Angewandte Chemie International Edition

Cover image for Vol. 51 Issue 21

May 21, 2012

Volume 51, Issue 21

Pages 5015–5256

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. Corrigendum
    8. News
    9. Author Profile
    10. News
    11. Book Review
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
    16. Preview
    1. Cover Picture: Chemical Protein Synthesis by Chemoselective α-Ketoacid–Hydroxylamine (KAHA) Ligations with 5-Oxaproline (Angew. Chem. Int. Ed. 21/2012) (page 5015)

      Dr. Vijaya R. Pattabiraman, Ayodele O. Ogunkoya and Prof. Dr. Jeffrey W. Bode

      Version of Record online: 30 MAR 2012 | DOI: 10.1002/anie.201202064

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      Chemoselective ligations of two unprotected protein segments that give a native amide bond are valued reactions for the synthesis of proteins. In their Communication on page 5114 ff., J. W. Bode et al. show that the α-ketoacid—hydroxylamine (KAHA) ligation with 5-oxaproline is an efficient reaction for the synthesis of proteins with unprotected protein segments in aqueous buffers. Prokaryotic ubiquitin-like protein and probable cold shock protein A have been synthesized.

  2. Inside Cover

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    5. Back Cover
    6. Graphical Abstract
    7. Corrigendum
    8. News
    9. Author Profile
    10. News
    11. Book Review
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
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    1. Inside Cover: Photoswitchable Dynamic Magnetic Relaxation in a Well-Isolated {Fe2Co} Double-Zigzag Chain (Angew. Chem. Int. Ed. 21/2012) (page 5016)

      Dr. Da-Peng Dong, Prof. Tao Liu, Dr. Shinji Kanegawa, Dr. Soonchul Kang, Prof. Osamu Sato, Prof. Cheng He and Prof. Chun-Ying Duan

      Version of Record online: 15 MAY 2012 | DOI: 10.1002/anie.201202782

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      A cooperative, reversible charge-transfer-induced spin transition that occurs upon cooling and heating of the well-isolated cyanide-bridged FeIII2CoII double-zigzag chain {[Fe(pzTp)(CN)3]2Co(4-styrylpyridine)2}⋅2H2O⋅2CH3OH (pzTp=tetrakis(pyrazolyl)borate) is described in the Communication by T. Liu, O. Sato, C.-Y. Duan et al. on page 5119 ff. Irradiation of the chain with 532 nm light at 5 K results in a single-chain magnetic behavior with no antiferromagnetic ordering after the irradiation.

  3. Inside Back Cover

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    6. Graphical Abstract
    7. Corrigendum
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    11. Book Review
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
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    1. Inside Back Cover: Rational Construction of an Extrinsic Porous Molecular Crystal with an Extraordinary High Specific Surface Area (Angew. Chem. Int. Ed. 21/2012) (page 5257)

      Dr. Michael Mastalerz and Prof. Dr. Iris M. Oppel

      Version of Record online: 4 MAY 2012 | DOI: 10.1002/anie.201203156

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      Porous molecular crystals are accessible by the directed self-assembly of a molecular organic precursor by hydrogen bonding. As M. Mastalerz and I. M. Oppel describe in their Communication on page 5252 ff., enclosed solvent molecules were removed from the pores, leading to a permanently porous material with a specific surface area of 2796 m2 g−1. The material adsorbs CO2 selectively over CH4, and also adsorbs relatively high amounts of H2.

  4. Back Cover

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    7. Corrigendum
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    10. News
    11. Book Review
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
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    1. Back Cover: How Many Lithium Ions Can Be Inserted onto Fused C6 Aromatic Ring Systems? (Angew. Chem. Int. Ed. 21/2012) (page 5258)

      Xiaoyan Han, Guangyan Qing, Jutang Sun and Taolei Sun

      Version of Record online: 19 APR 2012 | DOI: 10.1002/anie.201202306

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      Carbon-based materials such as graphite, are the most common anodes used in lithium ion batteries, but the fundamental question of how many Li ions can be inserted onto C6 aromatic rings is now solved. In their Communication on page 5147 ff., T. Sun and co-workers use a model compound to demonstrate that each C6 ring can accept up to six Li ions to create Li6/C6 additive complexes through a reversible electrochemical reaction, which results in Li ion insertion capacities of up to nearly 2000 mA h g−1.

  5. Graphical Abstract

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    7. Corrigendum
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    11. Book Review
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
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  6. Corrigendum

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    7. Corrigendum
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    11. Book Review
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
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  7. News

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  8. Author Profile

    1. Top of page
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    7. Corrigendum
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    1. Zuowei Xie (page 5037)

      Version of Record online: 29 MAR 2012 | DOI: 10.1002/anie.201200804

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      “My favorite place on earth is my home town. A good work day begins with a cup of Chinese tea …” This and more about Zuowei Xie can be found on page 5037.

