Angewandte Chemie International Edition

Cover image for Vol. 49 Issue 27

June 21, 2010

Volume 49, Issue 27

Pages 4515–4685

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Highlights
    8. Review
    9. Communications
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    1. Cover Picture: Electrons as “Invisible Ink”: Fabrication of Nanostructures by Local Electron Beam Induced Activation of SiOx (Angew. Chem. Int. Ed. 27/2010) (page 4515)

      Marie-Madeleine Walz, Michael Schirmer, Florian Vollnhals, Thomas Lukasczyk, Hans-Peter Steinrück and Hubertus Marbach

      Version of Record online: 8 JUN 2010 | DOI: 10.1002/anie.201002482

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      Electrons as Invisible Ink A SiOx surface can be locally activated with a focused electron beam (1) such that subsequently dosed [Fe(CO)5] decomposes (2) and autocatalytically grows to pure Fe nanocrystals (3) at predefined positions until the precursor supply is stopped. In their Communication on page 4669 ff., H. Marbach et al. describe how the two-step process might be the starting point of a novel way to generate nanostructures (see the 3D representation of the SEM data in the background).

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Highlights
    8. Review
    9. Communications
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    1. Inside Cover: Colloidal Synthesis of Non-Equilibrium Wurtzite-Type MnSe (Angew. Chem. Int. Ed. 27/2010) (page 4516)

      Ian T. Sines, Rajiv Misra, Peter Schiffer and Raymond E. Schaak

      Version of Record online: 10 JUN 2010 | DOI: 10.1002/anie.201003242

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      The elusive wurtzite polymorph of MnSe, the end member of the magnetic solid semiconductor solution Zn1-xMnxSe, was synthesized for the first time as colloidal nanoparticles. In their Communication on page 4638 ff., R. E. Schaak et al. describe the chemical low-temperature synthesis of this previously unknown compound in high yields. The material has an optical bandgap of 3.5–3.8 eV, and there are indications of antiferromagnetic ordering at 64 K.

  3. Graphical Abstract

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

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Highlights
    8. Review
    9. Communications
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    1. Gerhard Erker (pages 4536–4538)

      Version of Record online: 8 JUN 2010 | DOI: 10.1002/anie.201000969

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      “When I was eighteen I wanted to be either a chemist or a paleontologist. My favorite piece of research is the development of stereochemistry …” This and more about Gerhard Erker can be found on page 4536–4538.

  6. Highlights

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Highlights
    8. Review
    9. Communications
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    1. Raman Microscopy

      A Spectral Window to the Cell (pages 4540–4541)

      Peter Hildebrandt

      Version of Record online: 27 MAY 2010 | DOI: 10.1002/anie.201001616

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      A view of the room: A novel application of Raman microscopy takes advantage of a spectral window to map the uptake and distribution of metal-carbonyl-based drugs in single cells. The approach provides information on cell structure and molecular structure simultaneously and may have significant impact on drug screening and on the analysis of cellular processes in general.

    2. Structure Hierarchy

      From Fluidic Self-Assembly to Hierarchical Structures—Superhydrophobic Flexible Interfaces (pages 4542–4543)

      Ulrich Jonas and Maria Vamvakaki

      Version of Record online: 27 MAY 2010 | DOI: 10.1002/anie.201001494

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      Two-faced: Through the combination of complex structural hierarchy and chemical diversity, amphiphilic Janus particles with a superhydrophobic and a hydrophilic hemisphere self-assemble at the air–water interface to form highly flexible and impregnable water-repelling layers. These layers of Janus particles have fascinating properties: for example, water droplets can rest on top of such a layer floating on water (see picture).

