Angewandte Chemie International Edition

Cover image for Vol. 52 Issue 33

August 12, 2013

Volume 52, Issue 33

Pages 8475–8751

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    1. You have free access to this content
      Cover Picture: Total Synthesis and Structural Revision of Viridicatumtoxin B (Angew. Chem. Int. Ed. 33/2013) (page 8475)

      Prof. Dr.  K. C. Nicolaou, Dr. Christian Nilewski, Christopher R. H. Hale, Dr. Heraklidia A. Ioannidou, Dr. Abdelatif ElMarrouni and Lizanne G. Koch

      Article first published online: 23 JUL 2013 | DOI: 10.1002/anie.201305680

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      The potent and complex antibiotic viridicatumtoxin B is a member of the tetracycline family and exhibits impressive activity against a variety of Gram-positive bacterial strains, including methicillin-resistant Staphylococcus aureus (MRSA) and Enterococcus faecalis (shown in the background). In their Communication on page 8736 ff.,, K. C. Nicolaou et al. describe the total synthesis and structural revision of viridicatumtoxin B, thus paving the way for future molecular design, chemical syntheses, and biological investigations.

    2. You have free access to this content
      Inside Cover: Graphene Oxide Nanoribbons from the Oxidative Opening of Carbon Nanotubes Retain Electrochemically Active Metallic Impurities (Angew. Chem. Int. Ed. 33/2013) (page 8476)

      Colin Hong An Wong, Chun Kiang Chua, Bahareh Khezri, Richard D. Webster and Prof. Martin Pumera

      Article first published online: 26 JUN 2013 | DOI: 10.1002/anie.201304977

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      Metallic impurities influence the properties of graphene oxide prepared from carbon nanotubes. In their Communication on page 8685 ff., M. Pumera et al. show that the graphene oxide contains metallic impurities that survive the oxidative treatment of carbon nanotubes. Similar to metal-based impurities in sandstone, which give color to the displayed Antelope Canyon, these metallic impurities influence the properties of the resulting graphene oxide.

    3. You have free access to this content
      Inside Back Cover: Room-Temperature Ice Growth on Graphite Seeded by Nano-Graphene Oxide (Angew. Chem. Int. Ed. 33/2013) (page 8753)

      Dr. Yi Zheng, Dr. Chenliang Su, Dr. Jiong Lu and Prof. Kian Ping Loh

      Article first published online: 15 JUL 2013 | DOI: 10.1002/anie.201305678

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      A sprinkle of nano-sized graphene oxide flakes on graphite induces room-temperature ice growth on the substrate. In their Communication om page 8708 ff., K. P. Loh et al. capture the nucleation and growth processes, akin to Ostwald ripening, using noncontact atomic force microscopy. Ice with different morphologies, such as 1D row, anisotropic nanocrystal, and platelike, can be grown under ambient conditions. Such a hybrid nano graphene oxide-graphite template can be used as a model system to study crystal nucleation and growth in real time.

    4. You have free access to this content
      Back Cover: General Formation of Complex Tubular Nanostructures of Metal Oxides for the Oxygen Reduction Reaction and Lithium-Ion Batteries (Angew. Chem. Int. Ed. 33/2013) (page 8754)

      Dr. Genqiang Zhang, Dr. Bao Yu Xia, Chong Xiao, Le Yu, Prof. Xin Wang, Prof. Yi Xie and Prof. Xiong Wen (David) Lou

      Article first published online: 26 JUL 2013 | DOI: 10.1002/anie.201305981

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      Complex hollow tube-in-tube nanostructures have been fabricated for many metal oxides through a general strategy, as described by X. W. Lou, Y. Xie, et al. in their Communication on page 8643 ff. The method involves two simple steps: coating carbon nanofibers with a layer of metal glycolate and subsequent calcination in air. The unique complex tubular metal oxide structures are promising electrocatalysts for the oxygen reduction reaction and electrode materials for lithium ion batteries.

  2. Graphical Abstract

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

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    1. You have free access to this content
      Corrigendum: Enantioselective Construction of α-Quaternary Cyclobutanones by Catalytic Asymmetric Allylic Alkylation (page 8493)

      Corey M. Reeves, Christian Eidamshaus, Jimin Kim and Prof. Brian M. Stoltz

      Article first published online: 8 AUG 2013 | DOI: 10.1002/anie.201305706

      This article corrects:

      Enantioselective Construction of α-Quaternary Cyclobutanones by Catalytic Asymmetric Allylic Alkylation1

      Vol. 52, Issue 26, 6718–6721, Article first published online: 17 MAY 2013

  4. News

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

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    1. George A. Olah (page 8500)

      Article first published online: 8 APR 2013 | DOI: 10.1002/anie.201301116

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      “In a spare hour, I read outside chemistry. If I could be any age I would be young again. …” This and more about George A. Olah can be found on page 8500.

  6. Book Review

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    1. Chemical Technology. An Integral Textbook. By Andreas Jess and Peter Wasserscheid. (pages 8501–8502)

      Gadi Rothenberg

      Article first published online: 5 JUL 2013 | DOI: 10.1002/anie.201305324

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      Wiley-VCH, Weinheim, 2013. 950 pp., hardcover, € 79.90.—ISBN 978-3527304462

  7. Highlights

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

      Electron Tomography: Three-Dimensional Imaging of Real Crystal Structures at Atomic Resolution (pages 8504–8506)

      Dr. Bingsen Zhang and Prof. Dr. Dang Sheng Su

      Article first published online: 15 JUL 2013 | DOI: 10.1002/anie.201303804

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      No matter how you slice it: New insight into nanostructured materials is provided by a novel imaging technique, which reproduces the real three-dimensional (3D) fine structure of nanomaterials at the atomic level from two-dimensional (2D) projections (see scheme).

