Angewandte Chemie International Edition

Cover image for Vol. 52 Issue 31

July 29, 2013

Volume 52, Issue 31

Pages 7889–8168

  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. Book Review
    10. Correspondence
    11. Highlights
    12. Review
    13. Communications
    1. You have free access to this content
      Cover Picture: Hole–Shell Microparticles from Controllably Evolved Double Emulsions (Angew. Chem. Int. Ed. 31/2013) (page 7889)

      Dr. Wei Wang, Mao-Jie Zhang, Dr. Rui Xie, Dr. Xiao-Jie Ju, Chao Yang, Chuan-Lin Mou, Prof. David A. Weitz and Prof. Liang-Yin Chu

      Article first published online: 21 JUN 2013 | DOI: 10.1002/anie.201304863

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      Hole–shell microparticles with controllable structures and flexible internal surfaces have been fabricated from controllably evolved water/oil/water emulsions, as described by L.-Y. Chu et al. in their Communication on page 8084 ff. These microparticles could be used as microcontainers for controlled capture/release and as microreactors for confined reactions.

    2. You have free access to this content
      Inside Cover: Domino Reaction Catalyzed by Zeolites with Brønsted and Lewis Acid Sites for the Production of γ-Valerolactone from Furfural (Angew. Chem. Int. Ed. 31/2013) (page 7890)

      Linh Bui, Helen Luo, William R. Gunther and Prof. Yuriy Román-Leshkov

      Article first published online: 19 JUL 2013 | DOI: 10.1002/anie.201305564

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      The selective conversion of furfural into γ-valerolactone (GVL) through a series of domino-like reactions catalyzed by zeolites with Lewis and Brønsted acid sites is described by Y. Román-Leshkov and co-workers in their Communication on page 8022 ff. Zr-Beta and Al-MFI nanosheets generated GVL in 78 % yield without the use of high-pressure molecular hydrogen or precious metals.

    3. You have free access to this content
      Inside Back Cover: Engineering Multimodal Localized Surface Plasmon Resonances in Silicon Nanowires (Angew. Chem. Int. Ed. 31/2013) (page 8169)

      Dr. Li-Wei Chou and Prof. Michael A. Filler

      Article first published online: 21 JUN 2013 | DOI: 10.1002/anie.201304865

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      Localized surface plasmon resonances are generated in doped silicon nanowires by the absorption of mid-infrared light. In their Communication on page 8079 ff., M. A Filler and L.-W. Chou report a method to incorporate multiple, axially aligned, doped regions along the length of individual silicon nanowires. Their approach promises new opportunities to use the world's most ubiquitous semiconductor for catalysis, molecular detection, and energy harvesting.

    4. You have free access to this content
      Back Cover: Electrochemical Synthesis of One-Dimensional Mesoporous Pt Nanorods Using the Assembly of Surfactant Micelles in Confined Space (Angew. Chem. Int. Ed. 31/2013) (page 8170)

      Dr. Cuiling Li, Prof. Dr. Takaaki Sato and Prof. Dr. Yusuke Yamauchi

      Article first published online: 15 JUL 2013 | DOI: 10.1002/anie.201304258

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      Self-supported platinum nanorods with a high density of mesopores are prepared by electrochemical assembly of platinum-containing micelles in the pores of a polycarbonate membrane. In their Communication on page 8050 ff., Y. Yamauchi et al. show that superior tolerance towards carbon monoxide can be realized in the oxidation reaction of methanol by using the platinum nanorods as electrocatalysts.

  2. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Flashback
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Correspondence
    11. Highlights
    12. Review
    13. Communications
    1. Graphical Abstract: Angew. Chem. Int. Ed. 31/2013 (pages 7893–7909)

      Article first published online: 23 JUL 2013 | DOI: 10.1002/anie.201390031

  3. Flashback

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Flashback
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Correspondence
    11. Highlights
    12. Review
    13. Communications
    1. 50 Years Ago ... (page 7906)

      Article first published online: 23 JUL 2013 | DOI: 10.1002/anie.201305265

      Angewandte Chemie International Edition was first published in 1962, the mother journal first in 1888. In this monthly flashback, we feature some of the articles that appeared 50 years ago. This look back can open our eyes, stimulate discussion, or even raise a smile.

  4. Corrigendum

    1. Top of page
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    3. Graphical Abstract
    4. Flashback
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Correspondence
    11. Highlights
    12. Review
    13. Communications
    1. You have free access to this content
      Corrigendum: Notoamides A–D: Prenylated Indole Alkaloids Isolated from a Marine-Derived Fungus, Aspergillus sp. (page 7909)

      Hikaru Kato, Takushi Yoshida, Takanori Tokue, Yuka Nojiri, Hiroshi Hirota, Tomihisa Ohta, Robert M. Williams and Sachiko Tsukamoto

      Article first published online: 23 JUL 2013 | DOI: 10.1002/anie.201305232

      This article corrects:

      Notoamides A–D: Prenylated Indole Alkaloids Isolated from a Marine-Derived Fungus, Aspergillus sp.

      Vol. 46, Issue 13, 2254–2256, Article first published online: 16 FEB 2007

  5. News

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Flashback
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Correspondence
    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. Book Review
    10. Correspondence
    11. Highlights
    12. Review
    13. Communications
    1. Tomás Torres (page 7914)

      Article first published online: 12 MAR 2013 | DOI: 10.1002/anie.201300418

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      “When I was eighteen I wanted to be a football player for Real Madrid. If I could be described as an animal it would be a fighting bull …” This and more about Tomás Torres can be found on page 7914.

