Angewandte Chemie International Edition

Cover image for Angewandte Chemie International Edition

August 29, 2011

Volume 50, Issue 36

Pages 8199–8437

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Editorial
    6. Graphical Abstract
    7. News
    8. Author Profile
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    14. Preview
    1. Cover Picture: Mechanism of Multivalent Carbohydrate–Protein Interactions Studied by EPR Spectroscopy (Angew. Chem. Int. Ed. 36/2011) (page 8199)

      Dipl.-Chem. Patrick Braun, M. Sc. Bettina Nägele, Prof. Dr. Valentin Wittmann and Dr. Malte Drescher

      Version of Record online: 7 JUL 2011 | DOI: 10.1002/anie.201104492

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      State-of-the-art EPR techniques provide structural evidence for multivalent protein–ligand interactions in solution. In their Communication page 8428 ff., V. Wittmann and co-workers report experiments that give a detailed picture of the molecular mechanism of the binding of divalent ligands to a lectin in solution. Chelating binding is detected directly and can be differentiated from the monovalent binding of multiple molecules.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Editorial
    6. Graphical Abstract
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    8. Author Profile
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
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    1. Inside Cover: Palladium-Catalyzed Borylation of Sterically Demanding Aryl Halides with a Silica-Supported Compact Phosphane Ligand (Angew. Chem. Int. Ed. 36/2011) (page 8200)

      Soichiro Kawamorita, Prof. Dr. Hirohisa Ohmiya, Dr. Tomohiro Iwai and Prof. Dr. Masaya Sawamura

      Version of Record online: 15 JUL 2011 | DOI: 10.1002/anie.201104741

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      Immobilizing a monophosphane on a solid surface can exert a strong influence on the catalytic activities of its metal complexes. In their Communication on page 8363 ff., M. Sawamura and co-workers report that a compact monophosphane immobilized on silica gel can be utilized for the Pd-catalyzed borylation of sterically and electronically challenging aryl chlorides. This study shows that nonbulky ligands can be used for aryl chloride activation if the ligands are immobilized.

  3. Back Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Editorial
    6. Graphical Abstract
    7. News
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    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    14. Preview
    1. Back Cover: Efficient Sunlight-Driven Dehydrogenative Coupling of Methane to Ethane over a Zn+-Modified Zeolite (Angew. Chem. Int. Ed. 36/2011)

      Lu Li, Prof. Guo-Dong Li, Chang Yan, Xiao-Yue Mu, Xiao-Liang Pan, Xiao-Xin Zou, Prof. Kai-Xue Wang and Prof. Jie-Sheng Chen

      Version of Record online: 20 JUL 2011 | DOI: 10.1002/anie.201104743

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      Activation of C[BOND]H bonds in saturated hydrocarbons under mild conditions is a great challenge. In their Communication on page 8299 ff. J.-S. Chen and co-workers report a Zn+-modified ZSM-5 material that shows photocatalytic activity for the dehydrogenative coupling of methane to ethane and hydrogen under UV and sunlight irradiation at room temperature. The energy needed to power the photocatalytic system is much lower than that required by previously reported systems.

  4. Editorial

    1. Top of page
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    4. Back Cover
    5. Editorial
    6. Graphical Abstract
    7. News
    8. Author Profile
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    14. Preview
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      Why Help a Growing Scientific Giant? (pages 8202–8203)

      Prof. Richard N. Zare

      Version of Record online: 16 AUG 2011 | DOI: 10.1002/anie.201105242

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      Richard N. Zare

  5. Graphical Abstract

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

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Editorial
    6. Graphical Abstract
    7. News
    8. Author Profile
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
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    1. Ralph Weissleder (pages 8224–8225)

      Version of Record online: 10 AUG 2011 | DOI: 10.1002/anie.201103729

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      „What I look for first in a publication is the problem and then the data. If I won the lottery, I would continue doing science. …“ This and more about Ralph Weissleder can be found on page 8224.

  8. Book Review

    1. Top of page
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    1. Surface Enhanced Raman Spectroscopy. Analytical, Biophysical and Life Science Applications. Edited by Sebastian Schlücker. (page 8226)

      Katrin F. Domke

      Version of Record online: 26 JUL 2011 | DOI: 10.1002/anie.201103289

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      Wiley-VCH, Weinheim 2010. 332 pp., hardcover, € 119.00.—ISBN 978-3527325672

  9. Highlights

    1. Top of page
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    4. Back Cover
    5. Editorial
    6. Graphical Abstract
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    9. Book Review
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    11. Minireview
    12. Review
    13. Communications
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    1. Boronic Acids

      Palladium-Catalyzed Direct Synthesis of Organoboronic Acids (pages 8230–8232)

      Dr. Lukasz T. Pilarski and Prof. Kálmán J. Szabó

      Version of Record online: 30 JUN 2011 | DOI: 10.1002/anie.201102384

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      Diboronic acid in the spotlight: Molander et al. have developed an excellent method for the direct synthesis of aryl boronic acids from aryl chlorides (see scheme). In this palladium-catalyzed procedure, diboronic acid, a notably underutilized reagent, was used as the boron source. The boronic acid products can be isolated from the procedure, or used in one-pot reactions to give a wide range of boronates and biaryls.

