Angewandte Chemie International Edition

Cover image for Vol. 50 Issue 28

July 4, 2011

Volume 50, Issue 28

Pages 6183–6419

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    14. Preview
    1. Cover Picture: Multiple Catalysis with Two Chiral Units: An Additional Dimension for Asymmetric Synthesis (Angew. Chem. Int. Ed. 28/2011) (page 6183)

      Susy Piovesana, Daniele M. Scarpino Schietroma and Dr. Marco Bella

      Version of Record online: 3 JUN 2011 | DOI: 10.1002/anie.201103442

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      A sword of fire is generated when a bolt of lightning strikes a primordial plane covered by flowing molecules. The distortion upon impact causes the molecules to separate and leave for a new three-dimensional world. This artwork (“Flammenschwert”, Susy Piovesana, 2010) illustrates the concept behind the Minireview by M. Bella et al. on page 6216 ff. in which they describe the development of distinct chiral catalysts for asymmetric synthesis. The authors thank Corden Pharma for providing financial support for this cover picture.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    14. Preview
    1. Inside Cover: Controlled Self-Assembly of Rodlike Bacterial Pili Particles into Ordered Lattices (Angew. Chem. Int. Ed. 28/2011) (page 6184)

      Binrui Cao, Hong Xu and Prof. Dr. Chuanbin Mao

      Version of Record online: 7 JUN 2011 | DOI: 10.1002/anie.201103580

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      Pili are rodlike nanoparticles protruding from bacterial cell surfaces. Once detached, they can form ordered assemblies, including 1D bundles, 2D double-layer lattices, and 3D multilayer lattices, with the help of inducer molecules. As described by C. Mao and co-workers in their Communication on page 6264 ff., the assemblies can be used as biotemplates to induce the formation and organization of other materials.

  3. Back Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    14. Preview
    1. Back Cover: Interfacial Self-Assembly of Cell-like Filamentous Microcapsules (Angew. Chem. Int. Ed. 28/2011) (page 6184)

      Dr. Dorota I. Rożkiewicz, Benjamin D. Myers and Prof. Samuel I. Stupp

      Version of Record online: 3 JUN 2011 | DOI: 10.1002/anie.201103447

      Thumbnail image of graphical abstract

      Peptide amphiphiles and oppositely charged polymers can self-assemble into highly organized membranes at the interface of two aqueous solutions. In their Communication on page 6324 ff., S. I. Stupp and co-workers report how the biopolymer was sprayed into a peptide amphiphile solution to template the formation of cell-like microcapsules. The image shows SEM micrographs of a group of filamentous microcapsules, a single capsule (blue), the surface nanofilaments (yellow), and a membrane cross section (sepia).

  4. Graphical Abstract

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

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    14. Preview
    1. Flemming Besenbacher (page 6204)

      Version of Record online: 10 JUN 2011 | DOI: 10.1002/anie.201102768

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      “I enjoy the wee hours spent bouncing e-mails back and forth with my many good colleagues all over the world. The most important thing I learned is to hire students, postdocs, and young colleagues who are smarter than me …” This and more about Flemming Besenbacher can be found on page 6204.

  7. News

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

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

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

      Catalytic Hydrocarboxylation of Alkenes and Alkynes with CO2 (pages 6210–6212)

      Dr. Yugen Zhang and Siti Nurhanna Riduan

      Version of Record online: 9 JUN 2011 | DOI: 10.1002/anie.201101341

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      Taming the enemy: Great possibilities for the use of carbon dioxide as a renewable and environmentally friendly source of carbon in organic synthesis have been demonstrated through the hydrocarboxylation of simple alkenes and alkynes with CO2 (see scheme). Several versatile methods for carboxylic acid synthesis have been developed on this basis.

    2. Low-Coordinate Complexes

      Two-Coordinate Transition-Metal Centers With Metal–Metal Bonds (pages 6213–6214)

      Prof. Patrick L. Holland

      Version of Record online: 10 JUN 2011 | DOI: 10.1002/anie.201101209

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      M–M bonds meet two-coordination: Systems with metal–metal bonds are of great interest in inorganic chemistry. A recent report describes the first example of a metal–metal bond to a two-coordinate transition-metal center (see structure, Fe orange, O red, C gray). The metal–metal bond in this “xenophilic complex” is best described as a dative bond.

