Angewandte Chemie International Edition

Cover image for Vol. 53 Issue 3

January 13, 2014

Volume 53, Issue 3

Pages 601–887

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Essay
    12. Minireviews
    13. Review
    14. Communications
    1. You have free access to this content
      Cover Picture: Modular Synthesis of Triarylmethanes through Palladium-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone (Angew. Chem. Int. Ed. 3/2014) (page 601)

      Dr. Masakazu Nambo and Dr. Cathleen M. Crudden

      Article first published online: 8 JAN 2014 | DOI: 10.1002/anie.201310510

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      Triarylmethanes were prepared in three steps from phenyl methyl sulfone, as described by M. Nambo and C. M. Crudden in their Communication on page 742 ff. After two selective C[BOND]H arylation reactions, the third aromatic ring was introduced through a novel arylative desulfonation. This sequence permits the synthesis of a wide variety of unsymmetric triarylmethanes from a simple, readily available starting material.

    2. You have free access to this content
      Inside Cover: Infrared Detection of Criegee Intermediates Formed during the Ozonolysis of β-Pinene and Their Reactivity towards Sulfur Dioxide (Angew. Chem. Int. Ed. 3/2014) (page 602)

      Jennifer Ahrens, Philip T. M. Carlsson, Nils Hertl, Prof. Dr. Matthias Olzmann, Mark Pfeifle, Dr. J. Lennard Wolf and Dr. Thomas Zeuch

      Article first published online: 8 JAN 2014 | DOI: 10.1002/anie.201310818

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      Criegee intermediates mark the beginning of a reaction chain that leads to atmospheric new particle formation events, which can promote cloud formation and influence the climate. In their Communication on page 715 ff., T. Zeuch et al. report the infrared detection of large, biogenic Criegee intermediates formed during the gas-phase ozonolysis of β-pinene. The detection was achieved at the reactive center of the intermediates, using the strong absorption band of the O–O stretching mode. (Photo: Monika Hoffstätter-Müncheberg)

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      Inside Back Cover: Shape-Dependent Optoelectronic Cell Lysis (Angew. Chem. Int. Ed. 3/2014) (page 891)

      Clemens Kremer, Christian Witte, Dr. Steven L. Neale, Dr. Julien Reboud, Prof. Michael P. Barrett and Prof. Jonathan M. Cooper

      Article first published online: 8 JAN 2014 | DOI: 10.1002/anie.201310757

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      Red blood cells are illuminated with red light on an optoelectronic device, causing them to experience an electrical field that induces lysis. In their Communication on page 842 ff., J. M. Cooper et al. demonstrate that the shape of the cells has a large effect on the strength of field they experience, as the field lines are distorted by the presence of the cells. Disc-shaped red blood cells experience higher electrical potentials than the larger but spherical white blood cells.

    4. You have free access to this content
      Back Cover: Rhodium-Catalyzed Ketone Methylation Using Methanol Under Mild Conditions: Formation of α-Branched Products (Angew. Chem. Int. Ed. 3/2014) (page 892)

      Dr. Louis K. M. Chan, Darren L. Poole, Di Shen, Dr. Mark P. Healy and Prof. Timothy J. Donohoe

      Article first published online: 8 JAN 2014 | DOI: 10.1002/anie.201310758

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      The α-methylation of ketones using methanol as the carbon source is described in the Communication by T. J. Donohoe et al. on page 761 ff. The reaction of a carbonyl compound, a base, a catalytic amount of rhodium, and methanol in an atmosphere of oxygen allows the alkylation to proceed at 65 °C. The use of an iridium/rhodium catalyst combination facilitates a double cycle of alkylation reactions, which transforms methyl ketones into more highly substituted compounds.

  2. Editorial

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Essay
    12. Minireviews
    13. Review
    14. Communications
    1. You have free access to this content
  3. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Essay
    12. Minireviews
    13. Review
    14. Communications
    1. Graphical Abstract: Angew. Chem. Int. Ed. 3/2014 (pages 607–621)

      Article first published online: 8 JAN 2014 | DOI: 10.1002/anie.201490001

  4. Corrigendum

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Essay
    12. Minireviews
    13. Review
    14. Communications
    1. You have free access to this content
      Corrigendum: Anthracimycin, a Potent Anthrax Antibiotic from a Marine-Derived Actinomycete (page 621)

      Dr. Kyoung Hwa Jang, Dr. Sang-Jip Nam, Dr. Jeffrey B. Locke, Christopher A. Kauffman, Deanna S. Beatty, Lauren A. Paul and Prof. Dr. William Fenical

      Article first published online: 8 JAN 2014 | DOI: 10.1002/anie.201310144

      This article corrects:

      Anthracimycin, a Potent Anthrax Antibiotic from a Marine-Derived Actinomycete1

      Vol. 52, Issue 30, 7822–7824, Article first published online: 17 JUN 2013

  5. News

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Essay
    12. Minireviews
    13. Review
    14. Communications
  6. Author Profile

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Essay
    12. Minireviews
    13. Review
    14. Communications
    1. Weihong Tan (page 626)

      Article first published online: 13 NOV 2013 | DOI: 10.1002/anie.201307442

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      “My favorite quote is: “imagination is more important than knowledge” (Einstein). If I could be any age I would be I would be same age, but young at heart. …” This and more about Weihong Tan can be found on page 626.

