Angewandte Chemie International Edition

Cover image for Vol. 49 Issue 46

November 8, 2010

Volume 49, Issue 46

Pages 8535–8763

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Review
    10. Communications
    11. Preview
    1. Cover Picture: Metal–Organic Frameworks from Edible Natural Products (Angew. Chem. Int. Ed. 46/2010) (page 8535)

      Dr. Ronald A. Smaldone, Dr. Ross S. Forgan, Dr. Hiroyasu Furukawa, Dr. Jeremiah J. Gassensmith, Prof. Alexandra M. Z. Slawin, Prof. Omar M. Yaghi and Prof. J. Fraser Stoddart

      Article first published online: 16 AUG 2010 | DOI: 10.1002/anie.201004618

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      Edible MOFs are on the menu as the chef presents his culinary creation. In their Communication on page 8630 ff., J. F. Stoddart, O. M. Yaghi, and co-workers describe the synthesis of metal–organic frameworks (MOFs) solely from food-grade ingredients, namely γ-cyclodextrin, alkali-metal salts, water, and alcohol. These renewable, biocompatible CD-MOFs are robust, permanently porous, and are capable of storing organic molecules. Picture design: Aleksander Bosoy.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Review
    10. Communications
    11. Preview
    1. Inside Cover: Synchronized Synthesis of Peptide-Based Macrocycles by Digital Microfluidics (Angew. Chem. Int. Ed. 46/2010) (page 8536)

      Mais J. Jebrail, Alphonsus H. C. Ng, Dr. Vishal Rai, Dr. Ryan Hili, Prof. Andrei K. Yudin and Prof. Aaron R. Wheeler

      Article first published online: 16 AUG 2010 | DOI: 10.1002/anie.201004588

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      A microfluidic technique for synchronized chemical synthesis has been developed and applied to the formation of peptide-based macrocycles and analogues with side chains appended during ring-opening. A. R. Wheeler and co-workers describe this digital microfluidic technique, in which discrete droplets of samples and reagents are controlled by electric potentials applied to an array of electrodes coated with a hydrophobic insulator, in their Communication on page 8625 ff. Artwork: M. Jebrail/S. Youhanna.

  3. Graphical Abstract

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

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Review
    10. Communications
    11. Preview
    1. Thomas M. Klapötke (page 8561)

      Article first published online: 12 OCT 2010 | DOI: 10.1002/anie.201005058

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      “My favorite subject at school was chemistry. The most significant advance of the last 100 years has been rocket propulsion …” This and more about Thomas M. Klapötke can be found on page 8561.

  6. Book Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Review
    10. Communications
    11. Preview
    1. Profile der Zellbiologie. 36 Profile der deutschen Geschichte. By Lothar Jaenicke. (pages 8562–8563)

      Ute Deichmann

      Article first published online: 22 OCT 2010 | DOI: 10.1002/anie.201005790

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      S. Hirzel, Stuttgart 2010. 329 pp., hardcover € 34.00.—ISBN 978-3777616933

  7. Highlights

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Review
    10. Communications
    11. Preview
    1. Plant-Based Plastics

      Nature’s Polyethylene (pages 8564–8566)

      David J. Cole-Hamilton

      Article first published online: 13 SEP 2010 | DOI: 10.1002/anie.201002593

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      A new substitute for polyethylene is derived entirely from plant-based sources through methyl oleate or methyl erucate. Methoxycarbonylation with a palladium catalyst gives C19 or C24 α,ω-diesters, which are polymerized with their reduced alcohol forms to give polyesters with properties very like those of polyethylene (see scheme).

    2. Hydrogenases

      The Modular Assembly of Clusters Is the Natural Synthetic Strategy for the Active Site of [FeFe] Hydrogenase (pages 8567–8569)

      Ryan D. Bethel, Michael L. Singleton and Prof. Marcetta Y. Darensbourg

      Article first published online: 15 SEP 2010 | DOI: 10.1002/anie.201003747

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      The 6Fe supercluster that comprises the [FeFe] hydrogenase active site has been shown to involve a modular buildup of iron–sulfur clusters. Only three accessory proteins are needed to produce the CN, CO, and μ-SCH2NHCH2S- units that bind to the 2Fe2S subcluster precursor. The scaffold/carrier protein inserts the preformed 2Fe subcluster into the apoprotein through a channel, which then closes to encapsulate the completed active site.

    3. Molecular Recognition

      Introducing Quadrupole Interactions into the Peptide Design Toolkit (pages 8570–8572)

      Dr. Hana Robson Marsden, Prof. Dr. Johannes G. E. M. Fraaije and Dr. Alexander Kros

      Article first published online: 4 OCT 2010 | DOI: 10.1002/anie.201003828

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      A star attraction: The electrostatic interactions between aromatic amino acid side chains having opposite quadrupole moments are sufficient to introduce specificity into peptide binding interactions. The demonstration of this principle expands the repertoire of chemical tools that can be used to engineer specific peptide–peptide interactions, thus paving the way to new functional assemblies.

