 16 APR 2014 | DOI: 10.1002/anie.201402855

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      The coil–helix transition within single chains of anionic carrageenan polysaccharides is resolved in situ by atomic force microscopy, as a result of the presence of monovalent ions close to physiological conditions (see picture). Polymer statistical analysis demonstrates a modulation of the rigidity and topological features of individual polyelectrolyte chains upon this conformational change.

    19. Energy Conversion

      A Twisted Wire-Shaped Dual-Function Energy Device for Photoelectric Conversion and Electrochemical Storage

      Hao Sun, Xiao You, Jue Deng, Xuli Chen, Zhibin Yang, Peining Chen, Xin Fang and Prof. Huisheng Peng

      Article first published online: 16 APR 2014 | DOI: 10.1002/anie.201403168

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      Twisted: A wire-shaped energy device that can perform photoelectric conversion and electrochemical storage was developed through a simple but effective twisting process. The energy wire exhibited a high energy conversion efficiency of 6.58 % and specific capacitance of 85.03 μF cm−1 or 2.13 mF cm−2, and the two functions were alternately realized without sacrificing either performance.

    20. Photoredox Catalysis

      Visible-Light-Induced Photoredox Catalysis with a Tetracerium-Containing Silicotungstate

      Dr. Kosuke Suzuki, Fei Tang, Dr. Yuji Kikukawa, Dr. Kazuya Yamaguchi and Prof. Dr. Noritaka Mizuno

      Article first published online: 16 APR 2014 | DOI: 10.1002/anie.201403215

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      Cerium, silicon, tungsten: Intramolecular CeIII-to-POM(WVI) charge transfer is observed when the tetranuclear cerium(III)-containing silicotungstate CePOM is irradiated with visible light (λ>400 nm; POM=polyoxometalate). This enabled the photocatalytic oxidative dehydrogenation of primary and secondary amines as well as the α-cyanation of tertiary amines in the presence of O2 (1 atm) as the sole oxidant.

  2. Cover Pictures

    1. Evidence for Extensive Single-Electron-Transfer Chemistry in Boryl Anions: Isolation and Reactivity of a Neutral Borole Radical

      Dr. Rüdiger Bertermann, Prof. Dr. Holger Braunschweig, Dr. Rian D. Dewhurst, Dipl.-Chem. Christian Hörl, Dipl.-Chem. Thomas Kramer and Dr. Ivo Krummenacher

      Article first published online: 16 APR 2014 | DOI: 10.1002/anie.201403558

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      The isolation and synthetic implications of the first isolated neutral borole radical are described by H. Braunschweig et al. in their Communication (DOI: 10.1002/anie.201402556). What appears at first to be boron-centered nucleophilicity was shown to be single-electron-transfer (SET; i.e. radical) reactivity when a neutral borole radical is isolated both as a final product and as an intermediate in the reaction of borole anions with triorganyl halides of tin and lead.

  3. Communications

    1. Photocathodes

      Aqueous-Solution Route to Zinc Telluride Films for Application to CO2 Reduction

      Dr. Ji-Wook Jang, Dr. Seungho Cho, Dr. Ganesan Magesh, Youn Jeong Jang, Dr. Jae Young Kim, Won Yong Kim, Prof. Jeong Kon Seo, Prof. Sungjee Kim, Prof. Kun-Hong Lee and Prof. Jae Sung Lee

      Article first published online: 16 APR 2014 | DOI: 10.1002/anie.201310461

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      High performance without sacrifice: Zinc-blende zinc telluride (ZnTe) was directly formed on a Zn/ZnO-nanowire substrate by a simple dissolution–recrystallization mechanism without a surfactant. The ZnTe electrode was applied as a photocathode for CO2 reduction (see picture) and showed efficient and stable CO formation at −0.2–−0.7 V versus the reversible hydrogen electrode (RHE) without a sacrificial reagent.

  4. Cover Pictures

    1. A Synergistic Capture Strategy for Enhanced Detection and Elimination of Bacteria

      Dr. Yong-Qiang Li, Bowen Zhu, Dr. Yuangang Li, Wan Ru Leow, Rubayn Goh, Dr. Bing Ma, Prof. Eileen Fong, Dr. Mark Tang and Prof. Xiaodong Chen

      Article first published online: 15 APR 2014 | DOI: 10.1002/anie.201401147

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      Efficient bacterial capture was achieved through a method based on the synergistic effect of surface nanotopography and surface chemistry on bacterial attachment. In their Communication (DOI: 10.1002/anie.201310135), X. Chen and co-workers show that packed silicon nanowires functionalized with bacteria-binding molecules show enhanced capture efficiency compared to surface-modified flat silicon and enable highly sensitive detection and efficient elimination of bacterial pathogens.

    2. Molecular Ionization from Carbon Nanotube Paper

      Rahul Narayanan, Depanjan Sarkar, Prof. R. Graham Cooks and Prof. Thalappil Pradeep

      Article first published online: 15 APR 2014 | DOI: 10.1002/anie.201401148

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      A piece of paper that is impregnated with multi-walled or single-walled carbon nanotubes generates ions from diverse analytes at voltages as low as 3 V, as T. Pradeep et al. show in their Communication (DOI: 10.1002/anie.201311053). This miniaturized ion source is held in front of a mass-spectrometer inlet to collect the mass spectrum. Common pesticides from the surface of an orange, active molecules from tablets, and a variety of analytes, such as amino acids, can be characterized.

    3. Cytoskeletal Actin Dynamics are Involved in Pitch-Dependent Neurite Outgrowth on Bead Monolayers

      Dr. Kyungtae Kang, Seo Young Yoon, Sung-Eun Choi, Mi-Hee Kim, Matthew Park, Prof. Dr. Yoonkey Nam, Prof. Dr. Jin Seok Lee and Prof. Dr. Insung S. Choi

      Article first published online: 15 APR 2014 | DOI: 10.1002/anie.201401146

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      Pitch-dependent neurite outgrowth was demonstrated in primary hippocampal neurons on monolayers of silica beads. In their Communication (DOI: 10.1002/anie.201400653), Y. Nam, J. S. Lee, I. S. Choi, and co-workers report that neurite outgrowth is accelerated on larger beads (white) compared to smaller beads (black) up to a bead diameter of approximately 1 μm. Biochemical analysis indicated that cytoskeletal actin dynamics are primarily responsible for the recognition of surface topography.

    4. Telluride Misfit Layer Compounds: [(PbTe)1.17]m(TiTe2)n

      Daniel B. Moore, Prof. Matt Beekman, Dr. Sabrina Disch and Dr. David C. Johnson

      Article first published online: 15 APR 2014 | DOI: 10.1002/anie.201401144

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      Much like skiers taking different lifts to different ski runs down a mountain, designed precursors can be used to direct the self-assembly of targeted intergrowth structures, as described by D. C. Johnson et al. in their Communication (DOI: 10.1002/anie.201401022). The image of Oregon's Mount Hood represents the potential energy landscape, and the colored lines illustrate how different starting points lead to the self-assembly of different metastable compounds.