  7. News

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Essay
    12. Minireviews
    13. Review
    14. Communications
  8. Book Review

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Essay
    12. Minireviews
    13. Review
    14. Communications
    1. Cross Coupling and Heck-Type Reactions. Workbench Three-Volume Set. Edited by Gary A. Molander, John P. Wolfe, and Mats Larhed. (page 629)

      Henri Doucet

      Article first published online: 11 DEC 2013 | DOI: 10.1002/anie.201308796

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      Thieme, Stuttgart, 2013. 2720 pp., softcover, € 649.00.—ISBN 978-3131734112

  9. Highlights

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Essay
    12. Minireviews
    13. Review
    14. Communications
    1. Nitrogen Fixation

      Catalytic Ammonia Synthesis in Homogeneous Solution—Biomimetic at Last? (pages 632–634)

      Henning Broda and Prof. Dr. Felix Tuczek

      Article first published online: 29 NOV 2013 | DOI: 10.1002/anie.201308780

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      New iron dinitrogen complexes are crucial to a catalytic ammonia synthesis in homogeneous solution and establish new structural motifs related to the iron–molybdenum cofactor of the enzyme nitrogenase (see scheme; BArF= B[3,5-(CF3)2C6H3]4). These findings are put into the context of 50 years of synthetic nitrogen fixation and latest developments regarding the crystal structure and the molecular mechanism of nitrogenase.

    2. Photovoltaics

      New Light on an Old Story: Perovskites Go Solar (pages 635–637)

      Prof. Bettina V. Lotsch

      Article first published online: 18 DEC 2013 | DOI: 10.1002/anie.201309368

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      All in one: Perovskites are currently undergoing a renaissance as “allrounder” materials for solar cells. For a special type of methylammonium lead halide perovskites, a unique combination of properties, including high charge-carrier mobilities, exciton lifetimes, and panchromatic absorption, was observed, which renders this class of hybrid perovskites one of the most promising absorber and ambipolar charge-transport materials for all-solid-state solar cells.

  10. Essay

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Essay
    12. Minireviews
    13. Review
    14. Communications
    1. History of Science

      Chemical Crystallography before X-ray Diffraction (pages 638–652)

      Dr. Krešimir Molčanov and Dr. Vladimir Stilinović

      Article first published online: 17 SEP 2013 | DOI: 10.1002/anie.201301319

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      2012/2013 mark the 100th anniversary of von Laue's diffraction of X-rays from single crystals of copper sulfate, the postulation of Bragg's law, and the solution of the first X-ray structure. However, even before 1912, the study of crystals was an integral part of chemistry and it played a major role in development of modern chemical science, including key concepts such as atoms, molecules, isomerism, and chirality.

  11. Minireviews

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Essay
    12. Minireviews
    13. Review
    14. Communications
    1. Inorganic Crystal Structures

      Which Inorganic Structures are the Most Complex? (pages 654–661)

      Prof. Dr. Sergey V. Krivovichev

      Article first published online: 13 DEC 2013 | DOI: 10.1002/anie.201304374

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      Cause and complexity: Analysis of inorganic crystal structures using information-based complexity measures indicates that structural complexity is generated by the assembly of nanoscale building blocks, modularity induced by complex chemical compositions, and the formation of superlattices as a result of local atomic ordering or displacive phase transitions.

    2. Structural Databases

      The Cambridge Structural Database in Retrospect and Prospect (pages 662–671)

      Dr. Colin R. Groom and Dr. Frank H. Allen

      Article first published online: 2 JAN 2014 | DOI: 10.1002/anie.201306438

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      Crystal-clear data: The Cambridge Crystallographic Data Centre (CCDC) was established in 1965; its core product, the Cambridge Structural Database (CSD), stores numerical, chemical, and bibliographic data for nearly 700 000 crystal structures. As X-ray crystallography celebrates its centenary, the CCDC nears its own 50th anniversary. The origins of the CCDC and development of the CSD system is presented. The CCDC's funding model in relation to open access paradigms is also considered.

  12. Review

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Essay
    12. Minireviews
    13. Review
    14. Communications
    1. Crystal Growth

      Growth Actuated Bending and Twisting of Single Crystals (pages 672–699)

      Dr. Alexander G. Shtukenberg, Prof. Yurii O. Punin, Ankit Gujral and Prof. Bart Kahr

      Article first published online: 2 JAN 2014 | DOI: 10.1002/anie.201301223

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      Twisted crystals: Crystals of many substances, including hippuric acid (see picture), will bend or twist as they grow under some conditions. These deviations are often activated by particular additives. How and why so many materials choose dramatic non-crystallographic distortions is analyzed for molecular crystals, high polymers, minerals, elements, and salts.

