Chemistry - A European Journal

Cover image for Vol. 19 Issue 17

April 22, 2013

Volume 19, Issue 17

Pages 5201–5494

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Concept
    6. Communications
    7. Full Papers
    1. You have free access to this content
      Cover Picture: Total Synthesis and Biological Evaluation of (+)-Gambieric Acid A and Its Analogues (Chem. Eur. J. 17/2013) (page 5201)

      Kazuya Ishigai, Prof. Dr. Haruhiko Fuwa, Keisuke Hashizume, Ryo Fukazawa, Dr. Yuko Cho, Prof. Dr. Mari Yotsu-Yamashita and Prof. Dr. Makoto Sasaki

      Article first published online: 12 APR 2013 | DOI: 10.1002/chem.201390057

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      The first total synthesis of (+)-gambieric acid A, a potent antifungal marine polycyclic ether, has been accomplished by H. Fuwa, M. Sasaki et al. in their Full Paper on page 5276 ff. in a convergent manner by relying on Suzuki–Miyaura reaction for the assembly of the A/BCD- and F′GHIJ-ring fragments and a ring-closing metathesis for formation of the nonacyclic backbone. The total synthesis unambiguously establishes the structure of this extraordinary complex molecule, thus demonstrating the important role of organic synthesis in the structural elucidation of natural products.

    2. You have free access to this content
      Back Cover: New Conjugated Oligothiophenes Containing the Unique Arrangement of Internal Adjacent [All]-S,S-Oxygenated Thiophene Fragments (Chem. Eur. J. 17/2013) (page 5496)

      Shay Potash and Prof. Shlomo Rozen

      Article first published online: 12 APR 2013 | DOI: 10.1002/chem.201390060

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      Oligothiophenes with inner sulfonated rings were synthesized by using HOFCH3CN, which is easily prepared from diluted F2 and aqueous acetonitrile. This family of compounds exhibits more favorable properties, such as lower HOMO–LUMO gaps and higher reduction potentials, than other fully oxygenated, polyoxygenated, and nonoxygenated oligothiophenes. For more details, see the Full Paper by S. Rozen and S. Potash on p. 5289 ff.

  2. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Concept
    6. Communications
    7. Full Papers
    1. Graphical Abstract: Chem. Eur. J. 17/2013 (pages 5204–5213)

      Article first published online: 12 APR 2013 | DOI: 10.1002/chem.201390058

  3. News

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Concept
    6. Communications
    7. Full Papers
  4. Concept

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Concept
    6. Communications
    7. Full Papers
    1. Dye-Sensitized Solar Cells

      Molecular Design Principle of All-organic Dyes for Dye-Sensitized Solar Cells (pages 5220–5230)

      Dr. Bong-Gi Kim, Kyeongwoon Chung and Prof. Jinsang Kim

      Article first published online: 11 MAR 2013 | DOI: 10.1002/chem.201204343

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      A guiding light: All-organic dyes have shown promising potential as an effective sensitizer in DSSCs. Their chemical nature decisively affects the current generation and open-circuit voltage. Several molecular design strategies of all-organic dyes to improve DSSC performance as well as factors for the improvement of photocurrent generation and reduction of improper recombination are discussed (see figure).

  5. Communications

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Concept
    6. Communications
    7. Full Papers
    1. C[BOND]H Bond Functionalization

      Cascade Hydroamination/Redox Reaction for the Synthesis of Cyclic Aminals Catalyzed by a Combined Gold Complex and Brønsted Acid (pages 5232–5237)

      Yu-Ping He, Hua Wu, Dian-Feng Chen, Jie Yu and Prof. Liu-Zhu Gong

      Article first published online: 19 MAR 2013 | DOI: 10.1002/chem.201300052

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      Relay catalysis: An unprecedented protocol for the synthesis of cyclic aminals has been realized under the relay catalysis of a gold(I)/Brønsted acid binary system to generate cyclic aminals in excellent yields of up to 99 % with moderate to high diastereoselectivity (see scheme; up to 95:5 d.r.).

