Angewandte Chemie International Edition

Cover image for Vol. 51 Issue 9

February 27, 2012

Volume 51, Issue 9

Pages 1979–2252

  1. Cover Picture

    1. Top of page
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    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. Flashback
    8. Corrigendum
    9. News
    10. Author Profile
    11. News
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
    17. Preview
    1. Cover Picture: Octahedral Pd2+ Coordination and Ferromagnetic Ordering in Pd(S2O7) (Angew. Chem. Int. Ed. 9/2012) (page 1979)

      M. Sc. Jörn Bruns, Dipl.-Chem. Matthias Eul, Prof. Dr. Rainer Pöttgen and Prof. Dr. Mathias S. Wickleder

      Article first published online: 16 DEC 2011 | DOI: 10.1002/anie.201108616

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      Oxidation of elemental palladium ;at elevated temperatures leads to the blue disulfate Pd(S2O7), which has an octahedral and not the usual square-planar coordination of a Pd2+ center. In their Communication on page 2204 ff., M. S. Wickleder, R. Pöttgen, and co-workers show that this rare coordination leads to paramagnetic behavior and that ferromagnetic ordering occurs at low temperature. This is the first example for this phenomenon in an oxidic Pd2+ compound.

  2. Inside Cover

    1. Top of page
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    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. Flashback
    8. Corrigendum
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    10. Author Profile
    11. News
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
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    1. Inside Cover: A Synthetic Approach Toward a Self-Regulated Insulin Delivery System (Angew. Chem. Int. Ed. 9/2012) (page 1980)

      Dr. Akira Matsumoto, Dr. Takehiko Ishii, Junko Nishida, Dr. Hiroko Matsumoto, Dr. Kazunori Kataoka and Dr. Yuji Miyahara

      Article first published online: 23 DEC 2011 | DOI: 10.1002/anie.201108617

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      A totally synthetic artificial pancreas is described by Y. Miyahara et al. in their Communication on page 2124 ff. A hydrogel bearing a phenylboronate derivative undergoes a glucose-dependent transition in its state of hydration under physiological conditions. The reversible surface-localized dehydration enables the provision of insulin to be controlled, thus offering a new basis for the treatment of diabetes with long-term stability and safety.

  3. Inside Back Cover

    1. Top of page
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    5. Back Cover
    6. Graphical Abstract
    7. Flashback
    8. Corrigendum
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    10. Author Profile
    11. News
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
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    1. Inside Back Cover: Towards Quantitative Conversion of Microalgae Oil to Diesel-Range Alkanes with Bifunctional Catalysts (Angew. Chem. Int. Ed. 9/2012) (page 2253)

      Baoxiang Peng, Yuan Yao, Dr. Chen Zhao and Prof. Dr. Johannes A. Lercher

      Article first published online: 19 JAN 2012 | DOI: 10.1002/anie.201108371

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      Hydrocarbon biodiesel can be quantitatively achieved on Ni/HBeta zeolite from crude algae oil in batch or continuous-flow reactors. In their Communication on page 2072 ff., J. Lercher et al. describe the kinetics, reaction pathways, and fundamental chemistry of the elementary steps of the cascade hydrogenation reaction on algae oil. This approach opens new possibilities to produce sulfur-free high-grade green transportation fuels from microalgae on a large scale.

  4. Back Cover

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    6. Graphical Abstract
    7. Flashback
    8. Corrigendum
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    10. Author Profile
    11. News
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
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    1. Back Cover: Volatile Amphibian Pheromones: Macrolides from Mantellid Frogs from Madagascar (Angew. Chem. Int. Ed. 9/2012) (page 2254)

      Dennis Poth, Dr. Katharina C. Wollenberg, Prof. Dr. Miguel Vences and Prof. Dr. Stefan Schulz

      Article first published online: 17 JAN 2012 | DOI: 10.1002/anie.201109230

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      Volatile pheromones in frogs have been detected for the first time in the family Mantellidae from Madagascar. Previously only water-soluble pheromones had been found in amphibians. In their Communication on page 2187 ff., S. Schulz and co-workers show that the femoral ducts of the male frogs contain macrolides and secondary alcohols. These compounds, including structures such as gephyromantolid A, were identified and synthesized.

  5. Graphical Abstract

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    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
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    1. Graphical Abstract: Angew. Chem. Int. Ed. 9/2012 (pages 1983–1996)

      Article first published online: 22 FEB 2012 | DOI: 10.1002/anie.201290014

  6. Flashback

    1. Top of page
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    1. 50 Years Ago ... (page 1992)

      Article first published online: 22 FEB 2012 | DOI: 10.1002/anie.201200506

  7. Corrigendum

    1. Top of page
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    14. Minireview
    15. Review
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    1. You have free access to this content
      Corrigendum: Three-Dimensional Directed Self-Assembly of Peptide Nanowires into Micrometer-Sized Crystalline Cubes with Nanoparticle Joints (page 1996)

      Prerna Kaur, Dr. Yoshiaki Maeda, Andrew C. Mutter, Prof. Tadashi Matsunaga, Prof. Yujia Xu and Prof. Hiroshi Matsui

      Article first published online: 22 FEB 2012 | DOI: 10.1002/anie.201109223

      This article corrects:
  8. News

    1. Top of page
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    8. Corrigendum
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    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
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  9. Author Profile

    1. Top of page
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    6. Graphical Abstract
    7. Flashback
    8. Corrigendum
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    14. Minireview
    15. Review
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    1. Shuit-Tong Lee (page 2002)

      Article first published online: 19 JAN 2012 | DOI: 10.1002/anie.201107718

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      “My motto is to keep cool and be patient. The most important thing I learned from my students is no question is stupid …” This and more about Shuit-Tong Lee can be found on page 2002.