  7. Review

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Highlights
    8. Review
    9. Communications
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    1. Porous Materials

      Nanoporous Metal Foams (pages 4544–4565)

      Bryce C. Tappan, Stephen A. Steiner III and Erik P. Luther

      Version of Record online: 31 MAY 2010 | DOI: 10.1002/anie.200902994

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      The holey grail of metallic materials: Synthetic pathways for preparing nanoporous metals foams have recently been demonstrated, opening a new frontier of high-surface-area catalysts and conductive materials. The scope and potential of techniques for preparing nanoporous metal foams are assessed with a focus on combustion synthesis employing metal bistetrazolamine complexes.

  8. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Highlights
    8. Review
    9. Communications
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    1. C[BOND]O Bond Activation

      Direct Application of Phenolic Salts to Nickel-Catalyzed Cross-Coupling Reactions with Aryl Grignard Reagents (pages 4566–4570)

      Da-Gang Yu, Bi-Jie Li, Shu-Fang Zheng, Bing-Tao Guan, Bi-Qing Wang and Zhang-Jie Shi

      Version of Record online: 14 APR 2010 | DOI: 10.1002/anie.200907359

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      You're nickel'd pal! The first successful coupling reaction with the direct application of naphtholates as electrophiles (see scheme, X=halide) improves both the step economy and atom economy of cross-coupling reactions whilst decreasing the cost of preparing complex scaffolds from readily available phenol derivatives.

    2. Infochemistry

      Long-Duration Transmission of Information with Infofuses (pages 4571–4575)

      Choongik Kim, Samuel W. Thomas III and George M. Whitesides

      Version of Record online: 18 MAY 2010 | DOI: 10.1002/anie.201001582

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      Infofuse” for long: “Infofuses”—chemically based systems for non-electronic communication that can transmit alphanumeric information encoded as pulses of light (see picture)—can now operate for hours without extinction. These characteristics improve their potential for a new approach to information technology that combines chemistry and information—“infochemistry”.

    3. Cation Sensors

      Selective Detection of Iron(III) by Rhodamine-Modified Fe3O4 Nanoparticles (pages 4576–4579)

      Baodui Wang, Jun Hai, Zengchen Liu, Qin Wang, Zhengyin Yang and Shouheng Sun

      Version of Record online: 20 MAY 2010 | DOI: 10.1002/anie.201001373

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      Rh-odin's masterpiece: Coupling N-(rhodamine-6G)lactam-ethylenediamine to Fe3O4 nanoparticles through a polyethylene glycol chain renders the rhodamine unit more water soluble and useful for sensitive and selective detection of FeIII at the 2 ppb level in water. This sensitivity is also demonstrated in HeLa cells, thus indicating potential applications of this detection method in biological systems.

    4. Structure–Activity Relationship

      Molecular Modeling, Total Synthesis, and Biological Evaluations of C9-Deoxy Bryostatin 1 (pages 4580–4584)

      Gary E. Keck, Yam B. Poudel, Arnab Rudra, Jeffrey C. Stephens, Noemi Kedei, Nancy E. Lewin, Megan L. Peach and Peter M. Blumberg

      Version of Record online: 20 MAY 2010 | DOI: 10.1002/anie.201001200

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      ‘OH’ no you don't: The title compound 1 has been synthesized and evaluated for biological function. Molecular modeling of bryostatin 1 with the C1 domain of protein kinase C  δ indicates that the C9[BOND]OH of bryostatin 1 makes a hydrogen-bonding contact to the protein. Despite the absence of the hydrogen-bonding contact for 1, it displays bryostatin-like biological effects in four assays using either U937 leukemia cells or prostate LNCaP cells.

    5. Zeolites

      A Rational Approach to the Ionothermal Synthesis of an AlPO4 Molecular Sieve with an LTA-Type Framework (pages 4585–4588)

      Elie J. Fayad, Nicolas Bats, Christine E. A. Kirschhock, Bernadette Rebours, Anne-Agathe Quoineaud and Johan A. Martens

      Version of Record online: 17 MAY 2010 | DOI: 10.1002/anie.201000304

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      Structurally sound: The synthesis of AlPO4-LTA zeolite in ionic liquids employs 1-benzyl-3-methylimidazolium, tetramethylammonium, and fluoride ions for structuring α cages, sodalite cages, and cubes (see picture; C gray, N blue, O red, Al and P purple, F green). Selective removal of 1-benzyl-3-methylimidazolium ions results in a stable AlPO4-LTA molecular sieve. The α cages of AlPO4-LTA framework can be evacuated while maintaining structural integrity.

