Angewandte Chemie International Edition

Cover image for Vol. 50 Issue 42

October 10, 2011

Volume 50, Issue 42

Pages 9759–9991

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. Corrigendum
    7. News
    8. Author Profile
    9. News
    10. Book Reviews
    11. Highlights
    12. Review
    13. Communications
    14. Preview
    1. Cover Picture: Bond Activation with an Apparently Benign Ethynyl Dithiocarbamate Ar[BOND]C[TRIPLE BOND]C[BOND]S[BOND]C(S)NR2 (Angew. Chem. Int. Ed. 42/2011) (page 9759)

      Gaël Ung, Dr. Guido D. Frey, Prof. Wolfgang W. Schoeller and Prof. Guy Bertrand

      Article first published online: 31 AUG 2011 | DOI: 10.1002/anie.201105306

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      A hedgehog molecule activates a variety of bonds. In their Communication on page 9923 ff., G. Bertrand et al. report that an ethynyl dithiocarbamate molecule, Ar[BOND]C[TRIPLE BOND]C[BOND]S[BOND]C(S)NR2 (hedgehog on the bottom left), is able to cleave a broad range of enthalpically strong σ bonds. The bond activation process involves either the existence of an equilibrium with the nonobservable cyclic mesoionic carbene isomer or the cooperation of the nucleophilic carbon–carbon triple bond and the electrophilic CS carbon atom, both leading to cyclic products (hedgehogs in the wheel).

  2. Inside Cover

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    4. Back Cover
    5. Graphical Abstract
    6. Corrigendum
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    8. Author Profile
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    10. Book Reviews
    11. Highlights
    12. Review
    13. Communications
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    1. Inside Cover: Magnesium-Mediated Benzothiazole Activation: A Room-Temperature Cascade of C[BOND]H Deprotonation, C[BOND]C Coupling, Ring-Opening, and Nucleophilic Addition Reactions (Angew. Chem. Int. Ed. 42/2011) (page 9760)

      Dr. Victoria L. Blair, Prof. William Clegg, Dr. Alan R. Kennedy, Zoe Livingstone, Dr. Luca Russo and Dr. Eva Hevia

      Article first published online: 31 AUG 2011 | DOI: 10.1002/anie.201105347

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      A special type of N-heterocycle activation promoted by a main-group compound is described by E. Hevia and co-workers in their Communication on page 9857 ff. Whereas previous organomagnesium reagents simply deprotonate benzothiazole, a new sodium magnesiate modification incorporating a bulky bis(amido) ligand initiates an unstoppable domino reaction that involves direct Mg[BOND]H exchange, C[BOND]C coupling, ring opening, nucleophilic addition, and intramolecular deprotonation of three molecules of benzothiazole at room temperature.

  3. Back Cover

    1. Top of page
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    4. Back Cover
    5. Graphical Abstract
    6. Corrigendum
    7. News
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    10. Book Reviews
    11. Highlights
    12. Review
    13. Communications
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    1. Back Cover: Development of Highly Cytotoxic and Actin-Depolymerizing Biotin Derivatives of Aplyronine A (Angew. Chem. Int. Ed. 42/2011) (page 9992)

      Dr. Masaki Kita, Yuichiro Hirayama, Miyuki Sugiyama and Prof. Dr. Hideo Kigoshi

      Article first published online: 5 SEP 2011 | DOI: 10.1002/anie.201106017

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      Aplyronine A is an antitumor macrolide from the sea hare Aplysia kurodai. In their Communication on page 9871 ff., H. Kigoshi and co-workers report the synthesis of a poly(ethylene glycol) (PEG)-linked derivative of aplyronine A, which exhibits potent cytotoxicity and can cause actin disassembly in tumor cells. Actin-related proteins as well as actin were specifically purified from cell lysate by using this probe.

  4. Graphical Abstract

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    10. Book Reviews
    11. Highlights
    12. Review
    13. Communications
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    1. Graphical Abstract: Angew. Chem. Int. Ed. 42/2011 (pages 9763–9775)

      Article first published online: 6 OCT 2011 | DOI: 10.1002/anie.201190087

  5. Corrigendum

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    1. You have free access to this content
      Corrigendum: Fused Indolines by Palladium-Catalyzed Asymmetric C[BOND]C Coupling Involving an Unactivated Methylene Group (page 9775)

      Dr. Masafumi Nakanishi, Dmitry Katayev, Dr. Céline Besnard and Prof. Dr. E. Peter Kündig

      Article first published online: 6 OCT 2011 | DOI: 10.1002/anie.201190088

      This article corrects:

      Fused Indolines by Palladium-Catalyzed Asymmetric C[BOND]C Coupling Involving an Unactivated Methylene Group1

      Vol. 50, Issue 32, 7438–7441, Article first published online: 1 JUL 2011

  6. News

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  7. Author Profile

    1. Top of page
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    5. Graphical Abstract
    6. Corrigendum
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    10. Book Reviews
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    1. Jun Okuda (page 9784)

      Article first published online: 14 SEP 2011 | DOI: 10.1002/anie.201104934

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      “In my opinion, the word “scientist” means being honest. My biggest motivation is understanding nature …” This and more about Jun Okuda can be found on page 9784.