  9. News

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    14. Review
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  10. Book Review

    1. Top of page
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    7. Corrigendum
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    14. Review
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    1. Chemosensors. Principles, Strategies, and Applications. Edited by Binghe Wang and Eric V. Anslyn. (page 5039)

      Franz Dickert

      Version of Record online: 18 APR 2012 | DOI: 10.1002/anie.201201767

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      John Wiley & Sons, Hoboken 2011. 524 pp., hardcover, € 129.00.—ISBN 978-0470592069

  11. Highlights

    1. Top of page
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    6. Graphical Abstract
    7. Corrigendum
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    1. Ligand Design

      Monomeric Linear Diaminocarbene Complexes of Gold(I) Show Merit in Enantioselective Catalysis (pages 5042–5044)

      Prof. Helgard G. Raubenheimer

      Version of Record online: 29 MAR 2012 | DOI: 10.1002/anie.201200739

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      Striking gold: Rather simple aryl substituents are required to convert acyclic diaminocarbenes (ADCs) into useful pseudo-bidentate ligands for monomeric gold(I), which can enantioselectively catalyze a tandem acetylization/cycloisomerization reaction. Tf=trifluoromethanesulfonyl.

    2. Proteinase Inhibitors

      Human α2-Macroglobulin—Another Variation on the Venus Flytrap (pages 5045–5047)

      Dr. Cindy Meyer, Prof. Dr. Winfried Hinrichs and Prof. Dr. Ulrich Hahn

      Version of Record online: 4 APR 2012 | DOI: 10.1002/anie.201201104

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      Trapping proteinases: The mechanism of the nonspecific human proteinase inhibitor α2-macroglobulin (α2M, about 6000 amino acid residues) is reminiscent of a Venus flytrap (see scheme). The structure of α2M was solved recently with a resolution of 4.3 Å even though only one single crystal was available.

    3. Trifluoromethylation

      Tamed Arene and Heteroarene Trifluoromethylation (pages 5048–5050)

      Dr. Tatiana Besset, Dr. Cédric Schneider and Dr. Dominique Cahard

      Version of Record online: 4 APR 2012 | DOI: 10.1002/anie.201201012

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      A tri-ing transformation: The increasingly high demand for trifluoromethylated arenes and heteroarenes is a major challenge that has been addressed through the development of trifluoromethylation reactions. Several effective approaches for late-stage trifluoromethylation, as well as the use of practical and cheap trifluoromethylation reagents, are highlighted.

  12. Minireview

    1. Top of page
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    1. Coordination Chemistry

      Heteroditopic Receptors for Ion-Pair Recognition (pages 5052–5061)

      Dr. Anna J. McConnell and Prof. Paul D. Beer

      Version of Record online: 14 MAR 2012 | DOI: 10.1002/anie.201107244

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      Paired up: Ion-pair recognition is an emerging field of research. This Minireview serves to introduce the topic by exploring the concepts behind ion-pair recognition including cooperativity and heteroditopic receptor design (see picture). The different types and applications of heteroditopic receptors for ion pairs are also discussed.

  13. Review

    1. Top of page
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    1. Cross-Coupling

      Palladium-Catalyzed Cross-Coupling: A Historical Contextual Perspective to the 2010 Nobel Prize (pages 5062–5085)

      Dr. Carin C. C. Johansson Seechurn, Dr. Matthew O. Kitching, Dr. Thomas J. Colacot and Prof. Victor Snieckus

      Version of Record online: 9 MAY 2012 | DOI: 10.1002/anie.201107017

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      The 2010 Nobel Prize in Chemistry was awarded to Richard Heck, Ei-ichi Negishi, and Akira Suzuki for their contributions to the development of Pd-catalyzed C[BOND]C bond forming reactions. This Review traces the historical origins of the reactions these laureates discovered, and follows the three waves of research (see scheme) that led to the systematic evolution of “cross-coupling” and the resultant proliferation of discovery within the field of metal-catalyzed organic transformations to the present time.

  14. Communications

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    1. Supramolecular Chemistry

      Solution-Phase Structures of Gallium-Containing Pyrogallol[4]arene Scaffolds (pages 5086–5091)

      Dr. Harshita Kumari, Dr. Steven R. Kline, Dr. Wei G. Wycoff, Dr. Rick L. Paul, Andrew V. Mossine, Prof. Carol A. Deakyne and Prof. Jerry L. Atwood

      Version of Record online: 18 APR 2012 | DOI: 10.1002/anie.201200209

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      Hollow cylinders: Gallium- and gallium–zinc-seamed pyrogallol[4]arene nanoassemblies were studied in the solution phase through various methods. The results reveal their rearrangement from spheres in the solid state to toroids in solution (see, for example, PgC4GaZn) illustrating the structural flexibility of gallium in the metal-seamed frameworks.