  7. News

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

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Flashback
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Correspondence
    11. Highlights
    12. Review
    13. Communications
    1. Life's Ratchet. How Molecular Machines Extract Order from Chaos. By Peter M. Hoffmann. (page 7917)

      Francesco Zerbetto

      Article first published online: 2 JUL 2013 | DOI: 10.1002/anie.201304031

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      Basic Books, New York, 2012. 278 pp., hardcover, $ 27.99.—ISBN 978-0465022533

  9. Correspondence

    1. Top of page
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    3. Graphical Abstract
    4. Flashback
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Correspondence
    11. Highlights
    12. Review
    13. Communications
    1. Microwaves in Synthesis

      Correspondence on Microwave Effects in Organic Synthesis (pages 7918–7923)

      Prof. Dr. Gregory B. Dudley, Prof. Dr. Albert E. Stiegman and Michael R. Rosana

      Article first published online: 3 JUL 2013 | DOI: 10.1002/anie.201301539

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      They're real. Microwave effects in organic synthesis remain controversial, but there is no longer any room for doubt that they exist. The question of whether the organic synthesis community should try to harness microwave effects strategically is the focus of this Correspondence.

    2. Reply to the Correspondence on Microwave Effects in Organic Synthesis (pages 7924–7928)

      Prof. Dr. C. Oliver Kappe

      Article first published online: 3 JUL 2013 | DOI: 10.1002/anie.201304368

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      Selective heating or superheating? The enhancement effects seen by Dudley and co-workers in the microwave-heated Friedel–Crafts alkylation (see graphic) are due to superheating of the bulk reaction mixture and not selective reactant heating. This argument forms the basis of this Correspondence.

  10. Highlights

    1. Top of page
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    3. Graphical Abstract
    4. Flashback
    5. Corrigendum
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    7. Author Profile
    8. News
    9. Book Review
    10. Correspondence
    11. Highlights
    12. Review
    13. Communications
    1. Flexible Carbon Materials

      Design of Three-Dimensional Porous Carbon Materials: From Static to Dynamic Skeletons (pages 7930–7932)

      Prof. An-Hui Lu, Dr. Guang-Ping Hao and Qiang Sun

      Article first published online: 3 JUL 2013 | DOI: 10.1002/anie.201302369

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      A new generation of three-dimensional carbon nanostructures is evolving. These flexible carbon systems based on carbon nanotubes and nanofibers and graphene sheets are capable of substantial shape deformation and thus have exciting applications in flexible electronics, sensors, and complex mechanical structures.

    2. Porous Single Crystals

      Fast Electron Transport and High Surface Area: Potential Application of Porous Anatase Single Crystals in Solar Cells (pages 7933–7935)

      Seulgi So and Prof. Dr. Patrik Schmuki

      Article first published online: 2 JUL 2013 | DOI: 10.1002/anie.201303849

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      A remarkable approach to the production of large mesoporous anatase single crystals was reported recently by Snaith et al. These crystals display two properties—high surface area and high electron mobility—that fundamentally affect the performance of any TiO2-based photoelectrochemical device, such as Grätzel-type dye-sensitized solar cells.

  11. Review

    1. Top of page
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    4. Flashback
    5. Corrigendum
    6. News
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    9. Book Review
    10. Correspondence
    11. Highlights
    12. Review
    13. Communications
    1. Medicinal Chemistry

      Schistosomiasis Chemotherapy (pages 7936–7956)

      Dr. Sophie A.-L. Thétiot-Laurent, Dr. Jérôme Boissier, Dr. Anne Robert and Prof. Dr. Bernard Meunier

      Article first published online: 27 JUN 2013 | DOI: 10.1002/anie.201208390

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      Bilharziasis (schistosomiasis) is the second most prevalent parasitic disease in Africa after malaria. The therapeutic arsenal against this disease is currently limited to a single drug, praziquantel, which has been used for 35 years. It is thus urgent to develop new antischistosomal drugs for efficient bi- or tri-therapies in combination with praziquantel.

  12. Communications

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

      Enantiopure Water-Soluble [Fe4L6] Cages: Host–Guest Chemistry and Catalytic Activity (pages 7958–7962)

      Dr. Jeanne L. Bolliger, Dr. Ana M. Belenguer and Dr. Jonathan R. Nitschke

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201302136

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      Inside information: The new enantiopure cage molecule ΔΔΔΔ-Fe4L6 (and its enantiomer, ΛΛΛΛ-Fe4L6) was prepared by subcomponent self-assembly. It binds a range of organic guests (A, see scheme) in its cavity and distinguishes between the enantiomers of a chiral organic guest. Host ΔΔΔΔ-Fe4L6 is also a catalyst for the hydrolysis (giving B and C) of the neurotoxic organophosphate dichlorvos.

    2. Gold Catalysis

      Highly Active Mononuclear NAC–Gold(I) Catalysts (pages 7963–7966)

      M. Sc. Maria Camila Blanco Jaimes, Dipl.-Chem. Constantin R. N. Böhling, Dr. Juan Manuel Serrano-Becerra and Prof. Dr. A. Stephen K. Hashmi

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201210351

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      One gold is enough: Mononuclear, homogeneous gold catalysts displayed excellent catalytic activity on the order of that previously reported for gold nanoparticle catalysts and surface-bound gold complexes. In the model synthesis of spiro compounds (see picture) extremely high turnover numbers were achieved with only 0.000001 mol % of a silsesquioxane-substituted catalyst.

