Angewandte Chemie International Edition

Cover image for Vol. 51 Issue 22

May 29, 2012

Volume 51, Issue 22

Pages 5259–5504

  1. Cover Picture

    1. Top of page
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    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Editorial
    7. Graphical Abstract
    8. Corrigendum
    9. News
    10. Author Profile
    11. Obituary
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
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    1. Cover Picture: Discovery and Target Identification of an Antiproliferative Agent in Live Cells Using Fluorescence Difference in Two-Dimensional Gel Electrophoresis (Angew. Chem. Int. Ed. 22/2012) (page 5259)

      Jongmin Park, Dr. Sangmi Oh and Prof. Seung Bum Park

      Article first published online: 5 APR 2012 | DOI: 10.1002/anie.201202174

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      Target identification is the crown jewel of chemical biology. In their Communication on page 5447 ff., S. B. Park et al. have developed a new target identification method, fluorescence difference in two-dimensional gel electrophoresis (FITGE), to observe the interactions between proteins and small molecules in an intact cellular environment. FITGE successfully identifies protein differentiation between specific and nonspecific binding of photoaffinity probes.

  2. Inside Cover

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    5. Back Cover
    6. Editorial
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    8. Corrigendum
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    11. Obituary
    12. Book Review
    13. Highlights
    14. Minireview
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    1. Inside Cover: Definitive Evidence for Fast Electron Transfer at Pristine Basal Plane Graphite from High-Resolution Electrochemical Imaging (Angew. Chem. Int. Ed. 22/2012) (page 5260)

      Dr. Stanley C. S. Lai, Anisha N. Patel, Kim McKelvey and Prof. Dr. Patrick R. Unwin

      Article first published online: 3 MAY 2012 | DOI: 10.1002/anie.201203011

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      The electroactivity of basal plane graphite has been measured for the first time without interference from intersecting step edges by using high-resolution scanning electrochemical cell microscopy. In their Communication on page 5405 ff., P. R. Unwin et al. provide definitive evidence for fast and uniform electron transfer at basal plane graphite, and demonstrate the need for revision of current models for the electroactivity of graphite and related sp2 carbon materials. Illustration by Dr. Massimo Peruffo.

  3. Inside Back Cover

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    6. Editorial
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    8. Corrigendum
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    11. Obituary
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    13. Highlights
    14. Minireview
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    1. Inside Back Cover: A Small Molecule that Walks Non-Directionally Along a Track Without External Intervention (Angew. Chem. Int. Ed. 22/2012) (page 5505)

      Dr. Araceli G. Campaña, Dr. Armando Carlone, Dr. Kai Chen, Dr. David T. F. Dryden, Prof. David A. Leigh, Urszula Lewandowska and Dr. Kathleen M. Mullen

      Article first published online: 3 MAY 2012 | DOI: 10.1002/anie.201203119

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      Walking along a track is no problem for a small molecule, as described by D. A. Leigh et al. in their Communication on page 5480 ff. The synthetic small molecule walks through successive Michael/retro-Michael reactions and ultimately performs a task, namely quenching the fluorescence of an anthracene group at one end of the track.

  4. Back Cover

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    11. Obituary
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
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    1. Back Cover: Reactivity of Atmospherically Relevant Small Radicals at the Air–Water Interface (Angew. Chem. Int. Ed. 22/2012) (page 5506)

      Dr. Marilia T. C. Martins-Costa, Dr. Josep M. Anglada, Prof. Joseph S. Francisco and Dr. Manuel F. Ruiz-Lopez

      Article first published online: 26 APR 2012 | DOI: 10.1002/anie.201202657

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      Chemistry at the air–water interface of atmospherically relevant radicals is different from both the bulk and the gas phase. In their Communication on page 5413 ff., M. F. Ruiz-López and co-workers carried out computer simulations on HO2. and O2.− radicals. The effective ionic dissociation constant of the HO2. radical and the redox potential of the O2.− radical are lower at the interface than in the bulk.

  5. Editorial

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    12. Book Review
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    14. Minireview
    15. Review
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  6. Graphical Abstract

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    1. Graphical Abstract: Angew. Chem. Int. Ed. 22/2012 (pages 5265–5277)

      Article first published online: 23 MAY 2012 | DOI: 10.1002/anie.201290040

  7. Corrigendum

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      Corrigendum: A Genetically Encoded Norbornene Amino Acid for the Mild and Selective Modification of Proteins in a Copper-Free Click Reaction (page 5277)

      Dipl.-Ing. Emine Kaya, Dr. Milan Vrabel, M. Sc. Christian Deiml, M. Sc. Stefan Prill, Dr. Viviana S. Fluxa and Prof. Dr. Thomas Carell

      Article first published online: 23 MAY 2012 | DOI: 10.1002/anie.201203209

      This article corrects:
  8. News

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  9. Author Profile

    1. Top of page
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    1. Matthias Beller (pages 5284–5285)

      Article first published online: 26 APR 2012 | DOI: 10.1002/anie.201201343

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      “When I was eighteen I wanted to be a biology and chemistry teacher. The biggest challenge facing scientists is the development of technologies and methods to secure a sustainable future for our children …” This and more about Matthias Beller can be found on page 5284.

