Chemistry – An Asian Journal

Cover image for Vol. 5 Issue 8

August 2, 2010

Volume 5, Issue 8

Pages 1709–1935

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Focus Reviews
    6. Communications
    7. Full Papers
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    1. Cover Picture: Heterogeneous Aromatic Amination of Aryl Halides with Arylamines in Water with PS-PEG Resin-Supported Palladium Complexes (Chem. Asian J. 8/2010) (page 1709)

      Yoshinori Hirai and Yasuhiro Uozumi

      Article first published online: 28 JUL 2010 | DOI: 10.1002/asia.201090024

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      Catalytic aromatic amination … … has been achieved in water under heterogeneous conditions using immobilized palladium complexes of an amphiphilic polystyrene-poly(ethylene glycol) resin-supported di(tert-butyl)phosphine ligand. In their Full Paper on page 1788 ff., Y. Hirai and Y. Uozumi present the aromatic amination of aryl halides with diphenylamine and the N,N-double arylation of anilines with bromobenzene in water with broad substrate tolerance to afford triarylamines, including the optoelectronically active N,N,N′,N′-tetraaryl-1,1′-biphenyl-4,4′-diamines (TPDs), in high yield with high recyclability of the polymeric catalyst beads.

  2. Graphical Abstract

    1. Top of page
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    3. Graphical Abstract
    4. News
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    1. Graphical Abstract: Chem. Asian J. 8/2010 (pages 1712–1719)

      Article first published online: 28 JUL 2010 | DOI: 10.1002/asia.201090025

  3. News

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Focus Reviews
    6. Communications
    7. Full Papers
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  4. Focus Reviews

    1. Top of page
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    3. Graphical Abstract
    4. News
    5. Focus Reviews
    6. Communications
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    1. Palladacycles

      Allylic Imidate Rearrangements Catalyzed by Planar Chiral Palladacycles (pages 1726–1740)

      Hiroshi Nomura and Christopher J. Richards

      Article first published online: 9 JUL 2010 | DOI: 10.1002/asia.201000131

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      The palladacycle diaries: The discovery that palladacycles are efficient catalysts for the allylic imidate rearrangement has resulted in the successful application of such complexes, based on planar chiral iron and cobalt containing metallocenes, to this reaction. These complexes allow the efficient and highly enantioselective synthesis of a wide variety of protected allylic amines, valuable building blocks for use in asymmetric synthesis.

    2. Carboranes

      Recent Progress in the Chemistry of Supercarboranes (pages 1742–1757)

      Jian Zhang and Zuowei Xie

      Article first published online: 2 JUL 2010 | DOI: 10.1002/asia.201000175

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      Is it a bird? Is it a plane? Supercarboranes and supermetallacarboranes can be prepared by polyhedral expansion methodology using [12+1], [12+2], [13+1], and [14+1] procedures. This focus review offers an overview of the recent advances in this growing research field.

  5. Communications

    1. Top of page
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    1. Cyclopentane Derivatives

      Palladium-Catalyzed Intramolecular Carboacetoxylation of 4-Pentenyl-Substituted Malonate Esters with Iodobenzene Diacetate (pages 1758–1760)

      Daishi Fujino, Hideki Yorimitsu and Koichiro Oshima

      Article first published online: 2 JUN 2010 | DOI: 10.1002/asia.201000194

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      The motorcyclization diaries: Palladium-catalyzed intramolecular carboacetoxylation of 4-pentenyl-substituted malonates proceeds with the aid of titanium tetraisopropoxide and iodobenzene diacetate. The transformation represents the first PdII/PdIV catalytic oxidative process that forms an Csp3[BOND]Csp3 bond as well as a useful method for the synthesis of acetoxymethyl-substituted cyclopentanes or bicyclic lactones.

    2. Fluorescent Probes

      New Far-red and Near-infrared Fluorescent Probes with Large Stokes Shifts for Dual Covalent Labeling of DNA (pages 1761–1764)

      Thomas Ehrenschwender, Balázs R. Varga, Péter Kele and Hans-Achim Wagenknecht

      Article first published online: 29 JUN 2010 | DOI: 10.1002/asia.201000081

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      Shifty chemistry! Fluorescent coumarin dyes with large Stokes shifts are incorporated postsynthetically into oligonucleotides and combined to FRET pairs that shift the emission into the far-red/near-infrared regime. Certain FRET pairs show good potential for use in strand displacement assays.