  8. Review

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

      Nucleic Acid/Organic Polymer Hybrid Materials: Synthesis, Superstructures, and Applications (pages 8574–8587)

      Minseok Kwak and Prof. Dr. Andreas Herrmann

      Article first published online: 15 SEP 2010 | DOI: 10.1002/anie.200906820

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      Skillful biohybrid: Combined biological and synthetic macromolecules make up an emerging structural class in material science. This Review describes the synthesis and potential applications of these compounds and DNA block copolymers in particular.

  9. Communications

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

      Chiral Brønsted Acid Catalyzed Enantioselective α-Aminoxylation of Enecarbamates (pages 8588–8592)

      Min Lu, Dr. Yunpeng Lu, Di Zhu, Xiaofei Zeng, Dr. Xinsheng Li and Prof. Dr. Guofu Zhong

      Article first published online: 26 JUL 2010 | DOI: 10.1002/anie.201002640

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      A practically simple, highly enantioselective Brønsted acid catalyzed α-aminoxylation of enecarbamates extends the substrate scope for the α-aminoxylation to linear and aromatic ketones, allowing convergent and stereoselective access to valuable α-hydroxy ketones, β-amino alcohols, and cis-oxazolidinones.

    2. Fluorescent Probes

      Design of a Highly Sensitive Fluorescent Probe for Interfacial Electron Transfer on a TiO2 Surface (pages 8593–8597)

      Dr. Takashi Tachikawa, Nan Wang , Soichiro Yamashita, Shi-Cong Cui and Prof. Dr. Tetsuro Majima

      Article first published online: 4 OCT 2010 | DOI: 10.1002/anie.201004976

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      Single-molecule fluorescent probe: The formation of the highly fluorescent 4-NHOH form of a 3,4-dinitrophenyl-substituted boron dipyrromethane dye can be used to study interfacial electron transfer on individual TiO2 particles (see picture; B yellow, C gray, F green, H white, O red). Kinetic and image analyses of the resulting fluorescence bursts reveal temporal dynamics of molecular interactions and reactive-site distributions.

    3. Photocatalysis

      Enhancement of the Photoinduced Oxidation Activity of a Ruthenium(II) Complex Anchored on Silica-Coated Silver Nanoparticles by Localized Surface Plasmon Resonance (pages 8598–8601)

      Dr. Kohsuke Mori, Masayoshi Kawashima, Prof. Dr. Michel Che and Prof. Dr. Hiromi Yamashita

      Article first published online: 30 SEP 2010 | DOI: 10.1002/anie.201004942

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      Plasmonic photocatalyst: Anchoring the dye [Ru(bpy)3]2+ (bpy=2,2′-bipyridine) on the surface of Ag nanoparticles coated with a thin SiO2 layer (see picture) afforded a photocatalyst whose phosphorescence emission and photoinduced oxidation activity in the selective liquid-phase oxidation of styrene are efficiently enhanced through interaction with the localized surface plasmon resonance of the core Ag nanoparticles.

    4. Core/Shell Nanoparticles

      Core-Protected Platinum Monolayer Shell High-Stability Electrocatalysts for Fuel-Cell Cathodes (pages 8602–8607)

      Dr. Kotaro Sasaki, Dr. Hideo Naohara, Dr. Yun Cai, Dr. Yong Man Choi, Dr. Ping Liu, Dr. Miomir B. Vukmirovic, Dr. Jia X. Wang and Dr. Radoslav R. Adzic

      Article first published online: 7 OCT 2010 | DOI: 10.1002/anie.201004287

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      More than skin deep: Platinum monolayers can act as shells for palladium nanoparticles to lead to electrocatalysts with high activities and an ultralow platinum content, but high platinum utilization. The stability derives from the core protecting the shell from dissolution. In fuel-cell tests, no loss of platinum was observed in 200 000 potential cycles, whereas loss of palladium was significant.

    5. Liquid-Crystal Biosensors

      Signal-Enhanced Liquid-Crystal DNA Biosensors Based on Enzymatic Metal Deposition (pages 8608–8611)

      Hui Tan, Shengyuan Yang, Prof. Guoli Shen, Prof. Ruqin Yu and Prof. Dr. Zhaoyang Wu

      Article first published online: 30 SEP 2010 | DOI: 10.1002/anie.201004272

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      No cloudiness with a silver lining: Deposition of metallic silver on a liquid-crystal substrate with attached DNA strands greatly alters the surface topology and induces a homeotropic-to-tiled transition of the LC molecules surrounding them, resulting in an obvious change in appearance from dark to birefringent (see picture; Ag: spheres). This enzymatic silver deposition is an excellent signal-enhancement strategy for LC optical amplification.

