Angewandte Chemie International Edition

Cover image for Angewandte Chemie International Edition

March 12, 2012

Volume 51, Issue 11

Pages 2513–2782

  1. Cover Picture

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    6. Editorial
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    8. Corrigenda
    9. News
    10. Author Profile
    11. News
    12. Book Reviews
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
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    1. Cover Picture: Hydrogenolysis Goes Bio: From Carbohydrates and Sugar Alcohols to Platform Chemicals (Angew. Chem. Int. Ed. 11/2012) (page 2513)

      Dr. Agnieszka M. Ruppert, Dr. Kamil Weinberg and Prof. Dr. Regina Palkovits

      Version of Record online: 13 FEB 2012 | DOI: 10.1002/anie.201200420

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      The hydrogenolysis of renewable feedstocks has the potential to become a bridging technology between the petrochemical industry and future biorefinery concepts. In their Review on page 2564 ff., R. Palkovits et al. highlight developments in this field, with a focus on catalysts for the transformation of mono- and polysaccharides. Various concepts applied in the utilization of glycerol and sugars provide valuable information for the efficient transformation of biopolymers.

  2. Inside Cover

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    1. Inside Cover: Stacked Platinum Complexes of the Magnus’ Salt Type Inside a Coordination Cage (Angew. Chem. Int. Ed. 11/2012) (page 2514)

      Prof. Dr. Guido H. Clever, Wataru Kawamura, Dr. Shohei Tashiro, Dr. Motoo Shiro and Prof. Dr. Mitsuhiko Shionoya

      Version of Record online: 16 JAN 2012 | DOI: 10.1002/anie.201108968

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      Supramolecular coordination polymers based on stacked square-planar PtII complexes, such as Magnus' Salts, show potential as functional materials. In their Communication on page 2606 ff. G. H. Clever, M. Shionoya, and co-workers describe a linear array of five alternately stacked PtII complexes in the form of a soluble host–guest complex. The X-ray structure of {[Pt(pyridine)4]⋅[PtCl4]2@cage} shows the linear, pentanuclear array within the cages and their circular packing into a hollow tubular superstructure.

  3. Inside Back Cover

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    1. Inside Back Cover: Monitoring of Liquid-Phase Organic Reactions by Photoelectron Spectroscopy (Angew. Chem. Int. Ed. 11/2012) (page 2783)

      Claudia Kolbeck, Inga Niedermaier, Dr. Nicola Taccardi, Dr. Peter S. Schulz, Dr. Florian Maier, Prof. Peter Wasserscheid and Prof. Hans-Peter Steinrück

      Version of Record online: 30 DEC 2011 | DOI: 10.1002/anie.201108841

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      Nucleophilic substitution belongs to the fundamental organic reaction mechanisms since the pioneering work of C. K. Ingold in the 1920s. In their Communication on page 2610 ff., H.-P. Steinrück and co-workers monitor the alkylation of a tertiary amine attached to an imidazolium cation with a chloroalkylsulfonate anion by photoelectron spectroscopy, which can distinguish between convalently bound chlorine (Clcov) and chloride (Clion).

  4. Back Cover

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    14. Minireview
    15. Review
    16. Communications
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    1. Back Cover: Molecular Wheels of Ruthenium and Osmium with Bridging Chalcogenolate Ligands: Edge-Shared-Octahedron Structures and Metal-Ion Binding (Angew. Chem. Int. Ed. 11/2012) (page 2784)

      Dr. Sharon Lai-Fung Chan, Dr. Lam Shek, Dr. Jie-Sheng Huang, Dr. Stephen Sin-Yin Chui, Dr. Raymond Wai-Yin Sun and Prof. Dr. Chi-Ming Che

      Version of Record online: 8 DEC 2011 | DOI: 10.1002/anie.201108160

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      Wheel-like assemblies are fascinating and exquisite. Anderson-type molecular wheels (structures on the periphery first proposed in 1937 and right structure) each feature six skew-edge-shared octahedra. In their Communication on page 2614 ff., C. M. Che and co-workers report selective binding of Cu+ or Ag+ by isolated [{M(S-4-R-C6H4)2(CO)2}6] (right structure to bottom-right structure) and isolation of [{M(SPh)2(CO)2}8] (bottom left), thus demonstrating feasible expansion of Anderson-type wheels to octanuclear congeners.

  5. Editorial

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      Editorial: The Nonsense of Biofuels (pages 2516–2518)

      Prof. Dr. Hartmut Michel

      Version of Record online: 20 FEB 2012 | DOI: 10.1002/anie.201200218

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  6. Graphical Abstract

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  7. Corrigenda

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      Corrigendum: A Highly Active Catalyst for the Hydrogenation of Amides to Alcohols and Amines (page 2533)

      Jeremy M. John and Prof. Dr. Steven H. Bergens

      Version of Record online: 7 MAR 2012 | DOI: 10.1002/anie.201108479

      This article corrects:

      A Highly Active Catalyst for the Hydrogenation of Amides to Alcohols and Amines1

      Vol. 50, Issue 44, 10377–10380, Version of Record online: 26 AUG 2011

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      Corrigendum: Towards Understanding the Catalytic Reforming of Biomass in Supercritical Water (page 2533)

      Stefan Rabe, Maarten Nachtegaal, Thomas Ulrich and Frédéric Vogel

      Version of Record online: 7 MAR 2012 | DOI: 10.1002/anie.201109093

      This article corrects:

      Towards Understanding the Catalytic Reforming of Biomass in Supercritical Water1

      Vol. 49, Issue 36, 6434–6437, Version of Record online: 26 JUL 2010

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      Corrigendum: Experimental Evidence of Phosphine Oxide Generation in Solution and Trapping by Ruthenium Complexes (page 2533)

      Dr. Dmitry Yakhvarov, Dr. Maria Caporali, Dr. Luca Gonsalvi, Dr. Shamil Latypov, Vincenzo Mirabello, Dr. Ildar Rizvanov, Prof. Oleg Sinyashin, Prof. Piero Stoppioni and Dr. Maurizio Peruzzini

      Version of Record online: 7 MAR 2012 | DOI: 10.1002/anie.201200574

      This article corrects:

      Experimental Evidence of Phosphine Oxide Generation in Solution and Trapping by Ruthenium Complexes1

      Vol. 50, Issue 23, 5370–5373, Version of Record online: 28 APR 2011

  8. News

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  9. Author Profile

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    1. Michael M. Haley (page 2540)

      Version of Record online: 20 FEB 2012 | DOI: 10.1002/anie.201108374

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      “A good work day begins with an early morning workout at the gym. My favorite song is “Supper's Ready” by Genesis. …” This and more about Michael M. Haley can be found on page 2540.

  10. News

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  11. Book Reviews

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    1. The Biofuels Handbook. RSC Energy Series, Vol. 5. Edited by James G. Speight. (pages 2542–2543)

      Mark Rüsch gen. Klaas

      Version of Record online: 20 JAN 2012 | DOI: 10.1002/anie.201108812

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      Royal Society of Chemistry, Cambridge, 2011. 574 pp., hardcover, £ 280.00.—ISBN 978-1849730266

    2. Hyperbranched Polymers. Synthesis, Properties, and Applications. Edited by Deyue Yan, Chao Gao and Holger Frey. (page 2543)

      Lian Hutchings

      Version of Record online: 20 FEB 2012 | DOI: 10.1002/anie.201108985

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      John Wiley & Sons, Hoboken, 2011. 480 pp., hardcover, € 129.00.—ISBN 978-0471780144

  12. Highlights

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    1. Trefoil Knot

      Combining Coordination Chemistry and Catalysis To Tie a Knot by an Active-Metal Template Strategy (pages 2544–2545)

      Dr. Camille Romuald and Dr. Frédéric Coutrot

      Version of Record online: 11 JAN 2012 | DOI: 10.1002/anie.201107112

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      Collar and tie men: The smallest trefoil knot reported to date has been prepared by an active metal template synthesis. Copper(I) ions are able to constrain the well-designed structure so that it can form the loops by complexing to the bipyridine moieties in the core of the thread and the two ends of the entangled lace on opposite faces of the loop, before acting as a catalyst to close the lace (see picture).

    2. Surface Patterning

      Re-Shaping the Coffee Ring (pages 2546–2548)

      Prof. Ronald G. Larson

      Version of Record online: 25 JAN 2012 | DOI: 10.1002/anie.201108008

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      Not your cup of tea? “Coffee rings” of spherical colloidal particles are left behind after water droplets resting on surfaces have dried out. This controlled evaporation of colloidal solutions can be exploited to deposit material in regular patterns (see picture). It is now shown that if spherical colloids are replaced by slightly elongated ones, the coffee ring is not formed and is replaced by an even more uniform deposition.

  13. Minireview

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    1. Stereochemistry

      The Diaryl(oxy)methyl Group: More than an Innocent Bystander in Chiral Auxiliaries, Catalysts, and Dopants (pages 2550–2562)

      Prof. Dr. Manfred Braun

      Version of Record online: 1 MAR 2012 | DOI: 10.1002/anie.201105127

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      Not chiral, but temporarily stereogenic: The introduction of a diaryl(oxy)methyl group into chiral auxiliaries, catalysts, and dopants can be rewarding: As a temporary stereogenic unit, it has a beneficial effect in a variety of asymmetric syntheses and has helped a series of well-known, efficient, and reliable “work horses” to succeed.

  14. Review

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    1. Renewable Feedstocks

      Hydrogenolysis Goes Bio: From Carbohydrates and Sugar Alcohols to Platform Chemicals (pages 2564–2601)

      Dr. Agnieszka M. Ruppert, Dr. Kamil Weinberg and Prof. Dr. Regina Palkovits

      Version of Record online: 28 FEB 2012 | DOI: 10.1002/anie.201105125

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      Hydrogenolysis of renewable feedstocks allows direct access to valuable platform chemicals already integrated in today's value chains. Transformations based on hydrogenolysis bear the potential to bridge available technologies and future biorefinery concepts. This Review highlights developments in this field, with special emphasis on the direct transformation of cellulose and sugars.

  15. Communications

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    1. Smart Materials

      Reversibly Switching the Function of a Surface between Attacking and Defending against Bacteria (pages 2602–2605)

      Zhiqiang Cao, Luo Mi, Jose Mendiola, Jean-Rene Ella-Menye, Lei Zhang, Hong Xue and Prof. Shaoyi Jiang

      Version of Record online: 30 DEC 2011 | DOI: 10.1002/anie.201106466

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      Attack or defend! A smart polymer surface has two reversibly switchable equilibrium states, a cationic N,N-dimethyl-2-morpholinone (CB-Ring) and a zwitterionic carboxy betaine (CB-OH). CB-Ring will kill bacteria upon contact under dry conditions, whereas CB-OH will release the previously attached and dead bacteria and further resist adhesion of bacteria under wet conditions.