  13. Communications

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Essay
    12. Minireviews
    13. Review
    14. Communications
    1. Weak Interactions

      Self-Assembly and (Hydro)gelation Triggered by Cooperative π–π and Unconventional C[BOND]H⋅⋅⋅X Hydrogen Bonding Interactions (pages 700–705)

      Christina Rest, Dr. María José Mayoral, Dr. Katharina Fucke, Jennifer Schellheimer, Dr. Vladimir Stepanenko and Dr. Gustavo Fernández

      Article first published online: 18 DEC 2013 | DOI: 10.1002/anie.201307806

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      Growing hand in hand! Multiple unconventional C[BOND]H⋅⋅⋅X (X=O, Cl) hydrogen-bonding interactions, assisted by π–π interactions, are strong enough to drive the cooperative formation of supramolecular polymers and gels in polar and aqueous media. The aggregates consolidate themselves in the crystals, as shown by combined studies in solution and crystalline state.

    2. Luminescent Thin Films

      Highly Luminescent Thin Films of the Dense Framework 3[EuIm2] with Switchable Transparency Formed by Scanning Femtosecond-Pulse Laser Deposition (pages 706–710)

      Dr. Dieter Fischer, Larissa V. Meyer, Prof. Dr. Martin Jansen and Prof. Dr. Klaus Müller-Buschbaum

      Article first published online: 2 DEC 2013 | DOI: 10.1002/anie.201305648

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      A scanning laser ablation technique with a femtosecond laser was used to deposit highly luminescent thin films of the dense framework 3[EuIm2]. The polycrystalline films can be switched between transparent with visible light and nontransparent upon excitation with UV light due to the intrinsic luminescence of the hybrid material. This new PLD method is a suitable new approach for the preparation of coatings consisting of framework compounds and coordination polymers.

    3. Sequence-Controlled Polymers

      Sequence Control in Polymer Chemistry through the Passerini Three-Component Reaction (pages 711–714)

      Susanne C. Solleder and Prof. Dr. Michael A. R. Meier

      Article first published online: 4 DEC 2013 | DOI: 10.1002/anie.201308960

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      The iterative application of the Passerini three-component reaction and the thiol–ene addition reaction provides sequence-defined macromolecules without the utilization of any protecting group.

    4. Atmospheric Chemistry

      Infrared Detection of Criegee Intermediates Formed during the Ozonolysis of β-Pinene and Their Reactivity towards Sulfur Dioxide (pages 715–719)

      Jennifer Ahrens, Philip T. M. Carlsson, Nils Hertl, Prof. Dr. Matthias Olzmann, Mark Pfeifle, Dr. J. Lennard Wolf and Dr. Thomas Zeuch

      Article first published online: 8 JAN 2014 | DOI: 10.1002/anie.201307327

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      How is sulfuric acid formed in the troposphere? One route is the oxidation of SO2 by hydroxyl radicals. Now, the relevance of an alternative path, oxidation of SO2 by reaction with large, biogenic Criegee intermediates, has been proven. Criegee intermediates are formed along with a carbonyl compound in the ozonolysis of alkenes. This study was conducted with β-pinene and its possible Criegee intermediates are shown.

    5. Silicon-Stereogenic Aminomethoxysilanes

      Stereoselective Synthesis of Silicon-Stereogenic Aminomethoxysilanes: Easy Access to Highly Enantiomerically Enriched Siloxanes (pages 720–724)

      Dipl.-Chem. Jonathan O. Bauer and Prof. Dr. Carsten Strohmann

      Article first published online: 2 DEC 2013 | DOI: 10.1002/anie.201307826

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      Broad access to silicon-stereogenic N,O-functionalized organosilanes in optically pure form is provided by a highly chemo- and diastereoselective substitution on aminodimethoxysilanes. The novel compounds could be further transformed stereoselectively with alcohols and a silanol and are predestined as building blocks for a controlled development of chiral siloxane units.

    6. Photo Meerwein Addition

      You have full text access to this OnlineOpen article
      The Photoredox-Catalyzed Meerwein Addition Reaction: Intermolecular Amino-Arylation of Alkenes (pages 725–728)

      M. Sc. Durga Prasad Hari, M. Sc. Thea Hering and Prof. Dr. Burkhard König

      Article first published online: 4 DEC 2013 | DOI: 10.1002/anie.201307051

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      From elimination to addition: A variety of amides are efficiently accessible under mild conditions by intermolecular amino-arylation using a photo Meerwein addition with visible light. The reaction has a broad substrate scope, tolerates a large range of functional groups, and was applied to the synthesis of 3-aryl-3,4-dihydroisoquinoline.

    7. Ferromagnetism

      Unexpected Room-Temperature Ferromagnetism in Nanostructured Bi2Te3 (pages 729–733)

      Dr. Guanjun Xiao, Dr. Chunye Zhu, Prof. Yanming Ma, Prof. Bingbing Liu, Prof. Guangtian Zou and Prof. Bo Zou

      Article first published online: 4 DEC 2013 | DOI: 10.1002/anie.201309416

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      Research with BiTe: Intriguing room-temperature ferromagnetism can be observed in a nanostructured topological insulator, Bi2Te3, without introducing any exotic magnetic dopants. These findings may pave the way for developing Bi2Te3-based dissipationless spintronics and fault-tolerant quantum computing.

