Angewandte Chemie International Edition

Cover image for Vol. 49 Issue 38

September 10, 2010

Volume 49, Issue 38

Pages 6685–6907

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Book Review
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Cover Picture: Supersensitive Detection of Explosives by Silicon Nanowire Arrays (Angew. Chem. Int. Ed. 38/2010) (page 6685)

      Yoni Engel, Roey Elnathan, Alexander Pevzner, Guy Davidi, Prof. Eli Flaxer and Prof. Fernando Patolsky

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201004012

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      TNT and other explosives can be detected in air by using silicon nanowire arrays modified with electron-rich aminosilane monolayers. As F. Patolsky and co-workers report in their Communication on page 6830 ff., these devices, in which the electron-deficient explosive molecules are bound to the monolayer through charge-transfer interactions, offer rapid label-free detection of explosives down to a detection limit of 0.1 femtomolar (1×10−6 ppt). Artwork by Tremani.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Book Review
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Inside Cover: Graphene Oxide: A Convenient Carbocatalyst for Facilitating Oxidation and Hydration Reactions (Angew. Chem. Int. Ed. 38/2010) (page 6686)

      Daniel R. Dreyer, Dr. Hong-Peng Jia and Prof. Christopher W. Bielawski

      Version of Record online: 2 JUL 2010 | DOI: 10.1002/anie.201003238

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      Carbocatalysis the intersection of carbon materials and catalysis—is the use of large-area, metal-free carbon to facilitate chemical reactions. In their Communication on page 6813 ff., C. Bielawski and co-workers demonstrate that graphene-based materials may be used as carbocatalysts to facilitate a number of synthetically useful transformations, including the oxidation of alcohols and alkenes into their respective aldehydes and ketones, as well as the hydration of alkynes.

  3. Graphical Abstract

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Book Review
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. You have free access to this content
      Metal–Silicon Triple Bonds: The Molybdenum Silylidyne Complex [Cp(CO)2Mo≡Si-R] (page 6700)

      Prof. Dr. Alexander C. Filippou, Oleg Chernov, Kai W. Stumpf and Dr. Gregor Schnakenburg

      Version of Record online: 7 SEP 2010 | DOI: 10.1002/anie.201090122

      This article corrects:

      Metal–Silicon Triple Bonds: The Molybdenum Silylidyne Complex [Cp(CO)2Mo≡Si-R]1

      Vol. 49, Issue 19, 3296–3300, Version of Record online: 16 APR 2010

  5. News

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Book Review
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Ramón Martínez-Máñez (page 6708)

      Version of Record online: 26 AUG 2010 | DOI: 10.1002/anie.201004419

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      “My favorite subjects at school were scientific subjects such as chemistry, biology, mathematics, and physics. I also liked philosophy. The biggest problem that scientists face is financial support (and the time invested in getting it). …” This and more about Ramón Martínez-Máñez can be found on page 6708.

  7. Book Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Book Review
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Modern Molecular Photochemistry of Organic Molecules. By Nicholas J. Turro, V. Ramamurthy and Juan C. Scaiano. (pages 6709–6710)

      Maurizio Fagnoni

      Version of Record online: 24 AUG 2010 | DOI: 10.1002/anie.201003826

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      University Science Books, Sausalito, California 2010. 1110 pp., hardcover $ 134.50.—ISBN 978-1891389252

  8. Highlights

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

      Functionalization of Methane in Anaerobic Microorganisms (pages 6712–6713)

      Prof. Dr. Rudolf K. Thauer

      Version of Record online: 29 JUL 2010 | DOI: 10.1002/anie.201002967

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      More than one way to skin a cat: Some strictly anaerobic bacteria grow in the presence of methane and nitrite, forming CO2 and N2. Recently published experimental evidence suggests the involvement of a NO dismutase and of a particulate methane monooxygenase (pMMO) in the process. Both enzymes are lacking in microorganisms that catalyze anaerobic methane oxidation with sulfate. There are thus at least two pathways that enable anaerobes to use methane as fuel.

