Angewandte Chemie International Edition

Cover image for Vol. 52 Issue 8

February 18, 2013

Volume 52, Issue 8

Pages 2129–2372

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    1. You have free access to this content
      Cover Picture: IR-ATR Chemical Sensors Based on Planar Silver Halide Waveguides Coated with an Ethylene/Propylene Copolymer for Detection of Multiple Organic Contaminants in Water (Angew. Chem. Int. Ed. 8/2013) (page 2129)

      Rui Lu, Dr. Guoping Sheng, Dr. Wenwei Li, Prof. Dr. Hanqing Yu, Dr. Yosef Raichlin, Prof. Dr. Abraham Katzir and Prof. Dr. Boris Mizaikoff

      Article first published online: 1 FEB 2013 | DOI: 10.1002/anie.201300592

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      Rapidly responding in situ analysis methods, such as mid-infrared optochemical sensors utilizing evanescent field absorption techniques, may inherently provide qualitative and quantitative information on multiple volatile organic contaminants in water. In their Communication on page 2265 ff., B. Mizaikoff et al. describe a planar infrared attenuated total reflection (IR-ATR) fiberoptic sensor that was coated with an ethylene/propylene copolymer. Such a system may be used for continuous monitoring of the water quality.

    2. You have free access to this content
      Inside Cover: Asbestos-like Pathogenicity of Long Carbon Nanotubes Alleviated by Chemical Functionalization (Angew. Chem. Int. Ed. 8/2013) (page 2130)

      Dr. Hanene Ali-Boucetta, Dr. Antonio Nunes, Dr. Raquel Sainz, Dr.  M. Antonia Herrero, Dr. Bowen Tian, Prof. Maurizio Prato, Dr. Alberto Bianco and Prof. Kostas Kostarelos

      Article first published online: 30 JAN 2013 | DOI: 10.1002/anie.201300458

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      Alleviation of the asbestos-like pathogenicity of long, pristine carbon nanotubes is possible by modifying their surface and reducing their effective length by de-bundling, following certain types of chemical functionalization. In their Communication on page 2274 ff., M. Prato, A. Bianco, K. Kostarelos, et al. show that a 1,3-dipolar cycloaddition reaction on carbon nanotubes produces well-dispersed individualized nanotubes with a risk-free toxicity profile.

    3. You have free access to this content
      Inside Back Cover: Discovery of Hepatitis C Virus NS3 Helicase Inhibitors by a Multiplexed, High-Throughput Helicase Activity Assay Based on Graphene Oxide (Angew. Chem. Int. Ed. 8/2013) (page 2373)

      Hongje Jang, Soo-Ryoon Ryoo, Young-Kwan Kim, Soojin Yoon, Henna Kim, Prof. Dr. Sang Woo Han, Prof. Dr. Byong-Seok Choi, Prof. Dr. Dong-Eun Kim and Prof. Dr. Dal-Hee Min

      Article first published online: 28 JAN 2013 | DOI: 10.1002/anie.201300345

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      DNA helicases are important targets for anti-viral drug development. In their Communication on page 2340 ff., D.-H. Min et al. use graphene oxide for high-throughput chemical screening to discover new inhibitors of two different helicases derived from hepatitis C virus and severe acute respiratory syndrome (SARS) coronavirus in a multiplexed assay. The developed assay can also be used to validate hits from the helicase inhibitor screen.

    4. You have free access to this content
      Back Cover: Pulling the Levers of Photophysics: How Structure Controls the Rate of Energy Dissipation (Angew. Chem. Int. Ed. 8/2013) (page 2374)

      Thomas S. Kuhlman, Prof. Michael Pittelkow, Prof. Theis I. Sølling and Prof. Klaus B. Møller

      Article first published online: 25 JAN 2013 | DOI: 10.1002/anie.201300344

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      Femtosecond time-resolved spectroscopy can open the window to fascinating new perspectives of internal conversion processes. In their Communication on page 2247 ff., T. I. Sølling, K. B. Møller, and co-workers show that the S2 to S1 transition of a series of cyclic ketones is mediated by very few degrees of freedom. This knowledge makes it possible to predict and influence the transition dynamics through modification of the molecular structure.

  2. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    1. Graphical Abstract: Angew. Chem. Int. Ed. 8/2013 (pages 2133–2148)

      Article first published online: 13 FEB 2013 | DOI: 10.1002/anie.201390005

  3. Corrigenda

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    1. You have free access to this content
      Corrigendum: A Remarkable Organometallic Transformation on a Cage-Incarcerated Dinuclear Ruthenium Complex (page 2147)

      Shinnosuke Horiuchi, Dr. Takashi Murase and Prof. Dr. Makoto Fujita

      Article first published online: 13 FEB 2013 | DOI: 10.1002/anie.201300218

      This article corrects:

      A Remarkable Organometallic Transformation on a Cage-Incarcerated Dinuclear Ruthenium Complex

      Vol. 51, Issue 48, 12029–12031, Article first published online: 18 OCT 2012

    2. You have free access to this content
    3. You have free access to this content
      Corrigendum: A Bioreducible Polymer for Efficient Delivery of Fas-Silencing siRNA into Stem Cell Spheroids and Enhanced Therapeutic Angiogenesis (page 2147)