    2. Chiral Brønsted Acids

      Asymmetric Brønsted Acid Catalysis Enabling Hydroaminations of Dienes and Allenes (pages 8233–8235)

      Isabelle Dion and Prof. André M. Beauchemin

      Version of Record online: 14 JUL 2011 | DOI: 10.1002/anie.201102408

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      Acid treatment: Toste et al. recently unveiled a new pathway for asymmetric Brønsted acid catalysis of reactions involving dienes or allenes, and achieved highly efficient intramolecular hydroamination and hydroarylation reactions (see scheme). The P[DOUBLE BOND]S bond proved necessary for reactivity, and dithiophosphoric acids emerged as efficient catalysts. The association/displacement sequence led to chiral pyrrolidines and isoxazolidines in excellent yields and ee values.

  10. Minireview

    1. Top of page
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    13. Communications
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    1. Gold Catalysis

      Gold for C[BOND]C Coupling Reactions: A Swiss-Army-Knife Catalyst? (pages 8236–8247)

      Dr. Hermann A. Wegner and Dr. Mathieu Auzias

      Version of Record online: 4 AUG 2011 | DOI: 10.1002/anie.201101603

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      More than just a pretty face: Gold excels as a catalyst for organic synthesis owing to its unique reactivity pattern: its π Lewis acidity as well as its ability to insert into C[BOND]H bonds and to undergo oxidation/reduction processes. This last property in particular offers an efficient means to construct C[BOND]C bonds. The current state of the art of gold-catalyzed C[BOND]C coupling is discussed along with mechanistic aspects of these reactions.

  11. Review

    1. Top of page
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    11. Minireview
    12. Review
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    1. Biomolecular Mass Spectrometry

      Modern Biomolecular Mass Spectrometry and its Role in Studying Virus Structure, Dynamics, and Assembly (pages 8248–8262)

      Dr. Charlotte Uetrecht and Prof. Dr. Albert J. R. Heck

      Version of Record online: 26 JUL 2011 | DOI: 10.1002/anie.201008120

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      Viruses on mass: Structural biology has profited greatly from modern biomolecular mass spectrometry (MS). In this Review a variety of mass spectrometry techniques, including proteomics, H/D exchange, chemical labeling, and native and ion mobility MS, are presented along with how they have contributed to structural-biology investigations, in particular of virus structure, assembly, and dynamics (see picture).

  12. Communications

    1. Top of page
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    1. Foams

      Smart Foams: Switching Reversibly between Ultrastable and Unstable Foams (pages 8264–8269)

      Dr. Anne-Laure Fameau, Dr. Arnaud Saint-Jalmes, Dr. Fabrice Cousin, Bérénice Houinsou Houssou, Dr. Bruno Novales, Dr. Laurence Navailles, Prof. Frédéric Nallet, Dr. Cédric Gaillard, Dr. François Boué and Dr. Jean-Paul Douliez

      Version of Record online: 20 JUL 2011 | DOI: 10.1002/anie.201102115

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      Smart foams: Ultrastable foams with an optimal foamability are obtained using hydroxy fatty acids tubes (see picture). The stabilization results from the adsorption of monomers at the air–water interface and from the presence of tubes in the plateau borders. Upon heating, tubes transform to micelles, leading to foam destabilization and thus to the first foams to exhibit temperature-tuneable stability.

      Corrected by:

      Corrigendum: Corrigendum: Smart Foams: Switching Reversibly between Ultrastable and Unstable Foams

      Vol. 50, Issue 50, 11826, Version of Record online: 7 DEC 2011

    2. Dye-Sensitized Solar Cells

      Tris(thiocyanate) Ruthenium(II) Sensitizers with Functionalized Dicarboxyterpyridine for Dye-Sensitized Solar Cells (pages 8270–8274)

      Shen-Han Yang, Kuan-Lin Wu, Prof. Yun Chi, Dr. Yi-Ming Cheng and Prof. Pi-Tai Chou

      Version of Record online: 20 JUL 2011 | DOI: 10.1002/anie.201103515

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      Panchromatic sensitizers: A series of ruthenium(II) compounds was prepared that contain three thiocyanate ligands and a novel chelating terpyridine ligand. The latter (see picture: colors indicate orbital occupation) serves as an effective and versatile light-harvesting auxochrome. One compound has a solar conversion efficiency of up to 10.3 %.

    3. Structure Elucidation

      Simple Determination of Double-Bond Positions in Long-Chain Olefins by Cross-Metathesis (pages 8275–8278)

      Yongseok Kwon, Seonwoo Lee, Prof. Dr. Dong-Chan Oh and Prof. Dr. Sanghee Kim

      Version of Record online: 24 JUN 2011 | DOI: 10.1002/anie.201102634

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      Cut, paste, and measure: The positions of double bonds in unsaturated long-chain compounds can be easily determined by chemical derivatization using a cross-metathesis reaction and chromatography–mass spectrometry. The produced olefins have distinct physicochemical properties suitable for LC/MS or GC/MS analysis that depend on the cross-metathesis partner used. This method is operationally simple and applicable at a sub-milligram scale.