  8. News

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    12. Review
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  9. Book Reviews

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    1. European Women in Chemistry. Edited by Jan Apotheker and Livia Simon Sarkadi. (page 9786)

      Kirsten Zeitler

      Article first published online: 16 SEP 2011 | DOI: 10.1002/anie.201104675

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      Wiley-VCH, Weinheim 2010. 256 pp., hardcover, € 24.90.—ISBN 978-3527329564

    2. Hydrogen and Fuel Cells. Fundamentals, Technologies and Applications. Edited by Detlev Stolten. (page 9787)

      Ludwig Jörissen

      Article first published online: 26 SEP 2011 | DOI: 10.1002/anie.201103583

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      Wiley-VCH, Weinheim 2010. 878 pp., hardcover, € 249.00.—ISBN 978-3527327119

  10. Highlights

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    1. Transcription

      Direct Observation of Single RNA Polymerase Processing through a Single Endogenous Gene in a Living Yeast Cell (pages 9788–9790)

      Barbara Treutlein and Prof. Dr. Jens Michaelis

      Article first published online: 26 JUL 2011 | DOI: 10.1002/anie.201103809

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      Rapid advances in live-cell imaging have now enabled direct observation of the transcription of single nascent mRNA molecules from an endogenous yeast gene. A novel quantitative fluctuation analysis of fluorescently labeled mRNA revealed the kinetics of transcription initiation and the dynamics of elongation and termination (see picture; GFP=green fluorescent protein, PP7 is a bacteriophage coat protein, RNAPII=RNA polymerase II, TF=transcription factor).

    2. B12-Radical Chemistry

      More Radical Magic with B12: B12-Catalyzed, Light-Induced Cleavage of DNA (pages 9791–9792)

      Prof. Dr. Bernhard Kräutler and Barbara Puffer

      Article first published online: 25 AUG 2011 | DOI: 10.1002/anie.201103373

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      B12in a new light: The B12 derivative hydroxocobalamin can be used as an efficient catalyst for light-induced strand cleavage of DNA. The proposed radical process involves hydroxy radicals and is controlled by visible light (see scheme). Such light-controlled radical reactions promise to be particularly useful in intracellular applications.

  11. Review

    1. Top of page
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    5. Graphical Abstract
    6. Corrigendum
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    8. Author Profile
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    11. Highlights
    12. Review
    13. Communications
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    1. Synthetic Methods

      Regio- and Chemoselective Metalation of Arenes and Heteroarenes Using Hindered Metal Amide Bases (pages 9794–9824)

      Dr. Benjamin Haag, Dr. Marc Mosrin, Prof. Dr. Hiriyakkanavar Ila, Dr. Vladimir Malakhov and Prof. Dr. Paul Knochel

      Article first published online: 27 SEP 2011 | DOI: 10.1002/anie.201101960

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      Valuable synthetic intermediates can be obtained by quenching with various electrophiles highly functionalized aryl-, heteroaryl-, and alkenylmetal compounds prepared by direct C[BOND]H activation using lithium chloride solubilized 2,2,6,6-tetramethylpiperidide bases, such as TMPMgCl⋅LiCl, TMPZnCl⋅LiCl, or TMP2Zn⋅2 LiCl, which tolerate a wide range of functional groups. The scope and limitations are given for each LiCl-solubilized base.

  12. Communications

    1. Top of page
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    5. Graphical Abstract
    6. Corrigendum
    7. News
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    12. Review
    13. Communications
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    1. Chemical Logic Gates

      From Virtual to Physical: Integration of Chemical Logic Gates (pages 9826–9831)

      Ruslan Guliyev, Seyma Ozturk, Ziya Kostereli and Prof. Dr. Engin U. Akkaya

      Article first published online: 25 AUG 2011 | DOI: 10.1002/anie.201104228

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      Integration by parts: Advanced information processing at the molecular level requires integrated logic gates, which has to date been possible only virtually. Now, two independently working AND molecular logic gates are brought together by “click” chemistry to form integrated logic gates which respond exactly as predicted from such an integration scheme (see picture, EET=excitation energy transfer).

    2. Enzyme Inhibition

      Development of Highly Potent Inhibitors of the Ras-Targeting Human Acyl Protein Thioesterases Based on Substrate Similarity Design (pages 9832–9837)

      Dr. Christian Hedberg, Dr. Frank J. Dekker, Dipl.-Chem. Marion Rusch, Dr. Steffen Renner, Dr. Stefan Wetzel, Dr. Nachiket Vartak, Dr. Claas Gerding-Reimers, Dr. Robin S. Bon, Prof. Dr. Philippe I. H. Bastiaens and Prof. Dr. Herbert Waldmann

      Article first published online: 9 SEP 2011 | DOI: 10.1002/anie.201102965

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      A matter of common sense: A common recognition motif consisting of a negatively charged group five to six bonds away (red) from the (thio)ester functionality (green) and a positively charged tail group ten to twelve bonds away (blue) was identified in two native acyl protein thioesterase 1 (APT1) substrates (see picture). This similarity led to the design of potent inhibitors of the Ras-depalmitoylating enzyme APT1.