    2. Domino Reactions

      A Four-Component Reaction Involving In Situ Generated Organometallic Reagents: Straightforward Access to β-Amino Esters (pages 5238–5241)

      Dr. Erwan Le Gall and Prof. Eric Léonel

      Article first published online: 5 MAR 2013 | DOI: 10.1002/chem.201300345

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      Four in one: A straightforward synthesis of β2,3-amino esters is described through a new zinc-mediated, cobalt-catalyzed four-component reaction between organic bromides, alkyl acrylates, amines, and aldehydes (see scheme). Synthesis involves a Mannich-related conjugate addition/aza-aldol domino sequence, allowing the formation of three single bonds in one step. A reaction mechanism, emphasizing the crucial role of zinc salts, is described.

    3. Synthetic Methods

      Synthesis of Indolizines and Heterocyclic Chalcones Catalyzed by Supported Copper Nanoparticles (pages 5242–5245)

      María José Albaladejo, Dr. Francisco Alonso and Prof. Miguel Yus

      Article first published online: 7 MAR 2013 | DOI: 10.1002/chem.201204305

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      Solvent decides: Versatile copper nanoparticles (Cu NPs) on activated carbon have been found to catalyze the multicomponent synthesis of indolizines in dichloromethane and the synthesis of heterocyclic chalcones in the absence of solvent, in both cases, from pyridine-2-carbaldehyde derivatives, secondary amines, and terminal alkynes (see scheme).

    4. Tandem Reactions

      Direct Syntheses of Spiro- and Fused-Hydrofurans by a Tunable Tandem Semipinacol Rearrangement/Oxa-Michael Addition Protocol (pages 5246–5249)

      Bao-Sheng Li, Wen-Xing Liu, Dr. Qing-Wei Zhang, Prof. Dr. Shao-Hua Wang, Prof. Dr. Fu-Min Zhang, Dr. Shu-Yu Zhang, Prof. Dr. Yong-Qiang Tu and Prof. Dr. Xiao-Ping Cao

      Article first published online: 13 MAR 2013 | DOI: 10.1002/chem.201300205

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      A highly chemoselective one-pot reaction has been developed involving a tandem semipinacol rearrangement/oxa-Michael addition sequence in which the in situ generated ketol diene intermediate can be transformed specifically to either the spiro- or fused-dihydrofuran products (see scheme). This one-pot tandem reaction represents a general synthetic methodology for the syntheses of the two different kinds of furan derivatives.

    5. Organic Chemistry

      Radical-Mediated Diamination of Alkenes with Phenylhydrazine and Azodicarboxylates: Highly Diastereoselective Synthesis of trans-Diamines from Cycloalkenes (pages 5250–5254)

      Dr. Ming-Kui Zhu, Yu-Chen Chen and Prof. Dr. Teck-Peng Loh

      Article first published online: 7 MAR 2013 | DOI: 10.1002/chem.201203832

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      Metal-free synthesis: Diamination of alkenes by using phenylhydrazine and azodicarboxylates could be achieved in a one-pot manner under very mild conditions (see scheme; Boc=tert-butoxycarbonyl). This process works with the assistance of acetic acid by means of a radical mechanism and displays a high trans selectivity when cycloalkene substrates were used in the reaction.

    6. Heterogeneous Catalysis

      Core–Shell AgNP@CeO2 Nanocomposite Catalyst for Highly Chemoselective Reductions of Unsaturated Aldehydes (pages 5255–5258)

      Dr. Takato Mitsudome, Motoshi Matoba, Dr. Tomoo Mizugaki, Prof. Dr. Koichiro Jitsukawa and Prof. Dr. Kiyotomi Kaneda

      Article first published online: 15 MAR 2013 | DOI: 10.1002/chem.201204160

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      Selective silver: A core–shell AgNP–CeO2 nanocomposite (AgNP@CeO2) acted as an effective catalyst for the chemoselective reductions of unsaturated aldehydes to unsaturated alcohols with H2 (see figure). Maximizing the AgNP–CeO2 interaction successfully induced the heterolytic cleavage of H2, resulting in highly chemoselective reductions. Furthermore, a highly dispersed AgNP@CeO2 system was also developed that exhibited a higher activity than the original AgNP@CeO2.