    6. DNA-Programmed Assembly

      Establishing the Design Rules for DNA-Mediated Programmable Colloidal Crystallization (pages 4589–4592)

      Robert J. Macfarlane, Matthew R. Jones, Andrew J. Senesi, Kaylie L. Young, Byeongdu Lee, Jinsong Wu and Chad A. Mirkin

      Version of Record online: 18 MAY 2010 | DOI: 10.1002/anie.201000633

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      DNA-programmable colloidal crystals are assembled with 5–80 nm nanoparticles, and the lattice parameters of the resulting crystals vary from 25 to 225 nm. A predictable and mathematically definable relationship between particle size and DNA length dictates the assembly and crystallization processes, creating a set of design rules for DNA-based nanoscale assembly.

    7. Germacyclic Compounds

      Synthesis and Characterization of Two of the Three Isomers of a Germanium-Substituted Bicyclo[2.2.0]hexane Diradicaloid: Stretching the Ge[BOND]Ge Bond (pages 4593–4597)

      Xinping Wang, Yang Peng, Zhongliang Zhu, James C. Fettinger, Philip P. Power, Jingdong Guo and Shigeru Nagase

      Version of Record online: 20 MAY 2010 | DOI: 10.1002/anie.201001086

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      Germane cycles: The inorganic bi- and tricyclohexane derivatives AC provide novel coordination modes of a nitrosoarene to metals. DFT calculations show that A and B correspond to two of three possible stable isomers of the parent diradicaloid that have different Ge[BOND]Ge bond lengths.

    8. Metal–Organic Frameworks

      Thermolabile Groups in Metal–Organic Frameworks: Suppression of Network Interpenetration, Post-Synthetic Cavity Expansion, and Protection of Reactive Functional Groups (pages 4598–4602)

      Rajesh K. Deshpande, Jozeph L. Minnaar and Shane G. Telfer

      Version of Record online: 17 MAY 2010 | DOI: 10.1002/anie.200905960

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      Creating nothing out of something: A bulky tert-butoxycarbonyl group on a biphenyl-4,4′-dicarboxylate ligand suppresses interpenetration to give an open, cubic metal–organic framework. Post-synthetic cleavage of this group by simple thermolysis (see picture) unmasks a potentially reactive amino functional group, increases the void space (yellow sphere), and widens the pore apertures.

    9. Nanostructures

      Noble-Metal-Promoted Three-Dimensional Macroassembly of Single-Layered Graphene Oxide (pages 4603–4607)

      Zhihong Tang, Shuling Shen, Jing Zhuang and Xun Wang

      Version of Record online: 20 MAY 2010 | DOI: 10.1002/anie.201000270

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      Barreling along: 3D macrostructures (cylinder; see picture) have been assembled from single-layered graphene oxide and noble-metal nanocrystals (Au, Ag, Pd, Ir, Rh, Pt, etc.). Although the density of the cylinders is very low (ca. 0.03 g cm−3), they show excellent mechanical properties and have been utilized as a fixed-bed catalyst for the Heck reaction, which proceeded with nearly 100 % selectivity and conversion.

    10. Biosensors

      Multiplexed Detection and Label-Free Quantitation of MicroRNAs Using Arrays of Silicon Photonic Microring Resonators (pages 4608–4611)

      Abraham J. Qavi and Ryan C. Bailey

      Version of Record online: 20 MAY 2010 | DOI: 10.1002/anie.201001712

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      Microrings for microRNAs! A label-free method has been developed for the sensitive detection of microRNAs utilizing arrays of silicon photonic microring resonators. This simple and modularly multiplexable method for the direct profiling of microRNA within 10 minutes meets a number of challenges faced by current methodologies in this area.

