Chemistry – An Asian Journal

Cover image for Vol. 6 Issue 7

Special Issue: Celebrating the 150th Anniversary of the Department of Chemistry, The University of Tokyo

July 4, 2011

Volume 6, Issue 7

Pages 1629–1895

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorials
    5. Graphical Abstract
    6. News
    7. Essays
    8. Focus Reviews
    9. Communications
    10. Full Papers
    11. Preview
    1. Cover Picture (Chem. Asian J. 7/2011) (page 1629)

      Version of Record online: 30 JUN 2011 | DOI: 10.1002/asia.201190025

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      This year the Department of Chemistry of The University of Tokyo is celebrating its 150th anniversary. To commemorate this occasion and to honor the department's tradition of excellence, this special issue featuring top contributions from international scientists closely linked with the department is dedicated to this anniversary. This issue contains two Editorials and two Essays that tell the story of the department with a concentration on the backdrop of history and the timeline of key research developments, as well as five Focus Reviews and 20 original research papers covering the whole spectrum of chemistry. The cover picture, provided by the issue co-organizers Shū Kobayashi and Eiichi Nakamura, captures the excellent history and the many faces of the department. Cover image designed by Mr. Shuzaburo Shibi.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorials
    5. Graphical Abstract
    6. News
    7. Essays
    8. Focus Reviews
    9. Communications
    10. Full Papers
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    1. Inside Cover: New Design Tactics in OLEDs Using Functionalized 2-Phenylpyridine-Type Cyclometalates of Iridium(III) and Platinum(II) (Chem. Asian J. 7/2011) (page 1630)

      Prof. Guijiang Zhou, Prof. Wai-Yeung Wong and Xiaolong Yang

      Version of Record online: 30 JUN 2011 | DOI: 10.1002/asia.201190026

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      Organic light-emitting diodes (OLEDs) show great promise in revolutionizing next-generation display and lighting technologies. In their Focus Review on page 1706 ff., G. Zhou, W.-Y. Wong et al. discuss recent advances in using different molecular- and device-design tactics in solving many of the critical issues in OLEDs, such as efficiency enhancement, color tuning, fabrication of simpler and low-cost devices, suppression of efficiency roll-off, and high-quality white-light generation.

  3. Editorials

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorials
    5. Graphical Abstract
    6. News
    7. Essays
    8. Focus Reviews
    9. Communications
    10. Full Papers
    11. Preview
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  4. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorials
    5. Graphical Abstract
    6. News
    7. Essays
    8. Focus Reviews
    9. Communications
    10. Full Papers
    11. Preview
  5. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorials
    5. Graphical Abstract
    6. News
    7. Essays
    8. Focus Reviews
    9. Communications
    10. Full Papers
    11. Preview
  6. Essays

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorials
    5. Graphical Abstract
    6. News
    7. Essays
    8. Focus Reviews
    9. Communications
    10. Full Papers
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    1. History of Science

      The One Hundred and Fifty Year History of the Department of Chemistry, The University of Tokyo (pages 1653–1658)

      Kentaro Sato

      Version of Record online: 28 APR 2011 | DOI: 10.1002/asia.201100264

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      Tokyo drift: Over the 150 years since its inception in 1861, the Department of Chemistry, the University of Tokyo, has continued to be a leader of chemistry in Japan, producing a great number of talented researchers, while undergoing multiple changes in the university system and overcoming difficulties including disasters and wars. Its one and a half centuries of history is reflected upon and the achievements of researchers there are discussed.

    2. Umami Compounds

      One Hundred Years since the Discovery of the “Umami” Taste from Seaweed Broth by Kikunae Ikeda, who Transcended his Time (pages 1659–1663)

      Prof. Dr. Eiichi Nakamura

      Version of Record online: 5 APR 2011 | DOI: 10.1002/asia.201000899

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      So close you can almost taste it: In 1908, Prof. Ikeda found that glutamate was essential for a meal to taste good. He isolated it from seaweed broth, found it also in asparagus, tomato, cheese, and meat, synthesized it by hydrolysis of wheat gluten, and developed into a food additive like sugar, salt, and vinegar. His primary intention was to improve nutrition with the aid of chemistry.

