Angewandte Chemie International Edition

Cover image for Vol. 50 Issue 37

September 5, 2011

Volume 50, Issue 37

Pages 8439–8759

  1. Cover Picture

    1. Top of page
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    5. German Research Foundation (DFG)
    6. Editorial
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    8. Corrigendum
    9. News
    10. Author Profile
    11. News
    12. Book Reviews
    13. Highlights
    14. Essay
    15. Minireview
    16. Reviews
    17. Communications
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    1. Cover Picture: Transformation of Carbon Dioxide with Homogeneous Transition-Metal Catalysts: A Molecular Solution to a Global Challenge? (Angew. Chem. Int. Ed. 37/2011) (page 8439)

      Dr. Mirza Cokoja, Dipl.-Chem. Christian Bruckmeier, Prof. Dr. Bernhard Rieger, Prof. Dr. Wolfgang A. Herrmann and Prof. Dr. Fritz E. Kühn

      Article first published online: 1 SEP 2011 | DOI: 10.1002/anie.201104738

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      The activation of carbon dioxide is one of the major tasks of catalysis today. CO2 is a ubiquitous and cheap C1 feedstock for the synthesis of raw and fine chemicals, yet its use as a reactant in industrial synthesis is comparatively scarce. The transformation of CO2 into acids, esters, lactones, and polymers with molecular transition-metal catalysts is a future alternative application. B. Rieger, F. E. Kühn et al. present the current catalysts and products in their Review on page 8510 ff.

  2. Inside Cover

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    1. Inside Cover: Stable Hexacenes through Nitrogen Substitution (Angew. Chem. Int. Ed. 37/2011) (page 8440)

      Dipl.-Chem. Benjamin D. Lindner, Jens U. Engelhart, Olena Tverskoy, Dr. Anthony Lucas Appleton, Dr. Frank Rominger, Dipl.-Chem. Anastasia Peters, Prof. Hans-Jörg Himmel and Prof. Uwe H. F. Bunz

      Article first published online: 1 SEP 2011 | DOI: 10.1002/anie.201105551

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      Using nitrogen atoms in the perimeter of a hexacene will make the compound considerably more stable than its all-hydrocarbon relative. In their Communication on page 8588 ff, U. H. F. Bunz and co-workers report the synthesis of a tetraaza- and a hexaazahexacene using a palladium-catalyzed cross-coupling of a suitable diaminoanthracene or diaminophenazine derivative with dichloroquinoxaline. The obtained materials are potentially attractive for applications in organic electronics.

  3. Back Cover

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    14. Essay
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    1. Back Cover: Stereospecific Palladium-Catalyzed Decarboxylative C(sp3)[BOND]C(sp2) Coupling of 2,5-Cyclohexadiene-1-carboxylic Acid Derivatives with Aryl Iodides (Angew. Chem. Int. Ed. 37/2011) (page 8440)

      Dr. Chih-Ming Chou, Indranil Chatterjee and Prof. Dr. Armido Studer

      Article first published online: 20 JUL 2011 | DOI: 10.1002/anie.201104737

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      Decarboxylation of aryl, allyl, and alkyl metal carboxylates, which are readily accessible from carboxylic acids, offers an attractive approach for the generation of the corresponding organometallic compounds. In their Communication on page 8614 ff., A. Studer and co-workers report on highly stereospecific decarboxylative palladations of 2,5-cyclohexadiene-1-carboxylic acids. Stereoselective arylation of these intermediates delivers optically active arylated cyclohexadienes.

  4. German Research Foundation (DFG)

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  5. Editorial

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      Educating Chemists for the Future (pages 8442–8443)

      Prof. Peter Atkins

      Article first published online: 1 SEP 2011 | DOI: 10.1002/anie.201104842

  6. Graphical Abstract

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    1. Graphical Abstract: Angew. Chem. Int. Ed. 37/2011 (pages 8445–8458)

      Article first published online: 1 SEP 2011 | DOI: 10.1002/anie.201190073

  7. Corrigendum

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      Corrigendum: Asymmetric Total Synthesis of (−)-Cribrostatin 4 (Renieramycin H) (page 8458)

      Dr. Guillaume Vincent and Prof. Robert M. Williams

      Article first published online: 1 SEP 2011 | DOI: 10.1002/anie.201190074

      This article corrects:

      Asymmetric Total Synthesis of (−)-Cribrostatin 4 (Renieramycin H)1

      Vol. 46, Issue 9, 1517–1520, Article first published online: 19 JAN 2007

  8. News

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  9. Author Profile

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    1. Paul Floreancig (page 8468)

      Article first published online: 30 AUG 2011 | DOI: 10.1002/anie.201103836

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      “If I could be any age I would be 47. No point in fretting about the passage of time. The biggest challenge facing scientists is reversing the growing sense from the general public that science is not a worthy area of pursuit …” This and more about Paul Floreancig can be found on page 8468.