  10. Obituary

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    1. Howard E. Zimmerman (1926–2012) (pages 5286–5288)

      David I. Schuster

      Article first published online: 8 MAY 2012 | DOI: 10.1002/anie.201202970

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  11. Book Review

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    1. Heterogeneous Catalysis. Fundamentals and Applications. By Julian R. H. Ross. (page 5289)

      Wolfgang Grünert

      Article first published online: 26 APR 2012 | DOI: 10.1002/anie.201201868

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      Elsevier, Amsterdam, 2012. 232 pp., hardcover, € 110.00.—ISBN 978-0444533630

  12. Highlights

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    1. Organocatalysis

      Extending the Aminocatalytic HOMO-Raising Activation Strategy: Where Is the Limit? (pages 5290–5292)

      Dr. Elena Arceo and Prof. Dr. Paolo Melchiorre

      Article first published online: 4 APR 2012 | DOI: 10.1002/anie.201201347

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      Increasingly remote stereocenters are being targeted in asymmetric aminocatalysis. Application of the HOMO-raising activation concept to δ,δ-disubstituted 2,4-dienones confirms the powerful potential of the trienamine strategy. A cinchona-based primary amine catalyst enables the extension of this activation mode to a highly selective asymmetric Diels–Alder reaction of enones with electron-deficient dienophiles (see scheme; TFA: trifluoroacetic acid).

    2. Nanotechnology

      Dual-Responsive Boronate Crosslinked Micelles for Targeted Drug Delivery (pages 5293–5295)

      Weixuan Chen, Dr. Yunfeng Cheng and Prof. Dr. Binghe Wang

      Article first published online: 18 APR 2012 | DOI: 10.1002/anie.201201179

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      Controlled trigger finger: A novel class of micelles for targeted drug delivery was developed. The strategy relies on boronic acid–diol interactions as a way of accessing crosslinked micelles having improved stability (see scheme) and quick payload release in response to low pH environments or diol addition.

  13. Minireview

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    1. Nanochannels

      Building Bio-Inspired Artificial Functional Nanochannels: From Symmetric to Asymmetric Modification (pages 5296–5307)

      Dr. Xu Hou, Huacheng Zhang and Prof. Lei Jiang

      Article first published online: 13 APR 2012 | DOI: 10.1002/anie.201104904

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      Research on symmetric and asymmetric modifications of single nanochannels for building bio-inspired, artificial, functional nanochannels is a diverse field. By using track-etched polymer nanochannels with different shapes as an example, the feasibility and the design strategies for building such nanochannels by applying symmetric and asymmetric modifications is demonstrated. These modification techniques may also be extended to other materials.

  14. Review

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    1. Natural Products

      Curcumin—From Molecule to Biological Function (pages 5308–5332)

      Dr. Tuba Esatbeyoglu, Dr. Patricia Huebbe, Dr. Insa M. A. Ernst, M. Sc. Dawn Chin, Prof. Dr. Anika E. Wagner and Prof. Dr. Gerald Rimbach

      Article first published online: 4 MAY 2012 | DOI: 10.1002/anie.201107724

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      The spice of life: The main ingredient of the condiment and dye, turmeric, is “golden” curcumin (see structure). Recently, the beneficial health properties of curcuminoids have been increasingly discussed, since they induce endogenous antioxidant defense mechanisms in organisms, have anti-inflammatory effects, and modulate gene expression and epigenetic mechanisms.

  15. Communications

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    1. Chemical Sensing

      Bio-Inspired Nanostructured Sensor for the Detection of Ultralow Concentrations of Explosives (pages 5334–5338)

      Dr. Denis Spitzer, Dr. Thomas Cottineau, Dr. Nelly Piazzon, Dr. Sébastien Josset, Fabien Schnell, Dr. Sergey Nikolayevich Pronkin, Prof. Elena Romanovna Savinova and Dr. Valérie Keller

      Article first published online: 27 APR 2012 | DOI: 10.1002/anie.201108251

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      TNT: Silicon microcantilevers modified with a three-dimensional layer of vertical titanium dioxide nanotubes (see picture) can be used in micromechanical sensors with optical signal detection to detect low levels of explosives such as 2,4,6-trinitrotoluene (TNT) in the gas phase, even in the presence of other volatile impurities such as n-heptane and ethanol.

