Angewandte Chemie International Edition

Cover image for Vol. 49 Issue 20

May 3, 2010

Volume 49, Issue 20

Pages 3391–3543

  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. Minireview
    10. Review
    11. Communications
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    1. Cover Picture: Rhodamines NN: A Novel Class of Caged Fluorescent Dyes (Angew. Chem. Int. Ed. 20/2010) (page 3391)

      Vladimir N. Belov, Christian A. Wurm, Vadim P. Boyarskiy, Stefan Jakobs and Stefan W. Hell

      Article first published online: 7 APR 2010 | DOI: 10.1002/anie.201001497

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      The photoactivatable fluorescent dye … … rhodamine NN, whose structure is shown in the cover picture, was combined with two further caged fluorophores with similar spectroscopic properties in a microscopy scheme for imaging cellular structures such as peroxysomes, actin, and microtubuli. The scheme, which uses only one emission and one detection channel, enables the stepwise activation and detection of the dyes. The synthesis and properties of rhodamine NN are described in the Communication by V. N. Belov et al. on page 3520 ff. (Picture: H. Sebesse, MPI für biophysikalische Chemie, Göttingen).

  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. Minireview
    10. Review
    11. Communications
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    1. Inside Cover: Bright Three-Photon Luminescence from Gold/Silver Alloyed Nanostructures for Bioimaging with Negligible Photothermal Toxicity (Angew. Chem. Int. Ed. 20/2010) (page 3392)

      Ling Tong, Claire M. Cobley, Jingyi Chen, Younan Xia and Ji-Xin Cheng

      Article first published online: 1 APR 2010 | DOI: 10.1002/anie.201001647

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      Au/Ag alloyed nanostructures exhibit a bright three-photon luminescence upon excitation by a femtosecond laser, and have an intensity level one order of magnitude higher than pure Au or Ag nanoparticles. As Y. Xia, J.-X. Cheng, and co-workers describe in their Communication on page 3485 ff., the excitation is outside the range of plasmon resonance, thus enabling bioimaging with negligible photothermal toxicity.

  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. Minireview
    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. Minireview
    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. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Takeshi Akasaka (page 3408)

      Article first published online: 13 APR 2010 | DOI: 10.1002/anie.201000967

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      “My most exciting discovery to date has been the functionalization of endohedral metallofullerenes. My biggest motivation is to realize that where there is a will, there is a way …” This and more about Takeshi Akasaka can be found on page 3408.

  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. Minireview
    10. Review
    11. Communications
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    1. Concepts of Nanochemistry. By Ludovico Cademartiri and Geoffrey A. Ozin. (pages 3409–3410)

      Nikolaus Korber

      Article first published online: 28 APR 2010 | DOI: 10.1002/anie.201000743

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      Wiley-VCH, Weinheim 2009. 262 pp., softcover € 39.00.—ISBN 978-3527325979

    2. Click Chemistry for Biotechnology and Materials Science. Edited by Joerg Lahann. (pages 3410–3411)

      Richard Hoogenboom

      Article first published online: 28 APR 2010 | DOI: 10.1002/anie.201001068

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      John Wiley & Sons, Hoboken 2009. 432 pp., hardcover € 125.00.—ISBN 978-0470699706

  7. Highlights

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. News
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    7. Book Reviews
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
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    1. Borylene Complexes

      Fashionably Late: Synthesis and Characterization of Transition-Metal–Fluoroborylene Complexes (pages 3412–3414)

      Holger Braunschweig and Rian D. Dewhurst

      Article first published online: 9 APR 2010 | DOI: 10.1002/anie.201000841

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      B and F become BFFs: The last of the neutral first-row main group diatomics, BF, has conspicuously eluded synthetic chemists and their attempts to stabilize it by transition metals. After decades of near misses, two contrasting families of fluoroborylene transition metal complexes have been definitively synthesized by the research groups of Aldridge and Andrews.