    11. Organocatalysis

      Catalytic Asymmetric Reductive Amination of α-Branched Ketones (pages 4612–4614)

      Vijay N. Wakchaure, Jian Zhou, Sebastian Hoffmann and Benjamin List

      Version of Record online: 20 MAY 2010 | DOI: 10.1002/anie.201001715

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      Branching out: An organocatalytic reductive amination of α-branched ketones using dynamic kinetic resolution is reported. The cis-2-substituted cyclohexyl amines were obtained in high diastereoselectivity and enantioselectivity from the corresponding ketones.

    12. Metal–Organic Frameworks

      Open Metal Sites within Isostructural Metal–Organic Frameworks for Differential Recognition of Acetylene and Extraordinarily High Acetylene Storage Capacity at Room Temperature (pages 4615–4618)

      Shengchang Xiang, Wei Zhou, Zhangjing Zhang, Mark A. Green, Yun Liu and Banglin Chen

      Version of Record online: 20 MAY 2010 | DOI: 10.1002/anie.201000094

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      On the metal: Open metal sites within isostructural [M2(DHTP)] metal–organic frameworks (M=Co2+, Mn2+, Mg2+, and Zn2+; DHTP=2,5-dihydroxyterephthalate) exhibit differential molecular recognition with acetylene. The extremely strong interaction of Co2+ with acetylene (see structure) makes [Co2(DHTP)] the highest volumetric acetylene storage material with a capacity of 230 cm3 cm−3 at 295 K and 1 atm.

    13. Homogeneous Catalysis

      Gold-Catalyzed Cycloisomerization Reactions of 2-Tosylaminophenylprop-1-yn-3-ols as a Versatile Approach for Indole Synthesis (pages 4619–4623)

      Prasath Kothandaraman, Weidong Rao, Shi Jia Foo and Philip Wai Hong Chan

      Version of Record online: 17 MAY 2010 | DOI: 10.1002/anie.201000341

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      A great combination: A putative indolyl-substituted vinyl gold species generated in situ from AuCl/AgOTf catalyzed the title transformation. Under these reaction conditions, indenyl-fused and 2,3-disubstituted indole derivatives were produced in good to excellent yields of up to 94 % (see scheme).

    14. Carbocyclization

      Palladium(II)-Catalyzed Oxidative Carbocyclization of Aza-Enallenes (pages 4624–4627)

      Andreas K. Å. Persson and Jan-E. Bäckvall

      Version of Record online: 20 MAY 2010 | DOI: 10.1002/anie.201000726

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      Live and let diene: A palladium(II)-catalyzed oxidative carbocyclization reaction of aza-enallenes provides access to potentially valuable heterocyclic dienes. In the presence of a dieneophile during the carbocyclization step, the products can react further in a one-pot cyclization/Diels–Alder sequence to give polycyclic products. BQ=para-benzoquinone.

    15. Switchable Architectures

      Interconverting Two Classes of Architectures by Reduction of a Self-Sorting Mixture (pages 4628–4632)

      Kumar Parimal, Edward H. Witlicki and Amar H. Flood

      Version of Record online: 20 MAY 2010 | DOI: 10.1002/anie.201001003

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      Two for the price of one: A CuI-based [2]pseudorotaxane ([2]PR+) shows a complete switch in its architectural identity when it transforms into a “grid corner” (G) and back again upon two-electron reduction (see picture; ReB: neutral (red) or reduced ligand (blue); Re: green; Cu: orange; MC: macrocycle).

    16. Chiral indenes

      Gold(I)-Catalyzed Enantioselective Synthesis of Functionalized Indenes (pages 4633–4637)

      Alberto Martínez, Patricia García-García, Manuel A. Fernández-Rodríguez, Félix Rodríguez and Roberto Sanz

      Version of Record online: 17 MAY 2010 | DOI: 10.1002/anie.201001089

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      Can you dig it? An asymmetric synthesis of functionalized 1H-indenes from easily available ortho-(alkynyl)styrene derivatives under mild reaction conditions has been achieved. The reactions proceed through an unprecedented and selective 5-endo-dig gold(I)-catalyzed cycloisomerization or alkoxycyclization, if water or an alcohol is present (see scheme).

