Angewandte Chemie International Edition

Cover image for Vol. 50 Issue 48

November 25, 2011

Volume 50, Issue 48

Pages 11263–11539

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Cover Picture: Elemental Sulfur as a Reactive Medium for Gold Nanoparticles and Nanocomposite Materials (Angew. Chem. Int. Ed. 48/2011) (page 11263)

      Dr. Woo Jin Chung, Dr. Adam G. Simmonds, Jared J. Griebel, Eui Tae Kim, Hyo Seon Suh, Prof. In-Bo Shim, Prof. Richard S. Glass, Prof. Douglas A. Loy, Prof. Patrick Theato, Prof. Yung-Eun Sung, Prof. Kookheon Char and Prof. Jeffrey Pyun

      Version of Record online: 28 SEP 2011 | DOI: 10.1002/anie.201106508

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      The direct use of elemental sulfur as a reaction medium for the preparation of Au nanoparticles and vulcanized nanocomposites is described by J. Pyun et al. in their Communication on page 11 409 ff. Liquid sulfur serves multiple functions in this system—as a solvent, reducing agent, and colloidal stabilizer for the preparation of Au colloids. A tremendous excess of elemental sulfur is generated from petroleum refining, which creates new opportunities to use sulfur as a feedstock.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Inside Cover: Direct Arylation of 6-Phenylpurine and 6-Arylpurine Nucleosides by Ruthenium-Catalyzed C[BOND]H Bond Activation (Angew. Chem. Int. Ed. 48/2011) (page 11264)

      Prof. Mahesh K. Lakshman, Dr. Ashoke C. Deb, Dr. Raghu Ram Chamala, Dr. Padmanava Pradhan and Dr. Ramendra Pratap

      Version of Record online: 28 SEP 2011 | DOI: 10.1002/anie.201106047

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      A catalytic cycle involving a ruthenium catalyst leads to the arylation of nucleosides. In their Communication on page 11 400 ff., M. K. Lakshman and co-workers describe C[BOND]H bond activation/arylation of C6 aryl purine 2′-deoxyribonucleosides, wherein a purine nitrogen atom presumably directs the ruthenation. Both aryl iodides and aryl bromides can be used, and the major product results from monoarylation. The cover picture was designed by Satish Lakshman.

  3. Back Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Back Cover: Imidazole-Quartet Water and Proton Dipolar Channels (Angew. Chem. Int. Ed. 48/2011) (page 11540)

      Dr. Yann Le Duc, Dr. Mathieu Michau, Dr. Arnaud Gilles, Valerie Gence, Dr. Yves-Marie Legrand, Dr. Arie van der Lee, Dr. Sophie Tingry and Dr. Mihail Barboiu

      Version of Record online: 26 SEP 2011 | DOI: 10.1002/anie.201106641

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      Dipolar water wires stabilize quartets of ureido imidazole compounds (I quartets). M. Barboiu et al. describe in their Communication on page 11 366 ff. how this stabilization occurs in a manner reminiscent of the stabilization of guanine (G) quartets by cation templating.

  4. Graphical Abstract

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

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Michel R. Gagné (page 11286)

      Version of Record online: 17 OCT 2011 | DOI: 10.1002/anie.201105336

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      “If I won the lottery, I would be able to finally stop writing grants! In my opinion, the word “scientist” means explorer …” This and more about Michel R. Gagné can be found on page 11286.

  7. News

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Hans Wynberg (19222011) (page 11288)

      Ben Feringa and Bert Meijer

      Version of Record online: 28 OCT 2011 | DOI: 10.1002/anie.201107005

  9. Book Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Solvents and Solvent Effects in Organic Chemistry. 4th Ed. By Christian Reichardt and Thomas Welton. (page 11289)

      Ralf Giernoth

      Version of Record online: 13 OCT 2011 | DOI: 10.1002/anie.201105531

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      Wiley-VCH, Weinheim 2010. 718 pp., hardcover, € 159.00.—ISBN 978-3527324736

  10. Highlights

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

      Smart Foams: New Perspectives Towards Responsive Composite Materials (pages 11290–11292)

      Dipl.-Chem. Adrian Carl and Prof.Dr. Regine von Klitzing

      Version of Record online: 28 OCT 2011 | DOI: 10.1002/anie.201105399

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      Hold the foam! Smart foams with a tunable surface-to-volume ratio have numerous potential applications, including decontamination. Recently fatty acid aggregates, the stability of which can be tuned by an external stimulus, were described. The picture shows a plot of the foam volume of a temperature-dependent foam which undergoes supramolecular reorganization.

    2. Amyloid Inhibitors

      Terminating the Amyloid Zipper by Design (pages 11293–11294)

      Prof. Dr. Aphrodite Kapurniotu

      Version of Record online: 4 NOV 2011 | DOI: 10.1002/anie.201105706

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      Zip code: A potentially general, computational design approach has been used to devise peptide inhibitors of protein aggregation into amyloid fibrils. The atomic structures of “steric zippers”, which are formed by short fibril-forming segments of the amyloidogenic proteins, serve as templates. The validity of the approach is demonstrated by the design of inhibitors of amyloid formation associated with Alzheimer's disease pathology and HIV infectivity.