    5. Engineering Multifunctional Capsules through the Assembly of Metal–Phenolic Networks

      Junling Guo, Dr. Yuan Ping, Dr. Hirotaka Ejima, Dr. Karen Alt, Mirko Meissner, Joseph J. Richardson, Dr. Yan Yan, Prof. Karlheinz Peter, Prof. Dominik von Elverfeldt, Assoc. Prof. Christoph E. Hagemeyer and Prof. Frank Caruso

      Article first published online: 15 APR 2014 | DOI: 10.1002/anie.201401143

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      Multifunctional capsules were assembled through interactions between metal ions and a single organic ligand. In their Communication (DOI: 10.1002/anie.201311136), F. Caruso et al. show that a common phenolic plant compound, tannic acid, can be used to coordinate a variety of metals, yielding a library of metal–phenolic network (MPN) capsules. The functional properties of the MPN capsule are determined by the coordinated metals, which can be tailored for various applications.

    6. Large Zero-Field Splittings of the Ground Spin State Arising from Antisymmetric Exchange Effects in Heterometallic Triangles

      Samantha A. Magee, Dr. Stephen Sproules, Dr. Anne-Laure Barra, Dr. Grigore A. Timco, Nicholas F. Chilton, Prof. David Collison, Prof. Richard E. P. Winpenny and Prof. Eric J. L. McInnes

      Article first published online: 15 APR 2014 | DOI: 10.1002/anie.201401141

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      The antisymmetric component of the electronic exchange interaction (also known as Dzyaloshinski–Moriya exchange) is often overlooked in modeling the magnetic data of molecular species, but in the Communication by E. J. L. McInnes and co-workers (DOI: 10.1002/anie.201400655), it is shown to be responsible for the large magnetic anisotropy in the S = 5/2 ground state of a trimetallic complex. The illustration plays on the concept of “antisymmetry” and triangles with an Escher triangle.

    7. Towards True Carbaporphyrinoids: Synthesis of 21-Carba-23-thiaporphyrin

      Dr. Anna Berlicka, Paweł Dutka, Dr. Ludmiła Szterenberg and Prof. Lechosław Latos-Grażyński

      Article first published online: 15 APR 2014 | DOI: 10.1002/anie.201401138

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      Replacement of a single pyrrole ring by a cyclopentadiene fragment appears to be a compelling strategy for the creation of true carbaporphyrins, which can be regarded as fundamental extensions of the classical porphyrinic motif. In their Communication (10.1002/anie.201310999), L. Latos-Grażyński and co-workers describe the rational approach that allowed incorporation of an unsubstituted cyclopentadiene instead of a pyrrole ring in a heteroporphyrin framework to form 21-carbathiaporphyrin, the first meso-substituted true carbaporphyrinoid.

  5. Communications

    1. Natural Products

      NMR Fingerprints of the Drug-like Natural-Product Space Identify Iotrochotazine A: A Chemical Probe to Study Parkinson’s Disease

      Dr. Tanja Grkovic, Dr. Rebecca H. Pouwer, Marie-Laure Vial, Luca Gambini, Alba Noël, Dr. John N. A. Hooper, Dr. Stephen A. Wood, Dr. George D. Mellick and Prof. Dr. Ronald J. Quinn

      Article first published online: 15 APR 2014 | DOI: 10.1002/anie.201402239

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      Seeing the invisible: A novel natural product, iotrochotazine A was isolated using an NMR-based strategy focused on the analysis of 1H NMR fingerprints of a prefractionated natural-product library. In a phenotypic assay panel based on hONS cells derived from idiopathic Parkinson’s disease (PD) patients, it affected the morphology and cellular distribution of lysosomes and early endosomes.

    2. Vibrational Imaging

      Live-Cell Quantitative Imaging of Proteome Degradation by Stimulated Raman Scattering

      Yihui Shen, Fang Xu, Lu Wei, Fanghao Hu and Prof. Wei Min

      Article first published online: 15 APR 2014 | DOI: 10.1002/anie.201310725

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      Breaking it down: Stimulated Raman scattering microscopy was coupled with metabolic labeling with 13C-phenylalanine to visualize global proteolysis activity in living cells with subcellular resolution. Through 12C/(12C+13C) ratio maps, the protein decay kinetics of mammalian cells under steady-state conditions and various perturbations, including oxidative stress, cell differentiation, and huntingtin protein aggregation, were quantified.

    3. Phosphine Catalysis

      Asymmetric Synthesis of Spiropyrazolones through Phosphine-Catalyzed [4+1] Annulation

      Dr. Xiaoyu Han, Dr. Weijun Yao, Dr. Tianli Wang, Yong Ren Tan, Ziyu Yan, Jacek Kwiatkowski and Prof. Dr. Yixin Lu

      Article first published online: 15 APR 2014 | DOI: 10.1002/anie.201311214

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      Optically enriched 4-spiro-5-pyrazolones were prepared through phosphine-catalyzed enantioselective [4+1] annulation. In this study, substituted pyrazolones were used as a C1 synthon in cycloaddition for the first time. Moreover, this is the first report in which α-substituted allenoates were utilized in an asymmetric [4+1] annulation.

    4. Biomimetics of Carbohydrate Nucleotides

      Fluorescent Mimetics of CMP-Neu5Ac Are Highly Potent, Cell-Permeable Polarization Probes of Eukaryotic and Bacterial Sialyltransferases and Inhibit Cellular Sialylation

      Dr. Johannes J. Preidl, Dr. Vinayaga S. Gnanapragassam, Dr. Michael Lisurek, Dr. Jörn Saupe, Prof. Dr. Rüdiger Horstkorte and Prof. Dr. Jörg Rademann

      Article first published online: 15 APR 2014 | DOI: 10.1002/anie.201400394

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      You can't run, you can't hide: Sialyltransferases cover cancer cells with neuraminic acids, enabling them to escape from tissues and to metastasize. Cell-permeable chemical probes targeting this class of enzymes might help to study, understand, and inhibit such processes.

    5. Helicenes

      Asymmetric Catalysis on the Nanoscale: The Organocatalytic Approach to Helicenes

      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.

    6. Magnetic Anisotropy

      Large Zero-Field Splittings of the Ground Spin State Arising from Antisymmetric Exchange Effects in Heterometallic Triangles

      Samantha A. Magee, Dr. Stephen Sproules, Dr. Anne-Laure Barra, Dr. Grigore A. Timco, Nicholas F. Chilton, Prof. David Collison, Prof. Richard E. P. Winpenny and Prof. Eric J. L. McInnes

      Article first published online: 15 APR 2014 | DOI: 10.1002/anie.201400655

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      Zeroing in: By using [RuIII2MnII(O)(tBuCO2)6(py)3] as an example, antisymmetric exchange effects have been shown to lead to very large spin ground-state zero-field splittings in polymetallic complexes. The zero-field splitting of the S=5/2 ground state of the heterometallic oxo-centered triangle has been measured as D=3 cm−1, an order of magnitude larger than found for the {Fe2Mn} analogue.