    7. Combinatorial Chemistry

      Dynamic Multivalency for Carbohydrate–Protein Recognition through Dynamic Combinatorial Libraries Based on FeII–Bipyridine Complexes (pages 5259–5262)

      Philipp Reeh and Prof. Javier de Mendoza

      Article first published online: 11 MAR 2013 | DOI: 10.1002/chem.201300464

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      Molecular recognition: Dynamic combinatorial libraries (DCLs) exploiting multivalency effects and metal coordination have been employed for carbohydrate–protein recognition. The interaction of a three-component DCL based on 2,2′-bipyridine (bipy)–FeII complexes with concanavalin A (ConA; see scheme) results in enhanced binding by multivalent presentation with a bias towards mannose-containing library components.

  6. Full Papers

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Concept
    6. Communications
    7. Full Papers
    1. Bismuth Reagents

      Synthesis and Characterisation of Bismuth(III) Aminoarenesulfonate Complexes and Their Powerful Bactericidal Activity against Helicobacter pylori (pages 5264–5275)

      Dr. Madleen Busse, Iman Trinh, Prof. Peter C. Junk, Assoc. Prof. Richard L. Ferrero and Prof. Philip C. Andrews

      Article first published online: 27 MAR 2013 | DOI: 10.1002/chem.201204220

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      Joining the fight: Bismuth(III) aminoarenesulfonates are accessible from the parent sulfonic acids through metathesis reactions with Ag2O and BiCl3, or directly through treatment with [Bi(OtBu)3] (see scheme). The zwitterionic nature of the aminosulfonic acids precludes synthesis from [Bi(Ph)3]. The bismuth complexes show high bactericidal activity (≥0.049 μg mL−1) against three infectious strains of Helicobacter pylori, often orders of magnitude more powerful than current standard bismuth-based therapies used to combat cancer and peptic ulcer disease.

    2. Total Synthesis

      Total Synthesis and Biological Evaluation of (+)-Gambieric Acid A and Its Analogues (pages 5276–5288)

      Kazuya Ishigai, Prof. Dr. Haruhiko Fuwa, Keisuke Hashizume, Ryo Fukazawa, Dr. Yuko Cho, Prof. Dr. Mari Yotsu-Yamashita and Prof. Dr. Makoto Sasaki

      Article first published online: 28 MAR 2013 | DOI: 10.1002/chem.201204303

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      Ring the changes: The first total synthesis of (+)-gambieic acid A has been accomplished by exploiting synthetic methodologies developed in our laboratory, including the Suzuki–Miyaura coupling of enol phosphates. The present total synthesis has established the absolute configuration of the natural product (see scheme). Moreover, the antifungal and antiproliferative activities of GAA and its several synthetic analogues were evaluated.

    3. Oxygen Transfer

      New Conjugated Oligothiophenes Containing the Unique Arrangement of Internal Adjacent [All]-S,S-Oxygenated Thiophene Fragments (pages 5289–5296)

      Shay Potash and Prof. Shlomo Rozen

      Article first published online: 27 MAR 2013 | DOI: 10.1002/chem.201203936

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      The oxygen-transfer agent that can: For the first time it was possible to construct the long sought after combinations of oligothiophenes containing both thiophenes and internal adjacent S,S-dioxothiophenes (see scheme). Some of these combinations exhibit very narrow HOMO–LUMO gaps.

    4. Nanostructures

      Controlled Synthesis of Thorium and Uranium Oxide Nanocrystals (pages 5297–5305)

      Dr. Damien Hudry, Dr. Christos Apostolidis, Dr. Olaf Walter, Dr. Thomas Gouder, Dr. Eglantine Courtois, Dr. Christian Kübel and Dr. Daniel Meyer

      Article first published online: 4 MAR 2013 | DOI: 10.1002/chem.201203888

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      New pieces to the puzzle! Thorium and uranium oxide nanocrystals with various sizes and shapes were synthesised by a non-aqueous colloidal method (see figure). The role of various experimental parameters (e.g., composition of the organic system, nature of the actinide precursor and nature of the actinide element) to control the final characteristics of actinide oxide nanocrystals is reported.