  11. Minireview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Small-Molecule Probes

      Small Molecules from Spiders Used as Chemical Probes (pages 11296–11311)

      Prof. Christian A. Olsen, Prof. Anders S. Kristensen and Prof. Kristian Strømgaard

      Version of Record online: 27 OCT 2011 | DOI: 10.1002/anie.201101599

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      A tangled web: Semiochemicals and acylpolyamine toxins from spiders (see pictures) are unique biological probes and may even be considered potential therapeutic agents. In this Minireview a status update on the research regarding these interesting small molecules is presented.

  12. Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Microwave Chemistry

      Microwave-Assisted Synthesis of Colloidal Inorganic Nanocrystals (pages 11312–11359)

      Dr. Mostafa Baghbanzadeh, Dr. Luigi Carbone, Dr. P. Davide Cozzoli and Prof. Dr. C. Oliver Kappe

      Version of Record online: 4 NOV 2011 | DOI: 10.1002/anie.201101274

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      If you can′t stand the heat, get out of the kitchen: Direct volumetric and efficient heating by microwave irradiation enables the generation of colloidal nanocrystals in a fraction of the time required using conventional heating techniques (see picture). Among the advantages of this non-classical heating method is a great control of reaction temperature, allowing better versatility, reproducibility, and reduced processing times in the fabrication of high-quality nanocrystals.

  13. Communications

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

      Multiple-Interaction Ligands Inspired by Mussel Adhesive Protein: Synthesis of Highly Stable and Biocompatible Nanoparticles (pages 11360–11365)

      Daishun Ling, Wooram Park, Yong Il Park, Nohyun Lee, Fangyuan Li, Changyeong Song, Prof. Su-Geun Yang, Prof. Seung Hong Choi, Prof. Kun Na and Prof. Taeghwan Hyeon

      Version of Record online: 16 SEP 2011 | DOI: 10.1002/anie.201101521

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      All bound up: A poly(L-3,4-dihydroxyphenylalanine)-based ligand converts hydrophobic nanoparticles into hydrophilic and biocompatible species through several binding modes. Nanoparticles functionalized with this ligand (see picture) are highly stable in various aqueous solutions. A successful in vivo MRI application using functionalized Fe3O4 nanoparticles confirmed their suitability for various biomedical applications.

    2. Water Channels

      Imidazole-Quartet Water and Proton Dipolar Channels (pages 11366–11372)

      Dr. Yann Le Duc, Dr. Mathieu Michau, Dr. Arnaud Gilles, Valerie Gence, Dr. Yves-Marie Legrand, Dr. Arie van der Lee, Dr. Sophie Tingry and Dr. Mihail Barboiu

      Version of Record online: 24 AUG 2011 | DOI: 10.1002/anie.201103312

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      Dipolar water wires stabilize quartets of ureido imidazole compounds (I-quartets) in a manner reminiscent of stabilization of guanine (G) quartets by cation templating (see picture).

    3. Natural Products

      Total Synthesis of Tulearin C (pages 11373–11377)

      Dipl.-Chem. Konrad Lehr, Dr. Ronaldo Mariz, Dr. Lucie Leseurre, Barbara Gabor and Prof. Alois Fürstner

      Version of Record online: 11 OCT 2011 | DOI: 10.1002/anie.201106117

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      With the help of the smaller brother: Although alkyne metathesis will always be the little brother of alkene metathesis, it allows problems to be solved that are currently beyond reach of the more famous sibling. This notion is exemplified by the tulearin macrolides, which could only be selectively forged by ring-closing alkyne metathesis (RCAM)/trans reduction using the latest generation of alkyne metathesis catalysts.

    4. Smart Materials

      Water-Enabled Self-Healing of Polyelectrolyte Multilayer Coatings (pages 11378–11381)

      Xu Wang, Feng Liu, Xiwei Zheng and Prof. Junqi Sun

      Version of Record online: 6 OCT 2011 | DOI: 10.1002/anie.201105822

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      Heal thyself! Exponentially grown layer-by-layer-assembled polyelectrolyte multilayer coatings, which are mechanically robust under ambient conditions, can autonomically repair cuts several tens of micrometers deep and wide when they are simply immersed in water or when water is sprayed on the coatings. The self-healing ability originates from the high flowability of these coatings in water.

    5. Helical Structures

      Condensation Approach to Aliphatic Oligourea Foldamers: Helices with N-(Pyrrolidin-2-ylmethyl)ureido Junctions (pages 11382–11385)

      Juliette Fremaux, Dr. Lucile Fischer, Thomas Arbogast, Dr. Brice Kauffmann and Dr. Gilles Guichard

      Version of Record online: 4 OCT 2011 | DOI: 10.1002/anie.201105416

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      Caught in a fold: A simple and efficient coupling strategy to make aliphatic oligourea foldamers is reported. Crystal structures show that the pyrrolidine units (red; see picture) do not impair the 2.5-helical folding of the oligoureas. This modular strategy enables assembly of long helical segments containing non-adjacent pyrrolidine units as exemplified by the synthesis of a helix that is approximately 40 Å long.