    2. Surface Chemistry

      Electrochemically Induced Surface-Initiated Atom-Transfer Radical Polymerization (pages 5092–5095)

      Bin Li, Dr. Bo Yu, Prof. Wilhelm T. S. Huck, Prof. Feng Zhou and Prof. Weimin Liu

      Version of Record online: 12 APR 2012 | DOI: 10.1002/anie.201201533

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      Polymer brushes: Electrically induced atom-transfer radical polymerization allows polymer brushes to grow in air (see picture). The thickness of the brushes is controlled through the ratio of initiator and applied potential. The monomer solution can be reused, which renders this process promising for the polymerization of specialty monomers and for biocompatible polymer brushes grown on complex substrates.

    3. Surface Catalysis

      Polymerization on Stepped Surfaces: Alignment of Polymers and Identification of Catalytic Sites (pages 5096–5100)

      Dr. Alex Saywell, Jutta Schwarz, Prof. Stefan Hecht and Dr. Leonhard Grill

      Version of Record online: 20 APR 2012 | DOI: 10.1002/anie.201200543

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      Kinky catalysis: Surface defects, such as step edges and kinks, are thought to be the ‘active sites’ that induce site-specific chemical reactions on catalytic materials. The catalytic dissociation of a bromine atom from an organic molecule is shown to occur at kink sites on the stepped Au(10,7,7) surface (see scheme; Br=red). The anisotropic surface also facilitates the production of highly aligned polymers, formed by on-surface covalent coupling of monomer units.

    4. Nanofiber Gels

      Macroscopic-Scale Template Synthesis of Robust Carbonaceous Nanofiber Hydrogels and Aerogels and Their Applications (pages 5101–5105)

      Dr. Hai-Wei Liang, Qing-Fang Guan, Li-Feng Chen, Zhu Zhu, Wen-Jun Zhang and Prof. Shu-Hong Yu

      Version of Record online: 13 APR 2012 | DOI: 10.1002/anie.201200710

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      Robust nanofiber gels: Monolithic hydrogels and aerogels consisting of uniform carbonaceous nanofibers (CNFs) were fabricated on a macroscopic scale (12 L, see picture) by a simple template-directed, hydrothermal carbonization process. The high surface reactivity of the CNFs and high porosity and robust nature of the gels can be exploited in applications such as selective adsorbents and templates for creating functional composite gels.

    5. Coinage-Metal Supramolecules

      Supramolecular Tetrahedra of Phosphines and Coinage Metals (pages 5106–5109)

      Dr. Sang Ho Lim, Yongxuan Su and Prof. Dr. Seth M. Cohen

      Version of Record online: 5 APR 2012 | DOI: 10.1002/anie.201200730

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      Treasure chests: The Group 11 metals CuI, AgI, and AuI form tetrahedral supramolecular clusters with a rigid threefold-symmetric phosphine ligand. These supramolecular clusters, which assemble by metal–phosphine interactions, are the first to form across an entire group of the periodic table. Cu+ green, Ag+ pale blue, Au+ green, I red, P purple.

    6. Synthetic Methods

      Diastereoselective Synthesis of C3-Quaternary Indolenines Using α,β-Unsaturated N-Aryl Ketonitrones and Activated Alkynes (pages 5110–5113)

      C. Bryan Huehls, Tyler S. Hood and Prof. Dr. Jiong Yang

      Version of Record online: 5 APR 2012 | DOI: 10.1002/anie.201200860

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      New trick for an old dog: C3-Quaternary indolenines were synthesized by combining readily available α,β-unsaturated N-aryl ketonitrones and activated alkynes. This remarkably simple and atom-economical transformation does not require transition-metal catalysis and involves the formation of the heterocycles with concomitant generation of two contiguous quaternary and tertiary chiral centers.

    7. Protein Ligations

      Chemical Protein Synthesis by Chemoselective α-Ketoacid–Hydroxylamine (KAHA) Ligations with 5-Oxaproline (pages 5114–5118)

      Dr. Vijaya R. Pattabiraman, Ayodele O. Ogunkoya and Prof. Dr. Jeffrey W. Bode

      Version of Record online: 14 MAR 2012 | DOI: 10.1002/anie.201200907

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      The chemical synthesis of proteins from unprotected peptide segments uses KAHA ligation with 5-oxaproline, which is incorporated readily into peptides by solid-phase peptide synthesis. Ligation of such protein segments in aqueous buffers with an α-ketoacid peptide gives an α-homoserine residue at the ligation site. The new ligation is used for the synthesis of two proteins, prokaryotic-ubiquitin like protein (Pup) and probable cold shock protein A (cspA; see scheme).

      Corrected by:

      Corrigendum: Corrigendum: Chemical Protein Synthesis by Chemoselective α-Ketoacid–Hydroxylamine (KAHA) Ligations with 5-Oxaproline

      Vol. 53, Issue 45, 12005, Version of Record online: 22 SEP 2014

    8. Switchable Materials

      Photoswitchable Dynamic Magnetic Relaxation in a Well-Isolated {Fe2Co} Double-Zigzag Chain (pages 5119–5123)

      Dr. Da-Peng Dong, Prof. Tao Liu, Dr. Shinji Kanegawa, Dr. Soonchul Kang, Prof. Osamu Sato, Prof. Cheng He and Prof. Chun-Ying Duan

      Version of Record online: 12 APR 2012 | DOI: 10.1002/anie.201105987

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      Charge-transfer-induced spin transition occurs cooperatively and reversibly in the isolated FeIII2CoII chains of {[Fe(pzTp)(CN)3]2Co(4-styrylpyridine)2}⋅2 H2O ⋅2 CH3OH (1). When 1 is irradiated with 532 nm light, it shows single-chain magnetic behavior with no antiferromagnetic ordering after irradiation (see picture; C gray, N blue, B yellow; LS=low spin, HS=high spin).