    2. Metal Stacking

      Stacked Platinum Complexes of the Magnus’ Salt Type Inside a Coordination Cage (pages 2606–2609)

      Prof. Dr. Guido H. Clever, Wataru Kawamura, Dr. Shohei Tashiro, Dr. Motoo Shiro and Prof. Dr. Mitsuhiko Shionoya

      Version of Record online: 11 JAN 2012 | DOI: 10.1002/anie.201108197

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      Neatly wrapped up: Alternately stacked square-planar platinum(II) complexes inside a dinuclear coordination cage were prepared to give a discrete and soluble Pt5-array of the Magnus' salt type. Characterization of the complex in solution was complemented by an X-ray crystal structure of {[Pt(pyridine)4] [PtCl4]2@Cage}; this structure showed the linear, pentanuclear array within the cages and their circular packing into a hollow tubular superstructure.

    3. Ionic Liquids

      Monitoring of Liquid-Phase Organic Reactions by Photoelectron Spectroscopy (pages 2610–2613)

      Claudia Kolbeck, Inga Niedermaier, Dr. Nicola Taccardi, Dr. Peter S. Schulz, Dr. Florian Maier, Prof. Peter Wasserscheid and Prof. Hans-Peter Steinrück

      Version of Record online: 23 DEC 2011 | DOI: 10.1002/anie.201107402

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      There are strings attached: After linking the reacting groups to head groups of ionic liquids to drastically lower the vapour pressures of the reactants, ordinary liquid-phase organic reactions can be monitored by in situ X-ray photoelectron spectroscopy. This approach is demonstrated for the nucleophilic substitution of an alkyl amine and an alkyl chloride moiety, which are attached to the cation and anion of ionic liquids, respectively.

    4. Multinuclear Structures

      Molecular Wheels of Ruthenium and Osmium with Bridging Chalcogenolate Ligands: Edge-Shared-Octahedron Structures and Metal-Ion Binding (pages 2614–2617)

      Dr. Sharon Lai-Fung Chan, Dr. Lam Shek, Dr. Jie-Sheng Huang, Dr. Stephen Sin-Yin Chui, Dr. Raymond Wai-Yin Sun and Prof. Dr. Chi-Ming Che

      Version of Record online: 7 NOV 2011 | DOI: 10.1002/anie.201106065

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      Inventing new wheels: Reaction of [M3(CO)12] (M=Ru, Os) with 4-RC6H4SH afforded [{M(S-4-RC6H4)2(CO)2}8] (R=H; I) or [{M(S-4-RC6H4)2(CO)2}6] (R=Me, iPr; II; see scheme), all of which have been structurally characterized. The octamers I are unique metal molecular wheels featuring skew-edge-shared octahedra with a central planar M8 octagon. [{Ru(S-4-iPrC6H4)2(CO)2}6] selectively binds a Cu+ or Ag+ ion to form [M′{Ru(S(4-iPr-C6H4))2(CO)2}6]+ (III).

    5. Conducting Materials

      High-Rate Charge-Carrier Transport in Porphyrin Covalent Organic Frameworks: Switching from Hole to Electron to Ambipolar Conduction (pages 2618–2622)

      Xiao Feng, Lili Liu, Yoshihito Honsho, Akinori Saeki, Prof. Dr. Shu Seki, Prof. Dr. Stephan Irle, Prof. Yuping Dong, Dr. Atsushi Nagai and Prof. Dr. Donglin Jiang

      Version of Record online: 31 JAN 2012 | DOI: 10.1002/anie.201106203

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      Well conducted: A two-dimensional porphyrin covalent organic framework is described. Owing to the eclipsed stacking alignment, the framework is conductive and allows high-rate carrier transport through the porphyrin columns (see picture). The central metal in the porphyrin rings changes the conducting nature of the material from hole to electron, and to ambipolar conduction. It also drives the high on–off ratio photoconductivity of the framework.

    6. Covalent Organic Frameworks

      Lattice Expansion of Highly Oriented 2D Phthalocyanine Covalent Organic Framework Films (pages 2623–2627)

      Dr. Eric L. Spitler, John W. Colson, Dr. Fernando J. Uribe-Romo, Dr. Arthur R. Woll, Marissa R. Giovino, Abraham Saldivar and Prof. Dr. William R. Dichtel

      Version of Record online: 3 JAN 2012 | DOI: 10.1002/anie.201107070

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      Expanding into application: Covalent organic framework (COF) films are ideally suited for vertical charge transport and serve as precursors of ordered heterojunctions. Their pores, however, were previously too small to accommodate continuous networks of complementary electron acceptors. Four phthalocyanine COFs with increased pore size well into the mesoporous regime are now described (see picture).

    7. Protein Assemblies

      Photocurrent Generation from Hierarchical Zinc-Substituted Hemoprotein Assemblies Immobilized on a Gold Electrode (pages 2628–2631)

      Dr. Akira Onoda, Yasuaki Kakikura, Dr. Taro Uematsu, Prof. Dr. Susumu Kuwabata and Prof. Dr. Takashi Hayashi

      Version of Record online: 6 OCT 2011 | DOI: 10.1002/anie.201105186

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      All connected: A protein-immobilized electrode comprising hierarchical assemblies of photoactive cytochrome b562 reconstituted with zinc protoporphyrin IX exhibits remarkably enhanced photocurrent generation relative to an electrode bearing a single zinc-substituted hemoprotein layer. The protein oligomers, which bear a covalently linked protoporphyrin group, assemble by a supramolecular heme/heme pocket interaction.

