Angewandte Chemie International Edition

Cover image for Vol. 47 Issue 10

February 22, 2008

Volume 47, Issue 10

Pages 1789–1965

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Reviews
    7. Highlights
    8. Essay
    9. Review
    10. Communications
    11. Preview
    1. Cover Picture: Polymer Vesicles Containing Small Vesicles within Interior Aqueous Compartments and pH-Responsive Transmembrane Channels (Angew. Chem. Int. Ed. 10/2008) (page 1789)

      Hsin-Cheng Chiu, Yue-Wen Lin, Yi-Fong Huang, Chih-Kai Chuang and Chorng-Shyan Chern

      Version of Record online: 15 FEB 2008 | DOI: 10.1002/anie.200890035

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      Multivesicle assemblies represent a new supramolecular arrangement similar to eukaryotic cells and their subcellular organelles, as described by H.-C. Chiu and co-workers in their Communication on page 1875 ff. These assemblies are prepared by two-stage double emulsion of copolymers comprising acrylic acid and the acrylate of 1,2-distearoyl-rac-glycerol. They exhibit pH-responsive transmembrane channels, which allow compartmentalization of various chemicals within a vesicle and facile control of their encapsulation and release.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Reviews
    7. Highlights
    8. Essay
    9. Review
    10. Communications
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    1. Inside Cover: Control of Intramolecular Orbital Alignment in the Photodissociation of Thiophenol: Conformational Manipulation by Chemical Substitution (Angew. Chem. Int. Ed. 10/2008) (page 1790)

      Jeong Sik Lim, Yoon Sup Lee and Sang Kyu Kim

      Version of Record online: 15 FEB 2008 | DOI: 10.1002/anie.200890036

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      Conformational control by chemical substitution influences the content of the wavepacket propagating along the S[BOND]H coordinate of thiophenol. The wide spread of the wavepacket at the conical intersection, induced by the conformation of the S[BOND]H torsional angle, diminishes the probability of diabatic passage, thus giving control over the branching ratio of excited and ground states of product. In the Communication on page 1853 ff., S. K. Kim and co-workers describe this approach to control intramolecular orbital alignment for the phenylthiyl radical.

  3. Graphical Abstract

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

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

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

    1. Top of page
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    4. Graphical Abstract
    5. News
    6. Book Reviews
    7. Highlights
    8. Essay
    9. Review
    10. Communications
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    1. Cooperating Ligands in Catalysis (pages 1814–1818)

      Hansjörg Grützmacher

      Version of Record online: 31 JAN 2008 | DOI: 10.1002/anie.200704654

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      Let's stick together: Cooperating ligands participate directly in bond activation and thereby undergo a reversible chemical transformation. The interplay between metal center and ligand may facilitate a chemical process. In transition-metal-catalyzed reactions, this concept allows the discovery of new chemical reactions, such as the dehydrogenative coupling of primary alcohols and primary amines to amides and molecular hydrogen (see scheme).

    2. Formation of Carbanions Using Neutral Organic Molecules as Electron-Transfer Reagents: A Radical Concept (pages 1819–1823)

      Gerard P. McGlacken and Tanweer A. Khan

      Version of Record online: 31 JAN 2008 | DOI: 10.1002/anie.200704883

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      A new generation of organic compounds (see examples) have been developed and used as single- and double-electron donors. Aryl halides and sulfones can be reduced, and using one particular electron donor, aryl anions can be formed. Up until now these reactions were mainly carried out by metals.

  7. Essay

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    8. Essay
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    10. Communications
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    1. Karl Lohmann and the Discovery of ATP (pages 1824–1827)

      Peter Langen and Ferdinand Hucho

      Version of Record online: 22 JAN 2008 | DOI: 10.1002/anie.200702929

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      Close, but no cigar. Why didn't Karl Lohmann, the discoverer of ATP, receive the Nobel Prize? This essay describes the life of the prominent biochemist, teacher, and administrator, who wasn't honored with this highest scientific distinction.

  8. Review

    1. Top of page
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    4. Graphical Abstract
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    8. Essay
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    10. Communications
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    1. Energy-Efficient Syngas Production through Catalytic Oxy-Methane Reforming Reactions (pages 1828–1847)

      Tushar V. Choudhary and Vasant R. Choudhary

      Version of Record online: 10 JAN 2008 | DOI: 10.1002/anie.200701237

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      The commercial catalytic reforming of methane into synthesis gas (syngas), an extremely versatile intermediate, requires the development of efficient heterogeneous catalysts. As long-term performance of the catalyst is crucial for wide-scale commercialization of the oxy reforming process, catalyst-related studies are abundant and are summarized in this Review.

