Angewandte Chemie International Edition

Cover image for Vol. 52 Issue 51

December 16, 2013

Volume 52, Issue 51

Pages 13479–13821

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Flashback
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Review
    13. Communications
    1. You have free access to this content
      Cover Picture: “Metal-Free” Catalytic Oxygen Reduction Reaction on Heteroatom-Doped Graphene is Caused by Trace Metal Impurities (Angew. Chem. Int. Ed. 51/2013) (page 13479)

      Lu Wang, Dr. Adriano Ambrosi and Prof. Martin Pumera

      Version of Record online: 25 NOV 2013 | DOI: 10.1002/anie.201309814

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      The oxygen reduction reaction (ORR) is of high industrial importance. A significant research effort has been directed to the so-called “metal-free” ORR. In their Communication on page 13818 ff., M. Pumera et al. show that the claimed “metal-free” electrocatalysis of the ORR on heteroatom-doped graphene is caused by metallic impurities. The picture shows the reduction of O2 to water by a graphene sheet stained with manganese, with the Indonesian coral reef in the background.

    2. You have free access to this content
      Inside Cover: Synthesis of Highly pH-Responsive Glucose Poly(orthoester) (Angew. Chem. Int. Ed. 51/2013) (page 13480)

      Lingyao Li, Yi Xu, Ian Milligan, Liye Fu, Emily A. Franckowiak and Prof. Wenjun Du

      Version of Record online: 4 DEC 2013 | DOI: 10.1002/anie.201310217

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      Degradable sugar polymers with orthoester linkages connecting the sugar units were chemically synthesized by W. Du and co-workers, as described in their Communication on page 13699 ff. Under optimal polymerization conditions, polymers with with molecular weights up to 6.9 kDa were synthesized. These polymers are highly pH-responsive because of the acid-labile linkages in the backbone.

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      Inside Back Cover: Effect of Pressure on the Stability of G-Quadruplex DNA: Thermodynamics under Crowding Conditions (Angew. Chem. Int. Ed. 51/2013) (page 13823)

      Dr. Shuntaro Takahashi and Prof. Naoki Sugimoto

      Version of Record online: 13 NOV 2013 | DOI: 10.1002/anie.201309404

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      The effect of pressure on the stability of biomolecules such as DNA is quite unique compared with that of temperature. In their Communication on page 13774 ff., S. Takahashi and N. Sugimoto demonstrate that high pressure causes unfolding of G-quadruplex DNA. However, the effect was repressed under conditions that mimic those in cells, thereby shedding light on the mechanism of gene expression and novel DNA nanotechnology using pressure.

    4. You have free access to this content
      Back Cover: Stabilization of Copper Catalysts for Liquid-Phase Reactions by Atomic Layer Deposition (Angew. Chem. Int. Ed. 51/2013) (page 13824)

      Brandon J. O'Neill, David H. K. Jackson, Dr. Anthony J. Crisci, Carrie A. Farberow, Fengyuan Shi, Dr. Ana C. Alba-Rubio, Dr. Junling Lu, Dr. Paul J. Dietrich, Dr. Xiangkui Gu, Dr. Christopher L. Marshall, Prof. Peter C. Stair, Dr. Jeffrey W. Elam, Dr. Jeffrey T. Miller, Prof. Fabio H. Ribeiro, Prof. Paul M. Voyles, Prof. Jeffrey Greeley, Prof. Manos Mavrikakis, Prof. Susannah L. Scott, Prof. Thomas F. Kuech and Prof. James A. Dumesic

      Version of Record online: 28 NOV 2013 | DOI: 10.1002/anie.201309934

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      Deactivation of heterogeneous catalysts is an important issue in liquid-phase catalytic processes and for the utilization of base metal catalysts, such as copper. In their Communication on page 13808 ff., J. A. Dumesic et al. show that atomic layer deposition can be used to build a protective coating around metallic nanoparticles, thereby preventing irreversible catalyst deactivation during liquid-phase catalytic processing.

  2. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Flashback
    5. Corrigendum
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    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Review
    13. Communications
  3. Flashback

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    11. Highlights
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    13. Communications
    1. 50 Years Ago ... (page 13500)

      Version of Record online: 17 DEC 2013 | DOI: 10.1002/anie.201390053

  4. Corrigendum

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    1. You have free access to this content
      Corrigendum: Tuning a P450 Enzyme for Methane Oxidation (page 13503)

      Dr. Felipe E. Zilly, Dr. Juan P. Acevedo, Dr. Wojciech Augustyniak, Alfred Deege, Ulrich W. Häusig and Prof. Manfred T. Reetz

      Version of Record online: 17 DEC 2013 | DOI: 10.1002/anie.201309655

      This article corrects:

      Tuning a P450 Enzyme for Methane Oxidation1

      Vol. 50, Issue 12, 2720–2724, Version of Record online: 17 FEB 2011

  5. News

    1. Top of page
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    3. Graphical Abstract
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    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Review
    13. Communications
  6. Author Profile

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Flashback
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Review
    13. Communications
    1. Bruce C. Gates (page 13510)

      Version of Record online: 14 OCT 2013 | DOI: 10.1002/anie.201307436

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      “My favorite saying is when the going gets tough, the tough get going (meant ironically). I admire Nelson Mandela …” This and more about Bruce C. Gates can be found on page 13510.

  7. News

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    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Review
    13. Communications
  8. Obituary

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    9. Obituary
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    12. Review
    13. Communications
    1. John D. Corbett (1926–2013) (pages 13513–13514)

      Gerd Meyer, Anja-Verena Mudring and Kenneth R. Poeppelmeier

      Version of Record online: 25 NOV 2013 | DOI: 10.1002/anie.201309705

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  9. Book Review

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    13. Communications
    1. Heterocyclic Chemistry in Drug Discovery. Edited by Jie Jack Li. (page 13515)

      Oliver Thiel

      Version of Record online: 20 NOV 2013 | DOI: 10.1002/anie.201308187

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      John Wiley and Sons, Hoboken, 2013. 720 pp., hardcover, $ 150.00.—ISBN 978-1118148907

  10. Highlights

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    13. Communications
    1. Enzymology

      And the Winner is…Azadithiolate: An Amine Proton Relay in the [FeFe] Hydrogenases (pages 13518–13520)

      Dr. David Schilter and Prof. Dr. Thomas B. Rauchfuss

      Version of Record online: 4 NOV 2013 | DOI: 10.1002/anie.201307132

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      A victory in the pocket: An international team of chemists and biophysicists have resolved the long-standing question of the structure of the active site of the [FeFe] hydrogenases by assembling the active enzyme with a version of the active site synthesized in vitro (see scheme; HydF is a scaffold protein, HydA1 is a natural hydrogenase). The protein incorporating the diiron complex 2 showed similar activity to that of the natural enzyme.

    2. Molecular Imaging

      Single-Molecule Chemical Reactions Tracked at the Atomic-Bond Level (pages 13521–13523)

      Dr. Jiong Lu and Prof. Dr. Kian Ping Loh

      Version of Record online: 23 OCT 2013 | DOI: 10.1002/anie.201305041

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      On the right track: Recent advances in noncontact atomic force microscopy (nc-AFM) have enabled the bond-resolved imaging of reaction pathways. In particular, unprecedented insights into complex enediyne cyclization cascades on silver surfaces were gained by single-molecule imaging.