    3. Identification of Acyl Protein Thioesterases 1 and 2 as the Cellular Targets of the Ras-Signaling Modulators Palmostatin B and M (pages 9838–9842)

      Dipl.-Chem. Marion Rusch, Dipl.-Chem. Tobias J. Zimmermann, M. Sc. Marco Bürger, Dr. Frank J. Dekker, Dr. Kristina Görmer, Dr. Gemma Triola, Andreas Brockmeyer, Dr. Petra Janning, Dr. Thomas Böttcher, Prof. Dr. Stephan A. Sieber, Dr. Ingrid R. Vetter, Dr. Christian Hedberg and Prof. Dr. Herbert Waldmann

      Article first published online: 9 SEP 2011 | DOI: 10.1002/anie.201102967

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      Finding the target: Activity-based proteomic profiling probes based on the depalmitoylation inhibitors palmostatin B and M (see picture) have been synthesized and were found to target acyl protein thioesterase 1 (APT1) and 2 (APT2) in cells.

    4. Natural Products

      Cytotoxic Pheofungins from an Engineered Fungus Impaired in Posttranslational Protein Modification (pages 9843–9847)

      Dr. Kirstin Scherlach, Hans-Wilhelm Nützmann, Dr. Volker Schroeckh, Dr. Hans-Martin Dahse, Prof. Dr. Axel A. Brakhage and Prof. Dr. Christian Hertweck

      Article first published online: 12 SEP 2011 | DOI: 10.1002/anie.201104488

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      What makes a fungus blush? The deletion of a gene that is required for global protein N-acetylation triggers the production of unprecedented metabolites in Aspergillus nidulans. The pronounced red pigmentation of the engineered mutant is caused by pheofungins (benzothiazinone chromophores, see scheme), the biogenesis of which is strikingly similar to those of pheomelanins found in red bird feathers and hair of Celtic origin.

    5. Conducting Materials

      Simultaneous Electronic and Ionic Conduction in a Block Copolymer: Application in Lithium Battery Electrodes (pages 9848–9851)

      Dr. Anna E. Javier, Shrayesh N. Patel, Dr. Daniel T. Hallinan Jr., Dr. Venkat Srinivasan and Prof. Nitash P. Balsara

      Article first published online: 7 SEP 2011 | DOI: 10.1002/anie.201102953

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      Charging ahead: Separate values for the simultaneous electronic and ionic conductivity of a conjugated polymer containing poly(3-hexylthiophene) and poly(ethylene oxide) (P3HT-PEO) were determined by using ac impedance and dc techniques. P3HT-PEO was used as binder, and transporter of electronic charge and Li+ ions in a LiFePO4 cathode, which was incorporated into solid-state lithium batteries (see picture; TFSI=bis(trifluoromethane sulfone)imide).

    6. Dual-Activity Polymers

      Synthetic Polymers for Simultaneous Bacterial Sequestration and Quorum Sense Interference (pages 9852–9856)

      Xuan Xue, Dr. George Pasparakis, Dr. Nigel Halliday, Dr. Klaus Winzer, Prof. Steven M. Howdle, Dr. Christopher J. Cramphorn, Prof. Neil R. Cameron, Dr. Paul M. Gardner, Prof. Benjamin G. Davis, Dr. Francisco Fernández-Trillo and Prof. Cameron Alexander

      Article first published online: 16 SEP 2011 | DOI: 10.1002/anie.201103130

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      Double agents: Dual-action polymers are able to sequester rapidly the marine organism Vibrio harveyi from suspension, while at the same time quenching bacterial quorum sense (QS) signals (see picture). The potency of the polymers is assessed by cell aggregation experiments and competitive binding assays against a QS signal precursor, and their effect on bacterial behavior is shown by means of bioluminescence.

    7. Mixed-Metal Chemistry

      Magnesium-Mediated Benzothiazole Activation: A Room-Temperature Cascade of C[BOND]H Deprotonation, C[BOND]C Coupling, Ring-Opening, and Nucleophilic Addition Reactions (pages 9857–9860)

      Dr. Victoria L. Blair, Prof. William Clegg, Dr. Alan R. Kennedy, Zoe Livingstone, Dr. Luca Russo and Dr. Eva Hevia

      Article first published online: 22 JUL 2011 | DOI: 10.1002/anie.201103275

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      Ligand domin(o)ated: In contrast to the straightforward deprotonation of benzothiazole using Grignard reagents, treatment of benzothiazole with 1 leads to a novel type of activation. The initial magnesiation initiates an unstoppable domino reaction of C[BOND]C coupling, ring opening, nucleophilic addition, and deprotonation to give 2. THF=tetrahydrofuran.