    2. Synthetic Methods

      Thiol–Yne Chemistry: A Powerful Tool for Creating Highly Functional Materials (pages 3415–3417)

      Richard Hoogenboom

      Article first published online: 14 APR 2010 | DOI: 10.1002/anie.201000401

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      Branching out: Thiol–yne chemistry is emerging as new tool for polymer chemists, as it represents a unique and efficient coupling procedure to create highly branched structures (see scheme). This method can be used to prepare highly functional dendrimers and hyperbranched polymers.

  8. Minireview

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

      Cyclopamine and Hedgehog Signaling: Chemistry, Biology, Medical Perspectives (pages 3418–3427)

      Philipp Heretsch, Lito Tzagkaroulaki and Athanassios Giannis

      Article first published online: 6 APR 2010 | DOI: 10.1002/anie.200906967

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      The freaky molecule: From Odysseus' encounter with the cyclops and the appearance of cyclops-like sheep in Idaho more than 3000 years later, to the discovery of cyclopamine and the hedgehog signaling pathway as well as a highly selective anticancer therapy—this sometimes creepy but always interesting story is told in this Minireview.

  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. Minireview
    10. Review
    11. Communications
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    1. Nanocatalysts

      Magnetically Separable Nanocatalysts: Bridges between Homogeneous and Heterogeneous Catalysis (pages 3428–3459)

      Sankaranarayanapillai Shylesh, Volker Schünemann and Werner R. Thiel

      Article first published online: 23 APR 2010 | DOI: 10.1002/anie.200905684

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      An attractive concept: Quasihomogeneous magnetic nanoparticles and magnetic nanocomposites have found increasing application in organic synthesis; for example, they are ideal supports for the heterogenization of homogeneous catalysts (the picture shows a catalyst that can be removed with a simple magnet). This Review summarizes recent developments in the synthesis, characterization, and applications of these materials.

  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. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Cell Mass Spectrometry

      Quantitative Measurement of Nano-/Microparticle Endocytosis by Cell Mass Spectrometry (pages 3460–3464)

      Huan-Chang Lin, Hsin-Hung Lin, Cai-Yu Kao, Alice L. Yu, Wen-Ping Peng and Chung-Hsuan Chen

      Article first published online: 13 APR 2010 | DOI: 10.1002/anie.201000891

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      All present and accounted for? Cell mass spectrometry was used to determine the quantity of both gold and polystyrene nano-/microparticles taken up into cells (see picture). The uptake amounts measured for gold nanoparticles were similar to those determined by inductively coupled plasma mass spectrometry, a technique which can not be used to measure the cellular uptake of nonmetal particles.

    2. CO2 Binding

      An Isolated CO2 Adduct of a Nitrogen Base: Crystal and Electronic Structures (pages 3465–3468)

      Claude Villiers, Jean-Pierre Dognon, Rodolphe Pollet, Pierre Thuéry and Michel Ephritikhine

      Article first published online: 31 MAR 2010 | DOI: 10.1002/anie.201001035

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      In a crystal at last: CO2 binds reversibly to the guanidine molecule TBD. The zwitterionic structure of the adduct is demonstrated by X-ray diffraction analysis and computational methods (see picture; left: C blue, H white, N pink, O red), while its fluxionality in solution is revealed by NMR spectroscopy.

    3. Protein Folding

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      Alteration of the α-Synuclein Folding Landscape by a Mutation Related to Parkinson’s Disease (pages 3469–3472)

      Allan Chris M. Ferreon, Crystal R. Moran, Josephine C. Ferreon and Ashok A. Deniz

      Article first published online: 6 APR 2010 | DOI: 10.1002/anie.201000378

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      Shape shifting linked to disease: A single-molecule fluorescence technique was used to probe structures of an intrinsically disordered brain protein. A mutation was found to tilt the coupled binding–folding energy landscape of the protein and inhibited switching between induced ordered structures (see picture). The observations provide fundamental insight into the molecular basis of Parkinson's disease.