    6. Crystal Engineering

      Nanoporous Organic Alloys (pages 11386–11390)

      Dr. Ramalingam Natarajan, Dr. Germinal Magro, Lydia N. Bridgland, Anchalee Sirikulkajorn, Dr. Sampriya Narayanan, Lloyd E. Ryan, Dr. Mairi F. Haddow, Prof. A. Guy Orpen, Dr. Jonathan P. H. Charmant, Dr. Andrew J. Hudson and Prof. Anthony P. Davis

      Version of Record online: 4 OCT 2011 | DOI: 10.1002/anie.201105216

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      Crystal tuning: Organic molecules can be xenophobic, preferring to crystallize with their own kind. Though useful for purification, this precludes the tuning of crystal properties by doping or mixing. Nanoporous steroids provide an exception, as their channels can accept a variety of termini (hexagons and spheres). The steroids can be cocrystallized in any ratio to give a wide range of chiral, potentially porous crystalline materials.

    7. Atom Transfer Radical Polymerization

      Controlled Aqueous Atom Transfer Radical Polymerization with Electrochemical Generation of the Active Catalyst (pages 11391–11394)

      Dr. Nicola Bortolamei, Dr. Abdirisak A. Isse, Dr. Andrew J. D. Magenau, Prof. Armando Gennaro and Prof. Krzysztof Matyjaszewski

      Version of Record online: 16 SEP 2011 | DOI: 10.1002/anie.201105317

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      Enhanced control: Electrochemically mediated atom transfer radical polymerization (ATRP) allows easy modulation of the overall rate and control of polymerization through the variation of an external applied potential, Eapp (see picture). This method has been successfully applied to aqueous ATRP of oligo(ethylene glycol) methyl ether methacrylate (OEOMA475) catalyzed by Cu/tris(2-pyridylmethyl)amine.

    8. Ionic Liquids

      Crystalline Open-Framework Selenidostannates Synthesized in Ionic Liquids (pages 11395–11399)

      Dr. Jian-Rong Li, Zai-Lai Xie, Xiao-Wu He, Dr. Long-Hua Li and Prof. Xiao-Ying Huang

      Version of Record online: 10 OCT 2011 | DOI: 10.1002/anie.201102698

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      Ready to direct: Crystalline selenidostannates were synthesized in imidazolium-based ionic liquids with a small amount of hydrazine monohydrate as additive (see scheme). They are the first open-framework chalcogenides structurally directed by imidazolium cations and are inaccessible by traditional methods.

    9. C[BOND]H Bond Activation

      Direct Arylation of 6-Phenylpurine and 6-Arylpurine Nucleosides by Ruthenium-Catalyzed C[BOND]H Bond Activation (pages 11400–11404)

      Prof. Mahesh K. Lakshman, Dr. Ashoke C. Deb, Dr. Raghu Ram Chamala, Dr. Padmanava Pradhan and Dr. Ramendra Pratap

      Version of Record online: 28 SEP 2011 | DOI: 10.1002/anie.201104035

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      One aryl or two? The title reaction predominantly gives the monoarylation products with various amounts of diarylation product being observed in almost all cases (see scheme). Aryl iodides as well as aryl bromides were reactive under the optimized reaction conditions. The multiple nitrogen atoms in the purine, and oxygen atoms in the saccharide posed no problems in these transformations.

    10. Organic Optical Transistors

      An Organic Optical Transistor Operated under Ambient Conditions (pages 11405–11408)

      Dr. Martti Pärs, Dr. Christiane C. Hofmann, Katja Willinger, Dr. Peter Bauer, Prof. Dr. Mukundan Thelakkat and Prof. Dr. Jürgen Köhler

      Version of Record online: 5 OCT 2011 | DOI: 10.1002/anie.201104193

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      It takes three: The key functionalities of an optical transistor, gating and amplification, are demonstrated exploiting the photophysical properties of a molecular triad (see picture). Two building blocks of the triad are highly efficient fluorophores, whereas the third building block is a photochromic molecule that can be reversibly interconverted between two bistable forms by light.

    11. Sulfur Chemistry

      Elemental Sulfur as a Reactive Medium for Gold Nanoparticles and Nanocomposite Materials (pages 11409–11412)

      Dr. Woo Jin Chung, Dr. Adam G. Simmonds, Jared J. Griebel, Eui Tae Kim, Hyo Seon Suh, Prof. In-Bo Shim, Prof. Richard S. Glass, Prof. Douglas A. Loy, Prof. Patrick Theato, Prof. Yung-Eun Sung, Prof. Kookheon Char and Prof. Jeffrey Pyun

      Version of Record online: 9 SEP 2011 | DOI: 10.1002/anie.201104237

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      Get yellow: The utilization of elemental sulfur as an unconventional medium for the synthesis and stabilization of colloidal gold is reported. In this system, sulfur serves multiple functions to sulfurate PPh3, solubilize and reduce AuI precursors into Au nanoparticles (NPs; see picture). Direct vulcanization of sulfur dispersions of AuNPs afforded cross-linked nanocomposites as confirmed by TEM, XRD, XPS, and Raman spectroscopy.