    9. Cerium–Organic Magnets

      Magnetic Ordering in Self-assembled Materials Consisting of Cerium(III) Ions and the Radical Forms of 2,5-TCNQX2 (X=Cl, Br) (pages 5124–5128)

      María Ballesteros-Rivas, Dr. Hanhua Zhao, Dr. Andrey Prosvirin, Eric W. Reinheimer, Rubén A. Toscano, Prof. Jesús Valdés-Martínez and Prof. Kim R. Dunbar

      Version of Record online: 8 MAY 2012 | DOI: 10.1002/anie.201107938

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      Ribbon-like coordination polymers composed of CeIII ions and TCNQX2 (TCNQ=tetracyanoquinodimethane; X=Cl, Br), but not TCNQ radicals, show unexpected magnetic ordering (see picture; Ce green). This behavior reveals remarkable subtlety for magnetic properties of lanthanide–organic materials.

    10. Cool Methane Oxidation

      Direct Catalytic Conversion of Methane to Methanol in an Aqueous Medium by using Copper-Promoted Fe-ZSM-5 (pages 5129–5133)

      Dr. Ceri Hammond, Michael M. Forde, Dr. Mohd Hasbi Ab Rahim, Adam Thetford, Qian He, Dr. Robert L. Jenkins, Dr. Nikolaos Dimitratos, Dr. Jose A. Lopez-Sanchez, Dr. Nicholas F. Dummer, Dr. Damien M. Murphy, Dr. Albert F. Carley, Dr. Stuart H. Taylor, Dr. David J. Willock, Dr. Eric E. Stangland, Dr. Joo Kang, Dr. Henk Hagen, Prof. Christopher J. Kiely and Prof. Graham J. Hutchings

      Version of Record online: 5 APR 2012 | DOI: 10.1002/anie.201108706

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      Iron copper zeolite (Fe-Cu-ZSM-5) with aqueous hydrogen peroxide is active for the selective oxidation of methane to methanol. Iron is involved in the activation of the carbon–hydrogen bond, while copper allows methanol to form as the major product. The catalyst is stable, re-usable and activates methane giving >90 % methanol selectivity and 10 % conversion in a closed catalytic cycle (see scheme).

    11. Prebiotic Synthesis

      A Unified Mechanism for Abiotic Adenine and Purine Synthesis in Formamide (pages 5134–5137)

      Jeremy S. Hudson, Joseph F. Eberle, Raj H. Vachhani, Luther C. Rogers, James H. Wade, Prof. Dr. Ramanarayanan Krishnamurthy and Dr. Greg Springsteen

      Version of Record online: 5 APR 2012 | DOI: 10.1002/anie.201108907

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      Form(am)idable beginning: Mechanistic pathways from formamide to purine and adenine have been proposed (see scheme, purine (R=H, X=H), adenine (R=CN, X=NH2, R′=CONH2). Parallels between these plausible prebiotic syntheses and purine-ring biosynthesis may allude to the origins of the metabolic route.

    12. Sonochemistry

      Generation of a Porous Luminescent Structure Through Ultrasonically Induced Pathways of Silicon Modification (pages 5138–5142)

      Dr. Ekaterina V. Skorb, Dr. Daria V. Andreeva and Prof. Helmuth Möhwald

      Version of Record online: 5 APR 2012 | DOI: 10.1002/anie.201105084

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      Porous silicon with unique optical properties was formed through an ultrasonication method. This technique allows the one-step formation of silicon with a purposefully variable porous structure, provides for the possibility of patterned surface-selective modification, and forms photoluminescent centers and defect states, which can act as centers for charge separation.

    13. Bacterial Toxins

      You have full text access to this OnlineOpen article
      Towards a Structural Basis for the Relationship Between Blood Group and the Severity of El Tor Cholera (pages 5143–5146)

      Dr. Pintu K. Mandal, Thomas R. Branson, Dr. Edward D. Hayes, James F. Ross, Dr. Jose A. Gavín, Dr. Antonio H. Daranas and Dr. W. Bruce Turnbull

      Version of Record online: 5 APR 2012 | DOI: 10.1002/anie.201109068

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      It has long been known that people with blood group O are more severely affected by El Tor cholera than those with blood groups A or B. Microcalorimetry and NMR spectroscopy are used to evaluate the ability of the B-subunits of cholera toxin and E. coli heat-labile toxin to bind to selected blood group oligosaccharides.

