Angewandte Chemie International Edition

Cover image for Vol. 48 Issue 36

August 24, 2009

Volume 48, Issue 36

Pages 6563–6739

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Essay
    12. Review
    13. Communications
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    1. Cover Picture: Reversible Metal-Free Carbon Dioxide Binding by Frustrated Lewis Pairs (Angew. Chem. Int. Ed. 36/2009) (page 6563)

      Cornelia M. Mömming, Edwin Otten, Gerald Kehr, Roland Fröhlich, Stefan Grimme, Douglas W. Stephan and Gerhard Erker

      Article first published online: 19 AUG 2009 | DOI: 10.1002/anie.200990186

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      Reversible binding of CO2 can be realized with borane–phosphane frustrated Lewis pairs (FLPs). In their Communication on page 6643 ff., G. Erker et al. describe how the greenhouse gas CO2 is captured to form both cyclic and acyclic adducts through P[BOND]C and O[BOND]B bond formation. The reaction is reversed and CO2 released when the temperature of the solution is raised. Theoretical analysis describes CO2 binding by FLPs as a synchronous concerted reaction.

  2. Inside Cover

    1. Top of page
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    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
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    9. Book Review
    10. Highlights
    11. Essay
    12. Review
    13. Communications
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    1. Inside Cover: Light-Driven Enantioselective Organocatalysis (Angew. Chem. Int. Ed. 36/2009) (page 6564)

      Christiane Müller, Andreas Bauer and Thorsten Bach

      Article first published online: 19 AUG 2009 | DOI: 10.1002/anie.200990187

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      A chiral organocatalyst that is excited by UV light and is capable of transferring the excitation energy to a bound substrate is presented by T. Bach et al. in their Communication on page 6640 ff. The energy that is provided by sensitization allows a photocycloaddition in a chiral environment and thus the synthesis of the product is achieved with high enantiomeric excess.

  3. Editorial

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    11. Essay
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      Angewandte Chemie and Catalysis (pages 6566–6567)

      Peter Gölitz

      Article first published online: 19 AUG 2009 | DOI: 10.1002/anie.200904352

  4. Graphical Abstract

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    4. Editorial
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    10. Highlights
    11. Essay
    12. Review
    13. Communications
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  5. News

    1. Top of page
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    4. Editorial
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    10. Highlights
    11. Essay
    12. Review
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  6. Author Profile

    1. Top of page
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    3. Inside Cover
    4. Editorial
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    1. Yitzhak Apeloig (pages 6584–6586)

      Article first published online: 18 AUG 2009 | DOI: 10.1002/anie.200903376

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      “My favorite subject at school was soccer. When I was eighteen I wanted to be a scientist‥ …” This and more about Yitzhak Apeloig can be found on page 6584.

  7. News

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  8. Book Review

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    1. Classics in Stereoselective Synthesis. By Erick M. Carreira and Lisbet Kvaerno. (page 6589)

      Dirk Trauner

      Article first published online: 19 AUG 2009 | DOI: 10.1002/anie.200902514

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      Wiley-VCH, Weinheim 2008. 632 pp., softcover € 69.00.—ISBN 978-3527299669

  9. Highlights

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    1. Signal Transduction

      The Transmembrane Structure of Integrin αIIbβ3: Significance for Signal Transduction (pages 6590–6593)

      Martin Hoefling, Horst Kessler and Kay-Eberhard Gottschalk

      Article first published online: 13 JUL 2009 | DOI: 10.1002/anie.200902016

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      Outside contact: Cells in multicellular organisms regulate their adhesion through specialized integrin receptors, which relay signals bidirectionally between the inside and outside of cells. The transmembrane domains (see picture, blue; the integrin–talin complex is red and green) of integrins are the center of the signaling process. Recently, structures of these domains have been reported that shed light on the signal transduction mechanism.

    2. Carbon Nanoribbons

      Unzipping Carbon Nanotubes: A Peeling Method for the Formation of Graphene Nanoribbons (pages 6594–6596)

      Andreas Hirsch

      Article first published online: 6 JUL 2009 | DOI: 10.1002/anie.200902534

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      Zipper examined: Elegant unzipping procedures result in the clean opening of multiwalled carbon nanotubes, leading to graphene nanoribbons (see scheme). Since graphene exhibits outstanding electronic properties, this method may be important in the development of modern nanoelectronic applications.