  11. Review

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    13. Communications
    1. Genomic Imprinting

      Genomic Imprinting—The Struggle of the Genders at the Molecular Level (pages 13524–13536)

      Renata Z. Jurkowska and Prof. Dr. Albert Jeltsch

      Version of Record online: 7 NOV 2013 | DOI: 10.1002/anie.201307005

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      Battle of the sexes: Genomic imprinting, the parent of origin-dependent monoallelic expression of genes, mediates a parental conflict in mammals. It is based on the presence of a DNA methylation mark on one allele and affects about 100 genes, which are often involved in growth and development. This Review describes the molecular processes leading to the generation and preservation of imprints during development and summarizes the relevance of parental imprinting for human health.

  12. Communications

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    13. Communications
    1. Stimuli-Responsive Microgels

      A Microgel Construction Kit for Bioorthogonal Encapsulation and pH-Controlled Release of Living Cells (pages 13538–13543)

      Dirk Steinhilber, Torsten Rossow, Dr. Stefanie Wedepohl, Florian Paulus, Dr. Sebastian Seiffert and Prof. Dr. Rainer Haag

      Version of Record online: 29 NOV 2013 | DOI: 10.1002/anie.201308005

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      Cells on demand: pH-Cleavable cell-laden microgels with excellent long-term viabilities were fabricated by combining bioorthogonal click chemistry and microfluidics. Functionalized PEG and dendritic polyglycerol (dPG) derivatives served as bioinert microgel precursors for cell encapsulation and pH-controlled release. This 3D microgel construction kit provides an optimal and responsive environment for biological systems.

    2. Cluster Compounds

      Unusual 14-Electron Fragments [Pd(η3-Bi3−xPbx)](x+1)− as Pseudo Lead Atoms in closo-[Pd@Pd2Pb10Bi6]4− (pages 13544–13548)

      Dr. Rodica Ababei, Prof. Dr. Werner Massa, Dr. Klaus Harms, Dr. Xiulan Xie, Priv.-Doz. Dr. Florian Weigend and Prof. Dr. Stefanie Dehnen

      Version of Record online: 7 NOV 2013 | DOI: 10.1002/anie.201307795

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      How to simplify a complex thing: A salt of the heaviest intermetalloid cluster known to date, [K([2.2.2]crypt)]4[Pd@Pd2Pb10Bi6]⋅2 en, resulted from a reaction of [Pd(PPh3)4] with [K([2.2.2]crypt)]2(Pb2Bi2)⋅2 en in ethane-1,2-diamine (en). The electron number of the ternary intermetalloid anion accords with Wade–Mingos rules, as the [Pd(η3-Bi3−xPbx)](x+1)− (x=0, 1) 14-electron fragments formed in situ are isolobal with Pb atoms.

    3. Natural Products Chemistry

      Synthesis and Biological Evaluation of Paleo-Soraphens (pages 13549–13552)

      Dr. Hai-Hua Lu, Aruna Raja, Dr. Raimo Franke, Dr. Dirk Landsberg, Dr. Florenz Sasse and Prof. Dr. Markus Kalesse

      Version of Record online: 7 NOV 2013 | DOI: 10.1002/anie.201305331

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      Synthesis can provide molecules such as paleo-soraphens A and B (see scheme) that are genetically encoded but not obtained from the natural source. Although it is unclear whether this is part of an evolutionary process or the consequence of the chemical synthesis, the biological evaluation of these genetically encoded natural products can shed light on how natural products are structurally optimized with respect to their biological profile.

    4. Heterogeneous Catalysis

      How Strain Affects the Reactivity of Surface Metal Oxide Catalysts (pages 13553–13557)

      Dr. Kazuhiko Amakawa, Dr. Lili Sun, Dr. Chunsheng Guo, Dr. Michael Hävecker, Pierre Kube, Prof. Dr. Israel E. Wachs, Soe Lwin, Prof. Dr. Anatoly I. Frenkel, Dr. Anitha Patlolla, Prof. Dr. Klaus Hermann, Prof. Dr. Robert Schlögl and Dr. Annette Trunschke

      Version of Record online: 20 NOV 2013 | DOI: 10.1002/anie.201306620

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      Only uncomfortable seats left: At high surface coverages of molybdenum oxide, at which surface hydroxy anchoring sites are limited, surface metal oxide molecules are forced to be anchored in strained/frustrated configurations. This strain leads to increased reactivity and explains the non-linear coverage dependence sometimes observed in monolayer-type supported metal oxide catalysts.

    5. Light-Induced Angiogenesis

      Regulating Angiogenesis with Light-Inducible AntimiRs (pages 13558–13561)

      Florian Schäfer, Dr. Jasmin Wagner, Andrea Knau, Prof. Dr. Stefanie Dimmeler and Prof. Dr. Alexander Heckel

      Version of Record online: 31 OCT 2013 | DOI: 10.1002/anie.201307502

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      The inhibition of microRNAs (miRs) in a spatiotemporally defined manner by an exogenous trigger would help to specifically target the biological activity and avoid off-target effects. Novel antimiRs directed against miR-92a can be activated by irradiation (see scheme; 3′-UTR=3′-untranslated region) In this way miR-92a is inhibited, the miR-92a target integrin α5 is derepressed, and angiogenesis of endothelial cells is enhanced.

    6. Organocatalysis

      Asymmetric Synthesis of Pyrroloindolones by N-Heterocyclic Carbene Catalyzed [2+3] Annulation of α-Chloroaldehydes with Nitrovinylindoles (pages 13562–13566)

      Qijian Ni, Huan Zhang, Dr. André Grossmann, Charles C. J. Loh, Carina Merkens and Prof. Dr. Dieter Enders

      Version of Record online: 4 NOV 2013 | DOI: 10.1002/anie.201305957

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      NHC-enolate plus 3: N-heterocyclic carbenes (NHCs) serve as organocatalysts for the [2+3] annulation of nitrovinylindoles with α-chloroaldehydes via an intermediate azolium enolate. The method provides trans-disubstituted pyrroloindolones with good yields and excellent diastereo- and enantioselectivities. Further transformations lead to tetracyclic pyrrolo[1,2-a]indoles with potential psychotropic and other bioactivities.

    7. Oxygen Evolution

      Three-Dimensional N-Doped Graphene Hydrogel/NiCo Double Hydroxide Electrocatalysts for Highly Efficient Oxygen Evolution (pages 13567–13570)

      Sheng Chen, Jingjing Duan, Prof. Mietek Jaroniec and Prof. Shi Zhang Qiao

      Version of Record online: 7 NOV 2013 | DOI: 10.1002/anie.201306166

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      A highly hydrated structure was fabricated for catalyzing the oxygen evolution reaction (OER), which demonstrated significantly enhanced catalytic activity, favorable kinetics, and strong durability. The enhanced performance is correlated with the dual-active-site mechanism, and high hydrophilicity of the electrode can dramatically expedite the process of water oxidation into molecular oxygen.

    8. Controllable Optical Activity

      Controllable Optical Activity of Gold Nanorod and Chiral Quantum Dot Assemblies (pages 13571–13575)

      Zhening Zhu, Jun Guo, Wenjing Liu, Zhengtao Li, Bing Han, Prof. Wei Zhang and Prof. Zhiyong Tang

      Version of Record online: 7 NOV 2013 | DOI: 10.1002/anie.201305389

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      The optical coupling between Au nanorods (Au NRs) and chiral quantum dots (QDs) in assemblies is investigated by both experiment and theoretical calculations. The coupled optical activity in the visible-light region can be manipulated by changing either the aspect ratio of Au NRs (see picture; right) or the size of QDs (left).