  10. Minireview

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

      Multiple Catalysis with Two Chiral Units: An Additional Dimension for Asymmetric Synthesis (pages 6216–6232)

      Susy Piovesana, Daniele M. Scarpino Schietroma and Dr. Marco Bella

      Version of Record online: 23 MAY 2011 | DOI: 10.1002/anie.201005955

      Thumbnail image of graphical abstract

      Divide et Impera: A newly emerging aspect of catalysis that involves the use of two chiral catalysts simultaneously is described (see picture). This Minireview highlights the features of the two-catalyst reactions and the synthetic applications of the methods.

  11. Review

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

      Multicomponent Reaction Design in the Quest for Molecular Complexity and Diversity (pages 6234–6246)

      Dr. Eelco Ruijter, Dr. Rachel Scheffelaar and Prof. Dr. Romano V. A. Orru

      Version of Record online: 27 JUN 2011 | DOI: 10.1002/anie.201006515

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      MCRs à la carte: Multicomponent reactions have become essential tools for the rapid generation of molecular complexity and diversity in chemical biology and drug discovery. These reactions are often discovered by serendipity, but rational design strategies are now playing an increasing role. Several such strategies are discussed in this Review.

  12. Communications

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

      Artificially Induced Protein–Membrane Anchorage with Cholesterol-Based Recognition Agents as a New Therapeutic Concept (pages 6248–6253)

      Miriam Avadisian, Dr. Steven Fletcher, Baoxu Liu, Dr. Wei Zhao, Dr. Peibin Yue, Daniel Badali, Dr. Wei Xu, Dr. Aaron D. Schimmer, Prof. Dr. James Turkson, Prof. Dr. Claudiu C. Gradinaru and Prof. Dr. Patrick T. Gunning

      Version of Record online: 30 JUN 2011 | DOI: 10.1002/anie.201102486

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      Keeping harm at bay: In an in vitro strategy to prevent the cellular motility of oncogenic STAT3 protein, protein–membrane anchorage was induced by the use of a rationally designed cholesterol-based protein–membrane anchor in breast-tumor cells. (The fluorescence image shows the localization of the protein to the liposome boundary of a multilamellar vesicle.)

    2. Smart Materials

      Polyelectrolyte Multilayer Films for Building Energetic Walking Devices (pages 6254–6257)

      Dr. Ying Ma, Yuanyuan Zhang, Prof. Baisheng Wu, Dr. Weipeng Sun, Dr. Zhengguang Li and Prof. Junqi Sun

      Version of Record online: 20 MAY 2011 | DOI: 10.1002/anie.201101054

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      Fast and powerful: A polyelectrolyte multilayer film was used to fabricate a humidity-responsive actuator that can drive a walking device carrying a load 120 times heavier than the actuator to walk steadily on a ratchet substrate under periodic alternation of the relative humidity (RH) between 11 and 40 % (see picture). NOA 63: Norland Optical Adhesive 63, PAA: poly(acrylic acid), PAH: poly(allylamine hydrochloride).

    3. Fluorescent Probes

      Synthesis and In Vivo Fate of Zwitterionic Near-Infrared Fluorophores (pages 6258–6263)

      Dr. Hak Soo Choi, Dr. Khaled Nasr, Dr. Sergey Alyabyev, Dina Feith, Jeong Heon Lee, Dr. Soon Hee Kim, Yoshitomo Ashitate, Dr. Hoon Hyun, Dr. Gabor Patonay, Dr. Lucjan Strekowski, Dr. Maged Henary and Dr. John V. Frangioni

      Version of Record online: 7 JUN 2011 | DOI: 10.1002/anie.201102459

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      To address two fundamental and unsolved problems in optical imaging (nonspecific uptake of near-infrared fluorophores by normal tissues and organs and incomplete elimination of unbound targeted fluorophores from the body), novel zwitterionic near-infrared fluorophores (e.g., ZW800-1) were synthesized and their performance compared in vivo to conventional molecules (e.g., ICG) as a function of charge, charge distribution, and hydrophobicity (see picture).

    4. Biomolecule Self-Assembly

      Controlled Self-Assembly of Rodlike Bacterial Pili Particles into Ordered Lattices (pages 6264–6268)

      Binrui Cao, Hong Xu and Prof. Dr. Chuanbin Mao

      Version of Record online: 30 MAY 2011 | DOI: 10.1002/anie.201102052

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      Pili pickup sticks: Rodlike type 1 bacterial pili particles (see picture, red) self-assemble into highly ordered nanostructures through molecular recognition in the presence of suitable inducers. 1D bundles, 2D double-layer lattices, and 3D multilayer lattices were produced by varying the nature and concentration of the inducers. The self-assembled pili serve as templates for nucleating and organizing inorganic nanomaterials such as silica.