    14. Electrode Materials

      How Many Lithium Ions Can Be Inserted onto Fused C6 Aromatic Ring Systems? (pages 5147–5151)

      Xiaoyan Han, Guangyan Qing, Jutang Sun and Taolei Sun

      Version of Record online: 18 APR 2012 | DOI: 10.1002/anie.201109187

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      Getting a charge out of lithium: The naphthalene derivative NTCDA is used to demonstrate a novel lithium ion insertion model in which each ring carbon atom can reversibly accept a lithium ion, giving discharge capacities of up to nearly 2000 mA h g−1. This method provides a new strategy for the design of high-performance organic electrodes.

    15. Natural Product Synthesis

      Convergent Synthesis of Deoxypropionates (pages 5152–5156)

      Peter S. Diez and Prof. Glenn C. Micalizio

      Version of Record online: 5 APR 2012 | DOI: 10.1002/anie.201200035

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      Metallacycle-mediated allylic alcohol–alkyne reductive cross-coupling is described as a convergent solution to the synthesis of deoxypropionates. This approach offers superior step-economy in comparison to available strategies based on multistep iterative chain elongation. The technique is demonstrated in a concise synthesis of the C1–C11 subunit of borrelidin, and a total synthesis of (−)-vittatalactone.

    16. Carbene Polymerization

      Stereospecific Carbene Polymerization with Oxygenated Rh(diene) Species (pages 5157–5161)

      Annemarie J. C. Walters, Dipl.-Chem. Oliver Troeppner, Prof. Dr. Ivana Ivanović-Burmazović, Dr. Cristina Tejel, Dr.  M. Pilar del Río, Prof. Dr. Joost N. H. Reek and Dr. Bas de Bruin

      Version of Record online: 12 APR 2012 | DOI: 10.1002/anie.201200069

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      Breath-taking activation: Stereoregular carbene polymerization proceeds via cationic [(allyl)RhIII–polymeryl]+ species. These are most efficiently generated by oxygenation of the [(diene)RhI] precatalysts, which involves an unusual rearrangement of 2-rhodaoxetane intermediates. This discovery gives detailed insight in the reaction mechanism.

    17. Supramolecular Chemistry

      Biocompatible Polyurea Dendrimers with pH-Dependent Fluorescence (pages 5162–5165)

      Rita B. Restani, Patrícia I. Morgado, Maximiano P. Ribeiro, Prof. Ilídio J. Correia, Prof. Ana Aguiar-Ricardo and Dr. Vasco D. B. Bonifácio

      Version of Record online: 5 APR 2012 | DOI: 10.1002/anie.201200362

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      Blue: Biocompatible and biodegradable water-soluble dendrimers comprising ureas within the interior and amino groups on the periphery were synthesized in supercritical carbon dioxide (dendrimer of generation 1 shown in picture). This novel class of dendrimers shows a pH-dependent intrinsic blue fluorescence at very low concentrations, which makes them potential polymeric fluorescent cell markers.

    18. Switchable Catalysts

      A Rotaxane-Based Switchable Organocatalyst (pages 5166–5169)

      Dr. Victor Blanco, Dr. Armando Carlone, Dr. Kevin D. Hänni, Prof. David A. Leigh and Dr. Bartosz Lewandowski

      Version of Record online: 13 APR 2012 | DOI: 10.1002/anie.201201364

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      Switch it on! The activity of an organocatalytic group incorporated within a rotaxane architecture can be controlled by switching the position of the macrocycle. The system was used to mediate the progress of the Michael addition of an aliphatic thiol to trans-cinnamaldehyde.

    19. Synthetic Methods

      Palladium(II)-Catalyzed Intramolecular Diamination of Alkynes under Aerobic Oxidative Conditions: Catalytic Turnover of an Iodide Ion (pages 5170–5174)

      Dr. Bo Yao, Dr. Qian Wang and Prof. Dr. Jieping Zhu

      Version of Record online: 12 APR 2012 | DOI: 10.1002/anie.201201640

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      “I” did it: A sequential intramolecular amination/N-demethylation/amidation of internal acetylenes in the presence of a catalytic amount of Pd(OAc)2 and nBu4NI afforded indolo[3,2-c]isoquinolinones under mild aerobic conditions (see scheme, DMSO=dimethyl sulfoxide). The iodide ion was regenerated by reaction of in situ generated MeI with HOAc present in the reaction mixture.

    20. Asymmetric Catalysis

      Gold(I)-Catalyzed Stereoconvergent, Intermolecular Enantioselective Hydroamination of Allenes (pages 5175–5178)

      Kristina L. Butler, Michele Tragni and Prof. Ross A. Widenhoefer

      Version of Record online: 11 APR 2012 | DOI: 10.1002/anie.201201584

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      Gold and silver: A 1:2 mixture of [{(S)-1}(AuCl)2] and AgBF4 catalyzes the enantioselective hydroamination of chiral, racemic 1,3-disubstituted allenes with N-unsubstituted carbamates to form N-allylic carbamates in good yield, with high regio- and diastereoselectivity, and up to 92 % ee (see scheme, Cbz=benzyloxycarbonyl).