    12. Proteins

      Exploring the Piezophilic Behavior of Natural Cosolvent Mixtures (pages 11413–11416)

      Martin A. Schroer, Yong Zhai, D. C. Florian Wieland, Christoph J. Sahle, Dr. Julia Nase, Dr. Michael Paulus, Prof. Dr. Metin Tolan and Prof. Dr. Roland Winter

      Version of Record online: 6 OCT 2011 | DOI: 10.1002/anie.201104380

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      Marine organisms have evolved a surprising mechanism to counteract the deleterious effects of urea by trimethylammonium N-oxide (TMAO). The effect of pressure on the structure and intermolecular interactions of lysozyme in urea and TMAO solutions was studied (see picture). These findings help to understand the compensatory effect of urea–TMAO mixtures in deep-sea organisms.

    13. Imaging Agents

      Fluorescent Nanorods and Nanospheres for Real-Time In Vivo Probing of Nanoparticle Shape-Dependent Tumor Penetration (pages 11417–11420)

      Vikash P. Chauhan, Dr. Zoran Popović, Dr. Ou Chen, Jian Cui, Prof. Dr. Dai Fukumura, Prof. Dr. Moungi G. Bawendi and Prof. Dr. Rakesh K. Jain

      Version of Record online: 6 OCT 2011 | DOI: 10.1002/anie.201104449

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      Shape dependent: Fluorescent quantum-dot-based nanospheres and nanorods with identical hydrodynamic size and surface properties but different aspect ratios were developed for real-time in vivo tumor imaging. The nanorods exhibited superior transport and distribution into mammary tumors in vivo versus nanospheres of similar plasma half-life.

    14. Crystal Engineering

      Network Diversity through Decoration of Trigonal-Prismatic Nodes: Two-Step Crystal Engineering of Cationic Metal–Organic Materials (pages 11421–11424)

      Alexander Schoedel, Dr. Lukasz Wojtas, Stephen P. Kelley, Prof. Dr. Robin D. Rogers, Prof. Dr. Mohamed Eddaoudi and Prof. Dr. Michael J. Zaworotko

      Version of Record online: 5 OCT 2011 | DOI: 10.1002/anie.201104688

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      MOMs the word! In a two-step process, first a trigonal-prismatic Primary Molecular Building Block ([Cr3O(isonic)6]+, tp-PMBB-1) was formed and then it was connected to linear linkers or square-planar nodes to afford three novel highly charged cationic metal–organic materials (MOMs) with snx, snw, and stp topologies.

    15. Photodynamic Therapy

      Mannose-Functionalized Mesoporous Silica Nanoparticles for Efficient Two-Photon Photodynamic Therapy of Solid Tumors (pages 11425–11429)

      Dr. Magali Gary-Bobo, Dr. Youssef Mir, Dr. Cédric Rouxel, Dr. David Brevet, Dr. Ilaria Basile, Dr. Marie Maynadier, Ophélie Vaillant, Dr. Olivier Mongin, Dr. Mireille Blanchard-Desce, Prof. Alain Morère, Dr. Marcel Garcia, Dr. Jean-Olivier Durand and Dr. Laurence Raehm

      Version of Record online: 4 OCT 2011 | DOI: 10.1002/anie.201104765

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      Zap 'em! Multifunctionalized mesoporous silica nanoparticles induce significant reduction of tumor size upon two-photon excitation in the near-infrared region while being nontoxic under daylight illumination. These nanoparticles were further tested for in vivo two-photon photodynamic therapy (TPE-PDT). A 70 % regression of tumor size after a single treatment was observed in athymic mice bearing tumor xenografts.

    16. Protein Radicals

      Spectroscopic Signatures of Peptides Containing Tryptophan Radical Cations (pages 11430–11432)

      Bruno Bellina, Dr. Isabelle Compagnon, Sarah Houver, Dr. Philippe Maître, Dr. Abdul-Rahman Allouche, Dr. Rodolphe Antoine and Prof. Philippe Dugourd

      Version of Record online: 10 OCT 2011 | DOI: 10.1002/anie.201104783

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      Mellow yellow: The canonical form of the tryptophan radical cation embedded in an isolated polypeptide shows a distinctive absorption in the yellow region of the spectrum, in contrast with the neutral radical form, which shows an absorption in the blue region (see picture). The spectroscopic diagnostic was supported by vibrational spectroscopy (IRMPD), time-dependent density functional theory, and multireference perturbation theory.