    5. Magnetic Materials

      Ion-Induced Transformation of Magnetism in a Bimetallic CuFe Prussian Blue Analogue (pages 6269–6273)

      Dr. Masashi Okubo, Dr. Daisuke Asakura, Yoshifumi Mizuno, Prof. Tetsuichi Kudo, Dr. Haoshen Zhou, Dr. Atsushi Okazawa, Prof. Norimichi Kojima, Kazumichi Ikedo, Prof. Takashi Mizokawa and Prof. Itaru Honma

      Version of Record online: 25 MAY 2011 | DOI: 10.1002/anie.201102048

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      Li ions for degaussing: A Prussian blue analogue with FeIII and CuII ions bridged by CN ligands underwent a ferromagnetic transition induced by ferromagnetic interactions between the Fe and Cu ions (see picture). Li ions penetrating into this ferromagnetic framework eliminated the ferromagnetic interaction and effected the formation of a paramagnetic framework. The ferromagnetism was recovered by extracting the Li ions.

    6. Organic Electronics

      Soluble Self-Doped Conducting Polymer Compositions with Tunable Work Function as Hole Injection/Extraction Layers in Organic Optoelectronics (pages 6274–6277)

      Mi-Ri Choi, Tae-Hee Han, Kyung-Geun Lim, Seong-Hoon Woo, Dal Ho Huh and Prof. Tae-Woo Lee

      Version of Record online: 24 MAY 2011 | DOI: 10.1002/anie.201005031

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      Making light work: Polymer-based compositions with a perfluorinated ionomer (PFI) as hole injection/extraction layers are introduced for organic LEDs and organic photovoltaic cells. The work functions of the layers formed by single spin-coating could be tuned to improve device efficiency and device lifetime. The effects of the PFI surface layers on charge injection/extraction and device lifetime were investigated.

    7. Cathode Materials

      Electrospinning of Highly Electroactive Carbon-Coated Single-Crystalline LiFePO4 Nanowires (pages 6278–6282)

      Changbao Zhu, Prof. Yan Yu, Prof. Lin Gu, Katja Weichert and Prof. Dr. Joachim Maier

      Version of Record online: 30 MAY 2011 | DOI: 10.1002/anie.201005428

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      From the spinning room: LiFePO4 is a promising cathode material for lithium batteries, but it suffers from slow mass and charge transport. Electrospinning is able to produce single-crystalline LiFePO4 nanowires coated with amorphous carbon (see TEM images and small-angle electron diffraction pattern). Networks of these wires show very short diffusion lengths, thus leading to high rate performance and cycling capability.

    8. Contrast Agents

      Controlled Self-Assembling of Gadolinium Nanoparticles as Smart Molecular Magnetic Resonance Imaging Contrast Agents (pages 6283–6286)

      Dr. Gaolin Liang, Dr. John Ronald, Dr. Yuanxin Chen, Dr. Deju Ye, Dr. Prachi Pandit, Man Lung Ma, Prof. Brian Rutt and Prof. Jianghong Rao

      Version of Record online: 25 MAY 2011 | DOI: 10.1002/anie.201007018

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      Gd smart: MRI contrast agents are presented that are based on a biocompatible condensation reaction. Upon reduction, a gadolinium-containing cell-permeable small-molecule probe condenses into cyclic oligomers that subsequently self-assemble into nanoparticles (NPs) with enhanced relaxivity (by 110 % at 1.5 T and 35 °C, and 104 % in live cells at 0.5 T).

    9. Molecular Devices

      Memory Effects in Molecular Films of Free-Standing Rod-Shaped Ruthenium Complexes on an Electrode (pages 6287–6291)

      Dr. Keiichi Terada, Dr. Katsuhiko Kanaizuka, Vijay Mahadevan Iyer, Miyabi Sannodo, Sohei Saito, Dr. Katsuaki Kobayashi and Prof. Masa-aki Haga

      Version of Record online: 30 MAY 2011 | DOI: 10.1002/anie.201100142

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      Forget me not: When an oxidizing voltage pulse was applied, ruthenium complexes immobilized on an ITO electrode showed a memory effect, and the original anodic photoresponse (see picture, above) changed to a cathodic one (below).

    10. Supramolecular Biomaterials

      Electrostatic Control of Bioactivity (pages 6292–6295)

      Dr. Joshua E. Goldberger, Eric J. Berns, Dr. Ronit Bitton, Christina J. Newcomb and Prof. Samuel I. Stupp

      Version of Record online: 30 MAY 2011 | DOI: 10.1002/anie.201100202

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      The power of independence: When exhibited on the surface of self-assembling peptide-amphiphile nanofibers, the hydrophobic laminin-derived IKVAV epitope induced nanofiber bundling through interdigitation with neighboring fibers and thus decreased the bioactivity of the resulting materials. The inclusion of charged amino acids in the peptide amphiphiles disrupted the tendency to bundle and led to significantly enhanced neurite outgrowth (see picture).