    7. Nanostructures

      Three-Dimensional Ordered Assembly of Thin-Shell Au/TiO2 Hollow Nanospheres for Enhanced Visible-Light-Driven Photocatalysis

      Cao-Thang Dinh, Hoang Yen, Prof. Freddy Kleitz and Prof. Trong-On Do

      Article first published online: 15 APR 2014 | DOI: 10.1002/anie.201400966

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      Order makes a difference: A three-dimensional ordered assembly of thin-shell Au/TiO2 hollow nanospheres exhibits not only a very high surface area but also photonic behavior and multiple light scattering. The designed materials show significantly enhanced visible-light absorption and a visible-light-driven photocatalytic activity several times higher than those of conventional Au/TiO2 nanopowders.

    8. Bioluminescence

      A Novel Type of Luciferin from the Siberian Luminous Earthworm Fridericia heliota: Structure Elucidation by Spectral Studies and Total Synthesis

      Valentin N. Petushkov, Maxim A. Dubinnyi, Aleksandra S. Tsarkova, Natalja S. Rodionova, Mikhail S. Baranov, Vadim S. Kublitski, Osamu Shimomura and Ilia V. Yampolsky

      Article first published online: 15 APR 2014 | DOI: 10.1002/anie.201400529

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      Feeling blue: UV, fluorescence, NMR, and HRMS spectroscopy studies were used to elucidate the structure of the luciferin from the recently discovered luminous earthworm Fridericia heliota. The luciferin, which is part of a novel ATP-dependent bioluminescent system, was found to be a peptide formed from oxalic acid, lysine, a modified tyrosine residue, and γ-aminobutyric acid.

    9. Cycloaddition

      The Divergent Synthesis of Nitrogen Heterocycles by Rhodium(II)-Catalyzed Cycloadditions of 1-Sulfonyl 1,2,3-Triazoles with 1,3-Dienes

      Dr. Hai Shang, Yuanhao Wang, Dr. Yu Tian, Juan Feng and Prof. Dr. Yefeng Tang

      Article first published online: 11 APR 2014 | DOI: 10.1002/anie.201400426

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      On the (di)verge: Rhodium(II)-catalyzed cycloadditions of 1-sulfonyl 1,2,3-triazoles with 1,3-dienes have been developed and enable the efficient and divergent synthesis of two types of synthetically valuable nitrogen heterocycles, 2,5-dihydroazepines and 2,3-dihydropyrroles, by formal [4+3] and [3+2] cycloadditions, respectively. Ts=4-toluenesulfonyl.

    10. Gold Medicine

      A Binuclear Gold(I) Complex with Mixed Bridging Diphosphine and Bis(N-Heterocyclic Carbene) Ligands Shows Favorable Thiol Reactivity and Inhibits Tumor Growth and Angiogenesis In Vivo

      Taotao Zou, Dr. Ching Tung Lum, Dr. Chun-Nam Lok, Dr. Wai-Pong To, Dr. Kam-Hung Low and Prof. Dr. Chi-Ming Che

      Article first published online: 11 APR 2014 | DOI: 10.1002/anie.201400142

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      It′s in the blood: A binuclear gold(I) complex 1-PF6 is stable towards blood thiols and is a tight-binding inhibitor of thioredoxin reductase (TrxR). In vivo antitumor studies show 81 % inhibition of tumor growth in mice with HeLa xenografts and 62 % inhibition of highly aggressive mouse B16-F10 melanoma.

    11. Natural Products

      Suffrutines A and B: A Pair of Z/E Isomeric Indolizidine Alkaloids from the Roots of Flueggea suffruticosa

      Zhen-Long Wu, Dr. Bing-Xin Zhao, Dr. Xiao-Jun Huang, Gen-Yun Tang, Dr. Lei Shi, Prof. Dr. Ren-Wang Jiang, Xin Liu, Dr. Ying Wang and Prof. Dr. Wen-Cai Ye

      Article first published online: 11 APR 2014 | DOI: 10.1002/anie.201400048

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      The discovery of a pair of novel indolizidine alkaloids, having a unique and highly conjugated C20 backbone, from the roots of Flueggea suffruticosa adds a new class to the indolizidine alkaloid family. Furthermore, they were shown to be Z/E isomers, interconvertible by light, and the trans,trans form exhibits potent activity for regulating the morphology of Neuro-2a cells.

    12. Multiple Bonds

      Terminal Imido Rhodium Complexes

      Ana M. Geer, Dr. Cristina Tejel, Dr. José A. López and Prof. Miguel A. Ciriano

      Article first published online: 11 APR 2014 | DOI: 10.1002/anie.201400023

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      A missing link: Terminal imido rhodium complexes with a Rh[DOUBLE BOND]N multiple bond have been prepared, thus providing compounds which have been elusive to synthesis. Preliminary studies indicate rhodium imides are somewhat ambiphilic and can therefore undergo protonation at the nitrogen atom, as well as hydrogenation at the Rh[DOUBLE BOND]N bond. These systems also engage in nitrene-group transfer and cycloaddition reactions.

    13. Supramolecular Isomers

      Distortional Supramolecular Isomers of Polyrotaxane Coordination Polymers: Photoreactivity and Sensing of Nitro Compounds

      In-Hyeok Park, Raghavender Medishetty, Ja-Yeon Kim, Prof. Dr. Shim Sung Lee and Prof. Dr. Jagadese J. Vittal

      Article first published online: 11 APR 2014 | DOI: 10.1002/anie.201310536

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      Polyrotaxane isomers! Of the four supramolecular isomers of coordination polymers synthesized, two have polyrotaxane structures that differ only in the relative positions of the wheel in the neighboring axle. They show different photoreactivity under UV light as well as sensing abilities of a number of organic nitro compounds.

    14. Artificial Signal Cascades

      Nanobiomolecular Multiprotein Clusters on Electrodes for the Formation of a Switchable Cascadic Reaction Scheme

      Dr. Sven C. Feifel, Andreas Kapp, Dr. Roland Ludwig and Prof. Dr. Fred Lisdat

      Article first published online: 11 APR 2014 | DOI: 10.1002/anie.201310437

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      Triprotein-containing architectures on electrodes for dual analyte detection: Interprotein electron transfer chains have been established for a multilayer system with three different proteins, namely cellobiose dehydrogenase (CDH), laccase (Lac), and cytochrome c (cyt c). The activity of the individual enzymes can be switched by the applied electrode potential.

    15. Two-Photon Protein Assembly

      Three-Dimensional Protein Networks Assembled by Two-Photon Activation

      Dr. Volker Gatterdam, Dr. Radhan Ramadass, Dr. Tatjana Stoess, Manuela A. H. Fichte, Prof. Dr. Josef Wachtveitl, Prof. Dr. Alexander Heckel and Prof. Dr. Robert Tampé

      Article first published online: 11 APR 2014 | DOI: 10.1002/anie.201309930

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      Chemical biology aims at controlling protein interactions and cell behavior by external stimuli. Tools are needed to manipulate and structure target molecules in a non-invasive manner, and this is best achieved by light. A two-photon-activatable glutathione can be used for the light-guided three-dimensional patterning of glutathione S-transferase at superior spatiotemporal resolution.

