Angewandte Chemie International Edition

Cover image for Vol. 49 Issue 10

March 1, 2010

Volume 49, Issue 10

Pages 1697–1893

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Reviews
    8. Highlights
    9. Essay
    10. Review
    11. Communications
    12. Preview
    1. Cover Picture: A Recyclable Nanoparticle-Supported Palladium Catalyst for the Hydroxycarbonylation of Aryl Halides in Water (Angew. Chem. Int. Ed. 10/2010) (page 1697)

      Sebastian Wittmann, Alexander Schätz, Robert N. Grass, Wendelin J. Stark and Oliver Reiser

      Version of Record online: 22 FEB 2010 | DOI: 10.1002/anie.201000369

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      Temperature-dependent reversible immobilization of Pd catalysts on carbon-coated, magnetic Co nanoparticles is facilitated by pyrene-modified N-heterocyclic carbene ligands. O. Reiser et al. show in their Communication on page 1867 ff. how this approach allows the efficient palladium-catalyzed carboxlyation of aryl halides in water at 100 °C: In each of 16 cycles the catalyst is recovered onto the nanoparticles by cooling to room temperature. The nanoparticles are then separated from the mixture by magnetic decantation.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Reviews
    8. Highlights
    9. Essay
    10. Review
    11. Communications
    12. Preview
    1. Inside Cover: Polyoxometalates Made of Gold: The Polyoxoaurate [AuIII4AsV4O20]8− (Angew. Chem. Int. Ed. 10/2010) (page 1698)

      Natalya V. Izarova, Nina Vankova, Thomas Heine, Rosa Ngo Biboum, Bineta Keita, Louis Nadjo and Ulrich Kortz

      Version of Record online: 19 FEB 2010 | DOI: 10.1002/anie.201000767

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      A brand new line of gold jewelry has been designed in the world of polyoxometalate chemistry. In their Communication on page 1886 ff, U. Kortz et al. identify the first discrete inorganic polyoxoaurate [AuIII4AsV4O20]8− with a tetrameric structure and square-planar coordinated AuIII ions linked by oxo and arsenate bridging ligands (see structure; Au yellow, As blue, O red). The facile open-beaker synthetic procedure appears to be a convenient and general method for making a variety of gold-based inorganic oxo complexes. Mr. Rami Al-Oweini (PhD Student, Jacobs University) is thanked for his creative design.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Reviews
    8. Highlights
    9. Essay
    10. Review
    11. Communications
    12. Preview
  4. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Reviews
    8. Highlights
    9. Essay
    10. Review
    11. Communications
    12. Preview
  5. Author Profile

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Reviews
    8. Highlights
    9. Essay
    10. Review
    11. Communications
    12. Preview
    1. Pierre Braunstein (pages 1718–1720)

      Version of Record online: 9 FEB 2010 | DOI: 10.1002/anie.201000183

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      “My favorite subjects at school ranged from Latin to sciences, with an increasing emphasis on the latter. I chose chemistry as a career because I enjoyed the subject, its relevance to everyday life, and its versatility …” This and more about Pierre Braunstein can be found on page 1718.

  6. Book Reviews

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Reviews
    8. Highlights
    9. Essay
    10. Review
    11. Communications
    12. Preview
    1. Cellular and Biomolecular Recognition. Synthetic and Non-Biological Molecules. Edited by Raz Jelinek. (page 1721)

      Friedrich Simmel

      Version of Record online: 22 FEB 2010 | DOI: 10.1002/anie.200907317

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      Wiley-VCH, Weinheim 2009. 349 pp., hardcover € 139.00.—ISBN 978-3527322657

    2. Carbon Nanotube Science. Synthesis, Properties and Applications. By Peter J. F. Harris. (pages 1722–1723)

      Andreas Hirsch and Claudia Backes

      Version of Record online: 22 FEB 2010 | DOI: 10.1002/anie.201000314

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      Cambridge University Press 2009. 314 pp., hardcover £ 45.00.—ISBN 978-0521828956

  7. Highlights

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Reviews
    8. Highlights
    9. Essay
    10. Review
    11. Communications
    12. Preview
    1. Decarbonylative Coupling

      Ruthenium-Catalyzed Alkene Synthesis by the Decarbonylative Coupling of Aldehydes with Alkynes (pages 1724–1725)

      C. Liana Allen and Jonathan M. J. Williams

      Version of Record online: 5 FEB 2010 | DOI: 10.1002/anie.200906896

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      CO goes: A recent report has demonstrated that aldehydes can undergo decarbonylation and addition across alkynes to give alkenes (see scheme). The scope of the process is discussed along with an overview of other metal-catalyzed decarbonylative reactions.