    11. Asymmetric Catalysis

      C1-Symmetric Rh/Phebox-Catalyzed Asymmetric Alkynylation of α-Ketoesters (pages 6296–6300)

      Prof. Dr. Takashi Ohshima, Takahito Kawabata, Yosuke Takeuchi, Takahiro Kakinuma, Dr. Takanori Iwasaki, Takayuki Yonezawa, Hajime Murakami, Prof. Dr. Hisao Nishiyama and Prof. Dr. Kazushi Mashima

      Version of Record online: 30 MAY 2011 | DOI: 10.1002/anie.201100252

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      Thinking outside the box: A newly developed C1-symmetric Rh/Phebox complex efficiently catalyzed the asymmetric alkynylation of α-ketoester 1 with various aryl and alkyl substituted terminal alkynes to provide the corresponding chiral tertiary propargylic alcohols with up to 99 % ee (see scheme; TMS=trimethylsilyl).

    12. Distillable Salts

      Distillable Acid–Base Conjugate Ionic Liquids for Cellulose Dissolution and Processing (pages 6301–6305)

      Dr. Alistair W. T. King, Janne Asikkala, Ilpo Mutikainen, Paula Järvi and Prof. Dr. Ilkka Kilpeläinen

      Version of Record online: 23 MAY 2011 | DOI: 10.1002/anie.201100274

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      Heating up: Improved recyclability is necessary for ionic liquids destined for wood-based bioprocessing platforms. New “distillable” molten acid–base conjugates efficiently dissolve cellulose at temperatures of 100 °C. Increased temperature induces a shift of the acid–base equilibrium toward the neutral species (see picture, TMG=1,1,3,3-tetramethylguanidine), thus affording a vapor pressure and allowing for distillation of the mixture.

    13. Biosensors

      Time-Resolved FRET Biosensor Based on Amine-Functionalized Lanthanide-Doped NaYF4 Nanocrystals (pages 6306–6310)

      Datao Tu, Dr. Liqin Liu, Dr. Qiang Ju, Dr. Yongsheng Liu, Dr. Haomiao Zhu, Renfu Li and Prof. Xueyuan Chen

      Version of Record online: 24 MAY 2011 | DOI: 10.1002/anie.201100303

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      Background elimination and improved sensitivity were achieved by time-resolved (TR) detection with a FRET biosensor for traces of biomolecules such as avidin at concentrations down to 4.8 nM. As shown in the picture, UV excitation of biotinylated NaYF4:Ce/Tb nanocrystals triggers energy transfer to fluorescein isothiocyanate (FITC), whose long-lived emission due to FRET can be distinguished from the short-lived background from direct excitation.

    14. Optoelectronics

      Electrically Tunable Hysteretic Photonic Gels for Nonvolatile Display Pixels (pages 6311–6314)

      Kyosung Hwang, Dongwoo Kwak, Changjoon Kang, Daihyun Kim, Youshin Ahn and Prof. Youngjong Kang

      Version of Record online: 23 MAY 2011 | DOI: 10.1002/anie.201100398

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      Plastic pixels: Electrically tunable photonic pixels exhibiting nonvolatile photonic colors are demonstrated by coupling the hysteretic optical properties of PS-b-P2VP block copolymer photonic gels with an electrochemically induced pH gradient. The optical volatility of photonic pixels was tuned by controlling the hysteresis strength and the conversion pH value, which were both highly dependent on the species of anions pairing with pyridinium groups.

    15. Metal Nanocrystals

      Oleylamine-Mediated Shape Evolution of Palladium Nanocrystals (pages 6315–6319)

      Zhiqiang Niu, Dr. Qing Peng, Ming Gong, Hongpan Rong and Prof. Yadong Li

      Version of Record online: 23 MAY 2011 | DOI: 10.1002/anie.201100512

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      Shape control: Uniform Pd nanocrystals in the shape of icosa-, deca-, octa-, tetrahedron, and triangular plate were prepared in a hydrophobic system in which oleylamine (OAm) plays a crucial role in shape evolution by mediating the counterbalance between crystal strain and surface energy (see picture). The as-obtained Pd nanocrystals are catalytically active in the oxidation of formic acid.