    2. Radical Enzymes

      Bacterial Methanogenesis Proceeds by a Radical Mechanism (pages 8507–8509)

      Prof. Dr. Wolfgang Buckel

      Article first published online: 12 JUL 2013 | DOI: 10.1002/anie.201304593

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      The thiyl radical of cysteine 272 (C272) in the C-P lyase adds to 5-phosphoribose-1-methylphosphonate to give a covalently bound thiophosphonate radical. Reaction with glycine 32 (G32) of the enzyme yields methane, a glycyl radical, and thiophosphate (see scheme). Intramolecular attack of the 2-OH group leads to 5-phosphoribose-1,2-cyclic-phosphate, whereas the glycyl radical oxidizes the liberated SH group back to the thiyl radical.

  8. Minireview

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

      Migratory Insertion of Alkenes into Metal–Oxygen and Metal–Nitrogen Bonds (pages 8510–8525)

      Dr. Patrick S. Hanley and Prof. John F. Hartwig

      Article first published online: 5 JUL 2013 | DOI: 10.1002/anie.201300134

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      In the middle of things: Recent work has shown that the insertions of unactivated alkenes into the metal–oxygen and metal–nitrogen bonds of metal alkoxo and metal amido complexes can occur as rapidly or more rapidly than insertions into metal–alkyl bonds. Studies on catalytic and stoichiometric reactions occurring through this increasingly common class of organometallic reactions are reviewed.

  9. Review

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    1. Oxygen Reduction Reaction

      Tuning Nanoparticle Catalysis for the Oxygen Reduction Reaction (pages 8526–8544)

      Dr. Shaojun Guo, Sen Zhang and Prof. Shouheng Sun

      Article first published online: 14 JUN 2013 | DOI: 10.1002/anie.201207186

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      Efforts in searching for efficient nanoparticle catalysts for the oxygen reduction reaction (ORR) in fuel cells have led to various nanoparticle (NP) systems with precise control of size, shape, composition, and structure. Whereas the traditional Pt-based catalysts are still under heavy investigation, recent studies have led to the emergence of non-Pt systems. This Review highlights the recent efforts in developing Pt- and non-Pt-based NPs into advanced nanocatalysts for the ORR.

  10. Communications

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

      Nickel/Nickel(II) Oxide Nanoparticles Anchored onto Cobalt(IV) Diselenide Nanobelts for the Electrochemical Production of Hydrogen (pages 8546–8550)

      Yun-Fei Xu, Dr. Min-Rui Gao, Ya-Rong Zheng, Dr. Jun Jiang and Prof. Dr. Shu-Hong Yu

      Article first published online: 10 JUL 2013 | DOI: 10.1002/anie.201303495

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      Not noble but effective: A novel Ni/NiO/CoSe2 hybrid material has been synthesized as an efficient catalyst for the hydrogen evolution reaction (HER; see picture). This new catalyst has a cathodic onset potential at −0.03 V, a Tafel slope of 39 mV per decade, and represents currently the best Pt-free electrocatalyst for the HER in acidic medium.

    2. Kinase Proteomics

      Design and Synthesis of Minimalist Terminal Alkyne-Containing Diazirine Photo-Crosslinkers and Their Incorporation into Kinase Inhibitors for Cell- and Tissue-Based Proteome Profiling (pages 8551–8556)

      Dr. Zhengqiu Li, Piliang Hao, Dr. Lin Li, Chelsea Y. J. Tan, Xiamin Cheng, Grace Y. J. Chen, Prof. Dr. Siu Kwan Sze, Prof. Dr. Han-Ming Shen and Prof. Dr. Shao Q. Yao

      Article first published online: 10 JUN 2013 | DOI: 10.1002/anie.201300683

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      Less is more: A minimalist “clickable” photo-crosslinker (see scheme) was incorporated with numerous small-molecule kinase inhibitors. The resulting probes were used for both in vitro (cell lysates) and in situ (live cells) proteome profiling, for large-scale identification of their potential cellular kinase targets and shows improved outcomes over previous probes.

    3. Fluorescent Probes

      Visualization and Isolation of Langerhans Islets by a Fluorescent Probe PiY (pages 8557–8560)

      Dr. Nam-Young Kang, Dr. Sung-Chan Lee, Dr. Sung-Jin Park, Prof. Hyung-Ho Ha, Dr. Seong-Wook Yun, Dr. Elena Kostromina, Dr. Natalia Gustavsson, Dr. Yusuf Ali, Yogeswari Chandran, Dr. Hang-Suk Chun, Dr. MyungAe Bae, Dr. Jin Hee Ahn, Dr. Weiping Han, Dr. George K. Radda and Prof. Young-Tae Chang

      Article first published online: 28 MAY 2013 | DOI: 10.1002/anie.201302149

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      Lighting up the pancreas: A pancreatic beta cell selective probe PiY (red, see picture) was developed which stains Langerhans islets in live animals without toxicity or side effects. Through tail-vein injection, PiY allowed for a comparison of the islets between healthy and diabetic mice. PiY also facilitated the isolation of healthy Langerhans islets by using a fluorescence-guided surgical procedure.