    5. Thin Films

      Self-Organization of Honeycomb-like Porous TiO2 Films by means of the Breath-Figure Method for Surface Modification of Titanium Implants (pages 5306–5313)

      Hong Li, Dr. Yi Jia, Dr. Mingchun Du, Dr. Jinbo Fei, Dr. Jie Zhao, Dr. Yue Cui and Prof. Dr. Junbai Li

      Article first published online: 28 FEB 2013 | DOI: 10.1002/chem.201203353

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      A honey of an idea: Honeycomb-like porous TiO2 films have been fabricated with an organometallic small-molecule precursor by using the breath-figure method (see figure; TBT=titanium n-butoxide). The pore size of the TiO2 films could be modulated by varying the experimental parameters. The in vitro cell-culture experiments indicate that porous TiO2 films are an attractive biomaterial for surface modification of titanium implants in tissue engineering.

    6. Chelates

      Tuning the Photoisomerization of a N^C-Chelate Organoboron Compound with a Metal[BOND]Acetylide Unit (pages 5314–5323)

      Nan Wang, Dr. Soo-Byung Ko, Jia-Sheng Lu, Leanne D. Chen and Prof. Suning Wang

      Article first published online: 4 MAR 2013 | DOI: 10.1002/chem.201204048

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      Showing your metal: Metal[BOND]acetylides with different triplet energies influence the photoisomerization efficiency of a N C-boron compound, thus enabling the tuning of the photoactivity of organoboron-based photochromic systems with metal ions (see scheme).

    7. Metal–Organic Frameworks

      Three-Dimensional MOF-Type Architectures with Tetravalent Uranium Hexanuclear Motifs (U6O8) (pages 5324–5331)

      Clément Falaise, Dr. Christophe Volkringer, Dr. Jean-François Vigier, Dr. Natacha Henry, Dr. Arnaud Beaurain and Dr. Thierry Loiseau

      Article first published online: 16 JAN 2013 | DOI: 10.1002/chem.201203914

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      In the open: Open frameworks of uranium(IV) compounds have been synthesized solvothermally by using dicarboxylate ligands in N,N-dimethylformamide. MOF-type structures are built up from the connection of hexanuclear [U6O4(OH)4(H2O)6] units in a fcc fashion by the ditopic ligands. This generates a 3D open framework (see figure) with octahedral and tetrahedral cavities, similar to Zr-based UiO-66/67 phases.

    8. Nanostructures

      Hydroxyapatite Hierarchically Nanostructured Porous Hollow Microspheres: Rapid, Sustainable Microwave-Hydrothermal Synthesis by Using Creatine Phosphate as an Organic Phosphorus Source and Application in Drug Delivery and Protein Adsorption (pages 5332–5341)

      Chao Qi, Prof. Dr. Ying-Jie Zhu, Bing-Qiang Lu, Xin-Yu Zhao, Jing Zhao, Feng Chen and Dr. Jin Wu

      Article first published online: 4 MAR 2013 | DOI: 10.1002/chem.201203886

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      Sleepy hollow: Hydroxyapatite (HAP) microspheres were synthesized from creatine phosphate as a biocompatible phosphorus source (see figure). As-prepared nanostructured porous hollow microspheres show relatively high drug-loading and high protein-adsorption capacity.

    9. Complex Chemistry

      Reactions of Copper(II) Chloride in Solution: Facile Formation of Tetranuclear Copper Clusters and Other Complexes That Are Relevant in Catalytic Redox Processes (pages 5342–5351)

      Sabine Löw, Jonathan Becker, Christian Würtele, Andreas Miska, Dr. Christian Kleeberg, Prof. Dr. Ulrich Behrens, Dr. Olaf Walter and Prof. Dr. Siegfried Schindler

      Article first published online: 28 FEB 2013 | DOI: 10.1002/chem.201203848

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      Colorful complex chemistry: A mixture of copper chloride together with benzylamine in alcoholic solutions leads to complex colorful reactions (see figure). Although an olive green copper cluster could be easily identified, it was much more difficult to characterize the other complexes formed in this reaction mixture. The reactivity of these complexes has been investigated and demonstrated the high reactivity of these species in oxidation reactions of organic substrates.

