Angewandte Chemie International Edition

Cover image for Vol. 46 Issue 19

May 4, 2007

Volume 46, Issue 19

Pages 3381–3589

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Review
    9. Communications
    10. Preview
    1. Cover Picture: Direct Synthesis of Polymer Nanocapsules with a Noncovalently Tailorable Surface (Angew. Chem. Int. Ed. 19/2007) (page 3381)

      Dongwoo Kim, Eunju Kim, Jeeyeon Kim, Kyeng Min Park, Kangkyun Baek, Minseon Jung, Young Ho Ko, Wokyung Sung, Hyung Seok Kim, Ju Hyung Suh, Chan Gyung Park, Oh Sung Na, Dong-ki Lee, Kyung Eun Lee, Sung Sik Han and Kimoon Kim

      Version of Record online: 27 APR 2007 | DOI: 10.1002/anie.200790081

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      Polymer nanocapsules with a highly stable structure and relatively narrow size distribution were obtained without the use of any preorganized structure or template. In their Communication on page 3471 ff., K. Kim and co-workers report that photopolymerization of dithiols and allyloxycucurbit[6]uril spontaneously produces polymer nanocapsules as illustrated in the cover picture. The method appears to be applicable to any monomer with a flat core and multiple polymerizable groups at the periphery.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Review
    9. Communications
    10. Preview
    1. Inside Cover: [Al(Al3R3)2]: Prototype of a Metalloid Al Cluster or a Sandwich‒Stabilized Al Atom? (Angew. Chem. Int. Ed. 19/2007) (page 3382)

      Ping Yang, Ralf Köppe, Taike Duan, Jens Hartig, Gunar Hadiprono, Bernd Pilawa, Ilka Keilhauer and Hansgeorg Schnöckel

      Version of Record online: 27 APR 2007 | DOI: 10.1002/anie.200790082

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      Unique among metalloid clusters is the [Al7R6] structural element presented by H. Schnöckel and co-workers, which on the basis of the topology of its seven aluminum atoms is analogous to the metal and thus a molecular model for a single-atom contact. The Communication on page 3579 ff. reports that the oxidation and reduction of the neutral [Al7R6] cluster—like the removal and addition of an electron in conductance experiments—leads to drastic changes in the bond lengths within the {Al}7 framework and thus to different bonding properties.

  3. Graphical Abstract

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

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Review
    9. Communications
    10. Preview
    1. Carbon Nanotubes. Properties and Applications. Edited by Michael J. O'Connell. (page 3401)

      Stéphane Campidelli and Maurizio Prato

      Version of Record online: 27 APR 2007 | DOI: 10.1002/anie.200685446

  6. Highlights

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Review
    9. Communications
    10. Preview
    1. Palladium-Catalyzed Coupling of Ammonia and Hydroxide with Aryl Halides: The Direct Synthesis of Primary Anilines and Phenols (pages 3402–3404)

      Michael C. Willis

      Version of Record online: 12 MAR 2007 | DOI: 10.1002/anie.200605071

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      Back to basics: Ligand design has allowed two longstanding limitations of Pd-catalyzed C[BOND]N and C[BOND]O coupling reactions to be overcome. The use of specific sterically demanding electron-rich phosphine ligands makes it possible for ammonia and potassium hydroxide to act as coupling partners in palladium-catalyzed coupling with aryl halides.

    2. Synthetic Routes to N-Heterocyclic Carbene Complexes: Pyridine–Carbene Tautomerizations (pages 3405–3408)

      Doris Kunz

      Version of Record online: 3 APR 2007 | DOI: 10.1002/anie.200700192

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      70 years ago the existence of the 2-carbene isomer of pyridine, which arises by pyridine–carbene tautomerization (see scheme), was postulated. Now it has been prepared from pyridine as a stable carbene complex by metal-induced C[BOND]H activation. This pyridine–carbene tautomerization is described and discussed along with other analogous carbene tautomerization reactions.

  7. Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Review
    9. Communications
    10. Preview
    1. Catalytic Carbophilic Activation: Catalysis by Platinum and Gold π Acids (pages 3410–3449)

      Alois Fürstner and Paul W. Davies

      Version of Record online: 11 APR 2007 | DOI: 10.1002/anie.200604335

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      The reactivity of π-acidic metal catalysts has been correlated to known structural data. Through this comparison, the apparently disparate electrophilic metal carbene and nonclassical carbocation explanations (see picture), used in the literature to rationalize the diverse range of transformations possible under platinum and gold catalysis, come together under a reactivity profile through which this field may be rationalized.

