Angewandte Chemie International Edition

Cover image for Vol. 50 Issue 26

June 20, 2011

Volume 50, Issue 26

Pages 5773–5971

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Book Reviews
    9. Highlights
    10. Review
    11. Communications
    12. Preview
    1. Cover Picture: Connecting Chemotypes and Phenotypes of Cultured Marine Microbial Assemblages by Imaging Mass Spectrometry (Angew. Chem. Int. Ed. 26/2011) (page 5773)

      Dr. Yu-Liang Yang, Dr. Yuquan Xu, Roland D. Kersten, Wei-Ting Liu, Michael J. Meehan, Prof. Dr. Bradley S. Moore, Prof. Dr. Nuno Bandeira and Prof. Dr. Pieter C. Dorrestein

      Article first published online: 11 MAY 2011 | DOI: 10.1002/anie.201102745

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      Imaging mass spectrometry has been used to study microbes found on the Scripps pier at the Scripps Institution of Oceanography of the University of California, San Diego (shown in the cover picture) that sits in the Pacific ocean. P. C. Dorrestein and co-workers describe in their Communication on page 5839 ff. how this technique can be used to connect the chemistry of microbial metabolic interactions with phenotypic changes as well as to uncover chemical phenotypes that cannot be observed by the naked eye.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Book Reviews
    9. Highlights
    10. Review
    11. Communications
    12. Preview
    1. Inside Cover: Extension of The Stöber Method to the Preparation of Monodisperse Resorcinol–Formaldehyde Resin Polymer and Carbon Spheres (Angew. Chem. Int. Ed. 26/2011) (page 5774)

      Dr. Jian Liu, Prof. Shi Zhang Qiao, Dr. Hao Liu, Dr. Jun Chen, Ajay Orpe, Prof. Dongyuan Zhao and Prof. Gao Qing (Max) Lu

      Article first published online: 3 JUN 2011 | DOI: 10.1002/anie.201103443

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      From the synthesis of silica spheres the well-known Stöber method has been adapted for the preparation of monodisperse polymer spheres from resorcinol–formaldehyde (RF) resin and of carbon “Stöber” spheres. In their Communication on page 5947 ff. S. Z. Qiao, G. Q. (Max) Lu, and co-workers report this low-cost procedure, which provides a tunable particle size ranging from 200 to 1000 nm. It is expected that the Stöber method can be adapted to prepare Stöber spheres with different compositions.

  3. Back Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Book Reviews
    9. Highlights
    10. Review
    11. Communications
    12. Preview
    1. Back Cover: Continuous In Situ Generation, Separation, and Reaction of Diazomethane in a Dual-Channel Microreactor (Angew. Chem. Int. Ed. 26/2011) (page 5774)

      Dr. Ram Awatar Maurya, Dr. Chan Pil Park, Jang Han Lee and Prof. Dr. Dong-Pyo Kim

      Article first published online: 3 JUN 2011 | DOI: 10.1002/anie.201103448

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      Performing organic transformations with toxic, sensitive, and explosive volatile chemicals or gaseous intermediates has always been challenging in both research and industry. In their Communication on page 5952 ff., D.-P. Kim and co-workers describe a simple microchemical approach for the continuous in situ generation, on-demand separation, and reaction of toxic and explosive diazomethane.

  4. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Book Reviews
    9. Highlights
    10. Review
    11. Communications
    12. Preview
    1. Graphical Abstract: Angew. Chem. Int. Ed. 26/2011 (pages 5777–5787)

      Article first published online: 15 JUN 2011 | DOI: 10.1002/anie.201190051

  5. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Book Reviews
    9. Highlights
    10. Review
    11. Communications
    12. Preview
  6. Author Profile

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Book Reviews
    9. Highlights
    10. Review
    11. Communications
    12. Preview
    1. Kenichiro Itami (page 5794)

      Article first published online: 31 MAY 2011 | DOI: 10.1002/anie.201102691

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      “The biggest problem that scientists face is the efficient utilization of solar energy. If I won the lottery, I would buy as many sports cars of all kinds as possible …” This and more about Kenichiro Itami can be found on page 5794.