    4. Biradicaloids

      Tetracyanoquaterrylene and Tetracyanohexarylenequinodimethanes with Tunable Ground States and Strong Near-Infrared Absorption (pages 8561–8565)

      Dr. Zebing Zeng, Sangsu Lee, José L. Zafra, Dr. Masatoshi Ishida, Xiaojian Zhu, Zhe Sun, Yong Ni, Prof. Richard D. Webster, Prof. Run-Wei Li, Prof. Juan T. López Navarrete, Prof. Chunyan Chi, Prof. Jun Ding, Prof. Juan Casado, Prof. Dongho Kim and Prof. Jishan Wu

      Article first published online: 23 JUL 2013 | DOI: 10.1002/anie.201305348

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      Biradicaloids based on quinoidal rylenes! Soluble and stable tetracyanoquaterrylenequinodimethane (QR-CN) and tetracyanohexarylenequinodimethane (HR-CN) were synthesized. QR-CN has a closed-shell quinoidal structure in the ground state, whereas HR-CN has a singlet biradical ground state. Both compounds showed very strong one-photon and two-photon absorption in the NIR range.

    5. DNA Structures

      Structural Basis of DNA Quadruplex–Duplex Junction Formation (pages 8566–8569)

      Kah Wai Lim and Prof. Dr. Anh Tuân Phan

      Article first published online: 21 JUN 2013 | DOI: 10.1002/anie.201302995

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      Coaxial and orthogonal orientations of the helices (left and right illustration, respectively) in a quadruplex–duplex junction were realized by incorporating a duplex hairpin across the diverse geometries of a quadruplex. The modularity of the approach was validated through the simultaneous attachment of multiple duplex stems onto a G-quadruplex scaffold to generate a G-junction.

    6. Nano Stir Bars

      Stirring in Suspension: Nanometer-Sized Magnetic Stir Bars (pages 8570–8573)

      Wen Han Chong, Lip Ket Chin, Rachel Lee Siew Tan, Hong Wang, Prof. Ai Qun Liu and Prof. Hongyu Chen

      Article first published online: 13 JUN 2013 | DOI: 10.1002/anie.201303249

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      Stirred, not shaken: Single-line chains of 40 nm Fe3O4 nanoparticles can be used as the world's smallest magnetic stir bars. Their synthesis is facile and scalable. They can be introduced into picoliter emulsion droplets and turned effectively using a commercial magnetic stir plate. Because of their small size, they can resist sedimentation under gravitational and magnetic forces, thus allowing them to remain suspended and stir all parts of the solution.

    7. C[BOND]H Bond Functionalization

      Cobalt-Catalyzed Intramolecular Olefin Hydroarylation Leading to Dihydropyrroloindoles and Tetrahydropyridoindoles (pages 8574–8578)

      Zhenhua Ding and Prof. Naohiko Yoshikai

      Article first published online: 16 JUL 2013 | DOI: 10.1002/anie.201305151

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      Regiodivergent catalysis: Cobalt N-heterocyclic carbene (NHC) catalysts promote intramolecular olefin hydroarylation of indoles bearing an N-homoallyl or bis(homoallyl) tether and a C3 aldimine directing group to afford dihydropyrroloindoles and tetrahydropyridoindoles under mild conditions. The course of the cyclization is dependent on the tether, but can be controlled by the NHC ligand.

    8. Solar Water Splitting

      Ordered Macroporous BiVO4 Architectures with Controllable Dual Porosity for Efficient Solar Water Splitting (pages 8579–8583)

      Dr. Min Zhou, Hao Bin Wu, Jian Bao, Lin Liang, Prof. Xiong Wen (David) Lou and Prof. Yi Xie

      Article first published online: 14 JUN 2013 | DOI: 10.1002/anie.201302680

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      Holes in holes: By using a modified colloidal crystal templating method, periodically ordered macroporous architectures with controllable dual porosity are fabricated (see picture). Taking BiVO4 as an example, these unique structures provide a platform for a better understanding of the correlation between material geometrical features and charge migration for the photoelectrochemical water splitting process.

    9. Heterocycles

      Organocatalytic Synthesis of Highly Functionalized Pyridines at Room Temperature (pages 8584–8587)

      Dr. Zugui Shi and Prof. Dr. Teck-Peng Loh

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201301519

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      Amines by all means: A unique aza-Rauhut–Currier/cyclization/desulfonation cascade reaction between allenoates and N-sulfonyl-1-aza-1,3-dienes, catalyzed by the readily available diamine TMEDA, has been developed. This strategy provides facile access to a broad range of valuable highly functionalized pyridines in good yields under very mild reaction conditions.

    10. Organocatalysis

      Direct β-Activation of Saturated Aldehydes to Formal Michael Acceptors through Oxidative NHC Catalysis (pages 8588–8591)

      Junming Mo, Liang Shen and Prof. Dr. Yonggui Robin Chi

      Article first published online: 13 JUN 2013 | DOI: 10.1002/anie.201302152

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      Without detours: Oxidative catalysis mediated by N-heterocyclic carbenes (NHCs) enables the direct β-carbon functionalization of saturated aldehydes (see scheme). The reaction proceeds through two sequential oxidative steps to generate α,β-unsaturated triazolium ester equivalents as formal Michael acceptors, which react with 1,3-diketones and β-ketone esters in an enantioselective manner.