    3. Pyrrolysine

      N6-(2-(R)-Propargylglycyl)lysine as a Clickable Pyrrolysine Mimic (pages 1765–1769)

      Xin Li, Tomasz Fekner and Michael K. Chan

      Article first published online: 11 JUN 2010 | DOI: 10.1002/asia.201000205

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      Clickable copycat! Readily available dipeptide D-Pra-ε-Lys is identified using a modified fluorescence protein assay as a highly efficient clickable pyrrolysine mimic. It is shown to incorporate into calmodulin in high yield to provide a handle for labeling with an azide-containing coumarin.

    4. Kinetic Resolution

      Catalyst versus Substrate Induced Selectivity: Kinetic Resolution by Palladacycle Catalyzed Allylic Imidate Rearrangements (pages 1770–1774)

      René Peters, Zhuo-qun Xin and Frank Maier

      Article first published online: 25 JUN 2010 | DOI: 10.1002/asia.201000386

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      Making chairs: A kinetic resolution of allylic imidates by planar chiral palladacycles is described which is the result of high face selectivity for olefin coordination to the catalyst and inherent substrate selectivity. These studies confirm that planar chiral palladacycles mainly operate via (half)chair-like transition states/intermediates.

    5. Coupling Reactions

      A New and Practical Grignard-Coupling–Fluorination Sequence: Synthesis of 2-Aryl Fluoroarenes (pages 1775–1778)

      Pazhamalai Anbarasan, Helfried Neumann and Matthias Beller

      Article first published online: 21 JUL 2010 | DOI: 10.1002/asia.201000288

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      A new strategy for the synthesis of 2-aryl- and 2-heteroaryl fluoroarenes has been developed. An intermolecular domino Grignard-coupling–fluorination sequence affords a range of 2-fluorobiaryls from aryl bromides under mild conditions. This methodology can be further extended to the synthesis of 2′-aryl-2-fluorobiphenyls.

  6. Full Papers

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    3. Graphical Abstract
    4. News
    5. Focus Reviews
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    1. Nanomaterials

      Capsules with Silver Nanoparticle Enrichment Subdomains and Their Antimicrobial Properties (pages 1780–1787)

      Anhe Wang, Yue Cui, Yang Yang and Junbai Li

      Article first published online: 25 JUN 2010 | DOI: 10.1002/asia.200900675

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      Shell game: The fabrication of polyelectrolyte multilayer capsules with controllable poly(4-vinylpyridine) (PVP) submicron-sized subdomains and the in situ synthesis of silver nanoparticles in subdomains are reported (see figure). The in situ synthesized Ag nanoparticles are stable in neutral solution and can be released from the PVP subdomains on the shell of the capsules in solution at pH 2.0.

    2. Amination

      Heterogeneous Aromatic Amination of Aryl Halides with Arylamines in Water with PS-PEG Resin-Supported Palladium Complexes (pages 1788–1795)

      Yoshinori Hirai and Yasuhiro Uozumi

      Article first published online: 22 JUN 2010 | DOI: 10.1002/asia.201000192

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      No metal, no worries! Catalytic aromatic amination is achieved in water under heterogeneous conditions by the use of palladium complexes anchored to the amphiphilic PS-PEG resin with little palladium leaching to provide a green and clean (metal-uncontaminated) protocol for the preparation of triarylamines, including the optoelectronically active N,N,N′,N′-tetraaryl-1,1′-biphenyl-4,4′-diamines (TPDs).

    3. Photocatalysis

      Photocatalytic Hydrogen Evolution by [FeFe] Hydrogenase Mimics in Homogeneous Solution (pages 1796–1803)

      Wen-Guang Wang, Feng Wang, Hong-Yan Wang, Gang Si, Chen-Ho Tung and Li-Zhu Wu

      Article first published online: 11 JUN 2010 | DOI: 10.1002/asia.201000087

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      Science imitates nature: To mimic [FeFe] hydrogenases (H2ases) in nature, molecular photocatalysts , and anchoring rhenium(I) complex S to one of the iron cores of [FeFe]-H2ases model complex C, have been constructed for H2 generation by visible light in homogeneous solution.