    8. Nanoscale Chemistry

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      Hyperstoichiometric Interaction Between Silver and Mercury at the Nanoscale (pages 2632–2635)

      Dr. Kseniia V. Katok, Dr. Raymond L. D. Whitby, Dr. Takahiro Fukuda, Prof. Toru Maekawa, Dr. Igor Bezverkhyy, Prof. Sergey V. Mikhalovsky and Prof. Andrew B. Cundy

      Version of Record online: 3 FEB 2012 | DOI: 10.1002/anie.201106776

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      Breaking through the stoichiometry barrier: As the diameter of silver particles is decreased below a critical size of 32 nm, the molar ratio of aqueous HgII to Ag0 drastically increases beyond the conventional Hg/Ag ratio of 0.5:1, leading to hyperstoichiometry with a maximum ratio of 1.125:1 (see figure). Therein, around 99 % of the initial silver is retained to rapidly form a solid amalgam with reduced mercury.

    9. Cross-Coupling

      Palladium-Catalyzed Dehydrative Heck Olefination of Secondary Aryl Alcohols in Ionic Liquids: Towards a Waste-Free Strategy for Tandem Synthesis of Stilbenoids (pages 2636–2639)

      Rakesh Kumar, Amit Shard, Richa Bharti, Yogesh Thopate and Arun Kumar Sinha

      Version of Record online: 1 FEB 2012 | DOI: 10.1002/anie.201107261

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      All in one: A tandem strategy has been developed wherein secondary aryl alcohols are directly coupled with aryl halides to provide stilbenoids through a dehydrative Heck sequence in the ionic liquid [hmim]Br, and with water as a by-product under microwave irradiation (see scheme). Classical methods do not permit this sequence to proceed in one pot, and some methods require multiple steps. hmim=1-n-hexyl-3-methylimidazolium.

    10. Surface Chemistry

      Electric-Field Enhancement Inducing Near-Infrared Two-Photon Absorption in an Indium–Tin Oxide Nanoparticle Film (pages 2640–2642)

      Dr. Akihiro Furube, Taizo Yoshinaga, Dr. Masayuki Kanehara, Dr. Miharu Eguchi and Prof. Toshiharu Teranishi

      Version of Record online: 1 FEB 2012 | DOI: 10.1002/anie.201107450

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      An enhancing factor: The enhancement of the electric properties of a dye molecule (IR26) by indium–tin oxide nanoparticles (ITO NPs, see picture) has been shown by measuring the near-infrared two-photon-excited transient absorption spectra. The dye molecule was excited much more efficiently in the presence of an ITO NP layer.

    11. Enzyme Catalysis

      Tetrahydroxynaphthalene Reductase: Catalytic Properties of an Enzyme Involved in Reductive Asymmetric Naphthol Dearomatization (pages 2643–2646)

      Michael A. Schätzle, Stephan Flemming, Dr. Syed Masood Husain, Dr. Michael Richter, Dr. Stefan Günther and Prof. Dr. Michael Müller

      Version of Record online: 3 FEB 2012 | DOI: 10.1002/anie.201107695

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      In reduced circumstances: Tetrahydroxynaphthalene reductase shows a broad substrate range including alternate phenolic compounds and cyclic ketones. Structural modeling reveals major enzyme–substrate interactions; C-terminal truncation of the enzyme causes an altered substrate preference, in accordance with stabilization of the substrate by the C-terminal carboxylate (see picture). This effect allows the identification of a homologous enzyme.

    12. Solid-State Structures

      Na2.8Cu5Sn5.6: A Crystalline Alloy Featuring Intermetalloid equation image Double-Walled Nanorods with Pseudo-Five-Fold Symmetry (pages 2647–2650)

      Dipl.-Chem. Saskia Stegmaier and Prof. Dr. Thomas F. Fässler

      Version of Record online: 1 FEB 2012 | DOI: 10.1002/anie.201107985

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      Not quasi-crystalline: Approximate five-fold symmetry appears in bronze-type Cu–Sn rods that are separated by Na atoms in Na2.8Cu5Sn5.6 (see picture). The rods are compared to the [Sn@Cu12@Sn20]12− cluster in the recently characterized A12Cu12Sn21 phases (A=Na–Cs), and a saltlike description in analogy to Zintl phases of p-block metals is introduced for these new polar intermetallic phases with a high d-block metal content.

    13. Energy Transfer

      Dynamic Mapping of CN Rotation Following Photoexcitation of ICN (pages 2651–2653)

      Dr. Amanda S. Case, Elisa M. Miller, Joshua P. Martin, Yu-Ju Lu, Dr. Leonid Sheps, Prof. Anne B. McCoy and Prof. W. Carl Lineberger

      Version of Record online: 1 FEB 2012 | DOI: 10.1002/anie.201108025

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      In a spin: The dynamics of photoexcited ICN(Ar)0–5 are presented. Photodetachment produces quasi-thermal electron emission that leaves ICN with up to 2.85 eV of internal energy. Photodissociation at 2.5 eV leads to one-atom caging and highly solvated anion products. Calculations indicate efficient energy transfer into CN rotation upon excitation to the 2Π1/2 excited state. CN rotation is vital to explain the unique dynamics observed.

