Angewandte Chemie International Edition

Cover image for Vol. 47 Issue 26

June 16, 2008

Volume 47, Issue 26

Pages 4761–4937

  1. Cover Picture

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    4. Graphical Abstract
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    7. Highlights
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    10. Communications
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    1. Cover Picture: PdII-Catalyzed Enantioselective Activation of C(sp2)[BOND]H and C(sp3)[BOND]H Bonds Using Monoprotected Amino Acids as Chiral Ligands (Angew. Chem. Int. Ed. 26/2008) (page 4761)

      Bing-Feng Shi, Nathan Maugel, Yang-Hui Zhang and Jin-Quan Yu

      Article first published online: 9 JUN 2008 | DOI: 10.1002/anie.200890122

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      Gearing between the α carbon atom and the nitrogen atom of an amino acid relays chiral information to the palladium(II) center, which cleaves C[BOND]H bonds asymmetrically. In their Communication on page 4882 ff., J.-Q. Yu et al. report on the palladium(II)-catalyzed enantioselective alkylation of sp2 and sp3 C[BOND]H bonds with boronic acids.

  2. Inside Cover

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    1. Inside Cover: Trends in the Catalytic CO Oxidation Activity of Nanoparticles (Angew. Chem. Int. Ed. 26/2008) (page 4762)

      Hanne Falsig, Britt Hvolbæk, Iben S. Kristensen, Tao Jiang, Thomas Bligaard, Claus H. Christensen and Jens K. Nørskov

      Article first published online: 9 JUN 2008 | DOI: 10.1002/anie.200890123

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      Gold at the pinnacle:In their Communication on page 4835 ff., J. Nørskov et al. use density functional calculations to show how gold nanoparticles are more active catalysts for the CO oxidation reaction than other metal nanoparticles. At low temperatures, high catalytic activity is due to the ability of low-coordinated metal atoms to activate reactants.

  3. Graphical Abstract

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  4. News

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  5. Book Review

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  6. Highlights

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    1. Pnictide Oxides: A New Class of High-TC Superconductors (pages 4782–4784)

      Dirk Johrendt and Rainer Pöttgen

      Article first published online: 19 MAY 2008 | DOI: 10.1002/anie.200801818

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      Competition for the cuprates: A new family of high-TC superconductors has been discovered. Iron pnictide oxides of the rare earth elements, such as LaFeAs(O1−xFx) (see crystal structure), are superconducting at temperatures up to 55 K and have critical magnetic fields up to 60 T. This result heralds a new era for superconductivity research, 22 years after the discovery of the cuprates.

    2. Synthesis of Marine Alkaloids from the Oroidin Family (pages 4785–4788)

      Hans-Dieter Arndt and Matthias Riedrich

      Article first published online: 2 JUN 2008 | DOI: 10.1002/anie.200801793

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      Oxidation with a difference: The complexity of the oroidin alkaloid family of marine natural products is generated biosynthetically from one simple alkene precursor, but has left the synthetic community with problems. The first total synthesis of the tetracyclic axinellamines (see structure) was recently completed. Key to the success was the chemoselective oxidative functionalization of imidazol(in)e rings (green).

  7. Minireview

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    1. Hydrogen Abstraction and Electron Transfer with Aminoxyl Radicals: Synthetic and Mechanistic Issues (pages 4790–4796)

      Carlo Galli, Patrizia Gentili and Osvaldo Lanzalunga

      Article first published online: 15 MAY 2008 | DOI: 10.1002/anie.200704292

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      A two-pronged attack: Aminoxyl radicals can react either by hydrogen atom transfer (HAT) or by electron-transfer (ET) mechanisms (see scheme). These different reaction pathways (mechanistic dichotomy) reflect a balance between the redox potential and the C[BOND]H bond energy of the substrate, but also depend on the reduction potential of the R2NO. species and the NO[BOND]H bond energy of the parent hydroxylamine.