    21. NMR Spectroscopy in Solution

      Hyperpolarized Binding Pocket Nuclear Overhauser Effect for Determination of Competitive Ligand Binding (pages 5179–5182)

      Youngbok Lee, Haifeng Zeng, Dr. Adam Mazur, Melanie Wegstroth, Priv.-Doz. Dr. Teresa Carlomagno, Dr. Marcel Reese, Dr. Donghan Lee, Dr. Stefan Becker, Prof. Dr. Christian Griesinger and Prof. Dr. Christian Hilty

      Version of Record online: 12 APR 2012 | DOI: 10.1002/anie.201201003

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      Protein-mediated polarization transfer: Ligands L1 and L2 that competitively bind to a protein are subject to indirect spin-polarization transfer through the binding site of the protein. If protons HL1 of one ligand are hyperpolarized by dynamic nuclear polarization (DNP, see picture), signal intensities in the NMR spectrum of the second ligand become enhanced. The relative build-up of signal of the second ligand yields information on its binding epitope.

    22. Asymmetric Catalysis

      Asymmetric N-Allylation of Indoles Through the Iridium-Catalyzed Allylic Alkylation/Oxidation of Indolines (pages 5183–5187)

      Dr. Wen-Bo Liu, Xiao Zhang, Prof. Dr. Li-Xin Dai and Prof. Dr. Shu-Li You

      Version of Record online: 11 APR 2012 | DOI: 10.1002/anie.201200649

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      Two steps can be better than one: An efficient synthesis of enantioenriched N-allylindoles by a one-pot Ir-catalyzed asymmetric allylic alkylation/oxidation reaction of indolines has been realized. The current method features high regioselectivity and enantioselectivity together with a broad range of indoles with varying electronic properties. The utility of this method was demonstrated by the synthesis of dihydropyrrolo[1,2-a]indole derivatives.

    23. C[BOND]H Bond Functionalization

      Nonnatural Amino Acid Synthesis by Using Carbon–Hydrogen Bond Functionalization Methodology (pages 5188–5191)

      Ly Dieu Tran and Prof. Dr. Olafs Daugulis

      Version of Record online: 12 APR 2012 | DOI: 10.1002/anie.201200731

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      Taking direction well: Substituted phenylalanine derivatives were prepared by C[BOND]H bond functionalization (see scheme). The syntheses are highly convergent and employ an N-phthaloylalanine with a 2-thiomethylaniline directing group. The use of an 8-aminoquinoline directing group allows for the diarylation of methyl and the diastereoselective arylation of methylene groups.

    24. Metal–Organic Frameworks

      A Chiral, Self-Catenating and Porous Metal–Organic Framework and its Post-Synthetic Metal Uptake (pages 5192–5195)

      Dr. Tia Jacobs, Rob Clowes, Prof. Andrew I. Cooper and Dr. Michaele J. Hardie

      Version of Record online: 5 APR 2012 | DOI: 10.1002/anie.201200758

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      Free vacancies: A robust and porous metal–organic framework material with unique 4-connected self-catenating structure of {85⋅10} topology was synthesized. The structure features empty bipyridine metal-chelating sites that can be doped with copper cations in a single-crystal-to-single-crystal post-synthetic modification (see picture; scale bar 20 μm).

    25. Optical sensing

      Cubic Molecularly Imprinted Polymer Nanoparticles with a Fluorescent Core (pages 5196–5199)

      Petya K. Ivanova-Mitseva, Dr. Antonio Guerreiro, Dr. Elena V. Piletska, Dr. Michael. J. Whitcombe, Dr. Zhaoxia Zhou, Petar A. Mitsev, Dr. Frank Davis and Prof. Sergey A. Piletsky

      Version of Record online: 13 APR 2012 | DOI: 10.1002/anie.201107644

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      Building blocks for a bright future: A new method for the synthesis of organic nanoparticles (NPs) was developed combining a molecularly imprinted polymer shell and a fluorescent dendrimer biosensing core. Cubic organic nanoparticles are reported for the first time. The polymeric nanoparticles could be used as a direct replacement for antibodies in biosensor applications.

    26. Liquid Crystals

      Distorted Arene Core Allows Room-Temperature Columnar Liquid-Crystal Glass with Minimal Side Chains (pages 5200–5203)

      Dr. Julien Kelber, Dr. Marie-France Achard, Dr. Fabien Durola and Dr. Harald Bock

      Version of Record online: 12 APR 2012 | DOI: 10.1002/anie.201108886

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      Atropoisomeric aromatic cores enhance disorder inside the supramolecular packing of disk-shaped mesogens. Core-extension of perylene with an atropoisomeric [4]helicene fragment thus gives rise to a room-temperature liquid crystal even with extremely short side chains. Replacement of diester moieties by imide substituents allows switching from donor- to acceptor-type electronic characteristics.