    16. Molecular Electronics

      A Butterfly-Shaped Amphiphilic Molecule: Solution-Transferable and Free-Standing Bilayer Films for Organic Transistors (pages 6320–6323)

      Jie Yin, Yan Zhou, Ting Lei and Prof. Jian Pei

      Version of Record online: 27 MAY 2011 | DOI: 10.1002/anie.201100712

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      Butterflies in the stomach: Organic field-effect transistors containing a free-standing film self-assembled from an amphiphilic butterfly-shaped benzodithiophene derivative as the active layer (see picture) were fabricated by a solution transfer process. The direct self-assembly of the film from solution means that a substrate is not required for the film formation.

    17. Amphiphiles

      Interfacial Self-Assembly of Cell-like Filamentous Microcapsules (pages 6324–6327)

      Dr. Dorota I. Rożkiewicz, Benjamin D. Myers and Prof. Samuel I. Stupp

      Version of Record online: 23 MAY 2011 | DOI: 10.1002/anie.201100821

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      Spray-on: Peptide amphiphiles (PAs) and oppositely charged polymers can self-assemble into highly organized membranes (see picture) at the interface between two aqueous solutions. Nebulization was employed to spray the biopolymer into a solution of the peptide amphiphile and to template the formation of microcapsules that are loaded with a biopolymer solution and have surfaces that are decorated with nanoscale filaments.

    18. Nanocrystals

      Synthesis of Gold Nano-hexapods with Controllable Arm Lengths and Their Tunable Optical Properties (pages 6328–6331)

      Do Youb Kim, Dr. Taekyung Yu, Dr. Eun Chul Cho, Yanyun Ma, Prof. O Ok Park and Prof. Younan Xia

      Version of Record online: 6 JUN 2011 | DOI: 10.1002/anie.201100983

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      A star in the making: Gold nano-hexapods with controlled arm lengths were synthesized by selective growth on the vertices of octahedral Au seeds. Depending on the arm length, their surface plasmon resonance peaks shifted from the visible to the near-infrared region (see picture), which could be readily controlled by varying the amount of HAuCl4, the reaction temperature, or both.

      Corrected by:

      Corrigendum: Corrigendum: Synthesis of Gold Nano-hexapods with Controllable Arm Lengths and Their Tunable Optical Properties

      Vol. 50, Issue 35, 7972, Version of Record online: 17 AUG 2011

    19. Dendrimer-Based Vesicles

      Thermosensitive Molecular Assemblies from Poly(amidoamine) Dendron-Based Lipids (pages 6332–6336)

      Prof. Dr. Kenji Kono, Etsuo Murakami, Yuki Hiranaka, Dr. Eiji Yuba, Dr. Chie Kojima, Dr. Atsushi Harada and Prof. Dr. Kazuo Sakurai

      Version of Record online: 20 MAY 2011 | DOI: 10.1002/anie.201101007

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      The heat is on: Vesicles formed from poly(amidoamine) dendron-based lipids with terminal isobutyramide (IBAM) groups undergo a temperature-dependent structural transition through a change in hydration of the vesicle surface. The vesicles are stable at low temperature, but form aggregates above a specific temperature and transform to inverted rodlike micelles or fused vesicles (see picture; G2/G3=second/third generation).

    20. Tandem Oxidations

      Synthesis of 2-Keto-anti-1,3-diols by Chemoselective Tandem Oxidation of 2-B(pin)-Substituted Allylic Alcohols (pages 6337–6340)

      Dr. Mahmud M. Hussain, Dr. Jorge Hernández Toribio, Dr. Patrick J. Carroll and Prof. Patrick J. Walsh

      Version of Record online: 26 MAY 2011 | DOI: 10.1002/anie.201005742

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      A new role for vinyl boronates: Vinyl boronate esters are well known as synthons for ketones and for their ability to participate in cross-coupling reactions. A tandem oxidation is introduced to convert 2-B(pin)-substituted allylic alcohols into 2-keto-anti-1,3-diols with high diastereoselectivity. Under these reaction conditions, the vinyl boronate ester is now a synthon for α-hydroxy ketones.

    21. Synthetic Methods

      Palladium-Catalyzed Bromoalkynylation of C[BOND]C Double Bonds: Ring-Structure-Dependent Synthesis of 7-Alkynyl Norbornanes and Cyclobutenyl Halides (pages 6341–6345)

      Yibiao Li, Xiaohang Liu, Prof. Huanfeng Jiang, Bifu Liu, Zhengwang Chen and Peng Zhou

      Version of Record online: 31 MAY 2011 | DOI: 10.1002/anie.201100002

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      Strain versus flexibility: The palladium-catalyzed reaction of haloalkynes with norbornene derivatives leads to 7-alkynyl norbornane products (see scheme). Key to the success of this reaction is the formation of a “bridging” palladium species, which can rearrange to result in a C-7 functionalization. The ring-structure-dependent [2+2] cycloaddition of haloalkynes with cyclooctene has been achieved in moderate to good yields under similar conditions.