    9. Synthetic Methods

      [2+2+2] Cycloadditions of Siloxy Alkynes with 1,2-Diazines: From Reaction Discovery to Identification of an Antiglycolytic Chemotype (pages 13576–13579)

      Dr. Timothy J. Montavon, Dr. Yunus E. Türkmen, Noumaan A. Shamsi, Christopher Miller, Chintan S. Sumaria, Prof. Dr. Viresh H. Rawal and Prof. Dr. Sergey A. Kozmin

      Version of Record online: 7 NOV 2013 | DOI: 10.1002/anie.201305711

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      Cycloaddition uncovered: The title reaction produces novel polycyclic compounds with high efficiency and excellent diastereoselectivity under mild reaction conditions. A small-molecule library, synthesized using this reaction, yielded a novel chemotype which inhibited glycolytic ATP production by blocking glucose uptake in CHO-K1 cells. DMF=N,N-dimethylformamide, Tf=trifluoromethanesulfonyl, TIPS=triisopropylsilyl.

    10. Chromophore–Catalyst Assemblies

      Low-Overpotential Water Oxidation by a Surface-Bound Ruthenium-Chromophore–Ruthenium-Catalyst Assembly (pages 13580–13583)

      Michael R. Norris, Dr. Javier J. Concepcion, Dr. Zhen Fang, Prof. Joseph L. Templeton and Prof. Thomas J. Meyer

      Version of Record online: 7 NOV 2013 | DOI: 10.1002/anie.201305951

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      When anchored to nanoITO (indium tin oxide), the ruthenium chromophore–catalyst assembly shown acts as an electrocatalyst for water oxidation, with O2 evolution occurring at an overpotential of 230 mV in 0.1 M HClO4. The potential response of the electrode points to 3 e/2 H+ oxidized [[BOND]RuaIII[BOND]RubIV[DOUBLE BOND]O]5+ as the active form of the assembly.

    11. Polymerization Catalysis

      Replacing Tin in Lactide Polymerization: Design of Highly Active Germanium-Based Catalysts (pages 13584–13587)

      Jia Guo, Dr. Pierre Haquette, Dr. Juliette Martin, Dr. Karine Salim and Prof. Dr. Christophe M. Thomas

      Version of Record online: 26 NOV 2013 | DOI: 10.1002/anie.201306623

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      Most germane: Hexacoordinate germanium(IV) species exhibit unprecedented activities, yet controlled behavior, as initiators for the ring-opening polymerization of rac-lactide to form polylactide polymers (see scheme).

    12. β-Lactam Synthesis

      Stereoselective Synthesis of Chiral α-Amino-β-Lactams through Palladium(II)-Catalyzed Sequential Monoarylation/Amidation of C(sp3)[BOND]H Bonds (pages 13588–13592)

      Qi Zhang, Kai Chen, Weihao Rao, Yuejun Zhang, Fa-Jie Chen and Prof. Dr. Bing-Feng Shi

      Version of Record online: 31 OCT 2013 | DOI: 10.1002/anie.201306625

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      Give Me an Ar, give Me an N! Arylation of the methyl group in a simple derivative of readily available alanine under palladium catalysis was followed by intramolecular amidation at the same position to give chiral α-amino-β-lactams with a wide range of aryl substituents (see scheme; Phth=phthaloyl). The α-amino-β-lactams were obtained in moderate to high yields with good functional-group tolerance and high diastereoselectivity.

    13. Asymmetric Catalysis

      Enantio- and Diastereoselective Assembly of Tetrahydrofuran and Tetrahydropyran Skeletons with All-Carbon-Substituted Quaternary Stereocenters (pages 13593–13596)

      Zhilong Chen and Prof. Dr. Jianwei Sun

      Version of Record online: 19 NOV 2013 | DOI: 10.1002/anie.201306801

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      Chiral phosphoric acids (HB*) catalyze the asymmetric desymmetrization of meso 1,3-diols through mono-transacetalization with a tethered acetal unit (see scheme). This new strategy leads to the efficient assembly of tetrahydrofuran and tetrahydropyran skeletons bearing remote all-carbon-substituted quaternary stereocenters that are not straightforward to access by other methods.

    14. Synthetic Methods

      Synthesis of Substituted Tetrahydrocyclobuta[b]benzofurans by Palladium-Catalyzed Substitution/[2+2] Cycloaddition of Propargylic Carbonates with 2-Vinylphenols (pages 13597–13600)

      Prof. Dr. Masahiro Yoshida, Shoko Ohno and Prof. Dr. Kosuke Namba

      Version of Record online: 31 OCT 2013 | DOI: 10.1002/anie.201306903

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      Radical methods: The title reaction proceeds in the presence of a palladium catalyst to deliver substituted tetrahydrocyclobuta[b]benzofurans in a stereoselective manner (see scheme). A radical mechanism is discussed.

    15. Cycloaddition

      Transfer of Chirality in the Rhodium-Catalyzed Intramolecular [5+2] Cycloaddition of 3-Acyloxy-1,4-enynes (ACEs) and Alkynes: Synthesis of Enantioenriched Bicyclo[5.3.0]decatrienes (pages 13601–13605)

      Dr. Xing-zhong Shu, Casi M. Schienebeck, Wangze Song, Dr. Ilia A. Guzei and Prof. Dr. Weiping Tang

      Version of Record online: 21 OCT 2013 | DOI: 10.1002/anie.201306919

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      Chiral bicycles: Enantioenriched bicyclo[5.3.0]decatrienes were prepared from readily available chiral 3-acyloxy-1,4-enynes (ACEs) for the first time. In most cases, the chirality of the ACEs could be transferred to the bicyclic products with high efficiency. Inversion of the configuration was observed, thus confirming the predictions of previous computational studies.

    16. C[BOND]H Activation

      An Efficient Palladium-Catalyzed C[BOND]H Alkoxylation of Unactivated Methylene and Methyl Groups with Cyclic Hypervalent Iodine (I3+) Oxidants (pages 13606–13610)

      Gang Shan, Xinglin Yang, Yu Zong and Prof. Dr. Yu Rao

      Version of Record online: 8 NOV 2013 | DOI: 10.1002/anie.201307090

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      All the hype: The title reaction has been developed for the facile synthesis of a variety of complex alkyl ethers. Cyclic hypervalent iodine (I3+) reagents serve as oxidants for this unique C[BOND]H alkoxylation reaction. The reaction demonstrates excellent reactivity, good functional-group tolerance, and high yields. Q=8-aminoquinoline-derived auxiliary.

    17. Mesoporous Nanoparticles

      All-Metal Mesoporous Nanocolloids: Solution-Phase Synthesis of Core–Shell Pd@Pt Nanoparticles with a Designed Concave Surface (pages 13611–13615)

      Dr. Hamed Ataee-Esfahani, Dr. Masataka Imura and Prof. Dr. Yusuke Yamauchi

      Version of Record online: 15 NOV 2013 | DOI: 10.1002/anie.201307126

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      Colloidal Pd@Pt nanoparticles with uniform mesopores can be synthesized in one step by a facile solution-phase method involving slow reduction of metal species in strong acidic media. In this system, F127 micelles can directly act as a template to form the mesopores in the product, and the greater reducibility of the Pd species leads to the desired core–shell Pd@Pt nanocolloids.