  7. Focus Reviews

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorials
    5. Graphical Abstract
    6. News
    7. Essays
    8. Focus Reviews
    9. Communications
    10. Full Papers
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    1. Photolysis

      UV Photolysis of ClOOCl and the Ozone Hole (pages 1664–1678)

      Prof. Dr. Jim J. Lin, Andrew F Chen and Prof. Dr. Yuan T. Lee

      Version of Record online: 28 APR 2011 | DOI: 10.1002/asia.201100151

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      Filling a hole in ozone chemistry: The ClO dimer catalytic cycle contributes to a major part of the polar ozone loss. However, since 2007 there has been a debate over the efficiency of this cycle and the validity of current models for ozone-hole formation. Efforts aiming to resolve this debate are reviewed herein, with emphasis on new experiments to determine two critical photochemical properties of ClOOCl.

    2. Nanobatteries

      From Electron-Reservoir Complexes to Dendritic Molecular Nanobatteries (pages 1679–1687)

      Didier Astruc

      Version of Record online: 12 APR 2011 | DOI: 10.1002/asia.201100101

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      Assault and nanobattery: Electron-rich redox-robust permethylated late-transition-metal sandwiches with very negative redox potentials serve as molecular nanobatteries when they are linked to dendritic cores (see picture).

    3. Molecular Devices

      Studies on Molecular Conductors: From Organic Semiconductors to Molecular Metals and Superconductors (pages 1688–1704)

      Prof. Hayao Kobayashi, Prof. Akiko Kobayashi and Prof. Hiroyuki Tajima

      Version of Record online: 24 MAY 2011 | DOI: 10.1002/asia.201100061

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      O Pioneers! Studies on molecular conductors at The University of Tokyo were initiated in the middle of the last century by pioneering works on organic semiconductors by Akamatu and Inokuchi et al. Herein, the main results of studies on conducting molecular solids performed by the members of the Department of Chemistry at The University of Tokyo and outside collaborators are described.

    4. OLEDs

      New Design Tactics in OLEDs Using Functionalized 2-Phenylpyridine-Type Cyclometalates of Iridium(III) and Platinum(II) (pages 1706–1727)

      Prof. Guijiang Zhou, Prof. Wai-Yeung Wong and Xiaolong Yang

      Version of Record online: 9 MAY 2011 | DOI: 10.1002/asia.201000928

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      Functionalized IrIII and PtII ppy-type phosphors: A number of molecular and device design tactics can be used to address many critical issues in organic light-emitting diodes, such as efficiency enhancement, color tuning, simpler device fabrication, suppression of efficiency roll-off and high-quality white light generation, and so forth (see figure). This Review covers some recent advances in each of these topics.

    5. Biophysics

      Physical Chemistry of Biological Interfaces: Generic and Specific Roles of Soft Interlayers (pages 1728–1738)

      Prof. Dr. Motomu Tanaka, Dr. Emanuel Schneck, Dr. Hiroshi Y. Yoshikawa and Dr. Fernanda F. Rossetti

      Version of Record online: 4 MAY 2011 | DOI: 10.1002/asia.201100112

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      Interplay at interfaces: Nature defines the spatial boundaries between different phases using membranes. A comprehensive overview on the interplay of generic and specific interactions at cell–cell and cell–tissue interfaces probed by the combination of various experimental techniques and theoretical modeling is presented.

  8. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorials
    5. Graphical Abstract
    6. News
    7. Essays
    8. Focus Reviews
    9. Communications
    10. Full Papers
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    1. Rhodium Catalysis

      One-Pot Nitrile Aldolization/Hydration Operation Giving β-Hydroxy Carboxamides (pages 1740–1743)

      Dr. Akihiro Goto, Dr. Hiroshi Naka, Dr. Ryoji Noyori and Dr. Susumu Saito

      Version of Record online: 17 MAR 2011 | DOI: 10.1002/asia.201000921

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      Rhodium to the rescue: The formal aldol products of carboxamides (CONH2) were obtained by using a RhI(OR) (R=H, Me) catalyst under essentially neutral pH and ambient conditions. This novel aldol strategy is based on the catalytic aldol-type reaction of nitriles, followed by hydration of the nitrile functionality (R1=aromatic or aliphatic, R2 and R3=H or alkyl; see scheme).

