Angewandte Chemie International Edition

Cover image for Angewandte Chemie International Edition

October 11, 2010

Volume 49, Issue 42

Pages 7597–7815

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    12. Preview
    1. Cover Picture: Sugar-Derived Phase-Selective Molecular Gelators as Model Solidifiers for Oil Spills (Angew. Chem. Int. Ed. 42/2010) (page 7597)

      Swapnil R. Jadhav, Dr. Praveen Kumar Vemula, Rakesh Kumar, Prof. Srinivasa R. Raghavan and Prof. George John

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201004589

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      In the near future … … molecular gels may serve in the ecologically sound cleanup of oil spills. In their Communication on page 7695 ff., G. John and co-workers describe how newly developed sugar alcohol gelators can be used for the unprecedented phase-selective gelation of various crude-oil fractions from oil–water mixtures at room temperature. The gels facilitate both the containment and the reclamation of oil.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    12. Preview
    1. Inside Cover: Amphiphilic Self-Assembly of an n-Type Nanotube (Angew. Chem. Int. Ed. 42/2010) (page 7598)

      Hui Shao, James Seifert, Natalie C. Romano, Min Gao, Jonathan J. Helmus, Prof. Christopher P. Jaroniec, Prof. David A. Modarelli and Prof. Jon R. Parquette

      Version of Record online: 10 SEP 2010 | DOI: 10.1002/anie.201005441

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      A one-dimensional n-type semiconducting nanotube is formed by the self-assembly of a naphthalenetetracarboxylic acid diimide–lysine bolaamphiphile. In their Communication on page 7688 ff., J. R. Parquette and co-workers show how the nanotubes aggregate into a monolayer membrane that curves into rings, which then stack into tubes. Solid-state NMR studies show that there is exceptional conformational homogeneity among the constituent molecules that comprise the nanotubes, leading to efficient energy migration within the assemblies.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    12. Preview
  4. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    12. Preview
  5. Author Profile

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    12. Preview
    1. Bernhard Kräutler (page 7620)

      Version of Record online: 15 SEP 2010 | DOI: 10.1002/anie.201004845

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      “Three qualities that make a good scientist are curiosity, creativity, and a very critical mind. My favorite subjects at school were art and natural sciences …” This and more about Bernhard Kräutler can be found on page 7620.

  6. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    12. Preview
  7. Book Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    12. Preview
    1. Organotransition Metal Chemistry. From Bonding to Catalysis. Edited by John F. Hartwig. (page 7622)

      Bernd F. Straub

      Version of Record online: 13 SEP 2010 | DOI: 10.1002/anie.201004890

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      University Science Books, Sausalito 2010. 1160 pp., hardcover, $ 134.50.—ISBN 978-1891389535

  8. Highlights

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    12. Preview
    1. Insulin

      Two-Chain Insulin from a Single-Chain Branched Depsipeptide Precursor: The End of a Long Journey (pages 7624–7626)

      Hans-Jürgen Musiol and Prof. Luis Moroder

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201003018

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      Coupled chains: A fully synthetic single-chain branched depsipeptide precursor lacking a proinsulin-like tethering of the A and B chains leads, by oxidative folding to the insulin characteristic cystine topology and by subsequent saponification of the ester bond, to the target two-chain insulin molecule with high efficiency (see picture; violet/blue A/B chain, yellow cystine units).

    2. Nanofluidics

      Fluidics Meets Electronics: Carbon Nanotubes as Nanopores (pages 7627–7628)

      Prof. Serge G. Lemay

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201001135

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      Go with the flow: The transport of salt ions and single-stranded DNA through individual single-walled carbon nanotubes marks the advent of a new type of solid-state nanopore. Surprisingly, the transport process shows a marked dependence on the electronic properties of the nanotubes: two nanotube “pipes” with the same diameter but different chiralities could exhibit orders of magnitude differences in ionic conductivity.

    3. Sensors

      Progress in the Chromogenic Detection of Carbon Monoxide (pages 7629–7630)

      Steven Heylen and Prof. Dr. Johan A. Martens

      Version of Record online: 29 JUL 2010 | DOI: 10.1002/anie.201002569

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      Toxic CO concentrations can be detected by a very clear induced color change of the dirhodium complex 1 (see scheme) upon binding of CO, as reported by Esteban et al. Other atmospheric compounds such as H2O, CO2, O2, CH4, SO2, NOx, and volatile organic compounds do not interfere with the CO sensing.