  10. News

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    14. Minireview
    15. Review
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  11. Book Review

    1. Top of page
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    14. Minireview
    15. Review
    16. Communications
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    1. Practical Synthetic Organic Chemistry. Reactions, Principles, and Techniques. Edited by Stéphane Caron. (pages 2004–2005)

      Victor Snieckus

      Article first published online: 20 JAN 2012 | DOI: 10.1002/anie.201108440

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      John Wiley & Sons, Hoboken, 2011. 872 pp., softcover, € 87.90.—ISBN 978-0470037331

  12. Highlights

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    7. Flashback
    8. Corrigendum
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    15. Review
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    1. Click Chemistry

      Unlocking the 1,2,3-Triazole Ring Using Mechanical Force (pages 2006–2007)

      Dr. Yuan Lin and Prof. Qian Wang

      Article first published online: 19 JAN 2012 | DOI: 10.1002/anie.201108044

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      K(l)ick it into reverse: Mechanical force (ultrasound) may be employed to promote a retrocycloaddition reaction of a 1,2,3-triazole to regenerate the parent azide and alkyne, a reaction that cannot be achieved by other means.

    2. Chiral Nanomaterials

      Chiral Nematic Mesoporous Carbons from Self-Assembled Nanocrystalline Cellulose (pages 2008–2010)

      Prof. Tewodros Asefa

      Article first published online: 24 JAN 2012 | DOI: 10.1002/anie.201107332

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      C-ing cellulose in a new light: The self-assembly of nanocrystalline cellulose (NCC) with tetraalkoxysilane produces a chiral nematic NCC–silica composite material, which upon carbonization, and then etching of the silica with dilute base solution produces a novel high surface area chiral nematic mesoporous carbon (see picture).

  13. Minireview

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    1. Protein–Protein Interactions

      Small-Molecule Stabilization of Protein–Protein Interactions: An Underestimated Concept in Drug Discovery? (pages 2012–2018)

      Dipl.-Bioinf. Philipp Thiel, Prof. Dr. Markus Kaiser and Dr. Christian Ottmann

      Article first published online: 3 FEB 2012 | DOI: 10.1002/anie.201107616

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      Doing it the other way round: The modulation of protein–protein interactions (PPIs) by small molecules has become increasingly popular over the last few decades. However, “modulation” has mainly been perceived as “inhibition” of protein–protein interactions, omitting the complementary strategy of stabilizing such macromolecular complexes. This Minireview highlights amazing examples and the potential of this constructive side of modulating PPIs.

  14. Review

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    1. Organic Solar Cells

      Small Molecule Organic Semiconductors on the Move: Promises for Future Solar Energy Technology (pages 2020–2067)

      Dr. Amaresh Mishra and Prof. Dr. Peter Bäuerle

      Article first published online: 17 FEB 2012 | DOI: 10.1002/anie.201102326

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      Energy from molecules: Solar cells incorporating small molecules and oligomers as light-absorbing materials are presented in this Review, in which structure–property–efficiency correlations are discussed for a vast number of organic semiconducting materials. These properties should help in the design of new and highly efficient materials.

  15. Communications

    1. Top of page
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    1. Polymerization

      Synthesis of 5-Alkyl[3,4-c]thienopyrrole-4,6-dione-Based Polymers by Direct Heteroarylation (pages 2068–2071)

      Philippe Berrouard, Dr. Ahmed Najari, Dr. Agnieszka Pron, David Gendron, Pierre-Olivier Morin, Jean-Rémi Pouliot, Justine Veilleux and Prof. Dr. Mario Leclerc

      Article first published online: 11 NOV 2011 | DOI: 10.1002/anie.201106411

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      Don't stand Stille: A direct heteroarylation polycondensation reaction was used for the synthesis of high-molecular-weight thienopyrroledione-based polymers (see scheme) in an impressive yield (up to 96 %) and in only a few synthetic steps. This new method is an alternative to the standard Stille coupling reaction and thus avoids formation of toxic tin by-products.

    2. Biofuels

      Towards Quantitative Conversion of Microalgae Oil to Diesel-Range Alkanes with Bifunctional Catalysts (pages 2072–2075)

      Baoxiang Peng, Yuan Yao, Dr. Chen Zhao and Prof. Dr. Johannes A. Lercher

      Article first published online: 15 NOV 2011 | DOI: 10.1002/anie.201106243

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      Diesel oil from microalgae oil: An approach for selective conversion of crude microalgae oil to diesel-range alkanes is reported using Ni nanoclusters supported on zeolite catalysts (see picture). The cascade of catalyzed reactions for microalgae oil conversion is based on a metal-catalytic function for the integrated hydrogenolysis, hydrogenation, and decarbonylation as well as an acid-catalytic function for dehydration and isomerization.