      Dr. Min Suk Shim, Dr. Suk Ho Bhang, Dr. Kyunghwan Yoon, Prof. Kyunghee Choi and Prof. Younan Xia

      Article first published online: 13 FEB 2013 | DOI: 10.1002/anie.201210337

      This article corrects:
    4. You have free access to this content
      Corrigendum: Low-Valent Ge2 and Ge4 Species Trapped by N-Heterocyclic Gallylene (page 2148)

      Adinarayana Doddi, Dr. Christian Gemel, Manuela Winter, Dr. Roland A Fischer, Catharina Goedecke, Dr. Henry S. Rzepa and Dr. Gernot Frenking

      Article first published online: 13 FEB 2013 | DOI: 10.1002/anie.201300460

      This article corrects:

      Low-Valent Ge2 and Ge4 Species Trapped by N-Heterocyclic Gallylene

      Vol. 52, Issue 1, 450–454, Article first published online: 21 NOV 2012

  4. News

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

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    1. Liming Zhang (page 2156)

      Article first published online: 4 NOV 2012 | DOI: 10.1002/anie.201207556

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      “In a spare hour, I check out the latest news and listen to some folk music. My favorite name reaction is the Ferrier rearrangement …” This and more about Liming Zhang can be found on page 2156.

  6. News

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

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    1. Supercritical Water. A Green Solvent: Properties and Uses. Edited by Yizhak Marcus. (page 2158)

      G. Herbert Vogel

      Article first published online: 25 JAN 2013 | DOI: 10.1002/anie.201300111

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      John Wiley & Sons, Hoboken, 2012. 218 pp., hardcover, € 95.90.—ISBN 978-0470889473

  8. Highlights

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    1. Organocatalysis

      Mechanism of Diphenylprolinol Silyl Ether Catalyzed Michael Addition Revisited—but Still Controversial (pages 2160–2162)

      Prof. Christina Moberg

      Article first published online: 3 JAN 2013 | DOI: 10.1002/anie.201207775

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      Two views: The mechanism of the conjugate addition of linear aldehydes to nitro olefins has been investigated by two research groups. In spite of extensive experimental data, important questions remain unanswered (see scheme; TMS=trimethylsilyl, En=enamine).

    2. Zeolite Synthesis

      Solventless Synthesis of Zeolites (pages 2163–2165)

      Prof. Russell E. Morris and Prof. Stuart L. James

      Article first published online: 16 JAN 2013 | DOI: 10.1002/anie.201209002

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      No added solvent means no waste solvent or recycling costs. Understandably the chemical industry is interested in developing approaches to increase the product to solvent ratio in synthesis. In recent work various zeolites were prepared by grinding the dry materials and then heating to 180 °C, and this method could lead to significant savings in zeolite synthesis.

  9. Review

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    1. Mechanisms of Crystallization

      Nucleation of Organic Crystals—A Molecular Perspective (pages 2166–2179)

      Prof. Roger J. Davey, Prof. Sven L. M. Schroeder and Prof. Joop H. ter Horst

      Article first published online: 10 JAN 2013 | DOI: 10.1002/anie.201204824

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      Everything starts out small: The synthesis of organic materials depends strongly on the first steps of molecular self-assembly during crystal nucleation. This Review summarizes current knowledge on these processes. Self-association in different solvents can lead to the creation of different building blocks, which form differently packed nuclei and thus in each case specific crystalline phases.

  10. Communications

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    1. Donor–Acceptor Nanohybrids

      Self-Ordering Electron Donor–Acceptor Nanohybrids Based on Single-Walled Carbon Nanotubes Across Different Scales (pages 2180–2184)

      Dr. Fulvio G. Brunetti, Dr. Carlos Romero-Nieto, Javier López-Andarias, Dr. Carmen Atienza, Dr. Juan Luis López, Prof. Dirk M. Guldi and Prof. Nazario Martín

      Article first published online: 22 JAN 2013 | DOI: 10.1002/anie.201207006

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      From nano- to macroscale: The immobilization of photo- and redox-active 9,10-di(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene-based dipeptide 1 onto SWCNTs resulted in a high order of self-alignment among 1/SWCNTs (see picture). The assembly of the 1/SWCNTs is the key for stabilizing long-lived charge-separated states that are formed upon photoexcitation of the SWCNTs.

    2. G-Quadruplex Ligands

      Interaction of Cationic Manganese Porphyrin with G-Quadruplex Nucleic Acids Probed by Differential Labeling of the Two Faces of the Porphyrin (pages 2185–2188)

      Dr. Vincent Pradines and Dr. Geneviève Pratviel

      Article first published online: 22 JAN 2013 | DOI: 10.1002/anie.201209705

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      On the flip side: A free manganese porphyrin, when activated into a high-valent metal-oxo species, mediates O atom transfer (epoxidation) from both faces. This results in a mixed labeling of epoxide in labeled water. When the porphyrin (blue oval, see scheme) is bound to G-quadruplex DNA (yellow boxes), the O atom transfer reaction takes place only on the accessible face of the porphyrin. This shows the binding mode of the porphyrin to the G-quadruplex DNA.