  8. Review

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    1. Open-Framework Structures of Transition-Metal Compounds (pages 4798–4828)

      Srinivasan Natarajan and Sukhendu Mandal

      Article first published online: 7 MAY 2008 | DOI: 10.1002/anie.200701404

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      Putting the frame in the picture: The synthesis, structure, and important properties of open framework transition metal compounds of silicates, germanates, phosphates, phosphites, arsenates, borates as well as of analogous organic–inorganic hybrid structures are discussed. The various theoretical models employed for the description of magnetic behavior are also presented.

  9. Communications

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    1. Paclitaxel-Initiated, Controlled Polymerization of Lactide for the Formulation of Polymeric Nanoparticulate Delivery Vehicles (pages 4830–4834)

      Rong Tong and Jianjun Cheng

      Article first published online: 19 MAY 2008 | DOI: 10.1002/anie.200800491

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      Paclitaxel–polylactide nanoconjugates were prepared by the site-specific polymerization of lactide mediated by a paclitaxel–metal complex followed by nanoprecipitation (see scheme). The resulting nanoconjugates have nearly 100 % paclitaxel incorporation efficiencies and predefined drug loadings, and are less than 100 nm in diameter. The drug burst release effect is completely eliminated with this drug delivery vehicle.

    2. Trends in the Catalytic CO Oxidation Activity of Nanoparticles (pages 4835–4839)

      Hanne Falsig, Britt Hvolbæk, Iben S. Kristensen, Tao Jiang, Thomas Bligaard, Claus H. Christensen and Jens K. Nørskov

      Article first published online: 21 MAY 2008 | DOI: 10.1002/anie.200801479

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      Going for gold: Density functional calculations show how gold nanoparticles are more active catalysts for CO oxidation than other metal nanoparticles. The high catalytic activity of nanosized gold clusters at low temperature is found to be related to the ability of low-coordinate metal atoms to activate reactants.

    3. Effective Expansion of the Subporphyrin Chromophore Through Conjugation with meso-Oligo(1,4-phenyleneethynylene) Substituents: Octupolar Effect on Two-Photon Absorption (pages 4840–4843)

      Yasuhide Inokuma, Shanmugam Easwaramoorthi, So Young Jang, Kil Suk Kim, Dongho Kim and Atsuhiro Osuka

      Article first published online: 21 MAY 2008 | DOI: 10.1002/anie.200801192

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      Go with the glow: A series of meso-oligo(1,4-phenyleneethynylene) substituted subporphyrins shows a significant amplification in absorption coefficient and fluorescence quantum yield as the chain length of the substituents increases (see picture). Particularly, enhancement of the two-photon absorption properties along the series can be characterized by an octupolar effect rather than a conjugation effect.

    4. Reaction Dynamics of the Decaniobate Ion [HxNb10O28](6−x)− in Water (pages 4844–4846)

      Eric M. Villa, C. André Ohlin, Edina Balogh, Travis M. Anderson, May D. Nyman and William H. Casey

      Article first published online: 21 MAY 2008 | DOI: 10.1002/anie.200801125

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      The nanometer-size title cluster is unique in that it reacts slowly enough in water that one can simultaneously observe steady-state oxygen-isotope exchanges and dissociation pathways (see scheme; O red, Nb green), leading to conceptual advances in both geochemistry and polyoxometalate chemistry.

    5. Sweet Talking Double Hydrophilic Block Copolymer Vesicles (pages 4847–4850)

      George Pasparakis and Cameron Alexander

      Article first published online: 26 MAY 2008 | DOI: 10.1002/anie.200801098

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      How sweet it is: Double hydrophilic block copolymers containing glucose functionalities form vesicles in aqueous solutions with sugar groups on their surface. Small vesicles form large aggregates with glucose-binding lectins or cells, whereas larger vesicles form discrete complexes. The “language” of association between cells and vesicles was demonstrated, and information transfer was shown by dye transport from vesicle to cell through glycopolymer links.