    22. Nanoparticle Synthesis

      You have full text access to this OnlineOpen article
      Cathodic Corrosion: A Quick, Clean, and Versatile Method for the Synthesis of Metallic Nanoparticles (pages 6346–6350)

      Dr. Alexei I. Yanson, Dr. Paramaconi Rodriguez, Dr. Nuria Garcia-Araez, Rik V. Mom, Dr. Frans D. Tichelaar and Prof. Marc T. M. Koper

      Version of Record online: 27 MAY 2011 | DOI: 10.1002/anie.201100471

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      A simple and effective method for the synthesis of nanoparticles is reported based on extreme cathodic polarization of a metal, formation of cation-stabilized metal anions, and their agglomeration (see picture). The improved catalytic activity of these nanoparticles in the oxidation of carbon monoxide as well as methanol is shown using platinum.

    23. Lithium–Oxygen Batteries

      Oxygen Reactions in a Non-Aqueous Li+ Electrolyte (pages 6351–6355)

      Dr. Zhangquan Peng, Dr. Stefan A. Freunberger, Dr. Laurence J. Hardwick, Yuhui Chen, Dr. Vincent Giordani, Dr. Fanny Bardé, Prof. Dr. Petr Novák, Prof. Duncan Graham, Prof. Jean-Marie Tarascon and Prof. Peter G. Bruce

      Version of Record online: 23 MAY 2011 | DOI: 10.1002/anie.201100879

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      Taking the shortcut: Spectroscopic data (see picture) provide direct evidence that in non-aqueous Li+ electrolyte, O2 is reduced to O2, which then forms LiO2 on the electrode surface which disproportionates to Li2O2. On charging, Li2O2 decomposes directly, in a one-step reaction to evolve O2 and does not pass through LiO2 as an intermediate.

    24. Endofullerenes

      Radical Derivatives of Insoluble La@C74: X-ray Structures, Metal Positions, and Isomerization (pages 6356–6359)

      Dr. Xing Lu, Dr. Hidefumi Nikawa, Takashi Kikuchi, Dr. Naomi Mizorogi, Dr. Zdenek Slanina, Dr. Takahiro Tsuchiya, Prof. Dr. Shigeru Nagase and Prof. Dr. Takeshi Akasaka

      Version of Record online: 27 MAY 2011 | DOI: 10.1002/anie.201100961

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      Insoluble fullerenes solubilized: Addition of dichlorophenyl radicals to insoluble La@C74 affords two series of regioisomers in which dichlorophenyl groups with different substitution patterns are singly bonded to one of two adjacent cage carbon atoms. X-ray diffraction studies reveal that the internal metal atom is responsible for such addition patterns, while addition to different sites modifies the motion of the metal atom (see picture).

    25. Boryl Complexes

      Rare Earth Metal Boryl Complexes: Synthesis, Structure, and Insertion of a Carbodiimide and Carbon Monoxide (pages 6360–6363)

      Dr. Shihui Li, Dr. Jianhua Cheng, Dr. Yanhui Chen, Dr. Masayoshi Nishiura and Prof. Dr. Zhaomin Hou

      Version of Record online: 13 MAY 2011 | DOI: 10.1002/anie.201101107

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      Among the first of their kind: Scandium boryl complex 1 and its Gd analogue were prepared by reaction of a boryl lithium compound with [Ln(CH2SiMe3)2(THF)x][BPh4] (Ln=Sc, Gd). Reaction of 1 with N,N′-diisopropylcarbodiimide gave bis(amidinate) complex 2, which affords 3 by double CO insertion into the Sc[BOND]B bond, nucleophilic addition of an amidinate, and migration of the SiMe3 to the resulting ketene moiety (see scheme).

    26. Organocatalysis

      Brønsted Acid Catalysis: Hydrogen Bonding versus Ion Pairing in Imine Activation (pages 6364–6369)

      Matthias Fleischmann, Diana Drettwan, Dr. Erli Sugiono, Prof. Dr. Magnus Rueping and Prof. Dr. Ruth M. Gschwind

      Version of Record online: 3 JUN 2011 | DOI: 10.1002/anie.201101385

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      Behind the scenes: NMR spectroscopy was used to distinguish hydrogen bonding and ion pairing in the activation of imines by a phosphate catalyst (see structures). Hydrogen-bond strength and the amount of the hydrogen-bonded species present are decisive for the catalytic reaction and can be manipulated by introducing substituents with different electronic properties. This insight should guide the development of more efficient catalytic systems.