    2. Methane Monooxygenase

      One is Lonely and Three is a Crowd: Two Coppers Are for Methane Oxidation (pages 6714–6716)

      Dr. Richard A. Himes, Dr. Kevin Barnese and Prof. Dr. Kenneth D. Karlin

      Version of Record online: 29 JUL 2010 | DOI: 10.1002/anie.201003403

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      What/where is the active site? The determination of the metal ion content and makeup of the bacterial membrane protein methane monooxygenase (pMMO) has an enigmatic research history, despite protein X-ray structures. A new study appears to settle the issue; the dicopper center facilitates oxidation of methane to methanol. However, the unusual active-site environment leaves many questions for future investigations on the relevant copper-dioxygen chemistry and biochemistry.

  9. Minireview

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

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      Exploiting Cavities in Supramolecular Gels (pages 6718–6724)

      Jonathan A. Foster and Prof. Jonathan W. Steed

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201000070

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      Through the incorporation of cavities into supramolecular gelators, the well-established host–guest chemistry of cavitands can be utilized to build up and break down gel structures, introduce responsive functionalities, and enhance selectivity in applications such as catalysis and extraction.

  10. Review

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

      Luminescent Carbon Nanodots: Emergent Nanolights (pages 6726–6744)

      Dr. Sheila N. Baker and Dr. Gary A. Baker

      Version of Record online: 4 AUG 2010 | DOI: 10.1002/anie.200906623

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      A glowing review: Carbon nanodots have recently emerged as intriguing, cheap, sustainable, and low-toxicity nanoemitters that hold immense promise in energy conversion, bioimaging, diagnostics, and novel composites. This Review summarizes recent advances in the synthesis, understanding, and exploitation of carbon-based quantum dots as nascent biolabels, while pointing to potential new directions for this fascinating class of nanocarbon.

  11. Communications

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

      An Efficient Titanium Catalyst for Enantioselective Cyanation of Aldehydes: Cooperative Catalysis (pages 6746–6750)

      Dr. Zhipeng Zhang, Dr. Zheng Wang, Dr. Ruzhou Zhang and Prof. Dr. Kuiling Ding

      Version of Record online: 14 JUL 2010 | DOI: 10.1002/anie.201002127

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      Two-in-one: The integration of two salen/Ti[DOUBLE BOND]O units into one molecule allows the enantioselective cyanation of aldehydes to afford the enantioenriched natural or nonnatural cyanohydrin derivatives with turnover numbers of 1960–172 000 and ee values up to 97 % (see scheme). Some of the cyanohydrin derivatives are key intermediates for the synthesis of chiral pharmaceuticals or agrochemicals.

    2. Metal–Organic Frameworks

      A Catenated Strut in a Catenated Metal–Organic Framework (pages 6751–6755)

      Dr. Qiaowei Li, Chi-Hau Sue, Dr. Subhadeep Basu, Alexander K. Shveyd, Dr. Wenyu Zhang, Gokhan Barin, Lei Fang, Dr. Amy A. Sarjeant, Prof.  J. Fraser Stoddart and Prof. Omar M. Yaghi

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201003221

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      MIMs meet MOFs: Mechanically interlocked molecules (MIMs), in the form of donor–acceptor [2]catenane-containing struts of exceptional length, have been incorporated into a three-dimensional catenated metal–organic framework (MOF) at precise locations and with uniform relative orientations. Catenation is expressed simultaneously within the struts and the framework.

    3. Micelles

      Self-Division of Macroscopic Droplets: Partitioning of Nanosized Cargo into Nanoscale Micelles (pages 6756–6759)

      Kevin P. Browne, David A. Walker, Dr. Kyle J. M. Bishop and Prof. Bartosz A. Grzybowski

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201002551

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      Divide yourselves! An interfacial reaction drives the spontaneous and sequential division of macroscopic droplets all the way into nanoscopic emulsions (see picture). The sizes of the divided droplets depend on the pH of the solution and the division process is governed by the interplay between surface tension and electrostatic effects. When the dividing droplets contain nanoscopic cargo (e.g., nanorods), they partition it equally into progeny micelles.