    4. Neuron Patterning

      Generation of Patterned Neuronal Networks on Cell-Repellant Poly(oligo(ethylene glycol) Methacrylate) Films (pages 1804–1809)

      Kyungtae Kang, Gyumin Kang, Bong Soo Lee, Insung S. Choi and Yoonkey Nam

      Article first published online: 12 APR 2010 | DOI: 10.1002/asia.200900761

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      Atom transfer radical polymerization of oligo(ethylene glycol) methacrylate (OEGMA) and subsequent activation of terminal hydroxyl groups of poly(oligo(ethylene glycol) methacrylate) (pOEGMA) with disuccinimidyl carbonate were successfully carried out for the generation of the activated pOEGMA films on glass. Poly-L-lysine was then microcontact-printed onto the activated polymer films, followed by culturing E18 hippocampal neurons on the chemically patterned substrate.

    5. Marine Alkaloid Synthesis

      Total Synthesis of (+)-Dibromophakellin and (+)-Dibromophakellstatin (pages 1810–1816)

      Takuya Imaoka, Takafumi Akimoto, Osamu Iwamoto and Kazuo Nagasawa

      Article first published online: 16 JUN 2010 | DOI: 10.1002/asia.201000213

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      New approach with enamide–Overman: Two members of the pyrrole–imidazole marine alkaloids, (+)-dibromophakellin and (+)-dibromophakellstatin, were synthesized enantioselectively from 4-hydroxy-L-proline. A new method for the preparation of quaternary chiral aminals that employs an enamide-type Overman rearrangement process has been developed.

    6. Chalcogenides

      A Series of Novel Organically Templated Germanium Antimony Sulfides (pages 1817–1823)

      Mei-Ling Feng, Wei-Wei Xiong, Dong Ye, Jian-Rong Li and Xiao-Ying Huang

      Article first published online: 10 JUN 2010 | DOI: 10.1002/asia.201000104

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      Adding dimensions: A series of novel organically templated germanium antimony sulfides have been solvothermally synthesized and structurally, thermally, and optically characterized. The current compounds realize the Ge4+/Sb3+ combination, develop the heterometallic sulfide system of Ge/Sb/S, and endue new members of the metal chalcogenide family.

    7. Transition-Metal Oxides

      Local and Remote Charge-Transfer-Enhanced Raman Scattering on One-Dimensional Transition-Metal Oxides (pages 1824–1829)

      Bin Dong, Yingzhou Huang, Naisen Yu, Yurui Fang, Baosheng Cao, Yuanzuo Li, Hongxing Xu and Mengtao Sun

      Article first published online: 10 JUN 2010 | DOI: 10.1002/asia.200900706

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      Enhancing your MBA! Local and remote charge-transfer-enhanced Raman scattering of 4-MBA adsorbed on one-dimensional transition-metal oxides (MoO3 belt) have been experimentally observed. The incident polarization dependence of remote (remote surface-enhanced Raman scattering) SERS spectra has also been investigated experimentally. The results of these investigations significantly extend the applicability of SERS.

    8. Grignard Reagents

      Catalytic Reactions of Titanium Alkoxides with Grignard Reagents and Imines: A Mechanistic Study (pages 1830–1837)

      Akshai Kumar and Ashoka G. Samuelson

      Article first published online: 16 JUN 2010 | DOI: 10.1002/asia.200900711

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      Common ground: Isotopically labeled substrates show that intermediates involved in catalytic and stoichiometric reactions of Ti(OiPr)4 with Grignard reagents differ, although under both conditions they can be trapped with imines to yield common products in different ratios (see scheme).