  8. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Review
    9. Communications
    10. Preview
    1. Exciton Accumulation in π-Conjugated Wires Encapsulated by Light-Harvesting Macrocycles (pages 3450–3455)

      Klaus Becker, Pavlos G. Lagoudakis, Gerald Gaefke, Sigurd Höger and John M. Lupton

      Version of Record online: 19 APR 2007 | DOI: 10.1002/anie.200605072

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      Insulated wires: Light harvesting was demonstrated from a macrocyclic “tube” to covalently bound π-conjugated polymers encapsulated within (see picture). The multichromophoric polymer core allows accumulation of excitation energy. The high intramolecular mobility of these excitations leads to a dependence of the emission dynamics on chain length.

    2. Dehydration-Induced Conversion from a Single-Chain Magnet into a Metamagnet in a Homometallic Nanoporous Metal–Organic Framework (pages 3456–3459)

      Xian-Ming Zhang, Zheng-Ming Hao, Wei-Xiong Zhang and Xiao-Ming Chen

      Version of Record online: 27 MAR 2007 | DOI: 10.1002/anie.200604284

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      A change for the meta: On dehydration, a 3D homometallic porous organic–inorganic framework constructed from {Co3(OH)2} chains (see structure, pink Co, red O, blue N, gray C) undergoes a transition from being a single-chain magnet into a metamagnet. Apart from the loss of solvent water molecules, the dehydration leaves the framework structure largely unchanged.

    3. Environment-Sensitive Two-Photon Probe for Intracellular Free Magnesium Ions in Live Tissue (pages 3460–3463)

      Hwan Myung Kim, Cheol Jung, Bo Ra Kim, Soon-Young Jung, Jin Hee Hong, Young-Gyu Ko, Kyoung J. Lee and Bong Rae Cho

      Version of Record online: 2 APR 2007 | DOI: 10.1002/anie.200700169

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      “Green” emission: A novel two-photon fluorescent probe that can detect intracellular free Mg2+ ions at a depth of a few hundred micrometers in live tissue was developed. The emission from the Mg2+–probe complex (green) shows little interference from association of the probe with other intracellular metal ions or with the cell membrane (blue).

    4. One-Dimensional Porous Carbon/Platinum Composites for Nanoscale Electrodes (pages 3464–3467)

      Guanglei Cui, Linjie Zhi, Arne Thomas, Ute Kolb, Ingo Lieberwirth and Klaus Müllen

      Version of Record online: 30 MAR 2007 | DOI: 10.1002/anie.200700077

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      Current developments: The combination of a template method with electrochemical procedures has led to the controlled preparation of 1D nanoscale carbon/platinum electrodes with large surface areas and with small platinum nanoparticles homogeneously dispersed in the interconnected porous carbon matrix (see TEM images). The electrodes display excellent catalytic activities in the oxygen electroreduction.

    5. A Gold-Nanoparticle-Based Real-Time Colorimetric Screening Method for Endonuclease Activity and Inhibition (pages 3468–3470)

      Xiaoyang Xu, Min Su Han and Chad A. Mirkin

      Version of Record online: 27 MAR 2007 | DOI: 10.1002/anie.200605249

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      On the small screen: Aggregates of gold nanoparticles interconnected by DNA duplexes (see scheme, left) are bluish-purple. Cleavage of the duplexes by deoxyribonuclease I (DNase I) releases the nanoparticles (right), producing a bluish-purple-to-red color change. This color change can be used to monitor the activity (and inhibition) of the enzyme.

    6. Direct Synthesis of Polymer Nanocapsules with a Noncovalently Tailorable Surface (pages 3471–3474)

      Dongwoo Kim, Eunju Kim, Jeeyeon Kim, Kyeng Min Park, Kangkyun Baek, Minseon Jung, Young Ho Ko, Wokyung Sung, Hyung Seok Kim, Ju Hyung Suh, Chan Gyung Park, Oh Sung Na, Dong-ki Lee, Kyung Eun Lee, Sung Sik Han and Kimoon Kim

      Version of Record online: 15 JAN 2007 | DOI: 10.1002/anie.200604526

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      Hollow out your pumpkin: The direct synthesis of approximately 100-nm-diameter polymer nanocapsules was carried out in the absence of preorganized structures or templates. The method appears to be applicable to any monomer that has a flat core and multiple polymerizable groups at the periphery (see picture). The surface properties of the polymer shell, which comprises cucurbituril, can be easily tailored through host–guest chemistry.