    4. Metal–Organic Frameworks

      Assembly of the First Fullerene-Type Metal–Organic Frameworks Using a Planar Five-Fold Coordination Node (pages 8279–8282)

      Dr. John Bacsa, Dr. Robert J. Less, Helen E. Skelton, Zlatko Soracevic, Dr. Alexander Steiner, Thomas C. Wilson, Dr. Paul T. Wood and Prof. Dominic S. Wright

      Version of Record online: 26 JUL 2011 | DOI: 10.1002/anie.201102783

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      Pump up the volume: Slow crystallization of Na[C5(CN)5], the unsolvated sodium salt of pentacyanocyclopentadienide, gives the first example of an anionic coordination network based on metal–fullerene units. The structure of this network is closely related to a type I gas clathrate (see picture) in which around 66 % of the unit cell volume is occupied by solvent molecules.

    5. Photochemistry

      Ruthenium(II) Polyimine–Coumarin Dyad with Non-emissive 3IL Excited State as Sensitizer for Triplet–Triplet Annihilation Based Upconversion (pages 8283–8286)

      Shaomin Ji, Dr. Huimin Guo, Wenting Wu, Wanhua Wu and Prof. Jianzhang Zhao

      Version of Record online: 18 JUL 2011 | DOI: 10.1002/anie.201008134

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      Light out of darkness? Most sensitizers for triplet–triplet annihilation (TTA) upconversion are strongly phosphorescent. A new RuII–coumarin dyad, on the other hand, has a non-emissive 3IL excited state (ΦP=0.2 %) but shows a good upconversion quantum yield (ΦUC=2.7 %, see picture, TTET=triplet–triplet energy transfer).

    6. Protein Chemistry

      One-Pot Dual-Labeling of a Protein by Two Chemoselective Reactions (pages 8287–8290)

      Long Yi, Dr. Hongyan Sun, Dr. Aymelt Itzen, Dr. Gemma Triola, Prof. Herbert Waldmann, Prof. Roger S. Goody and Dr. Yao-Wen Wu

      Version of Record online: 14 JUL 2011 | DOI: 10.1002/anie.201100840

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      Dual system for proteins: The site-specific two-color labeling of a Rab GTPase was achieved in a one-pot procedure by combination of chemoselective native chemical ligation and oxime ligation. This strategy could be a general, facile, and efficient method for specific multiple modifications of a given protein. The Rab GTPase biosensor was demonstrated for protein folding and protein–protein interaction studies.

    7. Protein Conformation

      Detection of a Protein Conformational Equilibrium by Electrospray Ionisation-Ion Mobility-Mass Spectrometry (pages 8291–8294)

      Matthew Jenner, Dr. Jacqueline Ellis, Dr. Wei-Cheng Huang, Prof. Dr. Emma Lloyd Raven, Prof. Dr. Gordon C. K. Roberts and Dr. Neil J. Oldham

      Version of Record online: 17 JUN 2011 | DOI: 10.1002/anie.201101077

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      Conforming to convention: Evidence for compact and extended forms of cytochrome P450 reductase, believed to exist in dynamic equilibrium in solution, is found in the gas phase by using ion mobility spectrometry. The relative abundance of the two conformations (see picture) can be influenced by the ionic strength of the solution from which they are electrosprayed.

    8. Selection Methods

      Rapid mRNA-Display Selection of an IL-6 Inhibitor Using Continuous-Flow Magnetic Separation (pages 8295–8298)

      Dr. C. Anders Olson, Dr. Jonathan D. Adams, Prof. Terry T. Takahashi, Hangfei Qi, Shannon M. Howell, Prof. Ting-Ting Wu, Prof. Richard W. Roberts, Prof. Ren Sun and Prof. H. Tom Soh

      Version of Record online: 14 JUL 2011 | DOI: 10.1002/anie.201101149

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      Even flow: Microfluidics technology can rapidly generate affinity reagents that bind to protein targets using mRNA display. The continuous-flow magnetic separation (CFMS) method (see scheme; steps a–h) offers reproducible means to impose stringent selection conditions without the need for a specialized device. The method yields approximately a 30-fold greater partition efficiency over conventional methods when using interleukin-6 as a model target.

    9. Methane Conversion

      Efficient Sunlight-Driven Dehydrogenative Coupling of Methane to Ethane over a Zn+-Modified Zeolite (pages 8299–8303)

      Lu Li, Prof. Guo-Dong Li, Chang Yan, Xiao-Yue Mu, Xiao-Liang Pan, Xiao-Xin Zou, Prof. Kai-Xue Wang and Prof. Jie-Sheng Chen

      Version of Record online: 14 JUL 2011 | DOI: 10.1002/anie.201102320

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      Sun bath: A Zn+-modified zeolite catalyst showing superior photocatalytic activity for the activation of a C[BOND]H bond converted methane into ethane and hydrogen upon irradiation of sunlight (see picture). Light at wavelengths shorter than 390 nm transferred electrons from the zeolite framework to the zinc centers.