      Corrected by:

      Corrigendum: Sweet Talking Double Hydrophilic Block Copolymer Vesicles

      Vol. 49, Issue 2, 241, Article first published online: 28 DEC 2009

    6. Palladium(0)-Catalyzed Alkynyl and Allenyl Iminium Ion Cyclizations Leading to 1,4-Disubstituted 1,2,3,6-Tetrahydropyridines (pages 4851–4854)

      Hirokazu Tsukamoto and Yoshinori Kondo

      Article first published online: 21 MAY 2008 | DOI: 10.1002/anie.200800823

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      The biologically important title heterocyclic compounds can be synthesized by two methods based on the cyclization of alkynyl and allenyl iminium ions generated in situ in the presence of organometallic reagents (see scheme). Symmetrical and unsymmetrical tetrahydropyridines with diverse substituents R4 were prepared in a single step under mild conditions. R1=n-, sec-, tert-alkyl; R4=aryl, 1-alkenyl, alkyl, 1-alkynyl, B(pinacolato).

    7. Plasmon-Resonance-Enhanced Absorption and Circular Dichroism (pages 4855–4857)

      Itai Lieberman, Gabriel Shemer, Tcipi Fried, Edward M. Kosower and Gil Markovich

      Article first published online: 21 MAY 2008 | DOI: 10.1002/anie.200800231

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      Colloidal Ag nanoparticles coated with L-glutathione attached to bimane chromophores were studied by absorption, circular dichroism (CD), and fluorescence spectroscopies. The absorption and CD spectra were resonantly enhanced by Ag surface plasmons. The wavelength and particle-size dependence of the enhancement indicated that an electromagnetic “antenna” effect is in action.

    8. A Metal-Mediated Conformational Switch Controls G-Quadruplex Binding Affinity (pages 4858–4861)

      David Monchaud, Peng Yang, Laurent Lacroix, Marie-Paule Teulade-Fichou and Jean-Louis Mergny

      Article first published online: 21 MAY 2008 | DOI: 10.1002/anie.200800468

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      Control by copper: CuII ions modulate the quadruplex affinity of the high-affinity ligand 360A and denaturate the folded quadruplex form of DNA 22AG to an unfolded form. So removal of copper through complexation enables the cycling of both 360A quadruplex affinity and quadruplex unfolding.

    9. Iron-Catalyzed Sonogashira Reactions (pages 4862–4865)

      Mónica Carril, Arkaitz Correa and Carsten Bolm

      Article first published online: 28 MAY 2008 | DOI: 10.1002/anie.200801539

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      With an iron will: Terminal alkynes undergo reaction with aryl and heteroaryl iodides in the presence of an iron catalyst formed from FeCl3 and N,N′-dimethylethylenediamine (dmeda, see scheme). The method displays a broad substrate scope and is economical, environmentally friendly, and experimentally simple. A “one-pot” Sonogashira/intramolecular hydroalkoxylation has also been achieved by this method.

    10. Nickel-Catalyzed Cross-Coupling of Aryl Methyl Ethers with Aryl Boronic Esters (pages 4866–4869)

      Mamoru Tobisu, Toshiaki Shimasaki and Naoto Chatani

      Article first published online: 21 MAY 2008 | DOI: 10.1002/anie.200801447

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      To C[BOND]OMe and go: The title reaction, involving cleavage of a C[BOND]OMe bond, is demonstrated for the coupling of aryl methyl ethers on fused aromatic systems, such as naphthalene and phenanthrene, as well as anisoles containing electron-withdrawing groups with a wide range of boronic esters. cod=cycloocta-1,5-diene, Cy=cyclohexyl.