  7. Book Reviews

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Book Reviews
    9. Highlights
    10. Review
    11. Communications
    12. Preview
    1. Catalyzed Carbon[BOND]Heteroatom Bond Formation. Edited by Andrei K. Yudin. (page 5795)

      Cristina Nevado

      Article first published online: 25 MAY 2011 | DOI: 10.1002/anie.201101412

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      Wiley-VCH, Weinheim 2010. 506 pp., hardcover, € 149.00.—ISBN 978-3527324286

    2. Image and Reality. Kekulé, Kopp, and the Scientific Imagination. Von Alan J. Rocke. (pages 5795–5796)

      Henning Hopf

      Article first published online: 15 JUN 2011 | DOI: 10.1002/anie.201101723

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      The University of Chicago Press, Chicago 2010. 416 pp., hardcover, 45.00 €.—ISBN 978-0226723327

  8. Highlights

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Book Reviews
    9. Highlights
    10. Review
    11. Communications
    12. Preview
    1. Iron Catalysis

      Well-Defined Bifunctional Iron Catalysts for the Hydrogenation of Ketones: Iron, the New Ruthenium (pages 5798–5800)

      Gerald Bauer and Prof. Dr. Karl A. Kirchner

      Article first published online: 3 MAY 2011 | DOI: 10.1002/anie.201101579

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      Two functions are important: Three examples of well-defined bifunctional iron catalysts that are very efficient in the hydrogenation of ketones are described (see scheme). These remarkable studies will contribute significantly to the development of more environmentally friendly and sustainable reduction reactions in the near future.

    2. Chromatin Disruptors

      Disrupting the Reader of Histone Language (pages 5801–5803)

      Samuel S. Oliver and Prof. John M. Denu

      Article first published online: 25 MAY 2011 | DOI: 10.1002/anie.201101414

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      New targets, new drugs: In the context of regulating gene expression, small molecules have been found that specifically disrupt the interaction between the “reader” (e.g. a protein with a bromodomain) and chromatin. These results provide compelling proof-of-concept that disrupting histone readers is a viable strategy for the development of epigenetic drugs. (The picture shows the complex formed by (+)-JQ1 and the bromodomain hBRD2.)

    3. Polymer Design

      One is Enough: Influencing Polymer Properties with a Single Chromophoric Unit (pages 5804–5806)

      Dr. Patrick Theato

      Article first published online: 25 MAY 2011 | DOI: 10.1002/anie.201100975

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      Worth one's while: The careful use of a single chromophore on methodically designed polymers can be sufficient to modify polymer properties. Recent examples range from controlled micelle destruction and light-controlled precipitation in aqueous solution to the fabrication of nanoporous thin films (see schematic illustration of the use of a photocleavable block copolymer as a template for a nanoporous thin film).

  9. Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Book Reviews
    9. Highlights
    10. Review
    11. Communications
    12. Preview
    1. Upconversion

      Upconverting Nanoparticles (pages 5808–5829)

      Prof. Dr. Markus Haase and Dr. Helmut Schäfer

      Article first published online: 30 MAY 2011 | DOI: 10.1002/anie.201005159

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      Long becomes short: During upconversion (UC), absorption of several long-wavelength photons leads to emission of short-wavelength radiation. Current methods allow the synthesis of highly efficient, small UC particles with narrow size distribution able to form transparent solutions in a wide range of solvents (see photo of UC luminescence in nanocrystal solutions), and new synthetic routes are available to tune important properties of UC nanocrystals.

  10. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Book Reviews
    9. Highlights
    10. Review
    11. Communications
    12. Preview
    1. Hydrogenation

      A Uniform Bimetallic Rhodium/Iron Nanoparticle Catalyst for the Hydrogenation of Olefins and Nitroarenes (pages 5830–5833)

      Ikuse Nakamula, Dr. Yoshinori Yamanoi, Dr. Takane Imaoka, Prof. Kimihisa Yamamoto and Prof. Hiroshi Nishihara

      Article first published online: 1 JUN 2011 | DOI: 10.1002/anie.201102836

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      Mix and more than match: Relative to the catalytic activity of pure Rh nanoparticles in a dendrimer cage, Rh/Fe bimetallic nanoparticles in dendrimers have improved catalytic activity towards the hydrogenation of olefins, and unlike Wilkinson catalyst could catalyze nitroarene hydrogenation (see scheme, G4=4th generation dendrimer).