  9. Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    12. Preview
    1. Semiconductor Sensors

      Semiconductor Gas Sensors: Dry Synthesis and Application (pages 7632–7659)

      Dr. Antonio Tricoli, Marco Righettoni and Dr. Alexandra Teleki

      Version of Record online: 18 AUG 2010 | DOI: 10.1002/anie.200903801

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      Sense and sensitivity: Dry processes allow the rapid and scalable synthesis of nanostructured metal oxide films for use as semiconductor-based gas sensors. Dense, particulate, or porous films, with thicknesses in the nm–μm range can be prepared by the appropriate synthesis and deposition method. A wide variety of oxides with controlled properties (see pictures) are obtained, allowing miniature sensing devices with improved sensitivity and stability to be developed.

  10. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    12. Preview
    1. Coordination Polymers

      Control of Interpenetration for Tuning Structural Flexibility Influences Sorption Properties (pages 7660–7664)

      Dr. Sareeya Bureekaew, Dr. Hiroshi Sato, Dr. Ryotaro Matsuda, Dr. Yoshiki Kubota, Dr. Raita Hirose, Dr. Jungeun Kim, Dr. Kenichi Kato, Prof. Dr. Masaki Takata and Prof. Dr. Susumu Kitagawa

      Version of Record online: 2 JUL 2010 | DOI: 10.1002/anie.201002259

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      Transforming jungle gyms: Structural flexibility and sorption behavior can be tuned by controlling the degree of interpenetration of 3D porous coordination polymers (PCPs). The architectural connectivity of PCPs, even those that are composed of the same chemical components, has a significant impact on the structural flexibility and sorption behavior, which was confirmed by coincident XRPD/adsorption measurements.

    2. Porphyrinoids

      π Conjugation Transmitted across a d-Electron Metallocene in Ferrocenothiaporphyrin Macrocycles (pages 7665–7669)

      Irena Simkowa, Prof. Lechosław Latos-Grażyński and Dr. Marcin Stępień

      Version of Record online: 10 SEP 2010 | DOI: 10.1002/anie.201004015

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      Setting the 'cene: The structural features of ferrocenophanes and porphyrinoids are combined in ferrocene–porphyrin hybrids. Ferrocenothiaporphyrin (see picture, green) and dihydroferrocenothiaporphyrin (red) are macrocyclic antiaromatic and aromatic systems, respectively. These two systems provide evidence for direct transmission of π-electron conjugation across a d-electron metallocene.

    3. Alternating Copolysaccharides

      Glucose/Glucuronic Acid Alternating Co-polysaccharides Prepared from TEMPO-Oxidized Native Celluloses by Surface Peeling (pages 7670–7672)

      Masayuki Hirota, Dr. Kazuo Furihata, Dr. Tsuguyuki Saito, Prof. Toshinari Kawada and Prof. Akira Isogai

      Version of Record online: 13 SEP 2010 | DOI: 10.1002/anie.201003848

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      Two native celluloses with different nanofibril widths and crystallinity were subjected to TEMPO-mediated oxidation. Constant-time heteronuclear multiple-bond correlation analysis of the water-soluble products and subsequent surface peeling revealed that more than 90 % of the products were (1[RIGHTWARDS ARROW]4)-β-linked glucose/glucuronic acid (Glc/GluA) alternating copolysaccharides (see scheme; TEMPO=2,2,6,6-tetramethylpiperidin-1-yloxyl).

    4. Molecular Dynamics

      Multiple Routes to Characterize the Folding of a Small DNA Hairpin (pages 7673–7676)

      Guillem Portella and Modesto Orozco

      Version of Record online: 15 SEP 2010 | DOI: 10.1002/anie.201003816

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      DNA perming: Folding of a small DNA hairpin from an extended conformation follows two main folding pathways: direct folding (green arrows) and de-trapping from non-native compact structures (red arrows). (Also shown: guanosine 5′G anti form.)

    5. Molecular Highlighters

      A New Strategy to Photoactivate Green Fluorescent Protein (pages 7677–7679)

      Dr. Dan Groff, Dr. Feng Wang, Dr. Steffen Jockusch, Prof. Nicholas J. Turro and Prof. Peter G. Schultz

      Version of Record online: 10 SEP 2010 | DOI: 10.1002/anie.201003797

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      A bright idea: A photoactivatable GFP variant has been developed by mutagenesis of the fluorophore tyrosine to a photocaged o-nitrobenzyl tyrosine. This protein is practically nonfluorescent until exposed to 365 nm light, which increases fluorescence nearly 100-fold. The quenching mechanism as suggested by crystallography and time-resolved UV/Vis spectroscopy is most likely due to photon-induced electron transfer to the nitrobenzyl group.