    2. Spectroscopic Analysis

      You have full text access to this OnlineOpen article
      Raman Spectroscopic Detection of Anthrax Endospores in Powder Samples (pages 5339–5342)

      S. Stöckel, S. Meisel, Dr. M. Elschner, Dr. P. Rösch and Prof. Dr. J. Popp

      Article first published online: 13 APR 2012 | DOI: 10.1002/anie.201201266

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      Better safe than sorry: A combined analytical procedure consisting of Raman spectroscopy and chemometrics can be used to test for anthrax endospores in environmental samples. Time-consuming enrichment steps are not required and low levels of anthrax endospores in household substances like baking powder can be detected within 3 h and discriminated against other nonpathogenic Bacillus species with typing accuracies of up to 99 %.

    3. Metal-Free Click Reaction

      Traceless Tosylhydrazone-Based Triazole Formation: A Metal-Free Alternative to Strain-Promoted Azide–Alkyne Cycloaddition (pages 5343–5346)

      Dr. Sander S. van Berkel, Dipl.-Chem. Sebastian Brauch, Lars Gabriel, Dipl.-Chem. Michael Henze, Dipl.-Chem. Sebastian Stark, Dipl.-Chem. Dimitar Vasilev, Prof. Dr. Ludger A. Wessjohann, Dr. Muhammad Abbas and Prof. Dr. Bernhard Westermann

      Article first published online: 18 APR 2012 | DOI: 10.1002/anie.201108850

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      Triple-T trick! Traceless tosylhydrazone-based triazole formation is readily achieved by reacting primary amines with functional α,α-dichlorotosylhydrozones under ambient conditions. This fast and efficient alternative affords exclusively 1,4-substituted triazole “click products” with complete retention of configuration. Primary amines, inherent to many natural products, can be modified in this way without protecting group manipulations.

    4. Metallacycloallenes

      Theoretical Evidence of the Stabilization of an Unusual Four-Membered Metallacycloallene by a Transition-Metal Fragment (pages 5347–5350)

      Subhendu Roy, Prof. Dr. Eluvathingal D. Jemmis, Prof. Dr. Axel Schulz, Dr. Torsten Beweries and Prof. Dr. Uwe Rosenthal

      Article first published online: 23 APR 2012 | DOI: 10.1002/anie.201200148

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      Connect five: Theoretical studies reveal that a Group 4 metal can significantly stabilize an unusual four-membered metallacycloallene. The role of the substituents R that donate two electrons to the complex is decisive. The systems contain an unprecedented crucial M[BOND]C bond in the MC3 ring (see scheme; Cp=cyclopentadienyl, NHC=N-heterocyclic carbene).

    5. Iron Carbene Catalysis

      Catalytic Activation of Diazo Compounds Using Electron-Rich, Defined Iron Complexes for Carbene-Transfer Reactions (pages 5351–5354)

      Dipl.-Chem. Michael S. Holzwarth, Isabel Alt and Prof. Dr. Bernd Plietker

      Article first published online: 11 APR 2012 | DOI: 10.1002/anie.201201409

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      Carbene transfer: The electron-rich iron complex Bu4N[Fe(CO)3(NO)] efficiently catalyzes different carbene-transfer reactions. Various diazo compounds can be used. The high stability of the employed iron complexes is demonstrated by the generation of the diazo reagent in situ and a sequential iron-catalyzed allylic sulfenylation/Doyle–Kirmse reaction.

    6. Continuous Asymmetric Synthesis

      Enantioselective β-Arylation of Ketones Enabled by Lithiation/Borylation/1,4-Addition Sequence Under Flow Conditions (pages 5355–5358)

      Dr. Wei Shu and Prof. Dr. Stephen L. Buchwald

      Article first published online: 18 APR 2012 | DOI: 10.1002/anie.201202221

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      The first multistep asymmetric catalysis in flow has been realized using a lithiation/borylation/rhodium-catalyzed 1,4-addition sequence. The three-step sequence starts from readily available and inexpensive aryl bromides, affording β-arylated ketones in good yields with high levels of enantioselectivity.

    7. C[BOND]H Activation

      Synthesis of Fluorene Derivatives through Rhodium-Catalyzed Dehydrogenative Cyclization (pages 5359–5362)

      Keisuke Morimoto, Masaki Itoh, Dr. Koji Hirano, Prof. Dr. Tetsuya Satoh, Yu Shibata, Prof. Dr. Ken Tanaka and Prof. Dr. Masahiro Miura

      Article first published online: 19 APR 2012 | DOI: 10.1002/anie.201201526

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      Doubling up: Two C[BOND]H bond activations took place efficiently upon treatment of 1 with a rhodium catalyst to form dehydrogenative cyclization products 2. Furthermore, 3 undergoes similar cyclization and subsequent decarboxylation through the cleavage of two C[BOND]H bonds and one C[BOND]C bond. Both reactions provide straightforward routes to the fluorene framework.