    2. ipso-Nitration

      ipso-Nitration of Arenes (pages 1726–1728)

      G. K. Surya Prakash and Thomas Mathew

      Version of Record online: 9 FEB 2010 | DOI: 10.1002/anie.200906940

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      Meeting the challenge: Buchwald et al. have developed a very efficient and mild method for the ipso-nitration of a variety of aromatic/heteroaromatic chlorides, triflates, and nonaflates. The palladation–nitration protocol is compatible with many functional groups.

  8. Essay

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Reviews
    8. Highlights
    9. Essay
    10. Review
    11. Communications
    12. Preview
    1. Organocatalysis

      Emil Knoevenagel and the Roots of Aminocatalysis (pages 1730–1734)

      Benjamin List

      Version of Record online: 19 FEB 2010 | DOI: 10.1002/anie.200906900

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      The progress of aminocatalysis has been breathtaking—but what are its roots? Why is this field only blossoming now and not earlier? This Essay takes a look back at the origins of aminocatalysis and its development over the last century, and possibly reveals some surprises.

  9. Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Reviews
    8. Highlights
    9. Essay
    10. Review
    11. Communications
    12. Preview
    1. Polyoxometalates

      Polyoxometalates: Building Blocks for Functional Nanoscale Systems (pages 1736–1758)

      De-Liang Long, Ryo Tsunashima and Leroy Cronin

      Version of Record online: 3 FEB 2010 | DOI: 10.1002/anie.200902483

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      The broad field between discrete metal oxo complexes and solid-state oxides is ruled by the polyoxometalates and the structures formed from them by aggregation. This Review shows which suitable building blocks are available and how they can be combined to give nano- to micrometer-scale architectures.

  10. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Reviews
    8. Highlights
    9. Essay
    10. Review
    11. Communications
    12. Preview
    1. Porous Dynamical Materials

      Fast Molecular Rotor Dynamics Modulated by Guest Inclusion in a Highly Organized Nanoporous Organosilica (pages 1760–1764)

      Angiolina Comotti, Silvia Bracco, Patrizia Valsesia, Mario Beretta and Piero Sozzani

      Version of Record online: 8 FEB 2010 | DOI: 10.1002/anie.200906255

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      Rotor speed regulation in the hybrid walls of porous p-phenylenesilica can be achieved by guest uptake and removal. A graduation from slow to ultrafast motional regimes (k=104–108 s−1) can be experienced by the molecular rotors depending on guest nature and temperature, as detected by solid-state spin-echo 2H NMR spectroscopy (see picture).

    2. Cluster Compounds

      A Giant Silver Alkynyl Cage with Sixty Silver(I) Ions Clustered around Polyoxometalate Templates (pages 1765–1767)

      Juan Qiao, Kang Shi and Quan-Ming Wang

      Version of Record online: 5 FEB 2010 | DOI: 10.1002/anie.200906815

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      In a nutshell: A nanosized core/shell cluster has been synthesized by reaction of AgC[TRIPLE BOND]CtBu with AgOTf in the presence of a polyoxometalate (POM) template under solvothermal conditions. The peanutlike structure (see picture) consists of two Mo6O228− nuts (green) and an Ag60 shell (purple). Electrochemical studies revealed that the silver shell acts like an electronic relay, while the POM cores function as a redox buffer to stabilize the cluster.

    3. Polymerization

      Aufbaureaktion Redux: Scalable Production of Precision Hydrocarbons from AlR3 (R=Et or iBu) by Dialkyl Zinc Mediated Ternary Living Coordinative Chain-Transfer Polymerization (pages 1768–1772)

      Jia Wei, Wei Zhang and Lawrence R. Sita

      Version of Record online: 1 FEB 2010 | DOI: 10.1002/anie.200906658

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      Metal ménage à trois: Rapid and reversible chain transfer under living conditions between an active transition-metal propagating species, AlR3 as a primary surrogate, and a catalytic amount of ZnR2 as a secondary surrogate and chain-transfer mediator provides a cost-effective, scalable process for the production of precision hydrocarbons.