  6. Book Reviews

    1. Modern Methods in Stereoselective Aldol Reactions. Edited by Rainer Mahrwald.

      Claude Spino

      Article first published online: 11 APR 2014 | DOI: 10.1002/anie.201400982

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      Wiley-VCH, Weinheim, 2013. 485 pp., hardcover, € 149.00.—ISBN 978-3527332052

    2. Lithium Batteries. Advanced Technologies and Applications. Edited by Bruno Scrosati, K. M. Abraham, Walter van Schalkwijk and Jusef Hassoun.

      Miran Gaberšček

      Article first published online: 11 APR 2014 | DOI: 10.1002/anie.201400965

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      John Wiley & Sons, Hoboken, 2013. 392 pp., hardcover, € 119.00.—ISBN 978-1118183656

  7. Communications

    1. Heterocycle Synthesis

      Visible-Light-Induced Formal [3+2] Cycloaddition for Pyrrole Synthesis under Metal-Free Conditions

      Jun Xuan, Xu-Dong Xia, Ting-Ting Zeng, Zhu-Jia Feng, Prof. Dr. Jia-Rong Chen, Dr. Liang-Qiu Lu and Prof. Dr. Wen-Jing Xiao

      Article first published online: 11 APR 2014 | DOI: 10.1002/anie.201400602

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      Photo(chemistry) op: A photocatalytic formal [3+2] cycloaddition of 2H-azirines with alkynes has been established under the irradiation of visible light in the presence of an organic dye. This transformation provides efficient access to highly functionalized pyrroles in good yields and has been applied to the formal synthesis of an inhibitor for HMG-CoA reductase.

    2. Solid-Phase Synthesis

      Flow-Through Synthesis on Teflon-Patterned Paper To Produce Peptide Arrays for Cell-Based Assays

      Dr. Frédérique Deiss, Wadim L. Matochko, Natasha Govindasamy, Edith Y. Lin and Dr. Ratmir Derda

      Article first published online: 11 APR 2014 | DOI: 10.1002/anie.201402037

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      On the same page: The patterned deposition of Teflon on paper creates barriers resistant to organic solvents. The solvents confined by the pattern flow through the paper at a controlled flow-rate, which permits the flow-through synthesis of 96 peptides in parallel on one sheet of paper. The resulting peptide arrays can be used to perform cell-based assays and discover 3D materials that support cell adhesion and growth.

    3. Natural Product Synthesis

      Accelerating Spirocyclic Polyketide Synthesis using Flow Chemistry

      Dr. Sean Newton, Dr. Catherine F. Carter, Dr. Colin M. Pearson, Leandrode C Alves, Dr. Heiko Lange, Dr. Praew Thansandote and Prof. Steven V. Ley

      Article first published online: 11 APR 2014 | DOI: 10.1002/anie.201402056

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      Rise of the machines: The syntheses of two spirocyclic polyketides, spirangien A methyl ester and spirodienal A, are described. This machine-assisted approach extends the application of flow chemistry to complex natural product synthesis and includes several flow-through processes of transformations commonly encountered in total synthesis.

  8. News

  9. Highlights

    1. Drug Design

      Snapshot of Antidepressants at Work: The Structure of Neurotransmitter Transporter Proteins

      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. Cover Pictures

    1. Programmable Polymer-Based Supramolecular Temperature Sensor with a Memory Function

      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 (DOI: 10.1002/anie.201402108), 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.

    2. Metal- and Reagent-Free Highly Selective Anodic Cross-Coupling Reaction of Phenols

      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 (DOI: 10.1002/anie.201400627). 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 non-symmetric 2,2′-biphenols could be constructed from simple substrates without the generation of reagent waste.

  11. Communications

    1. Extractant Aggregation

      Elucidation of the Structure of Organic Solutions in Solvent Extraction by Combining Molecular Dynamics and X-ray Scattering

      Dr. Geoffroy Ferru, Donatien Gomes Rodrigues, Dr. Laurence Berthon, Dr. Olivier Diat, Dr. Pierre Bauduin and Dr. Philippe Guilbaud

      Article first published online: 11 APR 2014 | DOI: 10.1002/anie.201402677

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      A terrific team: The ill-defined self-aggregation of metal-ion extractants in oils was determined by using a combination of molecular-dynamics simulation and small-/wide-angle X-ray scattering (SWAXS) techniques (see picture). In this way, it was possible to quantitatively describe the molecular and supramolecular organization of the extractant in the organic phase at a wide range of concentrations.

    2. Hydrogen Evolution

      Highly Active Electrocatalysis of the Hydrogen Evolution Reaction by Cobalt Phosphide Nanoparticles

      Eric J. Popczun, Carlos G. Read, Christopher W. Roske, Prof. Nathan S. Lewis and Prof. Raymond E. Schaak

      Article first published online: 11 APR 2014 | DOI: 10.1002/anie.201402646

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      One step closer to Pt: Nanoparticles of cobalt phosphide (CoP) catalyze the hydrogen evolution reaction with high activity and stability under strongly acidic conditions. Its electrocatalytic performance places CoP amongst the best Earth-abundant alternatives to platinum.

    3. Cyclization

      Boron Perturbed Click Reactions Prompt Aromatic C[BOND]H Activations

      Dr. Daniel Winkelhaus and Prof. Dr. Douglas W. Stephan

      Article first published online: 11 APR 2014 | DOI: 10.1002/anie.201402567

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      Click on B: The reaction of bis(pentafluorophenyl)boron alkynes and azides leads to unusual N3BC heterocycles (see scheme) resulting from aromatic C[BOND]H activation of benzene and toluene. While subsequent treatment of the heterocycle with PMe3 gave the P[BOND]B adduct, reaction with PtBu3 effected deprotonation to generate the corresponding phosphonium salt.

    4. C[BOND]H Activation

      Iridium-Catalyzed Enantioselective C[BOND]H Alkylation of Ferrocenes with Alkenes Using Chiral Diene Ligands

      Prof. Dr. Takanori Shibata and Tsubasa Shizuno

      Article first published online: 11 APR 2014 | DOI: 10.1002/anie.201402518

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      Director’s cut: The first catalytic and enantioselective C[BOND]H alkylation of ferrocene derivatives with various alkenes was achieved. A cationic iridium complex, having a chiral diene ligand, and an isoquinolyl moiety as a directing group are essential for regioselective and enantioselective C[BOND]H bond activation. coe=cyclooctene, NaBARF=sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate.

    5. Carbon Nanotubes

      Mechanically Interlocked Single-Wall Carbon Nanotubes

      Alberto de Juan, Dr. Yann Pouillon, Dr. Luisa Ruiz-González, Dr. Almudena Torres-Pardo, Dr. Santiago Casado, Prof. Dr. Nazario Martín, Prof. Dr. Ángel Rubio and Dr. Emilio M. Pérez

      Article first published online: 11 APR 2014 | DOI: 10.1002/anie.201402258

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      Nanotubes in MINT condition! In a clipping reaction, macrocycles were formed by ring-closing metathesis around single-wall nanotubes (SWNTs) as “threads” to produce rotaxane-type species: mechanically interlocked derivatives of carbon nanotubes (MINTs; see picture). Extensive characterization, including high-resolution STEM and control experiments, proved the interlocked nature of the products.