    8. Solar Cells

      High-Performance Silicon Nanowire Array Photoelectrochemical Solar Cells through Surface Passivation and Modification (pages 9861–9865)

      Xin Wang, Prof. Kui-Qing Peng, Xiao-Jun Pan, Xue Chen, Yang Yang, Li Li, Prof. Xiang-Min Meng, Prof. Wen-Jun Zhang and Prof. Shuit-Tong Lee

      Article first published online: 9 SEP 2011 | DOI: 10.1002/anie.201104102

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      Nanowire solar cells: Pt nanoparticle (PtNP) decorated C/Si core/shell nanowire photoelectrochemical solar cells (see picture) show high conversion efficiency of 10.86 % and excellent stability in aggressive electrolytes under 1-sun AM 1.5 G illumination. Superior device performance is achieved by improved surface passivation of the nanowires by carbon coating and enhanced interfacial charge transfer by PtNPs.

    9. Molecular Devices

      Foldamer-Tuned Switching Kinetics and Metastability of [2]Rotaxanes (pages 9866–9870)

      Kang-Da Zhang, Prof. Xin Zhao, Dr. Gui-Tao Wang, Prof. Yi Liu, Ying Zhang, Prof. Hao-Jie Lu, Prof. Xi-Kui Jiang and Prof. Zhan-Ting Li

      Article first published online: 2 SEP 2011 | DOI: 10.1002/anie.201104099

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      Slip sliding away: Foldamers (see picture, red) can function as modular stoppers to regulate the slippage and de-slippage of pseudorotaxanes and the switching kinetics and metastability of bistable rotaxanes. By simply changing the solvent or the length of the hydrogen-bonded foldamer, the lifetime of the metastable co-conformation state can be increased dramatically, from several minutes to as long as several days.

    10. Natural Products

      Development of Highly Cytotoxic and Actin-Depolymerizing Biotin Derivatives of Aplyronine A (pages 9871–9874)

      Dr. Masaki Kita, Yuichiro Hirayama, Miyuki Sugiyama and Prof. Dr. Hideo Kigoshi

      Article first published online: 27 SEP 2011 | DOI: 10.1002/anie.201103802

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      Tied up: A PEG-linked biotin derivative of marine macrolide aplyronine A (ApA; see scheme) is shown to exhibit potent cytotoxicity and cause actin disassembly in tumor cells. This method of introducing a PEG linker at the end of the aliphatic tail should offer perspectives for developing and using versatile actin-targeting molecular probes. PEG=poly(ethylene glycol)

    11. Purifying Heterodimers

      Purification and Magnetic Interrogation of Hybrid Au-Fe3O4 and FePt-Fe3O4 Nanoparticles (pages 9875–9879)

      Jacob S. Beveridge, Matthew R. Buck, James F. Bondi, Dr. Rajiv Misra, Prof. Peter Schiffer, Prof. Raymond E. Schaak and Prof. Mary Elizabeth Williams

      Article first published online: 6 SEP 2011 | DOI: 10.1002/anie.201104829

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      Purifying heterodimers: Differential magnetic catch and release separation is used to purify two important hybrid nanocrystal systems, Au-Fe3O4 and FePt-Fe3O4. The purified samples have substantially different magnetic properties compared to the as-synthesized materials: the magnetization values are more accurate and magnetic polydispersity is identified in morphologically similar hybrid nanoparticles.

    12. C[BOND]H Activation

      Synthesis of Phenanthridinones from N-Methoxybenzamides and Arenes by Multiple Palladium-Catalyzed C[BOND]H Activation Steps at Room Temperature (pages 9880–9883)

      Jaganathan Karthikeyan and Prof. Dr. Chien-Hong Cheng

      Article first published online: 2 SEP 2011 | DOI: 10.1002/anie.201104311

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      Many steps make light work: Substituted phenanthridinones can be obtained with high regioselectivity and in very good yields by palladium-catalyzed cyclization reactions of N-methoxybenzamides with arenes (see scheme). The reaction proceeds through multiple oxidative C[BOND]H activation and C[BOND]C/C[BOND]N formation steps in one pot at room temperature, and thus provides a simple method for generating bioactive phenanthridinones.

    13. C[BOND]H Amination

      Enantioselective Intramolecular Benzylic C[BOND]H Bond Amination: Efficient Synthesis of Optically Active Benzosultams (pages 9884–9887)

      Masami Ichinose, Dr. Hidehiro Suematsu, Yoichi Yasutomi, Yota Nishioka, Dr. Tatsuya Uchida and Prof. Tsutomu Katsuki

      Article first published online: 12 SEP 2011 | DOI: 10.1002/anie.201101801

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      'Salen' along: The iridium(III)–salen complex 1 efficiently catalyzes the title reaction of 2-ethylbenzenesulfonyl azides to give five-membered sultams with high enantioselectivity. Other 2-alkyl-substitued substrates lead to five- and six-membered sultams with high enantioselectivity; the regioselectivity depends upon the substrate and the catalyst used. EDG=electron-donating group.