    3. Composite Aerogels

      Cellulose–Silica Nanocomposite Aerogels by In Situ Formation of Silica in Cellulose Gel (pages 2076–2079)

      Dr. Jie Cai, Shilin Liu, Jiao Feng, Satoshi Kimura, Masahisa Wada, Prof. Dr. Shigenori Kuga and Prof. Lina Zhang

      Article first published online: 24 JAN 2012 | DOI: 10.1002/anie.201105730

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      Light support: Regenerated cellulose gel prepared from an aqueous alkali–urea solution serves as scaffold/template for the in situ preparation of cellulose–silica composite aerogels (see picture) by a sol–gel process from organic silicates, and drying with supercritical CO2. The resulting composite aerogels have the mechanical strength and flexibility, large surface area, semi-transparency, and low thermal conductivity of the cellulose aerogels.

    4. Micellar Effect

      Substrate-Selective Dehydrocondensation at the Interface of Micelles and Emulsions of Common Surfactants (pages 2080–2083)

      Prof. Dr. Munetaka Kunishima, Kanako Kikuchi, Yukio Kawai and Dr. Kazuhito Hioki

      Article first published online: 20 JAN 2012 | DOI: 10.1002/anie.201107706

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      Scratch the surface: Dehydrocondensations between carboxylates and amines by using an amphiphilic 1,3,5-triazinylammonium-based coupling agent were accelerated by the interfacial effect of micelles and emulsions of common surfactants (see figure). The reaction of carboxylates was promoted by both anionic and nonionic surfactants, and that of amines was promoted by only a nonionic surfactant. High selectivities for more lipophilic substrates were observed in micelles or emulsions.

    5. Asymmetric Synthesis

      Bifunctional Organocatalytic Strategy for Inverse-Electron-Demand Diels–Alder Reactions: Highly Efficient In Situ Substrate Generation and Activation to Construct Azaspirocyclic Skeletons (pages 2084–2087)

      Dr. Xianxing Jiang, Xiaomei Shi, Shoulei Wang, Tao Sun, Dr. Yiming Cao and Prof. Dr. Rui Wang

      Article first published online: 23 JAN 2012 | DOI: 10.1002/anie.201107716

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      Skeletons in the flask: The first highly enantioselective organocatalytic version of the title reaction using an in situ substrate generation/activation catalytic mode is described (see scheme). The reaction provides an efficient enantioselective construction of functionalized azaspirocyclic skeletons. The in situ generation of the enolate provides a new way in which to use this important nucleophile in organic synthesis.

    6. Energy Transfer

      Artificial Light-Harvesting System Based on Multifunctional Surface-Cross-Linked Micelles (pages 2088–2092)

      Hui-Qing Peng, Dr. Yu-Zhe Chen, Prof. Yan Zhao, Prof. Qing-Zheng Yang, Prof. Li-Zhu Wu, Prof. Chen-Ho Tung, Prof. Li-Ping Zhang and Prof. Qing-Xiao Tong

      Article first published online: 26 JAN 2012 | DOI: 10.1002/anie.201107723

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      A good harvest: Two self-assembling strategies (micellization and electrostatic attraction) and covalent capture were employed to construct a robust, inexpensive, efficient artificial light-harvesting system (see picture). The synthesis was achieved by a one-pot reaction. A high density of the antenna chromophores was achieved without self-quenching and excimer formation, thus affording extremely efficient energy transfer.

    7. Asymmetric Catalysis

      Relay Catalysis Using a Rhodium Complex/Chiral Brønsted Acid Binary System: Enantioselective Reduction of a Carbonyl Ylide as the Reactive Intermediate (pages 2093–2097)

      Prof. Dr. Masahiro Terada and Yasunori Toda

      Article first published online: 19 JAN 2012 | DOI: 10.1002/anie.201107805

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      Pass the baton: A one-pot relay catalysis for a carbonyl ylide formation/enantioselective reduction sequence using a dirhodium(II) tetracarboxylate and chiral phosphoric acid catalyst system is described. The four-step transformation involves a rhodium carbene complex, a carbonyl ylide, and an isobenzopyrylium intermediate, the enantioselective reduction of which yields isochromanone derivatives in good yield with high selectivity.

    8. N-Heterocyclic Carbenes

      Beryllium-Induced C[BOND]N Bond Activation and Ring Opening of an N-Heterocyclic Carbene (pages 2098–2100)

      Dr. Merle Arrowsmith, Prof. Michael S. Hill, Dr. Gabriele Kociok-Köhn, Dr. Dugald J. MacDougall and Dr. Mary F. Mahon

      Article first published online: 20 JAN 2012 | DOI: 10.1002/anie.201107836

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      Berylliant! Interaction of a well-defined adduct of MeBeH and an N-heterocyclic carbene (NHC) with PhSiH3 results in complete rupture of the heterocycle, and activation of the NHC through effective BeH2 insertion into a C[BOND]N bond of the heterocycle (see scheme; Ar=2,6-diisopropylphenyl, IPr=1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene).

    9. Coordination Chemistry

      Observation of the Highest Coordination Number in Planar Species: Decacoordinated Ta©B10 and Nb©B10 Anions (pages 2101–2105)

      Timur R. Galeev, Dr. Constantin Romanescu, Wei-Li Li, Prof. Dr. Lai-Sheng Wang and Prof. Dr. Alexander I. Boldyrev

      Article first published online: 1 FEB 2012 | DOI: 10.1002/anie.201107880

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      Molecular wheels: Decacoordinated molecular wheels, Ta©B10 (see picture) and Nb©B10, showing the highest coordination number for the central atom in a planar environment at present, were produced in a laser-vaporization supersonic molecular beam and characterized by photoelectron spectroscopy and ab initio calculations. The highly symmetric Ta©B10 and Nb©B10 anions are doubly aromatic with six delocalized π electrons and ten delocalized σ electrons.