    6. Functional Supramolecular Systems

      A Chiral and Colorful Redox Switch: Enhanced π Acidity in Action (pages 7680–7683)

      Dr. Jiří Míšek, Andreas Vargas Jentzsch, Dr. Shin-ichiro Sakurai, Daniel Emery, Dr. Jiri Mareda and Prof. Stefan Matile

      Version of Record online: 13 SEP 2010 | DOI: 10.1002/anie.201003722

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      Deep blue diving: π Acidities up to a new record of −4.74 eV are made possible with simple sulfur redox chemistry (see scheme). This attractive method is able to generate exceptional electron affinities and anion transport efficiencies for applications in optoelectronic devices, medicinal chemistry, and anion–π catalysis.

    7. Perovskites

      Structural Diversity in Non-Layered Hybrid Perovskites of the RMCl3 Family (pages 7684–7687)

      Lucy A. Paton and Dr. William T. A. Harrison

      Version of Record online: 6 SEP 2010 | DOI: 10.1002/anie.201003541

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      A novel family: Besides thousands of metal oxide perovskites (simplest formula ABO3) layered hybrid perovskites exist, in which slabs of vertex-sharing metal halide octahedra are separated by organic cations. Here, a “missing link” between these two families is described: nonlayered hybrid perovskite networks containing both inorganic (alkali metal and chloride ions) and organic constituents (see, for example, C4H12N2⋅KCl3⋅H2O; KCl6 octahedra lilac, Cl green, C dark gray, N blue, O red).

    8. Nanotube Self-Assembly

      Amphiphilic Self-Assembly of an n-Type Nanotube (pages 7688–7691)

      Hui Shao, James Seifert, Natalie C. Romano, Min Gao, Jonathan J. Helmus, Prof. Christopher P. Jaroniec, Prof. David A. Modarelli and Prof. Jon R. Parquette

      Version of Record online: 6 SEP 2010 | DOI: 10.1002/anie.201003415

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      Mmm—stacks of donuts! A one-dimensional n-type nanotube was formed by stacking rings formed from the bolaamphiphilic self-assembly of 1,4,5,8-naphthalenetetracarboxylic acid diimide (NDI) with L-lysine headgroups (see picture). Solid-state NMR studies demonstrate the exceptional conformational homogeneity of the constituent molecules that make up the nanotubes.

    9. Marine Chemistry

      Electrical Current Generation across a Black Smoker Chimney (pages 7692–7694)

      Dr. Ryuhei Nakamura, Toshihiro Takashima, Dr. Souichiro Kato, Dr. Ken Takai, Dr. Masahiro Yamamoto and Prof. Dr. Kazuhito Hashimoto

      Version of Record online: 13 SEP 2010 | DOI: 10.1002/anie.201003311

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      Some like it hot: Metal-like electrical conduction and electrocatalytic function of a black smoker chimney point to a possible new form of energy transfer from hot, reductive hydrothermal fluid to cold, oxygenated seawater by electrical current generation in the sulfide chimney wall.

    10. Molecular Gelators

      Sugar-Derived Phase-Selective Molecular Gelators as Model Solidifiers for Oil Spills (pages 7695–7698)

      Swapnil R. Jadhav, Dr. Praveen Kumar Vemula, Rakesh Kumar, Prof. Srinivasa R. Raghavan and Prof. George John

      Version of Record online: 15 JUL 2010 | DOI: 10.1002/anie.201002095

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      Mopping up: Phase-selective gelators were synthesized from sugar alcohols using biocatalysis. The gelators exhibited an unprecedented ability to phase-selectively gel only organic liquids including crude-oil fractions in the presence of water at room temperature. Oil can be recovered from the gelled phase by heating and distillation. Thus this class of materials may be useful in recovering oil from spills.