    3. Cross-Coupling

      Stille Coupling Involving Bulky Groups Feasible with Gold Cocatalyst (pages 2189–2193)

      Juan delPozo, Desirée Carrasco, Dr. Mónica H. Pérez-Temprano, Dr. Max García-Melchor, Prof. Rosana Álvarez, Prof. Juan A. Casares and Prof. Pablo Espinet

      Article first published online: 22 JAN 2013 | DOI: 10.1002/anie.201209262

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      Gold shuttle: Bulky groups, which will not (or only very sluggishly) undergo Stille coupling with stannanes and inexpensive ligands, can be efficiently coupled using bimetallic catalysis. A gold cocatalyst serves as an efficient shuttle to convey the bulky group from tin to palladium by reducing the steric crowding in the transition-states (see scheme).

    4. Heterocycle Synthesis

      Intramolecular C(sp3)[BOND]N Coupling by Oxidation of Benzylic C,N-Dianions (pages 2194–2197)

      Jenna L. Jeffrey, Emily S. Bartlett and Prof. Richmond Sarpong

      Article first published online: 16 JAN 2013 | DOI: 10.1002/anie.201209591

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      What a couple! An intramolecular, C(sp3)[BOND]N coupling to afford azacycles is reported. This reaction proceeds through the oxidation of benzylic C,N-dianions with iodine and builds on an earlier discovery during the synthesis of the natural product lyconadin A. The current study employs conformationally unbiased substrates with less acidic C[BOND]H bonds and less reactive nitrogen nucleophiles. ZnCl2 was identified as an important additive.

    5. Radical Reactions

      Silver-Catalyzed Hydrotrifluoromethylation of Unactivated Alkenes with CF3SiMe3 (pages 2198–2202)

      Xinyue Wu, Dr. Lingling Chu and Prof. Dr. Feng-Ling Qing

      Article first published online: 22 JAN 2013 | DOI: 10.1002/anie.201208971

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      A silver bullet: The title reaction results in selective formation of trifluoromethylated alkanes, and is in contrast to the previously reported transition-metal-catalyzed trifluoromethylation of olefins to generate a series of trifluoromethylated allylic compounds. Preliminary mechanistic investigations indicate that the current hydrotrifluoromethylation proceeds through a pathway involving a CF3 radical species.

    6. Synthetic Methods

      Iridium-Catalyzed Asymmetric Hydrogenation of α-Alkylidene Succinimides (pages 2203–2206)

      Yuanyuan Liu and Prof. Wanbin Zhang

      Article first published online: 18 JAN 2013 | DOI: 10.1002/anie.201209126

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      Not to be out PhOXed! The title reaction provides a new approach to chiral succinimide derivatives with excellent yields and ee values by using a low catalyst loading (0.05 mol %) and mild reaction conditions. Chiral 3-benzyl pyrrolidines and 1-hydroxypyrrolidine-2,5-diones, important structural motifs in natural products and pharmaceuticals, could be readily prepared. BARF=tetrakis[3,5-bis(trifluoromethyl)phenyl]borate.

    7. C[BOND]H Activation

      A Cationic High-Valent Cp*CoIII Complex for the Catalytic Generation of Nucleophilic Organometallic Species: Directed C[BOND]H Bond Activation (pages 2207–2211)

      Tatsuhiko Yoshino, Hideya Ikemoto, Dr. Shigeki Matsunaga and Prof. Dr. Motomu Kanai

      Article first published online: 16 JAN 2013 | DOI: 10.1002/anie.201209226

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      Active without activation: In an inexpensive and atom-economical approach to C[BOND]H bond functionalization, a cationic CoIII complex (see scheme) was used to generate nucleophilic organometallic species in situ without additional activating reagents. Under these conditions, aryl C[BOND]H bonds underwent efficient addition to polar electrophiles, including α,β-unsaturated N-acyl pyrroles as β-substituted ester and amide surrogates.

    8. Heterocycles

      Synthesis of Pyridines by Carbenoid-Mediated Ring Opening of 2H-Azirines (pages 2212–2216)

      Nicole S. Y. Loy, Dr. Alok Singh, Dr. Xianxiu Xu and Prof. Cheol-Min Park

      Article first published online: 10 JAN 2013 | DOI: 10.1002/anie.201209301

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      Roaming the range: The title reaction tolerates a wide range of substituents on the resulting pyridine ring using mild reaction conditions (see scheme; esp=α,α,α′,α′-tetramethyl-1,3-benzenedipropionic acid). The formation of the key intermediate is catalyst-controlled, and subsequent cyclization and oxidation affords pyridines in excellent yields. The method has been used for the efficient synthesis of polyarylpyridines.

    9. Homogeneous Catalysis

      Palladium-Catalyzed Intramolecular ipso-Friedel–Crafts Alkylation of Phenols and Indoles: Rearomatization-Assisted Oxidative Addition (pages 2217–2220)

      Dr. Tetsuhiro Nemoto, Zengduo Zhao, Takuya Yokosaka, Yuta Suzuki, Riliga Wu and Prof. Dr. Yasumasa Hamada

      Article first published online: 15 JAN 2013 | DOI: 10.1002/anie.201209317

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      Inspiroation: A novel synthesis of spirocycles based on a palladium-catalyzed intramolecular ipso-Friedel–Crafts alkylation of phenols (see scheme; dba=dibenzylideneacetone) and indoles is described. Mechanistic studies show that the reaction proceeds through an unprecedented rearomatization-assisted oxidative addition.