    11. Asymmetric Organocatalysis

      NHC Organocatalytic Formal LUMO Activation of α,β-Unsaturated Esters for Reaction with Enamides (pages 8592–8596)

      Dr. Jiajia Cheng, Zhijian Huang and Prof. Dr. Yonggui Robin Chi

      Article first published online: 10 JUL 2013 | DOI: 10.1002/anie.201303247

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      An effective wake-up call: Stable α,β-unsaturated esters were activated by the addition of a chiral N-heterocyclic carbene (NHC) organocatalyst, and the resulting reactive Michael acceptor intermediates reacted with enamide nucleophiles to furnish optically pure products (see scheme; Ts=p-toluenesulfonyl). These products can be converted readily into bioactive δ-lactams, piperidines, and their derivatives.

    12. Asymmetric Catalysis

      Catalytic, Enantioselective, and Highly Chemoselective Bromocyclization of Olefinic Dicarbonyl Compounds (pages 8597–8601)

      Yi Zhao, Dr. Xiaojian Jiang and Prof. Dr. Ying-Yeung Yeung

      Article first published online: 14 JUL 2013 | DOI: 10.1002/anie.201304107

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      Overriding preferences: An amine–thiocarbamate catalyst can mediate the facile, efficient, and highly enantioselective bromocyclization of olefinic 1,3-dicarbonyl compounds. In the presence of the bifunctional catalyst, the bromination occurs chemoselectively at the olefinic moiety rather than at the carbon atom in the α-position to the carbonyl units.

    13. Nanostructures

      Hierarchical Nanosheet-Based MoS2 Nanotubes Fabricated by an Anion-Exchange Reaction of MoO3–Amine Hybrid Nanowires (pages 8602–8606)

      Sifei Zhuo, You Xu, Weiwei Zhao, Jin Zhang and Prof. Dr. Bin Zhang

      Article first published online: 3 JUL 2013 | DOI: 10.1002/anie.201303480

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      Moving onward and outward: MoO3–ethylenediamine (EDA) inorganic–organic hybrid nanowires were successfully transformed into hierarchical nanosheet-based MoS2 nanotubes (HNN-MoS2) by anion exchange with S2− anions at elevated temperature (see picture). The resulting nanotubes were highly active catalysts for photoelectrochemical hydrogen evolution by water splitting.

    14. Organocatalysis

      N-Heterocyclic Carbene Catalyzed [4+3] Annulation of Enals and o-Quinone Methides: Highly Enantioselective Synthesis of Benzo-ε-Lactones (pages 8607–8610)

      Prof. Dr. Hui Lv, Wen-Qiang Jia, Li-Hui Sun and Prof. Dr. Song Ye

      Article first published online: 1 JUL 2013 | DOI: 10.1002/anie.201303903

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      Enantioselectivity through H bonding: An unprecedented [4+3] annulation of enals with o-quinone methides catalyzed by N-heterocyclic carbenes (NHCs) to give benzo-ε-lactones is described. High to excellent enantioselectivity was achieved by using a chiral triazolium NHC having a free OH group, which participates in a hydrogen-bonding interaction with the substrate.

    15. Carbonylation

      Palladium-Catalyzed Reductive Carbonylation of Aryl Halides with N-Formylsaccharin as a CO Source (pages 8611–8615)

      Dr. Tsuyoshi Ueda, Dr. Hideyuki Konishi and Prof. Dr. Kei Manabe

      Article first published online: 3 JUL 2013 | DOI: 10.1002/anie.201303926

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      Easy peasy: The title reaction employs N-formylsaccharin, which is an easily accessible crystalline compound, as an effective CO source. The reactions proceed with a small excess of the CO source at moderate temperatures and were successfully applied to a wide range of aryl bromides. DMF=N,N-dimethylformamide, dppb=1,4-bis-(diphenylphosphino)butane.

    16. Nazarov Reaction

      Organoaluminum-Mediated Interrupted Nazarov Reaction (pages 8616–8619)

      Yonghoon Kwon, Dr. Robert McDonald and Prof. Frederick G. West

      Article first published online: 3 JUL 2013 | DOI: 10.1002/anie.201303996

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      InternAl delivery: Organoaluminum reagents activate 1,4-dien-3-ones for Nazarov electrocyclization (see scheme), then transfer a substituent to the resulting cyclopentenyl cation with moderate to complete regioselectivity and diastereoselectivity.

    17. Drug Design

      Lysine-Specific Demethylase 1-Selective Inactivators: Protein-Targeted Drug Delivery Mechanism (pages 8620–8624)

      Daisuke Ogasawara, Dr. Yukihiro Itoh, Dr. Hiroki Tsumoto, Dr. Taeko Kakizawa, Dr. Koshiki Mino, Dr. Kiyoshi Fukuhara, Prof. Hidehiko Nakagawa, Dr. Makoto Hasegawa, Dr. Ryuzo Sasaki, Prof. Tamio Mizukami, Prof. Naoki Miyata and Prof. Takayoshi Suzuki

      Article first published online: 3 JUL 2013 | DOI: 10.1002/anie.201303999

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      Drug drop off: Given that lysine-specific demethylase 1 (LSD1) could be potently and selectively inactivated by delivering phenylcyclopropylamine (PCPA), a weak and nonselective LSD1 inhibitor, directly to the enzyme's active site, a novel series of LSD1 inactivators (1) were designed. Biological and mechanistic studies indicate that 1 inhibits LSD1 potently and selectively.