    17. Nanoparticles

      Colloidal Synthesis of Non-Equilibrium Wurtzite-Type MnSe (pages 4638–4640)

      Ian T. Sines, Rajiv Misra, Peter Schiffer and Raymond E. Schaak

      Version of Record online: 17 MAY 2010 | DOI: 10.1002/anie.201001213

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      Stabilizing an elusive phase: The wurtzite polymorph of the magnetic semiconductor MnSe, which is also the x=1 end member of the widely studied Zn1−xMnxSe solid solution, was synthesized in high yield for the first time as colloidal nanoparticles using a solution chemistry technique at low temperature (see pictures). Nanoparticles of wurtzite-type MnSe have an optical bandgap of approximately 3.5–3.8 eV and show evidence of antiferromagnetic ordering at 64 K.

    18. Nucleotide Stereochemistry

      Phosphate-Mediated Interconversion of Ribo- and Arabino-Configured Prebiotic Nucleotide Intermediates (pages 4641–4643)

      Matthew W. Powner and John D. Sutherland

      Version of Record online: 20 MAY 2010 | DOI: 10.1002/anie.201001662

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      Flipping stereochemistry: Inorganic phosphate catalyzes the interconversion of ribose and arabinose aminooxazolines, suggesting that the prebiotic synthesis of enantiopure pyrimidine ribonucleotides might have involved a single stereoinversion at C1′ and a double stereoinversion at C2′.

    19. Metal–Organic Frameworks

      Generating Reactive MILs: Isocyanate- and Isothiocyanate-Bearing MILs through Postsynthetic Modification (pages 4644–4648)

      Christophe Volkringer and Seth M. Cohen

      Version of Record online: 17 MAY 2010 | DOI: 10.1002/anie.201001527

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      MILs hold up: Robust aluminum-based metal–organic frameworks (MIL-53(Al)-NH2) can undergo postsynthetic modification with phosgene reagents to produce highly reactive, porous materials bearing isocyanate or isothiocyanate groups (see scheme).

    20. Cycloaddition Reactions

      Nickel-Catalyzed Regioselective [2+2+2] Cycloaddition of Carboryne with Alkynes (pages 4649–4652)

      Zaozao Qiu, Sunewang R. Wang and Zuowei Xie

      Version of Record online: 12 MAY 2010 | DOI: 10.1002/anie.201001249

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      A View [2+2+2] a Kill: For the first time, nickel-catalyzed [2+2+2] cycloaddition reactions of alkynes or diynes with carboryne using 1-iodo-2-lithiocarborane as a precursor have been achieved. The mechanism is proposed after the structural confirmation of the key intermediate, nickelacyclopentene.

    21. RNA Technology

      Posttranscriptional Signal Integration of Engineered Riboswitches Yields Band-Pass Output (pages 4653–4655)

      Norihito Muranaka and Yohei Yokobayashi

      Version of Record online: 17 MAY 2010 | DOI: 10.1002/anie.201001482

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      Light in the middle: A simple band-pass circuit has been designed using only posttranscriptional components in Escherichia coli (see figure). Two engineered riboswitches were used as the chemical sensor and to implement low-pass/high-pass functions. The two signals were integrated by protein complementation using split GFP fragments to achieve a band-pass response.