    4. O2 Evolution

      Evolution of O2 in a Seven-Coordinate RuIV Dimer Complex with a [HOHOH] Bridge: A Computational Study (pages 1773–1777)

      Jonas Nyhlén, Lele Duan, Björn Åkermark, Licheng Sun and Timofei Privalov

      Version of Record online: 12 FEB 2010 | DOI: 10.1002/anie.200906439

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      The missing link? DFT calculations demonstrate that a binuclear mechanism of O2 evolution involving seven-coordinate ruthenium species, which operates through the direct coupling of oxygen radicals and does not require crossing of prohibitively high potential-energy barriers, is plausible (see scheme).

    5. Helical Structures

      Parallel and Antiparallel Triple Helices of Naphthyridine Oligoamides (pages 1778–1781)

      Yann Ferrand, Amol M. Kendhale, Joachim Garric, Brice Kauffmann and Ivan Huc

      Version of Record online: 4 FEB 2010 | DOI: 10.1002/anie.200906401

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      Three, no less and no more, is the number of naphthyridine oligoamide strands that intertwine to form a unique and robust triple helix architecture. The formation of either a parallel or antiparallel arrangement of the helical strands is governed by factors such as the polarity of the solvent (see picture).

    6. Epitaxial Films

      Facile Chemical Solution Deposition of High-Mobility Epitaxial Germanium Films on Silicon (pages 1782–1785)

      Guifu Zou, Hongmei Luo, Filip Ronning, Baoquan Sun, Thomas M. McCleskey, Anthony K. Burrell, Eve Bauer and Q. X. Jia

      Version of Record online: 5 FEB 2010 | DOI: 10.1002/anie.200905804

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      Getting a move on: A facile chemical solution deposition method is used for the first time for the epitaxial growth of germanium on an silicon substrate. The germanium films show Hall mobility values as high as 1700 cm2 V−1 s−1 for a carrier concentration of 3.45×1019 cm−3 at room temperature.

    7. Endofullerenes

      Spin Divergence Induced by Exohedral Modification: ESR Study of Sc3C2@C80 Fulleropyrrolidine (pages 1786–1789)

      Taishan Wang, Jingyi Wu, Wei Xu, Junfeng Xiang, Xin Lu, Bao Li, Li Jiang, Chunying Shu and Chunru Wang

      Version of Record online: 5 FEB 2010 | DOI: 10.1002/anie.200906325

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      The paramagnetic properties of the endohedral fullerene Sc3C2@C80 are adjustable by exohedral modification by the Prato reaction (see picture). Analysis of spin densities and endocluster dynamics reveal unique paramagnetic properties of the Sc3C2@C80 fulleropyrrolidine and provide general insight into the addend-dependent paramagnetic behavior of endohedral fullerenes.

    8. Retinal Chromophores

      Probing and Modeling the Absorption of Retinal Protein Chromophores in Vacuo (pages 1790–1793)

      Jyoti Rajput, Dennis B. Rahbek, Lars H. Andersen, Amiram Hirshfeld, Mordechai Sheves, Piero Altoè, Giorgio Orlandi and Marco Garavelli

      Version of Record online: 26 JAN 2010 | DOI: 10.1002/anie.200905061

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      Seeing the light: A joint experimental and theoretical approach delivers the free gas-phase high-resolution absorption spectrum of the chromophore conformations implicated in the spectroscopy of retinal proteins (see scheme). Notably, many retinal pigments absorb close to the gas-phase value.

    9. Molecular Assemblies

      Supramolecular Assemblies Formed on an Epitaxial Graphene Superstructure (pages 1794–1799)

      Andrew J. Pollard, Edward W. Perkins, Nicholas A. Smith, Alex Saywell, Gudrun Goretzki, Anna G. Phillips, Stephen P. Argent, Hermann Sachdev, Frank Müller, Stefan Hüfner, Stefan Gsell, Martin Fischer, Matthias Schreck, Jürg Osterwalder, Thomas Greber, Simon Berner, Neil R. Champness and Peter H. Beton

      Version of Record online: 4 FEB 2010 | DOI: 10.1002/anie.200905503

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      Quite comparable: A graphene monolayer is used as a substrate for the growth of two-dimensional hydrogen-bonded supramolecular structures (see STM image). The formation of these extended structures arises from a commensurability between their dimensions and a moiré pattern formed by the graphene.