    4. Crystal Engineering

      Self-Assembly of Nanotriangle Superlattices Facilitated by Repulsive Electrostatic Interactions (pages 6760–6763)

      David A. Walker, Kevin P. Browne, Dr. Bartlomiej Kowalczyk and Prof. Bartosz A. Grzybowski

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201002558

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      SERSly good! Crystallization of triangular gold nanoprisms into close-packed mono- and multilayers is facilitated by electrostatic repulsions. The ordering of the nanotriangles causes an order-of-magnitude increase in surface-enhanced Raman spectroscopy (SERS) enhancement relative to that of disordered assemblies.

    5. Heteroaromatics

      A Nanoscale Jigsaw-Puzzle Approach to Large π-Conjugated Systems (pages 6764–6767)

      Dr. Xingfa Gao, Prof. Dr. Shengbai B. Zhang, Prof. Dr. Yuliang Zhao and Prof. Dr. Shigeru Nagase

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201002617

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      Piecing the puzzle together: A simple model of stability for hybrid carbon-conjugated materials is revealed and computationally verified. Based on this model, a simple “jigsaw-puzzle” strategy towards the design for a family of highly viable hybrid carbon-conjugated materials is proposed (see picture; C green, N blue, H white).

    6. Epigenetics

      Interaction of Propionylated and Butyrylated Histone H3 Lysine Marks with Brd4 Bromodomains (pages 6768–6772)

      Friederike Vollmuth and Priv.-Doz. Dr. Matthias Geyer

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201002724

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      Recognized as sisters: Histone modifications determine the state of chromatin remodeling and gene activation. Lysine propionylation and butyrylation have been identified as new histone marks (besides acetylation) that expand the epigenetic code. The alignment of the additional methylene groups of such propionylated (see picture) and butyrylated lysine residues between a highly conserved Pro–Phe motif suggests a general mode of bromodomain recognition.

    7. Chemical Bioimaging

      Quantitative CARS Molecular Fingerprinting of Single Living Cells with the Use of the Maximum Entropy Method (pages 6773–6777)

      Masanari Okuno, Prof. Dr. Hideaki Kano, Prof. Dr. Philippe Leproux, Prof. Dr. Vincent Couderc, Dr. James P. R. Day, Prof. Dr. Mischa Bonn and Prof. Dr. Hiro-o Hamaguchi

      Version of Record online: 2 AUG 2010 | DOI: 10.1002/anie.201001560

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      Fast CARS: The cell-death process was observed in real time at the subcellular level by coherent anti-Stokes Raman microspectroscopy, an extension of anti-Stokes Raman scattering (CARS) microscopy. Changes in the chemical contrast during the dying process can be clearly resolved (see picture).

    8. Protein Dynamics

      NMR-Based Protein Potentials (pages 6778–6780)

      Dr. Da-Wei Li and Prof. Rafael Brüschweiler

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201001898

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      Speed training: A highly efficient screening of new potentials against the parent molecular dynamics (MD) trajectories of trial proteins provides a greater than 105-fold increase in the speed of the analysis by using a re-weighting scheme guided by experimental NMR data for proteins, thereby improving the accuracy of computer simulations of proteins.

    9. Nanostructures

      Monodisperse Gold–Copper Bimetallic Nanocubes: Facile One-Step Synthesis with Controllable Size and Composition (pages 6781–6785)

      Dr. Yonglin Liu and Dr. A. R. Hight Walker

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201001931

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      Precision preparation: A facile, one-step, polyol protocol has been developed to prepare monodisperse, single-crystalline Au–Cu bimetallic nanocubes. Through the careful adjustment of the reaction parameters, both the dimensions of the nanocubes (two examples with edge lengths of 23 and 5 nm are shown) and their gold and copper stoichiometry can be controlled.

    10. Two-Photon Fluorescent Probes

      Dual-Color Imaging of Sodium/Calcium Ion Activities with Two-Photon Fluorescent Probes (pages 6786–6789)

      Hyung Joong Kim, Ji Hee Han, Mi Kyung Kim, Chang Su Lim, Prof. Hwan Myung Kim and Prof. Bong Rae Cho

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201002907

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      A two-photon probe (BCaM) shows 14-fold enhancement in two-photon emission fluorescence in response to Ca2+ and shows high sensitivity and selectivity for near-membrane Ca2+ ions (see picture). Combined with the known Na+ two-photon probe ANa1, BCaM allows simultaneous dual-color imaging of Ca2+/Na+ activities within live cells and in tissues at more than 100 μm depth for long time periods without photobleaching.