    14. Posttranslational Modification

      Expanded Click Conjugation of Recombinant Proteins with Ubiquitin-Like Modifiers Reveals Altered Substrate Preference of SUMO2-Modified Ubc9 (pages 9888–9892)

      MSc. Stefanie Sommer, MSc. Nadine D. Weikart, Dipl.-Ing. Andreas Brockmeyer, Dr. Petra Janning and Prof. Dr. Henning D. Mootz

      Article first published online: 7 SEP 2011 | DOI: 10.1002/anie.201102531

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      Wrestling with SUMO: The chemical conjugation of proteins with small ubiquitin-like modifiers (SUMO) can be achieved by a copper(I)-catalyzed cycloaddition and unnatural amino acid mutagenesis (see scheme). This approach overcomes previous restrictions related to the primary sequence of proteins and coupling conditions. Moreover, biochemical data suggests that this triazole linkage presents the modifier in a proper distance and orientation relative to the target protein.

    15. Nanotubes

      Formation of Efficient Catalytic Silver Nanoparticles on Carbon Nanotubes by Adenine Functionalization (pages 9893–9897)

      Dr. Prabhpreet Singh, Dr. Giuseppe Lamanna, Dr. Cécilia Ménard-Moyon, Dr. Francesca Maria Toma, Dr. Elena Magnano, Dr. Federica Bondino, Prof. Maurizio Prato, Prof. Sandeep Verma and Dr. Alberto Bianco

      Article first published online: 14 SEP 2011 | DOI: 10.1002/anie.201102976

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      Stuck together: Adenine/carbon nanotube hybrids trigger the formation of controlled-size catalytic silver nanoparticles on the nanotube surface (see picture). The catalytic efficiency of the resulting species was assessed in the oxidation of 2-methylhydroquinone to its corresponding benzoquinone, with complete recovery and without loss of activity of the catalyst.

    16. Composite Nanocrystals

      Triple-Layer (Au@Perylene)@Polyaniline Nanocomposite: Unconventional Growth of Faceted Organic Nanocrystals on Polycrystalline Au (pages 9898–9902)

      Melinda Sindoro, Yuhua Feng, Shuangxi Xing, Dr. Hai Li, Jun Xu, Hailong Hu, Cuicui Liu, Yawen Wang, Prof. Hua Zhang, Prof. Zexiang Shen and Prof. Hongyu Chen

      Article first published online: 5 SEP 2011 | DOI: 10.1002/anie.201102994

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      Unconventional crystal growth: Core/shell nanocrystals were obtained by growth of a dominant single-crystalline phase of perylene over polycrystalline Au nanoparticle seeds and isolated by coating with polyaniline (PANI) shells. Perylene is released in the presence of sodium dodecyl sulfate (SDS) micelles (see schematic). The TEM images show (Au@perylene)@PANI nanocomposites before and after complete release of perylene leaving Au@PANI (inset).

    17. Electrocatalysis

      [Mn(bipyridyl)(CO)3Br]: An Abundant Metal Carbonyl Complex as Efficient Electrocatalyst for CO2 Reduction (pages 9903–9906)

      Marc Bourrez, Florian Molton, Dr. Sylvie Chardon-Noblat and Dr. Alain Deronzier

      Article first published online: 16 SEP 2011 | DOI: 10.1002/anie.201103616

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      Manganese at work: Carbonyl bipyridyl complexes based on manganese, a non-noble abundant and inexpensive metal, have been proved to be excellent molecular catalysts for the selective electrochemical reduction of CO2 to CO under mild conditions. Another advantage of manganese complexes over rhenium complexes is that these catalysts operate at markedly less overpotential (0.40 V gain).

    18. High-Throughput Mass Spectrometry

      Induced Nanoelectrospray Ionization for Matrix-Tolerant and High-Throughput Mass Spectrometry (pages 9907–9910)

      Guangming Huang, Guangtao Li and Prof. R. Graham Cooks

      Article first published online: 5 SEP 2011 | DOI: 10.1002/anie.201103687

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      No-contact rule: The title method is ultra-sensitive, high-throughput (4 samples per second), easily multiplexed, and is compatible with serum, urine, and concentrated salt solutions. Other features of this method, which avoids physical contact between the electrode and the solvent (see picture), include sample economy and the ability to produce both positive and negative-ion spectra in one cycle.

    19. Ionic Liquids

      Carbon Dioxide in Ionic Liquid Microemulsions (pages 9911–9915)

      Dr. Jianling Zhang, Prof. Buxing Han, Jianshen Li, Dr. Yueju Zhao and Guanying Yang

      Article first published online: 5 SEP 2011 | DOI: 10.1002/anie.201103956

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      Tailor-made emulsion: A CO2-in-ionic-liquid microemulsion was produced for the first time. The CO2-swollen micelles are “tunable” because the micellar size can be easily adjusted by changing the pressure of CO2. The microemulsion has potential applications in materials synthesis, chemical reactions, and extraction.