    6. Superamphiphiles

      An Enzyme-Responsive Polymeric Superamphiphile (pages 8612–8615)

      Chao Wang, Qishui Chen, Prof. Zhiqiang Wang and Prof. Xi Zhang

      Article first published online: 30 SEP 2010 | DOI: 10.1002/anie.201004253

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      Responding to treatment: A superamphiphile is formed between a double-hydrophilic polymer (methoxy-poly(ethylene glycol)-block-poly(L-lysine hydrochloride)) and a natural enzyme-responsive molecule (adenosine 5′-triphosphate). The superamphiphile self-assembles into spherical aggregates, which, upon addition of enzymes, disassemble and release loaded molecules (see picture).

    7. Nanoparticle Oscillators

      Nanoparticle Oscillations and Fronts (pages 8616–8619)

      Dr. István Lagzi, Dr. Bartlomiej Kowalczyk, Dawei Wang and Prof. Bartosz A. Grzybowski

      Article first published online: 30 SEP 2010 | DOI: 10.1002/anie.201004231

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      Rhythmic nanoparticles: Chemical oscillations can be coupled to the dynamic self-assembly of nanoparticles. Periodic pH changes translate into protonation and deprotonation of the ligands that stabilize the nanoparticles, thus altering repulsive and attractive interparticle forces. In a continuous stirred-tank reactor, rhythmic aggregation and dispersion is observed; in spatially distributed media, propagation of particle aggregation fronts is seen.

    8. Drug Delivery

      Facile Two-Step Synthesis of Porous Antigen-Loaded Degradable Polyelectrolyte Microspheres (pages 8620–8624)

      Marijke Dierendonck, Dr. Stefaan De Koker, Prof. Dr. Claude Cuvelier, Prof. Dr. Johan Grooten, Prof. Dr. Chris Vervaet, Prof. Dr. Jean-Paul Remon and Dr. Bruno G. De Geest

      Article first published online: 4 OCT 2010 | DOI: 10.1002/anie.201001046

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      Pore medicine: Porous antigen-loaded degradable polyelectrolyte microspheres are produced in a straightforward way providing high encapsulation efficiencies and efficient internalization by antigen-presenting cells. This system could find application as multilayer capsules in gene and drug delivery and for enzymatic microreactors.

    9. Microfluidic Synthesis

      Synchronized Synthesis of Peptide-Based Macrocycles by Digital Microfluidics (pages 8625–8629)

      Mais J. Jebrail, Alphonsus H. C. Ng, Dr. Vishal Rai, Dr. Ryan Hili, Prof. Andrei K. Yudin and Prof. Aaron R. Wheeler

      Article first published online: 16 AUG 2010 | DOI: 10.1002/anie.201001604

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      Digital synthesis has been applied to the formation of peptide-based macrocycles and their analogues with side chains appended during late-stage aziridine ring-opening. Discrete nanoliter- to microliter-sized droplets of samples and reagents are controlled in parallel by applying a series of electrical potentials to an array of electrodes coated with a hydrophobic insulator.

    10. Metal–Organic Frameworks

      Metal–Organic Frameworks from Edible Natural Products (pages 8630–8634)

      Dr. Ronald A. Smaldone, Dr. Ross S. Forgan, Dr. Hiroyasu Furukawa, Dr. Jeremiah J. Gassensmith, Prof. Alexandra M. Z. Slawin, Prof. Omar M. Yaghi and Prof. J. Fraser Stoddart

      Article first published online: 16 AUG 2010 | DOI: 10.1002/anie.201002343

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      Let them eat MOFs: Take a spoonful of sugar (γ-cyclodextrin to be precise), a pinch of salt (most alkali metal salts will suffice), and a swig of alcohol (Everclear fits the bill), and you have a robust, renewable, nanoporous (Langmuir surface area 1320 m2 g−1) metal–organic framework for breakfast (CD-MOF-1; see picture, C gray, O red, K purple; yellow sphere: pore).

    11. Quadrupole Interactions

      Highly Specific Heterodimerization Mediated by Quadrupole Interactions (pages 8635–8639)

      Hong Zheng and Prof. Jianmin Gao

      Article first published online: 2 AUG 2010 | DOI: 10.1002/anie.201002860

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      Quadrupole rules! The quadrupole stacking between aromatic and perfluoroaromatic rings is able to direct specific protein–protein interactions, resulting in the exclusive formation of heterodimers upon mixing a pair of homodimers with aromatic and perfluoroaromatic cores.