    11. Molecular Sieves

      Unified Internal Architecture and Surface Barriers for Molecular Diffusion of Microporous Crystalline Aluminophosphates (pages 6790–6794)

      Lukasz Karwacki, Hendrik E. van der Bij, Dr. Jan Kornatowski, Dr. Pablo Cubillas, Dr. Martyn R. Drury, D. A. Matthijs de Winter, Prof. Dr. Michael W. Anderson and Prof. Dr. Bert M. Weckhuysen

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201003273

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      Starless molecular sieves: The starlike appearence of confocal fluorescence microscopy (CFM) images of large crystals of the AlPO-5 family of microporous materials is due to the presence of barriers to molecular diffusion in the internal crystal architecture (see picture) rather than a star-shaped subcrystal according to studies by CFM, focused ion beam milling, electron backscatter diffraction, and atomic force microscopy.

    12. Metalloprotein Proinhibitors

      Hydrogen Peroxide Activated Matrix Metalloproteinase Inhibitors: A Prodrug Approach (pages 6795–6797)

      Dr. Jody L. Major Jourden and Prof. Seth M. Cohen

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201003819

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      Doing double duty: A metalloproteinase inhibitor that can be activated by reactive oxygen species (ROS) has been designed to protect the blood-brain barrier (BBB) in ischemic reperfusion injury. By both neutralizing damaging ROS and inhibiting degradative metalloproteinases, a single compound can eliminate both threats to the BBB upon activation.

    13. Atomic Carbon Sources

      An Isolable Mixed P,S-Bis(ylide) as an Asymmetric Carbon Atom Source (pages 6798–6801)

      Nicolas Dellus, Dr. Tsuyoshi Kato, Xavier Bagán, Dr. Nathalie Saffon-Merceron, Prof. Vicenç Branchadell and Dr. Antoine Baceiredo

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201002833

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      Heart of carbon: The first stable asymmetric bis(ylide), N,N′-(iPr2NCH2CH2NiPr)(Ph)P[BOND]C[BOND]SPh2, has been isolated (see picture; C black, N gray). The presence of the two different ligands causes this carbon(0) complex to behave as an asymmetric atomic carbon source.

    14. Proteomics

      A Cleavable Linker Based on the Levulinoyl Ester for Activity-Based Protein Profiling (pages 6802–6805)

      Paul P. Geurink, Dr. Bogdan I. Florea, Nan Li, Dr. Martin D. Witte, Joeri Verasdonck, Chi-Lin Kuo, Prof. Dr. Gijs A. van der Marel and Prof. Dr. Herman S. Overkleeft

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201001767

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      Get linked: The title linker is stable under various biological conditions and can be cleaved chemoselectively with hydrazine (see scheme). Its use is demonstrated in the activity-based enrichment and identification of proteasome active subunits from cell extracts.

    15. Gold Catalysis

      Gold(I)-Catalyzed Addition of Diphenyl Phosphate to Alkynes: Isomerization of Kinetic Enol Phosphates to the Thermodynamically Favored Isomers (pages 6806–6809)

      Prof. Dr. Phil Ho Lee, Dr. Sundae Kim, Aeri Park, Bathoju Chandra Chary and Prof. Dr. Sunggak Kim

      Version of Record online: 4 AUG 2010 | DOI: 10.1002/anie.201001799

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      Gold, gold, or … gold? It depends on the (gold) catalyst whether the product of thermodynamic or kinetic control is formed in an unprecedented hydrophosphoryloxylation approach to enol phosphates (see scheme). A third catalyst, [(C6F5)3PAuOTf], was found to be exceedingly effective for the previously unknown isomerization of kinetic enol phosphates to the thermodynamically favored isomers. Tf=trifluoromethanesulfonyl; R=alkyl, cyclohexyl, Ph.