    10. Synthetic Methodology

      Enantioselective Synthesis of Epoxides Having a Tetrasubstituted Trifluoromethylated Carbon Center: Methylhydrazine-Induced Aerobic Epoxidation of β,β-Disubstituted Enones (pages 2221–2225)

      Hiroyuki Kawai, Satoshi Okusu, Zhe Yuan, Etsuko Tokunaga, Akihito Yamano, Dr. Motoo Shiro and Prof. Norio Shibata

      Article first published online: 21 JAN 2013 | DOI: 10.1002/anie.201209355

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      The unprecedented title reaction is catalyzed by a methylhydrazine/base/organocatalyst (1) system. Biologically attractive epoxides (2) having a tetrasubstituted trifluoromethylated carbon center were obtained with excellent enantioselectivity for the first time. 18O-labeling experiments suggest a mechanism involving the activation of molecular oxygen. MTBE=methyl tert-butyl ether.

    11. Synthetic Methods

      Template-Free Synthesis of VO2 Hollow Microspheres with Various Interiors and Their Conversion into V2O5 for Lithium-Ion Batteries (pages 2226–2230)

      Dr. Anqiang Pan, Hao Bin Wu, Le Yu and Prof. Xiong Wen (David) Lou

      Article first published online: 11 JAN 2013 | DOI: 10.1002/anie.201209535

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      Getting a charge out of microspheres: Uniform VO2 microspheres with various complex interiors, such as yolk-shelled and multi-shelled hollow structures, have been synthesized through a template-free solvothermal method. After annealing in air, the derived V2O5 microspheres manifest improved electrochemical performance as a high-capacity cathode material for lithium-ion batteries.

    12. Amide Hydrogenation

      Catalytic Hydrogenation of Amides to Amines under Mild Conditions (pages 2231–2234)

      Dipl.-Chem. Mario Stein and Prof. Dr. Bernhard Breit

      Article first published online: 6 DEC 2012 | DOI: 10.1002/anie.201207803

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      Under (not so much) pressure: A general method for the hydrogenation of tertiary and secondary amides to amines with excellent selectivity using a bimetallic Pd–Re catalyst has been developed. The reaction proceeds under low pressure and comparatively low temperature. This method provides organic chemists with a simple and reliable tool for the synthesis of amines.

    13. Photo-Responsive Materials

      Photo-controlled Growth of Telechelic Polymers and End-linked Polymer Gels (pages 2235–2238)

      Dr. Huaxing Zhou and Prof. Dr. Jeremiah A. Johnson

      Article first published online: 17 JAN 2013 | DOI: 10.1002/anie.201207966

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      Growing pores: Exposure of a bis-norbornene trithiocarbonate to long-wavelength UV light, or sunlight, in the presence of N-isopropylacrylamide (NiPAAm) led to well-defined norbornene–telechelic poly(NiPAAm) macromers. The macromers were end-linked with a tris-tetrazine via inverse-electron-demand Diels–Alder cycloaddition to generate polymer gels. Addition of new monomer, followed by exposure to sunlight, led to “photo-growth” of the network pores.

    14. Radical Reactions

      Metal-Free Reductive Cleavage of Benzylic Esters and Ethers: Fragmentations Result from Single and Double Electron Transfers (pages 2239–2242)

      Eswararao Doni, Steven O'Sullivan and Prof. Dr. John A. Murphy

      Article first published online: 11 JAN 2013 | DOI: 10.1002/anie.201208066

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      The mechanisms for the reductive cleavage of benzylic esters and ethers by neutral organic electron donor 1 are different (see scheme). Products isolated from the cleavage of benzylic ethers result from the transfer of two electrons, without the intermediacy of benzyl radicals, which are believed to be intermediates in the reductive cleavage of benzylic esters.

    15. Activation of Small Molecules

      Facile Carbon Monoxide Reduction at Intramolecular Frustrated Phosphane/Borane Lewis Pair Templates (pages 2243–2246)

      Dr. Muhammad Sajid, Lisa-Maria Elmer, Christoph Rosorius, Dr. Constantin G. Daniliuc, Prof. Dr. Stefan Grimme, Dr. Gerald Kehr and Prof. Dr. Gerhard Erker

      Article first published online: 15 JAN 2013 | DOI: 10.1002/anie.201208750

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      A new reaction pathway: Carbon monoxide is readily reduced by Piers' borane at a frustrated Lewis pair (FLP) to yield a formylborane stabilized by the FLP (see picture). This reaction may be considered a typical example of efficient activation of a small molecule by a FLP.

    16. Gas-Phase Chemistry

      Pulling the Levers of Photophysics: How Structure Controls the Rate of Energy Dissipation (pages 2247–2250)

      Thomas S. Kuhlman, Prof. Michael Pittelkow, Prof. Theis I. Sølling and Prof. Klaus B. Møller

      Article first published online: 16 JAN 2013 | DOI: 10.1002/anie.201208197

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      Internal conversion: The energy difference between the Franck–Condon and equilibrium geometries and the vibrational frequency of one or a few modes determine the relative importance of adiabatic and nonadiabatic dynamics and thus the rate of electronic energy dissipation (see picture). In the cycloketones, variations in these quantities lead to a difference in the timescale for the S2→S1 transition.