    3. Catalyst Design

      Noncovalent Interactions in Organocatalysis: Modulating Conformational Diversity and Reactivity in the MacMillan Catalyst (pages 7967–7971)

      Mareike C. Holland, Shyeni Paul, Dr.  W. Bernd Schweizer, Dr. Klaus Bergander, Dr. Christian Mück-Lichtenfeld, Dr. Sami Lakhdar, Prof. Dr. Herbert Mayr and Prof. Dr. Ryan Gilmour

      Article first published online: 21 JUN 2013 | DOI: 10.1002/anie.201301864

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      Intriguing imidazolidinones! Inspired by noncovalent interactions in proteins, a series of electronically distinct MacMillan catalysts were designed. The effect of electronic modulation on ground state conformation, reactivity, and performance was studied in a catalytic setting with intriguing outcomes.

    4. Trifluoromethylation

      Sandmeyer Trifluoromethylation of Arenediazonium Tetrafluoroborates (pages 7972–7975)

      Dr. Grégory Danoun, Bilguun Bayarmagnai, Matthias F. Grünberg and Prof. Dr. Lukas J. Gooßen

      Article first published online: 5 JUL 2013 | DOI: 10.1002/anie.201304276

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      Copper capabilities: Diazonium salts are converted into the corresponding trifluoromethyl derivatives in the presence of a trifluoromethyl–copper complex generated in situ from CuSCN and the inexpensive, easy-to-use trifluoromethylating reagent Me3Si-CF3 (see scheme). This Sandmeyer-type reaction allows the straightforward synthesis of trifluoromethylated arenes and heteroarenes from the corresponding amines.

    5. Reversible H2 Activation

      Reversible Dihydrogen Activation in Cationic Rare-Earth-Metal Polyhydride Complexes (pages 7976–7980)

      Waldemar Fegler, Dr. Ajay Venugopal, Dr. Thomas P. Spaniol, Prof. Dr. Laurent Maron and Prof. Dr. Jun Okuda

      Article first published online: 21 JUN 2013 | DOI: 10.1002/anie.201303958

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      In or out? A quadruply hydride-bridged dilutetium complex releases dihydrogen under C[BOND]H bond activation of one of the methyl groups of the ligand. The resulting trihydrido complex readily takes up dihydrogen (see scheme).

    6. Small Molecules

      The Iminyl Radical O2SN (pages 7981–7984)

      Prof. Dr. Xiaoqing Zeng, Dr. Helmut Beckers and Prof. Dr. Helge Willner

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201302968

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      The novel iminyl radical O2SN, a SO3 analogue, was produced by flash vacuum pyrolysis of gaseous alkyl sulfonyl azides RSO2N3 (R=CF3, CH3) mixed with argon. Photoisomerization (λ>360 nm) of O2SN into planar syn-OSNO and anti-OSNO (see picture) was observed in solid noble-gas matrices.

    7. C[BOND]H Functionalization

      Metal-Free Radical Azidoarylation of Alkenes: Rapid Access to Oxindoles by Cascade C[BOND]N and C[BOND]C Bond-Forming Reactions (pages 7985–7989)

      Dr. Kiran Matcha, Dr. Rishikesh Narayan and Dr. Andrey P. Antonchick

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201303550

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      A novel method for the oxidative radical azidation of alkenes relies on an azide in combination with a hypervalent iodine reagent. A cascade of C[BOND]N and C[BOND]C bond-forming reactions yields 2-oxindoles under metal-free conditions with high reaction rates at ambient temperature and provides access to complex products (see scheme; TMS=trimethylsilyl).

    8. Alkaloid Synthesis

      Bio-Inspired Dimerization Reaction of Tryptophan Derivatives in Aqueous Acidic Media: Three-Step Syntheses of (+)-WIN 64821, (−)-Ditryptophenaline, and (+)-Naseseazine B (pages 7990–7994)

      Shinji Tadano, Yuri Mukaeda and Prof. Dr. Hayato Ishikawa

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201303143

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      Doubling up: The direct bio-inspired dimerization of commercially available amine-free tryptophan derivatives in aqueous acidic media provides C2-symmetrical and nonsymmetrical dimeric compounds. Further processing completes the concise syntheses of naturally occurring dimeric diketopiperazine alkaloids such as (+)-WIN 64821 (see picture) in overall yields of up to 20 %.

    9. Asymmetric Catalysis

      Formation of Quaternary Centers by Copper-Catalyzed Asymmetric Conjugate Addition of Alkylzirconium Reagents (pages 7995–7999)

      Dr. Mireia Sidera, Philippe M. C. Roth, Rebecca M. Maksymowicz and Dr. Stephen P. Fletcher

      Article first published online: 18 JUN 2013 | DOI: 10.1002/anie.201303202

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      Pure and simple: Alkylzirconocenes generated in situ from simple alkenes are used in highly enantioselective copper-catalyzed 1,4-addition reactions to trisubstituted cyclic enones to generate quaternary centers. These reactions operate at room temperature under a range of conditions and tolerate many functional groups. Cp=cyclopentadienyl, Tf=trifluoromethanesulfonyl.

    10. Prebiotic Photochemistry

      Photochemical Steps in the Prebiotic Synthesis of Purine Precursors from HCN (pages 8000–8003)

      Eliot Boulanger, Dr. Anakuthil Anoop, Dr. Dana Nachtigallova, Prof. Dr. Walter Thiel and Dr. Mario Barbatti

      Article first published online: 19 JUN 2013 | DOI: 10.1002/anie.201303246

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      So much excitement: The mechanism for the photoconversion of the HCN tetramer into a precursor of purine nucleobases and nucleotides has been revealed by computational methods. Dissipation of the photoenergy in less than 2 ps eliminates the possibility of hot-ground-state reactions. Instead, a series of photoexcitations followed by internal conversion (IC) drives the reaction via an excited azetene (see picture).