  12. Author Profiles

    1. Yingfu Li

      Article first published online: 9 APR 2014 | DOI: 10.1002/anie.201403018

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      My favorite molecule is DNA, because it is simple yet mysterious. When I was eighteen I wanted to be a novelist.

  13. Communications

    1. Bioinorganic Chemistry

      A Bio-Inspired Switch Based on Cobalt(II) Disulfide/Cobalt(III) Thiolate Interconversion

      Dr. Marcello Gennari, Bertrand Gerey, Dr. Nikita Hall, Dr. Jacques Pécaut, Dr. Marie-Noëlle Collomb, Mathieu Rouzières, Dr. Rodolphe Clérac, Dr. Maylis Orio and Dr. Carole Duboc

      Article first published online: 9 APR 2014 | DOI: 10.1002/anie.201402125

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      A switchable CoII2 disulfide/CoIII thiolate system (see scheme; filled circles show the color change) is stable under aerobic conditions. It offers the chance to understand the disulfide/thiolate interconversion supported by transition-metal ions, which is proposed to be involved in various fundamental biological processes.

    2. Weak Interactions

      The Experimental Observation of the Intramolecular NO2/CO Interaction in Solution

      Dr. Michel Chiarucci, Dr. Alessia Ciogli, Dr. Michele Mancinelli, Silvia Ranieri and Prof. Dr. Andrea Mazzanti

      Article first published online: 9 APR 2014 | DOI: 10.1002/anie.201402366

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      Might without muscle: The weak electrostatic interaction between nitro and carbonyl moieties has been observed by means of variable-temperature NMR spectroscopy. Its energetic contribution was evaluated to be about 3 kcal mol−1 by DFT calculations, and confirmed by the measurement of internal energy barriers to the rotation of suitable nitroaryl rings (see picture).

    3. Mixed-Oxide Catalysts

      Stabilization of Catalytically Active Cu+ Surface Sites on Titanium–Copper Mixed-Oxide Films

      Dr. Ashleigh E. Baber, Dr. Xiaofang Yang, Dr. Hyun You Kim, Dr. Kumudu Mudiyanselage, Markus Soldemo, Dr. Jonas Weissenrieder, Dr. Sanjaya D. Senanayake, Dr. Abdullah Al-Mahboob, Dr. Jerzy T. Sadowski, Dr. Jaime Evans, Dr. José A. Rodriguez, Dr. Ping Liu, Dr. Friedrich M. Hoffmann, Dr. Jingguang G. Chen and Dr. Darío J. Stacchiola

      Article first published online: 9 APR 2014 | DOI: 10.1002/anie.201402435

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      Positively active: Copper oxide based structures were the first that could catalyze the oxidation of CO at room temperature. Their deactivation, however, is facile, because the required Cu+ state cannot be preserved under the reaction conditions. The addition of the right amount of titanium leads to mixed CuTiOx films that are thermally and chemically stable and more active CO oxidation catalysts than pure copper oxide materials.

    4. Boron Radicals

      Evidence for Extensive Single-Electron-Transfer Chemistry in Boryl Anions: Isolation and Reactivity of a Neutral Borole Radical

      Dr. Rüdiger Bertermann, Prof. Dr. Holger Braunschweig, Dr. Rian D. Dewhurst, Dipl.-Chem. Christian Hörl, Dipl.-Chem. Thomas Kramer and Dr. Ivo Krummenacher

      Article first published online: 9 APR 2014 | DOI: 10.1002/anie.201402556

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      ReSETting perspectives: A borolyl anion displays single-electron-transfer (SET) processes in its reaction with triorganotetrel halides. This was confirmed by the isolation of the first neutral borolyl radical. This radical reactivity was exploited in the synthesis of compounds with rare B[BOND]Sn and B[BOND]Pb bonds, the latter of which is the first structurally characterized species with a “noncluster” B[BOND]Pb bond.

    5. Homogeneous Catalysis

      Synthesis of Cyclic Amine Boranes through Triazole-Gold(I)-Catalyzed Alkyne Hydroboration

      Qiaoyi Wang, Stephen E. Motika, Dr. Novruz G. Akhmedov, Prof. Jeffrey L. Petersen and Prof. Xiaodong Shi

      Article first published online: 9 APR 2014 | DOI: 10.1002/anie.201402614

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      Stable and active: The first catalytic alkyne hydroboration of propargyl amine boranecarbonitrile is accomplished. While the typical [L-Au]+ species decomposed within minutes upon addition of amine boranecarbonitriles, the triazole-modified gold catalysts (TA-Au) remained active and allowed formation of 1,2-BN-cyclopentenes in excellent yields.

  14. Cover Pictures

    1. Room-Temperature Carbide-Derived Carbon Synthesis by Electrochemical Etching of MAX Phases

      Maria R. Lukatskaya, Joseph Halim, Boris Dyatkin, Michael Naguib, Yulia S. Buranova, Prof. Michel W. Barsoum and Prof. Yury Gogotsi

      Article first published online: 9 APR 2014 | DOI: 10.1002/anie.201403559

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      The electrochemically induced extraction of metal atoms from the ternary layered carbides Ti3AlC2, Ti2AlC, and Ti3SiC2 (MAX phases) at room temperature results in predominantly amorphous carbon with a narrow distribution of micropores, as described by Y. Gogotsi et al. in their Communication (DOI: 10.1002/anie.201402513). This approach forgoes energy-intensive thermal processing and presents a novel method for the synthesis of carbon materials that may be used as supercapacitors, battery electrodes, or for CO2 capture.

    2. High Degree of Polymerization in a Fullerene-Containing Supramolecular Polymer

      Dr. Helena Isla, Dr. Emilio M. Pérez and Prof. Dr. Nazario Martín

      Article first published online: 9 APR 2014 | DOI: 10.1002/anie.201403680

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      Including a preorganized macrocyclic host in a self-recognizing monomer and using fullerenes as guests leads to supramolecular polymers with a very high degree of polymerization. H. Isla, E. M. Pérez, and N. Martín show in their Communication (10.1002/anie.201402828) that molecular weights above 150 kDa were determined in solution, while up to 90 kDa could be detected experimentally through MALDI-TOF mass spectrometry. Very long and straight fibers of lengths in the micrometer range were found under AFM.

  15. News

  16. Communications

    1. Zeolite Structures

      A Germanosilicate Structure with 11×11×12-Ring Channels Solved by Electron Crystallography

      Wei Hua, Hong Chen, Dr. Zheng-Bao Yu, Prof. Xiaodong Zou, Prof. Jianhua Lin and Prof. Junliang Sun

      Article first published online: 9 APR 2014 | DOI: 10.1002/anie.201309766

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      A stable germanosilicate with 3D 11×11×12 ring channels, PKU-16 (see picture), was synthesized with a simple organic structure-directing agent. Nanosized PKU-16 was structurally characterized by the new rotation electron diffraction methods. The structure of PKU-16 is related with zeolite β polymorph C by rotating half of the 4-rings in the double mtw units.