    8. C[BOND]H Activation

      Palladium-Catalyzed ortho-Selective C[BOND]H Deuteration of Arenes: Evidence for Superior Reactivity of Weakly Coordinated Palladacycles (pages 734–737)

      Dr. Sandy Ma, Dr. Giorgio Villa, Peter S. Thuy-Boun, Anna Homs and Prof. Dr. Jin-Quan Yu

      Article first published online: 29 NOV 2013 | DOI: 10.1002/anie.201305388

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      Weaker is better! Phenylacetic acids and benzoic acids are suitable substrates for a palladium-catalyzed ortho-selective C[BOND]H deuteration of arenes with deuterated acetic acid (see scheme; R=H, alkyl, CF3, OMe, NO2, Cl, F). This reaction demonstrates the superior reactivity of weakly coordinated palladacycle intermediates in C[BOND]H functionalization reactions.

    9. Solid-State Nitrogen

      Production of N3 upon Photolysis of Solid Nitrogen at 3 K with Synchrotron Radiation (pages 738–741)

      Sheng-Lung Chou, Dr. Jen-Iu Lo, Meng-Yeh Lin, Yu-Chain Peng, Dr. Hsiao-Chi Lu and Dr. Bing-Ming Cheng

      Article first published online: 29 NOV 2013 | DOI: 10.1002/anie.201306876

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      Now on solid ground: Irradiation of pure solid nitrogen at 3 K with vacuum-ultraviolet light generated product l-N3. This formation possibly occurs through an activated complex l-N4 upon photoexcitation.

    10. Palladium Catalysis

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      Modular Synthesis of Triarylmethanes through Palladium-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone (pages 742–746)

      Dr. Masakazu Nambo and Dr. Cathleen M. Crudden

      Article first published online: 4 DEC 2013 | DOI: 10.1002/anie.201307019

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      Unsymmetric triarylmethanes have been synthesized starting from methyl phenyl sulfone as an inexpensive and readily available template. The three aryl groups were installed through two sequential palladium-catalyzed C[BOND]H arylation reactions, followed by an arylative desulfonation.

    11. Gold Complexes

      Direct Evidence for Intermolecular Oxidative Addition of σ(Si[BOND]Si) Bonds to Gold (pages 747–751)

      Maximilian Joost, Dr. Pauline Gualco, Dr. Yannick Coppel, Dr. Karinne Miqueu, Dr. Christos E. Kefalidis, Dr. Laurent Maron, Dr. Abderrahmane Amgoune and Dr. Didier Bourissou

      Article first published online: 4 DEC 2013 | DOI: 10.1002/anie.201307613

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      Oxidative addition is the most elusive elementary step in reactions with gold. Now, evidence for the intermolecular oxidative addition of σ(Si[BOND]Si) bonds is reported. Phosphine gold chlorides readily reacted with disilanes at low temperature in the presence of GaCl3. The ensuing bis(silyl) gold(III) complexes were characterized by 31P and 29Si NMR spectroscopy, and their structures were analyzed by DFT calculations.

    12. Alcohol Deoxygenation

      Copper-Catalyzed Reduction of Alkyl Triflates and Iodides: An Efficient Method for the Deoxygenation of Primary and Secondary Alcohols (pages 752–756)

      Hester Dang, Nick Cox and Gojko Lalic

      Article first published online: 4 DEC 2013 | DOI: 10.1002/anie.201307697

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      Primarily reduced: The copper-catalyzed reduction of 1° alkyl sulfonates, and 1° and 2° iodides, which is effective in the presence of a wide range of functional groups, provides a means for the effective deoxygenation of alcohols. A preliminary study of the reaction mechanism suggests that the reduction does not involve free-radical intermediates.

    13. Natural Product Synthesis

      Total Synthesis of (−)-Ophiodilactone A and (−)-Ophiodilactone B (pages 757–760)

      Takaaki Matsubara, Dr. Keisuke Takahashi, Dr. Jun Ishihara and Prof. Dr. Susumi Hatakeyama

      Article first published online: 11 DEC 2013 | DOI: 10.1002/anie.201307835

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      Bioinspired synthesis: The first total synthesis of the title compounds has been accomplished in a highly stereocontrolled manner. Key features of the synthesis include an asymmetric epoxidation, a diastereoselective iodolactonization, an intramolecular epoxide opening with a carboxylic acid, and a biomimetic radical cyclization of ophiodilactone A to ophiodilactone B.

    14. Ketone Alkylation

      You have full text access to this OnlineOpen article
      Rhodium-Catalyzed Ketone Methylation Using Methanol Under Mild Conditions: Formation of α-Branched Products (pages 761–765)

      Dr. Louis K. M. Chan, Darren L. Poole, Di Shen, Dr. Mark P. Healy and Prof. Timothy J. Donohoe

      Article first published online: 29 NOV 2013 | DOI: 10.1002/anie.201307950

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      Uniquely effective for making branched alkyl products from ketones (see scheme): The scope of the presented reaction includes aromatic and aliphatic ketones and consecutive one-pot double alkylation reactions to provide a convenient route to branched ketones from simple methyl ketones. A brief study into the mechanism of the reaction has given evidence for an aldol-based reaction pathway.