    2. Solar Cells

      Double Donor-Thiophene Dendron-Perylene Monoimide: Efficient Light-Harvesting Metal-Free Chromophore for Solid-State Dye-Sensitized Solar Cells (pages 1744–1747)

      Henrike Wonneberger, Dr. Neil Pschirer, Dr. Ingmar Bruder, Dr. Jan Schöneboom, Dr. Chang-Qi Ma, Dr. Peter Erk, Dr. Chen Li, Prof. Dr. Peter Bäuerle and Prof. Dr. Klaus Müllen

      Version of Record online: 17 MAR 2011 | DOI: 10.1002/asia.201000895

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      Efficient dye-namics: A highly efficient perylene sensitizer (η=3.8 %) for solid-state dye-sensitized solar cells was obtained. Key factors for this excellent photovoltaic performance are 1) careful balance of the orbital energies and color tuning, in order to achieve a broad spectrum with high absorptivity, 2) considerate steric architecture, and 3) a sound degree of orbital partitioning.

    3. Template Synthesis

      Unsymmetrical Polymeric Ladderphanes by Sequential Polymerization: A New Approach for the Template Synthesis of Polymers with Well-Defined Chain Length and Narrow Polydispersity (pages 1748–1751)

      Yuan-Zhen Ke, Dr. Shern-Long Lee, Prof. Chun-hsien Chen and Prof. Tien-Yau Luh

      Version of Record online: 22 FEB 2011 | DOI: 10.1002/asia.201000877

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      Nothing ROMP with that: Unsymmetrical double-stranded ladderphanes are obtained by sequential ring-opening metathesis polymerization and Glaser oxidation of norbornene appended with bisalkyne moieties. Hydrolysis of these ladderphanes gives substituted poly(m-phenylene butadiynylene)s with narrow polymer dispersity index (PDI) and well-controlled degree of polymerization.

    4. Total Synthesis

      Enantioselective Total Synthesis of (−)-Euxanmodin B: An Axially Chiral Natural Product with an Anthraquinone–Xanthone Composite Structure (pages 1752–1756)

      Nobuyuki Takahashi, Takeshi Kanayama, Dr. Kumi Okuyama, Hiroko Kataoka, Haruhiko Fukaya, Prof. Dr. Keisuke Suzuki and Prof. Dr. Takashi Matsumoto

      Version of Record online: 9 MAY 2011 | DOI: 10.1002/asia.201100187

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      The first total synthesis of (−)-euxanmodin B is described. An axially chiral, enantiomerically pure biphenyl, available by enzymatic desymmetrization of σ-symmetric biaryl diacetate, was used as the key chiral biaryl building block. Two annulation reactions allowed the construction of the xanthone–anthraquinone composite structure with full stereochemical control.

    5. Hydrophobic Materials

      Fatty-Acid–Metal-Ion Complexes as Multicolor Superhydrophobic Coating Materials (pages 1757–1760)

      Dr. Li Chen, Dr. Haifeng Meng, Prof. Lei Jiang and Prof. Shutao Wang

      Version of Record online: 19 APR 2011 | DOI: 10.1002/asia.201100010

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      The amazing technicolor dreamcoating: Multicolor superhydrophobic coating materials were synthesized by the precipitation of fatty acid-metal ion (Cu2+, Zn2+, Fe3+, Co2+, and Ni2+) complexes. All of the material surfaces showed excellent water-repellent self-cleaning properties.

    6. Gold Clusters

      Affinity Clusters: An Adenine-Coated Gold Cluster Binds to Thymine Loops in DNA (pages 1761–1765)

      Prof. Takeshi Yamamura, Dr. Shinya Ariyasu and Prof. Ryota Sakamoto

      Version of Record online: 7 APR 2011 | DOI: 10.1002/asia.201000894

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      Golden balls: Two gold clusters, [Au11(PPh3)6(MA)2] 1 and [Au25(PPh3)8(MA)6Cl2]2+ 2, were synthesized. 1 binds selectively to the thymine loops (Tn) of dumbbell-type stem-loop DNAs with designed interparticle distances. MA=8-mercaptoadenine.