    20. Solid-State Chemistry

      Crystallography Aided by Atomic Core-Level Binding Energies: Proton Transfer versus Hydrogen Bonding in Organic Crystal Structures (pages 9916–9918)

      Dr. Joanna S. Stevens, Dr. Stephen J. Byard, Dr. Colin C. Seaton, Dr. Ghazala Sadiq, Prof. Roger J. Davey and Dr. Sven L. M. Schroeder

      Article first published online: 16 SEP 2011 | DOI: 10.1002/anie.201103981

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      Ionic bond or hydrogen bridge? Brønsted proton transfer to nitrogen acceptors in organic crystals causes strong N1s core-level binding energy shifts. A study of 15 organic cocrystal and salt systems shows that standard X-ray photoelectron spectroscopy (XPS) can be used as a complementary method to X-ray crystallography for distinguishing proton transfer from H-bonding in organic condensed matter (see picture).

    21. Gold Catalysis

      Regio- and Enantioselective Hydroamination of Dienes by Gold(I)/Menthol Cooperative Catalysis (pages 9919–9922)

      Dr. Osamu Kanno, Dr. Wataru Kuriyama, Z. Jane Wang and Prof. F. Dean Toste

      Article first published online: 7 SEP 2011 | DOI: 10.1002/anie.201104076

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      Alcohol is key: Regio- and enantioselective hydroamination of 1,3-dienes has been achieved with the dinuclear catalyst (R)-DTBM-SEGPHOS. The rate and selectivity of the reaction are enhanced by alcohol additives like menthol, which coordinates the cationic gold(I) to generate a Brønsted acid that can participate in catalysis. Mbs=p-methoxybenzenesulfonyl.

    22. Bond Activation

      Bond Activation with an Apparently Benign Ethynyl Dithiocarbamate Ar[BOND]C[TRIPLE BOND]C[BOND]S[BOND]C(S)NR2 (pages 9923–9925)

      Gaël Ung, Dr. Guido D. Frey, Prof. Wolfgang W. Schoeller and Prof. Guy Bertrand

      Article first published online: 16 AUG 2011 | DOI: 10.1002/anie.201104303

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      The hedgehog molecule: A simple ethynyl dithiocarbamate [Ar[BOND]C[TRIPLE BOND]C[BOND]S[BOND]C(S)NR2] is able to cleave a broad range of enthalpically strong σ bonds and to activate carbon dioxide and elemental sulfur (see picture). Depending on the substrate, the bond activation process involves either the existence of an equilibrium with the nonobservable mesoionic carbene isomer or the cooperation of the nucleophilic carbon–carbon triple bond and the electrophilic CS carbon atom.

    23. Cross-Coupling

      Construction of Substituted Benzene Rings by Palladium-Catalyzed Direct Cross-Coupling of Olefins: A Rapid Synthetic Route to 1,4-Naphthoquinone and Its Derivatives (pages 9926–9930)

      Peng Hu, Shijun Huang, Jing Xu, Prof. Zhang-Jie Shi and Prof. Weiping Su

      Article first published online: 31 AUG 2011 | DOI: 10.1002/anie.201103380

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      Ring the changes: The direct cross-coupling of electron-deficient 1,4-benzoquinone or its derivatives with electron-rich alkyl vinyl ethers proceeds in a tandem manner to produce substituted benzene rings with good selectivity and in good to excellent yields (see scheme). The reaction has the potential for the rapid synthesis of diverse substituted benzene rings as it is not limited by substituent effects.

    24. Natural Products

      Enantioselective Total Synthesis and Studies into the Configurational Stability of Bismurrayaquinone A (pages 9931–9934)

      Leah C. Konkol, Dr. Fenghai Guo, Dr. Amy A. Sarjeant and Prof. Regan J. Thomson

      Article first published online: 7 SEP 2011 | DOI: 10.1002/anie.201104726

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      Lost in rotation: The concise strategy of the first enantioselective total synthesis of bismurrayaquinone A utilized traceless stereochemical exchange to form an enantioenriched biphenyl core that was elaborated in a bidirectional manner to the natural product. Observed racemization on an unsuccessful initial route prompted studies into the configurational stability of bismurrayaquinone A and related biquinones.

    25. Enzyme Models

      Oxidation of Chloride and Subsequent Chlorination of Organic Compounds by Oxoiron(IV) Porphyrin π-Cation Radicals (pages 9935–9939)

      Dr. Zhiqi Cong, Dr. Takuya Kurahashi and Prof. Dr. Hiroshi Fujii

      Article first published online: 12 SEP 2011 | DOI: 10.1002/anie.201104461

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      Ironing it out: Oxoiron(IV) porphyrin π-cation radical complexes (see figure) serve as models for the oxidation of Cl into an active chlorinating reagent that chlorinates various organic compounds. Evidence suggests that Cl is oxidized to Cl2 via Cl.. The mechanism involving either direct electron transfer or iron(III) hypochlorite formation, and then homolysis of the Cl[BOND]O bond is discussed.