    11. Nanoparticles

      Electron-Beam-Induced Deposition of Bimetallic Nanostructures from Bulk Liquids (pages 8004–8007)

      Dr. Matthew Bresin, Adam Chamberlain, Dr. Eugenii U. Donev, Dr. Chandan B. Samantaray, Gregory S. Schardien and Prof. Dr. J. Todd Hastings

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201303740

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      Bimetallic deposits: Liquid-phase electron-beam-induced deposition is shown to result in bimetallic deposits with predictable final compositions. The compositions were predicted by the first-order rates of the reaction between solvated electrons and metal ionic complexes. AuAg and AuPt nanoparticles are shown with diameters typically less than 100 nm and high purity.

    12. Asymmetric Catalysis

      Asymmetric Ion Pair Catalysis of 6π Electrocyclizations: Brønsted Acid Catalyzed Enantioselective Synthesis of Optically Active 1,4-Dihydropyridazines (pages 8008–8011)

      Arindam Das, Chandra M. R. Volla, Iuliana Atodiresei, Wolfgang Bettray and Magnus Rueping

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201301638

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      Electric slide: Described is a general, operationally simple, highly enantioselective Brønsted acid catalyzed condensation/6π-electrocyclization reaction between hydrazones and α,β-unsaturated aldehydes that yields valuable 1,4-dihydropyridazines. The reaction exhibits high tolerance towards functional groups and affords products with up to 98 % ee.

    13. Thioglycoside Synthesis

      Umpolung Reactivity in the Stereoselective Synthesis of S-Linked 2-Deoxyglycosides (pages 8012–8016)

      Kedar N. Baryal, Danyang Zhu, Dr. Xiaohua Li and Prof. Dr. Jianglong Zhu

      Article first published online: 18 JUN 2013 | DOI: 10.1002/anie.201301682

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      Take control! An unprecedented sulfenylation of stereochemically defined 2-deoxyglycosyl lithium species with asymmetric sugar-derived disulfide acceptors enabled the stereoselective synthesis of both α- and β-S-linked 2-deoxyoligosaccharides. Reductive lithiation of 2-deoxyglycosyl phenylsulfides at −78 °C provides predominantly axial glycosyl lithium species, which upon warming isomerize to predominantly equatorial lithium species (see scheme).

    14. Carborate Anions

      Copper-Mediated C[BOND]C Cross-Coupling Reaction of Monocarba-closo-dodecaborate Anion for the Synthesis of Functional Molecules (pages 8017–8021)

      Junichiro Kanazawa, Prof. Dr. Ryo Takita, Dr. Aleksandra Jankowiak, Prof. Dr. Shinya Fujii, Prof. Dr. Hiroyuki Kagechika, Prof. Dr. Daisuke Hashizume, Prof. Dr. Koichi Shudo, Prof. Dr. Piotr Kaszyński and Prof. Dr. Masanobu Uchiyama

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201302448

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      New couple: A cross-coupling reaction at the carbon vertex of a monocarba-closo-dodecaborate has been developed to allow efficient introduction of various aryl groups and other sp2/sp-hybridized carbon centers. A copper(I) complex facilitated the coupling process with a wide range of electrophiles at room temperature. The reaction was used to prepare a series of C-arylated carborane anion derivatives (see picture; B green, C blue), some of which showed androgen-receptor binding activity and also mesogenic properties.

    15. Biomass Conversion

      Domino Reaction Catalyzed by Zeolites with Brønsted and Lewis Acid Sites for the Production of γ-Valerolactone from Furfural (pages 8022–8025)

      Linh Bui, Helen Luo, William R. Gunther and Prof. Yuriy Román-Leshkov

      Article first published online: 11 JUN 2013 | DOI: 10.1002/anie.201302575

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      Take the straight path: Furfural was converted into γ-valerolactone (GVL) through sequential transfer-hydrogenation and hydrolysis reactions catalyzed by zeolites with Lewis and Brønsted acid sites (see picture). Together, Zr-Beta and Al-MFI nanosheets generated GVL in 78 % yield without the use of precious metals or molecular H2. This system offers an attractive streamlined strategy for the production of GVL from biomass-derived molecules.

    16. Cumulenes

      Ambivalent Reactivity Modes of β-Chlorovinyl Ketones: Electrophilic Lithium [3]Cumulenolates from Soft Vinyl Enolization Strategy (pages 8026–8030)

      Dr. Hun Young Kim, Edward Oscar Rooney, Raymond Phillip Meury and Prof. Dr. Kyungsoo Oh

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201302750

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      Soft spot: The soft vinyl enolization of (E)-β-chlorovinyl ketones results in the in situ generation of electrophilic lithium [3]cumulenolates, which react with nucleophiles such as another lithium [3]cumulenolate to stereoselectively form vinyl allenones. They can also react with ketimine esters to give 3-methylenepyrrolidines.

    17. Catalytic Amination

      Direct C[BOND]H Amination of Arenes with Alkyl Azides under Rhodium Catalysis (pages 8031–8036)

      Kwangmin Shin, Yunjung Baek and Prof. Dr. Sukbok Chang

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201302784

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      New horizons in the utility of azides: The rhodium-catalyzed intermolecular direct C[BOND]H amination of arenes with alkyl azides provides a convenient route to N-alkyl anilines (see scheme; DG=directing group). Alkyl azides with a wide range of functional groups reacted readily with various substrates, including benzamides, aromatic ketones, and flavones.