    18. Silyl Complexes

      Si[BOND]Si and Si[BOND]O Bond Activation at Platinum: Stepwise Formation of a SiH3 Complex (pages 8625–8628)

      Dipl.-Chem. Cathérine Mitzenheim and Prof. Dr. Thomas Braun

      Article first published online: 1 JUL 2013 | DOI: 10.1002/anie.201302459

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      The more, the better: Treatment of [Pt(H)2(dcpe)] (dcpe=1,2-bis(dicyclohexylphosphino)ethane) with stoichiometric amounts of silane leads to the bis(silyl) complex [Pt{Si(OMe)3}2(dcpe)], whereas the use of an excess silane results in hydrodealkoxylations by repetitive Si[BOND]O bond activation and the formation of SiH3 ligands (see scheme; Cy=cyclohexyl).

    19. Fluorostannylation

      Synchronous Ar[BOND]F and Ar[BOND]Sn Bond Formation through Fluorostannylation of Arynes (pages 8629–8632)

      Prof. Dr. Hiroto Yoshida, Ryuma Yoshida and Prof. Dr. Ken Takaki

      Article first published online: 2 JUL 2013 | DOI: 10.1002/anie.201302783

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      An aryne insertion into the F[BOND]Sn bond of tributyltin fluoride leads to the synchronous formation of Ar[BOND]F and Ar[BOND]Sn bonds to afford diverse 2-fluoroarylstannanes straightforwardly. The formal total synthesis of flurbiprofen by using a fluorostannylation product is also reported.

    20. 1,3-Dipolar Cycloaddition

      Organocatalytic Diastereo- and Enantioselective 1,3-Dipolar Cycloaddition of Azlactones and Methyleneindolinones (pages 8633–8637)

      Wangsheng Sun, Gongming Zhu, Chongyang Wu, Guofeng Li, Dr. Liang Hong and Prof. Dr. Rui Wang

      Article first published online: 1 JUL 2013 | DOI: 10.1002/anie.201302831

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      A simple route to complexity: An organocatalytic 1,3-dipolar cycloaddition between azlactones and methyleneindolinones provided spirooxindoles with high enantioselectivity (see scheme). This transformation takes advantage of the nucleophilic C4 and electrophilic C2 atoms in the azlactone substrate. Bn=benzyl, HOBt=1-hydroxy-1H-benzotriazole, MTBE=methyl tert-butyl ether, PG=protecting group, TMS=trimethylsilyl.

    21. C[BOND]C Coupling

      Phosphane-Functionalized Cycloheptatrienyl–Cyclopentadienyl Titanium Sandwich Complexes: Phosphorus Ligands with an Integrated Reducing Agent for Palladium(0) Catalyst Generation (pages 8638–8642)

      Dr. Alain C. Tagne Kuate, Dr. Soheila Sameni, Dr. Matthias Freytag, Prof. Dr. Peter G. Jones and Prof. Dr. Matthias Tamm

      Article first published online: 1 JUL 2013 | DOI: 10.1002/anie.201304252

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      A picture of (non)innocence: Non-innocent and bulky phosphanes bearing a reducing cycloheptatrienyl–cyclopentadienyl titanium moiety swiftly convert PdII into Pd0 species at room temperature (see scheme). The resulting complex catalyzes the Suzuki–Miyaura coupling with fast conversion even of sterically hindered aryl bromides.

    22. Hollow Nanostructures

      General Formation of Complex Tubular Nanostructures of Metal Oxides for the Oxygen Reduction Reaction and Lithium-Ion Batteries (pages 8643–8647)

      Dr. Genqiang Zhang, Dr. Bao Yu Xia, Chong Xiao, Le Yu, Prof. Xin Wang, Prof. Yi Xie and Prof. Xiong Wen (David) Lou

      Article first published online: 4 JUL 2013 | DOI: 10.1002/anie.201304355

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      Tube in a tube: A general strategy for the fabrication of novel complex tube-in-tube nanostructures for many metal oxides has been developed. The method involves coating carbon nanofibers with a layer of metal glycolate followed by calcination in air. The unique complex tubular structures of metal oxides are shown to exhibit promising properties for the title applications.

    23. Natural Products Synthesis

      Total Synthesis of Vinigrol (pages 8648–8651)

      Qingliang Yang, Prof. Jon T. Njardarson, Dr. Cristian Draghici and Dr. Fang Li

      Article first published online: 1 JUL 2013 | DOI: 10.1002/anie.201304624

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      Carbocyclic cage fight: The substrate-controlled total synthesis of vinigrol features a strategic oxidative dearomatization/Diels–Alder cycloaddition reaction and a subsequent palladium-catalyzed cyclization cascade to construct the carbocyclic core. The C4, C9, and C12 stereocenters were installed using either reduction or oxidation reactions, and the diterpenoid core was unraveled by a ring fragmentation reaction.

    24. Ligand Design

      ChenPhos: Highly Modular P-Stereogenic C1-Symmetric Diphosphine Ligands for the Efficient Asymmetric Hydrogenation of α-Substituted Cinnamic Acids (pages 8652–8656)

      Dr. Weiping Chen, Dr. Felix Spindler, Dr. Benoit Pugin and Dr. Ulrike Nettekoven

      Article first published online: 1 JUL 2013 | DOI: 10.1002/anie.201304472

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      These cats are purrfectionists: The ChenPhos ligands (see structure) showed dramatically higher catalytic activity in the title reaction than their C2-symmetric predecessor with two dimethylaminoethyl-substituted ferrocenyl(phenyl)phosphanyl groups. The ready accessibility, extreme air stability, and high enantioselectivity, activity, and productivity of these ligands make them very promising for a wide range of practical applications.