    27. Annulation Reactions

      Palladium-Mediated Annulation of Vinyl Aziridines with Michael Acceptors: Stereocontrolled Synthesis of Substituted Pyrrolidines and Its Application in a Formal Synthesis of (−)-α-Kainic Acid (pages 6370–6374)

      Dr. Martin A. Lowe, Dr. Mehrnoosh Ostovar, Dr. Serena Ferrini, C. Chun Chen, Paul G. Lawrence, Dr. Francesco Fontana, Dr. Andrew A. Calabrese and Prof. Varinder K. Aggarwal

      Version of Record online: 27 MAY 2011 | DOI: 10.1002/anie.201101389

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      Just add salt: Vinyl aziridines have been treated with methyl vinyl ketone or ethyl thioacrylate in the presence of Pd0 to give pyrrolidines with moderate to good diastereoselectivity. The presence of nBu4NCl was critical to successful annulation. The synthetic utility of the methodology has been demonstrated in a short (formal) synthesis of (−)-α-kainic acid.

    28. Siloxyallenes

      Enantioselective Synthesis of Siloxyallenes from Alkynoylsilanes by Reduction and a Brook Rearrangement and Their Subsequent Trapping in a [4+2] Cycloaddition (pages 6375–6378)

      Dr. Michiko Sasaki, Yasuhiro Kondo, Dr. Masatoshi Kawahata, Prof. Dr. Kentaro Yamaguchi and Prof. Dr. Kei Takeda

      Version of Record online: 31 MAY 2011 | DOI: 10.1002/anie.201102430

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      Two flavors of selectivity: An enantioselective Meerwein–Ponndorf–Verley-type reduction of alkynoylsilanes by a chiral lithium amide followed by a Brook rearrangement and SE2′ electrophilic substitution provides the title compounds in a one-pot process. In the case of enynoylsilanes, the generated vinylallenes undergo in situ [4+2] cycloaddition to afford highly functionalized polycyclic compounds with unusual facial selectivity.

    29. C[BOND]H Bond Activation

      Ruthenium-Catalyzed Oxidative Annulation by Cleavage of C[BOND]H/N[BOND]H Bonds (pages 6379–6382)

      Prof. Dr. Lutz Ackermann, Dr. Alexander V. Lygin and Dipl.-Chem. Nora Hofmann

      Version of Record online: 24 MAY 2011 | DOI: 10.1002/anie.201101943

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      Bond activation in action: Unprecedented ruthenium-catalyzed oxidative annulations of alkynes through cleavage of C[BOND]H bonds set the stage for an efficient 1(2H)-isoquinolone synthesis with ample scope (see scheme; tAm=tert-amyl). Mechanistic studies provided strong evidence for a rate-limiting C[BOND]H bond metalation through carboxylate assistance.

    30. Phosphinidenes

      Enhanced Nucleophilic Behavior of a Dimolybdenum Phosphinidene Complex: Multicomponent Reactions with Activated Alkenes and Alkynes in the Presence of CO or CNXyl (pages 6383–6387)

      Dr. M. Angeles Alvarez, Prof. Dr. M. Esther García, Prof. Dr. Miguel A. Ruiz and Dipl.-Chem. Jaime Suárez

      Version of Record online: 23 MAY 2011 | DOI: 10.1002/anie.201101940

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      A ligand makes a difference: The reactivity of a dimolybdenum phosphinidene complex with alkenes and alkynes is substantially modified by the presence of two-electron donors such as CO or CNXyl (Xyl=xylyl). Under these multicomponent reaction conditions, rapid formation of phosphametallacyclopentene rings takes place at room temperature. These reactions proceed in all cases with very high chemo- and regioselectivity.

    31. Gradient Polymers

      Zwitterionic Copolymerization: Synthesis of Cyclic Gradient Copolymers (pages 6388–6391)

      Eun Ji Shin, Hayley A. Brown, Silvia Gonzalez, Dr. Wonhee Jeong, Dr. James L. Hedrick and Prof. Dr. Robert M. Waymouth

      Version of Record online: 25 MAY 2011 | DOI: 10.1002/anie.201101853

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      How to get rich fast: The zwitterionic copolymerization of δ-valerolactone (VL) and ε-caprolactone (CL) provides an expedient route to cyclic gradient copolymers. The faster ring-opening of VL relative to CL with N-heterocyclic carbenes, coupled with sufficiently long lifetimes of the growing zwitterions leads to a polymer structure comprised of VL-rich sequences that transition to CL-rich sequences in a cyclic macromolecule (see scheme).