    8. Synthetic Methods

      N Alkylation of Tosylamides Using Esters as Primary and Tertiary Alkyl Sources: Mediated by Hydrosilanes Activated by a Ruthenium Catalyst (pages 5363–5366)

      Dr. Takashi Nishikata and Prof. Dr. Hideo Nagashima

      Article first published online: 19 APR 2012 | DOI: 10.1002/anie.201201426

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      Select your group: Either a primary or tertiary alkyl group can be selectively introduced onto the nitrogen atom of tosylamides in a ruthenium-catalyzed reaction employing hydrosilanes through a judicious choice in the esters that serve as the alkyl source (see scheme; Ts= 4-toluenesulfonyl). These N-alkylation reactions are useful for construction of naturally occurring azacyclic skeletons.

    9. Prins Cyclization of Bis(silyl) Homoallylic Alcohols to Form 2,6-cis-Tetrahydropyrans Containing a Geometrically Defined Exocyclic Vinylsilane: Efficient Synthesis of Ring B of the Bryostatins (pages 5367–5370)

      Ji Lu, Prof. Dr. Zhenlei Song, Yuebao Zhang, Zubao Gan and Hongze Li

      Article first published online: 13 APR 2012 | DOI: 10.1002/anie.201201323

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      Prins Charming: Prins cyclization of a bis(silyl) homoallylic alcohol with an aldehyde shows excellent cis and Z selectivity to form tetrahydropyrans containing a geometrically defined exocyclic vinylsilane. This reaction was used as the key step in the synthesis of ring B of the bryostatins.

    10. Protein Design

      Modular Assembly of RanBP2-Type Zinc Finger Domains to Target Single-Stranded RNA (pages 5371–5375)

      Mitchell R. O'Connell, Dr. Marylène Vandevenne, Cuong D. Nguyen, Prof. Jacqueline M. Matthews, Dr. Roland Gamsjaeger, Prof. David J. Segal and Prof. Joel P. Mackay

      Article first published online: 19 APR 2012 | DOI: 10.1002/anie.201200866

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      Fingering RNA: To study the function of the variety of RNA species that have been discovered recently, sequence-specific RNA-binding molecules with tunable specificity are required. Here, the use of zinc fingers (ZFs) from the splicing factors ZRANB2 and RBM5 as potential modules for the assembly of sequence-specific RNA-binding molecules is demonstrated.

    11. Bioinorganic Chemistry

      The Reaction of a High-Valent Nonheme Oxoiron(IV) Intermediate with Hydrogen Peroxide (pages 5376–5380)

      Joseph J. Braymer, Kevin P. O'Neill, Prof. Dr. Jan-Uwe Rohde and Prof. Dr. Mi Hee Lim

      Article first published online: 19 APR 2012 | DOI: 10.1002/anie.201200901

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      An FeIV[DOUBLE BOND]O group meets with H2O2! Reaction of high-valent iron with the reactive oxygen species (ROS) hydrogen peroxide (H2O2) is in general reserved for heme centers. Employing a biomimetic metal complex, the direct reaction of a mononuclear nonheme oxoiron(IV) species with H2O2 was observed and studied mechanistically, offering a new perspective for the chemistry between ROS and high-valent oxometal complexes.

    12. Organocatalysis

      Rationally Designed Amide Donors for Organocatalytic Asymmetric Michael Reactions (pages 5381–5385)

      Dr. Bin Tan, Dr. Gloria Hernández-Torres and Prof. Dr. Carlos F. Barbas III

      Article first published online: 13 APR 2012 | DOI: 10.1002/anie.201200996

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      Amide nucleophiles on demand: Rationally designed pyrazoleamides function as Michael donors in urea-catalyzed asymmetric Michael reactions with excellent chemical and optical yields (see scheme). The pyrazoleamide group performs as an ester equivalent, a directing group, an activating group, and functions as a good leaving group in further transformations of the product.

    13. Nitrogen Fixation

      Azo N[DOUBLE BOND]N Bond Cleavage with a Redox-Active Vanadium Compound Involving Metal–Ligand Cooperativity (pages 5386–5390)

      Carsten Milsmann, Zoë R. Turner, Scott P. Semproni and Prof. Paul J. Chirik

      Article first published online: 18 APR 2012 | DOI: 10.1002/anie.201201085

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      Coop mode: The reaction of azobenzene with a redox-active bis(imino)pyridine vanadium dinitrogen complex resulted in N[DOUBLE BOND]N bond cleavage and formation of the bis(imido) derivative (see picture). Similar reactivity was observed with O2 and S8 to yield the analogous terminal bis(oxides) and bis(sulfides), respectively. Studies of the electronic structure of the vanadium products show that bond cleavage involves reducing equivalents from the metal and the ligands.