    7. Cell-Penetrating-Peptide-Coated Nanoribbons for Intracellular Nanocarriers (pages 3475–3478)

      Yong-beom Lim, Eunji Lee and Myongsoo Lee

      Version of Record online: 27 MAR 2007 | DOI: 10.1002/anie.200604576

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      Wrap it up: Nanoribbons coated with cell-penetrating peptides (CPPs) allowed the encapsulation of hydrophobic guest molecules. The nanoassembly internalized into mammalian cells with high efficiency and showed selective intracellular compartmentalization owing to its sensitivity to the solution environment.

    8. Findings on the Electron-Attachment-Induced Abasic Site in a DNA Double Helix (pages 3479–3481)

      Jiande Gu, Jing Wang, Janusz Rak and Jerzy Leszczynski

      Version of Record online: 30 MAR 2007 | DOI: 10.1002/anie.200604603

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      One for the road: The potential-energy hyperface along the pathway of the formation of an abasic site (Pabasic) suggests that low-energy electrons (LEEs) might induce the formation of such a site at the 3′ end of a DNA double helix with the strand ended in a cytidine residue. Attachment of these LEEs to a DNA helix might significantly contribute to radiation-induced DNA damage. TS=transition state.

    9. Microfluidic Control of Fluorescence Resonance Energy Transfer: Breaking the FRET Limit (pages 3482–3485)

      Chun-yang Zhang and Lawrence W. Johnson

      Version of Record online: 27 MAR 2007 | DOI: 10.1002/anie.200604861

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      No empty FRET: The microfluidic control of fluorescence resonance energy transfer (FRET) has been demonstrated, and the FRET limit has been broken with a quantum-dot (QD)-based DNA nanosensor in a microfluidic flow. This nanosensor can detect long nucleic acids that have separation distances far beyond the range of FRET and whose detection is not feasible with conventional FRET-based assays.

    10. Redox Luminescence Switch Based on Energy Transfer in CePO4:Tb3+ Nanowires (pages 3486–3489)

      Qing Li and Vivian Wing-Wah Yam

      Version of Record online: 30 MAR 2007 | DOI: 10.1002/anie.200604973

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      On and off and on again: High-quality CePO4:Tb3+ nanowires were prepared easily in high yields at room temperature. The resulting 1D nanostructures exhibit Ce3+-sensitized terbium(III) luminescence (green). Oxidation of Ce3+ results in an absence of energy transfer (ET) from Ce4+ to Tb3+ and thus no green emission of the sample (see picture). The effect can be reversed by reduction, thus giving a reversible luminescent switch.

    11. A Large, Bowl-Shaped {Mo51V9} Polyoxometalate (pages 3490–3493)

      Sheng Wang, Xiang Lin, Ying Wan, Wenbin Yang, Shengmin Zhang, Canzhong Lu and Honghui Zhuang

      Version of Record online: 30 MAR 2007 | DOI: 10.1002/anie.200700076

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      Bowled over: A bowl-shaped {Mo51V9} polyoxometalate anion (see picture) is produced in a hydrothermal synthesis by a redox self-assembly process. This new compound has different building blocks and linkages to previously reported polyoxometalates (see structure; N green, O red, Mo/V gray, threefold axis indicated by black triangle).

      Corrected by:

      Corrigendum: A Large, Bowl-Shaped {Mo51V9} Polyoxometalate

      Vol. 46, Issue 30, 5647, Version of Record online: 13 JUL 2007

    12. Synthesis and Ligand-Exchange Kinetics of the Solvated Trigonal-Prismatic Clusters [W6CCl12L6]2+ (L=dmf, py) (pages 3494–3496)

      Eric J. Welch and Jeffrey R. Long

      Version of Record online: 27 MAR 2007 | DOI: 10.1002/anie.200700151

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      Trading places: The first terminal-ligand substitution reactions on the trigonal-prismatic cluster [W6CCl18]2− are reported. The new cluster [W6CCl12(SO3CF3)6]2− is a convenient precursor for solvated [W6CCl12]2+ cluster cores. Self-exchange kinetics experiments on a pyridine-substituted variant (see picture; black W, green Cl, blue N, dark gray C) reveal that the core is classified as inert.