    10. Asymmetric Catalysis

      Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation of Allylic Alcohols by an Enantioselective Isomerization/Transfer Hydrogenation Mechanism (pages 2106–2110)

      Ruoqiu Wu, Marie G. Beauchamps, Joseph M. Laquidara and Prof. John R. Sowa Jr.

      Article first published online: 20 JAN 2012 | DOI: 10.1002/anie.201107910

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      Reducing hazards: A asymmetric transfer hydrogen reaction was developed to reduce prochiral allylic alcohols in high yield and excellent enantioselectivity (see example). Mechanistic studies indicate a novel enantioselective isomerization/transfer hydrogenation mechanism. This new reaction is much safer than high-pressure hydrogenation using H2 gas.

    11. Natural Product Synthesis

      A Formal Synthesis of Vinigrol (pages 2111–2114)

      Jason Poulin, Christiane M. Grisé-Bard and Prof. Louis Barriault

      Article first published online: 19 JAN 2012 | DOI: 10.1002/anie.201108779

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      Two key reactions in a rapid assembly of the tricyclic core of vinigrol are a stereoselective Claisen rearrangement and an intramolecular Diels–Alder reaction. The method paves the way for a total synthesis of this synthetically challenging and biologically interesting natural product.

    12. Polyoxometalates

      Nanoscale Growth of Molecular Oxides: Assembly of a {V6} Double Cubane Between Two Lacunary {P2W15} Polyoxometalates (pages 2115–2118)

      Claire Lydon, Dr. Christoph Busche, Dr. Haralampos N. Miras, Dr. Alexander Delf, Dr. De-Liang Long, Prof. Lesley Yellowlees and Prof. Leroy Cronin

      Article first published online: 1 FEB 2012 | DOI: 10.1002/anie.201105829

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      POM-in-POM: A Wells–Dawson polyoxometalate sandwich compound with a double cubane core consisting of six vanadium atoms has been synthesized (see structure). Cluster formation was followed by mass spectrometry and the reduction of the double cubane was studied by a novel technique combining mass spectrometry and spectroelectrochemistry.

    13. Water Clusters

      Supramolecular Encapsulation of Tetrahedrally Hydrated Guests in a Tetrahedron Host (pages 2119–2123)

      Dr. Qi-Qiang Wang, Dr. Victor W. Day and Prof. Kristin Bowman-James

      Article first published online: 24 JAN 2012 | DOI: 10.1002/anie.201106090

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      A tricyclic organic host with tetrahedrally positioned amines incorporates a tetrahedron of water in the solid state. This internal water layer further solvates either an additional water molecule or a fluoride ion (see picture). The five-water cluster is an example the simple model for bulk water known as Walrafen's pentamer.

    14. Insulin Delivery Gel

      A Synthetic Approach Toward a Self-Regulated Insulin Delivery System (pages 2124–2128)

      Dr. Akira Matsumoto, Dr. Takehiko Ishii, Junko Nishida, Dr. Hiroko Matsumoto, Dr. Kazunori Kataoka and Dr. Yuji Miyahara

      Article first published online: 9 DEC 2011 | DOI: 10.1002/anie.201106252

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      Protein-free: A hydrogel containing phenylboronate was optimized so as to undergo rapid glucose-dependent changes in the state of hydration under physiological aqueous conditions. A localized dehydration of the gel surface to form a “skin layer” enabled control of the release of insulin from the gel. This dehydration is induced by fluctuations in the glucose concentration in the range between normo- and hyperglycemia.

    15. Porous Catalysts

      One-Pot Aerosol Route to MoO3-SiO2-Al2O3 Catalysts with Ordered Super Microporosity and High Olefin Metathesis Activity (pages 2129–2131)

      Dr. Damien P. Debecker, Dr. Mariana Stoyanova, Fréderic Colbeau-Justin, Dr. Uwe Rodemerck, Dr. Cédric Boissière, Prof. Eric M. Gaigneaux and Prof. Clément Sanchez

      Article first published online: 19 JAN 2012 | DOI: 10.1002/anie.201106277

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      Aerosol processing coupled with surfactant-templated sol–gel synthesis is used to produce MoO3-SiO2-Al2O3 catalysts. By quenching the sol–gel kinetics by fast drying of the aerosol, molecular-scale dispersion of each component is achieved. The structuring agent generates an organized porosity at the nanoscale. The catalysts have a high specific surface area and outstanding olefin metathesis activity.

    16. Photoresponsive Polymers

      Photocontrol of the Translocation of Molecules, Peptides, and Quantum Dots through Cell and Lipid Membranes Doped with Azobenzene Copolymers (pages 2132–2136)

      Dr. Sarra C. Sebai, Dimitra Milioni, Dr. Astrid Walrant, Dr. Isabel D. Alves, Dr. Sandrine Sagan, Dr. Cécile Huin, Dr. Loic Auvray, Dominique Massotte, Prof. Sophie Cribier and Dr. Christophe Tribet

      Article first published online: 19 JAN 2012 | DOI: 10.1002/anie.201106777

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      Light opens: Photocontrolled transmembrane passage of soluble dyes and delivery of small peptides into mammalian cells has been achieved using azobenzene-modified polymers (AMPs) as permeabilizing agents. Irradiation with UV and visible light triggers polarity switches upon cistrans isomerization of the azobenzene moieties. Photoresponsive permeability and pore opening promoted by trans-AMPs, but not cis-AMPs, in supported lipid bilayers are observed.