    27. C[BOND]H Activation

      Palladium-Catalyzed Oxidative Double C[BOND]H Functionalization/Carbonylation for the Synthesis of Xanthones (pages 5204–5207)

      Hua Zhang, Renyi Shi, Pei Gan, Chao Liu, Anxing Ding, Qiuyi Wang and Prof. Aiwen Lei

      Version of Record online: 4 APR 2012 | DOI: 10.1002/anie.201201050

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      Two at once: Xanthones with different functional groups were obtained with CO (balloon) in the presence of a simple catalytic system that consists of Pd(OAc)2, K2S2O8, and trifluoroacetic acid (see scheme). Preliminary mechanism studies reveal that the second C[BOND]H functionalization might be the rate-determining step.

    28. Surface Chemistry

      Reactivity of Surfaces Determined by Local Electrochemical Triggering: A Bromo-Terminated Self-Assembled Monolayer (pages 5208–5212)

      Sandra Nunige, Dr. Renaud Cornut, Dr. Hassan Hazimeh, Dr. Fanny Hauquier, Prof. Dr. Christine Lefrou, Dr. Catherine Combellas and Dr. Frédéric Kanoufi

      Version of Record online: 12 APR 2012 | DOI: 10.1002/anie.201201083

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      Magic ink: The chemical reactivity of a bromo-terminated self-assembled monolayer immobilized on an insulating substrate is quantified from the time evolution of patterns formed during the local reduction of the SAM (see picture; bpy=2,2′-bipyridine). The potential of this lithographic strategy to determine the reactivity of the self-assembled monolayer is described and compared to surface interrogation by electrochemical microscopy.

    29. N2 Cleavage

      Structure and Reactivity of a Hafnocene μ-Nitrido Prepared From Dinitrogen Cleavage (pages 5213–5216)

      Scott P. Semproni, Carsten Milsmann and Paul J. Chirik

      Version of Record online: 5 APR 2012 | DOI: 10.1002/anie.201201361

      Thumbnail image of graphical abstract

      Carbonylation of the strongly activated hafnocene dinitrogen complex, [{(η5-C5H2-1,2,4-Me3)2Hf}2222-N2)], in the presence of electron-rich 4-substituted pyridines resulted in isolation of rare μ-nitrido hafnocene complexes prepared from N2 cleavage. The electronic and molecular structures as well as the intermediacy in N[BOND]C bond forming reactions has been determined.

    30. Synthetic Methods

      Catalytic Asymmetric Total Synthesis of Chimonanthine, Folicanthine, and Calycanthine through Double Michael Reaction of Bisoxindole (pages 5217–5221)

      Harunobu Mitsunuma, Prof. Dr. Masakatsu Shibasaki, Prof. Dr. Motomu Kanai and Dr. Shigeki Matsunaga

      Version of Record online: 12 APR 2012 | DOI: 10.1002/anie.201201132

      Thumbnail image of graphical abstract

      Direct access: Sterically hindered vicinal quaternary carbon stereocenters were constructed by catalytic enantio- and diastereoselective double Michael reaction, providing straightforward access to dimeric hexahydropyrroloindole alkaloids. A Mn(4-fluorobenzoate)2/Schiff base complex and a Mg(OAc)2/benzoic acid system were used as catalysts.

    31. Metal-Catalyzed One-Pot Synthesis of Tetrazines Directly from Aliphatic Nitriles and Hydrazine (pages 5222–5225)

      Dr. Jun Yang, Dr. Mark R. Karver, Weilong Li, Swagat Sahu and Prof. Neal K. Devaraj

      Version of Record online: 18 APR 2012 | DOI: 10.1002/anie.201201117

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      Paving the way: The lack of convenient synthetic methods is a significant roadblock to the broader use of 1,2,4,5-tetrazines in bioorthogonal chemistry and functional materials. Lewis acid metal catalysts—most notably divalent nickel and zinc salts—are described to catalyze the one-pot synthesis of 1,2,4,5-tetrazines directly from aliphatic nitriles (see scheme).

    32. Inhibitors

      2-Aminobenzimidazole Derivatives Strongly Inhibit and Disperse Pseudomonas aeruginosa Biofilms (pages 5226–5229)

      Dr. Reto Frei, Anthony S. Breitbach and Prof. Dr. Helen E. Blackwell

      Version of Record online: 5 APR 2012 | DOI: 10.1002/anie.201109258

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      Bacterial biofilms are exceptionally difficult to clear using traditional antibiotics and constitute a significant health threat. 2-Aminobenzimidazole derivatives (see scheme) are capable of strongly inhibiting the growth of and dispersing Pseudomonas aeruginosa biofilms. These molecules were found to modulate quorum sensing in reporter strains, and represent some of strongest P. aeruginosa biofilm inhibitors known.