    2. Synthetic Methods

      Light-Induced Ruthenium-Catalyzed Nitrene Transfer Reactions: A Photochemical Approach towards N-Acyl Sulfimides and Sulfoximines

      Dr. Vincent Bizet, Laura Buglioni and Prof. Dr. Carsten Bolm

      Article first published online: 9 APR 2014 | DOI: 10.1002/anie.201310790

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      Double duty: A one-pot sulfur imidation/oxidation sequence using a single ruthenium complex for both steps was developed (see scheme). Photochemical decarboxylations of 1,4,2-dioxazol-5-ones provide N-acyl nitrenes, which imidate sulfides at ambient temperature. The subsequent oxidation then occurs under mild phase-transfer catalysis conditions. In this manner, N-acyl sulfimides and sulfoximines can be obtained in high yields starting from sulfides.

    3. Intramolecular Aminocyanation of Alkenes by N[BOND]CN Bond Cleavage

      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.

    4. Bioinorganic Chemistry

      Regulated Incorporation of Two Different Metal Ions into Programmed Sites in a Duplex by DNA Polymerase Catalyzed Primer Extension

      Tatsuya Funai, Junko Nakamura, Yuki Miyazaki, Risa Kiriu, Dr. Osamu Nakagawa, Dr. Shun-ichi Wada, Prof. Akira Ono and Prof. Hidehito Urata

      Article first published online: 9 APR 2014 | DOI: 10.1002/anie.201311235

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      (Quick) silver DNA: HgII and AgI ions were found to specifically trigger DNA polymerase catalyzed primer extension in the absence of a Watson–Crick matched nucleotide through the formation of T–HgII–T and newly discovered C–AgI–T base pairs. The strict base recognition by the metal ions enabled regulated incorporation of the two different metal ions into programmed sites in duplex DNA.

    5. Metal–Organic Framework Films

      Lithographic Deposition of Patterned Metal–Organic Framework Coatings Using a Photobase Generator

      Dr. Benjamin K. Keitz, Chung Jui Yu, Prof. Jeffrey R. Long and Dr. Rob Ameloot

      Article first published online: 9 APR 2014 | DOI: 10.1002/anie.201400580

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      A photobase generator and UV irradiation were used to generate the metal–organic frameworks HKUST-1 and {Cu2(trans-1,4-cyclohexanedicarboxylate)2} at room temperature. This method was subsequently applied to the preparation of patterned metal–organic framework coatings.

    6. Host–Guest Chemistry

      Noncovalent Chirality Sensing Ensembles for the Detection and Reaction Monitoring of Amino Acids, Peptides, Proteins, and Aromatic Drugs

      Dr. Frank Biedermann and Prof. Dr. Werner M. Nau

      Article first published online: 9 APR 2014 | DOI: 10.1002/anie.201400718

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      Strong and diagnostic induced circular dichroism signals in the near-UV or visible region are obtained when chiral, optically transparent analytes bind to an achiral chemosensing ensemble composed of a macrocyclic host and dye. This affords a novel, supramolecular detection method for chiral aromatic analytes in water.

    7. Targeted Synthesis

      Telluride Misfit Layer Compounds: [(PbTe)1.17]m(TiTe2)n

      Daniel B. Moore, Prof. Matt Beekman, Dr. Sabrina Disch and Dr. David C. Johnson

      Article first published online: 9 APR 2014 | DOI: 10.1002/anie.201401022

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      Challenging the limits of solid-state synthesis: A synthetic method that entails the design of precursors to form targeted products that are not accessible by traditional solid-state synthesis is put to the test. This method is used to produce the first reported family of telluride misfit layer compounds.

  17. Highlights

    1. Phosphorus Compounds

      New Phosphorus Analogues of Nitrogen Classics—No Carbon Copies

      Prof. Dr. Dietrich Gudat

      Article first published online: 9 APR 2014 | DOI: 10.1002/anie.201400762

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      Getting heavy: The recently prepared phosphorus analogues of two old acquaintances, urea and dinitrogen tetroxide, bear some structural resemblance to their archetypes but are no carbon copies. Their syntheses and chemical properties reveal rather certain peculiarities, which back the doctrine that the electronic properties of the heavier elements in a group differ from those of the lightest congener.

  18. Communications

    1. Heterocycles

      Gold-Catalyzed Synthesis of Functionalized Pyridines by Using 2H-Azirines as Synthetic Equivalents of Alkenyl Nitrenes

      Dr. Agnes Prechter, Guilhem Henrion, Pierre Faudot dit Bel and Fabien Gagosz

      Article first published online: 8 APR 2014 | DOI: 10.1002/anie.201402470

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      Ringing the changes: A series of easily accessible 2-propargyl 2H-azirine derivatives were efficiently converted into the corresponding functionalized pyridines in the presence of a gold catalyst. This transformation, which exhibits a high functional-group tolerance and a wide substrate scope, corresponds to the formal intramolecular transfer of an alkenyl nitrene to an alkyne.

    2. Vaccine Engineering

      Construction of a Live-Attenuated HIV-1 Vaccine through Genetic Code Expansion

      Nanxi Wang, Dr. Yue Li, Dr. Wei Niu, Dr. Ming Sun, Dr. Ronald Cerny, Prof. Qingsheng Li and Prof. Jiantao Guo

      Article first published online: 8 APR 2014 | DOI: 10.1002/anie.201402092

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      Combat against AIDS: A novel unnatural amino acid (UAA*)-mediated amber codon (UAG) suppression strategy was used to precisely control HIV-1 viability in vitro (see picture). The resulting live-attenuated virus can be potentially used as HIV-1 vaccine.

    3. Asymmetric Catalysis

      Chiral Anion Phase Transfer of Aryldiazonium Cations: An Enantioselective Synthesis of C3-Diazenated Pyrroloindolines

      Dr. Hosea M. Nelson, Solomon H. Reisberg, Hunter P. Shunatona, Jigar S. Patel and Prof. Dr. F. Dean Toste

      Article first published online: 8 APR 2014 | DOI: 10.1002/anie.201310905

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      Live and let diazene: Chiral anion phase transfer of aryldiazonium cations has been utilized to prepare C3-diazenated pyrroloindolines. The air- and water-tolerant reaction allows electronic and steric diversity in the aryldiazonium electrophile and the tryptamine core, with the products being obtained in up to 99 % yield and 96 % ee (MTBE=methyl tert-butyl ether).