    3. Coordination Modes

      Organometallic Compounds of the Heavier s-Block Elements—What Next? (pages 6597–6599)

      J. David Smith

      Article first published online: 27 JUL 2009 | DOI: 10.1002/anie.200901506

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      Getting heavy: A novel dicesium methandiide and an organometallic compound of CaI without a Ca[BOND]Ca bond (see picture) are examples of species in which metals coordinate to anions. Thus, the normal statement that “ligands coordinate to metals” must be reversed.

  10. Essay

    1. Top of page
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    4. Editorial
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    1. Wilhelm Ostwald

      Wilhelm Ostwald: Founder of Physical Chemistry and Nobel Laureate 1909 (pages 6600–6606)

      Gerhard Ertl

      Article first published online: 17 JUN 2009 | DOI: 10.1002/anie.200901193

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      A great researcher, Wilhelm Ostwald, is honored here on the occasion of the hundredth anniversary of his receiving the Nobel Prize. At the time of the award in December 1909 he said that he was surprised that this highest scientific distinction was awarded for his work on catalysis; he expected that such recognition would come much later.

  11. Review

    1. Top of page
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    11. Essay
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    1. Hydrogen Storage

      Chemical and Physical Solutions for Hydrogen Storage (pages 6608–6630)

      Ulrich Eberle, Michael Felderhoff and Ferdi Schüth

      Article first published online: 13 JUL 2009 | DOI: 10.1002/anie.200806293

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      The stuff dreams are made of: Hydrogen is a promising energy carrier in future energy systems, but the storage for mobile and stationary applications is a substantial challenge. If on-board hydrogen storage of car running on a fuel cell can be solved, then also the other problems of a hydrogen infrastructure appear to be manageable. The picture compares the weight and volume of various fuels and tank systems for vehicles having a 500 km range.

  12. Communications

    1. Top of page
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    4. Editorial
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    1. Conjugated Macrocycles

      Giant Cyclo[n]thiophenes with Extended π Conjugation (pages 6632–6635)

      Fan Zhang, Günther Götz, Henrik D. F. Winkler, Christoph A. Schalley and Peter Bäuerle

      Article first published online: 27 JUN 2009 | DOI: 10.1002/anie.200900101

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      Dual roles and nanorings: A new family of cyclic oligothiophenes with up to 35 thiophene units is synthesized by using platinum complexes in a dual role as template and as reactive center. The ease of ionization and aggregation of the new compounds indicates that they have promising properties for use as organic electronic materials of increased structural complexity.

    2. Biphotonics

      Light-Directed Protein Binding of a Biologically Relevant β-Sheet (pages 6636–6639)

      Christian Hoppmann, Sabine Seedorff, Anja Richter, Heinz Fabian, Peter Schmieder, Karola Rück-Braun and Michael Beyermann

      Article first published online: 7 AUG 2009 | DOI: 10.1002/anie.200901933

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      Lit-up β attracts α: An azobenzene-ω-amino acid is incorporated as a photoswitch into a β-hairpin motif that mimics the binding site in neuronal NO synthase for α-syntrophin. Light-induced isomerization reversibly converts the stable monomer model peptide from its nonbinding, nonstructured trans form into the β-sheet-forming cis form which shows a remarkable affinity for α-syntrophin.

    3. Photochemistry

      Light-Driven Enantioselective Organocatalysis (pages 6640–6642)

      Christiane Müller, Andreas Bauer and Thorsten Bach

      Article first published online: 26 MAY 2009 | DOI: 10.1002/anie.200901603

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      Collection, sensitization, and selection are the tasks of the organocatalyst 1, which it fulfills almost perfectly in the photochemical conversion of quinolone 2. It collects light (λ>350 nm), transfers its energy to the substrate, and induces a high enantioselectivity. Even with only 10 mol % of catalyst, a yield of 90 % was achieved with an ee value of 92 %.