    10. Electron Transfer

      Electron Hopping over 100 Å Along an α Helix (pages 1800–1804)

      Yoko Arikuma, Hidenori Nakayama, Tomoyuki Morita and Shunsaku Kimura

      Version of Record online: 12 FEB 2010 | DOI: 10.1002/anie.200905621

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      Take the stepping stones: Electrons are exchanged between both termini of α-helical peptide self-assembled monolayers (SAMs) on gold by a hopping mechanism with the amide groups as hopping sites (see picture). The rate constant of 0.45 s−1 for the 64-mer peptide is significantly high for electron transfer through dielectric organic materials.

    11. Structural Biology

      Crystal Structure of HIV-1 Reverse Transcriptase Bound to a Non-Nucleoside Inhibitor with a Novel Mechanism of Action (pages 1805–1808)

      Séverine Freisz, Guillaume Bec, Marco Radi, Philippe Wolff, Emmanuele Crespan, Lucilla Angeli, Philippe Dumas, Giovanni Maga, Maurizio Botta and Eric Ennifar

      Version of Record online: 4 FEB 2010 | DOI: 10.1002/anie.200905651

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      Seeing the sites: Unlike classical non-nucleoside HIV-1 reverse transcriptase (RT) inhibitors (NNRTI; active site in blue), DAVP-1 is a non-nucleoside RT inhibitor that competes with the nucleotide substrate (NcRTI). The X-ray structure of DAVP-1 bound to the unligated RT shows a new inhibitor binding site close to the polymerase active site. (Nucleoside analogue RT inhibitor (NRTI) binding site is shown in red.)

    12. DNA Analysis

      DNA Analysis by Dynamic Chemistry (pages 1809–1812)

      Frank R. Bowler, Juan J. Diaz-Mochon, Michael D. Swift and Mark Bradley

      Version of Record online: 12 FEB 2010 | DOI: 10.1002/anie.200905699

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      Finding flaws: An enzyme-free method of DNA analysis raises the possibility of analyzing single-nucleotide polymorphism, indel, and abasic sites using mass spectrometry as a readout tool. The methodology is suitable for the dual analysis of heterozygous samples.

    13. Magnetic Resonance Imaging

      Nanotubular Paramagnetic Probes as Contrast Agents for Magnetic Resonance Imaging Based on the Diffusion Tensor (pages 1813–1815)

      Viviana Negri, Arisbel Cerpa, Pilar López-Larrubia, Laura Nieto-Charques, Sebastián Cerdán and Paloma Ballesteros

      Version of Record online: 5 FEB 2010 | DOI: 10.1002/anie.200906415

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      Added directionality: Exogenous nanotubular materials can be used to induce and perturb selectively the anisotropic diffusion of water molecules in the surrounding medium in a manner detectable by magnetic resonance imaging (see scheme; ADC: apparent translational diffusion coefficient). Nanotubes may be suitable contrast agents in studies of the microstructural basis of tissue anisotropy and its pathological implications.

    14. Masked Stannylenes

      Facile Interconversion of [Cp2(Cl)Hf(SnH3)] and [Cp2(Cl)Hf(μ-H)SnH2]: DFT Investigations of Hafnocene Stannyl Complexes as Masked Stannylenes (pages 1816–1819)

      Julie Guihaumé, Christophe Raynaud, Odile Eisenstein, Lionel Perrin, Laurent Maron and T. Don Tilley

      Version of Record online: 4 FEB 2010 | DOI: 10.1002/anie.200906476

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      Sn two-step: Dehydrocoupling of stannanes by the d0 complex [Cp2(Cl)HfH] preferentially occurs by two successive reactions (see scheme): σ-bond metathesis to form [Cp2(Cl)Hf(SnH3)] and subsequent stannylene transfer into the Cp2(Cl)Hf[BOND]SnH3 bond. [Cp2(Cl)Hf(SnH3)] readily isomerizes to a species possessing a reactive stannylene unit, [Cp2(Cl)Hf(μ-H)SnH2], thus making the stannylene-transfer reaction energetically feasible.