    4. Synthetic Methods

      Hydrocarbation of C[TRIPLE BOND]C Bonds: Quantification of the Nucleophilic Reactivity of Ynamides

      M. Sc. Hans A. Laub, Prof. Dr. Gwilherm Evano and Prof. Dr. Herbert Mayr

      Article first published online: 8 APR 2014 | DOI: 10.1002/anie.201402055

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      Carbenium ions are isoelectronic with boranes, but hydrocarbations analogous to hydroborations usually do not occur. The hydrocarbation of ynamides with benzhydrylium ions and the difference to hydroborations are discussed. Furthermore, kinetic studies allowed the inclusion of ynamides in the comprehensive benzhydrylium-based nucleophilicity scale.

    5. Rhodium-Catalyzed Tandem Cyclization/Si[BOND]C Activation Reaction for the Synthesis of Siloles

      Dr. Qing-Wei Zhang, Kun An and Prof. Dr. Wei He

      Article first published online: 8 APR 2014 | DOI: 10.1002/anie.201400828

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      Bare your siloles: The title reaction involving Si[BOND]C(sp3) bond activation was developed for the synthesis of photoluminescent siloles. An external proton source promotes the rhodium catalyst turnover. In addition, the selective activation of Si[BOND]C(sp2) bonds was discovered through the use of a π-acid additive. This method enabled the first synthesis of benzofuran siloles and provided rapid access to conjugated siloles by facile derivatization.

    6. Fluorescent Dyes

      Geminate Recombination as a Photoprotection Mechanism for Fluorescent Dyes

      Phil Holzmeister, Andreas Gietl and Prof. Dr. Philip Tinnefeld

      Article first published online: 8 APR 2014 | DOI: 10.1002/anie.201310300

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      Single-molecule spectroscopy reveals a new mechanism for diffusion-limited photoprotection. Geminate recombination after reduction of organic dyes by thiols enhances photostabilization by avoiding the buildup of photobleaching intermediates such as photo-oxidized states. Stable and long-lasting fluorescence can be achieved in combination with ROXS buffers.

    7. Mechanobiochemistry

      Mechanically Modulating the Photophysical Properties of Fluorescent Protein Biocomposites for Ratio- and Intensiometric Sensors

      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.

  19. Highlights

    1. Cytochrome P450

      19582014: After 56 Years of Research, Cytochrome P450 Reactivity Is Finally Explained

      Ashley B. McQuarters, Matthew W. Wolf, Andrew P. Hunt and Dr. Nicolai Lehnert

      Article first published online: 7 APR 2014 | DOI: 10.1002/anie.201402404

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      Nature's wisdom in enzyme design: Compounds I and II in the catalytic cycle of the Cytochrome P450 enzymes have been trapped and characterized recently. This work has provided further insight into the electronic structure and reactivity of these crucial intermediates, and key questions regarding the mechanism of these enzymes have finally been answered.

  20. Communications

    1. Supramolecular Polymers

      Supramolecular Polymerization Promoted and Controlled through Self-sorting

      Zehuan Huang, Liulin Yang, Yiliu Liu, Prof. Zhiqiang Wang, Dr. Oren A. Scherman and Prof. Xi Zhang

      Article first published online: 7 APR 2014 | DOI: 10.1002/anie.201402817

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      Got it under control: A method in which supramolecular polymerization is controlled through self-sorting is reported. The p-phenylene (green circles) and naphthalene (blue ovals) moieties of the bifunctional monomer are selectively recognized by cucurbit[7]uril (green barrels) and cucurbit[8]uril (blue barrels), respectively. The processes of polymerization and degradation can be controlled by tuning the cucurbit[7]uril content.

    2. Nanocomposites

      In Situ Synthesis of Robust Conductive Cellulose/Polypyrrole Composite Aerogels and Their Potential Application in Nerve Regeneration

      Zhuqun Shi, Huichang Gao, Jiao Feng, Beibei Ding, Prof. Xiaodong Cao, Prof. Shigenori Kuga, Prof. Yingjun Wang, Prof. Lina Zhang and Prof. Jie Cai

      Article first published online: 7 APR 2014 | DOI: 10.1002/anie.201402751

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      Composite gels prepared from nanoporous cellulose gel and in situ formed polypyrrole nanoparticles have low density, large surface area, high mechanical strength, sufficient electrical conductivity, no cytotoxicity, and neural differentiation ability. This robust conductive gel/aerogel will be useful for the development of materials for nerve regeneration, carbon capture, catalyst supports, and many other applications.

    3. Enzyme Catalysis

      Entropy is Key to the Formation of Pentacyclic Terpenoids by Enzyme-Catalyzed Polycyclization

      Dr. Per-Olof Syrén, Stephan C. Hammer, Dr. Birgit Claasen and Prof. Dr. Bernhard Hauer

      Article first published online: 7 APR 2014 | DOI: 10.1002/anie.201402087

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      Disorderly conduct: Through theoretical and experimental work with a thermophilic triterpene cyclase, it was demonstrated that entropy is key to the polycyclizations that it catalyzes. The release of water molecules (red) through specific channels allows for the prefolding of the polyisoprene substrate (purple) and thus the generation of multicyclic scaffolds by terpene cyclase enzymes.

    4. Polymeric Thermometers

      Programmable Polymer-Based Supramolecular Temperature Sensor with a Memory Function

      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 reported that 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.

    5. Natural Product Synthesis

      A Rapid Synthesis of 4-Oxazolidinones: Total Synthesis of Synoxazolidinones A and B

      Nataliia V. Shymanska, Il Hwan An and Prof. Joshua G. Pierce

      Article first published online: 7 APR 2014 | DOI: 10.1002/anie.201402310

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      Synthetic synoxazolidinones: A five-step total synthesis of the marine natural product synoxazolidinone A was achieved through a diastereoselective imine acylation/cyclization cascade. Synoxazolidinone B and a series of analogues were also prepared to explore the potential of these 4-oxazolidinones as antimicrobial agents. The results revealed simplified dichloro derivatives that are equally potent against several bacterial strains.

    6. Graphene Quantum Dots

      White-Light-Emitting Edge-Functionalized Graphene Quantum Dots

      Prof. Dr. Ryo Sekiya, Yuichiro Uemura, Prof. Dr. Hideki Murakami and Prof. Dr. Takeharu Haino

      Article first published online: 7 APR 2014 | DOI: 10.1002/anie.201311248

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      In the dotlight: Graphene quantum dots (GQDs) functionalized with bulky Fréchet’s dendritic wedges at the GQD periphery were synthesized. The single-layered, size-regulated structures of the dendronized GQDs were revealed by atomic force microscopy. The edge-functionalization of the GQDs led to white-light emission, which is an uncommon feature.

    7. Nanostructures

      Two-Dimensional CuSe Nanosheets with Microscale Lateral Size: Synthesis and Template-Assisted Phase Transformation

      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.

    8. Catalytic Oxidation

      Trinuclear Pd3O2 Intermediate in Aerobic Oxidation Catalysis

      Andrew J. Ingram, Dr. Diego Solis-Ibarra, Prof. Richard N. Zare and Prof. Robert M. Waymouth

      Article first published online: 7 APR 2014 | DOI: 10.1002/anie.201400134

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      Catalytic ménage à trois: A catalytically active trinuclear Pd3O2 complex was identified during Pd-mediated aerobic oxidation of alcohols. Synthesis, structural characterization, and catalytic studies of the trinuclear compound show that it is a product of oxygen activation by reduced palladium species and is a competent intermediate in the catalytic aerobic oxidation of alcohols. These results illuminate a new pathway for O2 reduction by Pd complexes.