    4. CO2 Binding

      Reversible Metal-Free Carbon Dioxide Binding by Frustrated Lewis Pairs (pages 6643–6646)

      Cornelia M. Mömming, Edwin Otten, Gerald Kehr, Roland Fröhlich, Stefan Grimme, Douglas W. Stephan and Gerhard Erker

      Article first published online: 30 JUN 2009 | DOI: 10.1002/anie.200901636

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      Hot and bothered? Frustrated Lewis pairs comprising phosphine and borane react to reversibly bind and release CO2, offering a rare example of metal-free CO2 sequestration. The mechanism of formation of these CO2 derivatives 1 and 2 (see scheme) by almost simultaneous P[BOND]C and O[BOND]B bond formation was characterized by quantum chemical calculations.

    5. Gas Separation

      PST-1: A Synthetic Small-Pore Zeolite that Selectively Adsorbs H2 (pages 6647–6649)

      Jiho Shin, Miguel A. Camblor, Hee Chul Woo, Stuart R. Miller, Paul A. Wright and Suk Bong Hong

      Article first published online: 31 JUL 2009 | DOI: 10.1002/anie.200903336

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      No gas too small: A synthetic potassium gallosilicate natrolite with Si/Ga=1.28 (denoted PST-1; see picture, Ga/Si gray, O red, K pink) was found to selectively adsorb small gases, especially H2, and hence to discriminate them from slightly larger molecules such as Ar or CO2. The remarkable ease of its dehydration and great (hydro)thermal stability make PST-1 a potential candidate for fast, selective H2 or He separation processes.

    6. Asymmetric Synthesis

      Organocatalytic Asymmetric Desymmetrization–Fragmentation of Cyclic Ketones (pages 6650–6653)

      Gustav Dickmeiss, Vincenzo De Sio, Jonas Udmark, Thomas B. Poulsen, Vanesa Marcos and Karl Anker Jørgensen

      Article first published online: 5 AUG 2009 | DOI: 10.1002/anie.200903253

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      A ticket to total synthesis: The title reaction of meso cyclopropane cyclopentanones and epoxycyclopentanones was catalyzed by thiourea-containing cinchona alkaloids with good to excellent enantioselectivity (see scheme). The concept was extended to a one-pot asymmetric desymmetrization–fragmentation–Michael addition by including a nucleophile. A kinetic resolution based on this method was also demonstrated.

    7. Macrocycles

      A Modular Approach to Functionalized and Expanded Crown Ether Based Macrocycles Using Click Chemistry (pages 6654–6658)

      Sandra Binauld, Craig J. Hawker, Etienne Fleury and Eric Drockenmuller

      Article first published online: 4 AUG 2009 | DOI: 10.1002/anie.200903156

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      Tailored handcuffs: α-Azide-ω-alkyne oligomers are obtained in high yields from copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC), iterative chain growth, and protection–deprotection strategies. Intramolecular CuAAC under pseudo-high-dilution conditions then yields macrocycles with n=1–8 triazole units in the cyclic backbone (picture shows n=2; C gray, O red, N blue, H white).

    8. Hydrogen Storage

      A Series of Mixed-Metal Borohydrides (pages 6659–6663)

      Dorthe Ravnsbæk, Yaroslav Filinchuk, Yngve Cerenius, Hans J. Jakobsen, Flemming Besenbacher, Jørgen Skibsted and Torben R. Jensen

      Article first published online: 5 AUG 2009 | DOI: 10.1002/anie.200903030

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      Mix and match: A novel series of alkali-metal zinc borohydrides, LiZn2(BH4)5 (see picture), NaZn2(BH4)5, and NaZn(BH4)3, with fascinating structures are presented. An interpenetrated network structure, containing a [Zn2(BH4)5] ion, is observed for the first time for a borohydride. A three-dimensional framework containing a polymeric [{Zn(BH4)3}n]n ion is also identified.