    14. Organogold(III) Photochemistry

      Luminescent Organogold(III) Complexes with Long-Lived Triplet Excited States for Light-Induced Oxidative C[BOND]H Bond Functionalization and Hydrogen Production (pages 2654–2657)

      Wai-Pong To, Dr. Glenna So-Ming Tong, Dr. Wei Lu, Chensheng Ma, Dr. Jia Liu, Dr. Andy Lok-Fung Chow and Prof. Dr. Chi-Ming Che

      Version of Record online: 3 FEB 2012 | DOI: 10.1002/anie.201108080

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      All that glitters is gold: Highly phosphorescent gold(III) complexes (see picture) with extended π-conjugated cyclometalating ligands exhibit rich photophysical and photochemical properties. They act as efficient photocatalysts/photosensitizers for oxidative functionalizations of secondary and tertiary benzylic amines and homogeneous hydrogen production from a water/acetonitrile mixture.

    15. Bioinorganic Chemistry

      Photodynamic Effect in Near-IR Light by a Photocytotoxic Iron(III) Cellular Imaging Agent (pages 2658–2661)

      Uttara Basu, Imran Khan, Akhtar Hussain, Prof. Paturu Kondaiah and Prof. Akhil R. Chakravarty

      Version of Record online: 30 JAN 2012 | DOI: 10.1002/anie.201108360

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      A red light for cancer cells: An iron(III) complex (1, see picture) that contains an anthracenyl fluorophore moiety and a catecholate ligand is a potent, metal-based PDT agent that efficiently photocleaves DNA in near-infrared light, has significant nuclear uptake, and high photocytotoxicity in red light by an apoptotic pathway in HeLa and MCF-7 cancer cells.

    16. Metal–Organic Frameworks

      Transport into Metal–Organic Frameworks from Solution Is Not Purely Diffusive (pages 2662–2666)

      Dr. Shuangbing Han, Dr. Ir. Thomas M. Hermans, Patrick E. Fuller, Dr. Yanhu Wei and Prof. Dr. Bartosz A. Grzybowski

      Version of Record online: 1 FEB 2012 | DOI: 10.1002/anie.201108492

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      Chemistry in motion: A combination of confocal microscopy (see picture) and reaction-diffusion modeling provided a powerful toolkit with which solution transport into metal–organic framework crystals was studied. Commonly used pure diffusion models are insufficient to describe this process and, instead, it is necessary to account for the interactions of the guest molecules and the MOF scaffold.

    17. Cross-Coupling

      You have full text access to this OnlineOpen article
      A General Solution for the 2-Pyridyl Problem (pages 2667–2672)

      Graham R. Dick, Eric M. Woerly and Prof. Martin D. Burke

      Version of Record online: 27 JAN 2012 | DOI: 10.1002/anie.201108608

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      Problem solved: An air-stable 2-pyridyl borane that can effectively couple to a wide range of aryl and heteroaryl halides and pseudohalides has evaded the synthesis community for decades. The discovery that Cu(DEA)2 powerfully enables palladium-mediated cross-couplings with air-stable boronates 1 has finally provided a general solution to this problem. DEA=diethanolamine, DMF=N,N′-dimethylformamide, Tf=trifluoromethanesulfonyl.

    18. Fluorescent Probes

      Measurement of pH Values in Human Tissues by Two-Photon Microscopy (pages 2673–2676)

      Dr. Hee Jung Park, Chang Su Lim, Prof. Dr. Eun Sun Kim, Ji Hee Han, Tae Hee Lee, Prof. Dr. Hoon Jai Chun and Prof. Dr. Bong Rae Cho

      Version of Record online: 1 FEB 2012 | DOI: 10.1002/anie.201109052

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      pH values go live! A ratiometric two-photon (TP) probe (NP1, see scheme) that has a significant TP action cross-section, high photostability, negligible toxicity, and can estimate pH values in live cells and human tissues by two-photon microscopy is described. NP1 can detect the difference in pH between live cells from the gastroesophageal junction (GEJ) and the lower esophageal sphincter of patients with and without esophagitis (see image).

    19. Carborane Clusters

      Carborane Photochemistry Triggered by Aryl Substitution: Carborane-Based Dyads with Phenyl Carbazoles (pages 2677–2680)

      Kyung-Ryang Wee, Won-Sik Han, Dae Won Cho, Soonnam Kwon, Chyongjin Pac and Sang Ook Kang

      Version of Record online: 1 FEB 2012 | DOI: 10.1002/anie.201109069

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      A bright combination: A new type of donor–acceptor dyad, carbazolylaryl-substituted ortho-carboranes, which are conveniently prepared from the corresponding acetylenes and decaborane pathways, showed unique excited-state behavior associated with electron transfer unlike the meta- and para-counterparts (see picture).

    20. Organocuprates

      Minimization of Organocuprate Complexity through Self-Organization: Remarkable Orientation Effect in Mixed Cuprate π Complexes (pages 2681–2685)

      Prof. Dr. Steven H. Bertz, Richard A. Hardin, Dr. Michael D. Murphy, Prof. Dr. Craig A. Ogle, Joshua D. Richter and Andy A. Thomas

      Version of Record online: 1 FEB 2012 | DOI: 10.1002/anie.201107060

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      They “know” where to go: A powerful orientation effect has been observed in complexes of mixed organocuprates [RTRNTCuLi] and substrates with C[BOND]C, C[BOND]N, and C[BOND]S double bonds (see scheme; Th=thienyl). The preferred geometry of the intermediate complex sets up the facile addition of RT to the double bond, rather than addition of the “dummy ligand”, RNT.