    11. Perovskite Phases

      Trends in Stability of Perovskite Oxides (pages 7699–7701)

      Federico Calle-Vallejo, Dr. José I. Martínez, Dr. Juan M. García-Lastra, Prof. Mogens Mogensen and Prof. Jan Rossmeisl

      Version of Record online: 10 SEP 2010 | DOI: 10.1002/anie.201002301

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      Trends in formation energiesequation image of 41 perovskites AMO3 at 298 K are reproduced by equation image from DFT calculations with the RPBE-GGA functional (see picture; A green, M blue, O red). Moreover, the calculations rationalize systematic trends in their properties, reveal a direct connection between composition and stability in perovskites, and open up a path to ab initio constructions of complete phase diagrams.

    12. Polyoxometalate Hybrids

      Terbium Polyoxometalate Organic Complexes: Correlation of Structure with Luminescence Properties (pages 7702–7705)

      Dr. Chris Ritchie, Dr. Evan G. Moore, Dr. Manfred Speldrich, Prof. Dr. Paul Kögerler and Dr. Colette Boskovic

      Version of Record online: 10 SEP 2010 | DOI: 10.1002/anie.201002320

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      Light up the POMs: A luminescent lanthanoid complex with polyoxometalate (POM) and organic ligands has been structurally characterized (see picture). Comparison of this octanuclear TbIII complex of 2-picolinate and tungstoarsenate ligands with a dinuclear relative reveals the role of the organic ligands as chromophores, identifies the luminescent Tb centers, and determines the relationship between POM coordination mode and luminescence quenching.

    13. Cell Migration

      You have full text access to this OnlineOpen article
      An Inhibitor of a Cell Adhesion Receptor Stimulates Cell Migration (pages 7706–7709)

      Dr. Shagufta H. Shabbir, Dr. Jessica L. Eisenberg and Prof. Milan Mrksich

      Version of Record online: 9 SEP 2010 | DOI: 10.1002/anie.201002699

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      Making cells get a move on: The integrins are cell-surface receptors that mediate the adhesion and migration of cells on a protein matrix. An open question is whether addition of an inhibitor of the receptor slows or accelerates cell migration. By using self-assembled monolayers presenting a cell adhesion ligand as a model system it is found that an inhibitor (RGD peptide) can stimulate cell migration.

    14. Molecular Recognition

      Discrimination between Hard Metals with Soft Ligand Donor Atoms: An On-Fluorescence Probe for Manganese(II) (pages 7710–7713)

      Jian Liang and Prof. Dr. James W. Canary

      Version of Record online: 6 SEP 2010 | DOI: 10.1002/anie.201002853

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      A backwards strategy for achieving Mn2+/Ca2+ selectivity was demonstrated: Instead of optimizing binding of Mn2+, the bapta ligand (upper structure in scheme) was modified by changing O to N donors to discourage association by unwanted competitor Ca2+. Attachment of a fluorophore gave a Mn2+-selective on-fluorescent probe for use in live cell imaging.

    15. π-Conjugated Polymers

      Tuning the Singlet–Triplet Gap in Metal-Free Phosphorescent π-Conjugated Polymers (pages 7714–7717)

      Dr. Debangshu Chaudhuri, Dr. Henning Wettach, Kipp J. van Schooten, Su Liu, Eva Sigmund, Prof. Dr. Sigurd Höger and Prof. Dr. John M. Lupton

      Version of Record online: 10 SEP 2010 | DOI: 10.1002/anie.201003291

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      Glow in the dark: A tunable singlet–triplet exchange gap arises in optically active conjugated polymers that exhibit both strong fluorescence from the singlet state and pronounced phosphorescence from triplet excitations (see picture). The polymers were incorporated into organic light-emitting diodes (OLEDs).

    16. Organometallic Hollow Spheres

      Organometallic Hollow Spheres Bearing Bis(N-Heterocyclic Carbene)–Palladium Species: Catalytic Application in Three-Component Strecker Reactions (pages 7718–7722)

      Jaewon Choi, Hye Yun Yang, Dr. Hae Jin Kim and Prof. Seung Uk Son

      Version of Record online: 10 SEP 2010 | DOI: 10.1002/anie.201003101

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      Hollow-sphere catalysts were prepared by means of 3D network formation between a tetraimidazolium building block and palladium acetate. The bis(N-heterocyclic carbene)–palladium species that were concomitantly formed during growth of the hollow spheres showed excellent activity as heterogeneous catalysts in one-pot three-component Strecker reactions of ketones (see picture; TMS=trimethylsilyl).