    9. Environmental Chemistry

      A Superhydrophobic Sponge with Excellent Absorbency and Flame Retardancy

      Changping Ruan, Kelong Ai, Xingbo Li and Prof. Lehui Lu

      Article first published online: 7 APR 2014 | DOI: 10.1002/anie.201400775

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      Coming clean: A robust and flame-retardant sponge has been prepared from the commercially available melamine sponge through a simple and mild two-step strategy. The superhydrophobicity, high porosity, robust stability, and intrinsic flame-retardant nature of the sponge enables the absorption and recycling of crude oil (see picture) as well as organic solvents. The fabrication of this sponge is easy to scale up.

    10. Synthetic Methods

      Heterocycle Synthesis Based on Allylic Alcohol Transposition Using Traceless Trapping Groups

      Youwei Xie and Prof. Paul E. Floreancig

      Article first published online: 7 APR 2014 | DOI: 10.1002/anie.201402010

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      Without a trace: Allylic alcohols transpose in the presence of Re2O7 and are trapped by aldehydes or ketones to form hemiacetals. Additional ionization yields oxocarbenium ions, which can be quenched through bimolecular reactions with nucleophiles to provide heterocycles with no trace of the initial trapping group. This method allows stereocontrol in the absence of chiral reagents and without recourse to protecting or leaving groups.

    11. Asymmetric Catalysis

      Asymmetric Hydrogenation of Maleic Acid Diesters and Anhydrides

      Dr. Maurizio Bernasconi, Marc-André Müller and Prof. Dr. Andreas Pfaltz

      Article first published online: 7 APR 2014 | DOI: 10.1002/anie.201402034

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      An attractive enantioselective route to 2-alkyl- and 2-aryl-substituted succinic acid derivatives is opened up by the asymmetric hydrogenation of maleic and fumaric acid derivatives, using the new catalyst [Ir(cod)L]BArF, derived from a 2,6-difluorophenyl-substituted pyridine-phosphinite ligand. The products are valuable chiral building blocks having a structural motif found in many bioactive compounds. cod=1,5-cyclooctadiene.

    12. Diborenes

      Boron Radical Cations from the Facile Oxidation of Electron-Rich Diborenes

      Dr. Philipp Bissinger, Prof. Dr. Holger Braunschweig, Dr. Alexander Damme, Dr. Thomas Kupfer, Dr. Ivo Krummenacher and Dr. Alfredo Vargas

      Article first published online: 7 APR 2014 | DOI: 10.1002/anie.201311110

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      The NHC- and phosphine-stabilized diborenes IMe⋅(Dur)B[DOUBLE BOND]B(Dur)⋅IMe and PEt3⋅(Mes)B[DOUBLE BOND]B(Mes)⋅PEt3 possess an unusually high boron-centered electron density, making them very strong neutral reductants. Thus, removal of one electron from the B[BOND]B π systems occurs readily by chemical oxidation with (C7H7)BArf4 to afford the corresponding radical cations. The nature of the Lewis base exerts strong influence on the electronic structure of the neutral and cationic diborene systems.

    13. Anion Transport

      A Flexible Solution to Anion Transport: Powerful Anionophores Based on a Cyclohexane Scaffold

      James A. Cooper, Steven T. G. Street and Prof. Anthony P. Davis

      Article first published online: 7 APR 2014 | DOI: 10.1002/anie.201311071

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      Speedy shuttling: New anionophores were developed which are simpler and far more accessible than conceptually related earlier systems. They are also less preorganized and anion affinities are lower (as expected), but transport activities set new records. This surprising performance suggests a role for controlled flexibility in the design of transmembrane anion carriers.

    14. Mixed-Matrix Membranes

      Simultaneous Spray Self-Assembly of Highly Loaded ZIF-8–PDMS Nanohybrid Membranes Exhibiting Exceptionally High Biobutanol-Permselective Pervaporation

      Hongwei Fan, Dr. Qi Shi, Hao Yan, Prof. Shulan Ji, Prof. Jinxiang Dong and Prof. Guojun Zhang

      Article first published online: 7 APR 2014 | DOI: 10.1002/anie.201309534

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      Thin and functional: A ZIF-8/polymer suspension and a cross-linker/catalyst solution were simultaneously sprayed onto a polysulfone substrate (see picture). The nanoparticles of the zeolitic imidazolate framework ZIF-8 were dispersed uniformly and separated from one another by the polymer chains. The resulting ZIF-8/polymer nanohybrid membranes exhibited excellent biobutanol-permselective pervaporation.

    15. Structure Elucidation

      Magnesiacyclopentadienes as Alkaline-Earth Metallacyclopentadienes: Facile Synthesis, Structural Characterization, and Synthetic Application

      Junnian Wei, Liang Liu, Ming Zhan, Ling Xu, Prof. Dr. Wen-Xiong Zhang and Prof. Dr. Zhenfeng Xi

      Article first published online: 7 APR 2014 | DOI: 10.1002/anie.201310116

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      Mg in the middle: The first series of spiro-dilithio magnesiacyclopentadienes, magnesiacyclopentadienes, and dimagnesiabutadienes has been synthesized and structurally characterized. Unique structural characteristics and bonding were revealed, and the reaction chemistry and synthetic applications were studied. An efficient method for synthesizing amino cyclopentadienes was established by using thioformamides.

    16. Metal–Organic Frameworks

      Pressure-Induced Bond Rearrangement and Reversible Phase Transformation in a Metal–Organic Framework

      Dr. Elinor C. Spencer, Dr. Mangalampalli S. R. N. Kiran, Dr. Wei Li, Prof. Upadrasta Ramamurty, Prof. Nancy L. Ross and Prof. Anthony K. Cheetham

      Article first published online: 7 APR 2014 | DOI: 10.1002/anie.201310276

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      A reversible pressure-induced phase transformation associated with a substantial bond rearrangement is discovered in the metal–organic framework [tmenH2][Er(HCOO)4]2 (tmenH22+=N,N,N′,N′-tetramethylethylenediammonium). The transition is first-order and is accompanied by a unit cell volume change of about 10 %. X-ray diffraction studies reveal the complex bond rearrangement process.

  21. Reviews

    1. Spectroscopic Methods

      Surface-Enhanced Raman Spectroscopy: Concepts and Chemical Applications

      Prof. Dr. Sebastian Schlücker

      Article first published online: 7 APR 2014 | DOI: 10.1002/anie.201205748

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      Expanding vibrational spectroscopy: Since its first observation in 1973, surface-enhanced Raman scattering (SERS) has developed into a mature vibrational spectroscopic technique. The number of applications in chemistry as well as the material and life sciences is increasing rapidly. This Review summarizes the key concepts behind SERS and provides an overview of current applications in chemistry.

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