  10. News

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  11. Book Reviews

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    1. Energy Production and Storage. Inorganic Chemistry Strategies for a Warming World. Edited by Robert H. Crabtree. (pages 8471–8472)

      Sebastiano Campagna

      Article first published online: 27 JUL 2011 | DOI: 10.1002/anie.201103012

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      John Wiley & Sons, Hoboken 2010. 428 pp., hardcover, € 149.00.—ISBN 978-0470749869

    2. Artificial Receptors for Chemical Sensors. Edited by Vladimir M. Mirsky and Anatoly Yatsimirsky. (pages 8472–8473)

      Werner Nau, Alexandra I. Lazar and Sweccha Joshi

      Article first published online: 16 AUG 2011 | DOI: 10.1002/anie.201103816

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      Wiley-VCH, Weinheim 2011. 470 pp., hardcover, € 139.00.—ISBN 978-3527323579

  12. Highlights

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    1. Tetracycline Antibiotics

      Isoxazole Functionalization Technologies Enable Construction of Tetracycline Derivatives (pages 8474–8477)

      Dr. Brian Heasley

      Article first published online: 29 JUN 2011 | DOI: 10.1002/anie.201102480

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      Reactive response: Tetracyclines are potent antimicrobial agents—however, their high consumption level has contributed to the emergence of widespread bacterial resistance, which in turn stimulates the systematic search for new tetracycline analogues. In recent years, new synthetic methods have emerged that provide access to a broad range of tetracycline analogues.

    2. Alkyne Metathesis

      Towards Highly Active and Robust Alkyne Metathesis Catalysts: Recent Developments in Catalyst Design (pages 8478–8480)

      Dr. Kuthanapillil Jyothish and Prof. Dr. Wei Zhang

      Article first published online: 22 JUL 2011 | DOI: 10.1002/anie.201102678

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      Switch it up: Recent developments in alkyne metathesis catalysts are described, with particular emphasis on the rational design of ligands that can improve the catalyst activity and stability (see scheme; M=W, Mo; R=CR′, N) by probing the electrophilicity and the substrate binding sites at the transition-metal center.

  13. Essay

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    1. Responsibility in Science

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      Ethics, Chemistry, and Education for Sustainability (pages 8482–8490)

      Prof. Dr. Hartmut Frank, Prof. Dr. Luigi Campanella, Prof. Dr. Francesco Dondi, Jan Mehlich, Dr. Erich Leitner, Dr.-Ing. Giuseppe Rossi, Dr. Karine Ndjoko Ioset and Prof. Dr. Gerhard Bringmann

      Article first published online: 27 JUL 2011 | DOI: 10.1002/anie.201007599

      Why do scientists avoid considerations about ethics and categorically deny precautionary principles? Is it because they do not adequately understand the emotional needs and fears of the general public? The authors argue that a central challenge in chemical education is conveying the philosophy of empathy; without it, the exclusively intellectual training of chemists results in heartless individuals who forget human needs and dreams. In addition, concrete examples are given from a course in applied ethics for chemistry students and a scholarship program in the Congo.

  14. Minireview

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    1. One-Pot Reactions

      A Simple Recipe for Sophisticated Cocktails: Organocatalytic One-Pot Reactions—Concept, Nomenclature, and Future Perspectives (pages 8492–8509)

      Dr. Łukasz Albrecht, Hao Jiang and Prof. Dr. Karl Anker Jørgensen

      Article first published online: 8 AUG 2011 | DOI: 10.1002/anie.201102522

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      It′s great, but what shall we call it? Asymmetric organocatalysis has been successfully incorporated in many multistep one-pot sequences (see picture; A–G are reagents). In this Minireview, an easy-to-use classification system for the systematic and informative description of one-pot reactions is introduced. Selected important contributions within the field of organocatalytic one-pot reactions are reviewed according to this new system.

  15. Reviews

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    1. CO2 Activation

      Transformation of Carbon Dioxide with Homogeneous Transition-Metal Catalysts: A Molecular Solution to a Global Challenge? (pages 8510–8537)

      Dr. Mirza Cokoja, Dipl.-Chem. Christian Bruckmeier, Prof. Dr. Bernhard Rieger, Prof. Dr. Wolfgang A. Herrmann and Prof. Dr. Fritz E. Kühn

      Article first published online: 29 AUG 2011 | DOI: 10.1002/anie.201102010

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      Renewable carbon resources, such as carbon dioxide, are of enormous interest as an entry into industrially relevant chemicals, such as formic or salicylic acids, urea, and (poly)carbonates. This Review highlights the use of CO2 as a C1 feedstock as well as its transformation with homogeneous molecular transition-metal catalysts.

    2. Alkaloid Synthesis

      The Pictet–Spengler Reaction in Nature and in Organic Chemistry (pages 8538–8564)

      Prof. Dr. Joachim Stöckigt, Dr. Andrey P. Antonchick, Fangrui Wu and Prof. Dr. Herbert Waldmann

      Article first published online: 9 AUG 2011 | DOI: 10.1002/anie.201008071

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      100 years ago Pictet and Spengler discovered the most important method for the synthesis of alkaloid scaffolds—the condensation of aryl ethylamines and aldehydes. Today, efficient enzymatic and non-enzymatic methods are both available for the Pictet–Spengler reaction.

    3. Nanofabrication

      Use of Thin Sectioning (Nanoskiving) to Fabricate Nanostructures for Electronic and Optical Applications (pages 8566–8583)

      Dr. Darren J. Lipomi, Dr. Ramses V. Martinez and Prof. George M. Whitesides

      Article first published online: 13 JUL 2011 | DOI: 10.1002/anie.201101024

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      Nanoskiving is a simple and inexpensive method of nanofabrication which makes it possible to fabricate nanostructures from materials, and of geometries, to which more familiar methods of nanofabrication are not applicable. Three steps are required: 1) deposition of a thin film onto an epoxy substrate, 2) embedding this film in an epoxy block, and 3) sectioning the epoxy block into slabs with an ultramicrotome.