    17. Diversity-Oriented Synthesis

      Relay Catalytic Branching Cascade: A Technique to Access Diverse Molecular Scaffolds (pages 2251–2255)

      Dr. Nitin T. Patil, Valmik S. Shinde and Dr. Balasubramanian Sridhar

      Article first published online: 17 JAN 2013 | DOI: 10.1002/anie.201208738

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      Skeletal diversity: The reactions of alkynoic acids (A, common type of substrates) with various scaffold-building agents (B) under gold catalysis produce a series of multifunctional polyheterocyclic structures (see scheme). The approach enables the preparation of compound libraries with high skeletal diversity.

    18. Oxidative Coupling

      Copper-Catalyzed Oxidative Coupling of Alkenes with Aldehydes: Direct Access to α,β-Unsaturated Ketones (pages 2256–2259)

      Jing Wang, Dr. Chao Liu, Jiwen Yuan and Prof. Aiwen Lei

      Article first published online: 25 JAN 2013 | DOI: 10.1002/anie.201208920

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      Let's get radical: The first copper-catalyzed oxidative coupling of alkenes and aldehydes was developed. Various aldehydes were utilized as substrates to construct α,β-unsaturated ketones. A preliminary mechanistic study indicated that this reaction is likely to proceed through a single-electron transfer.

    19. Asymmetric Catalysis

      Palladium-Catalyzed Asymmetric Allylic Alkylation of 3-Aryloxindoles with Allylidene Dipivalate: A Useful Enol Pivalate Product (pages 2260–2264)

      Prof. Barry M. Trost, James T. Masters and Dr. Aaron C. Burns

      Article first published online: 17 JAN 2013 | DOI: 10.1002/anie.201209783

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      Triple A: The catalytic asymmetric allylic alkylation (AAA) of 3-aryloxindoles with allylidene dipivalate is described. This reaction affords stable, synthetically useful enol pivalates in high yield and with excellent regio- and enantioselectivity. A broad range of substrates is tolerated, including unprotected and 3-heteroaryl nucleophiles.

    20. Analytical Methods

      IR-ATR Chemical Sensors Based on Planar Silver Halide Waveguides Coated with an Ethylene/Propylene Copolymer for Detection of Multiple Organic Contaminants in Water (pages 2265–2268)

      Rui Lu, Dr. Guoping Sheng, Dr. Wenwei Li, Prof. Dr. Hanqing Yu, Dr. Yosef Raichlin, Prof. Dr. Abraham Katzir and Prof. Dr. Boris Mizaikoff

      Article first published online: 1 FEB 2013 | DOI: 10.1002/anie.201209256

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      Sensitive: Several monocyclic aromatic hydrocarbons, for example p-, m-, o-xylene, toluene, and benzene (1–5), were detected in a single measurement by using a planar infrared attenuated total reflection (IR-ATR) fiberoptic sensor that was coated with ethylene/propylene copolymer. Compared to conventional IR sensing systems, this device exhibits a large dynamic detection range.

    21. DNA Structures

      The G-Triplex DNA (pages 2269–2273)

      Dr. Vittorio Limongelli, Stefano De Tito, Dr. Linda Cerofolini, Dr. Marco Fragai, Dr. Bruno Pagano, Dr. Roberta Trotta, Dr. Sandro Cosconati, Dr. Luciana Marinelli, Prof. Ettore Novellino, Prof. Ivano Bertini, Prof. Antonio Randazzo, Prof. Claudio Luchinat and Prof. Michele Parrinello

      Article first published online: 17 JAN 2013 | DOI: 10.1002/anie.201206522

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      Triplex with a twist: Through metadynamics calculations, the thrombin binding aptamer (TBA) has been shown to adopt a stable G-triplex structural motif, in addition to the usual G-quadruplex (see scheme). An 11-mer oligonucleotide was also shown to form a stable G-triplex, whose structural and thermodynamic properties have been characterized.

    22. Nanotube Toxicology

      Asbestos-like Pathogenicity of Long Carbon Nanotubes Alleviated by Chemical Functionalization (pages 2274–2278)

      Dr. Hanene Ali-Boucetta, Dr. Antonio Nunes, Dr. Raquel Sainz, Dr.  M. Antonia Herrero, Dr. Bowen Tian, Prof. Maurizio Prato, Dr. Alberto Bianco and Prof. Kostas Kostarelos

      Article first published online: 14 JAN 2013 | DOI: 10.1002/anie.201207664

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      Sometimes shorter is better: The apparent similarity between multi-walled carbon nanotubes (MWNTs) and asbestos fibers has generated serious concerns about their safety profile. The asbestos-like pathogenicity observed for long, pristine nanotubes (NTlong, see scheme) can be completely alleviated if their effective length is decreased as a result of chemical functionalization, such as with tri(ethylene glycol) (TEG).