  9. Full Papers

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorials
    5. Graphical Abstract
    6. News
    7. Essays
    8. Focus Reviews
    9. Communications
    10. Full Papers
    11. Preview
    1. Solar Cells

      Platinum–Acetylide Polymers with Higher Dimensionality for Organic Solar Cells (pages 1766–1777)

      Dr. Qiwei Wang, Zhicai He, Andreas Wild, Prof. Hongbin Wu, Prof. Yong Cao, Prof. Ulrich  S. Schubert, Dr. Chung-Hin Chui and Prof. Wai-Yeung Wong

      Version of Record online: 7 JUN 2011 | DOI: 10.1002/asia.201100111

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      More than one dimensional! New highly branched platinum–acetylide polymers containing thiophene-triarylamine chromophores (see figure) are developed. In the proof-of-concept experiments, both the morphology and power conversion efficiency of these pseudo-3D polymers are improved relative to their linear analogue under identical testing conditions. These organometallic materials are promising for simple solution-processed polymer solar cells.

    2. Conjugate Additions

      Cooperative Activation of Alkyne and Thioamide Functionalities; Direct Catalytic Asymmetric Conjugate Addition of Terminal Alkynes to α,β-Unsaturated Thioamides (pages 1778–1790)

      Ryo Yazaki, Dr. Naoya Kumagai and Prof. Dr. Masakatsu Shibasaki

      Version of Record online: 2 MAY 2011 | DOI: 10.1002/asia.201100050

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      The dual effect: The title reaction of terminal alkynes to α,β-unsaturated thioamides has been achieved by using a soft Lewis acid/hard Brønsted base cooperative catalyst, comprising [Cu(CH3CN)4]PF6, bisphosphine ligand, and Li(OC6H4-p-OMe). Mechanistic studies revealed that the intermediate copper-thioamide enolate functioned as a Brønsted base to generate copper alkynylide from the terminal alkyne (see scheme).

    3. Structure Elucidation

      β N[BOND]O Turns and Helices Induced by β2-Aminoxy Peptides: Synthesis and Conformational Studies (pages 1791–1799)

      Zhi-Gang Jiao, Dr. Xiao-Wei Chang, Wei Ding, Dr. Guo-Jun Liu, Dr. Ke-Sheng Song, Dr. Nian-Yong Zhu, Prof. Dr. Dan-Wei Zhang and Prof. Dr. Dan Yang

      Version of Record online: 27 APR 2011 | DOI: 10.1002/asia.201000933

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      Turn this way and that: β2-Aminoxy peptides form nine-membered-ring intramolecular hydrogen bonds between adjacent residues, that is, a β N[BOND]O turn (see picture). Experimental and theoretical studies have revealed two slightly different β N[BOND]O turn conformations in the solid state and in solution for β2-aminoxy acid monomers; homochiral helices with two consecutive β N[BOND]O turns are preferred for β2-aminoxy dipeptides.

    4. Bioluminescent Probes

      Aminoluciferins as Functional Bioluminogenic Substrates of Firefly Luciferase (pages 1800–1810)

      Hideo Takakura, Ryosuke Kojima, Prof. Dr. Yasuteru Urano, Takuya Terai, Dr. Kenjiro Hanaoka and Prof. Dr. Tetsuo Nagano

      Version of Record online: 17 MAR 2011 | DOI: 10.1002/asia.201000873

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      Glow in the dark: We have shown that aminoluciferin (AL) is a versatile scaffold for bioluminogenic substrates by modification at the 6′-position. To confirm its value, we designed and synthesized a cell membrane impermeable substrate, a near-IR luminescent substrate, and a probe for caspase-3 activity.