    4. Combinatorial Chemistry

      Microparticle Matrix Encoding of Beads (pages 3473–3476)

      Morten Meldal and Søren Flygering Christensen

      Article first published online: 8 APR 2010 | DOI: 10.1002/anie.200906563

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      Reloaded matrix: Facile optical encoding of polyethylene glycol (PEG) based resins provides a direct identification of compounds in combinatorial libraries, and the structures may be correlated with bioactivity. The new technique, microparticle matrix (MPM) encoding (see picture), circumvents some problems often encountered in solid-phase combinatorial chemistry and is extremely simple to implement.

    5. Protein Purification

      Small-Molecule Affinity Ligands for Protein Purification: Combined Computational Enrichment and Automated In-line Screening of an Optically Encoded Library (pages 3477–3480)

      Jakob E. Rasmussen, Christine B. Schiødt, Søren F. Christensen, Leif Nørskov-Lauritsen, Morten Meldal, Phaedria M. St. Hilaire and Knud J. Jensen

      Article first published online: 18 MAR 2010 | DOI: 10.1002/anie.200906602

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      Screening with codes: A versatile methodology for the development of small-molecule affinity chromatography ligands for protein targets is presented. The combination of computational enrichment with automated screening and affinity mapping of an optically encoded combinatorial library allows identification of a novel set of ligands for the single-step purification of human growth hormone (see picture).

    6. NMR Techniques

      Nuclear Magnetic Resonance Using a Spatial Frequency Encoding: Application to J-Edited Spectroscopy along the Sample (pages 3481–3484)

      Nicolas Giraud, Laetitia Béguin, Jacques Courtieu and Denis Merlet

      Article first published online: 13 APR 2010 | DOI: 10.1002/anie.200907103

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      Finger on the pulse: Selective experiments can be simultaneously run on different parts of the sample when NMR sequences based on a spatial encoding are used. This approach was applied to a gradient-encoded selective refocusing sequence. The resulting data provide a collection of all the couplings that involve a given proton spin, which can be conveniently assigned and measured from only one spectrum.

    7. Imaging Agents

      Bright Three-Photon Luminescence from Gold/Silver Alloyed Nanostructures for Bioimaging with Negligible Photothermal Toxicity (pages 3485–3488)

      Ling Tong, Claire M. Cobley, Jingyi Chen, Younan Xia and Ji-Xin Cheng

      Article first published online: 6 APR 2010 | DOI: 10.1002/anie.201000440

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      Au/Ag alloyed nanostructures exhibit a bright three-photon luminescence (3PL; see picture, left) upon excitation by a femtosecond laser at 1290 nm, with an intensity level one order of magnitude higher than pure Au or Ag nanoparticles. As the excitation is outside the range of plasmon resonance, 3PL enables bioimaging (right) with negligible photothermal toxicity.

    8. Phosphorus-Containing Polymers

      High-Molecular-Weight Poly(vinylphosphonate)s by Single-Component Living Polymerization Initiated by Rare-Earth-Metal Complexes (pages 3489–3491)

      Uwe B. Seemann, Joachim E. Dengler and Bernhard Rieger

      Article first published online: 8 APR 2010 | DOI: 10.1002/anie.201000804

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      Transfer ticket: A group transfer polymerization (GTP) reaction mechanism operates in the living polymerization of diethyl vinylphosphonate, in which high-molecular-weight homo- and copolymers are produced using simple rare-earth-metal complexes (see scheme). The mechanism is consistent with the well-known and established mechanism for polar monomers such as acrylates, and opens up a new approach toward phosphorus-containing polymeric materials.

    9. Nanorod Arrays

      Cerium Vanadate Nanorod Arrays from Ionic Chelator-Mediated Self-Assembly (pages 3492–3495)

      Junfeng Liu, Linlin Wang, Xiaoming Sun and Xingqi Zhu

      Article first published online: 6 APR 2010 | DOI: 10.1002/anie.201000783

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      Line them up: Uniform CeVO4 nanorod arrays (see picture) were synthesized in a self-assembly approach assisted by ethylenediaminetetraacetic acid (EDTA) molecules in aqueous media. EDTA is important not only in controlling anisotropic growth by restricting the active points of certain faces, but also in mediating the assembly by forming intermolecular hydrogen bonds.