    12. Nanodiamond Catalysts

      Surface Chemistry and Catalytic Reactivity of a Nanodiamond in the Steam-Free Dehydrogenation of Ethylbenzene (pages 8640–8644)

      Prof. Jian Zhang , Prof. Dang Sheng Su , Raoul Blume, Prof. Robert Schlögl, Dr. Rui Wang, Prof. Xiangguang Yang and Dr. Andreja Gajović

      Article first published online: 1 OCT 2010 | DOI: 10.1002/anie.201002869

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      Hard core: A hybrid catalyst system for dehydrogenation of ethylbenzene comprises nanoparticles consisting of nanodiamond cores and highly curved, defective graphene shells (see picture). The system exhibits high catalytic activity and selectivity over a long period of time. In contrast to industrial K-promoted Fe catalysts, steam decoking of the catalyst is not required.

    13. Charge Transfer

      Water-Switching of Spin Transitions Induced by Metal-to-Metal Charge Transfer in a Microporous Framework (pages 8645–8648)

      Dr. Tao Liu, Dr. Yan-Juan Zhang, Dr. Shinji Kanegawa and Prof. Osamu Sato

      Article first published online: 4 OCT 2010 | DOI: 10.1002/anie.201002881

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      Water-switchable charge transfer: The microporous hydrated phase {[Fe(Tp)(CN)3]2Co(bpe)}5 H2O shows spin transition induced by metal-to-metal charge transfer (MMCT), but no MMCT is observed in the corresponding dehydrated phase (see picture). Charge transfer can be reversibly switched through de- and rehydration. Tp=hydrotris(pyrazolyl)borate, bpe=1,2-bis(4-pyridyl)ethane. Fe green, Co orange, N blue, O red, C gray, B dark yellow.

    14. Medicinal Chemistry

      A Nanoparticle Size Series for In Vivo Fluorescence Imaging (pages 8649–8652)

      Dr. Zoran Popović, Dr. Wenhao Liu, Vikash P. Chauhan, Jungmin Lee, Cliff Wong, Dr. Andrew B. Greytak, Numpon Insin, Prof. Dr. Daniel G. Nocera, Prof. Dr. Dai Fukumura, Prof. Dr. Rakesh K. Jain and Prof. Dr. Moungi G. Bawendi

      Article first published online: 30 SEP 2010 | DOI: 10.1002/anie.201003142

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      A nanoparticle toolset was created within the size limits of 10–150 nm for probing size-dependent nanoparticle distribution in solid tumors. By using multiphoton intravital microscopy, the particles were tracked both spatially and temporally in the same tumor grown in a transparent window model.

    15. Thiamin Biosynthesis

      A “Radical Dance” in Thiamin Biosynthesis: Mechanistic Analysis of the Bacterial Hydroxymethylpyrimidine Phosphate Synthase (pages 8653–8656)

      Abhishek Chatterjee, Amrita B. Hazra, Sameh Abdelwahed, David G. Hilmey and Prof. Tadhg P. Begley

      Article first published online: 30 SEP 2010 | DOI: 10.1002/anie.201003419

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      Tricky things with ThiC: Hydroxymethylpyrimidine phosphate (HMP-P) synthase (ThiC) catalyzes one of the most complex rearrangement reactions in primary metabolism. Deuteration experiments show that under reducing conditions, in the presence of aminoimidazole ribonucleotide, the 5′-deoxyadenosyl radical generated at the active site of ThiC reacts directly with the substrate and performs two iterative hydrogen atom abstraction events to catalyze this rearrangement (see scheme; SAM=S-adenosylmethionine).

    16. Zeolites

      Insights into the Dealumination of Zeolite HY Revealed by Sensitivity-Enhanced 27Al DQ-MAS NMR Spectroscopy at High Field (pages 8657–8661)

      Zhiwu Yu, Dr. Anmin Zheng, Qiang Wang, Dr. Lei Chen, Dr. Jun Xu, Prof. Jean-Paul Amoureux and Dr. Feng Deng

      Article first published online: 7 OCT 2010 | DOI: 10.1002/anie.201004007

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      A zeolite dealumination mechanism is proposed on the basis of sensitivity-enhanced 27Al DQ-MAS NMR spectra (see picture), which revealed for the first time the detailed evolution of extra-framework aluminum (EFAL) species and the spatial proximities of various aluminum species in dealuminated HY zeolites. Three types of EFAL species in close proximity to framework aluminum were identified.