    5. Nanoporous Networks

      2D Hexagonal Tilings Based on Triangular and Hexagonal Structural Units in the Self-Assembly of Thiacalix[4]arene Tetrasulfonate on an Au(111) Surface (pages 1811–1816)

      Dr. Ting Chen, Dr. Hui-Juan Yan, Xu Zhang, Prof. Dong Wang and Prof. Li-Jun Wan

      Version of Record online: 22 DEC 2010 | DOI: 10.1002/asia.201000640

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      2D tiles: Two-dimensional hexagonal tilings, including the Kagome network, distorted Kagome network, and snub trihexagonal tiling were observed in the adlayer of thiacalix[4]arene tetrasulfonate on an Au(111) surface (see picture). Triangular and hexagonal molecular units are the structural motifs of the tilings.

    6. Fluorescence Spectroscopy

      Lipid Bilayer Membrane of Egg-PC Liposome Evaluated as Chemical Reaction Field with Picosecond Time-Resolved Fluorescence Spectroscopy (pages 1817–1824)

      Yuki Nojima and Prof. Koichi Iwata

      Version of Record online: 9 MAY 2011 | DOI: 10.1002/asia.201100143

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      Egg on your face: Viscosity inside the lipid bilayer of egg-PC liposome is estimated by picosecond time-resolved fluorescence spectroscopy. The presence of two solvation environments within the bilayer is suggested, where one environment is 50 to 100 times more viscous than the other. The use of trans-stilbene as a probe provides valuable information on the environments inside the lipid bilayers as a field for chemical reactions.

    7. Conjugate Additions

      Conjugate Additions to Alkylidene Bis(Sulfoxides) (pages 1825–1833)

      Dr. Franck Brebion, Dr. Guillaume Vincent, Dr. Saloua Chelli, Dr. Ophélie Kwasnieski, Dr. Francisco Najera, Dr. Bénédicte Delouvrié, Prof. Ilan Marek, Dr. Etienne Derat, Dr. Jean-Philippe Goddard, Prof. Max Malacria and Prof. Louis Fensterbank

      Version of Record online: 11 MAR 2011 | DOI: 10.1002/asia.201000904

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      Taking the Michael: Alkylidene bis(sulfoxides) are exquisite Michael acceptors toward a broad series of nucleophiles, and in most cases the reaction affords the adducts in high yields with complete diastereoselectivity. Copper reagents are also good nucleophiles in this reaction, but proceed with an inversion in stereoselectivity. Rationalization was provided by DFT calculations.

    8. Gold-Cluster Cations

      Probing Structures of Small Gold Cluster Cations with Dinitrogen (pages 1834–1838)

      G. Naresh Patwari, Tomonori Ito, Kazuhiro Egashira and Akira Terasaki

      Version of Record online: 19 APR 2011 | DOI: 10.1002/asia.201000901

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      Lowering of symmetry: N2 saturation experiments revealed that, for Au6 cluster cations, the maximum number of N2 molecules adsorbed was two. Based on symmetry considerations, the marginally higher-energy chevron (C2v) structure was preferred over the most-stable triangular (D3h) structure, possibly owing to entropy effects.

    9. Diels-Alder Reactions

      Diels–Alder Reactions of Inert Aromatic Compounds within a Self-Assembled Coordination Cage (pages 1839–1847)

      Shinnosuke Horiuchi, Dr. Takashi Murase and Prof. Dr. Makoto Fujita

      Version of Record online: 18 FEB 2011 | DOI: 10.1002/asia.201000842

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      Cage against the machine: A self-assembled coordination cage can accommodate a pair of aromatic compounds and dienophiles to promote the Diels–Alder reactions of otherwise inert aromatic molecules. Preorganization of the substrate pair within the cage was quantified as a significant decrease of entropy cost and clearly illustrated by X-ray crystallographic analysis.

    10. Supramolecular Oligomers

      Linear and Hyperbranched Electron-Acceptor Supramolecular Oligomers (pages 1848–1853)

      Dr. José Santos, Dr. Emilio M. Pérez, Dr. Beatriz M. Illescas and Prof. Dr. Nazario Martín

      Version of Record online: 4 MAR 2011 | DOI: 10.1002/asia.201000832

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      Strip-tweeze: Monomers comprising one or two units of a TCAQ tweezer covalently connected to a fullerene derivative self-assemble in solution and on surfaces to form linear and hyperbranched supramolecular polymers respectively. These polymers constitute two of the first examples of purely electron-acceptor supramolecular polymers.