    14. Natural Product Synthesis

      Diversity-Oriented Synthesis of Diverse Polycyclic Scaffolds Inspired by the Logic of Sesquiterpene Lactones Biosynthesis (pages 5391–5394)

      Dr. Gaëlle Valot, Dr. José Garcia, Vincent Duplan, Christelle Serba, Dr. Sofia Barluenga and Prof. Dr. Nicolas Winssinger

      Article first published online: 19 APR 2012 | DOI: 10.1002/anie.201201157

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      Natural selection: An acyclic chain containing an ene-yne-ene motif, in analogy to farnesyl diphosphate, was cyclized to obtain six distinct scaffolds using different transition-metal catalysts (see scheme). Notably, the guaianolide framework was accessed through enynene metathesis enabling the synthesis of three natural products.

    15. Homogeneous Catalysis

      Double Molecular Recognition with Aminoorganoboron Complexes: Selective Alcoholysis of β-Dicarbonyl Derivatives (pages 5395–5399)

      Shunsuke Oishi and Dr. Susumu Saito

      Article first published online: 13 APR 2012 | DOI: 10.1002/anie.201200304

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      Double duty: Aminoorganoboron (AOB) complexes recognize alcohol and β-dicarbonyl units, and thereby facilitate chemo- and site-selective alcoholysis of the latter (see scheme). The complex activates both reaction partners. This strategy enables C[BOND]C, C[BOND]N, and C[BOND]O bond cleavage in addition/elimination reactions under near neutral pH conditions and provides a new method for functional group conversions.

    16. Domino Reactions

      Rhodium(I)-Catalyzed Domino Asymmetric Ring Opening/Enantioselective Isomerization of Oxabicyclic Alkenes with Water (pages 5400–5404)

      Gavin C. Tsui and Prof. Dr. Mark Lautens

      Article first published online: 18 APR 2012 | DOI: 10.1002/anie.201200390

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      Water-induced asymmetric ring opening: Enantio-enriched 2-hydroxy-1-tetralones are formed from oxabicyclic alkenes through a novel RhI-catalyzed domino reaction. The proposed mechanism involves water-induced asymmetric ring opening to generate chiral trans-1,2-diol intermediates and subsequent enantioselective isomerization (see scheme).

    17. Electrochemical Imaging

      Definitive Evidence for Fast Electron Transfer at Pristine Basal Plane Graphite from High-Resolution Electrochemical Imaging (pages 5405–5408)

      Dr. Stanley C. S. Lai, Anisha N. Patel, Kim McKelvey and Prof. Dr. Patrick R. Unwin

      Article first published online: 5 APR 2012 | DOI: 10.1002/anie.201200564

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      After all, it's active: High-resolution scanning electrochemical cell microscopy (SECCM) demonstrates that electron transfer at the basal plane of highly oriented pyrolytic graphite (HOPG) is fast. This finding requires radical revision of the current textbook model for HOPG electrochemistry.

    18. Homogeneous Catalysis

      A Biologically Inspired CuI/Topaquinone-Like Co-Catalytic System for the Highly Atom-Economical Aerobic Oxidation of Primary Amines to Imines (pages 5409–5412)

      Dr. Martine Largeron and Prof. Dr. Maurice-Bernard Fleury

      Article first published online: 12 APR 2012 | DOI: 10.1002/anie.201200587

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      Acting together: Low catalytic amounts of CuI and topaquinone-like catalyst 1ox (see scheme) are sufficient to activate the α-C[BOND]H bond of primary amines, which are converted into alkylated imines under ambient conditions. This atom-economical process tolerates the presence of various reactive functional groups and allows selective cross-coupling of two amines.

    19. Atmospheric Chemistry

      Reactivity of Atmospherically Relevant Small Radicals at the Air–Water Interface (pages 5413–5417)

      Dr. Marilia T. C. Martins-Costa, Dr. Josep M. Anglada, Prof. Joseph S. Francisco and Dr. Manuel F. Ruiz-Lopez

      Article first published online: 21 MAR 2012 | DOI: 10.1002/anie.201200656

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      A fish out of water: The chemical properties at the air–water interface of the atmospherically important free radicals HO2. and O2.− were investigated by means of computer simulations. Acidity, HOMO–LUMO gap, and redox potentials differ from both the bulk and also the gas phase. These findings are significant for HO2. chemistry and aerosol and cloud chemistry.

    20. Surface Chemistry

      Flexible Nanogenerators Based on Graphene Oxide Films for Acoustic Energy Harvesting (pages 5418–5422)

      Dr. Ronghui Que, Qi Shao, Qinliang Li, Prof. Mingwang Shao, Shiduan Cai, Suidong Wang and Prof. Shuit-Tong Lee

      Article first published online: 18 APR 2012 | DOI: 10.1002/anie.201200773

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      Graphene oxide films were fabricated as low-cost and flexible nanogenerators to convert acoustic energy into electricity with a conversion efficiency of 12.1 % (see picture). The generated current sensitively depended on the pH value of the suspensions for graphene oxide (GO) film production.