    17. Biosensors

      Fabrication of a Structure-Specific RNA Binder for Array Detection of Label-Free MicroRNA (pages 8662–8665)

      Jeong Min Lee, Hyunmin Cho and Prof. Dr. Yongwon Jung

      Article first published online: 4 OCT 2010 | DOI: 10.1002/anie.201004000

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      Like an antibody: A novel structure-specific RNA-binding protein was designed to stably and specifically bind to surface-bound microRNAs. By acting like an antibody, this RNA binder enabled the universal detection of hybridized microRNAs on array surfaces (see picture) without any enzymatic amplification or labeling reactions.

    18. Asymmetric Catalysis

      Enantioselective Intramolecular Aza-Michael Additions of Indoles Catalyzed by Chiral Phosphoric Acids (pages 8666–8669)

      Quan Cai, Chao Zheng and Prof. Dr. Shu-Li You

      Article first published online: 7 OCT 2010 | DOI: 10.1002/anie.201003919

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      Two ways to win: The title reaction has been realized using chiral phosphoric acid catalysts to provide the heterocyclic products in excellent yields and with high ee values. The polycyclic indoles were also constructed using an olefin cross-metathesis/intramolecular aza-Michael addition sequence.

    19. CO2 Fixation

      Copper-Catalyzed Direct Carboxylation of C[BOND]H Bonds with Carbon Dioxide (pages 8670–8673)

      Dr. Liang Zhang, Dr. Jianhua Cheng, Dr. Takeshi Ohishi and Prof. Dr. Zhaomin Hou

      Article first published online: 4 OCT 2010 | DOI: 10.1002/anie.201003995

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      Cooking with gas: Copper complexes serve as excellent catalysts for the direct carboxylation of aromatic heterocyclic C[BOND]H bonds with CO2, thereby offering an economical and environmentally benign process for the synthesis of heterocyclic carboxylic esters (see scheme; IPr=1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene). Some active intermediates of this reaction have been isolated and structurally characterized.

    20. C[BOND]H/N[BOND]H Bond Functionalization

      Carboxylation of N[BOND]H/C[BOND]H Bonds Using N-Heterocyclic Carbene Copper(I) Complexes (pages 8674–8677)

      Dr. Ine I. F. Boogaerts, Dr. George C. Fortman, Marc R. L. Furst, Dr. Catherine S. J. Cazin and Prof. Dr. Steven P. Nolan

      Article first published online: 30 SEP 2010 | DOI: 10.1002/anie.201004153

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      Greenhouse gas makes good: A simple copper-mediated protocol has been developed where N[BOND]H or C[BOND]H bonds can be directly functionalized using an easily prepared catalyst. The novel [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper(I) hydroxide, [Cu(IPr)(OH)], permits the facile activation and carboxylation of N[BOND]H and C[BOND]H bonds with pKa values of less than 27.7 (see scheme).

    21. Catalytic Asymmetric Synthesis

      Catalytic Asymmetric Aldol Equivalents in the Enantioselective Synthesis of the Apoptolidin C Aglycone (pages 8678–8681)

      Thomas R. Vargo, James S. Hale and Prof. Scott G. Nelson

      Article first published online: 30 SEP 2010 | DOI: 10.1002/anie.201004925

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      Aldol replacement: Catalytic asymmetric ketene–aldehyde cycloadditions provide surrogates for traditional aldol additions in an enantioselective synthesis of apoptolidinone C, the aglycone of the potent apoptosis regulator apoptolidin C. Eight of apoptolidinone C's ten stereocenters derive directly from these catalytic acetate or propionate aldol equivalents.

    22. Natural Products Synthesis

      Temporary Restraints To Overcome Steric Obstacles: An Efficient Strategy for the Synthesis of Mycalamide B (pages 8682–8685)

      John C. Jewett and Prof. Dr. Viresh H. Rawal

      Article first published online: 7 OCT 2010 | DOI: 10.1002/anie.201003361

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      Restrain and release: A one-pot Mukaiyama–Michael/epoxidation sequence introduced three stereocenters, an intramolecular isocyanate trapping produced a rigid 10-membered cyclic carbamate, and the selective opening of the cyclic carbamate was used to reveal the fully constructed natural product.

    23. Amination

      Palladium-Catalyzed Cross-Coupling of Aryl Chlorides and Tosylates with Hydrazine (pages 8686–8690)

      Rylan J. Lundgren and Prof. Dr. Mark Stradiotto

      Article first published online: 7 OCT 2010 | DOI: 10.1002/anie.201003764

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      Hydrazine is not a problem anymore: The title transformation is the first reaction to yield aryl hydrazines through the cross-coupling of aryl chlorides and tosylates with hydrazine. An appropriately designed palladium catalyst allows this reaction to proceed rapidly under mild conditions, and with excellent chemoselectivity (see scheme; Ad=adamantyl, Ts=4-toluenesulfonyl).