    17. Perovskites

      (In1−yMny)MnO3 (1/9≤y≤1/3): Unusual Perovskites with Unusual Properties (pages 7723–7727)

      Dr. Alexei A. Belik, Dr. Yoshitaka Matsushita, Dr. Masahiko Tanaka and Prof. Eiji Takayama-Muromachi

      Version of Record online: 6 SEP 2010 | DOI: 10.1002/anie.201003080

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      More Mn: New perovskite oxides (In1−yMny)MnO3 (1/9≤y≤1/3, see picture) were prepared by using a high-pressure technique. The A site is doped with Mn2+ ions, and (In1−yMny)MnO3 is similar to (Lu1−yCay)MnO3. The B-site-ordered structure is realized through the ordering of Mn3+ and Mn4+ ions. Materials with y≤0.25 demonstrate spin-glass-like properties, while (In2/3Mn1/3)MnO3 shows magnetic properties typical for canted antiferromagnets.

    18. Molecular Electronics

      Dinaphthopentalenes: Pentalene Derivatives for Organic Thin-Film Transistors (pages 7728–7732)

      Prof. Takeshi Kawase, Takeru Fujiwara, Prof. Chitoshi Kitamura, Akihito Konishi, Dr. Yasukazu Hirao, Dr. Kouzou Matsumoto, Prof. Hiroyuki Kurata, Prof. Takashi Kubo, Shoji Shinamura, Hiroki Mori, Dr. Eigo Miyazaki and Prof. Kazuo Takimiya

      Version of Record online: 10 SEP 2010 | DOI: 10.1002/anie.201003609

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      Extended π system: A nickel(0)-mediated reaction afforded dinaphthopentalene derivatives, whose electronic and electrochemical properties depend on the fusion patterns. Very high hole mobility was observed for an amorphous material, and the compounds are applicable to organic heterojunction photovoltaic cells (see picture).

    19. Coupling Reactions

      Synthesis of Aryl Ketones by Palladium(II)-Catalyzed Decarboxylative Addition of Benzoic Acids to Nitriles (pages 7733–7737)

      Jonas Lindh, Dr. Per J. R. Sjöberg and Prof. Mats Larhed

      Version of Record online: 13 SEP 2010 | DOI: 10.1002/anie.201003009

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      An efficient, sustainable method for the preparation of aryl ketones from ortho-substituted benzoic acids proceeds through their decarboxylation to generate an aryl–palladium species, followed by addition to a nitrile and hydrolysis of the intermediate ketimine.

    20. Homogeneous Catalysis

      Continuous Rhodium-Catalyzed Hydroformylation of 1-Octene with Polyhedral Oligomeric Silsesquioxanes (POSS) Enlarged Triphenylphosphine (pages 7738–7741)

      Dr. Michèle Janssen, Dr. Jos Wilting, Dr. Christian Müller and Prof. Dieter Vogt

      Version of Record online: 8 SEP 2010 | DOI: 10.1002/anie.201001926

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      Go with the flow: Homogeneous catalyst recycling can be applied to the production of aldehydes in a continuous flow nanofiltration reactor (see picture) that can operate for an unprecedented period of up to two weeks without showing typical deactivation or leaching phenomena. The catalyst is based on a bulky, rigid, and robust silsesquioxane-modified PPh3 ligand, and combines efficient recovery with high activity and selectivity.

    21. Enantioseparation

      Strong Detrimental Effect of a Minute Enantiomeric Impurity of a Chiral Selector on the Enantioselectivity Factor (pages 7742–7744)

      Dr. Pavel A. Levkin, Dr. Norbert M. Maier, Prof. Dr. Volker Schurig and Prof. Dr. Wolfgang Lindner

      Version of Record online: 6 SEP 2010 | DOI: 10.1002/anie.201002215

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      Without a trace? The higher the enantioselectivity of a chiral selector, the more it is sensitive to enantiomeric impurities. Therefore, the enantiomeric purity of a chiral selector affects the enantioseparation factor α (see picture).