    9. Dendrimers

      Bifunctional Green Iridium Dendrimers with a “Self-Host” Feature for Highly Efficient Nondoped Electrophosphorescent Devices (pages 6664–6666)

      Junqiao Ding, Bin Wang, Zhengyu Yue, Bing Yao, Zhiyuan Xie, Yanxiang Cheng, Lixiang Wang, Xiabin Jing and Fosong Wang

      Article first published online: 7 AUG 2009 | DOI: 10.1002/anie.200902954

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      Better without doping: Use of a dendron with a high carbazole density around an iridium core has been found to improve the performance of nondoped electrophosphorescent devices more effectively than the use of higher-generation dendrimers. A promising efficiency as high as 45.7 cd A−1 (13.4 %) together with a high luminance is obtained for 6 B-G1 (see picture). These values are very close to those of the corresponding doped device.

    10. Olefin Detection

      Unexpected Effects of Terminal Olefins on a Cooperative Recognition System that Implicate Olefin–Olefin Interactions (pages 6667–6670)

      Rie Wakabayashi, Tomohiro Ikeda, Yohei Kubo, Seiji Shinkai and Masayuki Takeuchi

      Article first published online: 31 JUL 2009 | DOI: 10.1002/anie.200901970

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      Super sensitive: A new method based on the guest-binding behavior of allosteric host molecules has been used to sensitively detect a weak olefin–olefin interaction with high precision (see picture).

    11. DNA Conformational Switches

      Reversible Photoswitching of a G-Quadruplex (pages 6671–6674)

      Shinzi Ogasawara and Mizuo Maeda

      Article first published online: 27 JUL 2009 | DOI: 10.1002/anie.200902183

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      Getting a grip: G-quadruplex formation can be regulated by reversible cistrans photoisomerization of the photochromic nucleobase 8-fluorenylvinyl-2′-deoxyguanosine (see picture: fluorene red, guanine green). Switching between a very stable quadruplex state and a non-structured state allows controlled binding to thrombin (pink).

    12. Photochirogenesis

      Catalytic Enantiodifferentiating Photocyclodimerization of 2-Anthracenecarboxylic Acid Mediated by a Non-Sensitizing Chiral Metallosupramolecular Host (pages 6675–6677)

      Chenfeng Ke, Cheng Yang, Tadashi Mori, Takehiko Wada, Yu Liu and Yoshihisa Inoue

      Article first published online: 31 JUL 2009 | DOI: 10.1002/anie.200902911

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      Cap in hand: Combined use of diamino-γ-cyclodextrin (CD) and Cu(ClO4)2 resulted in the first catalytic supramolecular photochirogenesis in the photocyclodimerization of 2-anthracenecarboxylic acid. The anti-head-to-head cyclodimer formed in 64–70 % enantiomeric excess and about 50 % yield; these values are the highest ever reported for CD-mediated photochirogenesis.

    13. Redox Sites in Zeolites

      Unambiguous Observation of Electron Transfer from a Zeolite Framework to Organic Molecules (pages 6678–6682)

      Lu Li, Xue-Song Zhou, Guo-Dong Li, Xiao-Liang Pan and Jie-Sheng Chen

      Article first published online: 7 AUG 2009 | DOI: 10.1002/anie.200902199

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      Making a hole: Oxygen atoms bridging two silicon atoms in a protonated zeolite can be oxidized through reaction with an alkyl bromide to generate paramagnetic centers in the zeolite framework (see structures and EPR spectrum; red O, blue Si, purple Al, green C, yellow Br, white H). Electron transfer from the zeolite framework could partially explain the range of products formed in acid-catalyzed reactions with zeolite catalysts.

    14. Synthetic Replicators

      Self-Replicating Amphiphilic β-Sheet Peptides (pages 6683–6686)

      Boris Rubinov, Nathaniel Wagner, Hanna Rapaport and Gonen Ashkenasy

      Article first published online: 30 JUL 2009 | DOI: 10.1002/anie.200902790

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      Simple peptides can do that too: Synthetic amphiphilic peptides 1, formed of electrophilic (E) and nucleophilic (N) precursors, are close analogues of the Glu-(Phe-Glu)n molecules. The peptides form soluble one-dimensional β-sheet aggregates in water (see picture), and serve to significantly accelerate chemical ligation and self-replication.