    17. Photoisomerization

      Reversible Heterochiral Aggregation/Dissociation of Bis(2-hydroxyphenyl)diamides Driven by UV/Vis Irradiation (pages 2137–2141)

      Akihiro Nojiri, Dr. Naoya Kumagai and Prof. Dr. Masakatsu Shibasaki

      Article first published online: 19 JAN 2012 | DOI: 10.1002/anie.201106832

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      Light to dissolve: (R)- and (S)-diamides bearing a hydrogen-bonding framework (red in picture) and a trans-azobenzene unit (blue) form an insoluble heterochiral aggregate, which can be dissolved by photoisomerization of the azobenzene unit to the cis conformation by UV irradiation (365 nm). The insoluble aggregate was formed again by subsequent irradiation with visible light (>422 nm). The precipitation and dissolution is manifestly reversible.

    18. Spin Crossover

      Crystallographic Evidence for Reversible Symmetry Breaking in a Spin-Crossover d7 Cobalt(II) Coordination Polymer (pages 2142–2145)

      Kishalay Bhar, Sumitava Khan, Dr. José Sánchez Costa, Prof. Joan Ribas, Dr. Olivier Roubeau, Partha Mitra and Prof. Barindra Kumar Ghosh

      Article first published online: 23 JAN 2012 | DOI: 10.1002/anie.201107116

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      All in a spin: A cobalt(II) coordination polymer has a highly cooperative spin-crossover (SCO) behavior with a small hysteresis loop (see picture; HS=high spin, LS=low spin). The correlation of the magnetic properties with the crystal structures was determined at different temperatures. This study reveals an unprecedented reversible symmetry breaking in a d7 SCO coordination polymer.

    19. Polymorphism

      High-Pressure (+)-Sucrose Polymorph (pages 2146–2150)

      Ewa Patyk, Julia Skumiel, Dr. Marcin Podsiadło and Prof. Andrzej Katrusiak

      Article first published online: 24 JAN 2012 | DOI: 10.1002/anie.201107283

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      Yes, Walter, there is a polymorph of sucrose! At 4.80 GPa, (+)-sucrose, common table sugar, transforms into a new polymorph. In its structure the network of intermolecular hydrogen bonds is reformulated, with new types of H bonds being formed, and the molecular conformation changes. This structural variability is characteristic of all carbohydrates, hinders their crystallization, and is vital for organisms for which sugars are important building blocks.

    20. Pattern Formation

      Unmasking Photolithography: A Versatile Way to Site-Selectively Pattern Gold Substrates (pages 2151–2154)

      Matthew J. Hynes and Prof. Joshua A. Maurer

      Article first published online: 23 JAN 2012 | DOI: 10.1002/anie.201107671

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      Surface chemistry: A new method for creating complex patterns on gold substrates is reported. Substrates were functionalized with nitroveratryl-protected carboxylic acid and hydroxy-terminated thiol monomers and patterned with a direct-write photolithography system to produce complex functional group gradients. In addition, two amine molecules were sequentially coupled on the substrate under spatial control (see picture).

    21. Alloy Clusters

      Ag7Au6: A 13-Atom Alloy Quantum Cluster (pages 2155–2159)

      Thumu Udayabhaskararao, Yan Sun, Nirmal Goswami, Samir K. Pal, K. Balasubramanian and Prof. Thalappil Pradeep

      Article first published online: 20 JAN 2012 | DOI: 10.1002/anie.201107696

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      An alloy cluster containing a 13-atom core, with a composition Ag7Au6(H2MSA)10 (H2MSA=mercaptosuccinic acid) was synthesized from silver clusters by a galvanic exchange reaction. The clusters were characterized by several spectroscopic and microscopic methods. The alloy cluster shows luminescence with a quantum yield of 3.5×10−2 at room temperature. Theoretical calculations for Ag7Au6(SCH3)10 suggest a distorted icosahedral core.

    22. Metal–Organic Frameworks

      Metal–Organic Frameworks Incorporating Copper-Complexed Rotaxanes (pages 2160–2163)

      Dr. Ali Coskun, Dr. Mohamad Hmadeh, Gokhan Barin, Dr. Felipe Gándara, Dr. Qiaowei Li, Eunwoo Choi, Nathan L. Strutt, Dr. David B. Cordes, Prof. Alexandra M. Z. Slawin, Prof. J. Fraser Stoddart, Prof. Jean-Pierre Sauvage and Prof. Omar M. Yaghi

      Article first published online: 20 JAN 2012 | DOI: 10.1002/anie.201107873

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      MOFs on the move: A copper-coordinated [2]pseudorotaxanate which reacts with zinc nitrate to form threefold interpenetrated networks retains most of its solution-state chemistry, including its ability to undergo electronic switching of some of the copper(I) ions under redox control.

    23. Nanoparticulate Anode

      Nanoparticulate TiO2(B): An Anode for Lithium-Ion Batteries (pages 2164–2167)

      Dr. Yu Ren, Zheng Liu, Dr. Frédérique Pourpoint, Dr. A. Robert Armstrong, Prof. Clare P. Grey and Prof. Peter G. Bruce

      Article first published online: 17 JAN 2012 | DOI: 10.1002/anie.201108300

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      Small but powerful: TiO2(B) with the smallest particle size yet reported (2.5×4.3 nm) has been synthesized (see TEM image). Its volumetric capacity to store lithium, and hence charge, as an anode in a lithium-ion battery is greater than that of any other titanate at high rates (>1000 mA g−1).