  16. Communications

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    1. Protein Engineering

      A Combination of In Vivo Selection and Cell Sorting for the Identification of Enantioselective Biocatalysts (pages 8584–8587)

      Dr. Elena Fernández-Álvaro, Dr. Radka Snajdrova, Dr. Helge Jochens, Dipl.-Biol. Timo Davids, Dr. Dominique Böttcher and Prof. Dr. Uwe T. Bornscheuer

      Article first published online: 3 AUG 2011 | DOI: 10.1002/anie.201102360

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      The “carrot and stick” principle could be combined with cell sorting to enable the selection of enantioselective esterase variants from a mutant library. Hence, the enormous diversity generated in directed evolution experiments is now easily accessible by this high-throughput system. In line with the principle, the hydrolysis of 1 glycerin supports cell growth, whereas the hydrolysis of 2 leads to cell death.

    2. Heteroacenes

      Stable Hexacenes through Nitrogen Substitution (pages 8588–8591)

      Dipl.-Chem. Benjamin D. Lindner, Jens U. Engelhart, Olena Tverskoy, Dr. Anthony Lucas Appleton, Dr. Frank Rominger, Dipl.-Chem. Anastasia Peters, Prof. Hans-Jörg Himmel and Prof. Uwe H. F. Bunz

      Article first published online: 23 AUG 2011 | DOI: 10.1002/anie.201103676

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      Give me an N: Tetraazahexacenes (see picture, N blue, Si brown) are easily prepared in high yields. Their modular synthesis allows the introduction of any substituent by the choice of suitable quinoxaline derivatives.

    3. DNA Complexes

      DNA-Controlled Bivalent Presentation of Ligands for the Estrogen Receptor (pages 8592–8596)

      Frank Abendroth, Alexander Bujotzek, Min Shan, Prof. Dr. Rainer Haag, Dr. Marcus Weber and Prof. Dr. Oliver Seitz

      Article first published online: 26 JUL 2011 | DOI: 10.1002/anie.201101655

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      Molecular ruler: Steroid analogues were conjugated to DNA by using click chemistry, and self-assembly provided ternary DNA complexes with bivalent ligand presentation. The distance between the bound ligands was measured by spatial screening of the estrogen receptor, and a second hydrophobic binding site was postulated. The picture shows the DNA(black)–raloxifene(orange) complex in the ligand binding domain of the receptor.

    4. Membrane Fusion Model

      Transmembrane Domain Peptide/Peptide Nucleic Acid Hybrid as a Model of a SNARE Protein in Vesicle Fusion (pages 8597–8601)

      Antonina S. Lygina, Karsten Meyenberg, Prof. Dr. Reinhard Jahn and Prof. Dr. Ulf Diederichsen

      Article first published online: 22 JUL 2011 | DOI: 10.1002/anie.201101951

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      Artificial models of the natural SNARE proteins containing the native linker regions (light blue/gray) and the transmembrane domains (TMDs) of synatobrevin (Syb, violet) and syntaxis-1A (Sx, orange) along with a peptide nucleic acid (PNA) recognition motif can align with either an antiparallel (see picture) or parallel orientation of the interacting strands. These hybrids induce the hemifusion and partial bilayer fusion of phospholipid vesicles.

    5. Carbohydrate Self-Association

      Protein-like Oligomerization of Carbohydrates (pages 8602–8604)

      Prof. Dr. Thomas Heinze, Dipl.-Chem. Melanie Nikolajski, Dr. Stephan Daus, MSc. Tabot M. D. Besong, Dipl.-Chem. Nico Michaelis, Dr. Peter Berlin, Dr. Gordon A. Morris, Prof. Dr. Arthur J. Rowe and Prof. Dr. Stephen E. Harding

      Article first published online: 22 JUL 2011 | DOI: 10.1002/anie.201103026

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      Sugar can, too: Many proteins form noncovalent and thermodynamically reversible oligomers, which can dictate a protein's functionality. For the first time, the presence of multiple oligomeric forms is shown in a whole class of polymeric carbohydrates, the 6-deoxy-6-aminocelluloses, using analytical ultracentrifugation as a probe.

    6. C[BOND]H Functionalization

      Organocatalytic, Oxidative, Intramolecular C[BOND]H Bond Amination and Metal-free Cross-Amination of Unactivated Arenes at Ambient Temperature (pages 8605–8608)

      Dr. Andrey P. Antonchick, Dr. Rajarshi Samanta, Katharina Kulikov and Jonas Lategahn

      Article first published online: 26 JUL 2011 | DOI: 10.1002/anie.201102984

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      The twinkling of an I: In a new atom-economical and environmentally friendly organocatalytic method for intramolecular C[BOND]H amination, the C[BOND]N bond forms at ambient temperature by abstraction of two atoms of hydrogen; only acetic acid and water are formed as by-products. The method has also been extended to the unprecedented metal-free cross-amination of nonactivated arenes.