    10. Cycloaddition Reactions

      Metallacyclic Pyridylidene Structures from Reactions of Terminal Pyridylidenes with Alkenes and Acetylene (pages 3496–3499)

      Eleuterio Álvarez, Yohar A. Hernández, Joaquín López-Serrano, Celia Maya, Margarita Paneque, Ana Petronilho, Manuel L. Poveda, Verónica Salazar, Florencia Vattier and Ernesto Carmona

      Article first published online: 1 APR 2010 | DOI: 10.1002/anie.201000608

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      Iridium pyridyl species are key intermediates in the title reactions. Thermal elimination of benzene from complexes 1 (R=Me, Ph) creates a vacant coordination site accessible to unsaturated hydrocarbons. Subsequent intramolecular nucleophilic attack by the pyridyl nitrogen atom to the alkene or vinylidene leads to iridacyclic pyridylidene structures (see scheme).

    11. Polymers

      One-Pot Synthesis of Biomimetic Shell Cross-Linked Micelles and Nanocages by ATRP in Alcohol/Water Mixtures (pages 3500–3503)

      Shinji Sugihara, Steven P. Armes and Andrew L. Lewis

      Article first published online: 7 APR 2010 | DOI: 10.1002/anie.201000095

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      Shell shock: The one-pot synthesis of shell cross-linked (SCL) micelles was achieved using an ABC triblock copolymer in a 9:1 alcohol/water mixture. These SCL micelles were dialyzed against water, leading to solvation of the core-forming PMPC chains. If the cross-linking is not too high, these chains migrate through the inner shell to join the coronal PEO chains, hence forming nanocages.

    12. Hybrid Materials

      Substrate Size-Selective Catalysis with Zeolite-Encapsulated Gold Nanoparticles (pages 3504–3507)

      Anders B. Laursen, Karen T. Højholt, Lars F. Lundegaard, Søren B. Simonsen, Stig Helveg, Ferdi Schüth, Michael Paul, Jan-Dierk Grunwaldt, Søren Kegnæs, Claus H. Christensen and Kresten Egeblad

      Article first published online: 9 APR 2010 | DOI: 10.1002/anie.200906977

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      The Dark Crystal: A hybrid material is reported that is comprised of 1–2 nm sized gold nanoparticles, accessible only through zeolite micropores in a silicalite-1 crystal, as shown by three-dimensional TEM tomography (see picture). Calcination experiments indicate that the embedded nanoparticles are highly stable towards sintering.

    13. Molecular Electronics

      In Situ Stepwise Synthesis of Functional Multijunction Molecular Wires on Gold Electrodes and Gold Nanoparticles (pages 3508–3512)

      Geoffrey J. Ashwell, Barbara Urasinska-Wojcik and Laurie J. Phillips

      Article first published online: 31 MAR 2010 | DOI: 10.1002/anie.200906607

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      Tunneling through: The sequencing of electron-donating and electron-accepting components that are separated by a σ-electron bridge has resulted in the highest rectification ratio to date from a molecular diode.

    14. Natural Product Synthesis (1)

      Asymmetric, Protecting-Group-Free Total Synthesis of (−)-Englerin A (pages 3513–3516)

      Qianghui Zhou, Xiaofei Chen and Dawei Ma

      Article first published online: 6 APR 2010 | DOI: 10.1002/anie.201000888

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      The golden touch: Total synthesis of natural (−)-englerin A from (R)-citronellal has been achieved using a gold-catalyzed cyclization as the key step (see scheme). No protecting-group manipulations were required in the synthetic sequence.

    15. Natural Product Synthesis (2)

      Enantioselective Synthesis of (−)-Englerins A and B (pages 3517–3519)

      Kian Molawi, Nicolas Delpont and Antonio M. Echavarren

      Article first published online: 6 APR 2010 | DOI: 10.1002/anie.201000890

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      All that glitters is gold: The total synthesis of the natural enantiomers of englerins A and B has been completed using a gold-catalyzed stereoselective domino alkyne/alkene/carbonyl cyclization of an enyne with an unprotected alcohol group at a stereogenic allylic position (see scheme; TES=triethylsilyl).