    10. Langmuir–Blodgett Films

      Controlling the Structural and Electrical Properties of Diacid Oligo(Phenylene Ethynylene) Langmuir–Blodgett Films (pages 5352–5363)

      Dr. Luz Marina Ballesteros , Dr. Santiago Martín , Javier Cortés , Santiago Marqués-González, Prof. Simon J. Higgins, Prof. Richard J. Nichols, Prof. Paul J. Low and Dr. Pilar Cea 

      Article first published online: 27 FEB 2013 | DOI: 10.1002/chem.201203261

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      Modulation of conductance in Langmuir–Blodgett (LB) films of a symmetrically acid-terminated oligomeric phenylene ethynylene derivative was achieved by means of the pH value of the aqueous subphase from which the corresponding Langmuir films were transferred. Current–voltage curves of the LB films on a gold substrate (see figure), recorded with an STM tip positioned just above the monolayer, and good fits to the Simmons model indicate that charge flow through the metal |molecule|metal junction occurs by a non-resonant tunnelling mechanism.

    11. 19F NMR spectroscopy

      Fluorinated Carbohydrates as Lectin Ligands: Dissecting Glycan–Cyanovirin Interactions by Using 19F NMR Spectroscopy (pages 5364–5374)

      Dr. Elena Matei, Dr. Sabine André, Dr. Anja Glinschert, Angela Simona Infantino, Prof. Dr. Stefan Oscarson, Prof. Dr. Hans-Joachim Gabius and Prof. Dr. Angela M. Gronenborn

      Article first published online: 28 FEB 2013 | DOI: 10.1002/chem.201204070

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      Dissect and detect: A facile 19F NMR spectroscopic approach is presented that exploits the favorable properties of fluorinated carbohydrates for sensing the binding of glycan to lectins (see figure). Ligand-detected 19F NMR spectroscopy was employed to evaluate the interactions between di- and trimannoside with the anti-HIV lectin cyanovirin-N, and demonstrate that new features in their binding modes can be discerned.

    12. Dyes/Pigments

      Synthesis of Luminescent Ethynyl-Extended Regioisomers of Borate Complexes Based on 2-(2′-Hydroxyphenyl)benzoxazole (pages 5375–5386)

      Dr. Julien Massue, Denis Frath, Pascal Retailleau, Dr. Gilles Ulrich and Dr. Raymond Ziessel

      Article first published online: 27 FEB 2013 | DOI: 10.1002/chem.201203625

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      Tuning the light: Thirteen solution- and solid-state luminescent ethynyl-extended tetrahedral borate complexes based on 2-(2′-hydroxyphenyl)benzoxazole (HBO) have been synthesized and the emission properties can be fine-tuned by introducing a dibutylaminophenylethynyl substituent at different positions of the HBO core (3, 4, or 5). Each regioisomer displays a distinctive color spanning from green to yellow or orange (see figure).

    13. Metal–Organic Frameworks

      Systematic Investigation of Silver–Carbon Bonding in Coordination Frameworks with Aryl Ligands That Contain Ethynyl and Ethenyl Substituents (pages 5387–5400)

      Dr. Sam C. K. Hau and Prof. Dr. Thomas C. W. Mak

      Article first published online: 28 FEB 2013 | DOI: 10.1002/chem.201204225

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      Hi ho silver lining: A structural investigation of silver(I) trifluoroacetates with aromatic ligands that were functionalized with terminal and internal ethynyl groups and a vinyl substituent was performed. AgL⋅6 AgCF3CO2 H2O MeOH (HL=1-{[4-(prop-2-ynyloxy)-3-vinylphenyl]ethynyl}naphthalene) is the first example that contained all four principal types of AgI[BOND]C bonding (Ag[BOND]ethynide, Ag[BOND]ethynyl, Ag[BOND]ethenyl, and Ag[BOND]aromatic).