    18. Asymmetric Catalysis

      Enantioselective N-Heterocyclic Carbene Catalyzed Annulation Reactions with Imidazolidinones (pages 13616–13620)

      Dr. Elizabeth O'Bryan McCusker and Prof. Karl A. Scheidt

      Version of Record online: 18 NOV 2013 | DOI: 10.1002/anie.201307292

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      Add acetic acid: A highly stereoselective N-heterocyclic carbene (NHC)-catalyzed formal [4+2] annulation between α,β-unsaturated aldehydes and imidazolidinones for the synthesis of imidazoles has been developed. Acetic acid serves as a key additive to achieve high chemoselectivity for the formal [4+2] annulation product.

    19. Rechargeable Batteries

      Metal Oxychlorides as Cathode Materials for Chloride Ion Batteries (pages 13621–13624)

      Dr. Xiangyu Zhao, Dr. Zhirong Zhao-Karger, Dr. Di Wang and Prof. Dr. Maximilian Fichtner

      Version of Record online: 7 NOV 2013 | DOI: 10.1002/anie.201307314

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      A key challenge of chloride ion batteries is to develop cathode materials that are stable in the electrolytes. Metal oxychlorides are presented as such a cathode material. The electrochemical performance and the reaction mechanisms of the BiOCl and FeOCl cathode were investigated. Both cathodes showed reversible reactions, including a major conversion reaction and a minor intercalation process, by chloride ion transfer during cycling.

    20. Plant Biosynthetic Pathways

      Minimum Set of Cytochromes P450 for Reconstituting the Biosynthesis of Camalexin, a Major Arabidopsis Antibiotic (pages 13625–13628)

      Andrew P. Klein, Dr. Gülbenk Anarat-Cappillino and Prof. Dr. Elizabeth S. Sattely

      Version of Record online: 21 OCT 2013 | DOI: 10.1002/anie.201307454

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      Bringing it all together: The missing key step in the biosynthesis of camalexin was uncovered by in vitro biochemical characterization. The coupling of Trp- and Cys-derived fragments through C[BOND]S bond formation (see scheme, right) is promoted by an unusual cytochrome P450 CYP71A13. The in vitro reconstitution of the camalexin biosynthesis (left) from Trp and Cys was achieved using just three cytochromes P450. IAN=indole-3-acetonitrile.

    21. C[BOND]C Bond Formation

      1,1-Carbozirconation: Unusual Reaction of an Alkyne with a Methyl Zirconocene Cation and Subsequent Frustrated Lewis Pair Like Reactivity (pages 13629–13632)

      Dr. Xin Xu, Dr. Gerald Kehr, Dr. Constantin G. Daniliuc and Prof. Dr. Gerhard Erker

      Version of Record online: 12 NOV 2013 | DOI: 10.1002/anie.201307493

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      Boron chemistry without the boron: In a reaction analogous to 1,1-carboboration, [Cp*2Zr[BOND]CH3]+ reacts with diphenylphosphino(trimethylsilyl)acetylene by 1,1-carbozirconation to give a vicinal [Zr]+/P system. Like B/P frustrated Lewis pairs, the [Zr]+/P system undergoes 1,2-addition to unsaturated compounds (including CO2) and reaction with metal complexes and up to three equivalents of CO.

    22. Photoactivated Platinum Complexes

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      De Novo Generation of Singlet Oxygen and Ammine Ligands by Photoactivation of a Platinum Anticancer Complex (pages 13633–13637)

      Dr. Yao Zhao, Dr. Nicola J. Farrer, Dr. Huilin Li, Jennifer S. Butler, Ruth J. McQuitty, Dr. Abraha Habtemariam, Prof. Dr. Fuyi Wang and Prof. Dr. Peter J. Sadler

      Version of Record online: 25 OCT 2013 | DOI: 10.1002/anie.201307505

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      Worth the excitement: Highly reactive oxygen and nitrogen species are generated by photoactivation of the anticancer platinum(IV) complex trans,trans,trans-[Pt(N3)2(OH)2(MA)(Py)] (MA=methylamine, Py=pyridine). Singlet oxygen is formed from the hydroxido ligands and not from dissolved oxygen, and ammine ligands are products from the conversion of azido ligands to nitrenes. Both processes can induce oxidation of guanine.

    23. Electrocatalysts

      Hydrogen Evolution by Tungsten Carbonitride Nanoelectrocatalysts Synthesized by the Formation of a Tungsten Acid/Polymer Hybrid In Situ (pages 13638–13641)

      Dr. Yong Zhao, Dr. Kazuhide Kamiya, Prof. Dr. Kazuhito Hashimoto and Prof. Dr. Shuji Nakanishi

      Version of Record online: 23 OCT 2013 | DOI: 10.1002/anie.201307527

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      A step forward for tungsten: Nitrogen-rich tungsten carbonitride (WCN) nanomaterials can act as stable and efficient hydrogen evolution electrocatalysts with a much higher activity than conventional WCN materials. The use of a polymerization process provides a unique synthetic route to H2WO4 nanoparticles, which can then be used to synthesize the WCN-derived catalysts.

    24. Asymmetric Catalysis

      Copper-Free Asymmetric Allylic Alkylation of Trisubstituted Cyclic Allyl Bromides Using Grignard Reagents (pages 13642–13646)

      David Grassi and Prof. Dr. Alexandre Alexakis

      Version of Record online: 7 NOV 2013 | DOI: 10.1002/anie.201307591

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      AAA: The asymmetric allylic alkylation (AAA) of trisubstituted cyclic allyl bromides with Grignard reagents is catalytic (2 mol % of ligand) and regioselective (SN2'/SN2=91:9[RIGHTWARDS ARROW]100:0). The quaternary carbon centers are formed with good to high enantioselectivity (e.r.=81.5:19.5[RIGHTWARDS ARROW]96:4).

    25. Multicomponent Reactions

      A Streamlined Strategy for Aglycone Assembly and Glycosylation (pages 13647–13650)

      Dr. Katherine M. Partridge, Dr. Scott J. Bader, Dr. Zachary A. Buchan, Dr. Christopher E. Taylor and Prof. John Montgomery

      Version of Record online: 21 OCT 2013 | DOI: 10.1002/anie.201307680

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      Multipurpose sugars: Carbohydrate-derived silane reagents are utilized as the reductant for nickel-catalyzed aldehyde–alkyne reductive coupling reactions and as the glycosyl donor for subsequent intramolecular glycosylation. The approach enables the assembly of the carbon–carbon framework and stereochemical features of an aglycone while simultaneously establishing the site of glycosylation.

    26. Synthetic Methods

      Deaminative and Decarboxylative Catalytic Alkylation of Amino Acids with Ketones (pages 13651–13655)

      Nishantha Kalutharage and Prof. Dr. Chae S. Yi

      Version of Record online: 31 OCT 2013 | DOI: 10.1002/anie.201307766

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      It cuts two ways: The cationic [Ru-H] complex catalyzes selective coupling of α- and β-amino acids with ketones to form α-alkylated ketone products. The reaction involves C[BOND]C and C[BOND]N bond cleavage which result in regio- and stereoselective alkylation using amino acids. A broad substrate scope and high functional-group tolerance is demonstrated.