    16. Caged Fluorescence

      Rhodamines NN: A Novel Class of Caged Fluorescent Dyes (pages 3520–3523)

      Vladimir N. Belov, Christian A. Wurm, Vadim P. Boyarskiy, Stefan Jakobs and Stefan W. Hell

      Article first published online: 9 APR 2010 | DOI: 10.1002/anie.201000150

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      A bright future: The reaction of diazomethane with acid chlorides obtained from N,N,N′,N′-tetraalkylrhodamines affords 2-diazo-2,3-dihydro-1H-indenespiro[1,9′]-9H-xanthen-3-ones—a novel class of caged rhodamines. These dyes allow new imaging procedures based on the step-wise activation and detection of several fluorescent markers (see picture).

    17. Drug Design

      Synthesis of Azaspirocycles and their Evaluation in Drug Discovery (pages 3524–3527)

      Johannes A. Burkhard, Björn Wagner, Holger Fischer, Franz Schuler, Klaus Müller and Erick M. Carreira

      Article first published online: 1 APR 2010 | DOI: 10.1002/anie.200907108

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      Make it spiro! Readily synthesized heteroatom-substituted spiro[3.3]heptanes generally show higher aqueous solubility than their cyclohexane analogues, and show a trend towards higher metabolic stability. The novel framework can be mounted onto scaffolds of druglike structures, such as fluoroquinolones, to afford active compounds with similar or even improved metabolic stability.

    18. Protein Folding

      A “Force Buffer” Protecting Immunoglobulin Titin (pages 3528–3531)

      João M. Nunes, Ulf Hensen, Lin Ge, Manuela Lipinsky, Jonne Helenius, Helmut Grubmüller and Daniel J. Muller

      Article first published online: 30 MAR 2010 | DOI: 10.1002/anie.200906388

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      The adventures of titin: in vertebrates, titin filaments control the extendibility of the muscle sarcomere. The titin immunoglobulin 27 unfolds through an intermediate (see structure; arrow: hydrogen bonds ruptured to reach intermediate) that it is highly independent of the force load applied. It is shown that this intermediate acts as a “force buffer” that protects immunoglobulin from unfolding at physiologically applied forces.

    19. Hindered Rotation

      Optical Stability of Axially Chiral Push–Pull-Substituted Buta-1,3-dienes: Effect of a Single Methyl Group on the C60 Surface (pages 3532–3535)

      Michio Yamada, Pablo Rivera-Fuentes, W. Bernd Schweizer and François Diederich

      Article first published online: 1 APR 2010 | DOI: 10.1002/anie.200906853

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      A new spin on C60: Axially chiral, push–pull buta-1,3-diene chromophores conjugated to vicinally methylated fullerenes (see picture) have high barriers of rotation about their chiral axes. These high barriers allowed their optical resolution and the determination of the absolute configuration by comparison of experimental and calculated circular dichroism spectra. The methyl group is rigidly fixed upon the surface of the carbon sphere and is responsible for the high rotational barriers.

    20. Dodecaborates

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      Synthesis, Crystal Structure, and Reactivity of the Strong Methylating Agent Me2B12Cl12 (pages 3536–3538)

      Christoph Bolli, Janis Derendorf, Mathias Keßler, Carsten Knapp, Harald Scherer, Christoph Schulz and Jonas Warneke

      Article first published online: 6 APR 2010 | DOI: 10.1002/anie.200906627

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      Give Me strength: Methylation of the easily accessible weakly coordinating dianion [B12Cl12]2− affords Me2B12Cl12 (see picture). This neutral compound is a stronger methylating agent than commonly used methyl triflate, and it even methylates benzene. The synthesis, crystal structure, and reactivity of Me2B12Cl12 in solution and the gas phase are discussed.

  11. Preview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Reviews
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Preview: Angew. Chem. Int. Ed. 21/2010 (page 3543)

      Article first published online: 28 APR 2010 | DOI: 10.1002/anie.201090061

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