    7. Lithium–Oxygen Batteries

      The Lithium–Oxygen Battery with Ether-Based Electrolytes (pages 8609–8613)

      Dr. Stefan A. Freunberger, Yuhui Chen, Nicholas E. Drewett, Dr. Laurence J. Hardwick, Dr. Fanny Bardé and Prof. Peter G. Bruce

      Article first published online: 29 JUL 2011 | DOI: 10.1002/anie.201102357

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      Electrolyte puts up a fight: The electrolyte is one of the greatest challenges facing the development of the non-aqueous Li–O2 battery. Although ether-based electrolytes do from Li2O2 on the first discharge, it is shown by various techniques that they also decompose and that decomposition increases while Li2O2 decreases on cycling (see picture). Thus, these electrolytes are not suitable.

    8. Decarboxylative Coupling

      Stereospecific Palladium-Catalyzed Decarboxylative C(sp3)[BOND]C(sp2) Coupling of 2,5-Cyclohexadiene-1-carboxylic Acid Derivatives with Aryl Iodides (pages 8614–8617)

      Dr. Chih-Ming Chou, Indranil Chatterjee and Prof. Dr. Armido Studer

      Article first published online: 19 JUL 2011 | DOI: 10.1002/anie.201103450

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      Walk on the same side! The title reaction occurs by means of highly stereospecific 1,3-metal migration. The starting carboxylic acids are readily prepared by Birch reduction, and the developed protocol provides an efficient route to enantiomerically pure 5-arylated-1,3-cyclohexadiene derivatives (see scheme).

    9. α,ω-Diarylalkanes

      Iridium-Catalyzed Reactions of ω-Arylalkanols to α,ω-Diarylalkanes (pages 8618–8622)

      Dr. Yasushi Obora, Yuka Anno, Ryuhei Okamoto, Toyomi Matsu-ura and Prof. Dr. Yasutaka Ishii

      Article first published online: 2 AUG 2011 | DOI: 10.1002/anie.201104452

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      The long and the short of it: An atom-economical route to α,ω-diarylalkanes from ω-arylalkanols was achieved by a direct one-step method, or a sequential two-step method depending on the alkyl chain length. The reaction proceeded through the formation of β-methylhydroxy-α,ω-diarylalkanes by dehydrogenation/β-alkylation, followed by dehydrogenation/decarbonylation.

    10. Synthetic Methods

      Indium Tribromide Catalyzed Cross-Claisen Condensation between Carboxylic Acids and Ketene Silyl Acetals Using Alkoxyhydrosilanes (pages 8623–8625)

      Dr. Yoshihiro Nishimoto, Aya Okita, Dr. Makoto Yasuda and Prof. Dr. Akio Baba

      Article first published online: 26 JUL 2011 | DOI: 10.1002/anie.201104140

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      Acylations achieved: The title reaction between carboxylic acids and ketene silyl acetals has been accomplished (see scheme). The additive, (MeO)3SiH, is believed to play an important role in the promotion of the condensation reaction. This reaction system was compatible with a diverse range of functional groups, including alkenes, alkynes, chlorides, alcohols, esters, and nitro groups.

    11. Natural Products

      Concise Total Synthesis of the Frog Alkaloid (−)-205 B (pages 8626–8628)

      Sergey V. Tsukanov and Prof. Dr. Daniel L. Comins

      Article first published online: 26 JUL 2011 | DOI: 10.1002/anie.201103596

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      Highly stereocontrolled: The total synthesis of frog alkaloid (−)-205B features a chiral N-acylpyridinium salt reaction and an unprecedented trifluoroacetic anhydride mediated addition of an allylstannane to a vinylogous amide. The core was assembled using a Tsuji–Trost allylic amination reaction and a ring-closing metathesis. TIPS=triisopropylsilyl.

    12. Total Syntheses of Heimiol A, Hopeahainol D, and Constrained Analogues (pages 8629–8633)

      Prof. Dr. Scott A. Snyder, Nathan E. Wright, Jason J. Pflueger and Steven P. Breazzano

      Article first published online: 26 JUL 2011 | DOI: 10.1002/anie.201103575

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      IDSI to the rescue: Use of a carefully designed cascade process empowered by the unique reagent IDSI [(Et2SI)2Cl⋅SbCl6] provided the entire [3.2.2] bicyclic core of both targets 1 and 2 in a single, stereocontrolled operation. Use of strain energies assisted in the completion of the natural products.

    13. Hypergolic Ionic Liquids

      Generation of Melamine Polymer Condensates upon Hypergolic Ignition of Dicyanamide Ionic Liquids (pages 8634–8637)

      Dr. Konstantin Chingin, Dr. Richard H. Perry, Dr. Steven D. Chambreau, Dr. Ghanshyam L. Vaghjiani and Prof. Richard N. Zare

      Article first published online: 22 JUL 2011 | DOI: 10.1002/anie.201101247

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      The reaction of dicyanamide ionic liquids with nitric acid results in hypergolic ignition and the formation of a stable precipitate. The precipitate consists of cyclic triazines, including melamine and its polymers, such as melam and melem (see scheme). This study introduces a novel approach to the synthesis of cyclic azines without resorting to high temperatures and pressures.

    14. Diels–Alder Reaction

      exo-Selective Asymmetric Diels–Alder Reaction of 2,4-Dienals and Nitroalkenes by Trienamine Catalysis (pages 8638–8641)

      Zhi-Jun Jia, Quan Zhou, Qing-Qing Zhou, Peng-Qiao Chen and Prof. Dr. Ying-Chun Chen

      Article first published online: 22 JUL 2011 | DOI: 10.1002/anie.201102013

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      Raising the HOMO: 2,4-Dienals can react with nitroalkenes in trienamine-catalyzed asymmetric Diels–Alder reactions (see scheme). Crucial for the success is raising the HOMO energy of the diene through the introduction of appropriate substituents. The reaction exhibits unusually high enantioselectivity and exo selectivity; endo addition is possibly disfavored because of the electrostatic repulsion shown in the scheme.