    11. Efficient Helicene Synthesis: Friedel–Crafts-type Cyclization of 1,1-Difluoro-1-alkenes (pages 4870–4873)

      Junji Ichikawa, Misaki Yokota, Takao Kudo and Satoshi Umezaki

      Article first published online: 28 MAY 2008 | DOI: 10.1002/anie.200801396

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      The unique properties of fluorine substituents, leaving groups that also stabilize an α carbocation, are exploited in a high-yielding synthesis of substituted [4]- to [6]helicenes in three or four steps from commercially available compounds: Two fused benzene rings are constructed in the title reaction of readily prepared 1,1-difluoro-1-alkenes containing two aryl groups followed by dehydrogenation (see scheme).

    12. C-Type Cytochromes Wire Electricity-Producing Bacteria to Electrodes (pages 4874–4877)

      Juan P. Busalmen, Abraham Esteve-Núñez, Antonio Berná and Juan Miguel Feliu

      Article first published online: 26 MAY 2008 | DOI: 10.1002/anie.200801310

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      Down to the wire: electro-active bacteria that exchange electrons with solid electrodes are studied by electrochemical and infrared techniques. The approach allows the identification of cell-surface molecules involved in the direct electron transfer to the electrode, a development that is crucial for future utilization of these electricity-producing microorganisms.

    13. Palladium-Catalyzed Enantioselective Allylic Phosphination (pages 4878–4881)

      Pietro Butti, Raphaël Rochat, Aaron D. Sadow and Antonio Togni

      Article first published online: 21 MAY 2008 | DOI: 10.1002/anie.200801287

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      A new cat. for chiral phosphines: A highly enantioselective allylic phosphination reaction is realized using the Pd–Josiphos(L) catalyst system. This C[BOND]P bond forming reaction provides a new access to chiral phosphines (see scheme) that may be further functionalized. Cy=cyclohexyl, dba=trans,trans-dibenzylideneacetone.

    14. PdII-Catalyzed Enantioselective Activation of C(sp2)[BOND]H and C(sp3)[BOND]H Bonds Using Monoprotected Amino Acids as Chiral Ligands (pages 4882–4886)

      Bing-Feng Shi, Nathan Maugel, Yang-Hui Zhang and Jin-Quan Yu

      Article first published online: 16 MAY 2008 | DOI: 10.1002/anie.200801030

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      The relay of chiral information from the α-carbon atom of the amino acid ligand is believed to be crucial for chiral induction in the PdII-catalyzed enantioselective C[BOND]H activation/C[BOND]C coupling reaction of diphenyl(2-pyridyl)methane with boronic acids (see scheme; BQ=benzoquinone).

    15. Palladium Catalysts for the Formylation of Vinyl Triflates To Form α,β-Unsaturated Aldehydes (pages 4887–4891)

      Helfried Neumann, Alexey Sergeev and Matthias Beller

      Article first published online: 21 MAY 2008 | DOI: 10.1002/anie.200800994

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      What a gas! Synthesis gas is the formylating agent in the efficient one-step title transformation promoted by a palladium catalyst with the bidentate ligand 1,2-bis(di-1-adamantylphosphinomethyl)benzene (see scheme). This method enables the conversion of six- to eight-membered-ring triflates into α,β-unsaturated aldehydes and the introduction of a formyl group into derivatives of elaborate natural compounds. Tf=trifluoromethanesulfonyl.

    16. Regioselective Synthesis of γ-Amino Esters, Nitriles, Sulfones, and Pyrrolidinones by Nickel-Catalyzed Reductive Coupling of Aldimines and Activated Alkenes (pages 4892–4895)

      Chien-Hung Yeh, Rajendra Prasad Korivi and Chien-Hong Cheng

      Article first published online: 21 MAY 2008 | DOI: 10.1002/anie.200800825

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      A couple of alternatives: An efficient method has been developed for the synthesis of γ-amino derivatives and pyrrolidinones from readily available starting materials by using a nickel–phenanthroline complex (see scheme). The reaction proceeds by the formation of a C[BOND]C bond at the β-carbon atom, instead of the more usual α-carbon atom, of a conjugated alkene via an azanickelacycle intermediate.