  9. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Reviews
    7. Highlights
    8. Essay
    9. Review
    10. Communications
    11. Preview
    1. Multicomponent Assembly of Boronic Acid Based Macrocycles and Cages (pages 1848–1852)

      Nicolas Christinat, Rosario Scopelliti and Kay Severin

      Version of Record online: 22 JAN 2008 | DOI: 10.1002/anie.200705272

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      Simple one-pot reactions: Boronate ester condensation reactions can be combined with imine condensations and metal–ligand interactions to build nanometer-sized macrocycles and cages in one step from small building blocks (see scheme).

    2. Control of Intramolecular Orbital Alignment in the Photodissociation of Thiophenol: Conformational Manipulation by Chemical Substitution (pages 1853–1856)

      Jeong Sik Lim, Yoon Sup Lee and Sang Kyu Kim

      Version of Record online: 7 FEB 2008 | DOI: 10.1002/anie.200705358

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      Intramolecular orbital alignment can be controlled by conformational tuning of the initial wavepacket location on the two-dimensional potential-energy surfaces of thiophenol (see picture; CI=conical intersection). Chemical substitution induces conformational preference, leading to a dramatic change of the branching ratio between X̃ and à states of the phenylthiyl radical.

    3. Valence-Tautomeric Metal–Organic Nanoparticles (pages 1857–1860)

      Inhar Imaz, Daniel Maspoch, Clara Rodríguez-Blanco, José Manuel Pérez-Falcón, Javier Campo and Daniel Ruiz-Molina

      Version of Record online: 28 JAN 2008 | DOI: 10.1002/anie.200705263

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      Metal–organic nanoparticles (see SEM image) showing valence-tautomeric behavior have been obtained by a versatile approach involving precipitation and coordination polymerization. They undergo reversible temperature-dependent interconversion between low- and high-spin forms, as revealed by plotting the magnetic moment χ as a function of temperature.

    4. Shaping Supramolecular Nanofibers with Nanoparticles Forming Complementary Hydrogen Bonds (pages 1861–1865)

      Josep Puigmartí-Luis, Ángel Pérez del Pino, Elena Laukhina, Jordi Esquena, Vladimir Laukhin, Concepció Rovira, José Vidal-Gancedo, Antonios G. Kanaras, Richard J. Nichols, Mathias Brust and David B. Amabilino

      Version of Record online: 31 JAN 2008 | DOI: 10.1002/anie.200704864

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      Functionalized gold nanoparticles with complementary H-bonding groups can control the secondary structure of xerogel fibers formed by a molecular conductor thanks to their incorporation into the nanowires, which show metal-like conductivity once doped without the need for annealing. The picture shows a photograph of the xerogel, TEM images of Au particles in the gel and a single fiber, and an AFM image revealing the texture of the gel.

    5. Sulfate Recognition by Persistent Crystalline Capsules with Rigidified Hydrogen-Bonding Cavities (pages 1866–1870)

      Radu Custelcean, Priscilla Remy, Peter V. Bonnesen, De-en Jiang and Bruce A. Moyer

      Version of Record online: 31 JAN 2008 | DOI: 10.1002/anie.200704937

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      Locked up: The sulfate anion is selectively encapsulated into rigid hydrogen-bonded capsules upon crystallization of a simple and flexible urea-functionalized ligand in the presence of Mg2+ ions and water (see structure; sulfate: space-filling). The resulting framework persists in the presence of different-shaped anions, allowing the shape selectivity of hydrogen-bonding hosts to be evaluated, and providing a simple way to separate the environmentally relevant sulfate from highly competitive mixtures of aqueous anions.

    6. Tripeptides as Efficient Asymmetric Catalysts for 1,4-Addition Reactions of Aldehydes to Nitroolefins–A Rational Approach (pages 1871–1874)

      Markus Wiesner, Jefferson D. Revell and Helma Wennemers

      Version of Record online: 28 JAN 2008 | DOI: 10.1002/anie.200704972

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      Bridging the gap: Conformational analysis of a peptidic catalyst for aldol reactions led to the development of H-D-Pro-Pro-Asp-NH2 as a highly efficient catalyst for conjugate addition reactions between aldehydes and nitroolefins (see scheme). Only 1 mol % of catalyst suffices to obtain γ-nitroaldehydes in excellent yields and stereoselectivities.