    15. Supramolecular Chemistry

      Softening and Hardening of Macro- and Nano-Sized Organic Cocrystals in a Single-Crystal Transformation (pages 8642–8646)

      Dr. Chandana Karunatilaka, Dejan-Krešimir Bučar, Lindsay R. Ditzler, Dr. Tomislav Friščić, Dale C. Swenson, Prof. Dr. Leonard R. MacGillivray and Prof. Dr. Alexei V. Tivanski

      Article first published online: 20 JUL 2011 | DOI: 10.1002/anie.201102370

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      AFM nanoindentation was used to demonstrate that millimeter- and nanometer-sized organic cocrystals exhibit changes in the mechanical properties before, during, and after a single-crystal-to-single-crystal [2+2] photodimerization of olefins. Millimeter-sized crystals become 40 % softer, whereas nanocrystals of the same material become 40 % harder following the photoreaction.

    16. C[BOND]H Amination

      Palladium(0)-Catalyzed Intermolecular Amination of Unactivated Cmath image[BOND]H Bonds (pages 8647–8651)

      Dr. Jun Pan, Mingjuan Su and Prof. Dr. Stephen L. Buchwald

      Article first published online: 2 AUG 2011 | DOI: 10.1002/anie.201102880

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      Filling out the space: The title reaction of unactivated Cmath image[BOND]H bonds using aryl amines as the nitrogen source is disclosed (see scheme; dba=dibenzylideneacetone, Tf=trifluoromethanesulfonyl). Either the C[BOND]N cross-coupling product or the C[BOND]H amination product could be accessed selectively by adjusting the steric environment of the substrate.

    17. Photocatalysis

      Direct Oxygenation of Benzene to Phenol Using Quinolinium Ions as Homogeneous Photocatalysts (pages 8652–8655)

      Dr. Kei Ohkubo, Takaki Kobayashi and Prof. Dr. Shunichi Fukuzumi

      Article first published online: 1 AUG 2011 | DOI: 10.1002/anie.201102931

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      Photocatalytic oxygenation of benzene with oxygen and water to phenol has been achieved under ambient conditions by using the 3-cyano-1-methylquinolinium ion as a photocatalyst (see picture). The mechanism was clarified by detecting the π-dimer benzene radical cation produced by photoinduced electron transfer from benzene to the photocatalyst, and by monitoring the reaction of the radical cations with water molecules.

    18. Asymmetric Catalysis

      Copper-Catalyzed Asymmetric Allylic Substitution of Allyl Phosphates with Aryl- and Alkenylboronates (pages 8656–8659)

      Dr. Ryo Shintani, Dr. Keishi Takatsu, Momotaro Takeda and Prof. Dr. Tamio Hayashi

      Article first published online: 26 JUL 2011 | DOI: 10.1002/anie.201103581

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      The asymmetric allylic substitution of allyl phosphates with aryl- and alkenylboronates catalyzed by a copper/N-heterocyclic carbene complex was developed and the γ-substitution products were obtained with high enantioselectivity (see scheme). To account for the observed influence of the reaction parameters a possible catalytic cycle for this process was proposed.

    19. Cross-Coupling

      Highly Regio- and Stereoselective Synthesis of Multialkylated Olefins through Carbozirconation of Alkynylboronates and Sequential Negishi and Suzuki–Miyaura Coupling Reactions (pages 8660–8664)

      Prof. Dr. Yasushi Nishihara, Yoshiaki Okada, Jiao Jiao, Masato Suetsugu, Ming-Tzu Lan, Megumi Kinoshita, Prof. Dr. Masayuki Iwasaki and Prof. Dr. Kentaro Takagi

      Article first published online: 9 AUG 2011 | DOI: 10.1002/anie.201103601

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      Two Nobel couplings: The synthesis of tri- and tetraalkylated olefins has been achieved (see scheme). These multialkylated olefins were prepared by the zirconocene-mediated carbometalation of 1-alkynylboronates and subsequent sequential C[BOND]C bond formation with Negishi and Suzuki–Miyaura cross-coupling reactions using β-hydrogen-containing alkylzinc reagents and alkyl electrophiles as coupling partners.

    20. Asymmetric Catalysis

      Enantioselective Michael/Mannich Polycyclization Cascade of Indolyl Enones Catalyzed by Quinine-Derived Primary Amines (pages 8665–8669)

      Quan Cai, Chao Zheng, Jun-Wei Zhang and Prof. Dr. Shu-Li You

      Article first published online: 26 JUL 2011 | DOI: 10.1002/anie.201103937

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      Three′s a crowd: The title reaction provides a tetracylic core bearing three chiral centers (see scheme; Ts=4-toluenesulfonyl) with excellent enantioselectivity and good diastereoselectivity. The reaction was used to efficiently construct the (+)-kreysiginine skeleton.