    21. Bioelectronic Devices

      A Self-Powered “Sense-Act-Treat” System that is Based on a Biofuel Cell and Controlled by Boolean Logic (pages 2686–2689)

      Dr. Ming Zhou, Dr. Nandi Zhou, Dr. Filiz Kuralay, Joshua R. Windmiller, Serguey Parkhomovsky, Dr. Gabriela Valdés-Ramírez, Prof. Evgeny Katz and Prof. Joseph Wang

      Version of Record online: 3 JAN 2012 | DOI: 10.1002/anie.201107068

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      Bio-logic-al: An autonomous, integrated “sense-act-treat” system that is based on an enzymatic biofuel cell has been developed. The system couples a biocomputing logic-detection method with a drug-release system to provide a logic-activated therapeutic intervention in response to a simulated abnormal physiological state, without the need for an external power source, control electronics, or microelectromechanical actuators.

    22. Biaryls

      Extrusion of CO from Aryl Ketones: Rhodium(I)-Catalyzed C[BOND]C Bond Cleavage Directed by a Pyridine Group (pages 2690–2694)

      Zhi-Quan Lei, Hu Li, Dr. Yang Li, Xi-Sha Zhang, Kang Chen, Xin Wang, Prof. Dr. Jian Sun and Prof. Dr. Zhang-Jie Shi

      Version of Record online: 6 FEB 2012 | DOI: 10.1002/anie.201107136

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      Snipping tool: The rhodium(I)-catalyzed extrusion of carbon monoxide from biaryl ketones and alkyl/alkenyl aryl ketones was developed to produce biaryls and alkyl/alkenyl arenes, respectively, in high yields (see scheme). A wide range of functionalities are tolerated. Not only does this method provide an alternative pathway to construct useful scaffolds, but also offers a new strategy for C[BOND]C bond activation.

    23. Contact Electrification

      Strain-Induced Reversal of Charge Transfer in Contact Electrification (pages 2695–2697)

      Dr. Mamadou Sow, Ross Widenor, Dr. Ajay Kumar, Seung Whan Lee, Prof. Daniel J. Lacks and Prof. R. Mohan Sankaran

      Version of Record online: 27 JAN 2012 | DOI: 10.1002/anie.201107256

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      We have contact! Material strain can have a dominating effect on contact electrification. When a deflated (relaxed) balloon is rubbed against teflon, the teflon surface charges positively, but when the same balloon is inflated (strained), the teflon surface charges negatively. This result illustrates that material strain can control contact electrification and alter the driving force of some (yet unknown) charge-transfer species.

    24. Radiochemistry

      CuI-Catalyzed 11C Carboxylation of Boronic Acid Esters: A Rapid and Convenient Entry to 11C-Labeled Carboxylic Acids, Esters, and Amides (pages 2698–2702)

      Dr. Patrick J. Riss, Dr. Shuiyu Lu, Dr. Sanjay Telu, Dr. Franklin I. Aigbirhio and Dr. Victor W. Pike

      Version of Record online: 3 FEB 2012 | DOI: 10.1002/anie.201107263

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      Rapid and direct: The carboxylation of boronic acid esters with 11CO2 provides [11C]carboxylic acids as a convenient entry into [11C]esters and [11C]amides (see scheme). This conversion of boronates is tolerant to diverse functional groups (e.g., halo, nitro, or carbonyl).

    25. Carbocyclization

      Palladium-Catalyzed Oxidative Arylating Carbocyclization of Allenynes (pages 2703–2707)

      Dr. Youqian Deng, Teresa Bartholomeyzik, Andreas K. Å. Persson, Prof. Dr. Junliang Sun and Prof. Dr. Jan-E. Bäckvall

      Version of Record online: 27 JAN 2012 | DOI: 10.1002/anie.201107592

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      Vinylallenes or cross-conjugated trienes are obtained selectively in the title reaction (see scheme). Two possible mechanisms are suggested to rationalize the formation of the different types of products. Control experiments indicate that p-benzoquinone (BQ) plays an important role as a ligand in addition to its role as an oxidant. E=CO2Me.

    26. Iridium-Catalyzed Hydrogenation

      Enantioselective Iridium-Catalyzed Hydrogenation of β,γ-Unsaturated Carboxylic Acids: An Efficient Approach to Chiral 4-Alkyl-4-aryl Butanoic Acids (pages 2708–2711)

      Song Song, Prof. Shou-Fei Zhu, Shuang Yang, Shen Li and Prof. Qi-Lin Zhou

      Version of Record online: 3 FEB 2012 | DOI: 10.1002/anie.201107802

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      Chiral acids: A highly enantioselective iridium-catalyzed hydrogenation of β,γ-unsaturated carboxylic acids is developed for the preparation of chiral 4-alkyl-4-aryl butanoic acids (see scheme).

    27. Synthetic Methods

      Arylsulfonylacetylenes as Alkynylating Reagents of Cmath image[BOND]H Bonds Activated with Lithium Bases (pages 2712–2716)

      Prof. Dr. José Luis García Ruano, Dr. José Alemán, Leyre Marzo, Dr. Cuauhtémoc Alvarado, Dr. Mariola Tortosa, Dr. Sergio Díaz-Tendero and Dr. Alberto Fraile

      Version of Record online: 1 FEB 2012 | DOI: 10.1002/anie.201107821

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      Chameleon: A new strategy for the synthesis of a wide variety of alkynyl derivatives by the reaction of substituted arylsulfonylacetylenes with organolithium species is described (see scheme). The high yields, the simplicity of the experimental procedure, the broad scope of this reaction, and the formation of Csp[BOND]Cmath image bonds without using transition metals are the main features of this methodology.