    2. Asymmetric Catalysis

      Catalytic Asymmetric Conjugate Addition/Oxidative Dearomatization Towards Multifunctional Spirocyclic Compounds (pages 5834–5838)

      Dr. Alena Rudolph, Pieter H. Bos, Auke Meetsma, Prof. Dr. Adriaan J. Minnaard and Prof. Dr. Ben L. Feringa

      Article first published online: 12 MAY 2011 | DOI: 10.1002/anie.201102069

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      Naphthol compounds bearing a pendant α,β-unsaturated ester undergo a copper(I)-catalyzed asymmetric conjugate addition/copper(II)-mediated intramolecular oxidative coupling to afford benzofused spirocyclic cyclohexenones (see scheme). This one-pot strategy results in two new carbon–carbon bonds and three contiguous stereocenters. The products contain a high degree of functionality and molecular complexity.

    3. Metabolic Exchange

      Connecting Chemotypes and Phenotypes of Cultured Marine Microbial Assemblages by Imaging Mass Spectrometry (pages 5839–5842)

      Dr. Yu-Liang Yang, Dr. Yuquan Xu, Roland D. Kersten, Wei-Ting Liu, Michael J. Meehan, Prof. Dr. Bradley S. Moore, Prof. Dr. Nuno Bandeira and Prof. Dr. Pieter C. Dorrestein

      Article first published online: 13 MAY 2011 | DOI: 10.1002/anie.201101225

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      Deciphering the language of bacteria: Imaging mass spectrometry (IMS) of a marine environmental sample revealed that a secreted peptide from an immobile Promicromonosporaceae strain alters the mobility of a motile Bacillus subtilis strain. The Promicromonosporaceae also respond to B. subtilis by producing hydroxamate siderophores. Thus, multifaceted and multifunctional metabolic exchange between microbes can be captured by IMS (see picture).

    4. Peptide Structures

      Characteristic Structural Parameters for the γ-Peptide 14-Helix: Importance of Subunit Preorganization (pages 5843–5846)

      Dr. Li Guo, Weicheng Zhang, Andrew G. Reidenbach, Michael W. Giuliano, Dr. Ilia A. Guzei, Lara C. Spencer and Prof. Samuel H. Gellman

      Article first published online: 12 MAY 2011 | DOI: 10.1002/anie.201101301

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      All wound up: Crystallographic data for a set of homologous peptides constructed from gabapentin and two to six preorganized γ-amino acid residues (see crystal structure of the longest peptide) allow derivation of characteristic parameters for the γ-peptide 14-helix and establish guidelines for characterizing 14-helical folding. The results suggest that the substitution pattern of a γ-residue has a profound effect on the propensity for 14-helical folding.

    5. Multiferroics

      Electric Control of Magnetization and Interplay between Orbital Ordering and Ferroelectricity in a Multiferroic Metal–Organic Framework (pages 5847–5850)

      Dr. Alessandro Stroppa, Dr. Prashant Jain, Dr. Paolo Barone, Dr. Martijn Marsman, Prof. Juan Manuel Perez-Mato, Prof. Anthony K. Cheetham, Prof. Harold W. Kroto and Dr. Silvia Picozzi

      Article first published online: 25 MAY 2011 | DOI: 10.1002/anie.201101405

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      Forget me not: In a new multiferroic metal–organic framework (see structure, Cu green, O red, C black, N blue, H gray; arrows show spin configuration), Jahn–Teller and antiferro-distortions induce a switchable ferroelectric polarization, which is coupled to a weak ferromagnetic component. This true magnetoelectric multiferroic should be very attractive for advanced memory devices.

    6. Heterobimetallic Block Copolymers

      Main-Chain Heterobimetallic Block Copolymers: Synthesis and Self-Assembly of Polyferrocenylsilane-b-Poly(cobaltoceniumethylene) (pages 5851–5855)

      Dr. Joe B. Gilroy, Dr. Sanjib K. Patra, Dr. John M. Mitchels, Prof. Mitchell A. Winnik and Prof. Ian Manners

      Article first published online: 26 MAY 2011 | DOI: 10.1002/anie.201008184

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      Two metals are better than one: Main-chain heterometallic block copolymers composed of iron- and cobalt-rich blocks (see picture) were synthesized through consecutive photocontrolled ring-opening polymerization (ROP) of sila[1]ferrocenophanes and dicarba[2]cobaltocenophanes followed by oxidation of the cobaltocene-containing block. The redox properties and self-assembly of the resulting block copolymers in solution were also studied.