    21. Asymmetric Catalysis

      Enantioselective Synthesis of α-Alkylidene-γ-Butyrolactones: Intramolecular Rauhut–Currier Reaction Promoted by Acid/Base Organocatalysts (pages 5423–5426)

      Dr. Shinobu Takizawa, Tue Minh-Nhat Nguyen, André Grossmann, Prof. Dr. Dieter Enders and Prof. Dr. Hiroaki Sasai

      Article first published online: 18 APR 2012 | DOI: 10.1002/anie.201201542

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      Teaming up: The title reaction has been developed to deliver the product α-alkylidene-γ-butyrolactones as single diastereomers with up to 98 % ee (see scheme; Ts=4-toluenesulfonyl). The enantioselective process is catalyzed by 1, which contains both Lewis base and Brønsted acid moieties.

    22. Oxygen Activation

      Structural and Spectroscopic Characterization of a Monomeric Side-On Manganese(IV) Peroxo Complex (pages 5427–5430)

      Prof. Chien-Ming Lee, Chi-He Chuo, Ching-Hui Chen, Prof. Cho-Chun Hu, Dr. Ming-Hsi Chiang, Yu-Jan Tseng, Prof. Ching-Han Hu and Dr. Gene-Hsiang Lee

      Article first published online: 18 APR 2012 | DOI: 10.1002/anie.201201735

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      Gotcha: The binding and activation of oxygen by a manganese complex is reported. A PS3 coordination sphere built around a manganese(I) center facilitates the isolation of a monomeric manganese(IV) peroxo complex that is stable at ambient temperature (see picture). The activation of molecular oxygen is proposed via a manganese(II) intermediate with an empty site for the binding of the substrate.

    23. Photoresponsive Molecules

      Turning “On” and “Off” a Pyridoxal 5′-Phosphate Mimic Using Light (pages 5431–5434)

      Danielle Wilson and Prof. Neil R. Branda

      Article first published online: 19 APR 2012 | DOI: 10.1002/anie.201201447

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      Light is used to toggle a photoresponsive mimic of the cofactor pyridoxal phosphate between two isomers, where only one of them can catalyze the racemization of an amino acid. The system is based on creating and breaking electronic communication between the two catalyst components, i.e., an aldehyde and a pyridinium cation.

    24. Transmetallation Reactions

      Exploiting Boron–Zinc Transmetallation for the Arylation of Benzyl Halides: What are the Reactive Species? (pages 5435–5438)

      Prof. Dr. Robin B. Bedford, Nicholas J. Gower, Dr. Mairi F. Haddow, Prof. Dr. Jeremy N. Harvey, Joshua Nunn, Rukeme A. Okopie and Dr. Rosalind F. Sankey

      Article first published online: 18 APR 2012 | DOI: 10.1002/anie.201202219

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      One step Beyond: The transmetallation reactions of ArB(OH)2 and Ar3B3O3 with Et2Zn are far more complicated than previously supposed, with solvent-dependent equilibria between ArB(OY)2 at one side and [RZn(solv)3][BR4] at the other (see picture). While the role of the highly reactive organozinc cation has not been implicated before, its importance for the activation of an otherwise sluggish class of electrophiles is shown.

    25. Biogenesis

      (IscS-IscU)2 Complex Structures Provide Insights into Fe2S2 Biogenesis and Transfer (pages 5439–5442)

      Dr. Elodie N. Marinoni, Dr. Jaim S. de Oliveira, Dr. Yvain Nicolet, Dr. Estella C. Raulfs, Dr. Patricia Amara, Prof. Dr. Dennis R. Dean and Dr. Juan C. Fontecilla-Camps

      Article first published online: 18 APR 2012 | DOI: 10.1002/anie.201201708

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      The center of attention: IscS cysteine desulfurases and IscU scaffolds are involved in biological iron–sulfur cluster assembly. The X-ray structure of an anaerobically produced, mutated (Fe2S2-(IscS-IscUD35A))2 complex reveals a cluster coordinated by three IscU cysteines and the IscS active cysteine (see picture). In air-exposed crystals the cluster is oxidized to an Fe2S–S center; D35 is essential for complex dissociation.