    18. Sulfur Tetrafluoride

      The Solid-State Structure of SF4: The Final Piece of the Puzzle (pages 8037–8040)

      James T. Goettel, Nathan Kostiuk and Prof. Dr. Michael Gerken

      Article first published online: 19 JUN 2013 | DOI: 10.1002/anie.201302917

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      Solved at last: The crystal structure of solid SF4, which has a melting point of −121 °C, has been obtained. It exhibits weak intermolecular S⋅⋅⋅F interactions. A similar structural motif was observed within a layer of SF4 in [HNC5H3(CH3)2+]2F⋅⋅⋅SF4[SF5]⋅3 SF4. The latter structure contains a range of bonding modes between S and F, namely SF5, F4S⋅⋅⋅F, F4S⋅⋅⋅FSF4, and F4S⋅⋅⋅FSF3.

    19. Neurochemistry

      Heme Binding Induces Dimerization and Nitration of Truncated β-Amyloid Peptide Aβ16 Under Oxidative Stress (pages 8041–8044)

      Dr. Grégory Thiabaud, Dr. Silvia Pizzocaro, Dr. Ricardo Garcia-Serres, Prof. Jean-Marc Latour, Prof. Enrico Monzani and Prof. Luigi Casella

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201302989

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      Stressful situation: Ferric heme binds to Aβ16 giving a mixture of five-coordinate [hemin(Aβ16)] and six-coordinate [hemin(Aβ16)2] species, the equilibrium of which depends on the Aβ16/hemin ratio and on temperature. Under oxidative and nitrative stress conditions the heme–Aβ16 complexes promote peroxidase-like reactions causing oxidation and nitration of the Aβ Tyr10 residue. Both dityrosine formation and tyrosine nitration strongly enhance Aβ aggregation.

    20. Iron-Catalyzed Reduction

      Selective Reduction of Esters to Aldehydes under the Catalysis of Well-Defined NHC–Iron Complexes (pages 8045–8049)

      Haoquan Li, Dr. Luis C. Misal Castro, Jianxia Zheng, Dr. Thierry Roisnel, Dr. Vincent Dorcet, Dr. Jean-Baptiste Sortais and Prof. Dr. Christophe Darcel

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201303003

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      On a direct course to the aldehyde: Hydrosilylation catalyzed by a well-defined N-heterocyclic-carbene–iron complex under UV irradiation enabled the selective reduction of esters to aldehydes (see scheme; Bn=benzyl, Mes=mesityl). The low catalyst loading and very mild reaction conditions make this chemoselective transformation a promising alternative to the reduction of esters with diisobutylaluminum hydride.

    21. Electrocatalysis

      Electrochemical Synthesis of One-Dimensional Mesoporous Pt Nanorods Using the Assembly of Surfactant Micelles in Confined Space (pages 8050–8053)

      Dr. Cuiling Li, Prof. Dr. Takaaki Sato and Prof. Dr. Yusuke Yamauchi

      Article first published online: 26 JUN 2013 | DOI: 10.1002/anie.201303035

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      Platinum nanorods: A general way to synthesize novel self-supported one-dimensional mesoporous Pt nanorods with a high density of mesopores by electrochemical assembly of micelles in the pores of a polycarbonate (PC; see picture) membrane is reported. The obtained 1D motifs show high activity and tolerance towards CO in the methanol oxidation reaction and exhibit superior electrochemical activity in the oxygen reduction reaction.

    22. Structure Elucidation

      Boracyclophanes: Modulation of the σ/π Character in Boron–Benzene Interactions (pages 8054–8058)

      Tomokatsu Kushida and Prof. Dr. Shigehiro Yamaguchi

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201303830

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      Character sketch: Boracyclophanes, in which the benzene ring coordinates to the boron atom, were synthesized. X-ray crystallographic analysis and theoretical calculations revealed the intrinsic character of the boron–benzene interaction. Its σ/π character can be modulated by changing the electron-donating character of the benzene ring.

    23. Ubiquitination

      Convergent Chemical Synthesis of Histone H2B Protein for the Site-Specific Ubiquitination at Lys34 (pages 8059–8063)

      Peter Siman, Dr. Subramanian Vedhanarayanan Karthikeyan, Dr. Miroslav Nikolov, Dr. Wolfgang Fischle and Prof. Ashraf Brik

      Article first published online: 21 JUN 2013 | DOI: 10.1002/anie.201303844

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      As You Like It: The convergent chemical synthesis of the histone H2B protein was achieved. This approach enabled the attachment of ubiquitin at Lys34 (see picture) and should make it possible to synthesize H2B with any other posttranslational modification in demand.

    24. Carbonylation

      Domino Catalysis: Palladium-Catalyzed Carbonylation of Allylic Alcohols to β,γ-Unsaturated Esters (pages 8064–8068)

      Dr. Qiang Liu, Lipeng Wu, Dr. Haijun Jiao, Xianjie Fang, Dr. Ralf Jackstell and Prof. Dr. Matthias Beller

      Article first published online: 21 JUN 2013 | DOI: 10.1002/anie.201303850

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      Make it green: The Pd-catalyzed carbonylation of allylic alcohols with aliphatic alcohols represents a cost-effective, salt-free, and atom-economic carbonylation process generating water as the sole by-product. Mechanistic studies uncovered a new domino C[BOND]O coupling/carbonylation reaction pathway.

    25. Drug Synthesis

      Concise Synthesis and Antimalarial Activity of All Four Mefloquine Stereoisomers Using a Highly Enantioselective Catalytic Borylative Alkene Isomerization (pages 8069–8073)

      Jinyue Ding and Prof. Dr. Dennis G. Hall

      Article first published online: 1 JUL 2013 | DOI: 10.1002/anie.201303931

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      The pluses and minuses of mefloquine: A highly enantioselective catalytic borylative isomerization/aldehyde allylboration method for the stereoselective synthesis of the antimalarial drug mefloquine was optimized, thus leading to an efficient synthesis of all four mefloquine stereoisomers and analogues (see scheme). The absolute configuration of these potent compounds was determined for the first time by using chemical synthesis.