    17. Fabric Coatings

      Durable, Self-Healing Superhydrophobic and Superoleophobic Surfaces from Fluorinated-Decyl Polyhedral Oligomeric Silsesquioxane and Hydrolyzed Fluorinated Alkyl Silane (pages 11433–11436)

      Hongxia Wang, Yuhua Xue, Jie Ding, Lianfang Feng, Xungai Wang and Tong Lin

      Version of Record online: 11 OCT 2011 | DOI: 10.1002/anie.201105069

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      A fabric coating prepared from a homogeneous mixture of fluorinated-decyl polyhedral oligomeric silsesquioxane and hydrolyzed fluorinated alkyl silane shows remarkable self-healing superhydrophobic and superoleophobic properties and excellent durability against UV light, acid, repeated machine washes, and severe abrasion (see picture).

    18. Protein Dynamics

      Kinetics of Conformational Sampling in Ubiquitin (pages 11437–11440)

      David Ban, Michael Funk, Rudolf Gulich, Dalia Egger, Dr. T. Michael Sabo, Korvin F. A. Walter, R. Bryn Fenwick, Karin Giller, Dr. Fabio Pichierri, Dr. Bert L. de Groot, Oliver F. Lange, Prof. Dr. Helmut Grubmüller, Dr. Xavier Salvatella, Martin Wolf, Prof. Dr. Alois Loidl, Prof. Dr. Reiner Kree, Stefan Becker, Dr. Nils-Alexander Lakomek, Dr. Donghan Lee, Dr. Peter Lunkenheimer and Prof. Dr. Christian Griesinger

      Version of Record online: 5 OCT 2011 | DOI: 10.1002/anie.201105086

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      A good combination: The lifetime of interconversion among the ground states of a protein ensemble representation could only be assigned to a time window that is four orders of magnitude large and ranges from 4 ns to 50 μs. By combining temperature-dependent NMR relaxation dispersion (RD) experiments and dielectric relaxation (DR) spectroscopy in solution, the lifetime was now identified to a value of (10±9) μs at 309 K.

    19. Dielectric Properties

      Giant Dielectric Anomaly of a Metal–Organic Perovskite with Four-Membered Ring Ammonium Cations (pages 11441–11445)

      Dr. Biao Zhou, Yuji Imai, Prof. Akiko Kobayashi, Prof. Zhe-Ming Wang and Prof. Hayao Kobayashi

      Version of Record online: 6 OCT 2011 | DOI: 10.1002/anie.201105111

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      Pucker up: A metal–organic perovskite with four-membered-ring azetidinium cations (see structure) exhibited a very broad and unprecedentedly large dielectric peak near 280 K. It is highly possible that the ring-puckering instability of the four-membered-ring ammonium cation plays an essential role in inducing the change of the lattice symmetry and the extraordinarily large dielectric anomaly.

    20. Reactive Intermediates

      Characterization of Vinylgold Intermediates: Gold-Mediated Cyclization of Acetylenic Amides (pages 11446–11450)

      Dr. Olga A. Egorova, Hyewon Seo, Yonghwi Kim, Dr. Dohyun Moon, Prof. Young Min Rhee and Prof. Kyo Han Ahn

      Version of Record online: 5 OCT 2011 | DOI: 10.1002/anie.201106132

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      Hidden nuggets of gold: Mono- and divinylgold complexes (see scheme), key intermediates in the gold-mediated cyclization reaction of N-(propargyl)benzamides, are characterized by NMR and X-ray diffraction analyses. The monovinylgold intermediates undergo proto-deauration in acetonitrile by the substrate. In aqueous media, they produce oxidized products. The divinylgold species undergo reductive elimination to produce the corresponding dimerized products.

      Corrected by:

      Corrigendum: Corrigendum: Characterization of Vinylgold Intermediates: Gold-Mediated Cyclization of Acetylenic Amides

      Vol. 51, Issue 19, 4511, Version of Record online: 25 APR 2012

    21. Asymmetric Catalysis

      Chiral Primary Amine Catalyzed Enantioselective Protonation via an Enamine Intermediate (pages 11451–11455)

      Niankai Fu, Long Zhang, Jiuyuan Li, Prof. Sanzhong Luo and Prof. Jin-Pei Cheng

      Version of Record online: 10 OCT 2011 | DOI: 10.1002/anie.201105477

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      Enamine protonation: A chiral diamine catalyzes an asymmetric Friedel–Crafts reaction through catalytic enantioselective protonation of an enamine. This process can be applied to a range of α-substituted acroleins and indoles with high yields of products and high enantioselectivity (up to 94 % ee). An O[BOND]H/π interaction between H2O and the indole ring was found to play an important role in the transition state (see scheme).

    22. Chiral Quantum Dots

      Optical Coupling Between Chiral Biomolecules and Semiconductor Nanoparticles: Size-Dependent Circular Dichroism Absorption (pages 11456–11459)

      Yunlong Zhou, Zhening Zhu, Wenxiao Huang, Wenjing Liu, Shaojue Wu, Xuefeng Liu, Prof. Yan Gao, Prof. Wei Zhang and Prof. Zhiyong Tang

      Version of Record online: 6 OCT 2011 | DOI: 10.1002/anie.201103762

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      Sizing up QDs: CdTe or CdSe quantum dots (QDs) stabilized by chiral biomolecules show size-dependent circular dichroism (CD) characteristics in the visible light region. Theoretical calculations reveal that the origin of this CD is the combination of the weak optical activity of the biomolecules and the large enhancement effects from the strong absorption of QDs.