    24. Interlocked Molecules

      Molecular Shuttling of a Compact and Rigid H-Shaped [2]Rotaxane (pages 2168–2172)

      Dr. Kelong Zhu, V. Nicholas Vukotic and Prof. Stephen J. Loeb

      Article first published online: 19 JAN 2012 | DOI: 10.1002/anie.201108488

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      Push-button control: A new templating motif for mechanically interlocked molecules involving benzimidazolium axles and dibenzo[24]crown-8 wheels was used to create [2]rotaxane molecular shuttles with a compact and rigid, H-shaped molecular structure for condensed-phase and solid-state applications. Four different states of the molecular shuttle were shown to exhibit different rates of motion controlled by acid–base chemistry or the presence/absence of lithium ions (see scheme).

    25. Mesoporous Films

      Highly Ordered Mesoporous Silica Films with Perpendicular Mesochannels by a Simple Stöber-Solution Growth Approach (pages 2173–2177)

      Dr. Zhaogang Teng, Prof. Gengfeng Zheng, Dr. Yuqian Dou, Wei Li, Prof. Dr. Chung-Yuan Mou, Dr. Xuehua Zhang, Prof. Abdullah M. Asiri and Prof. Dongyuan Zhao

      Article first published online: 24 JAN 2012 | DOI: 10.1002/anie.201108748

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      A simple solution: In the simple approach to silica films with perpendicular mesochannels presented herein, the substrate is immersed into a Stöber solution in which the silica precursors are hydrolyzed, cross-linked by an ammonia catalyst, and assembled with a surfactant on the substrate to form hexagonal mesostructures perpendicular to the substrate surface.

    26. Cooperative Catalysis

      Tandem Rhodium-Catalyzed Hydroformylation–Hydrogenation of Alkenes by Employing a Cooperative Ligand System (pages 2178–2182)

      Daniela Fuchs, Dr. Géraldine Rousseau, Dr. Lisa Diab, Urs Gellrich and Prof. Dr. Bernhard Breit

      Article first published online: 30 JAN 2012 | DOI: 10.1002/anie.201108946

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      Dual action: A multifunctional rhodium catalyst system enables the simultaneous catalysis of two distinct transformations, hydroformylation of an alkene and reduction of an aldehyde, in a highly selective manner. This one-pot/two-step process is controlled by the cooperative action of two different supramolecular ligand systems and transforms terminal alkenes into C1-chain-elongated linear alcohols.

    27. Boron Ligands

      Planar Four-Coordinate Boron: A Single, Flat Boron Atom as a Ligand for Four Metals (pages 2183–2186)

      Prof. Dr. Holger Braunschweig, Dr. Rian D. Dewhurst, Dr. Katharina Kraft, Sebastian Östreicher and Dr. Krzysztof Radacki

      Article first published online: 17 JAN 2012 | DOI: 10.1002/anie.201107248

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      You may now kiss the boride: Four-coordinate boron, carbon, and nitrogen are almost always tetrahedral. The first examples of compounds with near-planar four-coordinate boron atoms have been prepared from trinuclear coordinatively unsaturated borido complexes. The two resultant tetranuclear complexes (see scheme) both feature near-planar four-coordinate boron atoms, with angle sums of 362.4° and 364.6°.

    28. Pheromones

      Volatile Amphibian Pheromones: Macrolides from Mantellid Frogs from Madagascar (pages 2187–2190)

      Dennis Poth, Dr. Katharina C. Wollenberg, Prof. Dr. Miguel Vences and Prof. Dr. Stefan Schulz

      Article first published online: 20 JAN 2012 | DOI: 10.1002/anie.201106592

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      Amphibians like water, but do they also notice volatile compounds in the air? Yes, they do. Macrolides, such as phoracantholide J (see picture; upper right structure) or the newly discovered natural product gephyromantolide A (left structure), are used for communication by mantelline frogs from Madagascar.

    29. Anion Binding

      Allosteric Binding of Halide Anions by a New Dimeric Interpenetrated Coordination Cage (pages 2191–2194)

      Sabrina Freye, Jakob Hey, Anna Torras-Galán, Prof. Dr. Dietmar Stalke, Dr. Regine Herbst-Irmer, Dr. Michael John and Prof. Dr. Guido H. Clever

      Article first published online: 17 JAN 2012 | DOI: 10.1002/anie.201107184

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      Packed in like sardines: Three BF4 ions are packed into the three cavities of an interpenetrated dimer of a coordination cage (see scheme). While the inner BF4 ion is tightly bound inside the central position, the loosely bound outer anions can be replaced with halide anions by an allosteric binding mechanism and a concerted structural change. In particular, Cl is bound with great affinity.

    30. Supramolecular NHC Complexes

      Stepwise Preparation of a Molecular Square from NR,NR- and NH,O-Substituted Dicarbene Building Blocks (pages 2195–2198)

      Markus Schmidtendorf, Tania Pape and Prof. Dr. F. Ekkehardt Hahn

      Article first published online: 27 JAN 2012 | DOI: 10.1002/anie.201107227

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      A molecular rectangle has been obtained from two equivalents of a dicarbene-bridged dinuclear platinum complex and two equivalents of β,β′-bis(triisopropylsiloxy)phenyl-1,4-diisocyanide. Hydrolysis of the O[BOND]Si(iPr)3 bonds in this complex leads to the formation of two bridging di(NH,O)-NHC ligands and yields the molecular square (see picture) that features two types of bridging rigid ditopic di-NHC ligands.