    17. Sulfated Mesoporous Tantalum Oxides in the Shape Selective Synthesis of Linear Alkyl Benzene (pages 4896–4899)

      Junjie Kang, Yuxiang Rao, Michel Trudeau and David Antonelli

      Article first published online: 21 MAY 2008 | DOI: 10.1002/anie.200800721

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      Tantal(izing) catalysis: Mesoporous tantalum oxides were treated with 1.0 M sulfuric acid and evaluated for their catalytic activity and selectivity to 2-phenyl isomers in the alkylation of benzene with bulky olefins (see scheme). The sulfated mesoporous Ta oxide showed comparable activity to H-Y zeolite, but much higher 2-phenyldodecane selectivity in mild reaction conditions. The high activity and selectivity was rationalized by the eased diffusion of bulky reactants in the mesoporous frames.

    18. Template-Assembled Synthetic G-Quartets (TASQs) (pages 4900–4902)

      Mehran Nikan and John C. Sherman

      Article first published online: 21 MAY 2008 | DOI: 10.1002/anie.200704199

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      An unusual quartet: Four guanine residues have been efficiently “clicked” onto a cavitand to create a lipophilic template-assembled synthetic G-quartet (TASQ) structure in CDCl3. The TASQ manifests unusual cation-free structural integrity and stability. This cation-free basket, as well as corresponding potential cation-bound quartets and cation-induced quadruplexes may find applications in health therapies.

    19. Platinum(II)-Catalyzed Reaction of γ,δ-Ynones with Alkenes for the Construction of 8-Oxabicyclo[3.2.1]octane Skeletons: Generation of Platinum-Containing Carbonyl Ylides from Acyclic Precursors (pages 4903–4905)

      Hiroyuki Kusama, Kento Ishida, Hideaki Funami and Nobuharu Iwasawa

      Article first published online: 21 MAY 2008 | DOI: 10.1002/anie.200705129

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      Two types of bicycles can be prepared selectively by the title reaction, depending on whether or not a substituent is present at the propargylic position of the ynone substrate (see scheme). The cycloaddition of carbonyl ylides derived from γ,δ-ynones with vinyl ethers (or styrene) gave intermediate bicyclic carbene complexes, which underwent a 1,2-hydrogen-atom shift or rearrangement to provide the products. R1=alkyl, Ph; R3=alkyl.

    20. Synthesis of N-Fused Tricyclic Indoles by a Tandem [1,2] Stevens-Type Rearrangement/1,2-Alkyl Migration of Metal-Containing Ammonium Ylides (pages 4906–4909)

      Jun Takaya, Shuji Udagawa, Hiroyuki Kusama and Nobuharu Iwasawa

      Article first published online: 26 MAY 2008 | DOI: 10.1002/anie.200705517

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      An alkyne moiety is activated efficiently with a [W(CO)6] or [ReBr(CO)5] catalyst in the presence of an amine functionality in the title reaction of N-(2-alkynylphenyl)amines. The resulting ammonium ylides undergo rearrangement to form a variety of N-fused polycyclic indole derivatives (see scheme; n=1,2; R=alkyl, Ph).

    21. Scorpionate-Supported Dialkyl and Dihydride Lanthanide Complexes: Ligand- and Solvent-Dependent Cluster Hydride Formation (pages 4910–4913)

      Jianhua Cheng, Kuburat Saliu, Gong Y. Kiel, Michael J. Ferguson, Robert McDonald and Josef Takats

      Article first published online: 21 MAY 2008 | DOI: 10.1002/anie.200705977

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      Non-cyclopentadienyl lanthanide dihydrides [{(TpR,R′)LnH2}n] (R,R′=Me, n=4; R,R′=H, n=6) and [{(Tpmath image)YH2}3(thf)2–3] were isolated and characterized. Their polynuclear frameworks are maintained in solution, and their nuclearity depends on the ligand and the solvent used in their preparation. The structure of [{(Tpmath image)YH2}4] is shown (B red, H white, N blue, Y orange). TpR,R′=tris(3-R-5-R′-pyrazolyl)borate.