    7. Self-Organized Hybrid Materials

      Photoimaging of Self-Organized CaCO3/Polymer Hybrid Films by Formation of Regular Relief and Flat Surface Morphologies (pages 5856–5859)

      Dr. Takeshi Sakamoto, Yosuke Nishimura, Dr. Tatsuya Nishimura and Prof. Dr. Takashi Kato

      Article first published online: 12 MAY 2011 | DOI: 10.1002/anie.201008191

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      Picture this! A photoimage written in a reactive polymer with UV light is transferred into CaCO3 crystal morphologies (see picture). The CaCO3 crystal films with microscopic regular relief structures and flat surfaces are self-organized on the nonirradiated and UV-irradiated areas of the polymer matrix, respectively.

    8. Quantum Dots

      Chirality of Glutathione Surface Coating Affects the Cytotoxicity of Quantum Dots (pages 5860–5864)

      Yiye Li, Yunlong Zhou, Hai-Yan Wang, Prof. Sarah Perrett, Prof. Yuliang Zhao, Prof. Zhiyong Tang and Prof. Guangjun Nie

      Article first published online: 12 MAY 2011 | DOI: 10.1002/anie.201008206

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      Choose your poison: Chiral CdTe quantum dots (QDs) coated with L- or D-glutathione (GSH) stabilizers exhibit differences in cytotoxicity although they have identical composition and size. D-GSH-QDs are less cytotoxic than L-GSH-QDs. The ability of QDs to induce cell death is correlated with their ability to induce autophagy, which is chirality-dependent (see picture).

    9. Nanostructures

      Encapsulation of Nanoparticles in Block Copolymer Micellar Aggregates by Directed Supramolecular Assembly (pages 5865–5868)

      Weikun Li, Shanqin Liu, Renhua Deng and Prof. Jintao Zhu

      Article first published online: 10 MAY 2011 | DOI: 10.1002/anie.201008224

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      Worm holes: Cylindrical or wormlike block copolymer micelles with gold nanoparticles encapsulated in a micellar core were fabricated through directed supramolecular assembly. This versatile approach allows fine-tuning of interparticle spacing and micellar morphology by varying the content of the nanoparticles or hydrogen bonding agent in the supramolecular assemblies.

    10. Asymmetric Synthesis

      Enantioselective Base-Free Electrophilic Amination of Benzofuran-2(3H)-ones: Catalysis by Binol-Derived P-Spiro Quaternary Phosphonium Salts (pages 5869–5872)

      Chuan-Le Zhu, Fa-Guang Zhang, Wei Meng, Jing Nie, Dr. Dominique Cahard and Prof. Jun-An Ma

      Article first published online: 10 MAY 2011 | DOI: 10.1002/anie.201100283

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      Aspiroing reactivity: A series of novel binol-derived P-spiro quaternary phosphonium salts were designed, prepared, and used for the first highly enantioselective amination of benzofuranones (see scheme; binol=1,1′-2-binaphthol, Bn=benzyl). An unprecedented mechanism involving the π–π interactions between the substrate and the catalyst was proposed as the primary binding mode on the basis of molecular modelling and DFT calculations.

    11. Bacterial Detection

      Sensitive and Selective Bacterial Detection Using Tetracysteine-Tagged Phages in Conjunction with Biarsenical Dye (pages 5873–5877)

      Dr. Lina Wu, Tingting Huang, Lingling Yang, Jianbo Pan, Shaobin Zhu and Prof. Dr. Xiaomei Yan

      Article first published online: 10 MAY 2011 | DOI: 10.1002/anie.201100334

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      A host-specific phage is genetically modified to tag a tetracysteine (TC) residue to its capsid protein. Upon bacterial infection, the TC tag is expressed on the surface of progeny virions and stained by membrane-permeant biarsenical dye, which results in fluorescence enhancement (see picture). The labeled bacteria are detectable by flow cytometry and fluorescence microscopy.