    14. DNA Intercalators

      You have full text access to this OnlineOpen article
      Initial DNA Interactions of the Binuclear Threading Intercalator Λ,Λ-[μ-bidppz(bipy)4Ru2]4+: An NMR Study with [d(CGCGAATTCGCG)]2 (pages 5401–5410)

      Lisha Wu, Dr. Anna Reymer, Dr. Cecilia Persson, Dr. Krzysztof Kazimierczuk, Prof. Tom Brown, Prof. Per Lincoln, Prof. Bengt Nordén and Prof. Martin Billeter

      Article first published online: 28 FEB 2013 | DOI: 10.1002/chem.201203175

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      Intercalator trapped in the minor groove: NMR analysis shows that the binuclear RuII threading intercalator Λ,Λ-[μ-bidppz(bipy)4Ru2]4+ (bidppz=11,11′-bis(dipyrido[3,2-a:2′,3′-c]phenazinyl, bipy=2,2′-bipyridine) does not intercalate palindromic DNA [d(CGCGAATTCGCG)]2, but is trapped in a well-defined surface-bound state consisting of an eccentric minor-groove position (see figure). The structure may represent the fast initial binding step of thread-intercalators, which subsequently penetrate the base stack by a very slow process.

    15. Gels

      The Formation of CuCl2-Specific Metallogels of Pyridyloxalamide Derivatives in Alcohols (pages 5411–5416)

      Dr. Zoran Džolić, Dr. Massimo Cametti, Dr. Dalibor Milić and Prof. Mladen Žinić

      Article first published online: 27 FEB 2013 | DOI: 10.1002/chem.201204082

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      Fallen an-gel: Isomeric pyridyloxalamide derivatives 13, which differed in the position of the nitrogen atom on the pyridyl ring, showed remarkably different gel-forming aptitudes in the presence of CuCl2 salt in alcohols. Whilst derivatives 1 and 3 formed a soluble complex and a solid precipitate, respectively, ligand 2 generated a remarkably metal- and anion-specific metallogel (see figure).

    16. Nanotubes

      Nucleation and Growth of Chrysotile Nanotubes in H2SiO3/MgCl2/NaOH Medium at 90 to 300 °C (pages 5417–5424)

      Romain Lafay, Dr. German Montes-Hernandez, Dr. Emilie Janots, Dr. Rodica Chiriac, Nathaniel Findling and François Toche

      Article first published online: 27 FEB 2013 | DOI: 10.1002/chem.201204105

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      Growing pains: The synthesis of chrysotile nanotubes can be summarized in three steps: the formation of proto-serpentine and brucite; the nucleation and growth of chrysotile by dissolution of the transient phases; and Ostwald ripening growth (see figure).

    17. Hydrogen Transfer

      UV-Light-Induced Hydrogen Transfer in Guanosine–Guanosine Aggregates (pages 5425–5431)

      Katharina Hunger, Laura Buschhaus, Dr. Lars Biemann, Michaela Braun, Dr. Sergey Kovalenko, Dr. Roberto Improta and Prof. Karl Kleinermanns

      Article first published online: 4 MAR 2013 | DOI: 10.1002/chem.201204286

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      GG whiz: Upon UV irradiation of lipophilic guanosine–guanosine (GG) aggregates, (G−H). radicals are formed through G+G charge transfer followed by proton transfer along the NH⋅⋅⋅N hydrogen bond. The calculated superimposed spectrum of the ions and the radicals that result from hydrogen transfer agrees with the experimental spectrum (see figure).

    18. Asymmetric Catalysis

      Cu-Catalyzed Asymmetric Allylic Alkylation of Phosphonates and Phosphine Oxides with Grignard Reagents (pages 5432–5441)

      Dr. Valentín Hornillos, Dr. Manuel Pérez, Dr. Martín Fañanás-Mastral and Prof. Dr. Ben L. Feringa

      Article first published online: 27 FEB 2013 | DOI: 10.1002/chem.201204364

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      Phosphorus in control: An efficient and highly enantioselective copper-catalyzed allylic alkylation of phosphonates and phosphine oxides with Grignard reagents and TaniaPhos or phosphoramidites as chiral ligands is reported (see scheme). Transformation of these products leads to a variety of new chiral, phosphorus-containing intermediates.