    7. Polymer Vesicles Containing Small Vesicles within Interior Aqueous Compartments and pH-Responsive Transmembrane Channels (pages 1875–1878)

      Hsin-Cheng Chiu, Yue-Wen Lin, Yi-Fong Huang, Chih-Kai Chuang and Chorng-Shyan Chern

      Version of Record online: 4 JAN 2008 | DOI: 10.1002/anie.200704078

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      Multivesicle assemblies with pH-responsive transmembrane channels in the vesicle walls (see picture) were made by two-step double emulsion of copolymers comprising acrylic acid and acrylate of 1,2-distearoyl-rac-glycerol. These assemblies mimic eukaryotic cells, which contain functional organelles within the cell walls.

    8. Inhibition of HIV-1 Fusion by Hydrogen-Bond-Surrogate-Based α Helices (pages 1879–1882)

      Deyun Wang, Min Lu and Paramjit S. Arora

      Version of Record online: 25 JAN 2008 | DOI: 10.1002/anie.200704227

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      Inhibition with a twist: An artificial α helix obtained by replacing an N-terminal main-chain i and i+4 hydrogen bond with a carbon–carbon bond (see structure) inhibits gp41-mediated cell fusion. This work suggests that hydrogen-bond-surrogate-derived helices may provide a general class of scaffolds for the generation of leads against viral entry.

    9. Gold-Catalyzed Allyl–Allyl Coupling (pages 1883–1886)

      Susana Porcel, Verónica López-Carrillo, Cristina García-Yebra and Antonio M. Echavarren

      Version of Record online: 29 JAN 2008 | DOI: 10.1002/anie.200704500

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      Gold rings: Cationic gold(I) complexes efficiently catalyze the intramolecular allyl–allyl coupling of allyl acetates with allylstannanes with excellent stereoselectivity (see scheme). This reaction is mechanistically very different from that catalyzed by palladium.

    10. Iron-Catalyzed Asymmetric Olefin cis-Dihydroxylation with 97 % Enantiomeric Excess (pages 1887–1889)

      Ken Suzuki, Paul D. Oldenburg and Lawrence Que Jr.

      Version of Record online: 31 JAN 2008 | DOI: 10.1002/anie.200705061

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      Bigcis-ster: The use of an (R,R)-bipyrrolidine backbone with two α-methylpyridine pendant arms affords a tetradentate N4 ligand that coordinates an iron center with cis-α topology (see picture; Fe purple, C gray, N blue, O red, S yellow, F green). This complex catalyzes the reaction between H2O2 and cis-2-heptene to afford a cis-diol product in very high enantioselectivity.

    11. Lewis Base Activation of Lewis Acids: Catalytic Enantioselective Glycolate Aldol Reactions (pages 1890–1892)

      Scott E. Denmark and Won-jin Chung

      Version of Record online: 31 JAN 2008 | DOI: 10.1002/anie.200705499

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      Bothsyn- andanti-1,2-diols can be obtained with high diastereoselectivity and enantioselectivity from the properly substituted glycolate-derived silyl ketene acetals in the presence of SiCl4 and a chiral bisphosphoramide catalyst (see scheme; TMS=trimethylsilyl, TBS=tert-butyldimethylsilyl). The sense of diastereoselectivity can be reversed by changing the size of the substituents on the silyl ketene acetals.

    12. α-Olefins as Alkenylmetal Equivalents in Catalytic Conjugate Addition Reactions (pages 1893–1895)

      Chun-Yu Ho, Hirohisa Ohmiya and Timothy F. Jamison

      Version of Record online: 31 JAN 2008 | DOI: 10.1002/anie.200705163

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      In the presence of a silyl triflate and an amine base, a nickel–phosphine complex catalyzes the direct conjugate addition of ethylene, α-olefins, and aryl alkenes to unsaturated aldehydes and ketones. The enolsilane products are isolated in good to very high yield, and in very high stereoselectivity for some cases. The alkene is a functional equivalent of an alkenylmetal reagent in the transformation.