    22. Organocatalysis

      Organocatalytic Michael Addition of Aldehydes to Protected 2-Amino-1-Nitroethenes: The Practical Syntheses of Oseltamivir (Tamiflu) and Substituted 3-Aminopyrrolidines (pages 4656–4660)

      Shaolin Zhu, Shouyun Yu, You Wang and Dawei Ma

      Version of Record online: 17 MAY 2010 | DOI: 10.1002/anie.201001644

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      Hey Mickey, you're so fine! Organocatalytic Michael additions of aldehydes with protected 2-amino-1-nitroethene could go through three different transition-states to afford adducts with usual and unusual stereochemistry, thereby providing a facile entry to Tamiflu (see scheme) and substituted 3-aminopyrrolidines. TMS=trimethylsilyl, Ac=acetyl.

    23. Carbocyclization

      Electrophilic Cyclization of 1,5-Enynes (pages 4661–4664)

      Benedikt Crone, Stefan F. Kirsch and Klaus-Daniel Umland

      Version of Record online: 17 MAY 2010 | DOI: 10.1002/anie.201001113

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      Valuable six-membered carbocycles including highly substituted benzenes, 1,4-cyclohexadienes, and 4-fluorocyclohexenes can be prepared from simple 1,5-enynes by iodonium-induced cyclization. This cyclization strategy was applied to the total synthesis of cybrodol, a sesquiterpenoid with a pentasubstituted aromatic core (see scheme).

    24. MgCl2-Mediated Additions

      MgCl2-Accelerated Addition of Functionalized Organozinc Reagents to Aldehydes, Ketones, and Carbon Dioxide (pages 4665–4668)

      Albrecht Metzger, Sebastian Bernhardt, Georg Manolikakes and Paul Knochel

      Version of Record online: 17 MAY 2010 | DOI: 10.1002/anie.201000634

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      Pump it up! The sluggish reactivity of organozinc reagents in additions to aldehydes, ketones, and CO2 can be increased by MgCl2, which is usually generated in the preparation of the zinc reagent. The direct reaction with CO2, in particular, opens an expeditious route to phenylacetic acid derivatives, as demonstrated in a short synthesis of ibuprofen (see scheme).

    25. Nanotechnology

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      Electrons as “Invisible Ink”: Fabrication of Nanostructures by Local Electron Beam Induced Activation of SiOx (pages 4669–4673)

      Marie-Madeleine Walz, Michael Schirmer, Florian Vollnhals, Thomas Lukasczyk, Hans-Peter Steinrück and Hubertus Marbach

      Version of Record online: 8 JUN 2010 | DOI: 10.1002/anie.201001308

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      Beam me up: A novel two-step process allows iron nanostructures to be generated locally on SiOx/Si at 300 K. The surface is first locally activated by an electron beam. Then the activated structures are exposed to [Fe(CO)5], which decomposes and grows autocatalytically to give pure Fe nanocrystals.

    26. MicroRNA

      An Aptamer Targeting the Apical-Loop Domain Modulates pri-miRNA Processing (pages 4674–4677)

      Christina E. Lünse, Gracjan Michlewski, Christine S. Hopp, Andrea Rentmeister, Javier F. Cáceres, Michael Famulok and Günter Mayer

      Version of Record online: 8 JUN 2010 | DOI: 10.1002/anie.200906919

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      Gaining maturity: RNA aptamers can serve as specific targeting molecules to modulate the processing of pri-miRNAs. This approach can be used to selectively interfere with microRNA regulation and may open new routes for the development of novel therapies.

    27. Carbenium Ions

      The tert-Butyl Cation in H-Zeolites: Deprotonation to Isobutene and Conversion into Surface Alkoxides (pages 4678–4680)

      Christian Tuma, Torsten Kerber and Joachim Sauer

      Version of Record online: 20 MAY 2010 | DOI: 10.1002/anie.200907015

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      All experimental attempts to identify the tert-butyl carbenium ion in zeolites have been unsuccessful. Calculations with the hybrid MP2:DFT method predict that this ion is less stable than the isomeric surface species isobutene, isobutoxide, and tert-butoxide, but once it has been formed as an intermediate it will survive long enough (59 μs) to be detected by laser spectroscopy (see picture; O red, Si yellow, Al magenta, C green).

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    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Highlights
    8. Review
    9. Communications
    10. Preview
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