    23. Porphyrinoids

      Rearrangements of a [36]Octaphyrin Triggered by Nickel(II) Metalation: Metamorphosis to a Directly meso-β-Linked Diporphyrin (pages 11460–11464)

      Dr. Yasuo Tanaka, Hirotaka Mori, Taro Koide, Prof. Dr. Hideki Yorimitsu, Dr. Naoki Aratani and Prof. Dr. Atsuhiro Osuka

      Version of Record online: 4 OCT 2011 | DOI: 10.1002/anie.201105809

      Thumbnail image of graphical abstract

      Breaking and entering: A figure-of-eight dinickel(II) complex and skeletal rearrangement products including a pyrrole-ring-cleaved product, a directly meso-β-linked diporphyrin (see scheme), and a dearylative oxygenation product have been formed in moderate yields by a nickel(II) metalation of [36]octaphyrin(1.1.1.1.1.1.1.1) in acetonitrile.

    24. Allylation Reactions

      Rhodium-Catalyzed Reaction of 1-Alkenylboronates with Aldehydes Leading to Allylation Products (pages 11465–11469)

      Hiroshi Shimizu, Tomohiro Igarashi, Dr. Tomoya Miura and Prof. Dr. Masahiro Murakami

      Version of Record online: 4 OCT 2011 | DOI: 10.1002/anie.201105148

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      Synthetic equivalents: 1-Alkenylboronates perform the role of an allylating reagent. Their reaction with aldehydes in the presence of a cationic rhodium(I)/dppm catalyst results in a highly diastereoselective production of anti-configured homoallylic alcohols (see scheme; Bpin=4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl).

    25. Synthetic Methods

      Palladium-Catalyzed Decarboxylative Intramolecular Aziridination from 4H-Isoxazol-5-ones Leading to 1-Azabicyclo[3.1.0]hex-2-enes (pages 11470–11473)

      Dr. Kazuhiro Okamoto, Tomohiro Oda, Sho Kohigashi and Prof. Dr. Kouichi Ohe

      Version of Record online: 4 OCT 2011 | DOI: 10.1002/anie.201105153

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      A decarboxylative intramolecular aziridination reaction of alkene-tethered 4H-isoxazol-5-ones with a palladium/phosphine catalyst gave 1-azabicyclo[3.1.0]hex-2-enes in moderate to high yields (see scheme; dba=dibenzylideneacetone). The resulting N-fused bicyclic aziridines readily reacted with various reagents to afford ring-opening pyrroline derivatives.

    26. Phosphorus–Tin Compounds

      Stannylphosphonium Cations (pages 11474–11477)

      Elizabeth MacDonald, Lauren Doyle, Dr. Neil Burford, Dr. Ulrike Werner-Zwanziger and Dr. Andreas Decken

      Version of Record online: 13 OCT 2011 | DOI: 10.1002/anie.201105370

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      Rare examples of P[BOND]Sn bonded cations (see structure; purple Al, gray C, green Cl, orange P, red Sn) are formed in reactions of Me3P or Me2PCH2CH2PMe2 with Me3SnCl or nBu2SnCl2 in the presence of a halide abstracting agent. The demonstrated versatility of the reactions, structures and bonding arrangements bodes well for the development of a diverse P[BOND]Sn chemistry by exploiting coordination chemistry for P[BOND]Sn bond formation.

    27. Pericyclic Cascades

      Pericyclic Cascade with Chirality Transfer: Reaction Pathway and Origin of Enantioselectivity of the Hetero-Claisen Approach to Oxindoles (pages 11478–11482)

      Dr. Nihan Çelebi-Ölçüm, Dr. Yu-hong Lam, Edward Richmond, Dr. Kenneth B. Ling, Dr. Andrew D. Smith and Prof. Dr. Dr. Kendall N. Houk

      Version of Record online: 4 OCT 2011 | DOI: 10.1002/anie.201105412

      Thumbnail image of graphical abstract

      A new pericyclic cascade is proposed for the chiral auxiliary-controlled synthesis of 3,3-disubstituted oxindoles from nitrones and ketenes. The remarkable acyclic 1,6-stereochemical induction, hitherto unexplained, is rationalized by a stereoselective 3+2 cycloaddition step, which installs the stereochemistry, and a chirality transfer step facilitated by a hetero-[3,3]-sigmatropic rearrangement (see picture; PG=protecting group).

    28. Asymmetric Catalysis

      Asymmetric N[BOND]H Insertion Reaction Cooperatively Catalyzed by Rhodium and Chiral Spiro Phosphoric Acids (pages 11483–11486)

      Bin Xu, Prof. Shou-Fei Zhu, Xiu-Lan Xie, Jun-Jie Shen and Prof. Qi-Lin Zhou

      Version of Record online: 4 OCT 2011 | DOI: 10.1002/anie.201105485

      Thumbnail image of graphical abstract

      So near so SPA: Achiral dirhodium(II) carboxylates and chiral spiro phosphoric acids (SPA) cooperatively catalyzed asymmetric N[BOND]H insertion reactions with high enantioselectivity, high yields, and fast reaction rates at low catalyst loading (see scheme; Boc=tert-butyloxycarbonyl, TPA=triphenylacetyl). Chiral spiro phosphoric acid assisted asymmetric proton transfer is proposed as the chiral induction step.