    24. Synthetic Methods

      Titanium-Mediated Synthesis of 1,4-Diketones from Grignard Reagents and Acyl Cyanohydrins (pages 8691–8694)

      Paul Setzer, Dr. Alice Beauseigneur, Dr. Morwenna S. M. Pearson-Long and Prof. Dr. Philippe Bertus

      Article first published online: 30 SEP 2010 | DOI: 10.1002/anie.201003923

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      Double duty: In the presence of titanium isopropoxide, Grignard reagents were found to react with acyl cyanohydrins to give substituted 5-hydroxy-1,4-diketones (see scheme). This new reaction involves a formal addition of a 1,2-dianion equivalent to both the ester and nitrile moieties.

    25. Nanowires

      Controlled Colloidal Growth of Ultrathin Single-Crystal ZnS Nanowires with a Magic-Size Diameter (pages 8695–8698)

      Dr. Zhengtao Deng, Prof. Dr. Hao Yan and Prof. Dr. Yan Liu

      Article first published online: 4 OCT 2010 | DOI: 10.1002/anie.201003952

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      Down to the thin wire: A facile colloidal chemistry method is demonstrated for the controlled growth of highly uniform ultrathin single-crystal ZnS nanowires with a magic-size diameter as low as 1.2 nm (see HRTEM image). These ultrathin nanowires could find broad use in sensors, photodetectors, and host materials for diluted magnetic semiconductors.

    26. Zeolite Membranes

      High-Performance Randomly Oriented Zeolite Membranes Using Brittle Seeds and Rapid Thermal Processing (pages 8699–8703)

      Won Cheol Yoo, Jared A. Stoeger, Pyung-Soo Lee, Prof. Michael Tsapatsis and Prof. Andreas Stein

      Article first published online: 30 SEP 2010 | DOI: 10.1002/anie.201004029

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      MFI zeolite membranes with high flux and high separation factors for xylene isomer separation were fabricated by combining several unique processing steps. These include 1) use of brittle seeds prepared by confined synthesis, 2) rubbing and leveling methods to obtain randomly oriented seed layers, 3) secondary hydrothermal growth to produce thin zeolite films, and 4) rapid thermal processing to remove structure-directing agents while minimizing crack formation (see picture; scale bar 500 nm).

    27. Heterocyclic Carbenes

      1,3-Dipole Behavior of Phosphagermaallene Tip(tBu)Ge[DOUBLE BOND]C[DOUBLE BOND]PMes* Leading to a Phosphagermaheterocyclic Carbene (pages 8704–8707)

      Dr. Dumitru Ghereg, Dr. Erwan André, Dr. Jean-Marc Sotiropoulos, Dr. Karinne Miqueu, Prof. Dr. Heinz Gornitzka and Dr. Jean Escudié

      Article first published online: 10 SEP 2010 | DOI: 10.1002/anie.201003044

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      A cyclic phosphagermacarbene is formed by a [3+2] cycloaddition between the 1,3-dipolar Ge[DOUBLE BOND]C[DOUBLE BOND]P unit of a phosphagermaallene and an acetylene (see scheme; Tip=2,4,6-iPr3C6H3). The carbene undergoes C[BOND]H insertion or is trapped by a second equivalent of acetylene derivative, and its existence and reactivity was supported by DFT calculations.

    28. Hydrogen Storage

      Catalytic Solvolysis of Ammonia Borane (pages 8708–8711)

      Dr. Todd W. Graham, Dr. Chi-Wing Tsang, Xuanhua Chen, Dr. Rongwei Guo, Dr. Wenli Jia, Dr. Shui-Ming Lu, Dr. Christine Sui-Seng, Charles B. Ewart, Dr. Alan Lough, Dr. Dino Amoroso and Dr. Kamaluddin Abdur-Rashid

      Article first published online: 4 OCT 2010 | DOI: 10.1002/anie.201003074

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      Hydrogen on tap: A homogeneous catalyst system for the rapid and quantitative solvolysis of ammonia borane (AB) has been developed. The iridium catalyst is remarkably stable and can be reused with no observable degradation in activity. In the absence of solvent, the mixture of catalyst and AB efficiently generates hydrogen upon exposure to water vapor, thereby resulting in a system with considerable hydrogen storage capacity (see picture).

    29. Synthetic Methods

      Regioselective Nickel-Catalyzed Reductive Couplings of Enones and Allenes (pages 8712–8716)

      Wei Li, Nan Chen and Prof. John Montgomery

      Article first published online: 7 OCT 2010 | DOI: 10.1002/anie.201004740

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      Alkenes made easy: In a complement to coupling processes of terminal alkynes, the reductive coupling of enones and allenes provides access to conjugate addition products that possess a 1,1-disubstituted alkene (see scheme; cod=1,5-cyclooctadiene). The solvent composition and reducing agent must be carefully matched to allow high levels of regioselectivity to be observed.