    11. Ionic Clusters

      Influence of MIL-101 Doping by Ionic Clusters on Hydrogen Storage Performance up to 1900 Bar (pages 1854–1859)

      Dr. Semen N. Klyamkin, Dr. Elena A. Berdonosova, Ekaterina V. Kogan, Dr. Konstantin A. Kovalenko, Prof. Danil N. Dybtsev and Prof. Vladimir P. Fedin

      Version of Record online: 15 APR 2011 | DOI: 10.1002/asia.201000871

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      One in a MIL-101: A mesoporous metal–organic framework MIL-101 was doped by ionic cluster species (see picture), and the density of adsorbed hydrogen molecules on the porous surface was determined. Doping of MIL-101 by [Re4S4F12]4− clusters increases the number of H2 binding sites 2.5 times.

    12. Allylic Substitution

      Nickel-Catalyzed Allylic Substitution of Simple Alkenes (pages 1860–1875)

      Dr. Ryosuke Matsubara and Prof. Dr. Timothy F. Jamison

      Version of Record online: 8 MAR 2011 | DOI: 10.1002/asia.201000875

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      One alkene to another: A nickel-catalyzed allylic substitution process of simple alkenes has been developed whereby an important structural motif, a 1,4-diene, was prepared (see scheme). Key for this success is the use of an appropriate nickel–phosphine complex and silyl triflate. Reactions of 1-alkyl-substituted alkenes consistently provided 1,1-disubstituted alkenes with high selectivity.

    13. Glycosides

      Direct Dehydrative Pyridylthio-Glycosidation of Unprotected Sugars in Aqueous Media Using 2-Chloro-1,3-dimethylimidazolinium Chloride as a Condensing Agent (pages 1876–1885)

      Naoki Yoshida, Dr. Masato Noguchi, Dr. Tomonari Tanaka, Takeshi Matsumoto, Naoya Aida, Dr. Masaki Ishihara, Dr. Atsushi Kobayashi and Prof. Dr. Shin-ichiro Shoda

      Version of Record online: 23 MAY 2011 | DOI: 10.1002/asia.201000896

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      Unprotected sugars! Various 2-pyridyl 1-thioglycosides have been synthesized directly from unprotected oligosaccharides in good yields by using 2-chloro-1,3-dimethyl-imidazolinium chloride as dehydrative condensing agent. The reactions proceed in aqueous media without protecting any hydroxyl groups, affording 2-pyridyl 1-thioglycosides with β-configuration selectively.

    14. Nanoscale Oxides

      Nanoscale Effects on the Stability of the λ-Ti3O5 Polymorph (pages 1886–1890)

      Dr. Rie Makiura, Dr. Yasuhiro Takabayashi, Dr. Andrew N. Fitch, Dr. Hiroko Tokoro, Prof. Dr. Shin-ichi Ohkoshi and Prof. Dr. Kosmas Prassides

      Version of Record online: 28 APR 2011 | DOI: 10.1002/asia.201100125

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      Size matters: High-resolution synchrotron X-ray diffraction experiments followed the phase-transition behavior of the photo-sensitive conducting λ-Ti3O5 binary oxide isolated in nanocrystalline form. These nanocrystals exhibited a huge hysteresis, Tc[UPWARDS ARROW]Tc[DOWNWARDS ARROW]∼110 K and exist as a single phase at temperatures as low as 383 K before a partial transformation to the semiconducting β-phase occurs.

  10. Preview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorials
    5. Graphical Abstract
    6. News
    7. Essays
    8. Focus Reviews
    9. Communications
    10. Full Papers
    11. Preview
    1. You have free access to this content
      Preview: Chem. Asian J. 8/2011 (page 1895)

      Version of Record online: 30 JUN 2011 | DOI: 10.1002/asia.201190029

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