    13. A Supramolecular Ferroelectric Realized by Collective Proton Transfer (pages 3497–3501)

      Sachio Horiuchi, Reiji Kumai and Yoshinori Tokura

      Version of Record online: 30 MAR 2007 | DOI: 10.1002/anie.200700407

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      Cooperative crystals: In ferroelectric cocrystals of iodanilic acid (see picture, orange) and 5,5′-dimethyl-2,2′-bipyridine (green), the molecules are linked into polar chains by O[BOND]H⋅⋅⋅N and N+[BOND]H⋅⋅⋅O hydrogen bonds. The application of a small electric field (E) effects a cooperative proton transfer across the hydrogen bonds, which is accompanied by a reversal of the polarity (P).

    14. Deoxyribozyme-Catalyzed Labeling of RNA (pages 3502–3504)

      Dana A. Baum and Scott K. Silverman

      Version of Record online: 30 MAR 2007 | DOI: 10.1002/anie.200700357

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      Tag team: A deoxyribozyme is used in a general strategy for site-specific covalent modification of RNA. This strategy was used to append the fluorescence resonant energy transfer (FRET) pair, fluorescein and tetramethylrhodamine (tamra), to the 160-nucleotide P4–P6 RNA, thereby enabling a FRET experiment to be performed for this RNA.

    15. Fluorescent Epibatidine Agonists for Neuronal and Muscle-Type Nicotinic Acetylcholine Receptors (pages 3505–3508)

      Jörg Grandl, Elias Sakr, Florence Kotzyba-Hibert, Florian Krieger, Sonia Bertrand, Daniel Bertrand, Horst Vogel, Maurice Goeldner and Ruud Hovius

      Version of Record online: 27 MAR 2007 | DOI: 10.1002/anie.200604807

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      Singled out: Specific high-affinity binding to and activation of nicotinic acetylcholine receptors (nAChRs) by fluorescent epibatidine (EPB) agonists is detected by fluorescence microscopy and electrophysiology (see picture). The optical and pharmacological properties of these compounds allow single-channel/single-molecule experiments at the surface of living cells, and investigation of channel gating and receptor trafficking.

    16. Rearrangement of a Pd4 Skeleton from a 1D Chain to a 2D Sheet on the Face of a Perylene or Fluoranthene Ligand Caused by Exchange of the Binder Molecule (pages 3509–3512)

      Tetsuro Murahashi, Naohiro Kato, Tomohito Uemura and Hideo Kurosawa

      Version of Record online: 3 APR 2007 | DOI: 10.1002/anie.200700340

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      Changing places: A chain-to-sheet rearrangement of the Pd4 moiety (see picture; spheres: Pd, support: organic ligand) takes place during the exchange of one perylene or fluoranthene ligand of a bis(perylene) or a bis(fluoranthene) tetrapalladium sandwich complex by 1,3,5,7-cyclooctatetraene. These findings are established by X-ray crystallography and NMR spectroscopy.

    17. AlCl3-Mediated Mono-, Di-, and Trihydroarylation of [60]Fullerene (pages 3513–3516)

      Akihiko Iwashita, Yutaka Matsuo and Eiichi Nakamura

      Version of Record online: 27 MAR 2007 | DOI: 10.1002/anie.200700062

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      Functionalization of fullerenes can be achieved inexpensively by Friedel–Crafts reaction. For instance, treatment of [60]fullerene with AlCl3 in toluene gave mono-, di-, and tritolyltrihydro[60]fullerenes in moderate to good yields (see scheme). The structures of the products were determined by crystallography and derivatization.

    18. Spectroscopy and High-Resolution Microscopy of Single Nanocrystals by a Focused Ion Beam Registration Method (pages 3517–3520)

      Carolina Novo, Alison M. Funston, Isabel Pastoriza-Santos, Luis M. Liz-Marzán and Paul Mulvaney

      Version of Record online: 30 MAR 2007 | DOI: 10.1002/anie.200700033

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      Telling FIBs: Identification of the exact size and shape of a nanoparticle is crucial for direct comparison of experimental results with theoretical predictions. A focused ion beam (FIB) registration method enables routine spectroscopic and high-resolution microscopic experiments to be carried out on the same nanoparticle (see picture).