    29. Nitrogen Heterocycles

      Implanting Nitrogen into Hydrocarbon Molecules through C[BOND]H and C[BOND]C Bond Cleavages: A Direct Approach to Tetrazoles (pages 11487–11491)

      Feng Chen, Chong Qin, Dr. Yuxin Cui and Dr. Ning Jiao

      Version of Record online: 10 OCT 2011 | DOI: 10.1002/anie.201105505

      Thumbnail image of graphical abstract

      From simple beginnings: A novel Cu-promoted direct incorporation of nitrogen into simple hydrocarbon molecules under mild and neutral reaction conditions is described. 1,5-Disubstituted tetrazoles are efficiently constructed by two Cmath image[BOND]H and one C[BOND]C bond cleavages (see scheme; TMS=trimethylsilyl). This protocol provides a new and unique strategy to functionalize simple and readily available hydrocarbon molecules.

    30. Hydrosilylation

      Synthesis of a Phosphine-Stabilized Silicon(II) Hydride and Its Addition to Olefins: A Catalyst-Free Hydrosilylation Reaction (pages 11492–11495)

      Dr. Ricardo Rodriguez, Dr. David Gau, Yohan Contie, Tsuyoshi Kato, Dr. Nathalie Saffon-Merceron and Antoine Baceiredo

      Version of Record online: 5 OCT 2011 | DOI: 10.1002/anie.201105639

      Thumbnail image of graphical abstract

      No cat.s allowed: A stable and isolable tricoordinate silicon(II) hydride stabilized by a phosphine ligand was successfully synthesized and fully characterized (see structure, Si green, P yellow, N blue, C gray, H white). Interestingly, this silicon hydride adds to olefins in an unprecedented catalyst-free hydrosilylation reaction in very mild conditions.

    31. Enantioselective Cycloaddition

      Enantioselective Gold(I)-Catalyzed Intramolecular (4+3) Cycloadditions of Allenedienes (pages 11496–11500)

      Isaac Alonso, Hélio Faustino, Dr. Fernando López and Prof. Dr. José L. Mascareñas

      Version of Record online: 13 OCT 2011 | DOI: 10.1002/anie.201105815

      Thumbnail image of graphical abstract

      Allene-tethered dienes (1) undergo an intramolecular and highly enantioselective (4+3) cycloaddition when treated with suitable chiral phosphoramidite/gold(I) catalysts (see scheme; Ar=9-anthracenyl). The reactions provide synthetically relevant [5.3.0] and [5.4.0] fused bicyclic systems 2 with good yields, complete diastereocontrol, and excellent enantioselectivities.

    32. Natural Products

      Total Synthesis of (+)-Daphmanidin E (pages 11501–11505)

      Matthias E. Weiss and Prof. Dr. Erick M. Carreira

      Version of Record online: 11 OCT 2011 | DOI: 10.1002/anie.201104681

      Thumbnail image of graphical abstract

      From ring to ring: The first total synthesis of (+)-daphmanidin E features rapid access to an enantiomerically pure bicyclo[2.2.2]octadione and elaboration around its periphery through the implementation of two Claisen rearrangements, the use of a copper/peptide complex for reagent-controlled stereoselective conjugate addition, a diastereoselective hydroboration, and a cobalt-catalyzed alkyl-Heck cyclization.

    33. Oxygen Heterocycles

      Palladium-Catalyzed Asymmetric Synthesis of 2-Alkynyl Oxacycles (pages 11506–11510)

      David S. B. Daniels, Dr. Amber L. Thompson and Dr. Edward A. Anderson

      Version of Record online: 6 OCT 2011 | DOI: 10.1002/anie.201105720

      Thumbnail image of graphical abstract

      Oxyacetylene: Unusual palladium-catalyzed cyclizations of cyclic and acyclic propargylic carbonates give 2-alkynyl oxacycles. The reactions proceed with very high stereoselectivity for both syn- and anti-disubstituted furans and pyrans, and with exceptional regioselectivity. In addition, two-directional cyclizations of bis-propargylic carbonate substrates yield bifurans with complete stereocontrol for all diastereomers.

    34. C[BOND]H Amination

      Amination of Benzoxazoles and 1,3,4-Oxadiazoles Using 2,2,6,6-Tetramethylpiperidine-N-oxoammonium Tetrafluoroborate as an Organic Oxidant (pages 11511–11515)

      Sebastian Wertz, Shintaro Kodama and Prof. Dr. Armido Studer

      Version of Record online: 11 OCT 2011 | DOI: 10.1002/anie.201104735

      Thumbnail image of graphical abstract

      No transition metals are necessary to convert benzoxazoles and 1,3,4-oxadiazoles into the corresponding pharmacologically interesting 2-aminated heterocycles by formal direct C(2)-amination using tetramethylpiperidine-N-oxoammonium tetrafluoroborate (TEMPO+BF4) as an oxidant (see scheme; TEMP=2,2,6,6-tetramethylpiperidine; TfOH=trifluoromethanesulfonic acid).