    9. Electrochemical Sensors

      One-Dimensional Carbon Nanotube/SnO2/Noble Metal Nanoparticle Hybrid Nanostructure: Synthesis, Characterization, and Electrochemical Sensing (pages 1838–1845)

      Youxing Fang, Shaojun Guo, Chengzhou Zhu, Shaojun Dong and Erkang Wang

      Article first published online: 25 JUN 2010 | DOI: 10.1002/asia.201000004

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      Self-assembly provides a new avenue for construction one-dimensional CNT@SnO2/nobel-metal nanoparticle hybrids through adsorbing noble-metal nanoparticles (Au, Ag, Au[BOND]Pt, and Au[BOND]Pd) onto the surface of CNT@SnO2 coaxial nanocable, which exhibited a high electrochemical sensing ability.

    10. Fluorinated Alkenes

      An Effective Preparation of Sulfonyl- or Sulfinyl-Substituted Fluorinated Alkenes and their Stereoselective Addition–Elimination Reactions with Organocuprates (pages 1846–1853)

      Shigeyuki Yamada, Kanoko Shimoji, Toshio Takahashi, Tsutomu Konno and Takashi Ishihara

      Article first published online: 10 JUN 2010 | DOI: 10.1002/asia.201000022

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      The stereoselective addition–elimination reactions of sulfur-substituted fluorinated alkenes with organocuprates have been developed. In the addition-elimination process, trifluorovinyl compounds were derivatized to form β-substituted (Z)-α,β-difluorovinyl derivatives, and pentafluoropropen-1-yl compounds were stereoselectively β-protonated via a relatively stable pentafluoropropen-1-ylcopper intermediate.

    11. ZnO-Based Sensors

      Morphology-Dependent Gas-Sensing Properties of ZnO Nanostructures for Chlorophenol (pages 1854–1859)

      Zhipeng Li, Wenxiao Pan, Dongju Zhang and Jinhua Zhan

      Article first published online: 10 JUN 2010 | DOI: 10.1002/asia.201000036

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      A sense for gas: Morphology-dependent gas-sensing properties for toxic 2-chlorophenol were investigated by using ZnO as sensors. Three different kinds of ZnO nanostructures (nanodisks, nanorods, and nanoawls) showed different sensitivity to 2-chlorophenol. Density functional theory calculations were employed to investigate the detailed sensing mechanism involving the surface reconstruction and charge-transfer process.

    12. Photolysis

      Photo-Hydrogen-Evolving Molecular Catalysts Consisting of Polypyridyl Ruthenium(II) Photosensitizers and Platinum(II) Catalysts: Insights into the Reaction Mechanism (pages 1860–1869)

      Hironobu Ozawa, Masayuki Kobayashi, Bijitha Balan, Shigeyuki Masaoka and Ken Sakai

      Article first published online: 6 JUL 2010 | DOI: 10.1002/asia.201000083

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      An improved photocatalyst: A new {RuII2PtII2} complex 2, regarded as a dimer of the first photo-hydrogen-evolving {RuIIPtII} molecular catalyst 1 (see scheme), exhibits effectively higher activity than 1, which revealed that an intramolecular pathway contributes to the observed enhancement in the photo-hydrogen-evolving activity of 2.

    13. Molecular Logic Gates

      Logic Information Communication in a Fluorescent Molecular Switch (pages 1870–1874)

      Yan-Chun Bai, Chao Zhang, Chen-Jie Fang and Chun-Hua Yan

      Article first published online: 23 JUN 2010 | DOI: 10.1002/asia.201000105

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      The ol′ switcheroo: Based on the chemical-sensitive fluorescence emission behaviors of the molecular switch 4-bromo-5-methoxy-2-(2-pyridyl)thiazole, a cascade digital circuit has been constructed that comprises an upstream-switching layer and a downstream processing layer.

    14. Lithium–Halogen Exchange

      Rapid and Slow Generation of 1-Trifluoromethylvinyllithium: Syntheses and Applications of CF3-Containing Allylic Alcohols, Allylic Amines, and Vinyl Ketones (pages 1875–1883)

      Ryo Nadano, Kohei Fuchibe, Masahiro Ikeda, Hiroki Takahashi and Junji Ichikawa

      Article first published online: 22 JUN 2010 | DOI: 10.1002/asia.201000139

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      Quick and slow: Two protocols are developed for (trifluoromethyl)vinylation with thermally unstable 3,3,3-trifluoroprop-1-en-2-yllithium for both more and less reactive electrophiles. 2-(Trifluoromethyl)allyl alcohols, amines, and 1-(trifluoromethyl)vinyl ketones are synthesized and converted to trifluoromethylated cyclopentenone derivatives by an intramolecular Pauson–Khand reaction or the Nazarov cyclization.