    25. Radical C[BOND]H Oxidation

      Site-Selective Oxidation of Unactivated Cmath image[BOND]H Bonds with Hypervalent Iodine(III) Reagents (pages 8657–8660)

      Dr. Shin A. Moteki, Asuka Usui, Tiexin Zhang, César R. Solorio Alvarado and Prof. Dr. Keiji Maruoka

      Article first published online: 3 JUL 2013 | DOI: 10.1002/anie.201304359

      Thumbnail image of graphical abstract

      By design: The site-selective oxidation of unactivated secondary Cmath image[BOND]H bonds was accomplished with hypervalent iodine(III) reagents and tert-butyl hydroperoxide (see scheme). The preparation and derivatization of the hypervalent iodine(III) reagent are simple, thus allowing the rational design of these reagents to optimize the site selectivity of the oxidation.

    26. Sulfimides

      Enantioselective Nitrene Transfer to Sulfides Catalyzed by a Chiral Iron Complex (pages 8661–8665)

      Dr. Jun Wang, Marcus Frings and Prof. Dr. Carsten Bolm

      Article first published online: 3 JUL 2013 | DOI: 10.1002/anie.201304451

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      Iron works: Enantioselective nitrene transfer to sulfide was accomplished by a chiral iron(III)/PyBOX catalyst (see scheme). Various sulfimides were thus obtained in high enantioselectivities and yields. Applications of this protocol to the syntheses of enantioenriched sulfoximines and an epoxide were also demonstrated.

    27. Optoelectronics

      Conductance Switching and Mechanisms in Single-Molecule Junctions (pages 8666–8670)

      Chuancheng Jia, Jinying Wang, Changjiang Yao, Yang Cao, Prof. Yuwu Zhong, Prof. Zhirong Liu, Prof. Zhongfan Liu and Prof. Xuefeng Guo

      Article first published online: 1 JUL 2013 | DOI: 10.1002/anie.201304301

      Thumbnail image of graphical abstract

      A molecular switch: The conductance of a new molecular device based on graphene–molecule junctions was reproducibly switched between open and closed states under irradiation of external light (see picture). Three photochromic diarylethene derivatives with different substituents were used as key elements of the molecular devices.

    28. Non-Natural Polysaccharides

      A Crystal-to-Crystal Synthesis of Triazolyl-Linked Polysaccharide (pages 8671–8675)

      Atchutarao Pathigoolla and Prof. Dr. Kana M. Sureshan

      Article first published online: 1 JUL 2013 | DOI: 10.1002/anie.201303372

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      Crystal sweets: Polysaccharide synthesis is hampered by many factors. These problems can be circumvented by the crystal-to-crystal azide–alkyne cycloaddition polymerization of an unprotected monosaccharide, which gives a crystalline glycopolymer regiospecifically in quantitative yield.

    29. Heck Reaction

      Palladium-Catalyzed Asymmetric Intermolecular Cyclization (pages 8676–8680)

      Dr. Jian Hu, Prof. Dr. Hajime Hirao, Dr. Yongxin Li and Prof. Dr. Jianrong (Steve) Zhou

      Article first published online: 3 JUL 2013 | DOI: 10.1002/anie.201303753

      Thumbnail image of graphical abstract

      Domino cyclization: Alkylpalladium intermediates in an asymmetric Heck reaction were intercepted by a second alkene to give tricyclic products with high enantioselectivity (see scheme; Boc=tert-butoxycarbonyl). The method was applied to the asymmetric synthesis of a precursor of (−)-martinellic acid, a folk eye medicine in South America.

    30. Protein Modification

      Ligand-Directed Selective Protein Modification Based on Local Single-Electron-Transfer Catalysis (pages 8681–8684)

      Dr. Shinichi Sato and Prof. Hiroyuki Nakamura

      Article first published online: 3 JUL 2013 | DOI: 10.1002/anie.201303831

      Thumbnail image of graphical abstract

      A photocatalyst ([Ru(bpy)3]2+) bound to a protein ligand was essential for the title method. Local single-electron transfer from the catalyst resulted in the formation of tyrosyl radicals. N′-Acetyl-N,N-dimethyl-1,4-phenylenediamine was used as the tyrosyl radical trapping agent and used in a radical addition to afford selective modification of the target protein.

    31. Graphene

      Graphene Oxide Nanoribbons from the Oxidative Opening of Carbon Nanotubes Retain Electrochemically Active Metallic Impurities (pages 8685–8688)

      Colin Hong An Wong, Chun Kiang Chua, Bahareh Khezri, Richard D. Webster and Prof. Martin Pumera

      Article first published online: 6 JUN 2013 | DOI: 10.1002/anie.201303837

      Thumbnail image of graphical abstract

      Metallic impurities: Graphene oxide nanoribbons (GONRs) are commonly synthesized using carbon nanotubes (CNTs) as a precursor (see picture). The CNTs contain significant amounts of metallic impurities even after purification. These impurities persist after oxidative opening of the CNTS to GONRs and heavily influence the electrochemical behavior of the resulting material.