    16. Emulsion Polymerization

      Aqueous Dispersions of Nonspherical Polyethylene Nanoparticles from Free-Radical Polymerization under Mild Conditions (pages 6810–6812)

      Etienne Grau, Pierre-Yves Dugas, Jean-Pierre Broyer, Dr. Christophe Boisson, Dr. Roger Spitz and Dr. Vincent Monteil

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201001800

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      A radical idea: Free-radical polymerization of ethylene usually requires severe conditions. Here, the efficiency of this reaction was investigated under mild conditions (less than 250 bar) in water for the production of stable polyethylene (PE) aqueous dispersions (see picture, Dp=particle diameter). Latexes of PE nanoparticles with various shapes (cylinder or sphere) and solid contents up to 40 % were prepared.

    17. Carbocatalysis

      Graphene Oxide: A Convenient Carbocatalyst for Facilitating Oxidation and Hydration Reactions (pages 6813–6816)

      Daniel R. Dreyer, Dr. Hong-Peng Jia and Prof. Christopher W. Bielawski

      Version of Record online: 2 JUL 2010 | DOI: 10.1002/anie.201002160

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      Do not pass GO: Graphene oxide (GO) catalyzes the oxidation of various alcohols and alkenes, and the hydration of various alkynes into their respective aldehydes and ketones in good to excellent yields. The reactions proceed under relatively mild conditions and simple filtration was shown to be a convenient and effective method of catalyst recovery.

    18. Click Chemistry

      An Unexpected Example of Protein-Templated Click Chemistry (pages 6817–6820)

      Dr. Takayoshi Suzuki, Yosuke Ota, Yuki Kasuya, Dr. Motoh Mutsuga, Dr. Yoko Kawamura, Dr. Hiroki Tsumoto, Dr. Hidehiko Nakagawa, Prof. M. G. Finn and Prof. Naoki Miyata

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201002205

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      It all happened with a click: In a search for histone deacetylase (HDAC) inhibitors using in situ click chemistry, the first example of protein–Cu acceleration of the azide–alkyne cycloaddition reaction was uncovered. The copper center in the protein target HDAC8 catalyzed triazole formation between one azide–alkyne pair among 30 possibilities. These results provide a new route to HDAC inhibitors and a precedent for new types of protein-based catalysts for click chemistry.

    19. Radiochemistry

      Radiosynthesis and Evaluation of [18F]Selectfluor bis(triflate) (pages 6821–6824)

      Harriet Teare, Dr. Edward G. Robins, Anna Kirjavainen, Sarita Forsback, Prof. Graham Sandford, Prof. Olof Solin, Dr. Sajinder K. Luthra and Prof. Véronique Gouverneur

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201002310

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      Selectfluor, one of the most reactive and commonly used electrophilic fluorinating N–F reagents, has been radiolabeled with 18F. The resulting new [18F]-labeled N–F reagent is safe, nontoxic, and easy to handle. The combined use of [18F]Selectfluor bis(triflate) and AgOTf allows for the preparation of electron-rich 18F-aromatic compounds through a simple “shake and mix” protocol at room temperature (see scheme; SA=specific activtiy).

    20. Microreactors

      A Microchemical System with Continuous Recovery and Recirculation of Catalyst-Immobilized Magnetic Particles (pages 6825–6829)

      Dr. Chan Pil Park and Prof. Dr. Dong-Pyo Kim

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201002490

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      Keep on running: A microchemical system for continuous flow catalytic reactions with a magnetic catalyst is presented (see picture). It enables the automatic separation and recirculation of catalyst particles and is applicable to various catalytic reactions.

    21. Sensors

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      Supersensitive Detection of Explosives by Silicon Nanowire Arrays (pages 6830–6835)

      Yoni Engel, Roey Elnathan, Alexander Pevzner, Guy Davidi, Prof. Eli Flaxer and Prof. Fernando Patolsky

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201000847

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      Dog on a chip: Explosives can be detected with unprecedented sensitivity by using arrays of silicon nanowire field-effect transistors modified with an electron-rich aminosilane monolayer, which form complexes with the analytes (see picture). These “nanosniffers” can be used to sense the presence of TNT at concentrations as low as 1×10−6 ppt, which is superior to that of sniffer dogs or any other known explosive detection method.