    21. Shape-Memory Polymers

      Nanoparticle Netpoints for Shape-Memory Polymers (pages 8670–8673)

      Praveen Agarwal, Madhur Chopra and Prof. Lynden A. Archer

      Article first published online: 2 AUG 2011 | DOI: 10.1002/anie.201103908

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      Forget-me-not: Nanoparticle fillers in shape-memory polymers usually improve mechanical properties at the expense of shape-memory performance. A new approach overcomes these drawbacks by cross-linking the functionalized poly(ethylene glycol) tethers on silica nanoparticles (see picture).

    22. Asymmetric Catalysis

      Actuation of Asymmetric Cyclopropanation Catalysts: Reversible Single-Crystal to Single-Crystal Reduction of Metal–Organic Frameworks (pages 8674–8678)

      Joseph M. Falkowski, Cheng Wang, Sophie Liu and Prof. Wenbin Lin

      Article first published online: 8 AUG 2011 | DOI: 10.1002/anie.201104086

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      To and fro: Chiral metal–organic frameworks (CMOFs) derived from redox-active ruthenium/salen building blocks exhibited reversible single-crystal to single-crystal reduction and reoxidation. The catalytically inactive RuIII CMOFs (green; see picture) were reduced to RuII CMOFs (red) that were highly active for the asymmetric cyclopropanation of alkenes with very high diastereo- and enantioselectivities.

    23. Solid-State Reactions

      Solid-State Redox Solutions: Microfabrication and Electrochemistry (pages 8679–8682)

      Dezhi Yang, Lianhuan Han, Yang Yang, Liu-Bin Zhao, Cheng Zong, Yi-Fan Huang, Prof. Dr. Dongping Zhan and Prof. Dr. Zhong-Qun Tian

      Article first published online: 26 JUL 2011 | DOI: 10.1002/anie.201103386

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      On solid ground: Mix-valent iron hexacyanides (FeIII, FeII, and Prussian blue) can replace NaCl crystal lattice units to form a solid-state solution. A scanning electrochemical microcapillary (SECM) technique has been developed for the controllable microfabrication of the microcrystals. In situ confocal Raman spectra can also be obtained without exposure to any liquid environment. WE=working electrode, RE/CE=reference/counter electrode.

    24. Nanoparticles in Ionic Liquids

      Solvation and Stabilization of Metallic Nanoparticles in Ionic Liquids (pages 8683–8687)

      Alfonso S. Pensado and Prof. Agílio A. H. Pádua

      Article first published online: 29 JUL 2011 | DOI: 10.1002/anie.201103096

      Thumbnail image of graphical abstract

      Not thick-skinned: The solvation of a metallic nanoparticle in the ionic liquid [C4C1im][Ntf2] was investigated by molecular simulation with a specific interaction potential. The interfacial layer of ionic liquid is only one ion thick, and thus excludes a stabilization mechanism based on an electrostatic double layer.

    25. Nanomaterials

      Genetic Engineering of Biomimetic Nanocomposites: Diblock Proteins, Graphene, and Nanofibrillated Cellulose (pages 8688–8691)

      Dr. Päivi Laaksonen, Dr. Andreas Walther, Jani-Markus Malho, Markku Kainlauri, Prof. Olli Ikkala and Prof. Markus B. Linder

      Article first published online: 22 JUL 2011 | DOI: 10.1002/anie.201102973

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      A tough nut: A new approach to making biomimetic nanocomposites, involving engineered proteins (see scheme; green and blue), reinforcing graphene sheets (purple), and nanofibrillated cellulose (gray), is presented. The aligned co-assembly of these components leads to a composite with remarkably good mechanical properties, which potentially arises from the role of the adhesive matrix proteins.

    26. Phosphorylation

      A Fluorescent Reporter of the Phosphorylation Status of the Substrate Protein STAT3 (pages 8692–8696)

      Vanessa K. Lacey, Angela R. Parrish, Shuliang Han, Dr. Zhouxin Shen, Prof. Steven P. Briggs, Prof. Yuguo Ma and Prof. Lei Wang

      Article first published online: 29 JUL 2011 | DOI: 10.1002/anie.201102923

      Thumbnail image of graphical abstract

      Roving reporter: A reversible biosensor reports the phosphorylation status of full-length substrate protein STAT3 by genetically incorporating 7-hydroxycoumarin into its phosphotyrosine binding pocket (see picture). A large fluorescence increase with characteristic emission and excitation properties results as a response to phosphorylation of STAT3 in vitro and endogenously in nuclear extracts.

    27. Vibrational Spectroscopy

      Distribution Pattern of Length, Length Uniformity, and Density of TiO32− Quantum Wires in an ETS-10 Crystal Revealed by Laser-Scanning Confocal Polarized Micro-Raman Spectroscopy (pages 8697–8701)

      Dr. Nak Cheon Jeong, Dr. Hyunjin Lim, Prof. Dr. Hyeonsik Cheong and Prof. Dr. Kyung Byung Yoon

      Article first published online: 22 JUL 2011 | DOI: 10.1002/anie.201102846

      Thumbnail image of graphical abstract

      Inner beauty: The titanosilicate molecular sieve ETS-10 has TiO32− quantum wires (QWs) of varying length and local density along the [110] and [1equation image0] directions (see picture). Analysis of the distribution of the QWs within a crystal using laser-scanning confocal polarized micro-Raman spectroscopy shows that they are not distributed evenly but in a symmetrical manner in an interesting pattern.