    15. Organocatalysis

      Stereocontrol of All-Carbon Quaternary Centers through Enantioselective Desymmetrization of Meso Primary Diols by Organocatalyzed Acyl Transfer (pages 766–770)

      Christèle Roux, Dr. Mathieu Candy, Prof. Dr. Jean-Marc Pons, Dr. Olivier Chuzel and Dr. Cyril Bressy

      Article first published online: 6 DEC 2013 | DOI: 10.1002/anie.201308268

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      Smashing the mirror: The symmetry breaking of meso primary diols was employed to control all-carbon quaternary stereocenters using catalytic asymmetric acyl transfer. The planar chiral Fu DMAP catalyst was used to reach a high degree of enantioselectivity (up to 97:3 e.r.) through a synergic effect, combining a desymmetrization step and a kinetic resolution.

    16. Sustainable Chemistry

      Carbon Dioxide Capture and Use: Organic Synthesis Using Carbon Dioxide from Exhaust Gas (pages 771–774)

      Seung Hyo Kim, Kwang Hee Kim and Prof. Dr. Soon Hyeok Hong

      Article first published online: 4 DEC 2013 | DOI: 10.1002/anie.201308341

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      Exhaust gas is good enough! Carbon dioxide captured directly from exhaust gas was used for organic syntheses (see picture) as efficiently as hyper-pure CO2 gas from a commercial source, even for highly air- and moisture-sensitive reactions. The CO2 capturing aqueous ethanolamine solution could be recycled continuously without any diminished reaction efficiency.

    17. Fluoroalkylation

      Stereoselective Nucleophilic Fluoromethylation of Aryl Ketones: Dynamic Kinetic Resolution of Chiral α-Fluoro Carbanions (pages 775–779)

      Dr. Xiao Shen, Wenjun Miao, Dr. Chuanfa Ni and Prof. Dr. Jinbo Hu

      Article first published online: 4 DEC 2013 | DOI: 10.1002/anie.201308484

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      Fluoromethyl fix: An efficient and easy-to-handle protocol for the stereoselective synthesis of optically pure monofluoromethyl tertiary alcohols was developed, which showed higher facial selectivity than the corresponding difluoromethylation and proceeded via a different type of transition state. Stereoselective control at the fluorinated carbon chiral center is believed to be facilitated by the dynamic kinetic resolution of the chiral α-fluoro carbanions.

    18. Natural Product Synthesis

      Total Synthesis of Pectenotoxin-2 (pages 780–784)

      Prof. Dr. Kenshu Fujiwara, Yuki Suzuki, Nao Koseki, Yu-ichi Aki, Yuta Kikuchi, Shun-ichi Murata, Fuyuki Yamamoto, Mariko Kawamura, Prof. Dr. Toshio Norikura, Prof. Dr. Hajime Matsue, Prof. Dr. Akio Murai, Prof. Dr. Ryo Katoono, Prof. Dr. Hidetoshi Kawai and Prof. Dr. Takanori Suzuki

      Article first published online: 29 NOV 2013 | DOI: 10.1002/anie.201308502

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      A shellfish toxin: Non-anomeric spiroacetal pectenotoxin-2 was synthesized by the acidic isomerization of anomeric spiroacetal pectenotoxin-2b. In the isomerization step, [6,6]-spiroacetal pectenotoxin-2c was the major product at equilibrium. However, the early termination of a dynamic transition process to equilibrium in the step produced pectenotoxin-2 selectively.

    19. Heterocycles

      Dirhodium(II) Carboxylate Catalyzed Formation of 1,2,3-Trisubstituted Indoles from Styryl Azides (pages 785–788)

      Crystalann Jones, Quyen Nguyen and Prof. Dr. Tom G. Driver

      Article first published online: 26 NOV 2013 | DOI: 10.1002/anie.201308611

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      Selective migration of acyl groups in trisubstituted styryl azides leads to the formation of 1,2,3-trisubstituted indoles. The styryl azides are readily available in three steps from cyclobutanone and 2-iodoaniline. esp=α,α,α′,α′-tetramethyl-1,3-benzenedipropionic acid.

    20. Homogeneous Catalysis

      Selective Hydrosilation of CO2 to a Bis(silylacetal) Using an Anilido Bipyridyl-Ligated Organoscandium Catalyst (pages 789–792)

      Francis A. LeBlanc, Prof. Warren E. Piers and Masood Parvez

      Article first published online: 2 DEC 2013 | DOI: 10.1002/anie.201309094

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      Lewis acid shuffle: Selective hydrosilation of CO2 to a bis(silylacetal) is mediated by a scandium-based catalyst activated by B(C6F5)3. The selectivity derives from the ability of the scandium complex to moderate the propensity of borane to further hydrosilate the Et3SiOCH2OSiEt3 product by limiting the amount of free B(C6F5)3 present in solution.

    21. Photocatalysis

      Visible-Light Sensitization of Vinyl Azides by Transition-Metal Photocatalysis (pages 793–797)

      Elliot P. Farney and Prof. Tehshik P. Yoon

      Article first published online: 26 NOV 2013 | DOI: 10.1002/anie.201308820

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      Rock and pyrrole: Irradiation of vinyl and aryl azides with visible light in the presence of Ru photocatalysts results in the formation of reactive nitrenes, which can undergo a variety of C[BOND]N bond-forming reactions. The ability to use low-energy visible light instead of UV in the photochemical activation of azides (see picture) avoids competitive photodecomposition processes.