    32. Asymmetric Catalysis

      Highly Enantioselective Catalytic Synthesis of Functionalized Chiral Diazoacetoacetates (pages 6392–6395)

      Dr. Xinfang Xu, Prof. Wen-Hao Hu and Prof. Michael P. Doyle

      Version of Record online: 31 MAY 2011 | DOI: 10.1002/anie.201102405

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      In addition: The Mukaiyama–Michael addition in the presence of a chiral copper(II) Lewis acid is a highly enantioselective and efficient method for the construction of a broad range of chiral γ-functionalized diazoacetoacetates. These products can be conveniently transformed into useful enantiomer-enriched 1,5-diesters (see scheme, Np=1-naphthyl, TBS=tert-butyldimethylsilyl).

    33. Continuous Synthesis

      Continuous-Flow Synthesis of 3,3-Disubstituted Oxindoles by a Palladium-Catalyzed α-Arylation/Alkylation Sequence (pages 6396–6400)

      Dr. Pengfei Li and Prof. Stephen L. Buchwald

      Version of Record online: 7 JUN 2011 | DOI: 10.1002/anie.201102401

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      Facilitating chemistry: Key to the success of Pd-catalyzed α-arylation of oxindoles in continuous flow involved a biphasic system, a precatalyst, and a packed-bed microreactor. Furthermore, this reaction was integrated into a two-step continuous-flow sequence for rapid, modular, and efficient syntheses of 3,3-disubstituted oxindoles.

    34. C[BOND]H Activation

      The Mechanism of the Titanium-Catalyzed Hydroaminoalkylation of Alkenes (pages 6401–6405)

      Insa Prochnow, Patrick Zark, Prof. Dr. Thomas Müller and Prof. Dr. Sven Doye

      Version of Record online: 31 MAY 2011 | DOI: 10.1002/anie.201101239

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      Kinetic studies on the intramolecular titanium-catalyzed hydroaminoalkylation of alkenes (see scheme) are consistent with theoretical results and lead to the conclusion that the rate-determining step of the catalytic cycle is the C[BOND]H activation at the α position to the nitrogen atom. The reaction has a high activation energy and involves a moderately ordered transition state.

    35. Peptide Synthesis

      Fragment Condensation of C-Terminal Pseudoproline Peptides without Racemization on the Solid Phase (pages 6406–6410)

      Dr. Christian Heinlein, Dr. Daniel Varón Silva, Andrea Tröster, Jasmin Schmidt, Angelina Gross and Prof. Carlo Unverzagt

      Version of Record online: 31 MAY 2011 | DOI: 10.1002/anie.201101270

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      Hot couplings without racemization: Protected peptides featuring C-terminal pseudoprolines were synthesized on a solid support, and these versatile building blocks were used in convergent peptide-segment couplings, which proceeded without racemization even under microwave conditions. The solubility-enhancing effect of pseudoproline residues facilitated the synthesis of complex RNase 39-mer glycopeptide thioesters.

    36. Hydrogen Storage

      CO2-“Neutral” Hydrogen Storage Based on Bicarbonates and Formates (pages 6411–6414)

      Albert Boddien, Felix Gärtner, Christopher Federsel, Peter Sponholz, Dörthe Mellmann, Dr. Ralf Jackstell, Dr. Henrik Junge and Prof. Matthias Beller

      Version of Record online: 23 MAY 2011 | DOI: 10.1002/anie.201101995

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      Let the circle be unbroken! One ruthenium catalyst generated in situ facilitates the selective hydrogenation of bicarbonates and carbonates, as well as CO2 and base, to give formates and also the selective dehydrogenation of formates back to bicarbonates. The two reactions can be coupled, leading to a reversible hydrogen-storage system. dppm=1,2-bis(diphenylphosphino)methane.

    37. Molecular Motor

      A Molecular Four-Stroke Motor (pages 6415–6418)

      Prof. Dr. Gebhard Haberhauer

      Version of Record online: 31 MAY 2011 | DOI: 10.1002/anie.201101501

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      Round and round it goes: In the molecular four-stroke motor the forward and backward moving of the pushing blade of the motor is combined with the closing and opening of the blade in such a way that there is a net rotation about a virtual axis (see scheme). Thus, during one cycle, surrounding molecules should automatically be transported in a definite direction.

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