    10. Reaction Mechanisms

      Powerful Insight into Catalytic Mechanisms through Simultaneous Monitoring of Reactants, Products, and Intermediates (pages 8304–8306)

      Krista L. Vikse, Zohrab Ahmadi, Cara C. Manning, Dr. David A. Harrington and Dr. J. Scott McIndoe

      Version of Record online: 14 JUN 2011 | DOI: 10.1002/anie.201102630

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      Keeping an eye on all the players: The combination of bulky phosphonium tags and pressurized sample infusion transforms electrospray ionization mass spectrometry into a tool capable of producing dense data on the relative concentrations of all components of a catalytic reaction, such as the palladium-catalyzed coupling of an aryl iodide with phenylacetylene (see graph).

    11. 3D Nanostructures

      Versatile Fabrication of Intact Three-Dimensional Metallic Butterfly Wing Scales with Hierarchical Sub-micrometer Structures (pages 8307–8311)

      Dr. Yongwen Tan, Prof. Dr. Jiajun Gu, Xining Zang, Wei Xu, Kaicheng Shi, Linhua Xu and Prof. Dr. Di Zhang

      Version of Record online: 21 JUL 2011 | DOI: 10.1002/anie.201103505

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      Spread your wings: Surface functionalization of butterfly wing scales and subsequent electroless deposition of different metals produces metallic replicas with 3D sub-micrometer structures (see picture). This approach converts complicated natural 3D bioorganic structures into various otherwise unavailable metal structures with optical, electronic, magnetic, thermal, or catalytic applications.

    12. Nanotechnology

      You have full text access to this OnlineOpen article
      Soft-Surface DNA Nanotechnology: DNA Constructs Anchored and Aligned to Lipid Membrane (pages 8312–8315)

      Dr. Karl Börjesson, Erik P. Lundberg, Jakob G. Woller, Prof. Bengt Nordén and Prof. Bo Albinsson

      Version of Record online: 14 JUL 2011 | DOI: 10.1002/anie.201103338

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      No strings attached: At least three attachment points are needed to align a two-dimensional DNA nanoconstruct to a soft lipid membrane surface with a porphyrin nucleoside as membrane anchor (see picture). The resulting freely diffusing DNA constructs can be reversibly assembled on the surface thus enabling the possibility of a self-repairing system.

    13. Radical Reactions

      Synthesis of Angularly Fused Aromatic Compounds from Alkenyl Enediynes by a Tandem Radical Cyclization Process (pages 8316–8319)

      Dr. Snigdha Roy, Prof. Anakuthil Anoop, Prof. Kumar Biradha and Prof. Amit Basak

      Version of Record online: 21 JUL 2011 | DOI: 10.1002/anie.201103318

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      Let's get radical: A general synthetic route toward angularly ortho-fused polyaromatic [4]helicenes starting from aryl alkenyl N-substituted cyclic enediynes is described (see scheme; DMSO=dimethyl sulfoxide, Ns=4-nitrobenzenesulfonyl). The process involved a Bergman cyclization (BC) as the key step of an unprecedented tandem radical reaction.

    14. Gold Chemistry

      Spontaneous Oxidative Addition of σ-Si[BOND]Si Bonds at Gold (pages 8320–8324)

      Pauline Gualco, Dr. Sonia Ladeira, Dr. Karinne Miqueu, Dr. Abderrahmane Amgoune and Dr. Didier Bourissou

      Version of Record online: 19 JUL 2011 | DOI: 10.1002/anie.201103719

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      Gold can do it! The activation of disilanes at gold was observed experimentally and analyzed theoretically. Upon chelation with two or even only one phosphine donor, the oxidative addition of σ-Si[BOND]Si bonds proceeds readily at low temperatures. These results show an unexpected similarity between gold and the other late transition metals towards σ bond activation.

    15. Amination Reactions

      Titanium-Mediated Amination of Grignard Reagents Using Primary and Secondary Amines (pages 8325–8328)

      Timothy J. Barker and Prof. Elizabeth R. Jarvo

      Version of Record online: 18 JUL 2011 | DOI: 10.1002/anie.201103700

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      Make it, then break it: N-chlorosuccinimide (NCS) was employed as the oxidant in the synthesis of aniline derivatives using the title transformation (see scheme). Functionalization was well tolerated on both the amine and Grignard reagent. An androgen receptor agonist and several analogues were synthesized to demonstrate the utility of this method.

    16. Glycosylation

      Characterization of the Isochromen-4-yl-gold(I) Intermediate in the Gold(I)-Catalyzed Glycosidation of Glycosyl ortho-Alkynylbenzoates and Enhancement of the Catalytic Efficiency Thereof (pages 8329–8332)

      Yugen Zhu and Prof. Biao Yu

      Version of Record online: 20 JUL 2011 | DOI: 10.1002/anie.201103409

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      Gold standard: The title gold complex (see scheme) was characterized unambiguously as an important intermediate in the title reaction. Protonolysis of this vinyl gold(I) complex was critical for regeneration of the active gold(I) species for the catalytic cycle, and use of a protic acid co-catalyst significantly lowered the required catalyst loading to 0.5 mol %.