    22. Water Oxidation

      The cis-[RuII(bpy)2(H2O)2]2+ Water-Oxidation Catalyst Revisited (pages 7745–7747)

      Dr. Xavier Sala, Mehmed Z. Ertem, Dr. Laura Vigara, Dr. Tanya K. Todorova, Dr. Weizhong Chen, Dr. Reginaldo C. Rocha, Dr. Francesco Aquilante, Prof. Christopher J. Cramer, Prof. Laura Gagliardi and Prof. Antoni Llobet

      Version of Record online: 6 SEP 2010 | DOI: 10.1002/anie.201002398

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      The only operating mechanism in the oxidation of water to dioxygen catalyzed by the mononuclear cis-[RuII(bpy)2(H2O)2]2+ complex when treated with excess CeIV was unambiguously established. Theoretical calculations together with 18O-labeling experiments (see plot) revealed that it is the nucleophilic attack of water on a Ru[BOND]O group.

    23. Monodisperse Particles

      Surface-Tension-Induced Synthesis of Complex Particles Using Confined Polymeric Fluids (pages 7748–7752)

      Chang-Hyung Choi, Dr. Jinkee Lee, Kisun Yoon, Prof. Anubhav Tripathi, Prof. Howard A. Stone, Prof. David A. Weitz and Prof. Chang-Soo Lee

      Version of Record online: 2 SEP 2010 | DOI: 10.1002/anie.201002764

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      Resolving the tension: Complex particles with various shapes such as bullets, cylinders, discs, hearts, hexagons, and Janus particles can be synthesized by two different surface-tension-induced flow sequences (A and B; see picture, scale bars=100 μm). The particles produced by using this approach can be exploited as anisotropic building blocks for the fabrication of complex systems by combination of the two sequences.

    24. Asymmetric Catalysis

      Stereocontrolled Creation of All-Carbon Quaternary Stereocenters by Organocatalytic Conjugate Addition of Oxindoles to Vinyl Sulfone (pages 7753–7756)

      Qiang Zhu and Prof. Dr. Yixin Lu

      Version of Record online: 6 SEP 2010 | DOI: 10.1002/anie.201003837

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      Multifunctional catalysts in operation: A novel class of trifunctional thiourea catalysts containing natural amino acid residues have been prepared (see scheme), and found to be very effective towards the asymmetric addition of 3-alkyl-oxindoles to 1,1-bis(benzenesulfonyl)ethylene. This synthetic protocol has led to the enantioselective synthesis of 3-alkyl-3-aryl-disubstituted oxindoles and indolines with an all-carbon quaternary stereogenic center.

    25. Small-Molecule Activation

      Spontaneous Dihydrogen Activation by Neutral TaO4 Complex at Cryogenic Temperatures (pages 7757–7761)

      Prof. Dr. Mingfei Zhou, Caixia Wang, Prof. Dr. Zhen hua Li, Jia Zhuang, Dr. Yanying Zhao, Prof. Dr. Xuming Zheng and Prof. Dr. Kangnian Fan

      Version of Record online: 10 SEP 2010 | DOI: 10.1002/anie.201003001

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      Get active: Neutral TaO4 d0 complex is able to cleave dihydrogen heterolytically and spontaneously to form [HTaO(OH)(η2-O2)] in solid argon at cryogenic temperatures. Theoretical calculations predict that the hydrogen atoms in [HTaO(OH)(η2-O2)] can easily be transferred to organic compounds. Thus, TaO4 can serve as a model catalyst for hydrogenation reactions.

    26. Synthetic Methods

      Acceleration of the Substitution of Silanes with Grignard Reagents by Using either LiCl or YCl3/MeLi (pages 7762–7764)

      Naoki Hirone, Hiroaki Sanjiki, Dr. Ryoichi Tanaka, Dr. Takeshi Hata and Prof. Dr. Hirokazu Urabe

      Version of Record online: 6 SEP 2010 | DOI: 10.1002/anie.201003174

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      Getting up to speed: Both LiCl and the YCl3/MeLi catalyst system have an acceleration effect upon the substitution of silanes using Grignard reagents (see scheme). The method provides access to benzyl-, allyl-, and arylsilanes in good yields from the starting silanes.

    27. Bioorganic Replication

      Morphology-Preserving Conversion of a 3D Bioorganic Template into a Nanocrystalline Multicomponent Oxide Compound (pages 7765–7768)

      Jonathan P. Vernon, Dr. Yunnan Fang, Dr. Ye Cai and Prof. Dr. Kenneth H. Sandhage

      Version of Record online: 8 SEP 2010 | DOI: 10.1002/anie.201003170

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      Chitinous wing scales of Morpho helenor butterflies were converted into BaTiO3 replicas through the use of a layer-by-layer surface sol-gel process, organic pyrolysis, and a microwave hydrothermal reaction (see picture). This general structure-preserving process may be used to convert microscale nanostructured bioorganic or synthetic organic templates into a variety of functional multicomponent oxides.