    19. Functional Nanoparticles

      Synthesis and Properties of Oval-Shaped Iron Oxide/Ethylene Glycol Mesostructured Nanosheets (pages 5442–5449)

      Dr. Xi Wang, Yijun Yang, Dr. Tianyou Zhai, Yeteng Zhong, Dr. Zhanjun Gu, Prof. Y. Charles Cao, Prof. Yuliang Zhao, Dr. Ying Ma and Prof. Jiannian Yao

      Article first published online: 28 FEB 2013 | DOI: 10.1002/chem.201202452

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      A simple bottom-up route has been used to synthesize oval-shaped FeOx/ethylene glycol mesostructured nanosheets (see picture). These materials exhibit a low Morin transition temperature TM and ferromagnetism below this temperature due to the ultrathinness of the iron oxide slabs. The interlayer spacing of the iron oxide slabs can be easily controlled by employing different glycol molecules.

    20. Flow Chemistry

      A Continuous-Flow Process for the Synthesis of Artemisinin (pages 5450–5456)

      Dr. Daniel Kopetzki, Dr. François Lévesque and Prof. Dr. Peter H. Seeberger

      Article first published online: 20 MAR 2013 | DOI: 10.1002/chem.201204558

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      With light against malaria: Artemisinin, an important antimalarial drug, is synthesized from dihydroartemisinic acid through a highly energy-efficient high-yielding one-pot continuous-flow process.

    21. Dimerization

      Steric Control in the π-Dimerization of Oligothiophene Radical Cations Annelated with Bicyclo[2.2.2]octene Units (pages 5457–5467)

      Masaki Tateno, Dr. Masayoshi Takase, Prof. Masahiko Iyoda, Prof. Koichi Komatsu and Prof. Tohru Nishinaga

      Article first published online: 28 FEB 2013 | DOI: 10.1002/chem.201204332

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      Drive and dimerization: A series of oligothiophenes annelated with bicyclo[2.2.2]octene units were synthesized to investigate the driving forces of π-dimerization and the structure–property relationships of the π-dimers of oligothiophene radical cations (see figure). Combined with DFT calculations, the SOMO–SOMO interaction was found to be the most important factor affecting π-dimerization enthalpy.

    22. Metallacycles

      Synthesis, Structural Characterisation and Stereochemical Investigation of Chiral Sulfur-Functionalised N-Heterocyclic Carbene Complexes of Palladium and Platinum (pages 5468–5475)

      Dr. Deepa Krishnan, Dr. Sumod A. Pullarkat, Meiyi Wu, Dr. Yongxin Li and Prof. Pak-Hing Leung

      Article first published online: 28 FEB 2013 | DOI: 10.1002/chem.201204320

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      Locked in place: Structurally rigid palladium and platinum metallacycles containing sulfur-functionalised N-heterocyclic carbene chelate ligands are stereochemically locked in a chiral ring conformation that is either (Rs,S,R)-λ or (Ss,R,R)-δ in both the solid state and solution (see scheme). The absolute conformations of these structurally rigid metallacycles were determined by XRD and 2D 1H–1H ROESY NMR spectroscopy techniques.

    23. Natural Products

      Enantioselective Total Synthesis of (+)-Ophiobolin A (pages 5476–5486)

      Kazuhiro Tsuna, Naoyoshi Noguchi and Prof. Dr. Masahisa Nakada

      Article first published online: 28 FEB 2013 | DOI: 10.1002/chem.201204119

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      Grade A synthesis: The enantioselective synthesis of (+)-ophiobolin A featured an intramolecular Hosomi–Sakurai cyclization, Utimoto's coupling reaction, and the construction of the eight-membered carbocyclic ring through ring-closing metathesis (see scheme).

    24. Biosensors

      Label-Free Detection of MicroRNA: Two-Step Signal Enhancement with a Hairpin-Probe-Based Graphene Fluorescence Switch and Isothermal Amplification (pages 5487–5494)

      Xiao Zhu, Dr. Xiaoming Zhou and Prof. Dr. Da Xing

      Article first published online: 28 FEB 2013 | DOI: 10.1002/chem.201204605

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      Green for GO: A label-free approach with multiple enhancement of the signal for the determination of microRNA has been developed by taking advantage of a novel graphene oxide (GO)/intercalating dye based fluorescent hairpin probe and an isothermal polymerization reaction (see scheme; SYBR Green 1: reporter molecule).

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