    26. Imaging Agents

      Multi-Chromatic pH-Activatable 19F-MRI Nanoprobes with Binary ON/OFF pH Transitions and Chemical-Shift Barcodes (pages 8074–8078)

      Dr. Xiaonan Huang, Dr. Gang Huang, Dr. Shanrong Zhang, Dr. Koji Sagiyama, Dr. Osamu Togao, Dr. Xinpeng Ma, Dr. Yiguang Wang, Yang Li, Dr. Todd C. Soesbe, Dr. Baran D. Sumer, Prof. Masaya Takahashi, Prof. A. Dean Sherry and Prof. Jinming Gao

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201301135

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      Imaging all the people: Using ionizable diblock copolymers a series of nanoprobes encoded with different 19F reporters for specific pH transitions is prepared for use in MRI. The pH response of the nanoprobes is extremely sharp (ΔpHON/OFF≈0.25 pH), and results from the disassembly of polymer micelles (see scheme). A collection of three nanoprobes provides the proof of concept and allows for a qualitative measurement of environmental pH values.

    27. Semiconductor Plasmonics

      Engineering Multimodal Localized Surface Plasmon Resonances in Silicon Nanowires (pages 8079–8083)

      Dr. Li-Wei Chou and Prof. Michael A. Filler

      Article first published online: 13 JUN 2013 | DOI: 10.1002/anie.201301468

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      Multimodal plasmonic resonances: Silicon nanowires that contain multiple, dimensionally controlled, axially registered doped regions were synthesized and investigated by angle-dependent mid-infrared spectroscopy (see picture; P=partial pressure). The wires support mid-infrared multimodal localized surface plasmon resonances.

    28. Microfabrication

      Hole–Shell Microparticles from Controllably Evolved Double Emulsions (pages 8084–8087)

      Dr. Wei Wang, Mao-Jie Zhang, Dr. Rui Xie, Dr. Xiao-Jie Ju, Chao Yang, Chuan-Lin Mou, Prof. David A. Weitz and Prof. Liang-Yin Chu

      Article first published online: 10 JUN 2013 | DOI: 10.1002/anie.201301590

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      Hole in one! Hole–shell microparticles (blue, see picture) with controllable structures and flexible internal surfaces have been fabricated from W/O/W emulsions. These microparticles could be used as microcontainers for the controlled capture/release of molecules, microsphere classification/separation, confined cell culture, or as microreactors for catalysis.

    29. Ferroelectricity

      Ferroelectricity Driven by Twisting of Silicate Tetrahedral Chains (pages 8088–8092)

      Prof. Hiroki Taniguchi, Dr. Akihide Kuwabara, Dr. Jungeun Kim, Younghun Kim, Dr. Hiroki Moriwake, Prof. Sungwng Kim, Takuya Hoshiyama, Tsukasa Koyama, Prof. Shigeo Mori, Prof. Masaki Takata, Prof. Hideo Hosono, Prof. Yoshiyuki Inaguma and Prof. Mitsuru Itoh

      Article first published online: 14 JUN 2013 | DOI: 10.1002/anie.201302188

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      A lead-free ferroelectric: The occurrence of ferroelectricity is demonstrated in a silicate-based compound (Bi2SiO5, see picture), by direct observation of polarization switching. The mechanism of ferroelectricity in Bi2SiO5 has been studied by Raman scattering, transmission electron microscopy, X-ray powder diffraction, and first-principles calculations. The observed ferroelectricity stems from twisting of the one-dimensional SiO4 tetrahedral chain.

    30. Radical Reactions

      Chemoselective Oxidation by Electronically Tuned Nitroxyl Radical Catalysts (pages 8093–8097)

      Shohei Hamada, Dr. Takumi Furuta, Yoshiyuki Wada and Prof. Dr. Takeo Kawabata

      Article first published online: 21 JUN 2013 | DOI: 10.1002/anie.201302261

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      Electronic tuning: Nitroxyl radical 1 is shown to be an efficient catalyst for the oxidation of secondary alcohols, and promotes oxidation through an oxoammonium species which is highly reactive because of the adjacent electron-withdrawing ester groups. Chemoselective oxidation of benzylic alcohols in the presence of aliphatic alcohols is observed and is proposed to proceed by a rate-determining hydride transfer.

    31. Protein Delivery

      Two-Step Protein Self-Assembly in the Extracellular Matrix (pages 8098–8101)

      Won Min Park and Prof. Julie A. Champion

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201302331

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      Carrier-free protein delivery: Protein self-assembly can be conducted in the extracellular matrix (ECM) where engineered protein components (ZR-ELP) form particles that become entrapped, bind a model protein (mCherry-ZE), and dissociate. Spontaneous diffusion–coacervation and high-affinity binding of proteins mediate in situ formation of the self-assembled particles that shrink and release the model protein in the ECM (see scheme).

    32. Phosphor Materials

      Nanosegregation and Neighbor-Cation Control of Photoluminescence in Carbidonitridosilicate Phosphors (pages 8102–8106)

      Wan-Yu Huang, Fumitaka Yoshimura, Dr. Kyota Ueda, Dr. Yasuo Shimomura, Dr. Hwo-Shuenn Sheu, Dr. Ting-Shan Chan, Heather F. Greer, Prof. Dr. Wuzong Zhou, Prof. Dr. Shu-Fen Hu, Prof. Dr. Ru-Shi Liu and Prof. Dr. J. Paul Attfield

      Article first published online: 21 JUN 2013 | DOI: 10.1002/anie.201302494

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      Blue, green, and yellow phosphors are obtained in the Sr1−xY0.98+xCe0.02Si4N7−xCx system (x=0→1). Decreases in thermal quenching barrier height with x result from a dominant neighboring-cation effect, through which the replacement of Sr2+ by Y3+ reduces the covalency of Ce[BOND]N bonding. Green emission is observed from a cation-segregated nanostructure of SrYSi4N7 and Y2Si4N6C domains in x=0.2–0.6 samples.