    22. Rhodium-Catalyzed Carbonylative [3+3+1] Cycloaddition of Biscyclopropanes with a Vinyl Substituent To Form Seven-Membered Rings (pages 4914–4917)

      Sun Young Kim, Sang Ick Lee, Soo Young Choi and Young Keun Chung

      Article first published online: 21 MAY 2008 | DOI: 10.1002/anie.200800432

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      Choose your catalyst wisely: Depending on the position of the cyclopropyl substituent on the bicyclo[4.1.0]hept-2-ene substrate, a different rhodium complex was used to catalyze the title reaction, which leads to bicyclic dienones in reasonable to excellent yields (see scheme). The products contain a highly substituted seven-membered ring with useful functionality for further manipulation. R1=H, Me; R2=H, Me, Ph; R3=Me, Et; X=NR, O.

    23. Monovalent and Bivalent Fibrin-specific MRI Contrast Agents for Detection of Thrombus (pages 4918–4921)

      Shrikumar A. Nair, Andrew F. Kolodziej, Gandhali Bhole, Matthew T. Greenfield, Thomas J. McMurry and Peter Caravan

      Article first published online: 21 MAY 2008 | DOI: 10.1002/anie.200800563

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      Probing in contrast: Four gadolinium-DTPA moieties (DTPA=diethylenetriaminepentaacetic acid) and two fibrin-specific cyclic peptides are linked by a compact triethylenetetraamine core (see scheme) to create a highly sensitive probe for molecular MR imaging of thrombosis. The contrast agent has a high molecular relaxivity, and the dual peptide construct provides five-fold higher fibrin affinity than the monovalent analogue. This bivalent probe showed significant specific thrombus uptake in an in vivo model of thrombosis.

    24. Silicon-Based Building Blocks for One-Step 18F-Radiolabeling of Peptides for PET Imaging (pages 4922–4925)

      Linjing Mu, Aileen Höhne, P. August Schubiger, Simon M. Ametamey, Keith Graham, John E. Cyr, Ludger Dinkelborg, Timo Stellfeld, Ananth Srinivasan, Ulrike Voigtmann and Ulrich Klar

      Article first published online: 21 MAY 2008 | DOI: 10.1002/anie.200705854

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      Radio-controlled landing of F: The facile 18F labeling of biomolecules has been achieved under mild conditions by using a unique silicon-based one-step approach (see scheme). A di-tert-butylsilyl derivative with an aryl linker was attached to a tetrapeptide. The assembly shows a hydrolytic stability that appears to be within the range required for in vivo positron emission tomography (PET) imaging applications.

    25. Helicity Inversion in Responsive Foldamers Induced by Achiral Halide ion Guests (pages 4926–4930)

      Robert M. Meudtner and Stefan Hecht

      Article first published online: 21 MAY 2008 | DOI: 10.1002/anie.200800796

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      A surprising about-face: Click chemistry was used for the efficient synthesis of a new class of foldamers, referred to as clickamers, that display unusual folding and recognition properties. In the presence of halide ions—achiral species—they undergo an unprecedented helix inversion.

    26. B+ in the Coordination Sphere of Two Transition Metals (pages 4931–4933)

      Holger Braunschweig, Katharina Kraft, Thomas Kupfer, Krzysztof Radacki and Fabian Seeler

      Article first published online: 21 MAY 2008 | DOI: 10.1002/anie.200800533

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      The first cationic metallaborylene complexes, [{(OC)5Mn}2(μ-B)][BArf4] and [{(η5-C5H4R)(OC)2Fe}2(μ-B)][BArf4] (R=H, Me; see structure) were synthesized by halide abstraction from bridged haloborylene complexes and structurally characterized. The boron atom is located in the coordination sphere of two transition-metal centers and is highly unsaturated.

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      Preview: Angew. Chem. Int. Ed. 27/2008 (page 4937)

      Article first published online: 9 JUN 2008 | DOI: 10.1002/anie.200890126

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