    12. Synthetic Methods

      Tandem Ring Opening/Cyclization of Vinylcyclopropanes: A Facile Synthesis of Chiral Bicyclic Amidines (pages 5878–5881)

      Venkataraman Ganesh, Dr. Devarajulu Sureshkumar and Prof. Srinivasan Chandrasekaran

      Article first published online: 10 MAY 2011 | DOI: 10.1002/anie.201100375

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      An open and shut case: An interesting bromine-catalyzed tandem ring opening/cyclization reaction of bicyclic vinylcyclopropanes with chloramine-T ([TsNCl]Na) has been demonstrated to furnish chiral bicyclic amidine derivatives in good yield. A plausible mechanism has been proposed based on the experimental observations. Ts=p-toluenesulfonyl.

    13. Huge Polymer Circles

      Synthesis and Direct Imaging of Ultrahigh Molecular Weight Cyclic Brush Polymers (pages 5882–5885)

      Dr. Yan Xia, Dr. Andrew J. Boydston and Prof. Robert H. Grubbs

      Article first published online: 17 MAY 2011 | DOI: 10.1002/anie.201101860

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      Convenient route to cyclic polymers: Ultrahigh molecular weight cyclic brush polymers were synthesized through ring-expansion metathesis polymerization of various macromonomers. Atomic force microscopy was used to visualize toroidal shapes and large opening pores, along with linear chains, which may result from high sensitivity of brush polymers to mechanical degradation.

    14. Hypergolicity

      Green Bipropellants: Hydrogen-Rich Ionic Liquids that Are Hypergolic with Hydrogen Peroxide (pages 5886–5888)

      Dr. Stefan Schneider, Dr. Tom Hawkins, Dr. Yonis Ahmed, Michael Rosander, Leslie Hudgens and Dr. Jeff Mills

      Article first published online: 12 MAY 2011 | DOI: 10.1002/anie.201101752

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      Lift-off: The low vapor toxicity of ionic liquids (ILs) make them attractive replacements for hydrazine in rocket fuel. However, ILs will fail to fulfill their revolutionary promise unless toxic oxidizers such as HNO3 or N2O4 can be replaced with safer alternatives such as H2O2. The ILs presented here are hypergolic with H2O2 (see picture) and are hydrogen-rich, thus helping to boost performance.

    15. Antibiotics

      The Natural Product Cyclomarin Kills Mycobacterium Tuberculosis by Targeting the ClpC1 Subunit of the Caseinolytic Protease (pages 5889–5891)

      Dr. Esther K. Schmitt, Meliana Riwanto, Dr. Vasan Sambandamurthy, Dr. Silvio Roggo, Charlotte Miault, Christian Zwingelstein, Dr. Philipp Krastel, Dr. Christian Noble, Dr. David Beer, Srinivasa P. S. Rao, Melvin Au, Pornwaratt Niyomrattanakit, Viviam Lim, Dr. Jun Zheng, Dr. Douglas Jeffery, Dr. Kevin Pethe and Dr. Luis R. Camacho

      Article first published online: 11 MAY 2011 | DOI: 10.1002/anie.201101740

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      Target practice: The target of the antibiotic cyclomarin A was identified in Mycobacterium. Cyclomarin A (see structure) binds the regulatory subunit of the Clp protease complex with high affinity resulting in elevated proteolysis and cell death. The property of cyclomarin to kill both growing and nonreplicating mycobacteria makes the Clp protease a promising target for antitubercular drug discovery.

    16. Natural Product Synthesis

      Synthesis of (−)-Okilactomycin by a Prins-Type Fragment-Assembly Strategy (pages 5892–5895)

      Dr. Jason M. Tenenbaum, William J. Morris, Daniel W. Custar and Prof. Dr. Karl A. Scheidt

      Article first published online: 10 MAY 2011 | DOI: 10.1002/anie.201102037

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      All things converge: A highly convergent synthesis of (−)-okilactomycin utilizes a Prins-type Maitland–Japp cyclization for the fragment assembly of two complex intermediates (see scheme). The synthesis also employs a highly diastereoselective Lewis acid promoted Diels–Alder reaction and an olefin ring-closing metathesis to close a strained 11-membered macrocycle.