    22. Conformational Communication

      Nanometer-Range Communication of Stereochemical Information by Reversible Switching of Molecular Helicity (pages 6836–6839)

      Dr. Jordi Solà, Dr. Stephen P. Fletcher, Dr. Alejandro Castellanos and Prof. Jonathan Clayden

      Version of Record online: 4 AUG 2010 | DOI: 10.1002/anie.201001130

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      A long-distance call: The inversion of configuration at a stereogenic center led to a detectable switch in the position of a 13C stereochemical probe 40 bonds (2.5 nm) away. Information was relayed between the sites by an inversion of screw sense in the intervening helix as illustrated (13C NMR signals were read as output).

    23. Computational Chemistry

      Mechanistic Insights into Direct Amide Bond Formation Catalyzed by Boronic Acids: Halogens as Lewis Bases (pages 6840–6843)

      Dr. Tommaso Marcelli

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201003188

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      Get the water out! DFT calculations predict water elimination from a tetrahedral intermediate to be the rate determining step in the title reaction. This transformation is calculated to be highly stereoselective, yielding cis amides as the kinetic products (see scheme). The superior activity of ortho-halophenyl boronic acids results from the Lewis basic character of halogen atoms.

    24. Organocatalysis

      Enantioselective Formal Alkenylations of Imines Catalyzed by Axially Chiral Dicarboxylic Acid Using Vinylogous Aza-Enamines (pages 6844–6847)

      Dr. Takuya Hashimoto, Hidenori Kimura and Prof. Dr. Keiji Maruoka

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201003600

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      In the zone: The use of vinylogous aza-enamaines (hydrazones) as a source of an alkenyl group has been achieved (see scheme). Unmasking of the aza-enamine moiety opens up a novel approach for the preparation of chiral allylic amines bearing an electron-withdrawing alkene moiety functionalized at the electron-deficient β position.

    25. Shape-Controlled Catalysts

      Enhancing by Weakening: Electrooxidation of Methanol on Pt3Co and Pt Nanocubes (pages 6848–6851)

      Dr. Hongzhou Yang, Dr. Jun Zhang, Dr. Kai Sun, Prof. Shouzhong Zou and Prof. Jiye Fang

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201002888

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      Loaded dice: High-quality and similarly sized Pt3Co and Pt nanocubes were prepared by gradually reducing metal precursors at high temperatures. Cyclic voltammetric and chronoamperometric results show a much higher methanol oxidation current density on Pt3Co nanocubes (see picture). The enhanced catalytic activity was explained by the slower and weaker adsorption of CO onto Pt3Co.

    26. Coupling Reactions

      Selective P[BOND]P and P[BOND]O[BOND]P Bond Formations through Copper-Catalyzed Aerobic Oxidative Dehydrogenative Couplings of H-Phosphonates (pages 6852–6855)

      Dr. Yongbo Zhou, Prof. Dr. Shuangfeng Yin, Yuxing Gao, Prof. Dr. Yufen Zhao, Dr. Midori Goto and Dr. Li-Biao Han

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201003484

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      Different copper complexes selectively catalyze the aerobic oxidative coupling of H-phosphonates to afford either hypophosphates and pyrophosphates in high yields with high selectivity (see scheme; tmeda=N,N,N′,N′-tetramethylethylenediamine).

    27. Cross-Coupling

      Arylation of α-Chiral Ketones by Palladium-Catalyzed Cross-Coupling Reactions of Tosylhydrazones with Aryl Halides (pages 6856–6859)

      Prof. José Barluenga, María Escribano, Prof. Fernando Aznar and Dr. Carlos Valdés

      Version of Record online: 3 AUG 2010 | DOI: 10.1002/anie.201003450

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      Papa was a rollin' ketone: Arylation of ketones with preservation of the chirality in configurationally unstable α-chiral ketones has been achieved by the palladium-catalyzed cross-coupling reaction between tosylhydrazones and aryl halides (see scheme; Boc=tert-butoxycarbonyl, Ts=4-toluenesulfonyl). The regioselectivity in the β-hydride elimination step is key for the retention of configuration.