    23. Self-Assembled Peptide Architecture

      The Structure of Cross-β Tapes and Tubes Formed by an Octapeptide, αSβ1 (pages 2279–2283)

      Dr. Kyle L. Morris, Dr. Shahin Zibaee, Dr. Lin Chen, Dr. Michel Goedert, Prof. Pawel Sikorski and Prof. Louise C. Serpell

      Article first published online: 10 JAN 2013 | DOI: 10.1002/anie.201207699

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      Elaborate morphology: The αSβ1 peptide, a fragment of α-synuclein, assembles into flat tapes consisting of a peptide bilayer, which can be modeled based on the cross-β structure found in amyloid proteins. The tapes are stabilized by hydrogen bonding, whilst the amphiphilic nature of the peptide results in the thin bilayer structure. To further stabilize the structure, these tapes may twist to form helical tapes, which subsequently close into nanotubes.

    24. DNA Nanotechnology

      Non-covalent Single Transcription Factor Encapsulation Inside a DNA Cage (pages 2284–2288)

      Dr. Robert Crawford, Dr. Christoph M. Erben, Dr. Javier Periz, Dr. Lucy M. Hall, Prof. Tom Brown, Prof. Andrew J. Turberfield and Dr. Achillefs N. Kapanidis

      Article first published online: 16 JAN 2013 | DOI: 10.1002/anie.201207914

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      CAP-turing the moment: A cage made from DNA can be used to encapsulate a transcription factor (catabolite activator protein, CAP; see figure) without covalent attachment. CAP is shown to stably bind inside the DNA cage at a 1:1 ratio by bending one edge to accommodate the protein. Single-molecule fluorescence measurements confirm the orientation of CAP within the cage.

    25. Surface Chemistry

      Ultralow Voltage Electrowetting on a Solidlike Ionic-Liquid Dielectric Layer (pages 2289–2292)

      Xiaoning Zhang and Prof. Yuguang Cai

      Article first published online: 16 JAN 2013 | DOI: 10.1002/anie.201207857

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      Electrowetting was achieved on an ionic-liquid-coated (IL) dielectric layer at a driving voltage of just 70 mV and 5 V in AC and DC mode, respectively. AFM studies suggest that the high capacitance density of the ionic-liquid dielectric layer is the reason for the low voltage electrowetting (see picture; OTS=octadecyltrichlorosilane).

    26. Enzyme Catalysis

      Asymmetric Enzymatic Hydration of Hydroxystyrene Derivatives (pages 2293–2297)

      Christiane Wuensch, Johannes Gross, Dr. Georg Steinkellner, Prof. Karl Gruber, Dr. Silvia M. Glueck and Prof. Kurt Faber

      Article first published online: 17 JAN 2013 | DOI: 10.1002/anie.201207916

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      More than one activity: Owing to their hydratase activity, phenolic acid decarboxylases catalyze the regio- and stereoselective addition of H2O across the C[DOUBLE BOND]C double bond of hydroxystyrene derivatives yielding (S)-4-(1-hydroxyethyl)phenols with up to 82 % conversion and 71 % ee. Based on structure analysis and molecular docking simulations, a catalytic mechanism for this novel enzymatic reaction is proposed.

    27. Natural Products

      Elucidating the Biosynthetic Pathway for Vibralactone: A Pancreatic Lipase Inhibitor with a Fused Bicyclic β-Lactone (pages 2298–2302)

      Dr. Pei-Ji Zhao, Yan-Long Yang, Prof. Dr. Liangchen Du, Prof. Dr. Ji-Kai Liu and Prof. Ying Zeng

      Article first published online: 21 JAN 2013 | DOI: 10.1002/anie.201208182

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      Not so simple: Evidence from 13C-labeling studies, metabolite profiling, and cell-free conversion established that the bicycle skeleton of vibralactone is derived from an aryl ring moiety and both shikimate and phenylalanine pathways may contribute. VibPT was found to be potentially involved in vibralactone biosynthesis, as well as an aromatic PTase, which was first characterized in basidiomycete fungi. OPP=pyrophosphate.

      Corrected by:

      Corrigendum: Corrigendum: Elucidating the Biosynthetic Pathway for Vibralactone: A Pancreatic Lipase Inhibitor with a Fused Bicyclic β-Lactone

      Vol. 52, Issue 20, 5203, Article first published online: 3 MAY 2013

    28. Radiochemistry

      Stoichiometric Leverage: Rapid 18F-Aryltrifluoroborate Radiosynthesis at High Specific Activity for Click Conjugation (pages 2303–2307)

      Zhibo Liu, Dr. Ying Li, Jerome Lozada, Dr. Paul Schaffer, Dr. Michael J. Adam, Dr. Thomas J. Ruth and Dr. David M. Perrin

      Article first published online: 11 JAN 2013 | DOI: 10.1002/anie.201208551

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      Raising the 18F3-BAr: Specific activities of most 18F-labeled radiotracers fall below 2 Ci μmol−1, yet 18F-aryltrifluoroborate synthesis affords specific activities as high as 15 Ci μmol−1. This has been confirmed by using click chemistry to link an [18F]-ArBF3 to rhodamine and thereby demonstrating a rapid and generalizable one-pot method for preparing a fluorescent tracer with about 10-fold higher specific activity than usual.

    29. Molecular Capsules

      Micelle-like Molecular Capsules with Anthracene Shells as Photoactive Hosts (pages 2308–2312)

      Kei Kondo, Akira Suzuki, Prof. Dr. Munetaka Akita and Dr. Michito Yoshizawa

      Article first published online: 23 JAN 2013 | DOI: 10.1002/anie.201208643

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      Aromatic micelles: Hydrophobic and aromatic–aromatic interactions promoted the spontaneous formation of micelle-inspired molecular capsules with large aromatic shells from bent bisanthracene amphiphiles (see picture). The micellar capsules could accommodate fluorescent-dye guests in water, and the resultant nanocomposites exhibited strong fluorescence through efficient energy transfer from the host shells to the encapsulated guests.