    30. C[BOND]F Activation

      Nickel-Catalyzed Cyclization of Difluoro-Substituted 1,6-Enynes with Organozinc Reagents through the Stereoselective Activation of C[BOND]F Bonds: Synthesis of Bicyclo[3.2.0]heptene Derivatives (pages 8717–8720)

      Manabu Takachi, Dr. Yusuke Kita, Dr. Mamoru Tobisu, Dr. Yoshiya Fukumoto and Prof. Dr. Naoto Chatani

      Article first published online: 2 NOV 2010 | DOI: 10.1002/anie.201004543

      Thumbnail image of graphical abstract

      Quite a gem: A nickel-catalyzed cyclization of 1,6-enynes, bearing a gem-difluoro group at the olefinic terminus, with organozinc reagents gives the title compounds (see scheme). One of the fluorine atoms is stereoselectively replaced by the R′ group of R′2Zn, indicating the involvement of the stereoselective activation of a C–F bond.

    31. Radical Reactions

      Oxidation of Alkyl Trifluoroborates: An Opportunity for Tin-Free Radical Chemistry (pages 8721–8723)

      Dr. Geoffroy Sorin, Dr. Rocio Martinez Mallorquin, Yohan Contie, Alexandre Baralle, Prof. Dr. Max Malacria, Dr. Jean-Philippe Goddard and Prof. Dr. Louis Fensterbank

      Article first published online: 7 OCT 2010 | DOI: 10.1002/anie.201004513

      Thumbnail image of graphical abstract

      Organotrifluoroborates have been oxidized by copper(II) salts and Dess–Martin periodinane via radical intermediates, as evidenced by TEMPO spin-trapping experiments. This new method of radical generation is compatible with functionalization and C[BOND]C bond formation through Giese-type addition reactions (see scheme; DMSO=dimethyl sulfoxide, TEMPO=2,2,6,6-tetramethyl-1-piperidinyloxyl, free radical).

    32. Fluoro Sugars

      Fluorine-Directed Glycosylation (pages 8724–8728)

      Christoph Bucher and Prof. Dr. Ryan Gilmour

      Article first published online: 30 SEP 2010 | DOI: 10.1002/anie.201004467

      Thumbnail image of graphical abstract

      Everything's under control: A stabilizing fluorine electrostatic interaction has been exploited to control oxonium ion conformation in 2-fluoropyranose derivatives (see scheme). When matched with the inductive nature of the protecting groups, the glycosyl donors were found to be highly selective (2-FGluc/benzyl [RIGHTWARDS ARROW] β; 2-FManno/pivaloyl [RIGHTWARDS ARROW] α) leading to fluoro-glycostructures with excellent control over the anomeric configuration.

    33. C[BOND]H Activation

      A General Strategy Toward Aromatic 1,2-Ambiphilic Synthons: Palladium-Catalyzed ortho-Halogenation of PyDipSi-Arenes (pages 8729–8732)

      Alexander S. Dudnik, Natalia Chernyak, Chunhui Huang and Prof. Vladimir Gevorgyan

      Article first published online: 30 SEP 2010 | DOI: 10.1002/anie.201004426

      Thumbnail image of graphical abstract

      A general and efficient strategy to synthesize 1,2-ambiphilic aromatic and heteroaromatic synthons from haloarenes has been developed. The method involves installation of the PyDipSi directing group, and subsequent palladium-catalyzed directed ortho-halogenation of aryl silanes (see scheme; Py=2-pyridyl). The usefulness of these 1,2-ambiphilic building blocks was shown in their participation as both nucleophilic aryl silane and electrophilic aryl iodide moieties.

    34. Asymmetric Catalysis

      Catalytic Asymmetric Dihydroxylation of Enamides and Application to the Total Synthesis of (+)-Tanikolide (pages 8733–8737)

      Benoit Gourdet and Dr. Hon Wai Lam

      Article first published online: 30 SEP 2010 | DOI: 10.1002/anie.201004328

      Thumbnail image of graphical abstract

      Asymmetric dihydroxylation of β,β′- disubstituted enamides afforded chiral tertiary-alcohol-containing α-hydroxyaldehydes and 1,2-diols with high enantioselectivity (see scheme). This method was applied to the total synthesis of the antifungal natural product (+)-tanikolide, as well as the synthesis of an intermediate en route to (S)-oxybutynin.