    35. Hybrid Materials

      Diphosphorus Complexes as Building Blocks for the Design of Phosphorus-Containing Organometallic–Organic Hybrid Materials (pages 11516–11519)

      Bianca Attenberger, Dr. Stefan Welsch, Dr. Manfred Zabel, Dr. Eugenia Peresypkina and Prof. Dr. Manfred Scheer

      Version of Record online: 12 OCT 2011 | DOI: 10.1002/anie.201103046

      Thumbnail image of graphical abstract

      The flexible coordination behavior of Pn ligand complexes in solution is utilized to create unprecedented coordination networks. In combination with ditopic organic linker units, organometallic–organic hybrid compounds are accessible. Depending on the nature of the metal center, metallaparacyclophane-like structures as well as 1D and 2D polymeric arrangements can be achieved.

    36. Alzheimer Research

      The Dynamic Structure of Filamentous Tau (pages 11520–11524)

      Stefan Bibow, Dr. Marco D. Mukrasch, Subashchandrabose Chinnathambi, Dr. Jacek Biernat, Prof. Dr. Christian Griesinger, Prof. Dr. Eckhard Mandelkow and Prof. Dr. Markus Zweckstetter

      Version of Record online: 11 OCT 2011 | DOI: 10.1002/anie.201105493

      Thumbnail image of graphical abstract

      Getting inside a fuzzy coat: The dynamic structure of the “fuzzy coat”, N- and C-terminal sections around the core of the tau filament consists of over 200 amino acids, and has been characterized by NMR spectroscopy (see picture, model of the long range interactions). The results indicate how conformation specific antibodies bind to the tau protein (fibers of which are a characteristic symptom of Alzheimer disease).

    37. Doping

      Tailoring the Shape of Metal Ad-Particles by Doping the Oxide Support (pages 11525–11527)

      Dr. Xiang Shao, Stefano Prada, Dr. Livia Giordano, Dr. Gianfranco Pacchioni, Dr. Niklas Nilius and Prof. Hans-Joachim Freund

      Version of Record online: 11 OCT 2011 | DOI: 10.1002/anie.201105355

      Thumbnail image of graphical abstract

      Just a Mo: Tiny Mo concentrations in a CaO film can influence the growth of adsorbed gold. On undoped films, three dimensional gold structures form (see picture, top) whereas on the doped films flat islands appear (bottom). The change results from a charge transfer from the Mo dopant to the Au atoms, a process suggested by STM measurements and DFT calculations.

    38. Polybromides

      Structural Proof for a Higher Polybromide Monoanion: Investigation of [N(C3H7)4][Br9] (pages 11528–11532)

      Dipl.-Chem. Heike Haller, Mathias Ellwanger, Dipl.-Chem. Alexander Higelin and Dr. Sebastian Riedel

      Version of Record online: 6 OCT 2011 | DOI: 10.1002/anie.201105237

      Thumbnail image of graphical abstract

      Bromine's nine: The first crystal structure of a higher polybromide monoanion, [NPr4][Br9] is reported along with its IR and Raman spectra (see picture). Owing to its low melting point and vapor pressure, this substance can be classified as an ionic liquid. It shows surprisingly high conductivity which may enable its applications as electrolyte in batteries.

    39. Trifluoromethylation

      Traceless Solid-Phase Synthesis of Trifluoromethylarenes (pages 11533–11535)

      Dipl.-Chem. Marion Döbele, Dr. Matthias S. Wiehn and Prof. Dr. Stefan Bräse

      Version of Record online: 13 OCT 2011 | DOI: 10.1002/anie.201105446

      Thumbnail image of graphical abstract

      Save the best for last: In the first method for the trifluoromethylation of immobilized arenes, the aryl halides are attached through a dithioester linkage to the Merrifield resin and then functionalized by means of numerous reactions including transition-metal-catalyzed cross-couplings. In the final step the fluorinating cleavage reaction provides the trifluoromethylarenes in good yields and high purities.

    40. Nanomaterials

      Optical Imaging of CdSe Nanowires with Nanoscale Resolution (pages 11536–11538)

      Miriam Böhmler, Zhe Wang, Anton Myalitsin, Prof. Dr. Alf Mews and Prof. Dr. Achim Hartschuh

      Version of Record online: 13 OCT 2011 | DOI: 10.1002/anie.201105217

      Thumbnail image of graphical abstract

      Down to the wire: High-resolution photoluminescence (PL) and Raman images of CdSe nanowires were obtained using tip-enhanced near-field optical microscopy. They show that the optical properties of the CdSe nanowires vary significantly within a few nanometers leading to strong spatial fluctuations in both PL intensities and energies (see picture).

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