    13. Contrasting cis and trans Effects on the Reactivity of Nonheme Oxoiron(IV) Complexes (pages 1896–1899)

      Yuming Zhou, Xiaopeng Shan, Rubén Mas-Ballesté, Michael R. Bukowski, Audria Stubna, Mrinmoy Chakrabarti, Luke Slominski, Jason A. Halfen, Eckard Münck and Lawrence Que Jr.

      Version of Record online: 28 JAN 2008 | DOI: 10.1002/anie.200704228

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      Position determines properties: The oxidative properties of [FeIV(O)(L)(X)] species (L=tetradentate N4 ligand, X=monodentate ligand) depend on the position of the X ligand. The Fe[DOUBLE BOND]O unit is a poorer oxidant with an electron-donating cis ligand but becomes a much better oxidant when this ligand is trans to the oxo group. This difference in reactivity reflects perturbations to the electronic structure of the highly covalent Fe[DOUBLE BOND]O moiety.

    14. Neutral H2O2 Synthesis by Electrolysis of Water and O2 (pages 1900–1902)

      Ichiro Yamanaka and Toru Murayama

      Version of Record online: 25 JAN 2008 | DOI: 10.1002/anie.200704431

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      Direct, safe, and continuous synthesis of neutral H2O2 solutions with concentrations of up to 8 wt % from O2 and water has been accomplished by an improved electrolysis method involving a solid-polymer electrolyte (SPE). The formation and accumulation of neutral H2O2 were strongly enhanced by exposing the cathode to a stream of O2.

    15. Tetrasubstituted Furans by a PdII-Catalyzed Three-Component Michael Addition/Cyclization/Cross-Coupling Reaction (pages 1903–1906)

      Yuanjing Xiao and Junliang Zhang

      Version of Record online: 29 JAN 2008 | DOI: 10.1002/anie.200704531

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      Dual personalities: PdII-catalyzed three-component Michael addition/cyclization/cross-coupling reaction provides an efficient route to functionalized tetraubstituted furans (see scheme). The [PdCl2(CH3CN)2] catalyst plays a dual role in this transformation as both a Lewis acid and a transition-metal center.

    16. Synthesis of Aryl Glycines by the α Arylation of Weinreb Amides (pages 1907–1909)

      Sebastian Hirner, Olaf Panknin, Magnus Edefuhr and Peter Somfai

      Version of Record online: 25 JAN 2008 | DOI: 10.1002/anie.200704689

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      A rare example of the umpolung of an enolate forms the basis of the title reaction. In this procedure, a Grignard reagent is added to the iminium ion formed from the Weinreb amide upon treatment with a base (see scheme). When a chiral amide was used as the starting material, the nucleophilic addition proceeded with high diastereoselectivity. LDA = lithium diisopropylamide.

    17. Avian Influenza H5-Containing Virus-Like Particles (VLPs): Host-Cell Receptor Specificity by STD NMR Spectroscopy (pages 1910–1912)

      Thomas Haselhorst, Jean-Michel Garcia, Tasneem Islam, Jimmy C. C. Lai, Faith J. Rose, John M. Nicholls, J. S. Malik Peiris and Mark von Itzstein

      Version of Record online: 29 JAN 2008 | DOI: 10.1002/anie.200704872

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      Gripped by the flu: The emergence of a human pandemic influenza virus from an avian progenitor involves a switch in preferential binding of the influenza virus hemagglutinin (HA). Saturation transfer difference NMR spectroscopy of avian H5 chimeric virus-like particles (VLPs) encoding viral HA in a complex with α(2,3)-and α(2,6)-linked N-acetylneuraminides (3′SL and 6′SL, respectively) has shown that avian influenza H5-containing VLPs clearly discriminate between α(2,3)- and α(2,6)-linkages.

    18. Heterolytic Dihydrogen Activation by a Sulfido- and Oxo-Bridged Dinuclear Germanium–Ruthenium Complex (pages 1913–1915)

      Tsuyoshi Matsumoto, Yukiko Nakaya and Kazuyuki Tatsumi

      Version of Record online: 25 JAN 2008 | DOI: 10.1002/anie.200704899

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      Cooperation of soft and hard bridging ligands (μ-S and μ-O, respectively) is crucial to the mechanism of heterolytic dihydrogen activation by germanium–ruthenium complex 1 to give syn and anti isomers of the corresponding hydroxogermanium–hydridoruthenium complex 2 (see scheme; dep=2,6-diethylphenyl).