    19. Tuning Electron Transfer through Translational Motion in Molecular Shuttles (pages 3521–3525)

      Aurelio Mateo-Alonso, Christian Ehli, G. M. Aminur Rahman, Dirk M. Guldi, Giulia Fioravanti, Massimo Marcaccio, Francesco Paolucci and Maurizio Prato

      Version of Record online: 30 MAR 2007 | DOI: 10.1002/anie.200605039

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      Shuttling rules! A bistable fullerene-stoppered molecular shuttle equipped with two ferrocene electron donors on the macrocycle has been prepared. A controlled positional change of the ferrocene groups along the thread results in different spatial arrangements of the electroactive units and allows the kinetics of the electron transfer and the lifetime of the charged-separated state to be modulated/fine-tuned (see picture).

    20. Total Synthesis of Tubulysins U and V (pages 3526–3529)

      Monica Sani, Giacomo Fossati, Florent Huguenot and Matteo Zanda

      Version of Record online: 2 APR 2007 | DOI: 10.1002/anie.200604557

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      Meeting the challenge: A reliable and modular reaction sequence has been developed for the synthesis of the challenging tubulysin framework. This route allows preparation of hundreds of milligrams of the stereochemically pure tetrapeptides (see picture), which are produced in small amounts by two different species of myxobacteria. Thus, full biological evaluation of the tubulysins and their analogues is now a real possibility.

    21. Enhanced Activity for Electrocatalytic Oxidation of Carbon Monoxide on Titania-Supported Gold Nanoparticles (pages 3530–3532)

      Brian E. Hayden, Derek Pletcher and Jens-Peter Suchsland

      Version of Record online: 23 MAR 2007 | DOI: 10.1002/anie.200604633

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      Support makes the difference: Investigation of particle-size- and substrate-dependent activity for the electrochemical oxidation of CO provides an opportunity to consider the origin of the unique activity of supported Au nanoparticles in a new light. Furthermore, manipulation of catalytic activity by particle size and support provides an important tool for the future optimization of electrocatalysts.

    22. Structural, Magnetic, and Theoretical Characterization of a Heterometallic Polypyridylamide Complex (pages 3533–3536)

      Marie-Madeleine Rohmer, Isiah Po-Chun Liu, Jheng-Cheng Lin, Mei-Jyun Chiu, Chia-Hwa Lee, Gene-Hsiang Lee, Marc Bénard, Xavier López and Shie-Ming Peng

      Version of Record online: 27 MAR 2007 | DOI: 10.1002/anie.200604313

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      A heterometallic backbone has been obtained for the first time in a trinuclear complex of bis(2-pyridyl)amide (dpa), namely, [Co2PdCl2(dpa)4] (1). The crystal structure (depicted), magnetic measurements, and DFT calculations suggest that its ground state results from coupling of two high-spin CoII ions separated by a magnetically inactive Pd center. Hence, the magnetic behavior of CoII in 1 strongly differs from that in its tricobalt homologue.

    23. Fast Electrochemically Induced Translation of the Ring in a Copper-Complexed [2]Rotaxane: The Biisoquinoline Effect (pages 3537–3540)

      Fabien Durola and Jean-Pierre Sauvage

      Version of Record online: 30 MAR 2007 | DOI: 10.1002/anie.200604815

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      On the fast track: A molecular shuttle has been synthesized, whose ring incorporates an 8,8′-diphenyl-3,3′-biisoquinoline chelating unit. This unit is both endocyclic and not sterically hindering (see picture), which leads to remarkably fast shuttling motions (milliseconds) of the copper-complexed ring between two stations.

    24. High-Yield Synthesis of Medium and Large Platinacycloalkanes from Bis(alkenyl) Precursors (pages 3541–3543)

      Akella Sivaramakrishna, Hong Su and John R. Moss

      Version of Record online: 30 MAR 2007 | DOI: 10.1002/anie.200604979

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      Coming full circle: Bis(alkenyl)platinum(II) complexes cis-[L2Pt{(CH2)nCH[DOUBLE BOND]CH2}2] (L=PPh3 or L2=Ph2P(CH2)3PPh2; n=3–6) have been prepared and fully characterized. Ring-closing metathesis leads to new platinacycloalkenes, which can be hydrogenated to platinacycloalkanes with 9-, 11-, 13-, and 15-membered rings (see picture for 15-membered ring; Pt green, P orange, C blue, H white).