    33. Chemical Biology

      Identification of a Selective, Activity-Based Probe for Glyceraldehyde 3-Phosphate Dehydrogenases (pages 5230–5233)

      Dr. Farnusch Kaschani, Dr. Jérôme Clerc, Daniel Krahn, David Bier, Tram Ngoc Hong, Dr. Christian Ottmann, Sherry Niessen, Dr. Tom Colby, Dr. Renier A. L. van der Hoorn and Prof. Dr. Markus Kaiser

      Version of Record online: 5 APR 2012 | DOI: 10.1002/anie.201107276

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      Exceptionally specific: The natural-product-like structural complexity of a bicyclic hydantoin was exploited to generate the novel, highly specific activity-based profiling probe (ABPP) Mrl-Rh (Rh=rhodamine; see picture) for glyceraldehyde 3-phosphate dehydrogenases. This probe can be used to investigate activity changes of this enzyme class during plant–pathogen interactions.

    34. Organocatalysis

      Nucleophilic Addition of Enols and Enamines to α,β-Unsaturated Acyl Azoliums: Mechanistic Studies (pages 5234–5238)

      Ramesh C. Samanta, Biplab Maji, Dr. Suman De Sarkar, Dr. Klaus Bergander, Dr. Roland Fröhlich, Dr. Christian Mück-Lichtenfeld, Prof. Dr. Herbert Mayr and Prof. Dr. Armido Studer

      Version of Record online: 13 APR 2012 | DOI: 10.1002/anie.201109042

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      1,4 but not 1,2! The reactivity of 1 towards different nucleophiles (deprotonated β-diketones, enamines, and malonodinitrile) was investigated by NMR and kinetic experiments. These investigations proved that C[BOND]C bond formation occurs by a Michael-type 1,4-addition and not by a 1,2-addition and subsequent [3,3]-sigmatropic rearrangement. The first X-ray structure of an α,β-unsaturated acyl azolium salt (1) is also presented.

    35. Natural Products

      Pellasoren: Structure Elucidation, Biosynthesis, and Total Synthesis of a Cytotoxic Secondary Metabolite from Sorangium cellulosum (pages 5239–5243)

      Christine Jahns, Thomas Hoffmann, Stefan Müller, Dr. Klaus Gerth, Dr. Peter Washausen, Prof. Dr. Gerhard Höfle, Prof. Dr. Hans Reichenbach, Prof. Dr. Markus Kalesse and Prof. Dr. Rolf Müller

      Version of Record online: 5 APR 2012 | DOI: 10.1002/anie.201200327

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      Genetic analysis of biosynthetic gene clusters is becoming an accepted tool to predict the stereochemical outcome of a biosynthesis. However, in the case of pellasoren, one chiral center was not predicted correctly. The absolute configuration was verified by total synthesis, which also demonstrated that stereoselective protonations can be successfully applied to natural products synthesis.

    36. Bioorganometallic Chemistry

      The Art of Filling Protein Pockets Efficiently with Octahedral Metal Complexes (pages 5244–5246)

      Sebastian Blanck, Dr. Jasna Maksimoska, Julia Baumeister, Dr. Klaus Harms, Prof. Ronen Marmorstein and Prof. Dr. Eric Meggers

      Version of Record online: 1 MAR 2012 | DOI: 10.1002/anie.201108865

      Thumbnail image of graphical abstract

      Better fit, less effort: An easy-to-synthesize ruthenium phthalimide complex (tan-colored carbon atoms in the picture) was designed to bind within the active site of the p21-activated kinase 1 in a novel fashion that differs from that of the previously established staurosporine-inspired metallopyridocarbazoles (gray-colored carbon atoms).

    37. Amyloid Fibrils

      Detailed Analysis of the Energy Barriers for Amyloid Fibril Growth (pages 5247–5251)

      Alexander K. Buell, Anne Dhulesia, Duncan A. White, Tuomas P. J. Knowles, Christopher M. Dobson and Mark E. Welland

      Version of Record online: 5 APR 2012 | DOI: 10.1002/anie.201108040

      Thumbnail image of graphical abstract

      The free energy barriers that determine the kinetics of the growth of amyloid fibrils have been measured for a series of peptides and proteins using a quartz crystal microbalance. The results indicate that the enthalpic contribution to the free energy barrier is invariably unfavorable and correlates with the size and structure of the soluble parent polypeptide, whereas the entropic contribution is favorable and linked to the hydrophobicity of the peptide sequence.

    38. Porous Organic Crystals

      Rational Construction of an Extrinsic Porous Molecular Crystal with an Extraordinary High Specific Surface Area (pages 5252–5255)

      Dr. Michael Mastalerz and Prof. Dr. Iris M. Oppel

      Version of Record online: 30 MAR 2012 | DOI: 10.1002/anie.201201174

      Thumbnail image of graphical abstract

      Small molecule, large surface area: A rigid triptycene derivative self-assembles by hydrogen bonds to a porous crystal with one-dimensional channels of about 14 Å diameter. Solvents in the channels can be removed to generate an extrinsic porous material with a specific BET surface area of 2796 m2 g−1. Furthermore, gases can be selectively adsorbed within the pores at 1 bar.

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