    27. Synthesis and Applications of α-Trifluoromethylated Alkylboron Compounds (pages 13656–13660)

      O. Andreea Argintaru, DaWeon Ryu, Ioana Aron and Prof. Gary A. Molander

      Version of Record online: 7 NOV 2013 | DOI: 10.1002/anie.201308036

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      RBF3K is a chemist's BFF: A metal-free synthetic route to unprecedented organoboron compounds bearing an α-trifluoromethyl substituent, employing a variety of trifluoroborate (RBF3K) starting materials, is reported. These substrates represent the first isolated α-trifluoromethylated alkylboron building blocks, and these reagents lead to a variety of useful bench-stable, synthetic intermediates. Pin=pinacol.

    28. Ultrasensitive Analysis

      Ultrasensitive and Fast Bottom-up Analysis of Femtogram Amounts of Complex Proteome Digests (pages 13661–13664)

      Dr. Liangliang Sun, Dr. Guijie Zhu, Yimeng Zhao, Xiaojing Yan, Si Mou and Prof. Dr. Norman J. Dovichi

      Version of Record online: 31 OCT 2013 | DOI: 10.1002/anie.201308139

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      Femtogram proteomics: An ultrasensitive capillary zone electrophoresis–mass spectrometry system that is based on an improved nanospray interface has been developed. This system is used for the analysis of picogram to femtogram amounts of E. coli digests; for example, over 100 proteins were identified from 16 pg digests by tandem mass spectrometry. AMTs=accurate mass and time tags.

    29. Self-Organization

      Panoscopic Structures by Hierarchical Cascade Self-Assembly of Inorganic Surfactants with Magnetic Heads Containing Dysprosium Ions (pages 13665–13670)

      Prof. Dr. Sebastian Polarz, Christian Bährle, Dr. Steve Landsmann and Alexander Klaiber

      Version of Record online: 22 OCT 2013 | DOI: 10.1002/anie.201303565

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      Magnetic moustaches: Inorganic surfactants (I-SURFs) with head groups containing Dy3+ undergo a hierarchical self-organization cascade controlled by magnetic interactions. The resulting aggregates are shaped like dumbbells with frayed, moustache-like ends.

    30. Redox-Sensing Nanocrystals

      Doped Nanocrystals as Plasmonic Probes of Redox Chemistry (pages 13671–13675)

      Prof. Prashant K. Jain, Karthish Manthiram, Jesse H. Engel, Sarah L. White, Jacob A. Faucheaux and Prof. A. Paul Alivisatos

      Version of Record online: 23 OCT 2013 | DOI: 10.1002/anie.201303707

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      A (nano)crystal-clear view: With doped semiconductor nanocrystals, local chemical events can be probed through their perturbation of the carrier density of the nanocrystal. Examples demonstrate that redox processes and ligand chemistry can induce changes in the vacancy density within copper(I) sulfide nanorods, allowing such events to be detected by strong shifts in localized surface plasmon resonance.

    31. Fluorescent Dyes

      Regiospecific N-Heteroarylation of Amidines for Full-Color-Tunable Boron Difluoride Dyes with Mechanochromic Luminescence (pages 13676–13680)

      Dr. Dongbing Zhao, Dr. Gaocan Li, Prof. Dr. Di Wu, Xurong Qin, Dr. Patrik Neuhaus, Yangyang Cheng, Dr. Shuaijun Yang, Prof. Zhiyun Lu, Prof. Xuemei Pu, Chao Long and Prof. Dr. Jingsong You

      Version of Record online: 7 NOV 2013 | DOI: 10.1002/anie.201304824

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      Colors to dye for: Palladium-catalyzed regiospecific N-heteroarylations of amidines with 2-halo-N-heteroarenes leads to a structurally diverse library of BF2/amidine-based complexes. These dyes not only present full-visible-color solid-state emissions with large Stokes shifts and high fluorescence quantum yields, but also exhibit a full-color-tunable mechanofluorochromic nature.

    32. DNA Recognition

      Conjugation of Peptide Nucleic Acid with a Pyrrole/Imidazole Polyamide to Specifically Recognize and Cleave DNA (pages 13681–13684)

      Wataru Kameshima, Dr. Takumi Ishizuka, Dr. Masafumi Minoshima, Makoto Yamamoto, Prof. Dr. Hiroshi Sugiyama, Prof. Dr. Yan Xu and Prof. Dr. Makoto Komiyama

      Version of Record online: 23 OCT 2013 | DOI: 10.1002/anie.201305489

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      Cut loose: A pseudocomplementary peptide nucleic acid was tethered to a pyrrole/imidazole hairpin polyamide, and was used to selectively target a specific DNA sequence. Binding even occurs under high salt conditions. Furthermore, the conjugate facilitated sequence-specific scission of long dsDNA. This simple approach promises to resolve the technical difficulties in targeting DNA sequences with PNA.

    33. THz Excitation of Water

      Ultrafast Energy Transfer to Liquid Water by Sub-Picosecond High-Intensity Terahertz Pulses: An Ab Initio Molecular Dynamics Study (pages 13685–13687)

      Pankaj Kr. Mishra, Dr. Oriol Vendrell and Prof. Dr. Robin Santra

      Version of Record online: 23 OCT 2013 | DOI: 10.1002/anie.201305991

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      Sub-picosecond heating of bulk water is accomplished by ultrashort and intense THz pulses which are able to transfer a large amount of energy to the liquid. The energy transferred corresponds to a temperature jump of about 600 K. Liquid water becomes a structureless and hot gas-like system (see picture) still at the density of the liquid, in which the hydrogen-bonding structure has been washed out.

    34. Organocatalysis

      Direct Catalytic Asymmetric Synthesis of N-Heterocycles from Commodity Acid Chlorides by Employing α,β-Unsaturated Acylammonium Salts (pages 13688–13693)

      Dr. Sreekumar Vellalath, Khoi N. Van and Prof. Dr. Daniel Romo

      Version of Record online: 31 OCT 2013 | DOI: 10.1002/anie.201306050

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      Taming the beast, asymmetrically: Modulation of the reactivity of acid chlorides, using cinchona alkaloid catalysts, results in chiral α,β-unsaturated acylammoniums, which react with nucleophiles enantioselectively to give pyrrolidinones, piperid-2-ones, and dihydropyridinones. This nucleophile-catalyzed Michael/proton transfer/lactamization or lactonization organocascade leads to chiral intermediates previously employed for the synthesis of bioactive pharmaceuticals.

    35. Intracellular Monitoring

      Plasmonic Nanoprobes for Real-Time Optical Monitoring of Nitric Oxide inside Living Cells (pages 13694–13698)

      Dr. Pilar Rivera_Gil, Carmen Vazquez-Vazquez, Dr. Vincenzo Giannini, Prof. M. Pilar Callao, Prof. Wolfgang J. Parak, Prof. Miguel A. Correa-Duarte and Prof. Ramon A. Alvarez-Puebla

      Version of Record online: 12 NOV 2013 | DOI: 10.1002/anie.201306390

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      An optical sensor was developed for the quantitative determination of intracellular nitric oxide. The sensor consists of plasmonic nanoprobes (see picture, left) that have a coating of mesoporous silica and an inner gold island film functionalized with a chemoreceptor for NO.