    22. C[BOND]H Oxidation

      Nonheme Iron Mediated Oxidation of Light Alkanes with Oxone: Characterization of Reactive Oxoiron(IV) Ligand Cation Radical Intermediates by Spectroscopic Studies and DFT Calculations (pages 798–803)

      Chun-Wai Tse, Dr. Toby Wai-Shan Chow, Dr. Zhen Guo, Prof. Dr. Hung Kay Lee, Dr. Jie-Sheng Huang and Prof. Dr. Chi-Ming Che

      Article first published online: 27 NOV 2013 | DOI: 10.1002/anie.201305153

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      Highly reactive {Fe[DOUBLE BOND]O} intermediates, such as [Fe(Tp)2(O)]+ or complex I (see Scheme), are likely to be involved in the oxidation of propane and ethane with oxone that is either mediated by [FeIII(Tp)2]+ (1) or catalyzed by iron complex 2. The cationic intermediate I features an {Fe[DOUBLE BOND]O} moiety and is stabilized by a combination of tridentate and bidentate ligands.

    23. Natural Products Discovery

      Crowdsourcing Natural Products Discovery to Access Uncharted Dimensions of Fungal Metabolite Diversity (pages 804–809)

      Dr. Lin Du, Andrew J. Robles, Jarrod B. King, Dr. Douglas R. Powell, Prof. Dr. Andrew N. Miller, Prof. Dr. Susan L. Mooberry and Prof. Dr. Robert H. Cichewicz

      Article first published online: 27 NOV 2013 | DOI: 10.1002/anie.201306549

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      A fungus among us: A new Tolypocladium sp. was obtained through a crowdsourcing initiative. The expression of a silent biosynthetic pathway in this fungus was triggered through chemical epigenetics, culture medium manipulation, and co-culture to yield the unique polyketide-shikimate-NRPS-hybrid compound, maximiscin, which demonstrated in vivo antitumor activity. NRPS=non-ribosomal peptide synthetase.

    24. Intracellular Localization

      You have full text access to this OnlineOpen article
      Lactose as a “Trojan Horse” for Quantum Dot Cell Transport (pages 810–814)

      Dr. David Benito-Alifonso, Shirley Tremel, Bo Hou, Harriet Lockyear, Dr. Judith Mantell, Prof. David J. Fermin, Dr. Paul Verkade, Dr. Monica Berry and Dr. M. Carmen Galan

      Article first published online: 5 DEC 2013 | DOI: 10.1002/anie.201307232

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      With a spoonful of sugar… Glycan-coated quantum dots were used to probe the effect of glycan presentation in intracellular localization in HeLa and SV40 epithelial cells. Glycan density was found to mostly impact cell toxicity, whereas glycan type affects cell uptake and intracellular localization. Also, lactose was found to help the intracellular delivery of other non-internalizable glycan moieties.

    25. Metal–Organic Frameworks

      Symmetry-Guided Synthesis of Highly Porous Metal–Organic Frameworks with Fluorite Topology (pages 815–818)

      Muwei Zhang, Ying-Pin Chen, Mathieu Bosch, Thomas Gentle III, Kecheng Wang, Dawei Feng, Dr. Zhiyong U. Wang and Prof. Dr. Hong-Cai Zhou

      Article first published online: 11 NOV 2013 | DOI: 10.1002/anie.201307340

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      Meet me at the symmetry gates: Using a symmetry-guided design strategy, two stable, non-interpenetrated MOFs, were synthesized by augmenting the fluorite topology with tetrahedral linkers, thus expanding the cavity size (see scheme) and giving the largest pore size of any MOF with tetrahedral ligands.

    26. Molecular Magnets

      You have full text access to this OnlineOpen article
      A Uranium-Based UO2+–Mn2+ Single-Chain Magnet Assembled trough Cation–Cation Interactions (pages 819–823)

      Dr. Victor Mougel, Lucile Chatelain, Dr. Johannes Hermle, Dr. Roberto Caciuffo, Dr. Eric Colineau, Dr. Floriana Tuna, Dr. Nicola Magnani, Dr. Arnaud de Geyer, Dr. Jacques Pécaut and Dr. Marinella Mazzanti

      Article first published online: 6 DEC 2013 | DOI: 10.1002/anie.201307366

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      Uranium in chains: 5f–3d heterometallic 1D chains are assembled from the reaction of pentavalent uranyl and CdII or MnII. The Mn-UO2-Mn coordination polymer exhibits slow relaxation of magnetization with a high relaxation barrier, and shows an open hysteresis cycle, thus affording the first example of an actinide-based single-chain magnet.

    27. Natural Product Biosynthesis

      Conversion of a Disulfide Bond into a Thioacetal Group during Echinomycin Biosynthesis (pages 824–828)

      Dr. Kinya Hotta, Dr. Ronan M. Keegan, Soumya Ranganathan, Minyi Fang, Dr. Jaclyn Bibby, Dr. Martyn D. Winn, Dr. Michio Sato, Mingzhu Lian, Prof. Dr. Kenji Watanabe, Dr. Daniel J. Rigden and Prof. Dr. Chu-Young Kim

      Article first published online: 2 DEC 2013 | DOI: 10.1002/anie.201307404

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      Disulfide to thioacetal: The S-adenosyl-L-methionine (SAM)-dependent methyltransferase Ecm 18 converts the disulfide bond of triostin A into a thioacetal linkage to form echinomycin. The 1.50 Å crystal structure of Ecm 18 in complex with its reaction products S-adenosyl-L-homocysteine (SAH) and echinomycin provides insight into how Ecm 18 catalyzes this unusual transformation.