      Corrected by:

      Corrigendum: Corrigendum: Graphene Oxide Nanoribbons from the Oxidative Opening of Carbon Nanotubes Retain Electrochemically Active Metallic Impurities

      Vol. 53, Issue 21, 5233, Article first published online: 14 MAY 2014

    32. Electron Transfer

      Nitroxyl Radicals for Studying Electron Transfer (pages 8689–8692)

      Dr. Tamar Eliash, Dr. Antonio Barbon, Prof. Marina Brustolon, Prof. Mordechai Sheves, Dr. Itzhak Bilkis and Dr. Lev Weiner

      Article first published online: 1 JUL 2013 | DOI: 10.1002/anie.201210207

      Thumbnail image of graphical abstract

      Electron-transfer (ET) rates are measured by use of time-resolved EPR spectroscopy, involving photooxidation of nitroxyl radicals by a ruthenium bipyridyl complex. This permits acquisition of the fundamental characteristics of ET in solution. The method was used on two spin-labeled derivatives of bacteriorhodopsin, and is applicable to proteins, nucleic acids, and biological membranes.

    33. Mesoporous Materials

      Gel-Free Secondary Growth of Uniformly Oriented Silica MFI Zeolite Films and Application for Xylene Separation (pages 8693–8698)

      Dr. Tung Cao Thanh Pham, Thanh Huu Nguyen and Prof. Dr. Kyung Byung Yoon

      Article first published online: 5 JUL 2013 | DOI: 10.1002/anie.201301766

      Thumbnail image of graphical abstract

      Zeolite membranes: A promising method is reported for the fabrication of oriented silica MFI zeolite films (see picture; TPAOH=tetrapropylammonium hydroxide). The films synthesized by using this method exhibit an outstanding performance for the separation of p- and o-xylene.

    34. DNA Nanostructures

      Thermostable Branched DNA Nanostructures as Modular Primers for Polymerase Chain Reaction (pages 8699–8702)

      Mark R. Hartman, Dr. Dayong Yang, Dr. Thua N. N. Tran, Dr. Kwang Lee, Jason S. Kahn, Pichamon Kiatwuthinon, Kenneth G. Yancey, Oleksandr Trotsenko, Prof. Sergiy Minko and Prof. Dan Luo

      Article first published online: 3 JUL 2013 | DOI: 10.1002/anie.201302175

      Thumbnail image of graphical abstract

      Chemical cross-linking was used to prepare DNA nanostructures with enhanced thermal stability. These thermostable DNA nanostructures were then utilized as modular primers in the polymerase chain reaction (PCR; see picture), thus enabling the production of multifunctionalized and branched PCR products for multiplexed detection and hydrogel formation.

    35. Reductive Aldol Reaction

      Diisopinocampheylborane-Mediated Reductive Aldol Reactions: Highly Enantio- and Diastereoselective Synthesis of syn Aldols from N-Acryloylmorpholine (pages 8703–8707)

      Dr. Philippe Nuhant, Dr. Christophe Allais and Prof. Dr. William R. Roush

      Article first published online: 1 JUL 2013 | DOI: 10.1002/anie.201302535

      Thumbnail image of graphical abstract

      Cutting costs, cutting corners: In an inexpensive and straightforward synthesis of syn-propionamide aldols, formation of the Z enolborinate by the hydroboration of 4-acryloylmorpholine with diisopinocampheylborane ((Ipc)2BH) was followed by aldol reactions with achiral and chiral aldehydes to provide syn-α-methyl-β-hydroxymorpholinecarboxamides with excellent enantio- and diastereoselectivity (see scheme; R=alkyl, alkenyl, aryl, heteroaryl).

    36. Self-Assembly

      Room-Temperature Ice Growth on Graphite Seeded by Nano-Graphene Oxide (pages 8708–8712)

      Dr. Yi Zheng, Dr. Chenliang Su, Dr. Jiong Lu and Prof. Kian Ping Loh

      Article first published online: 3 JUL 2013 | DOI: 10.1002/anie.201302608

      Thumbnail image of graphical abstract

      Ice to see you: The Stenocara beetle in the Namib Desert collects drinking droplets from the morning mist using its waxy wings, which are tailored with sub-millimeter hydrophilic humps. Superhydrophilic graphene oxide nanoflakes are biomimetic analogues of these humps and can seed ice nucleation on hydrophobic graphite. Various ice solids can thus be grown at ambient conditions (see images).

    37. Organic Nanophotonics

      Controlling the Structures and Photonic Properties of Organic Nanomaterials by Molecular Design (pages 8713–8717)

      Wei Yao, Dr. Yongli Yan, Dr. Lin Xue, Chuang Zhang, Guoping Li, Prof. Qingdong Zheng, Prof. Yong Sheng Zhao, Prof. Hua Jiang and Prof. Jiannian Yao

      Article first published online: 5 JUL 2013 | DOI: 10.1002/anie.201302894

      Thumbnail image of graphical abstract

      Exploring the stacks: Two different but related naphthalene compounds were shown to form different nanostructures (see picture) depending on the π–π stacking and hydrogen bonding of the molecules. These nanostructures had unique photonic confinement and light-propagation characteristics, which show potential for nanophotonic circuits.

    38. Chirality

      Three-Dimensional Near-Surface Imaging of Chirality Domains with Circularly Polarized X-rays (pages 8718–8721)

      Dr. Hiroyuki Ohsumi, Akihisa Tokuda, Dr. Soshi Takeshita, Prof. Masaki Takata, Dr. Motohiro Suzuki, Dr. Naomi Kawamura, Dr. Yusuke Kousaka, Prof. Jun Akimitsu and Prof. Taka-hisa Arima

      Article first published online: 1 JUL 2013 | DOI: 10.1002/anie.201303023

      Thumbnail image of graphical abstract

      Imaging of chirality domains: Resonant circularly polarized X-ray diffraction distinguishes crystalline enantiomers (see picture). Control of the penetration depth and microfocusing of X-rays leads to a new visualization technique of the three-dimensional chirality-domain morphology, providing support to the increasing demand for the improvement of inorganic chiral crystal engineering.