    28. Hydrogen Bonds

      A Biologically Relevant Co1+⋅⋅⋅H Bond: Possible Implications in the Protein-Induced Redox Tuning of Co2+/Co1+ Reduction (pages 8702–8705)

      Manoj Kumar and Prof. Pawel M. Kozlowski

      Article first published online: 26 JUL 2011 | DOI: 10.1002/anie.201100469

      Thumbnail image of graphical abstract

      Reduced circumstances: A hydrogen bond induced by the Co+ ion has been identified theoretically (see picture). It plays a vital role in explaining the mechanistic base of protein-induced tuning of the Co2+/Co+ redox process, a common catalytic event in a wide variety of methyltransferases and adenosyltransferases.

    29. Patchy Particles

      Patchy, Anisotropic Microspheres with Soft Protein Islets (pages 8706–8708)

      Kaladhar Kamalasanan, Siddharth Jhunjhunwala, Jiamin Wu, Alexandra Swanson, Di Gao and Steven R. Little

      Article first published online: 1 AUG 2011 | DOI: 10.1002/anie.201101217

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      Useful contacts: A new method to achieve regular patterns generates anisotropic, “patchy” microspheres by using interfacial condensation of a liquid mask and the proximity of the particles to their neighbors to determine a mask pattern. The microspheres are separated from the scaffold and labeled with a first protein at non-mask regions (green) followed by removal of the mask and immobilization of a second protein (red).

    30. Biological Nanoparticles

      You have full text access to this OnlineOpen article
      Small-Molecule-Based Nanoassemblies as Inducible Nanoprobes for Monitoring Dynamic Molecular Interactions Inside Live Cells (pages 8709–8713)

      Dr. Sangkyu Lee, Dr. Kyoung Hu Lee, Dr. Jae-Seok Ha, Dr. Seung-Goo Lee and Dr. Tae K. Kim

      Article first published online: 27 JUL 2011 | DOI: 10.1002/anie.201101467

      Thumbnail image of graphical abstract

      Seeing into cells: Genetically engineered, labeled ferritin is used to form biological nanoparticles displaying bait (B) and prey (P) molecules inside cells (see picture). Specific bait–prey interactions induce the interconnected assembly of nanoparticles into nanoclusters on a timescale of seconds. This phenotypic readout with a small molecule as an inducible switch was used to directly visualize dynamic molecular interactions within living cells.

    31. Lasso Peptides

      Introducing Lasso Peptides as Molecular Scaffolds for Drug Design: Engineering of an Integrin Antagonist (pages 8714–8717)

      Dr. Thomas A. Knappe, Dr. Florian Manzenrieder, Dr. Carlos Mas-Moruno, Dr. Uwe Linne, Dr. Florenz Sasse, Prof. Dr. Horst Kessler, Dr. Xiulan Xie and Prof. Dr. Mohamed A. Marahiel

      Article first published online: 2 AUG 2011 | DOI: 10.1002/anie.201102190

      Thumbnail image of graphical abstract

      Tightening the noose: Lasso peptides are a class of stable bacterial peptides with unique characteristics that encourage their application in drug design. Epitope grafting of the integrin binding motif RGD onto the lasso structure of microcin J25 converts the knotted peptide into a nanomolar integrin antagonist (see picture). Engineered lasso peptides can therefore be used for pharmacophore presentation.

    32. Bacteriocin Structure

      The 3D Solution Structure of Thurincin H, a Bacteriocin with Four Sulfur to α-Carbon Crosslinks (pages 8718–8721)

      Clarissa S. Sit, Marco J. van Belkum, Ryan T. McKay, Prof. Randy W. Worobo and Prof. John C. Vederas

      Article first published online: 22 JUL 2011 | DOI: 10.1002/anie.201102527

      Thumbnail image of graphical abstract

      Problem solved: Thurincin H is an antimicrobial peptide with suspected post-translational modifications. MS/MS sequencing identified the residues that were modified, and NMR spectroscopic studies in solution led to the 3D structure of thurincin H, which features four S[BOND]Cα thioether crosslinks (yellow in schematic representation). This structure may be representative of several other bacteriocins with identical masses.

    33. Silicon Nanogaps

      Synthesis of Covalently Linked Molecular Bridges between Silicon Electrodes in CMOS-Based Arrays of Vertical Si/SiO2/Si Nanogaps (pages 8722–8726)

      Prof. Geoffrey J. Ashwell, Dr. Laurie J. Phillips, Dr. Benjamin J. Robinson, Susan A. Barnes, Aled T. Williams, Dr. Barbara Urasinska-Wojcik, Prof. Colin J. Lambert, Dr. Iain M. Grace, Dr. Timothy I. Cox and Dr. Ian C. Sage

      Article first published online: 26 JUL 2011 | DOI: 10.1002/anie.201102791

      Thumbnail image of graphical abstract

      Silicon nanogaps were bridged in situ by grafting 4-ethynylbenzaldehyde to activate the electrodes and coupling 2,6-diaminoanthra-9,10-quinone to link the coatings. The bridged structures exhibit currents of 11–14 nA at 1 V. The process is reversed by soaking in acidified solution, which causes the current to diminish.

    34. DNA Protection

      Transient and Switchable (Triethylsilyl)ethynyl Protection of DNA against Cleavage by Restriction Endonucleases (pages 8727–8730)

      Pavel Kielkowski, Dr. Hana Macíčková-Cahová, Dr. Radek Pohl and Prof. Dr. Michal Hocek

      Article first published online: 29 JUL 2011 | DOI: 10.1002/anie.201102898

      Thumbnail image of graphical abstract

      Restricted access to DNA: (Triethylsilyl)ethynyl-modified 7-deaza-dATP is readily incorporated into DNA by primer extension or polymerase chain reaction using KOD XL polymerase. The silylethynyl- protected DNA resists the cleavage by restriction endonucleases (REs), such as RsaI (see scheme), but after it is treated with NH3, the resulting deprotected DNA is fully cleavable by the REs.