    15. Möbius Aromaticity

      Thermal Fusion Reactions of meso-(3-Thienyl) Groups in [26]Hexaphyrins to Produce Möbius Aromatic Molecules (pages 6687–6690)

      Mitsunori Inoue, Kil Suk Kim, Masaaki Suzuki, Jong Min Lim, Jae-Yoon Shin, Dongho Kim and Atsuhiro Osuka

      Article first published online: 7 AUG 2009 | DOI: 10.1002/anie.200902677

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      Fuse to twist: Simple thermal reactions of meso-(3-thienyl) groups in Hückel-aromatic [26]hexaphyrins (see picture, left; N blue, S yellow, F green) provide 3-thienyl-fused [28]hexaphyrins (right) that have Möbius aromatic character, as indicated by a number of spectroscopic methods.

    16. Binding Affinity

      Ranking of High-Affinity Ligands by NMR Spectroscopy (pages 6691–6694)

      Xiaolu Zhang, Andrea Sänger, René Hemmig and Wolfgang Jahnke

      Article first published online: 31 JUL 2009 | DOI: 10.1002/anie.200902591

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      Let the protein choose its ligand, and use NMR spectroscopy to see which one it has chosen (see scheme). This principle enables the most precise determination of relative binding affinities of two ligands to a protein receptor and for the first time allows the affinities of tightly binding ligands to be determined by NMR spectroscopy. This approach is a valuable tool for the lead-optimization process.

    17. Lewis Acid Adducts

      [(IMes)2Pt(H)(ClBC5H4SiMe3)]: a Borabenzene–Platinum Adduct with an Unusual Pt-Cl-B Interaction (pages 6695–6698)

      André Languérand, Stephanie S. Barnes, Guillaume Bélanger-Chabot, Laurent Maron, Philippe Berrouard, Pierre Audet and Frédéric-Georges Fontaine

      Article first published online: 5 AUG 2009 | DOI: 10.1002/anie.200902870

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      A Pt-Cl-B interaction is observed when a borabenzene derivative reacts with a platinum(0) precursor with bulky N-heterocyclic carbene ligands. The resulting platinum(II) complex (see picture; Pt red, N blue, Cl green, B pink, Si yellow) involves a new bonding mode for borabenzene, which usually binds in an η6 fashion to transition metals.

    18. Electrets

      Patterning of Electrostatic Charge on Electrets Using Hot Microcontact Printing (pages 6699–6703)

      Dan Zhao, Liting Duan, Mianqi Xue, Wei Ni and Tingbing Cao

      Article first published online: 28 JUL 2009 | DOI: 10.1002/anie.200902627

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      Stamp on a hot tin roof: A topographically patterned poly(dimethylsiloxane) (PDMS) stamp is heated to 50–220 °C. This stamp uses the heat energy as “ink” for microcontact printing (μCP) by inducing chemical cross-linking, decomposition, or other transformations. The hot μCP technique can pattern electrostatic charges on electrets by selective thermally stimulated discharge (TSD, see picture) or depolarization.

    19. Monolithic Materials

      Ring-Opening Polymerization with Synergistic Co-monomers: Access to a Boronate-Functionalized Polymeric Monolith for the Specific Capture of cis-Diol-Containing Biomolecules under Neutral Conditions (pages 6704–6707)

      Lianbing Ren, Zhen Liu, Yunchun Liu, Peng Dou and Hong-Yuan Chen

      Article first published online: 30 JUL 2009 | DOI: 10.1002/anie.200902469

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      Molecular teamwork: Synergistic co-monomers contained in a boronate-functionalized polymeric monolith function as a single Wulff-type boronic acid ligand to enable the specific capture of cis-diol-containing biomolecules under neutral conditions (see scheme). When the medium is made more acidic, the amine group is protonated, and B–N coordination is broken, which results in the release of the cis diol from the monolith.