    17. Synthetic Methods

      Nickel-Catalyzed Three-Component Coupling between Aryl Aldehydes, Norbornenes, and Silanes Leading to Indanols through Aromatic C[BOND]H Bond Activation of Aryl Aldehydes (pages 5896–5899)

      Dr. Kenichi Ogata, Yuka Atsuumi, Daisuke Shimada and Prof. Dr. Shin-ichi Fukuzawa

      Article first published online: 13 MAY 2011 | DOI: 10.1002/anie.201101468

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      The first example of the title reaction involving the combination of an aryl aldehyde, norbornene, and silane has been developed (see scheme). The reaction involves aromatic C[BOND]H bond activation of an aryl aldehyde at the ortho position, it proceeded with good diastereoselectively, and is applicable for various aryl aldehydes and norbornenes or norbornadienes. cod=cycloocta-l,5-diene, THF=tetrahydrofuran, NHC=N-heterocyclic carbene.

    18. Zeolites

      Evidence for F/SiO Anion Exchange in the Framework of As-Synthesized All-Silica Zeolites (pages 5900–5903)

      Dr. Xiaolong Liu, Dr. Ugo Ravon and Dr. Alain Tuel

      Article first published online: 12 MAY 2011 | DOI: 10.1002/anie.201101237

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      Not everything changes: Charge-compensating anions can be exchanged in as-synthesized zeolite frameworks with changes in both the density of defect sites and of the hydrophobic character of the zeolite. The reversible transformation occurs without dissolution/recrystallization of the zeolite and preserves the size and shape of the crystals (see picture). Fluoride removal is not possible in all-silica D4R units, for which fluoride ions play a structure-directing role.

    19. Li–S Battery

      Porous Hollow Carbon@Sulfur Composites for High-Power Lithium–Sulfur Batteries (pages 5904–5908)

      N. Jayaprakash, J. Shen, Surya S. Moganty, A. Corona and Prof. Lynden A. Archer

      Article first published online: 17 MAY 2011 | DOI: 10.1002/anie.201100637

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      Slowing down the shuttle: C@S nanocomposites (see TEM images) based on mesoporous, hollow carbon capsules were generated by a template-based approach. As the cathode material in a Li–S secondary battery, they display outstanding electrochemical features attributed to sequestration of elemental sulfur in the carbon capsules and to its favorable effect in limiting polysulfide shuttling as well as to enhanced electron transport from the sulfur.

    20. Endofullerenes

      Covalently Linked Porphyrin–La@C82 Hybrids: Structural Elucidation and Investigation of Intramolecular Interactions (pages 5909–5912)

      Dr. Lai Feng, Dr. Zdenek Slanina, Dr. Satoru Sato, Dr. Kenji Yoza, Dr. Takahiro Tsuchiya, Dr. Naomi Mizorogi, Prof. Dr. Takeshi Akasaka, Prof. Dr. Shigeru Nagase, Prof. Dr. Nazario Martín and Prof. Dr. Dirk M. Guldi

      Article first published online: 12 MAY 2011 | DOI: 10.1002/anie.201100432

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      ππ talks: Three isomeric porphyrin–La@C82 hybrids were synthesized and structurally characterized for the first time (see picture: La blue sphere, N dark blue, O red). The two chromophores, which have a large π surface, evidently exhibit electronic interactions in the ground state and communicate with each other in the photoexcited state.

    21. Extraction Methods

      Graphene and Graphene Oxide Sheets Supported on Silica as Versatile and High-Performance Adsorbents for Solid-Phase Extraction (pages 5913–5917)

      Dr. Qian Liu, Dr. Jianbo Shi, Jianteng Sun, Dr. Thanh Wang, Dr. Lixi Zeng and Prof. Dr. Guibin Jiang

      Article first published online: 12 MAY 2011 | DOI: 10.1002/anie.201007138

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      On the GO: Graphene (G) and graphene oxide (GO) supported on silica are demonstrated to be excellent adsorbents for reversed-phase and normal-phase solid-phase extraction (RP- and NP-SPE) towards various analytes ranging from small molecules to proteins and peptides. Notably, G-bound silica is capable of extracting proteins with large molecular weight and phosphorylated peptides, making it particularly suitable for MALDI-TOF mass spectrometry.

    22. C[BOND]H Activation

      Direct Palladium-Catalyzed Intermolecular Allylation of Highly Electron-Deficient Polyfluoroarenes (pages 5918–5923)

      Shilu Fan, Fei Chen and Prof. Dr. Xingang Zhang

      Article first published online: 17 MAY 2011 | DOI: 10.1002/anie.201008174

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      A simple operation: The use of readily available PPh3, high reaction efficiency, and good stereo- and regioselectivity provided useful and operationally simple access to polyfluoroarylated derivatives through the title transformation (see scheme; phen=1,10-phenanthroline). The reaction mechanism was also studied.