    17. Protein Probes

      Cyano Groups as Probes of Protein Microenvironments and Dynamics (pages 8333–8337)

      Dr. Jörg Zimmermann, Megan C. Thielges, Dr. Young Jun Seo, Prof. Philip E. Dawson and Prof. Floyd E. Romesberg

      Version of Record online: 20 JUL 2011 | DOI: 10.1002/anie.201101016

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      Probe probation: The cyano group is sensitive to its environment, absorbs in a unique region of protein IR spectra, and may be appended to an amino acid. When investigated in variants of cytochrome c (see picture: heme-pocket structure) by steady-state and time-resolved methods, it was found to be a useful site-specific probe of protein microenvironments and dynamics; however, it can also perturb its environment and destabilize the folded state of the protein.

    18. Alkyne Activation

      Catalytic Synthesis of Nonracemic Azaproline Derivatives by Cyclization of β-Alkynyl Hydrazines under Kinetic Resolution Conditions (pages 8338–8341)

      Pradip Maity and Prof. Salvatore D. Lepore

      Version of Record online: 15 JUL 2011 | DOI: 10.1002/anie.201101090

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      No metals required: Starting from readily accessible γ-silyl allenyl esters, β-alkynyl hydrazines were prepared in one step and subsequently cyclized in the presence of ammonium and phosphonium catalysts leading to dehydroazaproline products (see scheme; X=O, S). These heterocycles were also produced in high enantiomeric excesses using chiral ammonium phase-transfer catalysts by a kinetic resolution.

    19. Host–Guest Chemistry

      Size-Selective Encapsulation of C60 by [10]Cycloparaphenylene: Formation of the Shortest Fullerene-Peapod (pages 8342–8344)

      Takahiro Iwamoto, Yoshiki Watanabe, Tatsuya Sadahiro, Prof. Takeharu Haino and Prof. Shigeru Yamago

      Version of Record online: 18 JUL 2011 | DOI: 10.1002/anie.201102302

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      For sorting peas: When a mixture of cycloparaphenylenes (CPPs) is treated with C60, [10]CPP selectively encapsulates C60 forming the shortest fullerene-peapod, [10]CPP⊃C60 (see picture). Such complementary host–guest complexes could be useful for the size- and shape-selective separation of higher fullerenes and carbon nanotubes.

    20. Dynamic Covalent Chemistry

      Self-Sorting of Dynamic Imine Libraries during Distillation (pages 8345–8349)

      Dr. Karolina Osowska and Prof. Ognjen Š. Miljanić

      Version of Record online: 15 JUL 2011 | DOI: 10.1002/anie.201102813

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      Keep it simple: The reaction of n aldehydes with n amines leads to a dynamic library of [n×n] imines. Slow distillation of the library amplifies the most volatile imine, whereby the most volatile aldehyde and amine are extracted from all other library components. Iterative repetition of the process enabled the self-sorting of the dynamic library into n mechanically separated imines, which were obtained in high yield.

    21. Natural Product Synthesis

      Total Synthesis of Paecilospirone (pages 8350–8353)

      Tsz-Ying Yuen, Sung-Hyun Yang and Prof. Dr. Margaret A. Brimble

      Version of Record online: 20 JUL 2011 | DOI: 10.1002/anie.201103117

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      Neutrality is the best policy: Key features of the first total synthesis of paecilospirone include an anti-selective, lactate-derived aldol reaction, and a double deallylation/spirocyclization conducted at neutral pH to construct the sensitive hydroxy-substituted benzannulated spiroacetal (see scheme; Bn=benzyl, TBS=tert-butyldimethylsilyl, TES=triethylsilyl).

    22. Main-Group Compounds

      Trapping the Parent Inorganic Ethylenes H2SiGeH2 and H2SiSnH2 in the Form of Stable Adducts at Ambient Temperature (pages 8354–8357)

      S. M. Ibrahim Al-Rafia, Adam C. Malcolm, Dr. Robert McDonald, Dr. Michael J. Ferguson and Prof. Dr. Eric Rivard

      Version of Record online: 19 JUL 2011 | DOI: 10.1002/anie.201103576

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      Putting on some weight: A series of stable adducts featuring the hitherto unknown mixed heavy ethylene analogues H2SiGeH2 and H2SiSnH2 (see picture) were prepared using a versatile donor–acceptor method.

    23. Heterocycles

      Umpolung Reactivity of Indole through Gold Catalysis (pages 8358–8362)

      Dr. Biao Lu, Yingdong Luo, Dr. Lianzhu Liu, Dr. Longwu Ye, Yanzhao Wang and Prof. Dr. Liming Zhang

      Version of Record online: 14 JUL 2011 | DOI: 10.1002/anie.201103014

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      Electrophilic indole? Indoles, which are typically nucleophilic, can be made electrophilic through gold catalysis. By using an ortho-azido group to deliver a nitrene intramolecularly, an arylalkyne is converted into a gold carbene intermediate containing an indole skeleton that is highly electrophilic at the 3-position. A range of functionalized indoles is readily accessed by utilizing this strategy.