    25. Strong Two-Photon Absorption of Singlet Diradical Hydrocarbons (pages 3544–3546)

      Kenji Kamada, Koji Ohta, Takashi Kubo, Akihiro Shimizu, Yasushi Morita, Kazuhiro Nakasuji, Ryohei Kishi, Suguru Ohta, Shin-ichi Furukawa, Hideaki Takahashi and Masayoshi Nakano

      Version of Record online: 27 MAR 2007 | DOI: 10.1002/anie.200605061

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      Ones and twos: The two-photon absorption cross sections (σ(2)) of singlet diradical hydrocarbons with phenalenyl peripheral groups (see scheme) are larger than those of closed-shell aromatic hydrocarbons by an order of magnitude or more and are comparable to those of π-conjugated compounds with strong electron donor or acceptor substituents. A significant increase in cross section was also observed in the resonance-enhanced region.

    26. A Practical Solid-Phase Synthesis of Glu7-Phalloidin and Entry into Fluorescent F-Actin-Binding Reagents (pages 3547–3549)

      Laura A. Schuresko and R. Scott Lokey

      Version of Record online: 27 MAR 2007 | DOI: 10.1002/anie.200700017

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      Simple synthesis of a potent probe: An efficient solid-phase synthesis of Glu7-phalloidin (the resin-bound cyclic peptide shown) features the one-pot I2-mediated deprotection of S-tritylcysteine and formation of the Cys–Trp thioether bridge. A fluorescent conjugate of the resulting phalloidin analogue shows specific staining of F-actin (filamentous actin) in fixed mammalian epithelial cells (see fluorescence micrograph). Fmoc=9-fluorenylmethoxycarbonyl.

    27. Anodic Fluorination Based on Cation Exchange between Alkali-Metal Fluorides and Solid-Supported Acids (pages 3550–3552)

      Toshiki Tajima, Atsushi Nakajima, Yuta Doi and Toshio Fuchigami

      Version of Record online: 30 MAR 2007 | DOI: 10.1002/anie.200700037

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      Positively shocking: The interchange of cations between alkali-metal fluorides and solid-supported acids (see picture) in an electrolytic system promotes the anodic fluorination of organic compounds to give the corresponding fluorinated products in good to excellent yields.

    28. Direct EPR Detection of a Hydrogen-Bonded Complex between a Semiquinone Radical Anion and a Protonated Amino Acid, and Electron Transfer Driven by Hydrogen Bonding (pages 3553–3555)

      Junpei Yuasa, Shunsuke Yamada and Shunichi Fukuzumi

      Version of Record online: 30 MAR 2007 | DOI: 10.1002/anie.200700157

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      Strong hydrogen bonding in a complex of a semiquinone radical anion and protonated histidine (His⋅2 H+), detected for the first time by EPR spectroscopy during photoinduced electron transfer from 10,10′-dimethyl-9,9′-biacridine (D) to 1-(p-tolylsulfinyl)-2,5-benzoquinone in the presence of His⋅2 H+ (picture, top), was revealed by the presence in the EPR spectrum (picture, bottom) of superhyperfine splitting caused by the NH3+ group.

    29. Hiyama Reactions of Activated and Unactivated Secondary Alkyl Halides Catalyzed by a Nickel/Norephedrine Complex (pages 3556–3558)

      Neil A. Strotman, Stefan Sommer and Gregory C. Fu

      Version of Record online: 19 APR 2007 | DOI: 10.1002/anie.200700440

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      An active partner: Nickel in combination with an amino alcohol ligand (norephedrine) was found to provide the most versatile and efficient catalyst for Hiyama cross-coupling reactions of alkyl electrophiles that has been described to date. Unprecedented Hiyama reactions of activated secondary alkyl bromides were achieved, as were the first Hiyama couplings of (activated) alkyl chlorides (see scheme, X=Br, Cl; HMDS=1,1,1,3,3,3-hexamethyldisilazane, DMA=N,N-dimethylacetamide).