    23. Cyclic Amines

      Palladium-Catalyzed Ring-Contraction and Ring-Expansion Reactions of Cyclic Allyl Amines (pages 5924–5926)

      Igor Dubovyk, Dmitry Pichugin and Prof. Dr. Andrei K. Yudin

      Article first published online: 12 MAY 2011 | DOI: 10.1002/anie.201100612

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      Ring around the rosy: An amino group can act as the leaving group or the nucleophile in a palladium-catalyzed allylic amination. As a result, readily accessible cyclic amines can be either ring contracted or ring expanded (see scheme).

    24. Synthetic Methods

      Synthesis of Isoquinolines from α-Aryl Vinyl Azides and Internal Alkynes by Rh–Cu Bimetallic Cooperation (pages 5927–5931)

      Yi-Feng Wang, Kah Kah Toh, Jian-Yuan Lee and Dr. Shunsuke Chiba

      Article first published online: 17 MAY 2011 | DOI: 10.1002/anie.201101009

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      Catalysts in a relay: A synthetic method for delivering highly substituted isoquinolines has been developed (see scheme; Cp*=C5Me5, DMF=N,N-dimethylformamide, TEMPO=2,2,6,6-tetramethylpiperidine-1-oxyl). A preliminary mechanistic study showed that the rhodium and copper cooperate synergistically in the multistep sequence.

    25. Rhodium Catalysis

      Rhodium-Catalyzed Cycloisomerization Involving Cyclopropenes: Efficient Stereoselective Synthesis of Medium-Sized Heterocyclic Scaffolds (pages 5932–5937)

      Frédéric Miege, Dr. Christophe Meyer and Prof. Dr. Janine Cossy

      Article first published online: 12 MAY 2011 | DOI: 10.1002/anie.201101220

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      A happy medium: The title reaction of cyclopropenyl carbinols and carbinylamines gives carbo- and heterocycles with a [6.1.0] bicyclic ring fused to an aromatic ring (see scheme, Alloc=allyloxycarbonyl, Boc=tert-butyloxycarbonyl). These reactions are the first examples of the formation of medium-sized rings by the intramolecular cyclopropanation of an alkene with a donor-substituted rhodium carbenoid, which is not generated from a diazo compound.

    26. Scaffold Diversity

      Sequential Transformations to Access Polycyclic Chemotypes: Asymmetric Crotylation and Metal Carbenoid Reactions (pages 5938–5942)

      Jie Wu, Dr. Jorge Becerril, Yajing Lian, Prof. Dr. Huw M. L. Davies, Prof. Dr. John A. Porco Jr. and Prof. Dr. James S. Panek

      Article first published online: 10 MAY 2011 | DOI: 10.1002/anie.201101366

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      All in order: Bicyclic and tricyclic chemotypes were accessed through the title transformations. By subsequent pairing of installed functional groups using Heck cyclization or [2+2] photocycloaddition, the synthesis of tetracycles, pentacycles, and condensed polycycles has been achieved with high stereochemical and skeletal variation.

    27. Flow Chemistry

      Suzuki–Miyaura Cross-Coupling Reactions in Flow: Multistep Synthesis Enabled by a Microfluidic Extraction (pages 5943–5946)

      Dr. Timothy Noël, Dr. Simon Kuhn, Andrew J. Musacchio, Prof. Dr. Klavs F. Jensen and Prof. Dr. Stephen L. Buchwald

      Article first published online: 17 MAY 2011 | DOI: 10.1002/anie.201101480

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      Continuous success: A continuous-flow Suzuki–Miyaura cross-coupling reaction starting from phenols was made possible through use of an efficient microfluidic extraction operation and a packed-bed reactor. Various biaryls were obtained in excellent yield (14 examples). TBAB=Bu4N+Br.