    36. Sugar Poly(orthoester)

      Synthesis of Highly pH-Responsive Glucose Poly(orthoester) (pages 13699–13702)

      Lingyao Li, Yi Xu, Ian Milligan, Liye Fu, Emily A. Franckowiak and Prof. Wenjun Du

      Version of Record online: 29 NOV 2013 | DOI: 10.1002/anie.201306391

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      We love sugar! The synthesis of sugar-based polymers, wherein all sugar units are connected by orthoester linkages, was achieved by polymerization of a glucose-based difunctional AB monomer (see scheme, left). When tetra-n-butylammonium iodide (TBAI) was used as a promoter, polymers with molecular weights up to 6.9 kDa were synthesized in a polycondensation manner. These polymers are highly pH-responsive with a half-life of 0.9 hours at pH 6.

    37. Photodynamic Switches

      Photodynamic Chiral Molecular Switches with Thermal Stability: From Reflection Wavelength Tuning to Handedness Inversion of Self-Organized Helical Superstructures (pages 13703–13707)

      Dr. Yannian Li, Dr. Chenming Xue, Mengfei Wang, Dr. Augustine Urbas and Prof. Quan Li

      Version of Record online: 22 OCT 2013 | DOI: 10.1002/anie.201306396

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      A good turn: Three compounds that bear two axially chiral bridged binaphthyl units were developed as photodynamic chiral dopants for nematic liquid crystals. For compounds with suitable bridge lengths, a change in the dihedral angle induced a switch of the binaphthyl units from the cisoid to the transoid form upon UV irradiation, which led to an inversion of the handedness of the helices.

    38. Water Oxidation

      Optically Transparent Water Oxidation Catalysts Based on Copper Nanowires (pages 13708–13711)

      Dr. Zuofeng Chen, Dr. Aaron R. Rathmell, Dr. Shengrong Ye, Adria R. Wilson and Prof. Benjamin J. Wiley

      Version of Record online: 18 OCT 2013 | DOI: 10.1002/anie.201306585

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      Let the light shine through: A transparent film of copper nanowires was transformed into an electrocatalyst for water oxidation by electrodepostion of Ni or Co onto the surface of the nanowires. These core–shell nanowire networks exhibit electrocatalytic performance equivalent to metal oxide films of similar composition, but are several times more transparent.

    39. Sensors

      Selective and Sensitive Chromofluorogenic Detection of the Sulfite Anion in Water Using Hydrophobic Hybrid Organic–Inorganic Silica Nanoparticles (pages 13712–13716)

      Luis Enrique Santos-Figueroa, Cristina Giménez, Dr. Alessandro Agostini, Dr. Elena Aznar, Dr. María D. Marcos, Dr. Félix Sancenón, Prof. Ramón Martínez-Máñez and Prof. Pedro Amorós

      Version of Record online: 7 NOV 2013 | DOI: 10.1002/anie.201306688

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      In water and wine: Chromofluorogenic detection of the sulfite anion in pure water was accomplished by using a new hybrid organic–inorganic material that contained a probe entrapped in hydrophobic biomimetic cavities. This material was used for the detection of sulfite in red wine.

    40. Asymmetric Synthesis

      One-Pot Zinc-Promoted Asymmetric Alkynylation/Brook-Type Rearrangement/Ene–Allene Cyclization: Highly Selective Formation of Three New Bonds and Two Stereocenters in Acyclic Systems (pages 13717–13721)

      Polina Smirnov, Dr. Jomon Mathew, Dr. Anne Nijs, Einat Katan, Dr. Miriam Karni, Prof. Dr. Carsten Bolm, Prof. Dr. Yitzhak Apeloig and Prof. Dr. Ilan Marek

      Version of Record online: 23 OCT 2013 | DOI: 10.1002/anie.201306749

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      It's as easy as 1, 2, 3: In a one-pot sequence, two stereocenters and three new bonds were created with high selectivity through an asymmetric alkynylation of acyl silanes, a tandem Brook-type rearrangement and Zn–ene–allene cyclization, the addition of an electrophile, and finally oxidation (see scheme). The straightforward nature of the synthetic procedure contrasts strongly with the complexity of the densely functionalized products obtained.

    41. Radical Ions

      Isolation and Characterization of the Cycloparaphenylene Radical Cation and Dication (pages 13722–13726)

      Dr. Eiichi Kayahara, Takahiko Kouyama, Prof. Dr. Tatsuhisa Kato, Dr. Hikaru Takaya, Dr. Nobuhiro Yasuda and Prof. Dr. Shigeru Yamago

      Version of Record online: 19 NOV 2013 | DOI: 10.1002/anie.201306881

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      Charged nanobelts: The radical cation and the dication of [8]cycloparaphenylene ([8]CPP) were prepared and isolated as hexahaloantimonate salts by the one- or two-electron chemical oxidation of [8]CPP with NOSbF6 or SbCl5. ESR spectroscopy of CPP.+ and single-crystal X-ray analysis of CPP2+ demonstrated that the spin and charge were equally and fully delocalized over the para-phenylene rings.

    42. Porphyrinoids

      Selective Synthesis of a [32]Octaphyrin(1.0.1.0.1.0.1.0) Bis(palladium) Complex by a Metal-Templated Strategy (pages 13727–13730)

      Hiromitsu Kido, Prof. Dr. Ji-Young Shin and Prof. Dr. Hiroshi Shinokubo

      Version of Record online: 23 OCT 2013 | DOI: 10.1002/anie.201306905

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      A shapely figure: A [32]octaphyrin(1.0.1.0.1.0.1.0) bis[palladium(II)] complex was selectively obtained through a metal-templated intermolecular homocoupling of a α,α′-dibromodipyrrin palladium(II) complex without formation the norcorrole. The weak antiaromatic character of the figure-eight [32]octaphyrin(1.0.1.0.1.0.1.0) system has been elucidated by spectroscopic measurements and DFT calculations.

    43. Waste Heat Chemistry

      A Microvascular System for Chemical Reactions Using Surface Waste Heat (pages 13731–13734)

      Du Thai Nguyen and Dr. Aaron P. Esser-Kahn

      Version of Record online: 4 NOV 2013 | DOI: 10.1002/anie.201306928

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      Coffee-powered chemistry: Low-grade waste heat on surfaces can be used to drive chemical reactions, including the regeneration of a CO2 capture solution. Flowing two-phase heat transfer has been implemented within microvascular systems. This stripping system can be adapted to pre-fabricated surfaces, as demonstrated by a coffee mug containing a 1.2 m long microchannel. MEA=monoethanolamine

    44. Asymmetric Catalysis

      One-Pot Tandem Approach to Spirocyclic Oxindoles Featuring Adjacent Spiro-Stereocenters (pages 13735–13739)

      Yun-Lin Liu, Prof. Dr. Xin Wang, Yu-Lei Zhao, Feng Zhu, Xing-Ping Zeng, Long Chen, Prof. Dr. Cui-Hong Wang, Prof. Dr. Xiao-Li Zhao and Prof. Dr. Jian Zhou

      Version of Record online: 7 NOV 2013 | DOI: 10.1002/anie.201307250

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      All in a sequence: An organocatalyzed Morita–Baylis–Hillman (MBH)/bromination/[3+2] annulation sequence for highly stereoselective syntheses of bis(spirooxindole)s featuring adjacent spiro-stereocenters is described. The key step is an unprecedented catalytic asymmetric [3+2] annulation of isatin-derived MBH adducts, containing a tetrasubstituted alkene moiety, with isatins.