    28. Molecular Recognition

      Highly Stereoselective Recognition and Deracemization of Amino Acids by Supramolecular Self-Assembly (pages 829–832)

      Dr. Soon Mog So, Kimia Moozeh, Dr. Alan J. Lough and Prof. Jik Chin

      Article first published online: 27 NOV 2013 | DOI: 10.1002/anie.201307410

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      A communal effort: A chiral guanidine derivative 1 and a chiral aldehyde 2 underwent self-assembly with amino acids to promote inversion of the stereogenic center of the guest (see scheme). The supramolecular self-assembly exhibited high stereoselectivity for amino acid recognition and was found to be useful for the separation of racemic mixtures of amino acids as well as for their deracemization.

    29. Heterogeneous Catalysis

      A Reusable Unsupported Rhenium Nanocrystalline Catalyst for Acceptorless Dehydrogenation of Alcohols through γ-C–H Activation (pages 833–836)

      Jing Yi, Prof. Dr. Jeffrey T. Miller, Dr. Dmitry Y. Zemlyanov, Ruihong Zhang, Dr. Paul J. Dietrich, Prof. Dr. Fabio H. Ribeiro, Dr. Sergey Suslov and Prof. Dr. Mahdi M. Abu-Omar

      Article first published online: 26 NOV 2013 | DOI: 10.1002/anie.201307665

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      Active particles: A rhenium nanoparticle (Re NP) catalyst is generated from NH4ReO4 under mild solution conditions in neat 3-octanol at 180 °C. The resulting Re NPs catalyze acceptorless dehydrogenation of alcohols through a novel C–H activation pathway, and are fully recyclable.

    30. Metal–Organic Frameworks

      A Mixed Molecular Building Block Strategy for the Design of Nested Polyhedron Metal–Organic Frameworks (pages 837–841)

      Dan Tian, Qiang Chen, Dr. Yue Li, Dr. Ying-Hui Zhang, Dr. Ze Chang and Prof. Dr. Xian-He Bu

      Article first published online: 26 NOV 2013 | DOI: 10.1002/anie.201307681

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      MOF in a MOF: The integration of two size-matching C3-symmetric ligands with different rigidities leads to two porous metal–organic frameworks built from unprecedented double-walled metal–organic octahedra. A new and reliable mixed molecular building block strategy for the synthesis of cage-within-cage materials is provided.

    31. Cell lysis

      You have full text access to this OnlineOpen article
      Shape-Dependent Optoelectronic Cell Lysis (pages 842–846)

      Clemens Kremer, Christian Witte, Dr. Steven L. Neale, Dr. Julien Reboud, Prof. Michael P. Barrett and Prof. Jonathan M. Cooper

      Article first published online: 8 JAN 2014 | DOI: 10.1002/anie.201307751

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      Selective lysis of specific cells in a mixture of different cell types is based upon the shape of the cells, a phenomenon that is explained by the electrical “shadow” that is cast by the cells. The technique is implemented on an optoelectronic platform, where light, focused onto a semiconductor surface by a projector, creates a reconfigurable pattern of electrodes over large areas. RBCs and WBCs are red and white blood cells, respectively, and a-Si is amorphous silicon.

    32. Bioluminescence

      Why is Firefly Oxyluciferin a Notoriously Labile Substance? (pages 847–850)

      Dr. Oleg V. Maltsev, Dr. Naba K. Nath, Prof. Dr. Panče Naumov and Prof. Dr. Lukas Hintermann

      Article first published online: 26 NOV 2013 | DOI: 10.1002/anie.201307972

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      Light into the darkness: Firefly oxyluciferin, the emitter of firefly bioluminescence, is notoriously difficult to handle. The cause behind its chemical lability is now ascribed to autodimerization of the coexisting enol (showing blue fluorescence in DMSO) and keto forms (contributing to the green fluorescence in water) in a Mannich reaction.

    33. Peptides

      You have full text access to this OnlineOpen article
      Efficient Amide Bond Formation through a Rapid and Strong Activation of Carboxylic Acids in a Microflow Reactor (pages 851–855)

      Dr. Shinichiro Fuse, Yuto Mifune and Prof. Takashi Takahashi

      Article first published online: 2 DEC 2013 | DOI: 10.1002/anie.201307987

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      In the fast lane: The title reaction is described for the synthesis of peptides. Various carboxylic acids including easily epimerizable amino acids were rapidly converted into highly electrophilic species, and then reacted with various amines, including less nucleophilic N-methyl amino acids, to afford the desired peptides in high yields without significant epimerization.

    34. Surface Chemistry

      Salt-Induced Fabrication of Superhydrophilic and Underwater Superoleophobic PAA-g-PVDF Membranes for Effective Separation of Oil-in-Water Emulsions (pages 856–860)

      Wenbin Zhang, Yuzhang Zhu, Xia Liu, Dr. Dong Wang, Prof. Jingye Li, Prof. Lei Jiang and Prof. Jian Jin

      Article first published online: 4 DEC 2013 | DOI: 10.1002/anie.201308183

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      Salting away: The title membranes having different PAA graft ratios were fabricated by using a salt-induced phase-inversion process. The membrane can separate both surfactant-free and surfactant-stabilized oil-in-water emulsions under either a small applied pressure (0.1 bar) or gravity, with a high separation efficiency and high flux. CA=contact angle.