    26. Electrosynthesis

      Anodic Oxidation on a Boron-Doped Diamond Electrode Mediated by Methoxy Radicals (pages 5443–5446)

      Takenori Sumi, Dr. Tsuyoshi Saitoh, Keisuke Natsui, Dr. Takashi Yamamoto, Prof. Dr. Mahito Atobe, Prof. Dr. Yasuaki Einaga and Prof. Dr. Shigeru Nishiyama

      Article first published online: 18 APR 2012 | DOI: 10.1002/anie.201200878

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      Direct evidence: The existence of methoxy radical species formed during an anodic oxidation in MeOH on a boron-doped diamond (BDD) electrode was confirmed by ESR spectroscopy. Effective production of a neolignan, licarin A, was accomplished by the BDD-mediated anodic oxidation protocol (see picture).

    27. Target Identification in Live Cells

      Discovery and Target Identification of an Antiproliferative Agent in Live Cells Using Fluorescence Difference in Two-Dimensional Gel Electrophoresis (pages 5447–5451)

      Jongmin Park, Dr. Sangmi Oh and Prof. Seung Bum Park

      Article first published online: 4 APR 2012 | DOI: 10.1002/anie.201200609

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      Target acquired: Fluorescence difference in two-dimensional gel electrophoresis (FITGE) was developed to observe the interactions between proteins and small molecules in an intact cellular environment. FITGE proved effective over conventional methods by successfully identifying the protein target of an anti-proliferative compound in live cells through the differentiation between specific and extensive non-specific binding of photoaffinity probes.

    28. Click Chemistry

      Alternate Layered Nanostructures of Metal Oxides by a Click Reaction (pages 5452–5455)

      Dr. Dai Mochizuki, Kozue Kumagai, Dr. Masato M. Maitani and Prof. Yuji Wada

      Article first published online: 13 APR 2012 | DOI: 10.1002/anie.201200264

      Thumbnail image of graphical abstract

      Layer cake: Layered titanium and tungsten oxides modified by alkene and thiol groups, respectively, are exfoliated with organic solvent to form nanosheets, which are alternately stacked by a click reaction (see picture). The material enhances the photocatalytic decomposition of methylene blue.

    29. Organocatalysis

      A Microporous Binol-Derived Phosphoric Acid (pages 5456–5459)

      Dipti S. Kundu, Dr. Johannes Schmidt, Dr. Christian Bleschke, Prof. Dr. Arne Thomas and Prof. Dr. Siegfried Blechert

      Article first published online: 12 APR 2012 | DOI: 10.1002/anie.201109072

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      No slow down: A microporous recyclable heterogeneous catalyst made from a 1,1′-binaphthalene-2,2′-diol (binol)-derived phosphoric acid chloride is as active as the corresponding homogeneous catalyst when using the same mass of both in different reactions. Reaction rates, yields, and enantioselectivities are comparable.

    30. Nanotechnology

      Stimulated Release of Size-Selected Cargos in Succession from Mesoporous Silica Nanoparticles (pages 5460–5465)

      Dr. Cheng Wang, Zongxi Li, Dennis Cao, Dr. Yan-Li Zhao, Justin W. Gaines, Dr. O. Altan Bozdemir, Michael W. Ambrogio, Dr. Marco Frasconi, Dr. Youssry Y. Botros, Prof. Jeffrey I. Zink and Prof. J. Fraser Stoddart

      Article first published online: 13 APR 2012 | DOI: 10.1002/anie.201107960

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      Two birds with one stone: Covalent attachment of β-cyclodextrin rings (yellow; see figure) to mesoporous silica nanoparticles (MSNs) results in a dual-cargo release system into which differently sized cargos (blue and red spheres) can be loaded and then released in sequence when triggered by two different stimuli. The smaller molecules are released by lowering the pH value and the larger ones released after cleavage of the cyclodextrins from the MSN surface.

    31. DNA Damage

      Replication of N2,3-Ethenoguanine by DNA Polymerases (pages 5466–5469)

      Dr. Linlin Zhao, Dr. Plamen P. Christov, Dr. Ivan D. Kozekov, Dr. Matthew G. Pence, Dr. Pradeep S. Pallan, Prof. Dr. Carmelo J. Rizzo, Prof. Dr. Martin Egli and Prof. Dr. F. Peter Guengerich

      Article first published online: 4 APR 2012 | DOI: 10.1002/anie.201109004

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      Damaged goods: The unstable DNA adduct N2,3-ethenoguanine, a product of both exposure to the carcinogen vinyl chloride and of oxidative stress, was built into an oligonucleotide, using an isostere strategy to stabilize the glycosidic bond. This modification was then used to examine the cause of mutations by DNA polymerases, in terms of both the biochemistry of the lesion and a structure of the lesion within a polymerase (see scheme).

    32. Polyketides

      Assembly and Absolute Configuration of Short-Lived Polyketides from Burkholderia thailandensis (pages 5470–5474)

      Dr. Keishi Ishida, Thorger Lincke and Prof. Dr. Christian Hertweck

      Article first published online: 19 APR 2012 | DOI: 10.1002/anie.201200067

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      Decoded before decay: Cryptic and highly unstable polyketide metabolites, thailandamides A and B, were isolated from Burkholderia thailandensis, and their absolute configurations fully elucidated using a combination of chemical degradation, bioinformatics, NMR spectroscopy, precursor-directed biosynthesis, and analysis of pathway intermediates (see scheme).