    45. Smart Foldamers

      Control over Unfolding Pathways by Localizing Photoisomerization Events within Heterosequence Oligoazobenzene Foldamers (pages 13740–13744)

      Dr. Zhilin Yu and Prof. Dr. Stefan Hecht

      Version of Record online: 19 NOV 2013 | DOI: 10.1002/anie.201307378

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      From the inside out or from the outside in? Two photoswitchable foldamers that incorporate azobenzene moieties as the energy-acceptor units have been designed. The pathway of helix unfolding can be controlled by localizing these photoinduced triggers (shown in red) either at the core (left) or at the termini (right) of the helix.

    46. Heterocycle Synthesis

      Scalable Synthesis of Oxazolones from Propargylic Alcohols through Multistep Palladium(II) Catalysis: β-Selective Oxidative Heck Coupling of Cyclic Sulfonyl Enamides and Aryl Boroxines (pages 13745–13750)

      Dr. Santosh Kumar Alamsetti, Dr. Andreas K. Å. Persson, Tuo Jiang and Prof. Dr. Jan-E. Bäckvall

      Version of Record online: 31 OCT 2013 | DOI: 10.1002/anie.201307471

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      A whale of a scale: The title oxidative Heck coupling proceeded with unusual β selectivity to generate a variety of branched substituted oxazolones (see scheme; Ts=p-toluenesulfonyl). The three-step synthesis from readily available starting materials with a simple palladium catalyst and inexpensive reagents could be carried out in a single reaction vessel or scaled up for the preparation of large amounts of these amino acid precursors.

    47. Electrocatalysis

      Two-Dimensional Hybrid Nanosheets of Tungsten Disulfide and Reduced Graphene Oxide as Catalysts for Enhanced Hydrogen Evolution (pages 13751–13754)

      Jieun Yang, Damien Voiry, Seong Joon Ahn, Dongwoo Kang, Ah Young Kim, Prof. Manish Chhowalla and Prof. Hyeon Suk Shin

      Version of Record online: 7 NOV 2013 | DOI: 10.1002/anie.201307475

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      Composite materials: Tungsten disulfide and WS2/reduced graphene oxide (WS2/rGO) nanosheets were fabricated by hydrothermal synthesis using tungsten chloride, thioacetamide, and graphene oxide (GO) as starting materials. The WS2 nanosheets are efficiently templated on the rGO layer. The WS2/rGO hybrid nanosheets show much better electrocatalytic activity for the hydrogen evolution reaction (see picture) than WS2 nanosheets alone.

    48. Crystal Engineering

      Hydrolytic Conversion of a Metal–Organic Polyhedron into a Metal–Organic Framework (pages 13755–13759)

      Arijit Mallick, Bikash Garai, Dr. David Díaz Díaz and Dr. Rahul Banerjee

      Version of Record online: 7 NOV 2013 | DOI: 10.1002/anie.201307486

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      Twist and release: The metal–organic polyhedron 1 synthesized from 5-(prop-2-ynyloxy)isophthalic acid and Cu(NO3)2⋅ 3 H2O has a hydrophobic outer surface and a hydrophilic inner core. In an aqueous medium, the resulting polarity gradient led to the transformation of 1 into the 2D metal–organic framework 2. This unique phenomenon enabled the gradual release of entrapped drug molecules.

    49. Enzyme inhibition

      Carborane-Based Carbonic Anhydrase Inhibitors (pages 13760–13763)

      Dr. Jiří Brynda, Dr. Pavel Mader, Dr. Václav Šícha, Dr. Milan Fábry, Kristýna Poncová, Dr. Mario Bakardiev, Dr. Bohumír Grüner, Dr. Petr Cígler and Dr. Pavlína Řezáčová

      Version of Record online: 4 NOV 2013 | DOI: 10.1002/anie.201307583

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      CA inhibitors: Human carbonic anhydrases (CAs) are diagnostic and therapeutic targets. Various carborane cages are shown to act as active-site-directed inhibitors, and substitution with a sulfamide group and other substituents leads to compounds with high selectivity towards the cancer-specific isozyme IX. Crystal structures of the carboranes in the active site provide information that can be applied to the structure-based design of specific inhibitors.

    50. Mesoporous Microspheres

      A General “Surface-Locking” Approach toward Fast Assembly and Processing of Large-Sized, Ordered, Mesoporous Carbon Microspheres (pages 13764–13768)

      Dr. Zhangxiong Wu, Dr. Winston Duo Wu, Dr. Wenjie Liu, Prof. Dr. Cordelia Selomulya, Prof. Dr. Xiao Dong Chen and Prof. Dr. Dongyuan Zhao

      Version of Record online: 12 NOV 2013 | DOI: 10.1002/anie.201307608

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      Drying to meet you: Using microfluidic jet spray drying technology in conjunction with the evaporation-induced self-assembly strategy gives fast assembly (2 s) of mesoporous carbon microspheres. The key feature of the drying is the formation of a rigid silica crust which locks the particle size and shape.

    51. Metal–Organic Frameworks

      A Cationic Metal–Organic Framework Consisting of Nanoscale Cages: Capture, Separation, and Luminescent Probing of Cr2O72− through a Single-Crystal to Single-Crystal Process (pages 13769–13773)

      Dr. Xinxiong Li, Hongyan Xu, Fanzhen Kong and Prof. Dr. Ruihu Wang

      Version of Record online: 31 OCT 2013 | DOI: 10.1002/anie.201307650

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      Dichromate capture: A 3D cationic metal–organic framework consisting of distorted octahedral and tetrahedral cages was constructed by using AgI and 4,4′-bis(1,2,4-triazole). The complex exhibits fast exchange, high trapping capacity, and good selectivity for Cr2O72− through single-crystal to single-crystal transformation. The complex also features a bluish violet luminescence that is distinctly quenched after Cr2O72− exchange.

    52. DNA Structures

      Effect of Pressure on the Stability of G-Quadruplex DNA: Thermodynamics under Crowding Conditions (pages 13774–13778)

      Dr. Shuntaro Takahashi and Prof. Naoki Sugimoto

      Version of Record online: 25 OCT 2013 | DOI: 10.1002/anie.201307714

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      Under pressure: A DNA G-quadruplex was unfolded under high pressure, but crowding conditions repressed this effect owing to enthalpic contributions. Volumetric analysis showed that ethylene glycol or poly(ethylene glycol) decreased the volume change of the transition by more than fourfold owing to the alteration of the number and/or radii of hydrating water molecules.

    53. Biodetection

      Graphene Oxide as a Pathogen-Revealing Agent: Sensing with a Digital-Like Response (pages 13779–13783)

      Dr. Eden Morales-Narváez, Dr. Abdel-Rahim Hassan and Prof. Dr. Arben Merkoçi

      Version of Record online: 7 NOV 2013 | DOI: 10.1002/anie.201307740

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      Turned ON by a pathogen: A highly sensitive pathogen-detection system has been designed and evaluated for the sensing of E. coli bacteria in diverse matrices. It employs antibody–quantum dot (Ab-QD) probes and exploits the extraordinary two-dimensional structure and fluorescence-quenching capabilities of graphene oxide.