    31. Noble Metal Precursors

      Thermolabile Noble Metal Precursors: (NO)[Au(NO3)4], (NO)2[Pd(NO3)4], and (NO)2[Pt(NO3)6] (pages 2199–2203)

      Prof. Dr. Mathias S. Wickleder, Dr. Frauke Gerlach, Steffen Gagelmann, Jörn Bruns, Dr. Mandus Fenske and Prof. Dr. Katharina Al-Shamery

      Article first published online: 27 JAN 2012 | DOI: 10.1002/anie.201106107

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      Oxidizing noble metals: Pure N2O5 can oxidize elemental gold and palladium. The complex nitrates obtained by these reactions, (NO)[Au(NO3)4], (NO)2[Pd(NO3)4], and also the first nitrate of tetravalent platinum, (NO)2[Pt(NO3)6] (see picture for the anion: Pt gray, N green, O blue), have the potential to act as precursors owing to their high thermolability. The thermal decomposition of (NO)[Au(NO3)4] was elucidated in detail by several methods.

    32. [PdO6] Octahedra

      Octahedral Pd2+ Coordination and Ferromagnetic Ordering in Pd(S2O7) (pages 2204–2207)

      M. Sc. Jörn Bruns, Dipl.-Chem. Matthias Eul, Prof. Dr. Rainer Pöttgen and Prof. Dr. Mathias S. Wickleder

      Article first published online: 30 NOV 2011 | DOI: 10.1002/anie.201107197

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      It's hip not to be square: The oxidation of elemental palladium with SO3 leads to Pd(S2O7) in which the Pd2+ is in an octahedral coordination environment of oxygen atoms (see structure Pd red, O blue, S yellow) and not the usual square-planar environment for Pd2+ species. This unexpected geometry leads to the observed paramagnetism of the compound with ferromagnetic ordering at 11.7 K.

    33. Water-Stable Foldamers

      Unique α,β- and α,α,β,β-Peptide Foldamers Based on cis-β-Aminocyclopentanecarboxylic Acid (pages 2208–2212)

      Dr. Łukasz Berlicki, Ludwig Pilsl, Dr. Edit Wéber, Dr. István M. Mándity, Prof. Dr. Chiara Cabrele, Prof. Dr. Tamás A. Martinek, Prof. Dr. Ferenc Fülöp and Prof. Dr. Oliver Reiser

      Article first published online: 26 JAN 2012 | DOI: 10.1002/anie.201107702

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      Waterproof: cis-β-Aminocylopentanecarboxylic acid is a highly suitable building block for the synthesis of α,β- and α,α,β,β-peptides that have unique helical structures with high stability in methanol and aqueous media.

    34. Polymer Foams

      You have full text access to this OnlineOpen article
      Synthesis of Macroporous Polystyrene by the Polymerization of Foamed Emulsions (pages 2213–2217)

      Dr. Fabian Schüler, Debora Schamel, Dr. Anniina Salonen, Dr. Wiebke Drenckhan, Prof. Dr. Michael D. Gilchrist and Prof. Dr. Cosima Stubenrauch

      Article first published online: 20 JAN 2012 | DOI: 10.1002/anie.201107806

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      An ideal template for the production of macroporous polystyrene can be prepared from foamed oil-in-water emulsions containing styrene, water, glycerol, and sodium dodecylsulfate. After addition of a photoinitiator the mixture is polymerized with UV light and the foam structure of the precursor is transferred to the polymer. The resulting materials display densely packed cells with windows between adjacent pores (see SEM image; scale bar: 250 μm).

    35. Asymmetric C–F Activation

      Synthesis of the Smallest Axially Chiral Molecule by Asymmetric Carbon–Fluorine Bond Activation (pages 2218–2220)

      Dr. Moritz F. Kuehnel, Tobias Schlöder, Dr. Sebastian Riedel, Belén Nieto-Ortega, Prof. Dr. Francisco J. Ramírez, Prof. Dr. Juan T. López Navarrete, Prof. Dr. Juan Casado and Prof. Dr. Dieter Lentz

      Article first published online: 20 JAN 2012 | DOI: 10.1002/anie.201108105

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      Enantioselect-DeFluor: Carbon–fluorine bond cleavage by a chiral zirconium complex allows the synthesis of optically active 1,3-difluoroallene for the first time. Its absolute configuration was established by gas-phase vibrational circular dichroism spectroscopy (see picture).

    36. Influenza Viruses

      A Secondary Sialic Acid Binding Site on Influenza Virus Neuraminidase: Fact or Fiction? (pages 2221–2224)

      Jimmy C. C. Lai, Dr. Jean-Michel Garcia, Jeffrey C. Dyason, Raphael Böhm, Paul D. Madge, Faith J. Rose, Dr. John M. Nicholls, Prof. J. S. Malik Peiris, Dr. Thomas Haselhorst and Prof. Mark von Itzstein

      Article first published online: 26 JAN 2012 | DOI: 10.1002/anie.201108245

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      One flu over the cuckoo's nest: The biological significance of a secondary sialic acid binding site on influenza virus neuraminidase remains elusive. On blocking the active site influenza-virus-containing virus-like particles with oseltamivir carboxylate, binding to α(2,3)-sialyllactose is still detected. Thus the sialyllactose must bind at a secondary sialic acid binding site (see structures: docking study of α(2,3)-sialyllactose in the secondary binding site of avian flu neuraminidase).