    33. Electrochemistry

      Electrochemically Mediated Seawater Desalination (pages 8107–8110)

      Kyle N. Knust, Dr. Dzmitry Hlushkou, Dr. Robbyn K. Anand, Prof. Ulrich Tallarek and Prof. Richard M. Crooks

      Article first published online: 19 JUN 2013 | DOI: 10.1002/anie.201302577

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      Membraneless desalination: A simple power supply is used to apply a 3.0 V potential bias across a microelectrochemical cell comprising two microchannels spanned by a single bipolar electrode (BPE) to drive chloride oxidation and water electrolysis at the BPE poles. The resulting ion depletion zone and associated electric field gradient direct ions into a branching microchannel, consequently producing desalted water. Gnd=ground.

    34. Inversion of Chirality

      Solvent- and Achiral-Guest-Triggered Chiral Inversion in a Planar Chiral pseudo[1]Catenane (pages 8111–8115)

      Dr. Tomoki Ogoshi, Tomohiro Akutsu, Daiki Yamafuji, Takamichi Aoki and Prof. Dr. Tada-aki Yamagishi

      Article first published online: 21 JUN 2013 | DOI: 10.1002/anie.201302675

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      On the flipside: A planar chiral pseudo- [1]catenane based on pillar[5]arene, in which an alkyl chain is connected to one pillar[5]arene unit, has been synthesized. Capture and release of achiral guests and solvents trigger the inclusion and de-threading of the alkyl chain, which causes the inversion of planar chirality.

    35. MRI Contrast Agents

      Salicylic Acid and Analogues as diaCEST MRI Contrast Agents with Highly Shifted Exchangeable Proton Frequencies (pages 8116–8119)

      Xing Yang, Xiaolei Song, Yuguo Li, Prof. Guanshu Liu, Prof. Sangeeta Ray Banerjee, Prof. Martin G. Pomper and Prof. Michael T. McMahon

      Article first published online: 21 JUN 2013 | DOI: 10.1002/anie.201302764

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      More than water: Chemical exchange saturation transfer (CEST) contrast agents have used water bound to lanthanides as a source of highly shifted exchangeable proton frequencies. Compounds with the 2-hydroxybenzoic acid scaffold were investigated as a source of highly shifted protons for CEST MRI contrasting.

    36. Molecular Capsules

      Atroposelective Self-Assembly of a Molecular Capsule from Amphiphilic Anthracene Trimers (pages 8120–8123)

      Akira Suzuki, Kei Kondo, Prof. Dr. Munetaka Akita and Dr. Michito Yoshizawa

      Article first published online: 19 JUN 2013 | DOI: 10.1002/anie.201302789

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      Atroposelective formation: Selective formation of a molecular capsule was demonstrated from an amphiphilic cis-atropisomer bearing three anthracene rings and four sulfonate groups through hydrophobic and aromatic–aromatic interactions. The dimeric capsule binds small guest molecules; the resultant host–guest complexes exhibit ground-state charge-transfer interactions accompanied by changes in host emission.

    37. Fluorescent Probes

      Environment-Sensitive Fluorescent Turn-On Probes Targeting Hydrophobic Ligand-Binding Domains for Selective Protein Detection (pages 8124–8128)

      Yu-De Zhuang, Po-Yi Chiang, Chia-Wen Wang and Prof. Dr. Kui-Thong Tan

      Article first published online: 18 JUN 2013 | DOI: 10.1002/anie.201302884

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      Bind and shine: An approach for the selective detection of both enzymes and non-enzymatic proteins using an environment-sensitive fluorescent turn-on probe is described (see scheme). This approach targets the hydrophobic ligand-binding domain of the target protein to trigger the fluorescence turn-on and was shown to be specific for the targeted protein.

    38. Biosensors

      A Two-Channel Ratiometric Electrochemical Biosensor for In Vivo Monitoring of Copper Ions in a Rat Brain Using Gold Truncated Octahedral Microcages (pages 8129–8133)

      Dr. Xiaolan Chai, Xinguang Zhou, Anwei Zhu, Dr. Limin Zhang, Dr. Yao Qin, Prof. Guoyue Shi and Prof. Yang Tian

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201302958

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      Brain chemistry: A biosensor has been developed for in vivo determination of copper ions in a rat brain by using gold truncated octahedral microcages. The significant analytical performance of the present biosensor, as well as the properties of a carbon fiber microelectrode have provided a direct and reliable approach for monitoring cerebral metal ions (W.E.=working electrode; see picture).

    39. H2 Production

      Exceptional Poly(acrylic acid)-Based Artificial [FeFe]-Hydrogenases for Photocatalytic H2 Production in Water (pages 8134–8138)

      Feng Wang, Wen-Jing Liang, Jing-Xin Jian, Cheng-Bo Li, Dr. Bin Chen, Prof. Dr. Chen-Ho Tung and Prof. Dr. Li-Zhu Wu

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201303110

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      Light, polymer, action: A set of water-soluble poly(acrylic acid) catalysts PAA-g-Fe2S2 containing {Fe2S2}, an [FeFe]-hydrogenase active-site mimic, is synthesized. This system, combined with CdSe quantum dots and ascorbic acid, has an exceptional turnover number and initial turnover frequency (27 135 and 3.6 s−1) for the photocatalytic production of H2 in water, which is the highest efficiency to date for [FeFe]-hydrogenase mimics.