    28. Asymmetric Catalysis

      Rhodium-Catalyzed Asymmetric 1,4-Addition of Aryl Alanes to Trisubstituted Enones: Binap as an Effective Ligand in the Formation of Quaternary Stereocenters (pages 7769–7772)

      Dr. Christine Hawner, Daniel Müller, Ludovic Gremaud, Abdellah Felouat, Prof. Simon Woodward and Prof. Alexandre Alexakis

      Version of Record online: 6 SEP 2010 | DOI: 10.1002/anie.201003300

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      All for one and 1,4-all: Readily available aryl alanes are used in the rhodium-catalyzed asymmetric conjugate addition reaction with a variety of cyclic and acyclic enones. The enhanced reactivity of the system allows the use of the common binap ligand for the generation of quaternary benzylic stereocenters in excellent enantioselectivity (see scheme).

    29. Prussian Blue Materials

      Anomalous Stoichiometry, Layered Structure, and Magnetic Ordering for the Prussian Blue Analogue [NEt4]2[MnII3(CN)8] (pages 7773–7775)

      Dr. Jae-Hyuk Her, Prof. Peter W. Stephens, Christopher M. Kareis, Dr. Joshua G. Moore and Prof. Joel S. Miller

      Version of Record online: 8 OCT 2010 | DOI: 10.1002/anie.201003381

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      Unprecedented: Atypical of Prussian blue structured materials, MnII and [NEt4]CN react to form [NEt4]2Mn3(CN)8 possessing layers of octahedral [MnII(CN)6]4− bonded to two high-spin tetrahedral MnII sites (see structure; yellow and red Mn, black C, blue N).

    30. Solid Acids

      Increasing the Brønsted Acidity of Flame-Derived Silica/Alumina up to Zeolitic Strength (pages 7776–7781)

      Dr. Jun Huang, Niels van Vegten, Dr. Yijiao Jiang, Prof. Dr. Michael Hunger and Prof. Dr. Alfons Baiker

      Version of Record online: 6 SEP 2010 | DOI: 10.1002/anie.201003391

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      Feel the burn: Silica/alumina was prepared in milliseconds by flame-spray pyrolysis (see picture) with a homogeneous composition and at super-high calcination temperatures. This solid acid has tunable acidity ranging from weak or moderate to strong Brønsted acidity. This unique property makes this material versatile for desired industrial applications.

    31. Photochemistry

      Enantioselective Lewis Acid Catalysis in Intramolecular [2+2] Photocycloaddition Reactions of Coumarins (pages 7782–7785)

      Dr. Hao Guo, Dr. Eberhardt Herdtweck and Prof. Dr. Thorsten Bach

      Version of Record online: 10 SEP 2010 | DOI: 10.1002/anie.201003619

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      Photochemistry goes acidic! In the presence of the chiral Lewis acid catalyst 2 the intramolecular [2+2] photocycloaddition of 4-(alk-4-enyl)coumarins (1) provides the corresponding products 3 with up to four stereogenic centers in a highly chemo- (84–89 % yield) and stereoselective fashion. For R=H, enantioselectivities up to 82 % ee are possible with 50 mol % catalyst 2 and up to 78 % ee with only 20 mol % of catalyst 2.

    32. Nanocatalysis

      Asymmetric Nanocatalysis: N-Heterocyclic Carbenes as Chiral Modifiers of Fe3O4/Pd nanoparticles (pages 7786–7789)

      Dr. Kalluri V. S. Ranganath, Dr. Johannes Kloesges, Dr. Andreas H. Schäfer and Prof. Dr. Frank Glorius

      Version of Record online: 15 SEP 2010 | DOI: 10.1002/anie.201002782

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      Superficial success: A chiral N-heterocyclic carbene (NHC*) is used to modify Fe3O4/Pd nanoparticles, which then catalyze asymmetric α-arylations. This successful synthesis of a heterogeneous catalyst and its appliation in asymmetric catalysis is in stark contrast to the simple immobilization of an established chiral homogeneous catalyst.