    37. Synthetic Methods

      Palladium-Catalyzed Intermolecular C(sp3)[BOND]H Amidation (pages 2225–2228)

      Dr. Álvaro Iglesias, Prof. Dr. Rosana Álvarez, Prof. Dr. Ángel R. de Lera and Prof. Dr. Kilian Muñiz

      Article first published online: 1 FEB 2012 | DOI: 10.1002/anie.201108351

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      Dual capacity: A new palladium-catalyzed intermolecular sequence consisting of the C[BOND]H activation and amidation of methyl groups relies on N-fluorobis(phenylsulfonyl)imide (NFSI) as both the oxidant and the nitrogen source. The reaction provides the corresponding arylamines as bissulfonimides along with HF as the only by-product. Both experimental and computational results suggest the involvement of a monomeric palladium(IV) intermediate.

    38. Nanoparticle Catalysis

      Thermosensitive Au-PNIPA Yolk–Shell Nanoparticles with Tunable Selectivity for Catalysis (pages 2229–2233)

      Shuang Wu, Prof. Joachim Dzubiella, Julian Kaiser, Dr. Markus Drechsler, Prof. Xuhong Guo, Prof. Matthias Ballauff and Dr. Yan Lu

      Article first published online: 23 JAN 2012 | DOI: 10.1002/anie.201106515

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      Selectivity in nanoreactors: A hybrid yolk–shell nanostructure that contains gold nanoparticles in the core and thermosensitive microgel poly(N-isopropylacrylamide) (PNIPA) as shell is presented. The catalytic selectivity of Au-PNIPA nanoparticles for the reduction of hydrophilic 4-nitrophenol and more hydrophobic nitrobenzene with NaBH4 can be tuned through the volume transition of PNIPA shell (see picture).

    39. Biomimetic O2 Activation

      A Trispyrazolylborato Iron Cysteinato Complex as a Functional Model for the Cysteine Dioxygenase (pages 2234–2237)

      Dipl.-Chem. Madleen Sallmann, Dr. Inke Siewert, Dipl.-Chem. Lea Fohlmeister, Prof. Dr. Christian Limberg and Dr. Christina Knispel

      Article first published online: 27 JAN 2012 | DOI: 10.1002/anie.201107345

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      The natural paragon taken seriously: A trispyrazolylborato cysteinato iron complex not only excellently mimics the active site structure of cysteine dioxygenase (see picture: both structures superimposed): a dioxygenation of cysteinate occurs on treatment with O2, and hence, the system represents the hitherto most realistic model for cysteine dioxygenase.

    40. C[BOND]H Activation

      Chiral Monodentate Phosphines and Bulky Carboxylic Acids: Cooperative Effects in Palladium-Catalyzed Enantioselective C(sp3)–H Functionalization (pages 2238–2242)

      Tanguy Saget, Sébastien J. Lemouzy and Prof. Dr. Nicolai Cramer

      Article first published online: 3 FEB 2012 | DOI: 10.1002/anie.201108511

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      Teaming up: The important indoline scaffold is provided with enantiomeric ratios of up to 98:2 in palladium(0)-catalyzed C(sp3)–H activations of aryl triflates. The key is the combination of the electron-rich monodentate Sagephos and the bulky 9H-xanthene-9-carboxylic acid. Both participate in a highly cooperative manner in the enantiodetermining concerted-deprotonation-metalation step (see scheme, Tf=triflate).

    41. Artificial Proteins

      Multiple-Site Labeling of Proteins with Unnatural Amino Acids (pages 2243–2246)

      Dr. Karin V. Loscha, Anthony J. Herlt, Dr. Ruhu Qi, Dr. Thomas Huber, Dr. Kiyoshi Ozawa and Prof. Gottfried Otting

      Article first published online: 1 FEB 2012 | DOI: 10.1002/anie.201108275

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      A cell-free protein synthesis system from which the release factor RF1 has been selectively removed enables the facile incorporation of unnatural amino acids into proteins at difficult and multiple sites by optimized use of orthogonal tRNA/aminoacyl-tRNA synthetase systems. 19F NMR spectroscopy of a protein labeled combinatorially with trifluoromethyl phenylalanine (red in picture) at multiple sites establishes resonance assignments with a minimal number of samples.

    42. Double C[BOND]H Activation

      [RhIIICp*]-Catalyzed Dehydrogenative Aryl[BOND]Aryl Bond Formation (pages 2247–2251)

      Dr. Joanna Wencel-Delord, Corinna Nimphius, Prof. Dr. Frederic W. Patureau and Prof. Dr. Frank Glorius

      Article first published online: 27 JAN 2012 | DOI: 10.1002/anie.201107842

      Thumbnail image of graphical abstract

      Directed, undirected! Rhodium(III)-catalyzed double CH bond activation (one directed, one undirected) provides an efficient route to biaryls (see scheme; DG=directing group). Significant kinetic isotope effects for both reaction partners and H/D scrambling between them are interesting experimental findings. While the mechanism is still unclear, a rhodium(V) species is invoked in the catalytic cycle.

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