    28. Homogeneous Catalysis

      Iterative Asymmetric Allylic Substitutions: syn- and anti-1,2-Diols through Catalyst Control (pages 2717–2721)

      Dr. Jin Kyoon Park and Prof. Dr.  D. Tyler McQuade

      Version of Record online: 1 FEB 2012 | DOI: 10.1002/anie.201107874

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      A copper-catalyzed asymmetric allylic boronation (AAB) gives access to syn- and anti-1,2-diols. The method facilitates an iterative strategy for the preparation of polyols (see scheme), such as the fully differentiated L-ribo-tetrol and protected D-arabino-tetrol. P=protecting group

    29. Synthetic Methods

      In Situ Anionic Shielding for Regioselective Metalation: Directed peri and Iterative Metalation Routes to Polyfunctionalized 7-Azaindoles (pages 2722–2726)

      Dr. Cédric Schneider, Dr. Emilie David, Anton A. Toutov and Prof. Victor Snieckus

      Version of Record online: 1 FEB 2012 | DOI: 10.1002/anie.201108016

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      Strolling the ring: A general regioselective directed peri(C4)-metalation route to 1 through an in situ N-anionic protection of C2 is reported. The azaindoles may be elaborated by directed ortho metalation (DoM) and Suzuki coupling to more complex heterocyclic systems. An iterative ring-walk DoM sequence furnishes the exhaustively substituted 2. DMG=directed metalation group, TMEDA=N,N,N′,N′-tetramethylethylenediamine, TMS=trimethylsilyl.

    30. Solar Cells

      Rapid Charge Transport in Dye-Sensitized Solar Cells Made from Vertically Aligned Single-Crystal Rutile TiO2 Nanowires (pages 2727–2730)

      Dr. Xinjian Feng, Dr. Kai Zhu, Dr. Arthur J. Frank, Prof. Craig A. Grimes and Prof. Thomas E. Mallouk

      Version of Record online: 2 FEB 2012 | DOI: 10.1002/anie.201108076

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      A rapid solvothermal approach was used to synthesize aligned 1D single-crystal rutile TiO2 nanowire (NW) arrays on transparent conducting substrates as electrodes for dye-sensitized solar cells. The NW arrays showed a more than 200 times faster charge transport (see picture) and a factor four lower defect state density than conventional rutile nanoparticle films.

    31. Solid-State NMR Spectroscopy

      Dual Acquisition Magic-Angle Spinning Solid-State NMR-Spectroscopy: Simultaneous Acquisition of Multidimensional Spectra of Biomacromolecules (pages 2731–2735)

      Dr. T. Gopinath and Prof. Gianluigi Veglia

      Version of Record online: 6 FEB 2012 | DOI: 10.1002/anie.201108132

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      Fast data collection: A general method for dual data acquisition of multidimensional magic-angle spinning solid-state NMR experiments is presented (see picture). The method uses a simultaneous Hartmann–Hahn cross-polarization from 1H to 13C and 15N nuclei and exploits the long-living 15N polarization for parallel acquisition of two multidimensional experiments.

    32. Synthetic Methods

      Rhodium Dinaphthocyclooctatetraene Complexes: Synthesis, Characterization and Catalytic Activity in [5+2] Cycloadditions (pages 2736–2740)

      Prof. Paul A. Wender, Adam B. Lesser and Lauren E. Sirois

      Version of Record online: 1 FEB 2012 | DOI: 10.1002/anie.201108270

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      Rh COT in the act: A Ni0-catalyzed [2+2+2+2] cycloaddition provides a high-yielding, scalable synthesis of the ligand dinaphtho[a,e]cyclooctatetraene (dnCOT). dnCOT complexation with RhI gives [Rh(dnCOT)(MeCN)2]SbF6 (see scheme), an excellent catalyst for [5+2] cycloadditions of vinylcyclopropanes and π-systems with impressive functional group compatibility.

    33. Photochemistry

      Reporting the Release of Caged Species by a Combination of Two Sequential Photoreactions, a Molecular Switch, and One Color of Light (pages 2741–2744)

      Tuoqi Wu, Hao Tang, Prof. Cornelia Bohne and Prof. Neil R. Branda

      Version of Record online: 27 JAN 2012 | DOI: 10.1002/anie.201108336

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      In the right light: UV light triggers bond breaking, liberates a caged carboxylic acid, and generates the central C[DOUBLE BOND]C double bond in the photoresponsive hexatriene molecule of a dithienylethene molecular switch. Light of the same wavelength converts the colorless isomer into its colored counterpart (see picture) in a visually convenient method to report on the success of the release event.

    34. Synthetic Methods

      Synthesis of Aryl(di)azinyl Ketones through Copper- and Iron-catalyzed Oxidation of the Methylene Group of Aryl(di)azinylmethanes (pages 2745–2748)

      Johan De Houwer, Prof. Dr. Kourosch Abbaspour Tehrani and Prof. Dr. Bert U. W. Maes

      Version of Record online: 30 JAN 2012 | DOI: 10.1002/anie.201108540

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      Sustainable Oxidations: An oxidation method to transform aryl(di)azinylmethanes into aryl(di)azinyl ketones is described. Base metals (copper and iron) as catalysts in combination with O2 as the oxidant are used, which makes this method sustainable. The utility of this method is illustrated by the synthesis of 6-(4-methylbenzoyl)pyridine-2-carbaldehyde, which is an intermediate in the preparation of the drug Acrivastine.