    40. Nucleic Acid Analogues

      Binary Genetic Cassettes for Selecting XNA-Templated DNA Synthesis In Vivo (pages 8139–8143)

      Dr. Valérie Pezo, Dr. Feng Wu Liu, Dr. Mikhail Abramov, Prof. Mathy Froeyen, Prof. Piet Herdewijn and Dr. Philippe Marlière

      Article first published online: 26 JUN 2013 | DOI: 10.1002/anie.201303288

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      Hereditary information, coded in two bases, can be conveyed to DNA in vivo in the form of cyclohexenyl nucleic acid (CeNA), arabinofuranosyl nucleic acid (AraNA), and hexitol nucleic acid (HNA) messages. It was thus demonstrated that a binary genetic cassette can be used for the title process.

    41. Bioinorganic Modeling

      Homolytic Cleavage of Fe[BOND]S Bonds in Rubredoxin under Mechanical Stress (pages 8144–8146)

      Dr. Guilherme M. Arantes, Dr. Anirban Bhattacharjee and Dr. Martin J. Field

      Article first published online: 18 JUN 2013 | DOI: 10.1002/anie.201303462

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      Spin is the thing: Iron–sulfur proteins of the rubredoxin family only have one Fe center coordinated by four cysteine residues (see picture, Fe orange). A multiscale modeling approach is used to see if Fe[BOND]S bond dissociation in these iron–sulfur clusters occurs by heterolytic fission or homolytic cleavage. As Fe complexes can have near-degenerate levels with different total spin, their spin states and spin crossovers must be characterized during the reaction.

    42. Catalytic Cyanation

      Hydrocyanative Cyclization and Three-Component Cross-Coupling Reaction between Allenes and Alkynes under Nickel Catalysis (pages 8147–8150)

      Prof. Shigeru Arai, Yuka Amako, Xiaofei Yang and Prof. Atsushi Nishida

      Article first published online: 21 JUN 2013 | DOI: 10.1002/anie.201303883

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      Packed with functionality: The key step in the title reactions with acetone cyanohydrin is a regioselective hydronickelation of allenes. Subsequent carbometalation of the alkyne followed by reductive elimination gave cyano-functionalized tetrasubstituted alkenes in a regio- and stereoselective manner (see scheme; EWG=electron-withdrawing group, Ts=p-toluenesulfonyl).

    43. Carbon Nanospheres

      Simple and Green Synthesis of Nitrogen-Doped Photoluminescent Carbonaceous Nanospheres for Bioimaging (pages 8151–8155)

      Wei Li, Zehui Zhang, Biao Kong, Shanshan Feng, Dr. Jinxiu Wang, Dr. Lingzhi Wang, Jianping Yang, Dr. Fan Zhang, Prof. Dr. Peiyi Wu and Prof. Dr. Dongyuan Zhao

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201303927

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      From silk to spheres: A large-scale synthesis of water-soluble nitrogen-doped polymer-like carbonaceous nanospheres with a uniform size of ca. 70 nm, through a simple and green hydrothermal process employing cocoon silk in water, has been developed. The resultant nanospheres show excellent photoluminescent properties, exhibit low toxicity, and are biocompatible for in vivo imaging.

    44. Enantioselective Catalysis

      Enantioselective Synthesis of Quaternary Carbon Stereogenic Centers through Copper-Catalyzed Conjugate Additions of Aryl- and Alkylaluminum Reagents to Acyclic Trisubstituted Enones (pages 8156–8159)

      Jennifer A. Dabrowski, Matthew T. Villaume and Prof. Amir H. Hoveyda

      Article first published online: 18 JUN 2013 | DOI: 10.1002/anie.201304035

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      Acyclic quaternary carbons by conjugate addition: The first examples of catalytic enantioselective conjugate additions of aryl and alkyl units that generate acyclic all-carbon quaternary stereogenic centers have been developed (see scheme). The requisite organoaluminum reagents can either be prepared in situ from easily available organolithiums or purchased at low cost.

    45. Magnetic Particles

      Fabrication and Assembly of Magneto-Responsive, Anisotropic, and Hybrid Microparticles of Variable Size and Shape (pages 8160–8164)

      Dr. Su Yeon Lee and Prof. Shu Yang

      Article first published online: 24 JUN 2013 | DOI: 10.1002/anie.201304183

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      Molded magnets: The co-assembly of silica colloids and iron oxide nanoparticles in a PDMS mold gives magnetic responsive microparticles. When dispersed in an aqueous solution (see picture), the microparticles could rotate and flip under the action of a magnetic field (1 kG). The particles could also be reversibly switched between aligned chain structures and a hexagonal array in both bulk solutions and in emulsion droplets.

    46. Synthetic Methods

      Generation of Organolithium Compounds bearing Super Silyl Ester and their Application to Matteson Rearrangement (pages 8165–8168)

      Susumu Oda and Prof. Dr. Hisashi Yamamoto

      Article first published online: 21 JUN 2013 | DOI: 10.1002/anie.201304225

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      It's super-silyl-fragilithyl-ester-aryl-docious: The super silyl group is a strong protecting group for carboxylic acids and provides a method for direct lithiation that is compatible with the ester moiety. Organolithium compounds bearing a super silyl ester react with a variety of electrophiles in high yields (see scheme). The reaction of lithiated super silyl chloroacetate with a boron compound gives α-functionalization of the ester moiety by Matteson rearrangement.

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