    28. Phosphorus Cages

      Access to Extended Polyphosphorus Frameworks (pages 6860–6864)

      Dipl.-Chem. Fabian Dielmann, Dr. Marek Sierka, Dr. Alexander V. Virovets and Prof. Dr. Manfred Scheer

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201001000

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      Under control: Controlled self-aggregation of P4 to extended neutral polyphosphorus cages was achieved in the presence of cobalt complex fragments. X-ray structure analyses of P12, P16, and P24 ligand complexes give insights into the formation of aggregated allotropes of phosphorus from elemental P4.

    29. Quantum Dots

      Semiconductor Nanocrystals with Adjustable Hole Acceptors: Tuning the Fluorescence Intensity by Metal–Ion Binding (pages 6865–6868)

      Jessica Völker, Xiaoyin Zhou, Xuedan Ma, Sandra Flessau, Dr. Hengwei Lin, Prof. Michael Schmittel and Prof. Alf Mews

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201001441

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      Functional ligands: The fluorescence intensity of semiconductor nanocrystals (NCs) strongly depends on the energy level arrangement of the nanocrystals (the valence band (VB) and conducting band (CB)) and their molecular ligands. Using a functional ligand such as 1, where the oxidation potential can be adjusted by metal–ion complexation, the fluorescence of the nanocrystals can be used for metal ion recognition.

    30. Organolithium Compounds

      Consecutive Donor-Base Exchange in Anthracenyllithium Compounds (pages 6869–6872)

      Dr. Daniel Stern, Nils Finkelmeier, Dr. Kathrin Meindl, Dr. Julian Henn and Prof. Dr. Dietmar Stalke

      Version of Record online: 2 AUG 2010 | DOI: 10.1002/anie.201002873

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      Selective and consecutive donor-base addition and exchange in the same organolithium complex was monitored by structural determination, although it is feasible to fine-tune the composition of a mixed-base complex by stoichiometric addition of a second donor base. Remarkably, the length of the Li[BOND]Cα bonds is proportional to the reactivity as measured by frontier orbital energies with increasing amounts of the better donor base.

    31. Ligand Design

      Chiral Mixed Secondary Phosphine-Oxide–Phosphines: High-Performing and Easily Accessible Ligands for Asymmetric Hydrogenation (pages 6873–6876)

      Heidi Landert, Dr. Felix Spindler, Adrian Wyss, Dr. Hans-Ulrich Blaser, Dr. Benoît Pugin, Dr. Yann Ribourduoille, Björn Gschwend, Dr. Balamurugan Ramalingam and Prof. Andreas Pfaltz

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201002225

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      P&O: Combining secondary phosphine oxides (SPOs) with phosphines leads to highly effective chiral bidentate ligands for transition-metal-based catalysts. JoSPOphos and TerSPOphos are readily accessible from inexpensive starting materials. The steric and electronic properties of these modular ligands can be easily tuned. In the asymmetric hydrogenation of functionalized alkenes, their rhodium complexes reacted to give enantioselectivities of up to 99 % ee and turnover frequencies of up to 20 000 h−1.

    32. Oxyarylation

      1,2,3-Trisubstituted Indanes by Highly Diastereoselective Palladium-Catalyzed Oxyarylation of Indenes with Arylboronic Acids and Nitroxides (pages 6877–6880)

      Sylvia Kirchberg, Dr. Roland Fröhlich and Prof. Dr. Armido Studer

      Version of Record online: 4 AUG 2010 | DOI: 10.1002/anie.201002214

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      Excellent stereoselectivity is obtained in the synthesis of biologically interesting 1,2,3-trisubstituted indanes B by the reaction of readily prepared 3-substituted indenes A with commercially available arylboronic acids by using various TEMPO derivatives as external oxidants and Pd(OAc)2 as a catalyst. The anti,anti isomers are formed and reactions occur stereospecifically under mild conditions.