    35. Lithium-Ion Batteries

      Scalable Synthesis of Tavorite LiFeSO4F and NaFeSO4F Cathode Materials (pages 8738–8742)

      Rajesh Tripathi, T. N. Ramesh, Brian L. Ellis and Prof. Linda F. Nazar

      Article first published online: 12 OCT 2010 | DOI: 10.1002/anie.201003743

      Thumbnail image of graphical abstract

      Single-phase tavorite, LiFeSO4F, is crystallized in tetraethylene glycol at 220 °C to give an electrochemically highly active material. This route obviates the need for expensive ionic liquids and can be extended to the synthesis of NaFeSO4F, whose structure solution, along with that of the parent framework FeSO4F, provides understanding of ion mobility.

    36. Hybrid Drugs

      Combining Independent Drug Classes into Superior, Synergistically Acting Hybrid Molecules (pages 8743–8746)

      Dr. Andreas Müller-Schiffmann, Dr. Julia März-Berberich, Dr. Aksana Andreyeva, Dr. Raik Rönicke, Dr. Dirk Bartnik, Dr. Oleksandr Brener, Dr. Janine Kutzsche, Dr. Anselm H. C. Horn, Dipl.-Chem. Marco Hellmert, Dr. Jolanta Polkowska, Prof. Dr. Kurt Gottmann, Prof. Dr. Klaus G. Reymann, Dr. S. Aileen Funke, Dr. Luitgart Nagel-Steger, Dr. Christine Moriscot, Prof. Dr. Guy Schoehn, Prof. Dr. Heinrich Sticht, Prof. Dr. Dieter Willbold, Prof. Dr. Thomas Schrader and Prof. Dr. Carsten Korth

      Article first published online: 4 OCT 2010 | DOI: 10.1002/anie.201004437

      Thumbnail image of graphical abstract

      More than the sum of its parts: Novel hybrid compounds consisting of an organic β-sheet-breaking moiety and a signaling, D-enantiomeric Aβ-recognizing peptide moiety have been designed (see picture). The compounds, which were chemically synthesized and characterized by several techniques, combine rational design and drug selection from libraries and inhibit Aβ oligomerization and Aβ-induced synaptic pathology.

    37. Zwitterionic Vesicles

      pH-Switchable Vesicles from a Serine-Derived Guanidiniocarbonyl Pyrrole Carboxylate Zwitterion in DMSO (pages 8747–8750)

      Fabian Rodler, Jürgen Linders, Tassilo Fenske, Dr. Thomas Rehm, Prof. Dr. Christian Mayer and Prof. Dr. Carsten Schmuck

      Article first published online: 30 SEP 2010 | DOI: 10.1002/anie.201003405

      Thumbnail image of graphical abstract

      Tightly closed: Zwitterion 1 forms vesicles that have an approximate size of 50 nm in DMSO solution. The vesicles can be opened and closed by the addition of either acid or base, as vesicle formation depends on the protonation state of zwitterion 1 (see picture). The membrane permeability of the vesicles is surprisingly low: the encapsulated solvent does not exchange with the surrounding solution, even on a time scale of a few hundred milliseconds.

    38. Olefin Polymerization

      Hydridoboranes as Modifiers for Single-Site Organochromium Catalysts: From Low- to Ultrahigh-Molecular-Weight Polyethylene (pages 8751–8754)

      Dr. Stefan Mark, Dr. Alexander Kurek, Prof. Dr. Rolf Mülhaupt, Dr. Rong Xu, Dr. Günter Klatt, Prof. Dr. Horst Köppel and Prof. Dr. Markus Enders

      Article first published online: 7 OCT 2010 | DOI: 10.1002/anie.201003918

      Thumbnail image of graphical abstract

      Going to great lengths: The use of hydridoboranes as new modifiers for chromium-catalyzed olefin polymerization allows the preparation of polyethylene with a precisely tunable ultrahigh molecular weight. This effect can be understood by a reversible protection of the active catalyst by the borane (see scheme).

    39. Functional Protein Structure

      The Distribution of Fatty Acids Reveals the Functional Structure of Human Serum Albumin (pages 8755–8759)

      Matthias J. N. Junk, Prof. Dr. Hans Wolfgang Spiess and Dr. Dariush Hinderberger

      Article first published online: 30 SEP 2010 | DOI: 10.1002/anie.201003495

      Thumbnail image of graphical abstract

      Flexible on the outside: The functional structure of the transport protein in human blood, human serum albumin (HSA), was characterized by distance measurements with double electron–electron resonance (DEER) spectroscopy on spin-labeled fatty acids that are bound to HSA. The functional protein structure derived has a more rigid inner core, while the surface of the protein shows much greater structural flexibility.

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      Article first published online: 3 NOV 2010 | DOI: 10.1002/anie.201090148

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