    24. Borylation

      Palladium-Catalyzed Borylation of Sterically Demanding Aryl Halides with a Silica-Supported Compact Phosphane Ligand (pages 8363–8366)

      Soichiro Kawamorita, Prof. Dr. Hirohisa Ohmiya, Dr. Tomohiro Iwai and Prof. Dr. Masaya Sawamura

      Version of Record online: 12 JUL 2011 | DOI: 10.1002/anie.201103224

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      Immobile but active: A silica-supported “compact” phosphane, Silica-SMAP, can be used in the Pd-catalyzed borylation of aryl chlorides or bromides with bis(pinacolato)diboron (see scheme). The Silica-SMAP/Pd system significantly expands the substrate scope of the borylation toward sterically and electronically challenging aryl halides.

    25. NMR Spectroscopy

      Beyond the Silica Surface by Direct Silicon-29 Dynamic Nuclear Polarization (pages 8367–8370)

      Dr. Olivier Lafon, Dr. Melanie Rosay, Dr. Fabien Aussenac, Xingyu Lu, Dr. Julien Trébosc, Dr. Odile Cristini, Dr. Christophe Kinowski, Nadia Touati, Dr. Hervé Vezin and Prof. Jean-Paul Amoureux

      Version of Record online: 18 JUL 2011 | DOI: 10.1002/anie.201101841

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      Buried truth: High-field magic angle spinning dynamic nuclear polarization (MAS DNP) enhances the sensitivity of solid-state NMR spectroscopy, but only for protonated surfaces. Direct 29Si DNP using the biradical TOTAPOL (see picture) circumvents this limitation by producing a 30-fold enhancement of subsurface 29Si NMR signals in mesoporous silica, a material with applications in photonics, nanotechnology and catalysis.

    26. Isomerization

      Metastable Linkage Isomerism in [Ni(Et4dien)(NO2)2]: A Combined Thermal and Photocrystallographic Structural Investigation of a Nitro/Nitrito Interconversion (pages 8371–8374)

      Lauren E. Hatcher, Mark R. Warren, Dr. David R. Allan, Dr. Simon K. Brayshaw, Dr. Andrew L. Johnson, Dr. Sara Fuertes, Dr. Stefanie Schiffers, Anna J. Stevenson, Dr. Simon J. Teat, Christopher H. Woodall and Prof. Paul R. Raithby

      Version of Record online: 20 JUL 2011 | DOI: 10.1002/anie.201102022

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      One way or another: The N-bound NO2 group in [Ni(Et4dien)(η2-O,ON)(η1-NO2)] (see structure Ni turquoise, N blue, O red) has been shown to undergo reversible conversion into the O-bound nitrito linkage isomer under both thermal and photoactivation of a single crystal. Et4dien=N,N,N′,N′-tetraethyldiethylenetriamine.

    27. Metal Anionic Crowns

      You have full text access to this OnlineOpen article
      Mixed Lithium Amide–Lithium Halide Compounds: Unusual Halide-Deficient Amido Metal Anionic Crowns (pages 8375–8378)

      Dr. Alan R. Kennedy, Prof. Robert E. Mulvey, Dr. Charles T. O'Hara, Gemma M. Robertson and Dr. Stuart D. Robertson

      Version of Record online: 19 JUL 2011 | DOI: 10.1002/anie.201102023

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      Molecular salt cellars: The addition of substoichiometric quantities of lithium halides to the lithium hexamethyldisilazide was studied. Surprisingly, a novel class of mixed amido-halide macrocyclic complexes, namely metal anionic crowns (MACs) was revealed (see picture: Li pink, N yellow, Cl green, Si orange, C black).

    28. High-Spin Non-Heme Iron Complex

      C[BOND]H Bond Activation of Methanol and Ethanol by a High-Spin FeIVO Biomimetic Complex (pages 8379–8383)

      Dr. William A. Donald, Prof. Christine J. McKenzie and Prof. Richard A. J. O'Hair

      Version of Record online: 29 JUN 2011 | DOI: 10.1002/anie.201102146

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      C[BOND]H vs O[BOND]H vs C[BOND]O bond activation? The non-heme complex [(bpg)FeIVO]+ activates the αC[BOND]H bond of primary alcohols in vacuum through H abstraction by the FeO group in the rate-determining step. Although this effect counteracts any enhancement of reactivity that results from increasing the formal oxidation state of Fe, it increases the reaction selectivity.