    54. Conductive Paper

      Written-in Conductive Patterns on Robust Graphene Oxide Biopaper by Electrochemical Microstamping (pages 13784–13788)

      Kesong Hu, Lorenzo S. Tolentino, Dr. Dhaval D. Kulkarni, Dr. Chunhong Ye, Prof. Satish Kumar and Prof. Vladimir V. Tsukruk

      Version of Record online: 8 NOV 2013 | DOI: 10.1002/anie.201307830

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      The silk road: By employing silk fibroin as a binder between graphene oxide films and aluminum foil for a facile, highly localized reduction process, conductive paper is reinvented. The flexible, robust biographene papers have high toughness and electrical conductivity. This electrochemical written-in approach is readily applicable for the fabrication of conductive patterned papers (see picture) with complex circuitries.

    55. NMR Spectroscopy

      Breaking Pseudo-Symmetry in Multiantennary Complex N-Glycans Using Lanthanide-Binding Tags and NMR Pseudo-Contact Shifts (pages 13789–13793)

      Dr. Angeles Canales, Dr. Alvaro Mallagaray, Prof. Dr. Javier Pérez-Castells, Irene Boos, Prof. Dr. Carlo Unverzagt, Dr. Sadine André, Prof. Dr. Hans-Joachim Gabius, Prof. Dr. Francisco Javier Cañada and Prof. Dr. Jesús Jiménez-Barbero

      Version of Record online: 4 NOV 2013 | DOI: 10.1002/anie.201307845

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      Controlling NMR shifts by lanthanides tagged to a “symmetrical” N-glycan (see picture) reveals individual resonances for the residues of the otherwise identical A and B arms. This method provides a global perspective of conformational features and interactions in solution.

    56. Membrane Reactors

      Natural Gas to Fuels and Chemicals: Improved Methane Aromatization in an Oxygen-Permeable Membrane Reactor (pages 13794–13797)

      Zhengwen Cao, Prof. Dr. Heqing Jiang, Dr. Huixia Luo, Dr. Stefan Baumann, Dr. Wilhelm A. Meulenberg, Dr. Jens Assmann, Prof. Dr. Leslaw Mleczko, Dr. Yi Liu and Prof. Dr. Jürgen Caro

      Version of Record online: 7 NOV 2013 | DOI: 10.1002/anie.201307935

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      Adding value with membranes: Improved methane aromatization was achieved by using an oxygen-permeable membrane. The resulting membrane reactor shows a superior methane conversion and a higher resistance towards catalyst deactivation.

    57. Asymmetric Organocatalysis

      Atropisomeric Chiral Dienes in Asymmetric Catalysis: C2-Symmetric (Z,Z)-2,3-Bis[1-(diphenylphosphinyl)ethylidene]tetralin as a Highly Active Lewis Base Organocatalyst (pages 13798–13802)

      Prof. Masamichi Ogasawara, Prof. Shunsuke Kotani, Hikaru Nakajima, Haruka Furusho, Mitsuru Miyasaka, Yasushi Shimoda, Dr. Wei-Yi Wu, Prof. Masaharu Sugiura, Prof. Tamotsu Takahashi and Prof. Makoto Nakajima

      Version of Record online: 25 OCT 2013 | DOI: 10.1002/anie.201308112

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      Diene catalysts with a twist: The title C2-symmetric tetralin-fused 1,3-butadiene derivative is atropisomeric and can be resolved into the two helical enantiomers. The optically pure compound showed excellent enantioselectivity as well as unusually high catalytic activity as a chiral Lewis basic organocatalyst in the asymmetric allylation of various aldehydes with β-substituted allyltrichlorosilanes (see scheme).

    58. Photoinduced Protein Delivery

      Wavelength-Controlled Photocleavage for the Orthogonal and Sequential Release of Multiple Proteins (pages 13803–13807)

      Dr. Malar A. Azagarsamy and Prof. Kristi S. Anseth

      Version of Record online: 31 OCT 2013 | DOI: 10.1002/anie.201308174

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      On the right wavelength: Photolabile molecular units that undergo photocleavage under light of different wavelengths can be used for the independent release of different dyes/proteins from a single, preloaded storage hydrogel (see scheme). The controlled release of each protein allowed them to be delivered sequentially and at experimenter-determined times.

    59. Catalyst Stability

      Stabilization of Copper Catalysts for Liquid-Phase Reactions by Atomic Layer Deposition (pages 13808–13812)

      Brandon J. O'Neill, David H. K. Jackson, Dr. Anthony J. Crisci, Carrie A. Farberow, Fengyuan Shi, Dr. Ana C. Alba-Rubio, Dr. Junling Lu, Dr. Paul J. Dietrich, Dr. Xiangkui Gu, Dr. Christopher L. Marshall, Prof. Peter C. Stair, Dr. Jeffrey W. Elam, Dr. Jeffrey T. Miller, Prof. Fabio H. Ribeiro, Prof. Paul M. Voyles, Prof. Jeffrey Greeley, Prof. Manos Mavrikakis, Prof. Susannah L. Scott, Prof. Thomas F. Kuech and Prof. James A. Dumesic

      Version of Record online: 26 NOV 2013 | DOI: 10.1002/anie.201308245

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      Catalytic Armoring: Atomic layer deposition (ALD) of alumina overcoats has been employed to stabilize base metal catalysts against sintering and leaching in liquid-phase conditions. Kinetic studies, characterization of the materials, and theoretical studies were used to elucidate the mechanism by which this stabilization of base metal nanoparticles is achieved.

    60. Drug Delivery

      Two-Photon-Triggered Drug Delivery in Cancer Cells Using Nanoimpellers (pages 13813–13817)

      Jonas Croissant, Dr. Marie Maynadier, Audrey Gallud, Dr. Harmel Peindy N'Dongo, Dr. Jeff L. Nyalosaso, Dr. Gaëlle Derrien, Dr. Clarence Charnay, Dr. Jean-Olivier Durand, Dr. Laurence Raehm, Prof. Françoise Serein-Spirau, Dr. Nathalie Cheminet, Dr. Thibaut Jarrosson, Dr. Olivier Mongin, Dr. Mireille Blanchard-Desce, Dr. Magali Gary-Bobo, Dr. Marcel Garcia, Dr. Jie Lu, Prof. Fuyuhiko Tamanoi, Dr. Derrick Tarn, Tania M. Guardado-Alvarez and Prof. Jeffrey I. Zink

      Version of Record online: 7 NOV 2013 | DOI: 10.1002/anie.201308647

      Thumbnail image of graphical abstract

      A therapy of cancer cells: Two-photon-triggered camptothecin delivery (see picture) with nanoimpellers was studied in MCF-7 breast cancer cells. A fluorophore with a high two-photon absorption cross-section was first incorporated in the nanoimpellers. Fluorescence resonance energy transfer (FRET) from the fluorophore to the azobenzene moiety was demonstrated.

    61. Eelctrocatalysis

      “Metal-Free” Catalytic Oxygen Reduction Reaction on Heteroatom-Doped Graphene is Caused by Trace Metal Impurities (pages 13818–13821)

      Lu Wang, Dr. Adriano Ambrosi and Prof. Martin Pumera

      Version of Record online: 25 NOV 2013 | DOI: 10.1002/anie.201309171

      Thumbnail image of graphical abstract

      Carbon materials: Heteroatom-doped graphene surfaces are used as electrocatalysts for the oxygen reduction reaction. The claimed “metal-free” electrocatalysis of the oxygen reduction reaction is caused by metallic impurities (see picture) present within the graphene materials.

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