    35. Microfluidics

      One-Step Emulsification of Multiple Concentric Shells with Capillary Microfluidic Devices (pages 8731–8734)

      Dr. Shin-Hyun Kim and Prof. David A. Weitz

      Article first published online: 29 JUL 2011 | DOI: 10.1002/anie.201102946

      Thumbnail image of graphical abstract

      Polymeric onions: A facile method to produce monodisperse multiple emulsion drops of high order is developed using a capillary microfluidic device. Coaxial multiphase flows are stabilized by confinement in microcapillary and emulsified to multiple emulsion drops. The breakup of coaxial interfaces, triggered by the core-drop, facilitates the making of multiple emulsion drops of onionlike configuration.

    36. Protein Substructures

      Impact of Strand Length on the Stability of Parallel-β-Sheet Secondary Structure (pages 8735–8738)

      Dr. Felix Freire, Aaron M. Almeida, Dr. John D. Fisk, Jay D. Steinkruger and Prof. Samuel H. Gellman

      Article first published online: 2 AUG 2011 | DOI: 10.1002/anie.201102986

      Thumbnail image of graphical abstract

      Molecular design can be used to investigate whether the parallel-β-sheet secondary structure is subject to length-dependent cooperative stabilization along the strand direction (see picture). Extending strands by adding high-propensity residues (B) leads to a steady increase in parallel-β-sheet stability, but inclusion of low-propensity residues (A) can negate this stabilization.

    37. Natural Product Synthesis

      Second-Generation Total Synthesis of Spirastrellolide F Methyl Ester: The Alkyne Route (pages 8739–8744)

      Dipl.-Chem. Stefan Benson, Dr. Marie-Pierre Collin, Dipl.-Chem. Alexander Arlt, Barbara Gabor, Dr. Richard Goddard and Prof. Alois Fürstner

      Article first published online: 26 JUL 2011 | DOI: 10.1002/anie.201103270

      Thumbnail image of graphical abstract

      Outlandish: The spiroketal embedded in spirastrellolide F methyl ester is a daring site for ring closure, yet it has allowed the power of catalytic alkyne scission and activation to be showcased (see scheme). An improved strategy for the introduction of the labile side chain was also developed.

    38. G-Quadruplexes

      An Acyclic Oligoheteroaryle That Discriminates Strongly between Diverse G-Quadruplex Topologies (pages 8745–8749)

      Dr. Florian Hamon, Eric Largy, Aurore Guédin-Beaurepaire, Dr. Myriam Rouchon-Dagois, Assitan Sidibe, Dr. David Monchaud, Dr. Jean-Louis Mergny, Prof. Jean-Francois Riou, Dr. Chi-Hung Nguyen and Dr. Marie-Paule Teulade-Fichou

      Article first published online: 2 AUG 2011 | DOI: 10.1002/anie.201103422

      Thumbnail image of graphical abstract

      Feeling groovy: A family of nonmacrocyclic G-quadruplex binders with alternate oxazole and pyridine motifs was prepared. The shown heptacyclic derivative exhibits an unprecedented binding preference for certain quadruplex topologies: it recognizes exclusively the human telomeric quadruplex in Na+ buffer but not in K+ buffer. This unique quadruplex binding profile is strongly dependent on the size of the ligand and may result from groove interactions.

    39. Cell Imaging Technology

      Covalent Protein Labeling with a Lanthanide Complex and Its Application to Photoluminescence Lifetime-Based Multicolor Bioimaging (pages 8750–8752)

      Dr. Shin Mizukami, Taku Yamamoto, Akimasa Yoshimura, Shuji Watanabe and Prof. Kazuya Kikuchi

      Article first published online: 26 JUL 2011 | DOI: 10.1002/anie.201103775

      Thumbnail image of graphical abstract

      Better late … Lanthanide-based time-resolved luminescence imaging of proteins is a promising technology. A novel luminescent lanthanide probe (see picture, TPA-Eu) for mutant β-lactamase-based protein labeling system (BL-tag) is used to selectively image cell-surface proteins (POIs) in the presence of autofluorescent background signals, thus enabling imaging with serum.

    40. Porous Frameworks

      Supercapacitive Energy Storage and Electric Power Supply Using an Aza-Fused π-Conjugated Microporous Framework (pages 8753–8757)

      Dr. Yan Kou, Yanhong Xu, Dr. Zhaoqi Guo and Prof. Dr. Donglin Jiang

      Article first published online: 12 AUG 2011 | DOI: 10.1002/anie.201103493

      Thumbnail image of graphical abstract

      Supercapacitor: A π conjugated microporous polymer with an aza-fused framework is reported. The porous framework is conductive and allows electrolyte ions to move into the pores because of structural features (see picture). The material becomes highly co-operative in the formation of electrostatic charge-separation layers, shows exceptional capacitance in supercapacitive energy storage, provides high energy densities, and offers an excellent cycle life.

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      Article first published online: 1 SEP 2011 | DOI: 10.1002/anie.201190075

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