    26. Natural Products

      Synthesis of a Bicyclobutane Fatty Acid Identified from the Cyanobacterium Anabaena PCC 7120 (pages 9940–9942)

      Sean M. DeGuire, Prof. Shutao Ma and Prof. Gary A. Sulikowski

      Article first published online: 7 SEP 2011 | DOI: 10.1002/anie.201104366

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      By design: A carbanion-mediated cyclization reaction cascade serves as the key final step in the total synthesis of a novel oxylipin, which features a strained bicyclo[1.1.0]butane conjugated to a labile vinyl epoxide.

    27. Cross-Coupling

      A Single Phosphine Ligand Allows Palladium-Catalyzed Intermolecular C[BOND]O Bond Formation with Secondary and Primary Alcohols (pages 9943–9947)

      Dr. Xiaoxing Wu, Dr. Brett P. Fors and Prof. Dr. Stephen L. Buchwald

      Article first published online: 12 SEP 2011 | DOI: 10.1002/anie.201104361

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      Forging a bond: An efficient, general palladium catalyst for C[BOND]O bond-forming reactions of secondary and primary alcohols with a range of aryl halides has been developed using the ligand 1. Heteroaryl halides, and for the first time, electron-rich aryl halides can be coupled with secondary alcohols. A diverse set of substrate combinations are possible with just a single ligand, thus obviating the need to survey multiple ligands.

    28. Iron Catalysis

      Low-Pressure Hydrogenation of Carbon Dioxide Catalyzed by an Iron Pincer Complex Exhibiting Noble Metal Activity (pages 9948–9952)

      Dr. Robert Langer, Dr. Yael Diskin-Posner, Dr. Gregory Leitus, Dr. Linda J. W. Shimon, Yehoshoa Ben-David and Prof. Dr. David Milstein

      Article first published online: 9 SEP 2011 | DOI: 10.1002/anie.201104542

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      A highly active iron catalyst for the hydrogenation of carbon dioxide and bicarbonates works under remarkably low pressures and achieves activities similar to some of the best noble metal catalysts. A mechanism is proposed involving the direct attack of an iron trans-dihydride on carbon dioxide, followed by ligand exchange and dihydrogen coordination.

    29. Organocatalysis

      Generation of α,β-Unsaturated Iminium Ions by Laser Flash Photolysis (pages 9953–9956)

      Dr. Sami Lakhdar, Dipl.-Ing. Johannes Ammer and Prof. Dr. Herbert Mayr

      Article first published online: 5 SEP 2011 | DOI: 10.1002/anie.201103683

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      Two at a time: α,β-Unsaturated iminium ions can be generated by laser flash photolysis of enaminophosphonium ions (see scheme). The rate constants of their reactions with nucleophiles provide the first direct comparison of the electrophilicities of iminium ions derived from MacMillan's first- and second-generation catalysts.

    30. Nanomaterials

      Rational Design of Functional Oxide Thin Films with Embedded Magnetic or Plasmonic Metallic Nanoparticles (pages 9957–9960)

      Dr. Naoufal Bahlawane, Prof. Dr. Katharina Kohse-Höinghaus, Dr. Thomas Weimann, Dipl.-Eng. Peter Hinze, Dipl.-Chem. Sarah Röhe and Prof. Dr. Marcus Bäumer

      Article first published online: 9 SEP 2011 | DOI: 10.1002/anie.201102489

      Thumbnail image of graphical abstract

      Getting into films: Semiconductor thin films containing magnetic or plasmonic metal nanoparticles are key materials for the development of high-efficiency solar cells, bright light-emitting diodes, and new magnetoelectric devices. The catalytically driven chemical vapor deposition offers a unique way to combine deposition of the metallic nanoparticles with that of functional oxides to produce such films (see picture).

    31. Synthesis of GPI Anchors

      A General Method for Synthesis of GPI Anchors Illustrated by the Total Synthesis of the Low-Molecular-Weight Antigen from Toxoplasma gondii (pages 9961–9964)

      Yu-Hsuan Tsai, Sebastian Götze, Dr. Nahid Azzouz, Heung Sik Hahm, Prof. Dr. Peter H. Seeberger and Dr. Daniel Varon Silva

      Article first published online: 5 SEP 2011 | DOI: 10.1002/anie.201103483

      Thumbnail image of graphical abstract

      Building blocks: A new, general synthetic strategy, which allows the construction of branched glycosylphosphatidylinositols (GPIs), enables the synthesis of parasitic glycolipid 1 from Toxoplasma gondii. In addition, the structure is further confirmed by recognition of monoclonal antibodies.