    15. Dendrimers

      Cyclam-Cored Dendrimers Appended with Four Dendrons of Two Different Types: Intradendrimer Energy Transfer (pages 1884–1895)

      Giacomo Bergamini, Angela Sottilotta, Mauro Maestri, Paola Ceroni and Fritz Vögtle

      Article first published online: 10 JUN 2010 | DOI: 10.1002/asia.201000170

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      The H effect! Two cyclam-cored dendrimers appended with dendrons of two different types, by proper protection/deprotection of the cyclam unit, are synthesized. Interdendron naphthyl-to-dansyl energy transfer takes place within the same dendrimer: its efficiency can be reversibly tuned by protonation/deprotonation of the cyclam core.

    16. A Dendrimer Chiroptical Switch Based on the Reversible Intramolecular Photoreaction of Anthracene and Benzene Rings (pages 1896–1901)

      Wenjie Liu, Derong Cao, Jinan Peng, Hong Zhang and Herbert Meier

      Article first published online: 25 JUN 2010 | DOI: 10.1002/asia.201000159

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      Chiroptical switching: A dendrimer chiroptical switch has been synthesized that has optical rotation values as output signals. The wavelength-dependent intramolecular photocycloaddition of anthracene and benzene rings represents the molecular basis for the process, which is sustained by the light-harvesting effect of the dendrons.

    17. Tandem Reactions

      Total Synthesis, Assignment of the Absolute Stereochemistry, and Structure-Activity Relationship Studies of Subglutinols A and B (pages 1902–1910)

      Hyoungsu Kim, Joseph B. Baker, Yongho Park, Hyung-Bae Park, Patrick D. DeArmond, Seong Hwan Kim, Michael C. Fitzgerald, Dong-Sup Lee and Jiyong Hong

      Article first published online: 16 JUN 2010 | DOI: 10.1002/asia.201000147

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      Get selective! A stereoselective synthesis of subglutinols A and B, immunosuppressive natural products, has been accomplished from the (S)-(+)-5-methyl-Wieland–Miescher ketone enlisting reductive deoxygenation, tandem cross-metathesis/intramolecular SN2′ reaction, and a CuI-mediated intermolecular SN2′ reaction (see scheme).

    18. Molecular Electronics

      Benzothiadiazole Containing D-π-A Conjugated Compounds for Dye-Sensitized Solar Cells: Synthesis, Properties, and Photovoltaic Performances (pages 1911–1917)

      Zheng-Ming Tang, Ting Lei, Ke-Jian Jiang, Yan-Lin Song and Jian Pei

      Article first published online: 11 JUN 2010 | DOI: 10.1002/asia.201000158

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      Making full use of the sun! Two benzothiadiazole containing D-π-A conjugated molecules, which possess excellent absorption coverage over the solar spectrum, were developed for dye-sensitized solar cells. The incident-photon-conversion-efficiency responsive area reached nearly 800 nm with power-conversion efficiency as high as 6.04 %.

    19. Phosphines

      Ladder-Type π-Conjugated 4-Hetero-1,4-dihydrophosphinines: A Structure–Property Study (pages 1918–1929)

      Yi Ren and Thomas Baumgartner

      Article first published online: 11 JUN 2010 | DOI: 10.1002/asia.201000196

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      Building a bridge: Changing the heteroatom and modifying the nature of the phosphorus center in the pentacene-analogue 4-heteroatomic 1,4-dihydrophosphinines allowed us to address a variety of material properties including, solid-state organization, photophysical properties, as well as redox behavior that can be related to the degree of π conjugation within the molecular scaffold.

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    4. News
    5. Focus Reviews
    6. Communications
    7. Full Papers
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      Preview: Chem. Asian J. 9/2010 (page 1935)

      Article first published online: 28 JUL 2010 | DOI: 10.1002/asia.201090027

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