    35. Natural Product Synthesis

      A Second-Generation Total Synthesis of Spirastrellolide A Methyl Ester (pages 2749–2753)

      Prof. Ian Paterson, Dr. Philip Maltas, Dr. Stephen M. Dalby, Dr. Jong Ho Lim and Dr. Edward A. Anderson

      Version of Record online: 6 FEB 2012 | DOI: 10.1002/anie.201108594

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      Marine macrolides: An improved second-generation total synthesis of the anticancer macrolide spirastrellolide A methyl ester has been achieved. The synthesis features a uniformly high level of stereocontrol combined with more expedient fragment assembly, and demonstrates a critical dependence of the crucial macrolactonization step on the substitution pattern of the C22–C24 linker region.

    36. Organometallic Chemistry

      Solid-State and Solution Structure of a Hypervalent AX5 Compound: Sb(C6F5)5 (pages 2754–2757)

      Dr. M. Angeles García-Monforte, Prof. Dr. Pablo J. Alonso, Dr. Irene Ara, Dr. Babil Menjón and Dr. Pilar Romero

      Version of Record online: 3 FEB 2012 | DOI: 10.1002/anie.201108858

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      Eliminating restraints: A trigonal-bipyramidal structure has been found to be the energetically favored geometry of the hypervalent AX5 molecule Sb(C6F5)5 in the solid state and also in fluid solution, where molecules move freely and no crystal packing effects operate (see picture).

    37. Heterocycles

      An Efficient Computational Model to Predict the Synthetic Utility of Heterocyclic Arynes (pages 2758–2762)

      Adam E. Goetz, Sarah M. Bronner, Jordan D. Cisneros, Joshua M. Melamed, Prof. Robert S. Paton, Prof. K. N. Houk and Prof. Neil K. Garg

      Version of Record online: 3 FEB 2012 | DOI: 10.1002/anie.201108863

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      Think before you act: A computational approach is reported for evaluating the synthetic potential of heterocyclic arynes. Routine and rapid calculations of arene dehydrogenation energies and aryne angle distortion predict the likelihood that a given hetaryne can be generated, as well as the degree of regioselectivity expected in a reaction between a given hetaryne and a nucleophilic trapping agent (see picture).

    38. Synthetic Methods

      Palladium-Catalyzed Amidation by Chemoselective C(sp3)[BOND]H Activation: Concise Route to Oxindoles Using a Carbamoyl Chloride Precursor (pages 2763–2766)

      Dr. Chihiro Tsukano, Masataka Okuno and Prof. Dr. Yoshiji Takemoto

      Version of Record online: 2 FEB 2012 | DOI: 10.1002/anie.201108889

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      Quite select: A new strategy was developed for the synthesis of various oxindoles from carbamoyl chlorides. Under the optimum reaction conditions, with Ad2PBu as a ligand, tBuCONHOH as an additive, and a CO atmosphere, selective C(sp3)[BOND]H activation proceeded in the presence of a C(sp2)[BOND]H bond. Ad=adamantyl.

    39. Nanoporous Materials

      Chemical-Assisted Thermal Disproportionation of Porous Silicon Monoxide into Silicon-Based Multicomponent Systems (pages 2767–2771)

      Jung-In Lee, Prof. Kyu Tae Lee, Prof. Jaephil Cho, Dr. Jeyoung Kim, Prof. Nam-Soon Choi and Prof. Soojin Park

      Version of Record online: 3 FEB 2012 | DOI: 10.1002/anie.201108915

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      Under the surface: Ag nanoparticles are deposited onto the surface of commercially available SiO particles, and subsequent chemical etching results in the formation of nanoporous SiO (see picture) without changing the chemical and physical properties of the original SiO. Moreover, chemical-assisted thermal annealing produces a shape-preserving Si-based multicomponent system, which exhibits high-performance electrochemical properties.

    40. Catalytic (De)Hydrogenation

      From Esters to Alcohols and Back with Ruthenium and Osmium Catalysts (pages 2772–2775)

      Dr. Denis Spasyuk, Samantha Smith and Prof. Dmitry G. Gusev

      Version of Record online: 8 FEB 2012 | DOI: 10.1002/anie.201108956

      Thumbnail image of graphical abstract

      There and back again: Hydrogenation of esters and the reverse reaction of dehydrogenative coupling of alcohols are efficiently catalyzed by dimeric complexes of Ru and Os under neutral conditions. The Os dimer (see picture) is an outstanding catalyst for the hydrogenation of alkenoates and triglycerides, and allows production of fatty alcohols from olive oil. This complex converts ethanol into ethyl acetate and hydrogen under reflux.

    41. Asymmetric Synthesis

      Highly Z-Selective Asymmetric Conjugate Addition of Alkynones with Pyrazol-5-ones Promoted by N,N′-Dioxide–Metal Complexes (pages 2776–2779)

      Zhen Wang, Zhenling Chen, Sha Bai, Wei Li, Prof. Dr. Xiaohua Liu, Dr. Lili Lin and Prof. Dr. Xiaoming Feng

      Version of Record online: 3 FEB 2012 | DOI: 10.1002/anie.201109130

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      Highly selective: The title reaction is achieved with high enantiomeric and geometric control and thermodynamically unstable (Z)-enone derivatives are obtained as the major products (see scheme). The procedure tolerates a wide range of substrates to generate optically active pyrazolones with vinyl-substituted quaternary stereocenters.

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