    28. Colloidal Spheres

      Extension of The Stöber Method to the Preparation of Monodisperse Resorcinol–Formaldehyde Resin Polymer and Carbon Spheres (pages 5947–5951)

      Dr. Jian Liu, Prof. Shi Zhang Qiao, Dr. Hao Liu, Dr. Jun Chen, Ajay Orpe, Prof. Dongyuan Zhao and Prof. Gao Qing (Max) Lu

      Article first published online: 31 MAY 2011 | DOI: 10.1002/anie.201102011

      Thumbnail image of graphical abstract

      Sphere we go: Monodisperse resorcinol formaldehyde (RF) resin polymer spheres with finely tunable particle size ranging from 200 to 1000 nm (see pictures) are prepared by an extension of the Stöber method. Pyrolysis of the RF spheres at 600 °C under N2 atmosphere yields uniform carbon spheres with a volume shrinkage of 19 %.

    29. Microreactors

      Continuous In Situ Generation, Separation, and Reaction of Diazomethane in a Dual-Channel Microreactor (pages 5952–5955)

      Dr. Ram Awatar Maurya, Dr. Chan Pil Park, Jang Han Lee and Prof. Dr. Dong-Pyo Kim

      Article first published online: 25 MAY 2011 | DOI: 10.1002/anie.201101977

      Thumbnail image of graphical abstract

      A fierce dog: A method for the continuous in-situ on-demand generation, separation, and reaction of diazomethane in a dual-channel microreactor has been developed (see picture; Diazald=N-methyl-N-nitroso-p-toluenesulfonamide). The microchemical system allows a variety of diazomethane reactions to be performed without the most common problems of preparation, handling, transfer, and decomposition.

    30. Amyloids

      The Amyloid–Congo Red Interface at Atomic Resolution (pages 5956–5960)

      Anne K. Schütz, Alice Soragni, Dr. Simone Hornemann, Prof. Adriano Aguzzi, Dr. Matthias Ernst, Dr. Anja Böckmann and Prof. Beat H. Meier

      Article first published online: 17 MAY 2011 | DOI: 10.1002/anie.201008276

      Thumbnail image of graphical abstract

      The analytical “gold standard” for amyloid characterization and diagnostics, Congo red, was studied in complex with an amyloid (see picture). Based on details of the binding mode, a point mutation of the amyloid was prepared which has the same three-dimensional structure as the wild-type protein but is not congophilic. This surprising specificity may aid in the design of selective anti-amyloidogenic drugs.

    31. Polyoxometalates

      A Planar {Mn19(OH)12}26+ Unit Incorporated in a 60-Tungsto-6-Silicate Polyanion (pages 5961–5964)

      Dr. Bassem S. Bassil, Masooma Ibrahim, Rami Al-Oweini, Marie Asano, Zhenxing Wang, Dr. Johan van Tol, Prof. Naresh S. Dalal, Prof. Kwang-Yong Choi, Rosa Ngo Biboum, Dr. Bineta Keita, Prof. Louis Nadjo and Prof. Ulrich Kortz

      Article first published online: 17 MAY 2011 | DOI: 10.1002/anie.201007617

      Thumbnail image of graphical abstract

      Manganese in large numbers: The largest number of manganese ions ever incorporated in a polyoxometalate (POM) is found in a planar Mn19-oxo-hydroxo magnetic cluster incorporated in a discrete 60-tungsto-6-silicate (see structure Mn yellow, O red/pink). The compound has interesting structural, magnetic, and electrochemical properties.

    32. CS2 Activation

      C[BOND]C Bond Formation through Reductive Coupling of CS2 to Yield Uranium Tetrathiooxalate and Ethylenetetrathiolate Complexes (pages 5965–5968)

      Dr. Oanh P. Lam, Dr. Frank W. Heinemann and Prof. Dr. Karsten Meyer

      Article first published online: 10 MAY 2011 | DOI: 10.1002/anie.201101185

      Thumbnail image of graphical abstract

      A novel twist: The UIII complex [((AdArO)3N)U] reacts with CS2 by reductive coupling to form the tetrathiooxalate complex [{((AdArO)3N)U}2(μ-κ22-C2S4)] with a newly formed C[BOND]C bond (see scheme). The UIV/UIV tetrathiooxalate complex features a nonplanar C2S42− unit in an unprecedented μ-κ22 binding mode. Further reduction gives the ethylenetetrathiolate complex [Na(dme)3]2[{((AdArO)3N)U}2(μ-C2S4)]. DME=1,2-dimethoxyethane.

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      Preview: Angew. Chem. Int. Ed. 27/2011 (page 5971)

      Article first published online: 15 JUN 2011 | DOI: 10.1002/anie.201190052

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