    15. Heterogeneous Catalysis

      Evidence for the Surface-Catalyzed Suzuki–Miyaura Reaction over Palladium Nanoparticles: An Operando XAS Study (pages 1820–1824)

      Peter J. Ellis, Ian J. S. Fairlamb, Simon F. J. Hackett, Karen Wilson and Adam F. Lee

      Version of Record online: 2 FEB 2010 | DOI: 10.1002/anie.200906675

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      No need to get away: X-ray absorption spectroscopy of catalytically active palladium nanoparticles during a Suzuki–Miyaura cross-coupling reaction revealed that the nanoparticles were stable under the reaction conditions, and that cross-coupling involved the direct participation of surface palladium defect sites in the catalytic cycle (see picture). Selective chemical and structural poisons provided further evidence for a heterogeneous active site.

    16. Asymmetric Catalysis

      Catalytic Enantioselective Dieckmann-Type Annulation: Synthesis of Pyrrolidines with Quaternary Stereogenic Centers (pages 1825–1829)

      Jonathan D. Hargrave, Joseph C. Allen, Gabriele Kociok-Köhn, Gerwyn Bish and Christopher G. Frost

      Version of Record online: 4 FEB 2010 | DOI: 10.1002/anie.200907067

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      A new trick for an old dog: A Dieckmann-type cyclization was used to synthesize the title compounds with up to 96 % ee (see scheme; Bn=benzyl). The presence of a β coordinating functionality in the substrate induces a competition between cyclization and elimination pathways that is influenced by the nature of the chiral ligand. A mechanistic rationale is proposed to account for these observations.

    17. Cycloaddition Reactions

      Synthesis of Nine-Membered Carbocycles by the [4+3+2] Cycloaddition Reaction of Ethyl Cyclopropylideneacetate and Dienynes (pages 1830–1833)

      Shinichi Saito, Kyotaro Maeda, Ryu Yamasaki, Takuya Kitamura, Minami Nakagawa, Korehito Kato, Isao Azumaya and Hyuma Masu

      Version of Record online: 9 FEB 2010 | DOI: 10.1002/anie.200907052

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      Various dienynes reacted efficiently with ethyl cyclopropylideneacetate in the presence of [Ni(cod)2]/PPh3, and cyclononadienes were synthesized in a selective manner. Dienynes tethered with aromatic rings were very good substrates, and the corresponding tricyclic compounds were isolated in high yields. The reaction provides a new route for the synthesis of nine-membered carbocycles (see scheme).

    18. Chemoselectivity

      Allylic Substitution versus Suzuki Cross-Coupling: Capitalizing on Chemoselectivity with Bifunctional Substrates (pages 1834–1837)

      Mahmud M. Hussain and Patrick J. Walsh

      Version of Record online: 4 FEB 2010 | DOI: 10.1002/anie.200905399

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      One catalyst, two reactions—a tale of chemoselectivity: Given the choice between an allylic acetate and a vinylboronate ester, palladium preferentially reacts with the allylic acetate to give the allylic substitution product. In the presence of an aryl bromide and base, Suzuki cross-coupling subsequently ensues to afford allylic amines (see scheme; pin=pinacol, THF=tetrahydrofuran).

    19. Asymmetric Catalysis

      Indium(I)-Catalyzed Asymmetric Allylation, Crotylation, and α-Chloroallylation of Hydrazones with Rare Constitutional and High Configurational Selectivities (pages 1838–1841)

      Ananya Chakrabarti, Hideyuki Konishi, Miyuki Yamaguchi, Uwe Schneider and Shū Kobayashi

      Version of Record online: 4 FEB 2010 | DOI: 10.1002/anie.200906308

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      The hydra-zone: The first example of asymmetric InI catalysis had been developed. InI combined with a chiral semicorrin ligand (L*) is an effective catalyst for enantioselective allylation, crotylation, and α-chloroallylation of hydrazones. In the two latter cases, C[BOND]C bond formations proceeded with high selectivity where both reactive aliphatic C[BOND]Cl and aromatic O[BOND]H bonds were tolerated.