    33. Hybrid Nanomaterials

      Hybrid Nanomaterials that Mimic the Food Effect: Controlling Enzymatic Digestion for Enhanced Oral Drug Absorption (pages 5475–5479)

      Dr. Angel Tan, Amanda Martin, Dr. Tri-Hung Nguyen, Prof. Ben J. Boyd and Prof. Clive A. Prestidge

      Article first published online: 13 APR 2012 | DOI: 10.1002/anie.201200409

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      Easily digested: SiO2–lipid hybrid microparticles with specific nanostructured interiors were generated from submicrometer-sized emulsion templates based on mesoporous and non-porous silica nanoparticles. These functional lipid-based microparticles can be used to mimic the pharmaceutical food effect and enhance drug absorption by controlling the enzymatic digestion of lipid colloids (see scheme; ○ oil solution, ▴ lipid–nanoparticle hybrid, □ lipid encapsulated in hybrid).

    34. Molecular Walkers

      A Small Molecule that Walks Non-Directionally Along a Track Without External Intervention (pages 5480–5483)

      Dr. Araceli G. Campaña, Dr. Armando Carlone, Dr. Kai Chen, Dr. David T. F. Dryden, Prof. David A. Leigh, Urszula Lewandowska and Dr. Kathleen M. Mullen

      Article first published online: 5 APR 2012 | DOI: 10.1002/anie.201200822

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      Charge of the light brigade: A molecule is able to walk back and forth upon a five-foothold pentaethylenimine track without external intervention. The 1D random walk is highly processive (mean step number 530) and exchange takes place between adjacent amine groups in a stepwise fashion. The walker performs a simple task whilst walking: quenching of the fluorescence of an anthracene group sited at one end of the track.

    35. Boron Heterocycles

      Electron-Donating Tetrathienyl-Substituted Borole (pages 5484–5487)

      Takafumi Araki, Dr. Aiko Fukazawa and Prof. Dr. Shigehiro Yamaguchi

      Article first published online: 12 APR 2012 | DOI: 10.1002/anie.201201156

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      Green borole debuts: A heteroaryl-substituted borole with peripheral thienyl groups has a significantly high-lying HOMO in addition to a low-lying LUMO, and thus unusual photophysical and electrochemical properties. These results highlight the highly electron-donating character of the borole ring.

    36. Surface Charges

      Probing the Charge Build-Up and Dissipation on Thin PMMA Film Surfaces at the Molecular Level by XPS (pages 5488–5492)

      Dr. Eda Yilmaz, Dr. Hikmet Sezen and Prof. Sefik Suzer

      Article first published online: 18 APR 2012 | DOI: 10.1002/anie.201201351

      Thumbnail image of graphical abstract

      What's the charge? X-ray photoelectron spectroscopy was used to determine the charge state and dynamics of charge build-up and decay on a thin poly(methyl methacrylate) film. The film is initially negatively charged to around −2 V and becomes progressively positively charged during the course of the XPS analysis.

    37. Printing of Stereocomplexes

      Rapid Fabrication of Polylactide Stereocomplex Using Layer-by-Layer Deposition by Inkjet Printing (pages 5493–5496)

      Dr. Takami Akagi, Dr. Tomoko Fujiwara and Prof. Mitsuru Akashi

      Article first published online: 18 APR 2012 | DOI: 10.1002/anie.201201586

      Thumbnail image of graphical abstract

      Jet set: Layer-by-layer alternate stepwise deposition of poly(L-lactide) (PLLA) and poly(D-lactide) (PDLA) is used to fabricate a polylactide (PLA) stereocomplex on a substrate (see picture). Multiple inkjet passes improve the crystal structure of the PLA composite without intermediate rinsing steps.

    38. Diagnostics

      Paper-Based Blood Typing Device That Reports Patient’s Blood Type “in Writing” (pages 5497–5501)

      Miaosi Li, Junfei Tian, Dr. Mohammad Al-Tamimi and Assoc. Prof. Wei Shen

      Article first published online: 18 APR 2012 | DOI: 10.1002/anie.201201822

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      A response in writing: A low-cost bioactive paper device is designed to perform ABO and RhD blood typing tests, and the paper reports the results in writing. This idea was inspired by the vision of the British author, J. K. Rowling, through her novel “Harry Potter and the Chamber of Secrets” in which a piece of paper could be interrogated for information and unambiguous answers were received from the paper in writing.

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      Article first published online: 23 MAY 2012 | DOI: 10.1002/anie.201290041

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