    19. Growth of Aligned TiO2 Bamboo-Type Nanotubes and Highly Ordered Nanolace (pages 1916–1919)

      Sergiu P. Albu, Doohun Kim and Patrik Schmuki

      Version of Record online: 29 JAN 2008 | DOI: 10.1002/anie.200704144

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      Alternating-voltage anodization of titanium foil in a fluoride-containing electrolyte allowed novel, self-organized nanoscale morphologies of TiO2 to be grown, such as reinforced nanotubes (nanobamboo) and laterally extended two-dimensional networks (nanolace).

    20. From an N-Methyl N-Heterocyclic Carbene to Carbyne and Carbide Ligands via Multiple C[BOND]H and C[BOND]N Bond Activations (pages 1920–1922)

      Javier A. Cabeza, Ignacio del Río, Daniel Miguel and M. Gabriela Sánchez-Vega

      Version of Record online: 31 JAN 2008 | DOI: 10.1002/anie.200705154

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      Multiple choices: The carbyne C atom of 1 and the carbide of 2 arise from an N-methyl group of 1,3-dimethylimidazol-2-ylidene. The synthesis of complex 1, which involves activation of the three C[BOND]H bonds of an N-methyl group, and that of complex 2, which requires additional activation of the C[BOND]N bond, provide new examples of metal-mediated degradation of N-heterocyclic carbenes.

    21. Organic Dye-Sensitized Ionic Liquid Based Solar Cells: Remarkable Enhancement in Performance through Molecular Design of Indoline Sensitizers (pages 1923–1927)

      Daibin Kuang, Satoshi Uchida, Robin Humphry-Baker, Shaik M. Zakeeruddin and Michael Grätzel

      Version of Record online: 23 JAN 2008 | DOI: 10.1002/anie.200705225

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      A power conversion efficiency of more than 7.2 % under AM 1.5 sunlight (100 mW cm−2) is reported for the first time for an organic-dye-sensitized solar cell used in conjunction with a newly developed binary ionic-liquid (solvent-free) electrolyte (see current–voltage plot and photocurrent action spectrum for the sensitizer D205, the highest occupied molecular orbital of which is shown).

    22. Direct, Iridium-Catalyzed Enantioselective and Regioselective Allylic Etherification with Aliphatic Alcohols (pages 1928–1931)

      Satoshi Ueno and John F. Hartwig

      Version of Record online: 31 JAN 2008 | DOI: 10.1002/anie.200705267

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      From alcohol to ether: Iridium-catalyzed allylations yield α chiral ether derivatives directly from aliphatic alcohols with a simple alkali metal base (see equation). These reactions form ethers from primary, secondary, and tertiary alkoxides with high enantioselectivity. By-products from isomerization were suppressed by the use of an alkyne additive.

    23. C[BOND]H Functionalization/C[BOND]N Bond Formation: Copper-Catalyzed Synthesis of Benzimidazoles from Amidines (pages 1932–1934)

      Gordon Brasche and Stephen L. Buchwald

      Version of Record online: 28 JAN 2008 | DOI: 10.1002/anie.200705420

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      Copper closes the ring: Benzimidazoles are synthesized from amidines through a copper-catalyzed C[BOND]H functionalization/C[BOND]N bond-forming process. The method tolerates a broad range of functional groups and provides the benzimidazoles in up to 89 % yield. Best results are obtained by using 15 mol % Cu(OAc)2, 2–5 equivalents of HOAc as additive, and oxygen as the stoichiometric reoxidant (see scheme).

    24. The Telescoped Intramolecular Michael/Olefination (TIMO) Approach to α-Alkylidene-γ-butyrolactones: Synthesis of (+)-Paeonilactone B (pages 1935–1937)

      Michael G. Edwards, Martin N. Kenworthy, Russell R. A. Kitson, Mark S. Scott and Richard J. K. Taylor

      Version of Record online: 28 JAN 2008 | DOI: 10.1002/anie.200705329

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      Scoping out TIMO: A telescoped intramolecular Michael addition/proton transfer/Horner–Wadsworth–Emmons olefination sequence was developed to provide rapid access to α-alkylidene-γ-butyrolactones (see scheme). The method was applied to prepare a range of tetrahydrobenzofuran-2,5-diones and related systems, and it was utilized in a short synthesis of enantiomerically pure (+)-paeonilactone B.