    20. Radicals

      A Persistent Dipotassium 1,2,4-Diazaphospholide Radical Complex: Synthesis, X-Ray Structure, and Bonding (pages 1842–1845)

      Chengfu Pi, Yan Wang, Wenjun Zheng, Li Wan, Haoyu Wu, Linhong Weng, Limin Wu, Qianshu Li and Paul von Ragué Schleyer

      Version of Record online: 5 FEB 2010 | DOI: 10.1002/anie.200906303

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      Staying power: A persistent 1,2,4-diazaphospholide dianion radical complex (see picture; N blue, P purple, K teal, O red) with a triple-decker conformation was prepared by one-electron reduction of 1,2,4-diazaphospholide anion with potassium in the presence of [18]crown-6. Computations suggested that the unpaired electron in the [3,5-Ph2dp].2− radical anion is delocalized (spin density: pink) to all three rings of the 1,2,4-diazaphospholide and the phosphorus atom.

    21. Boronic Acids

      Direct Conversion of Arylamines to Pinacol Boronates: A Metal-Free Borylation Process (pages 1846–1849)

      Fanyang Mo, Yubo Jiang, Di Qiu, Yan Zhang and Jianbo Wang

      Version of Record online: 1 FEB 2010 | DOI: 10.1002/anie.200905824

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      Leave the metal out: Arylboronates are produced in moderate to good yields by direct borylation of readily available aryl amines (see scheme). The reaction can be carried out under air at room temperature and transition-metal catalysis is not required. The boronate products can be used without purification in Suzuki–Miyaura cross-coupling reactions.

    22. Transacylation

      General and Chemoselective N-Transacylation of Secondary Amides by Means of Perfluorinated Anhydrides (pages 1850–1853)

      Paola Rota, Pietro Allevi, Raffaele Colombo, Maria L. Costa and Mario Anastasia

      Version of Record online: 9 FEB 2010 | DOI: 10.1002/anie.200906055

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      A direct route: The N-transacylation of secondary amides to their perfluorinated analogues with the possibility of subsequent conversion into a normal amide is reported (see scheme). This reaction occurs in the presence of a variety of functional groups that are labile to the hydrolysis conditions required by classical N-transacylation.

    23. Molecular Devices

      Photochromic Supramolecular Memory With Nondestructive Readout (pages 1854–1857)

      Joakim Kärnbratt, Martin Hammarson, Shiming Li, Harry L. Anderson, Bo Albinsson and Joakim Andréasson

      Version of Record online: 3 FEB 2010 | DOI: 10.1002/anie.200906088

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      Looking without touching: The light-controlled isomerization of a complex containing a pyridine-appended dithienylethene (DTE; green) and a porphyrin dimer induces dramatic structural and spectral changes (see picture). These changes are monitored in a region outside the photochromically active absorption bands of DTE, therefore allowing a nondestructive readout so that the process functions as a molecular optically controlled memory.

    24. Organocatalysis

      Asymmetric Direct Vinylogous Aldol Reaction of Furanone Derivatives Catalyzed by an Axially Chiral Guanidine Base (pages 1858–1861)

      Hitoshi Ube, Naoki Shimada and Masahiro Terada

      Version of Record online: 4 FEB 2010 | DOI: 10.1002/anie.200906647

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      Ace of Base: The first highly enantioselective direct vinylogous aldol reaction of dihalogenated or α-thio-substituted furanones with aldehydes utilizes an axially chiral guanidine base catalyst. The method provides facile access to enantioenriched γ-substituted butenolides.

    25. Mesoporous Materials

      Self-Assembled TiO2 Nanocrystal Clusters for Selective Enrichment of Intact Phosphorylated Proteins (pages 1862–1866)

      Zhenda Lu, Miaomiao Ye, Ni Li, Wenwan Zhong and Yadong Yin

      Version of Record online: 12 FEB 2010 | DOI: 10.1002/anie.200906648

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      Mesoporous traps: The title clusters were fabricated through self-assembly of nanocrystals in emulsion droplets and subsequent protective calcination. The specific affinity offered by the metal oxide and the size-exclusion mechanism enabled by the mesoporous structure enable the use of these clusters for efficient enrichment of intact phosphorylated proteins from complex biological samples (see picture).

    26. Homogeneous Catalysis

      A Recyclable Nanoparticle-Supported Palladium Catalyst for the Hydroxycarbonylation of Aryl Halides in Water (pages 1867–1870)

      Sebastian Wittmann, Alexander Schätz, Robert N. Grass, Wendelin J. Stark and Oliver Reiser

      Version of Record online: 19 FEB 2010 | DOI: 10.1002/anie.200906166

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      Boomerang catalysis: A catalyst catch–release system is established by the noncovalent attachment of a Pd N-heterocyclic carbene complex to graphene-coated magnetic Co nanoparticles. The immobilization by pyrene tags (see scheme; blue) is reversible at elevated temperatures, releasing the homogeneous catalyst. The hydroxycarbonylation of aryl halides is performed in 16 iterative reactions with this highly active catalyst.