    32. Cyclizations

      Domino Reactions Consisting of Heterocyclization and 1,2-Migration—Redox-Neutral and Oxidative Transition-Metal Catalysis (pages 9965–9968)

      Klaus-Daniel Umland, Adeline Palisse, Timm T. Haug and Prof. Dr. Stefan F. Kirsch

      Article first published online: 7 SEP 2011 | DOI: 10.1002/anie.201103961

      Thumbnail image of graphical abstract

      Two cats, two paths: Two novel domino reactions starting from 6-hydroxy-2-alkyl-2-alkynylcyclohexanones have been discovered. While redox-neutral platinum catalysis gives rise to furans through a sequence of cyclization, 1,2-shift, and Grob fragmentation, oxidative copper catalysis provides an entry to bicyclic 2,3-dihydrofurans. Upon cyclization and oxidation, an unusual benzilic acid rearrangement can take place in this case.

    33. Methylene Transfer

      Methyltransferase Activity of an Iridium Center with Methylpyridinium as Methylene Source (pages 9969–9972)

      Dr. Ralte Lalrempuia, Dr. Helge Müller-Bunz and Prof. Dr. Martin Albrecht

      Article first published online: 6 SEP 2011 | DOI: 10.1002/anie.201104073

      Thumbnail image of graphical abstract

      Hop on, hop off: An iridium center transfers a methyl group from pyridinium to an aryl unit, using exclusively the pyridine-bound methyl group as a mild methylene source. The reaction also involves cleavage of an unactivated C(aryl)[BOND]H bond and nitrile solvent activation. The process is reminiscent of DNA methylation and entails the formation of two new C(sp2)[BOND]C(sp3) bonds within the metal coordination sphere (see scheme).

    34. Synthetic Chiral Polymers

      Determination of the Helical Screw Sense and Side-Group Chirality of a Synthetic Chiral Polymer from Raman Optical Activity (pages 9973–9976)

      Dr. Christian Merten, Prof. Dr. Laurence D. Barron, Dr. Lutz Hecht and Dr. Christian Johannessen

      Article first published online: 8 SEP 2011 | DOI: 10.1002/anie.201104345

      Thumbnail image of graphical abstract

      Splitting it up: Excellent agreement between the experimental and the quantum-chemically simulated Raman optical activity (ROA) spectrum of (+)-poly(trityl methacrylate) shows that the polymer backbone adopts a left-handed helical conformation while the trityl side groups display a left-handed propeller conformation. Thus ROA can be used to determine the complete structure of synthetic chiral polymers in solution.

    35. Cancer Therapy

      Synthetic Antitumor Vaccines Containing MUC1 Glycopeptides with Two Immunodominant Domains—Induction of a Strong Immune Response against Breast Tumor Tissues (pages 9977–9981)

      Nikola Gaidzik, Anton Kaiser, Danuta Kowalczyk, Dr. Ulrika Westerlind, Bastian Gerlitzki, Prof. Dr. Hans Peter Sinn, Prof. Dr. Edgar Schmitt and Prof. Dr. Horst Kunz

      Article first published online: 9 SEP 2011 | DOI: 10.1002/anie.201104529

      Thumbnail image of graphical abstract

      A shot in the arm for cancer treatment: Two MUC1 tetanus toxoid vaccines were synthesized and induced a strong immune response in mice. The antibodies elicited by the vaccines show a high selectivity for the tumor cells in mammary carcinoma tissues and also distinguish between tumor tissues at different stages.

    36. 2D Spontaneous Resolution

      Self-Assembly and Two-Dimensional Spontaneous Resolution of Cyano-Functionalized [7]Helicenes on Cu(111) (pages 9982–9986)

      Prof. Meike Stöhr, Dr. Serpil Boz, Dr. Michael Schär, Manh-Thuong Nguyen, Dr. Carlo A. Pignedoli, Dr. Daniele Passerone, Dr. W. Bernd Schweizer, Prof. Carlo Thilgen, Prof. Thomas A. Jung and Prof. François Diederich

      Article first published online: 12 SEP 2011 | DOI: 10.1002/anie.201102627

      Thumbnail image of graphical abstract

      Birds of a feather flock together: STM and DFT studies provide the first example of spontaneous chiral resolution of a helicene on a surface. Racemic 6,13-dicyano[7]helicene forms fully segregated domains of pure enantiomers (2D conglomerate) on Cu(111). The propensity of the system to optimize intermolecular CN⋅⋅⋅HC(Ar) hydrogen bonding and CN⋅⋅⋅CN dipolar interactions translates into chiral recognition with preferential assembly of homochiral molecules.

    37. Tellurium Compounds

      An Iridium-Stabilized, Formally Uncharged Te10 Molecule with 3-Center–4-Electron Bonding (pages 9987–9990)

      Anja Günther, Martin Heise, Dr. Frank R. Wagner and Prof. Dr. Michael Ruck

      Article first published online: 27 SEP 2011 | DOI: 10.1002/anie.201102321

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      Te for 10: A tricyclic Te10 molecule is stabilized in an iridium complex (see structure). Bonding analysis reveals 3-center–4-electron bonds in the linear Te3 fragment. The tellurium atoms act as 2-electron donors to the transition-metal atoms.

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      Preview: Angew. Chem. Int. Ed. 43/2011 (page 9991)

      Article first published online: 6 OCT 2011 | DOI: 10.1002/anie.201190089

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