    25. Spectroscopically Enhancing Electrical Nanotraps (pages 1938–1941)

      Gengfeng Zheng, Lidong Qin and Chad A. Mirkin

      Version of Record online: 28 JAN 2008 | DOI: 10.1002/anie.200705312

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      Electrical traps with Raman hot spots: On-wire-lithography (OWL) nanotraps electrically localize DNA in a nanometer-scale gap (see picture, red oligonucleotides with Raman dyes), which allows for the identification of the localized material by surface-enhanced Raman spectroscopy. With microfluidic delivery, sample volumes as small as 1 μL with target concentrations as low as 230 fM can be studied without secondary amplification.

    26. Bacterial Biosynthesis of a Multipotent Stilbene (pages 1942–1945)

      Susan A. Joyce, Alexander O. Brachmann, Itamar Glazer, Lea Lango, Gertrud Schwär, David J. Clarke and Helge B. Bode

      Version of Record online: 31 JAN 2008 | DOI: 10.1002/anie.200705148

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      Commuting between kingdoms: The biosynthesis of the only nonplant stilbene 1 from Photorhabdus bacteria has been solved by identification of all the genes involved in its biosynthesis and by feeding experiments. Stilbene 1 is derived from the condensation of two β-ketoacyl thioesters and is required for the normal development of Heterorhabditis nematodes, the natural host of Photorhabdus.

    27. Activation of Methane by Oligomeric (Al2O3)x+ (x=3,4,5): The Role of Oxygen-Centered Radicals in Thermal Hydrogen-Atom Abstraction (pages 1946–1950)

      Sandra Feyel, Jens Döbler, Robert Höckendorf, Martin K. Beyer, Joachim Sauer and Helmut Schwarz

      Version of Record online: 28 JAN 2008 | DOI: 10.1002/anie.200704791

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      A matter of radical sites and bond energies: Experimental and theoretical studies show that the cationic polynuclear aluminum oxide clusters, which are oligomeric systems of (Al2O3)x+ (x=3, 4, 5), activate methane at room temperature (see picture). In contrast, clusters with an odd number of aluminum atoms are unreactive.

    28. Structural Evidence for Antiaromaticity in Free Boroles (pages 1951–1954)

      Holger Braunschweig, Israel Fernández, Gernot Frenking and Thomas Kupfer

      Version of Record online: 28 JAN 2008 | DOI: 10.1002/anie.200704771

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      Pentaphenylborole and a ferrocenylborole were synthesized and structurally characterized. Both experimental and theoretical data reveal that rather weak intermolecular interactions are able to significantly alter the bond lengths in the borole ring of pentaphenylborole (see picture). Moreover, the high Lewis acidity of boroles is demonstrated by a significant Fe⋅⋅⋅B interaction in the ferrocenylborole in the solid state.

    29. Strongly Oxidizing and Reducing Functions Combined in a Single Compound: An Alkyl Gallium Peroxide Possessing a Nine-Membered (GaR)3(O2)3 Heterocycle (pages 1955–1957)

      Werner Uhl and Mohammad Reza Halvagar

      Version of Record online: 28 JAN 2008 | DOI: 10.1002/anie.200704739

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      Organoelement peroxides of the heavier Group 13 elements form a class of extraordinarily reactive compounds, which decompose spontaneously by intramolecular redox processes as a result of the close contact of oxidizing peroxo groups and reducing E[BOND]C bonds. The synthesis of a unique compound is presented, in which three peroxo ligands bridge three alkyl gallium groups by the formation of a nine-membered heterocycle (see structural formula).

    30. Syntheses with a Chiral Building Block from the Citric Acid Cycle: (2R,3S)-Isocitric Acid by Fermentation of Sunflower Oil (pages 1958–1960)

      Philipp Heretsch, Franziska Thomas, Andreas Aurich, Harald Krautscheid, Dieter Sicker and Athanassios Giannis

      Version of Record online: 31 JAN 2008 | DOI: 10.1002/anie.200705000

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      No longer just analytical: Previously, (2R,3S)-isocitric acid (1), a component of the citric acid cycle, had not been available on a preparative scale. A new route to this acid on a kilogram scale combines a biotechnological formation through fermentation from sunflower oil with a chemical separation process. In a variety of transformations into further chiral derivatives, 1 is established as a valuable new member of the chiral pool (see scheme).

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