    20. NMR Spectroscopy

      On the Treatment of Conformational Flexibility when Using Residual Dipolar Couplings for Structure Determination (pages 6708–6712)

      Christina M. Thiele, Volker Schmidts, Benjamin Böttcher, Iria Louzao, Robert Berger, Arnold Maliniak and Baltzar Stevensson

      Article first published online: 4 AUG 2009 | DOI: 10.1002/anie.200902398

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      Mission possible! The motional averaging of NMR spectroscopic data complicates the determination of conformation and relative configuration in flexible organic molecules. Two alternative routes are discussed for the treatment of conformational equilibrium in a moderately flexible compound (see the superposition of the two conformers of the butyrolactone studied) when residual dipolar couplings are used.

    21. Domino Reactions

      Palladium-Catalyzed Domino Direct Arylation/N-Arylation: Convenient Synthesis of Phenanthridines (pages 6713–6716)

      David A. Candito and Mark Lautens

      Article first published online: 31 JUL 2009 | DOI: 10.1002/anie.200902400

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      Domino reactions possess the ability to generate complexity from simple starting materials. Disclosed is a strategy for the domino direct arylation/N-arylation for the facile construction of diverse phenanthridine derivatives (see scheme; TMS=trimethylsilyl, TBDMS=tert-butyldimethylsilyl).

    22. Multicomponent Reactions

      Brønsted Acid Catalyzed Enantioselective Three-Component Reaction Involving the α Addition of Isocyanides to Imines (pages 6717–6721)

      Tao Yue, Mei-Xiang Wang, De-Xian Wang, Géraldine Masson and Jieping Zhu

      Article first published online: 5 AUG 2009 | DOI: 10.1002/anie.200902385

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      All three together now: Three-component reactions of aldehydes, anilines, and α-isocyanoacetamides in the presence of a catalytic amount of chiral phosphoric acid afforded the 5-(1-aminoalkyl)-5-aminooxazole 1 in excellent yields and moderate to good enantiomeric excess (see scheme).

    23. Enzyme Mimics

      Downsizing of Enzymes by Chemical Methods: Arginine Mimics with Low pKa Values Increase the Rates of Hydrolysis of RNA Model Compounds (pages 6722–6725)

      N. Johan V. Lindgren, Lars Geiger, Jesus Razkin, Carsten Schmuck and Lars Baltzer

      Article first published online: 4 AUG 2009 | DOI: 10.1002/anie.200900595

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      A talented mimic: Large rate enhancements were observed in the catalysis of reactions of RNA models when two arginine residues and two histidine residues were replaced with residues with a guanidiniocarbonyl pyrrole (Gcp) side chain (see structure) in a folded polypeptide catalyst. Gcp fulfilled the functions of, and even outperformed, both Arg and His.

    24. Synthetic Methods

      Rhodium-Mediated Decarboxylative Conjugate Addition of Fluorinated Benzoic Acids: Stoichiometric and Catalytic Transformations (pages 6726–6730)

      Zhong-Ming Sun and Pinjing Zhao

      Article first published online: 5 AUG 2009 | DOI: 10.1002/anie.200901097

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      Depending on the bisphosphine ligand, the decarboxylation of 2,6-difluorinated benzoic acids with a RhI catalyst in the presence of an acrylic ester or acrylamide led preferentially to conjugate addition (product 1) or Heck–Mizoroki arylation (product 2; binap=2,2′-bis(diphenylphosphanyl)-1,1′-binaphthyl, diop=4,5-bis(diphenylphosphanylmethyl)-2,2-dimethyl-1,3-dioxolane).

    25. Cross-Coupling

      Manganese-Catalyzed Oxidative Cross-Coupling of Grignard Reagents with Oxygen as an Oxidant (pages 6731–6734)

      Gérard Cahiez, Christophe Duplais and Julien Buendia

      Article first published online: 7 AUG 2009 | DOI: 10.1002/anie.200902188

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      Oxidative heterocoupling between two Grignard reagents RMgX and R′MgX is made possible by manganese catalysis with O2 as an oxidant. This procedure, development of which was based on mechanistic analysis of the corresponding homocoupling reaction, can be steered towards the heterocoupling product at the expense of the homocoupling products by judicious choice of the R and R′ groups (see examples).

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      Preview: Angew. Chem. Int. Ed. 37/2009 (page 6739)

      Article first published online: 19 AUG 2009 | DOI: 10.1002/anie.200990190

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