    27. Hydrogen Storage

      Methylguanidinium Borohydride: An Ionic-Liquid-Based Hydrogen-Storage Material (pages 1871–1873)

      Amir Doroodian, Joachim E. Dengler, Alexander Genest, Notker Rösch and Bernhard Rieger

      Version of Record online: 9 FEB 2010 | DOI: 10.1002/anie.200905359

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      Promising: The ionic liquid methylguanidinium borohydride (see picture; blue N, yellow B, gray C, white H) is able to release 9 wt % hydrogen under thermal and catalytic conditions. The thermodynamic features and the products of the dehydrogenation are also investigated.

    28. Organocopper Reagents

      A Cobalt-Catalyzed Sulfonate/Copper Exchange for the Preparation of Highly Functionalized Electron-Deficient Aryl Copper Reagents (pages 1874–1877)

      Christoph J. Rohbogner, Coura R. Diène, Tobias J. Korn and Paul Knochel

      Version of Record online: 5 FEB 2010 | DOI: 10.1002/anie.200905379

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      Organocopper reagents from phenols: A new cobalt-catalyzed aryl sulfonate/copper exchange reaction allows the synthesis of highly functionalized aryl copper reagents from sulfonates bearing electron-deficient substituents under mild conditions (25–45 °C, 1–6 h; see example). Sensitive functional groups, such as aldehydes, esters, and nitriles, are well-tolerated.

    29. Group 13 Ligands

      Selective Oxidative Cleavage of Cp* from Coordinated GaCp*: Naked Ga+ in [GaNi(GaCp*)4]+ and [(μ2-Ga)nM3(GaCp*)6]n+ (pages 1878–1881)

      Markus Halbherr, Timo Bollermann, Christian Gemel and Roland A. Fischer

      Version of Record online: 2 FEB 2010 | DOI: 10.1002/anie.200905920

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      The naked and the edge: The selective oxidative cleavage of Cp* from coordinated GaCp* ligands lead to the cluster cations [(μ2-Ga)2Pd3(GaCp*)6]2+ and [(μ2-Ga)Pt3(GaCp*)6]+ (see structure) which are the first examples of the edge-bridging coordination mode of “naked” Ga+. This chemistry is a step towards a rational synthesis of metal-rich molecules as discrete models for intermetallic phases.

    30. Membrane Proteins

      The Native Conformation of the Human VDAC1 N Terminus (pages 1882–1885)

      Robert Schneider, Manuel Etzkorn, Karin Giller, Venita Daebel, Jörg Eisfeld, Markus Zweckstetter, Christian Griesinger, Stefan Becker and Adam Lange

      Version of Record online: 5 FEB 2010 | DOI: 10.1002/anie.200906241

      Thumbnail image of graphical abstract

      Roll out the barrel: The conformation of the N-terminal domain of a functional human voltage-dependent anion channel (hVDAC1) in lipid bilayers has been determined (see picture; overlay of NMR model (blue) and X-ray structure (red/gray)). Solid-state NMR spectroscopy reveals that the N terminus assumes a well-defined, rigid structure and that its removal induces a conformational change in the hVDAC1 β-barrel.

    31. Noble Metalates

      Polyoxometalates Made of Gold: The Polyoxoaurate [AuIII4AsV4O20]8− (pages 1886–1889)

      Natalya V. Izarova, Nina Vankova, Thomas Heine, Rosa Ngo Biboum, Bineta Keita, Louis Nadjo and Ulrich Kortz

      Version of Record online: 17 FEB 2010 | DOI: 10.1002/anie.200905566

      Thumbnail image of graphical abstract

      More noble than ever: The first fully inorganic discrete polynuclear gold(III) oxo complex [AuIII4AsV4O20]8− (see structure; Au yellow, As blue, O red) was prepared by condensation of [Au(OH)4] in the presence of AsO43− ions under mild reaction conditions. The resulting polyoxoaurate exhibits a tetrameric structure with square-planar coordinated AuIII ions linked by oxo and arsenate bridging ligands.

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