    33. Heterocycles

      Efficient Synthesis of Pyrazoles: Oxidative C[BOND]C/N[BOND]N Bond-Formation Cascade (pages 7790–7794)

      Dr. Julia J. Neumann, Mamta Suri and Prof. Dr. Frank Glorius

      Version of Record online: 6 SEP 2010 | DOI: 10.1002/anie.201002389

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      Golden section: A novel synthetic strategy for the synthesis of tetrasubstituted pyrazoles is provided. In an efficient C[BOND]C/N[BOND]N bond-formation cascade, enamines and nitriles are oxidatively coupled to deliver pyrazoles in good yields (see scheme). The ready availability of the starting materials, the high level of practicability of the reaction and work up, and the avoidance of hydrazine starting materials make the method attractive.

    34. Organocalcium Chemistry

      Insertion of Pyridine into the Calcium Allyl Bond: Regioselective 1,4-Dihydropyridine Formation and C[BOND]H Bond Activation (pages 7795–7798)

      Phillip Jochmann, Thomas S. Dols, Dr. Thomas P. Spaniol, Dr. Lionel Perrin, Prof. Dr. Laurent Maron and Prof. Dr. Jun Okuda

      Version of Record online: 10 SEP 2010 | DOI: 10.1002/anie.201003704

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      The remarkable balance between nucleophilicity and basicity that is found for bis(allyl)calcium has not been previously reported for organolithium and organomagnesium reagents. Pyridine undergoes regioselective 1,4-insertion into the calcium allyl bond of bis(allyl)calcium. The resulting calcium 4-allyl-1,4-dihydropyridyl compound can be readily converted into the N-protected 1,4-dihydropyridine derivatives.

    35. Homochirality

      Circular Dichroism of Amino Acids in the Vacuum-Ultraviolet Region (pages 7799–7802)

      Prof. Dr. Uwe J. Meierhenrich, Dr. Jean-Jacques Filippi, Cornelia Meinert, Dr. Jan Hendrik Bredehöft, Dr. Jun-ichi Takahashi, Dr. Laurent Nahon, Dr. Nykola C. Jones and Dr. Søren V. Hoffmann

      Version of Record online: 15 SEP 2010 | DOI: 10.1002/anie.201003877

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      Extending CD spectroscopy: Strong circular dichroic (CD) transitions in amino acids were observed when CD spectroscopy was extended to the vacuum-ultraviolet spectral range between 140 and 190 nm (see picture). Here, proteinogenic amino acids show the same CD magnitude and the same sign, and circularly polarized light is thus capable of inducing enantiomeric excesses of the same handedness. Interestingly, typical “meteoritic” amino acids have different CD properties.

    36. NMR Spectroscopy

      Dynamic Nuclear Polarization of Deuterated Proteins (pages 7803–7806)

      Dr. Ümit Akbey, Dr. W. Trent Franks, Arne Linden, Sascha Lange, Prof. Robert G. Griffin, Dr. Barth-Jan van Rossum and Prof. Hartmut Oschkinat

      Version of Record online: 19 AUG 2010 | DOI: 10.1002/anie.201002044

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      For D's a jolly good fellow: Deuteration of proteins significantly increases the signal enhancements observed in dynamic nuclear polarization (DNP) magic-angle spinning (MAS) NMR experiments. In 13C CP-MAS spectra an enhancement of 120 is observed for perdeuterated SH3 with an exchangeable proton ratio of 50 %, whereas the enhancement is only 31 for the fully protonated SH3. The direct 13C excitation of the perdeuterated sample increases the enhancement to 148.

    37. Noble Metalates

      A Noble-Metalate Bowl: The Polyoxo-6-vanado(V)-7-palladate(II) [Pd7V6O24(OH)2]6− (pages 7807–7811)

      Dr. Natalya V. Izarova, Dr. Nina Vankova, Abhishek Banerjee, Prof. Dr. Geoffrey B. Jameson, Prof. Dr. Thomas Heine, Florian Schinle, Priv.-Doz. Dr. Oliver Hampe and Prof. Dr. Ulrich Kortz

      Version of Record online: 13 SEP 2010 | DOI: 10.1002/anie.201001738

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      Nobly born: The bowl-shaped noble metalate [PdII7VV6O24(OH)2]6−(Pd7V6) comprises seven square-planar PdIIO4 units as well as four tetrahedral VVO4 and two square-pyramidal VVO5 addenda units (see picture). The solution stability of Pd7V6 has been demonstrated by 51V NMR spectroscopy, ESI mass spectrometry, and DFT calculations.

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