    39. Photochromism

      Reversible Switching of the Luminescence of a Photoresponsive Gadolinium(III) Complex (pages 8722–8725)

      Prof. Hidetaka Nakai, Kazuhiro Kitagawa, Harutaka Nakamori, Taisuke Tokunaga, Dr. Takahiro Matsumoto, Prof. Koichi Nozaki and Prof. Seiji Ogo

      Article first published online: 1 JUL 2013 | DOI: 10.1002/anie.201303137

      Thumbnail image of graphical abstract

      From blue to red: The structure and luminescence properties of the gadolinium(III) complex 1 were investigated. Reversible switching of the luminescence of 1 in THF at room temperature by alternating light irradiation and O2 exposure is presented, during which the emission color changes as shown in the picture. Light-induced phosphorescence of 1 plays a key role in this behavior.

    40. Excitons in Photosynthesis

      Fluctuations in the Electron–Phonon Coupling of a Single Chromoprotein (pages 8726–8730)

      Ralf Kunz, Dr. Kõu Timpmann, June Southall, Prof. Dr. Richard J. Cogdell, Prof. Dr. Arvi Freiberg and Prof. Dr. Jürgen Köhler

      Article first published online: 3 JUL 2013 | DOI: 10.1002/anie.201303231

      Thumbnail image of graphical abstract

      Sequences of high resolution low-temperature emission spectra from individual light-harvesting 2 (LH2) complexes from Rhodopseudomonas acidophila reveal a much larger variety of the emission profiles than previously observed. The results provide direct evidence for substantial variations in electron–phonon coupling and concomitantly of exciton (de)localization within single pigment-protein complexes.

    41. Dye-Sensitized Solar Cells

      Towards Compatibility between Ruthenium Sensitizers and Cobalt Electrolytes in Dye-Sensitized Solar Cells (pages 8731–8735)

      Dr. Lauren E. Polander, Dr. Aswani Yella, Basile F. E. Curchod, Negar Ashari Astani, Dr. Joël Teuscher, Rosario Scopelliti, Dr. Peng Gao, Dr. Simon Mathew, Prof. Jacques-E. Moser, Dr. Ivano Tavernelli, Prof. Ursula Rothlisberger, Prof. Michael Grätzel, Dr. Md. Khaja Nazeeruddin and Dr. Julien Frey

      Article first published online: 4 JUL 2013 | DOI: 10.1002/anie.201304608

      Thumbnail image of graphical abstract

      Ruthenium and Co: Ruthenium(II) complexes remain prime candidates for dye-sensitized solar applications; however, current ruthenium sensitizers are not compatible with cobalt(II/III) electrolytes. Herein, the effect of surface insulation on device efficiency is studied by comparing two cyclometalated tris-heteroleptic ruthenium(II) complexes. This approach demonstrates a general principle that leads to unprecedented efficiency for a ruthenium(II) sensitizer used in combination with a cobalt electrolyte.

    42. Total Synthesis

      Total Synthesis and Structural Revision of Viridicatumtoxin B (pages 8736–8741)

      Prof. Dr.  K. C. Nicolaou, Dr. Christian Nilewski, Christopher R. H. Hale, Dr. Heraklidia A. Ioannidou, Dr. Abdelatif ElMarrouni and Lizanne G. Koch

      Article first published online: 24 JUL 2013 | DOI: 10.1002/anie.201304691

      Thumbnail image of graphical abstract

      Will the real viridicatumtoxin B please stand up: The total synthesis of viridicatumtoxin B resulted in its structural revision and opens the way for analogue construction and biological evaluation of this complex tetracycline-like antibiotic. The highly convergent strategy employed allows for swift construction of the entire carbocyclic framework of the molecule.

    43. Self-Assembly

      Supramolecular Organic–Inorganic Hybrid Assemblies with Tunable Particle Size: Interplay of Three Noncovalent Interactions (pages 8742–8745)

      Jasmin Düring, Anne Hölzer, Dr. Ute Kolb, Robert Branscheid and Prof. Dr. Franziska Gröhn

      Article first published online: 19 JUL 2013 | DOI: 10.1002/anie.201302773

      Thumbnail image of graphical abstract

      Gold or CdS nanoparticles and ionic dye molecules can form supramolecular assemblies with a defined size between 100 to 300 nm when using a macro-ion as template and connector. The picture shows the arangement of gold, dendrimer, and dye in the hybrid assembly (blue sphere: dendritic macro-ion, red spheres: gold, red bars: ionic dye).

    44. Protein NMR Spectroscopy

      NMR Spectroscopy of Soluble Protein Complexes at One Mega-Dalton and Beyond (pages 8746–8751)

      Dr. Andi Mainz, Prof. Dr. Tomasz L. Religa, Dr. Remco Sprangers, Dr. Rasmus Linser , Prof. Dr. Lewis E. Kay and Prof. Dr. Bernd Reif

      Article first published online: 19 JUL 2013 | DOI: 10.1002/anie.201301215

      Thumbnail image of graphical abstract

      Bigger is better: Sequential backbone assignments are obtained by NMR spectroscopy for a 1 MDa proteasome complex. The method relies on immobilization of a soluble protein complex by magic-angle spinning. Deuteration and proton detection of exchangeable sites and paramagnetic relaxation enhancement enables exploration of structural and dynamic properties of supramolecular assemblies at atomic resolution.

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