    35. Asymmetric Gold Catalysis

      Helicenes with Embedded Phosphole Units in Enantioselective Gold Catalysis (pages 861–865)

      Keihann Yavari, Paul Aillard, Yang Zhang, Dr. Frédérick Nuter, Dr. Pascal Retailleau, Dr. Arnaud Voituriez and Dr. Angela Marinetti

      Article first published online: 6 DEC 2013 | DOI: 10.1002/anie.201308377

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      A twist of gold: Phosphahelicenes were for the first time used as chiral ligands in transition-metal catalysis. Unlike all helical phosphines used so far in catalysis, the phosphorus atom of phosphahelicenes is embedded within the helical structure (see scheme). Structural design allowed both high catalytic activity and good ee values to be attained in gold-promoted cycloisomerizations of N-tethered 1,6-enynes and dienynes.

    36. Plasmon-Enhanced Fluorescence

      Probing Distance-Dependent Plasmon-Enhanced Near-Infrared Fluorescence Using Polyelectrolyte Multilayers as Dielectric Spacers (pages 866–870)

      Dr. Naveen Gandra, Christopher Portz, Limei Tian, Dr. Rui Tang, Dr. Baogang Xu, Prof. Samuel Achilefu and Prof. Srikanth Singamaneni

      Article first published online: 2 DEC 2013 | DOI: 10.1002/anie.201308516

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      A simple and effective approach to probe distance-dependent plasmon-enhanced fluorescence is developed using polyelectrolyte multilayers to design ultrabright flurophores for near-infrared imaging (see picture). By carefully choosing the plasmonic nanostructures and chromophores with the corresponding maximum spectral overlap, a variety of ultrabright fluorescence probes can be designed.

    37. CO2 Reduction

      High-Yield Electrochemical Production of Formaldehyde from CO2 and Seawater (pages 871–874)

      Prof. Kazuya Nakata, Takuya Ozaki, Prof. Chiaki Terashima, Prof. Akira Fujishima and Prof. Yasuaki Einaga

      Article first published online: 26 NOV 2013 | DOI: 10.1002/anie.201308657

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      Boron is a diamond's best friend: A boron-doped diamond (BDD) electrode exhibited very high Faradaic efficiency (74 %) for the production of formaldehyde using either methanol, aqueous NaCl, or seawater as the electrolyte at room temperature and ambient pressure.

    38. Photoactivatable Agents

      Tunable Visible and Near-IR Photoactivation of Light-Responsive Compounds by Using Fluorophores as Light-Capturing Antennas (pages 875–878)

      Prof. Thomas A. Shell, Prof. Jennifer R. Shell, Zachary L. Rodgers and Prof. David S. Lawrence

      Article first published online: 27 NOV 2013 | DOI: 10.1002/anie.201308816

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      See it split: A palette of photoresponsive agents is described in which the desired activating wavelength is encoded with readily available fluorophores. Photomanipulation is feasible throughout the visible range into the near IR, and in a manner that provides orthogonal control over multiple species. This technology has been used to trigger 1) interorganelle trafficking, 2) disassembly of stress fibers, and 3) light-dose-dependent cell death.

    39. Carbophilic Catalysts

      Gold Carbenoids: Lessons Learnt from a Transmetalation Approach (pages 879–882)

      Ing. Günter Seidel, Barbara Gabor, Dr. Richard Goddard, Dipl.-Ing. Berit Heggen, Prof. Walter Thiel and Prof. Alois Fürstner

      Article first published online: 27 NOV 2013 | DOI: 10.1002/anie.201308842

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      I do not want to be free! Whereas prototype Fischer-type chromium carbene complexes transfer their organic ligand to gold with exceptional ease, chromium complexes devoid of the heteroelement substituent do not want to release unstabilized gold carbenoids of the type that is often invoked in mechanistic discussions of π-acid catalysis. Instead, unusual bimetallic arrays are formed in which charge density gets delocalized over several positions.

    40. Foldamer–Protein Interactions

      Structure of a Complex Formed by a Protein and a Helical Aromatic Oligoamide Foldamer at 2.1 Å Resolution (pages 883–887)

      Jérémie Buratto, Dr. Cinzia Colombo, Dr. Marine Stupfel, Dr. Simon J. Dawson, Dr. Christel Dolain, Dr. Béatrice Langlois d'Estaintot, Dr. Lucile Fischer, Dr. Thierry Granier, Dr. Michel Laguerre, Dr. Bernard Gallois and Dr. Ivan Huc

      Article first published online: 29 NOV 2013 | DOI: 10.1002/anie.201309160

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      To design a foldamer that binds to a protein surface, a strategy is proposed that uses a known protein ligand to tether the foldamer to the protein surface. Candidates are first screened for induced circular dichroism in presence of the protein. Then, structural information about foldamer–protein interactions is collected before strong binding is established. The crystal structure of human carbonic anhydrase (A, B chains) with helical aromatic amide foldamers (stick models) is shown.

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