    29. Dynamic Combinatorial Chemistry

      Hydrogel Formation upon Photoinduced Covalent Capture of Macrocycle Stacks from Dynamic Combinatorial Libraries (pages 8384–8386)

      Jianwei Li, Dr. Jacqui M. A. Carnall, Dr. Marc C. A. Stuart and Dr. Sijbren Otto

      Version of Record online: 14 JUL 2011 | DOI: 10.1002/anie.201103297

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      Stacks of macrocycles, assembled using reversible disulfide-bond formation, are covalently captured by photoinitiated exchange of disulfide bonds, inducing the formation of hydrogels (see picture). This strategy allows access to structures beyond the thermodynamic minima traditionally targeted by dynamic combinatorial chemistry.

    30. Biocatalysis

      Dynamic Kinetic Resolution of α-Substituted β-Ketoesters Catalyzed by Baeyer–Villiger Monooxygenases: Access to Enantiopure α-Hydroxy Esters (pages 8387–8390)

      Ana Rioz-Martínez, Aníbal Cuetos, Dr. Cristina Rodríguez, Dr. Gonzalo de Gonzalo, Dr. Iván Lavandera, Prof. Dr. Marco W. Fraaije and Prof. Vicente Gotor

      Version of Record online: 15 JUL 2011 | DOI: 10.1002/anie.201103348

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      BVMOs make a play: The dynamic kinetic resolution of racemic α-alkyl-β-ketoesters was performed through a selective Baeyer–Villiger oxidation employing different Baeyer–Villiger monooxygenases (BVMOs) in mild basic media. The product diesters were obtained with excellent yields and enantioselectivities, and used as precursors for optically active α-hydroxy esters.

    31. Reaction Design

      Cyclopropyl Iminium Activation: Reactivity Umpolung in Enantioselective Organocatalytic Reaction Design (pages 8391–8395)

      Christof Sparr and Prof. Dr. Ryan Gilmour

      Version of Record online: 22 JUL 2011 | DOI: 10.1002/anie.201103360

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      Trick the iminium! The concept of cyclopropyl iminium activation for the organocatalytic desymmetrization of meso-cyclopropylcarbaldehydes is presented. A combination of nucleophilic and electrophilic chlorinating reagents leads to a formal addition of Cl2 across one of the cyclopropyl bonds giving access to 1,3-dichlorides in an enantioselective, catalytic fashion.

    32. CO2 Reduction

      Stoichiometric Reduction of CO2 to CO by Aluminum-Based Frustrated Lewis Pairs (pages 8396–8399)

      Gabriel Ménard and Prof. Dr. Douglas W. Stephan

      Version of Record online: 14 JUL 2011 | DOI: 10.1002/anie.201103600

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      Reducing frustration: The reaction of Mes3P(CO2)(AlI3)2 in the presence of a CO2 atmosphere results in the formation of Mes3P(CO2)(O(AlI2)2)(AlI3) and [Mes3PI][AlI4] (Mes=2,4,6-Me3C6H2) with the evolution of CO.

    33. Borenium Cations

      Synthesis, Structure, and Reactivity of a Dihydrido Borenium Cation (pages 8400–8403)

      Dr. Blanca Inés, Dr. Mahendra Patil, Dr. Javier Carreras, Dr. Richard Goddard, Prof. Dr. Walter Thiel and Dr. Manuel Alcarazo

      Version of Record online: 14 JUL 2011 | DOI: 10.1002/anie.201103197

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      Bottled! The employment of hexaphenylcarbodiphosphorane as ancillary ligand has allowed the isolation of the otherwise transient dihydrido borenium cation.

    34. Total Synthesis

      Asymmetric Allylboration of vic-Tricarbonyl Compounds: Total Synthesis of (+)-Awajanomycin (pages 8404–8406)

      Dipl.-Chem. Malte Wohlfahrt, Dr. Klaus Harms and Prof. Dr. Ulrich Koert

      Version of Record online: 14 JUL 2011 | DOI: 10.1002/anie.201103679

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      To the core: An efficient total synthesis of (+)-awajanomycin was achieved starting with an asymmetric allylboration of a vic-tricarbonyl compound (see scheme; TES=triethylsilyl). A stereoselective alkene dihydroxylation followed by a differentiation of diastereotopic ester groups and a subsequent lactamization gave the bicyclic core structure.

      Corrected by:

      Corrigendum: Corrigendum: Asymmetric Allylboration of vic-Tricarbonyl Compounds: Total Synthesis of (+)-Awajanomycin

      Vol. 50, Issue 46, 10756, Version of Record online: 9 NOV 2011

    35. Neurosteroids

      Synthesis of Withanolide A, Biological Evaluation of Its Neuritogenic Properties, and Studies on Secretase Inhibition (pages 8407–8411)

      Dr. Chandan Kumar Jana, Johannes Hoecker, Dr. Tom M. Woods, Dr. Henning J. Jessen, Markus Neuburger and Prof. Dr. Karl Gademann

      Version of Record online: 15 JUL 2011 | DOI: 10.1002/anie.201101869

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      Neurons on steroids: A stereoselective synthesis of the neuritogenic steroid lactone withanolide A was achieved by singlet oxygen ene reaction, Wharton transposition, a Corey–Seebach homologation, and a vinylogous aldol reaction. Biological evaluation demonstrated neurite outgrowth, which supports the potential neuritogenic role of this compound in traditional Indian medicine.