    30. The Amphiphilic Properties of Spider Silks Are Important for Spinning (pages 3559–3562)

      Josef H. Exler, Daniel Hümmerich and Thomas Scheibel

      Version of Record online: 2 APR 2007 | DOI: 10.1002/anie.200604718

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      Along came a spider… Spider silk is a fascinating biomaterial owing to its strength, extensibility, and toughness per unit weight which is unrivaled by man-made fibers. The spinning of spider silk corresponds to a transition from a liquid phase to a solid thread. The underlying mechanism of this transition has been investigated using a recombinantly produced spider silk protein.

    31. Nucleophilicity Parameters for Alkyl and Aryl Isocyanides (pages 3563–3566)

      Vasily V. Tumanov, Alexander A. Tishkov and Herbert Mayr

      Version of Record online: 30 MAR 2007 | DOI: 10.1002/anie.200605205

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      How nucleophilic are isocyanides? The kinetics of the reactions of alkyl and aryl isocyanides with benzhydrylium ions indicate that isocyanides are 10 orders of magnitude less reactive than the cyanide ion and their nucleophilic reactivity is comparable to that of allylsilanes and silyl enol ethers (see the diagram for a comparison of the nucleophilicity N of various isocyanides; Ts=toluene-4-sulfonyl).

    32. Metalloenzyme-Inspired Catalysis: Selective Oxidation of Primary Alcohols with an Iridium–Aminyl-Radical Complex (pages 3567–3570)

      Martin Königsmann, Nicola Donati, Daniel Stein, Hartmut Schönberg, Jeffrey Harmer, Anandaram Sreekanth and Hansjörg Grützmacher

      Version of Record online: 30 MAR 2007 | DOI: 10.1002/anie.200605170

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      A little goes a long way: An iridium–nitrogen-radical complex is a highly active and selective catalyst for the dehydrogenation (oxidation) of primary alcohols to aldehydes in the presence of the oxidant benzoquinone (see simplified scheme). With only 0.01 mol % of the complex, turnover frequencies of up to 150 000 s−1 are reached.

    33. Probing Integrin Selectivity: Rational Design of Highly Active and Selective Ligands for the α5β1 and αvβ3 Integrin Receptor (pages 3571–3574)

      Dominik Heckmann, Axel Meyer, Luciana Marinelli, Grit Zahn, Roland Stragies and Horst Kessler

      Version of Record online: 30 MAR 2007 | DOI: 10.1002/anie.200700008

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      Try and fit in: A strategy for the rational design of α5β1 ligands for the purpose of lead generation and biochemical studies on integrin selectivity is based α5β1 homology modeling. Ligand 1 can bind α5β1 with activities in the subnanomolar range and high selectivity. Minor changes can result in a ligand with a high selectivity for the related αvβ3 receptor.

    34. How Reliable Are Current Docking Approaches for Structure-Based Drug Design? Lessons from Aldose Reductase (pages 3575–3578)

      Matthias Zentgraf, Holger Steuber, Cornelia Koch, Concettina La Motta, Stefania Sartini, Christoph A. Sotriffer and Gerhard Klebe

      Version of Record online: 30 MAR 2007 | DOI: 10.1002/anie.200603625

      Thumbnail image of graphical abstract

      Two related inhibitors were flexibly docked into different conformers of aldose reductase. Although the overall binding topologies were roughly matched, significant deviations are observed in the subsequently determined crystal structures. Flexible redocking into the crystallographically observed protein conformers achieves, however, perfect binding-position predictions.

    35. [Al(Al3R3)2]: Prototype of a Metalloid Al Cluster or a Sandwich‒Stabilized Al Atom? (pages 3579–3583)

      Ping Yang, Ralf Köppe, Taike Duan, Jens Hartig, Gunar Hadiprono, Bernd Pilawa, Ilka Keilhauer and Hansgeorg Schnöckel

      Version of Record online: 17 APR 2007 | DOI: 10.1002/anie.200604567

      Thumbnail image of graphical abstract

      Big Al: Nanometer-separated, perfectly arranged p1 spin systems are found in crystals of molecular [Al(Al3R3)2] radicals (R=N(SiMe2Ph)2; see spin-density diagram of the model compound [Al(AlNH2)6]). [Al(Al3R3)2] is surprisingly stable in the solid state. The unique topology of the seven metal atoms in the [Al(Al3R3)] molecules is discussed: Do these atoms represent a section of the bulk structure of Al and can thus be described as the simplest metalloid cluster?

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