    33. Surface Chemistry

      Dynamic Microcrystal Assembly by Nitroxide Exchange Reactions (pages 6881–6884)

      Dr. Birte Schulte, Dr. Manuel Tsotsalas, Maike Becker, Prof. Dr. Armido Studer and Prof. Dr. Luisa De Cola

      Version of Record online: 3 AUG 2010 | DOI: 10.1002/anie.201002851

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      Sticking together: The pore entrances of dye-loaded green or red zeolite L crystals can be site-specifically modified with either alkoxyamines or nitroxide radicals. Mild radical nitroxide exchange reactions of alkoxyamine-terminated “green” zeolite crystals with nitroxide-terminated “red” crystals leads to highly regular crystal chains that contain up to 15 covalently connected crystals with strictly alternating colors.

    34. Acidity

      A Unified pH Scale for All Phases (pages 6885–6888)

      Dr. Daniel Himmel, Dipl.-Chem. Sascha K. Goll, Prof. Dr. Ivo Leito and Prof. Dr. Ingo Krossing

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201000252

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      One for all! On the basis of the absolute chemical potential of the proton, a unified absolute pH scale is introduced that is universally applicable in the gas phase, in solution, and in the solid state. With this scale, it is possible to directly compare acidities in different media, and to give a thermodynamically meaningful definition of superacidity. This scale can be used in all areas with variable proton activity.

    35. Structural Biology

      Directional Proton Transfer in Membrane Proteins Achieved through Protonated Protein-Bound Water Molecules: A Proton Diode (pages 6889–6893)

      Dr. Steffen Wolf, Erik Freier, Dr. Meike Potschies, Prof. Dr. Eckhard Hofmann and Prof. Dr. Klaus Gerwert

      Version of Record online: 2 AUG 2010 | DOI: 10.1002/anie.201001243

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      While proton transfer in liquid water is random, membrane proteins creating the proton gradient for ATP synthesis perform a directional proton transfer via protein-bound protonated water molecules. This was shown in bacteriorhodopsin by a combination of time-resolved FTIR spectroscopy, X-ray crystallography, and molecular dynamics simulations.

    36. Functionalized Phosphanyl Complexes

      Insights into the Chemistry of Transient P-Chlorophosphanyl Complexes (pages 6894–6898)

      Aysel Özbolat-Schön, Dr. Maren Bode, Dr. Gregor Schnakenburg, Dr. Anakuthil Anoop, Dr. Maurice van Gastel, Prof. Dr. Frank Neese and Prof. Dr. Rainer Streubel

      Version of Record online: 16 AUG 2010 | DOI: 10.1002/anie.201002885

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      C[BOND]P or C[DOUBLE BOND]P? One-electron oxidation of Li/Cl phosphinidenoid complexes led to the discovery of transient P-chlorophosphanyl complexes 1. Subsequent cross-coupling and rearrangement or elimination reactions yielded 2 and 3; the latter is the first structurally characterized phosphaquinomethane complex. ESR spectroscopy and DFT calculations support the existence of short-lived P-centered radicals.

    37. Cluster Compounds

      Metal-Rich Copper Chalcogenide Clusters at the Border Between Molecule and Bulk Phase: The Structures of [Cu93Se42(SeC6H4SMe)9(PPh3)18], [Cu96Se45(SeC6H4SMe)6(PPh3)18], and [Cu136S56(SCH2C4H3O)24(dpppt)10] (pages 6899–6903)

      Dr. Ming-Lai Fu, Dr. Ibrahim Issac, Prof. Dr. Dieter Fenske and Dr. Olaf Fuhr

      Version of Record online: 2 AUG 2010 | DOI: 10.1002/anie.201001301

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      Between molecule and bulk phase: The three title compounds are examples of ligand-stabilized clusters having significant structural features of the corresponding binary copper(I) chalcogenides. The cluster shown, [Cu136S56(SR)24(dpppt)10], can be seen as an approximate 1.2×1.4×1.9 nm3 section of a cubic phase of Cu2S. The background shows a typical X-ray diffraction image of a single crystal of the cluster.

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