    36. Organocatalysis

      N-Heterocyclic Carbene Catalyzed Umpolung of Michael Acceptors for Intermolecular Reactions (pages 8412–8415)

      Dr. Akkattu T. Biju, Mohan Padmanaban, Nathalie E. Wurz and Prof. Dr. Frank Glorius

      Version of Record online: 21 JUL 2011 | DOI: 10.1002/anie.201103555

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      leahciM! The N-heterocyclic carbene catalyzed umpolung of Michael acceptors proceeds through the formation of a deoxy-Breslow intermediate (see scheme; EWG=electron-withdrawing group). This nucleophilic species can react with other Michael acceptors in an intermolecular fashion, thereby resulting in the formation of homo- or heterodimeric olefins. This “Michael umpolung” should become a valuable method for the formation of densely functionalized olefins.

    37. Photochemistry

      Intramolecular [2+2] Photocycloaddition of Substituted Isoquinolones: Enantioselectivity and Kinetic Resolution Induced by a Chiral Template (pages 8416–8419)

      Dr. Kerrie A. B. Austin, Dr. Eberhardt Herdtweck and Prof. Dr. Thorsten Bach

      Version of Record online: 19 JUL 2011 | DOI: 10.1002/anie.201103051

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      From simple to complex: Starting from easily accessible isoquinolones 1 (X=Br, OH), complex cyclobutane photoproducts such as compound 2 can be obtained with high enantioselectivity (88–96 % ee) through the use of a chiral template. Compound 3, which was isolated in 53 % ee starting from a racemic substrate, is the product of a unique, unprecedented kinetic resolution process.

    38. Low-Valent Phosphorus

      Phosphination of Carbon Monoxide: A Simple Synthesis of Sodium Phosphaethynolate (NaOCP) (pages 8420–8423)

      Dr. Florian Frank Puschmann, Dr. Daniel Stein, Dominikus Heift, Coenradus Hendriksen, Dr. Zoltan A. Gal, Prof. Dr. Hans-Friedrich Grützmacher and Prof. Dr. Hansjörg Grützmacher

      Version of Record online: 15 JUL 2011 | DOI: 10.1002/anie.201102930

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      Simple basic ingredients are at the origin of the synthesis of Na(O[BOND]C[TRIPLE BOND]P), the phosphorus analogue of sodium cyanate. Na(O[BOND]C[TRIPLE BOND]P) is obtained from NaPH2 (made from Na, P, and a proton source) and CO (from carbon and air). This salt is remarkably stable, in complete contrast to H[BOND]C[TRIPLE BOND]P discovered 50 years ago.

    39. High-Density Cell Microarrays

      Superhydrophobic–Superhydrophilic Micropatterning: Towards Genome-on-a-Chip Cell Microarrays (pages 8424–8427)

      Florian L. Geyer, Erica Ueda, Dr. Urban Liebel, Dr. Nicole Grau and Dr. Pavel A. Levkin

      Version of Record online: 12 JUL 2011 | DOI: 10.1002/anie.201102545

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      High-density cell microarrays based on superhydrophilic microspots separated by superhydrophobic barriers have been realized. The microspots absorb water solutions, while the barriers prevent cross-contamination, thus allowing the spots to be used as reservoirs for transfection mixtures and preventing cell proliferation and cell migration between the microspots. The picture shows four cell types after two days of culturing on the microarray.

    40. Chemical Glycobiology

      Mechanism of Multivalent Carbohydrate–Protein Interactions Studied by EPR Spectroscopy (pages 8428–8431)

      Dipl.-Chem. Patrick Braun, M. Sc. Bettina Nägele, Prof. Dr. Valentin Wittmann and Dr. Malte Drescher

      Version of Record online: 7 JUL 2011 | DOI: 10.1002/anie.201101074

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      From a distance: Distance measurements in the nanometer range by means of spin-label electron paramagnetic resonance provide structural evidence for multivalent protein–ligand interactions in solution (see picture; protein subunits: blue/green, ligand: black, spin labels: yellow circles, binding sites: yellow letters). The data show a detailed picture of the binding of divalent ligands to a lectin.

    41. Membrane Protein Structure

      The Conformation of Bacteriorhodopsin Loops in Purple Membranes Resolved by Solid-State MAS NMR Spectroscopy (pages 8432–8435)

      Dr. Victoria A. Higman, Dr. Krisztina Varga, Dr. Lubica Aslimovska, Dr. Peter J. Judge, Lindsay J. Sperling, Prof. Chad M. Rienstra and Prof. Anthony Watts

      Version of Record online: 18 JUL 2011 | DOI: 10.1002/anie.201100730

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      Making complements: Solid-state MAS NMR spectra of bacteriorhodopsin in its native purple membrane environment can be used to complement crystallographic studies of the protein by validating and redefining the (possibly distorted) loop structures. Backbone dihedral angles were extracted from the chemical shifts and compared to the crystal structures. Where there are conformational differences, the dihedral angles were used to recalculate the loop structure (see picture).

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