    30. Red Phosphorus

      High-Pressure Chemistry of Red Phosphorus and Water under Near-UV Irradiation (pages 2313–2317)

      Dr. Matteo Ceppatelli, Prof. Roberto Bini, Dr. Maria Caporali and Dr. Maurizio Peruzzini

      Article first published online: 11 JAN 2013 | DOI: 10.1002/anie.201208684

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      A high-pressure job: Under high-pressure conditions, within a diamond anvil cell, irradiation of red phosphorus (see scheme, orange) and water was found to lead to a reaction that gives H2, PH3, H3PO2, H3PO4, and H3PO4 (H gray, O red, P orange). This reaction can be easily monitored using Raman spectroscopy and presents an interesting method for H2 generation.

    31. Nanosize Bioconjugates

      pH-Responsive Nutraceutical–Mesoporous Silica Nanoconjugates with Enhanced Colloidal Stability (pages 2318–2322)

      Rémy Guillet-Nicolas, Dr. Amirali Popat, Dr. Jean-Luc Bridot, Prof. Gregory Monteith, Prof. Shi Zhang Qiao and Prof. Freddy Kleitz

      Article first published online: 15 JAN 2013 | DOI: 10.1002/anie.201208840

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      An innovative platform for targeted oral drug delivery is proposed based on the functionalization of drug/dye-loaded mesoporous silica nanoparticles (MSNs) with a biodegradable nutraceutical (β-lactoglobulin). The attachment of the nutraceutical not only protects the drug/dye from leaching in acidic environment, but also effectively allows their release in desired basic sites (pH 7.4).

    32. Fluorescent Sensors

      Monitoring of Protein Arginine Deiminase Activity by Using Fluorescence Quenching: Multicolor Visualization of Citrullination (pages 2323–2325)

      Prof. Qunzhao Wang, Prof. Melanie A. Priestman and Prof. David S. Lawrence

      Article first published online: 21 JAN 2013 | DOI: 10.1002/anie.201208464

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      Colorful: The protein arginine deiminases are members of the enzyme family that catalyze posttranslational histone modification and consequent changes in gene expression. A visual readout of catalytic activity was developed that yields large fluorescence changes across the visible spectrum. The use of different fluorophores (see picture) enables the simultaneous multicolor monitoring of a mixture of histone-modifying enzymes.

    33. Anode Nanotubes

      Naturally Rolled-Up C/Si/C Trilayer Nanomembranes as Stable Anodes for Lithium-Ion Batteries with Remarkable Cycling Performance (pages 2326–2330)

      Junwen Deng, Dr. Hengxing Ji, Dr. Chenglin Yan, Jiaxiang Zhang, Wenping Si, Dr. Stefan Baunack, Dr. Steffen Oswald, Prof. Yongfeng Mei and Prof. Oliver G. Schmidt

      Article first published online: 22 JAN 2013 | DOI: 10.1002/anie.201208357

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      Rolling their own: Naturally rolled-up C/Si/C trilayer nanomembranes (see scheme) exhibit a high reversible capacity of about 2000 mAh g−1 at 50 mA g−1, and 100 % capacity retention at 500 mA g−1 after 300 cycles. This technique is general and could be applied to the fabrication of other battery materials that undergo large volume changes.

    34. Gas-Phase Tautomers

      All Five Forms of Cytosine Revealed in the Gas Phase (pages 2331–2334)

      Prof. José L. Alonso, Dr. Vanesa Vaquero, Dr. Isabel Peña, Prof. Juan C. López, Santiago Mata and Prof. Walther Caminati

      Article first published online: 22 JAN 2013 | DOI: 10.1002/anie.201207744

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      Give me five! All five tautomers and conformers of cytosine were characterized in the gas phase by laser ablation molecular beam Fourier transform microwave spectroscopy. The spectra were assigned unambiguously on the basis of the hyperfine structure due to the three 14N nuclei (see picture; N blue, O red). The relative energies of the identified species were estimated from the relative intensities of the spectra.

    35. Single-Chain Technology

      Synthesis of Single-Chain Sugar Arrays (pages 2335–2339)

      Nathalie Baradel, Dr. Sébastien Fort, Dr. Sami Halila, Dr. Nezha Badi and Dr. Jean-François Lutz

      Article first published online: 23 JAN 2013 | DOI: 10.1002/anie.201209052

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      Polymers that toe the line: Well-defined linear polystyrene chains containing precisely positioned hexose moieties (mannose, galactose, and N-acetylglucosamine) were synthesized by a sequence-controlled polymerization approach followed by a series of site-selective modification steps. Such multifunctional single-chain hexose arrays associate specifically with complementary lectins (see picture).

    36. Drug Discovery

      Discovery of Hepatitis C Virus NS3 Helicase Inhibitors by a Multiplexed, High-Throughput Helicase Activity Assay Based on Graphene Oxide (pages 2340–2344)

      Hongje Jang, Soo-Ryoon Ryoo, Young-Kwan Kim, Soojin Yoon, Henna Kim, Prof. Dr. Sang Woo Han, Prof. Dr. Byong-Seok Choi, Prof. Dr. Dong-Eun Kim and Prof. Dr. Dal-Hee Min

      Article first published online: 25 JAN 2013 | DOI: 10.1002/anie.201209222

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      A GO-to solution: A simple graphene oxide (GO)-based assay to screen for selective inhibitors of a hepatitis C virus (HCV) helicase along with inhibitors of a severe acute respiratory syndrome coronavirus (SARS CoV) helicase was tested (see scheme). A single screen found five inhibitors highly selective for the HCV helicase orthologous to the SARS CoV helicase. Some of these hits were validated using the same GO-based assay.

    37. Protein–RNA Interactions

      Protein–RNA Interfaces Probed by 1H-Detected MAS Solid-State NMR Spectroscopy (pages 2345–2349)

      Sam Asami, Magdalena Rakwalska-Bange, Dr. Teresa Carlomagno and Prof. Dr. Bernd Reif

      Article first published online: 18 JAN 2013 | DOI: 10.1002/anie.201208024

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      Both protonated and deuterated samples were employed in the study of the L7Ae box C/D RNA complex by 1H-detected solid-state NMR spectroscopy. This approach yielded high-resolution spectra and was used to determine the intermolecular interface and extract structural parameters with high accuracy.

    38. Noncovalent Interactions

      The Supramolecular Balance for Transition-Metal Complexes: Assessment of Noncovalent Interactions in Phosphoramidite Palladium Complexes (pages 2350–2354)

      Dr. Evelyn Hartmann and Prof. Dr. Ruth M. Gschwind

      Article first published online: 11 JAN 2013 | DOI: 10.1002/anie.201208021

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      The virtue of enantiomers: A general method has been developed for measuring the individual contributions of noncovalent interactions within transition-metal complexes and dissecting them from electronic effects. On Pd complexes with one enantiopure and two enantiomeric phosphoramidite ligands, it was experimentally shown that modulations in extended CH–π and π–π interaction interfaces provide a ΔΔG value that is significant for stereoselection.

    39. Printed Electronics

      From Paper to Structured Carbon Electrodes by Inkjet Printing (pages 2355–2358)

      Stefan Glatzel, Dr. Zoë Schnepp and Dr. Cristina Giordano

      Article first published online: 17 JAN 2013 | DOI: 10.1002/anie.201207693

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      Electrodes from the ink-jet printer: Cellulose sheets can be transformed into mesostructured graphene nanostructures by a simple and general method. Since the iron catalyst can be printed on paper with an ink-jet printer, the products can be prepared with 2D patterns. Subsequent Cu deposition results in further functionalization of the microstructured electrodes (see picture).

    40. Alkane Oxidation

      Direct Oxidation of Cycloalkanes to Cycloalkanones with Oxygen in Water (pages 2359–2363)

      Svenja Staudt, Edyta Burda, Carolin Giese, Christina A. Müller, Dr. Jan Marienhagen, Prof. Dr. Ulrich Schwaneberg, Prof. Dr. Werner Hummel, Prof. Dr. Karlheinz Drauz and Prof. Dr. Harald Gröger

      Article first published online: 21 JAN 2013 | DOI: 10.1002/anie.201204464

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      It doesn′t take much to oxidize cycloalkanes directly to the corresponding cyclic ketones: molecular oxygen as the oxidant, water as the solvent, the cofactor NADP+ (and a little 2-propanol to reduce it), as well as two catalytic enzymes—a hydroxylating P450 monooxygenase and an alcohol dehydrogenase (see scheme).

    41. Biological Mass Spectrometry

      You have full text access to this OnlineOpen article
      Liquid AP-UV-MALDI Enables Stable Ion Yields of Multiply Charged Peptide and Protein Ions for Sensitive Analysis by Mass Spectrometry (pages 2364–2367)

      Prof. Rainer Cramer, Alexander Pirkl, Prof. Franz Hillenkamp and Prof. Klaus Dreisewerd

      Article first published online: 22 JAN 2013 | DOI: 10.1002/anie.201208628

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      All charged up: High and prolonged yields of multiply charged peptide and protein ions can be formed in MALDI mass spectrometry using liquid UV-MALDI matrices and a heated ion-transfer tube. The key features are low laser energies of 1–10 μJ, resulting in fluences of less than 200 to 2000 J m−2 and low sample ablation, high sensitivity, and continuous ion generation over tens of thousands of laser shots.

    42. Interaction Energy

      Dissecting Anion–Cation Interaction Energies in Protic Ionic Liquids (pages 2368–2372)

      Dr. Koichi Fumino, Verlaine Fossog, Dipl.-Chem. Kai Wittler, Prof. Dr. Rolf Hempelmann and Prof. Dr. Ralf Ludwig

      Article first published online: 16 JAN 2013 | DOI: 10.1002/anie.201207065

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      The strength of the interaction between anions and cations in protic ionic liquids (PILs) can be extracted from far-IR spectra. A suitable set of specially synthesized PILs was used to correct the frequency shifts of these low vibrational modes for contributions resulting from changing reduced masses only. The experimental results were confirmed by DFT calculations.

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