Angewandte Chemie International Edition

Cover image for Vol. 53 Issue 37

September 8, 2014

Volume 53, Issue 37

Pages 9677–9960

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlight
    12. Minireview
    13. Review
    14. Communications
    1. Cover Picture: Ultra-Low-Field NMR Relaxation and Diffusion Measurements Using an Optical Magnetometer (Angew. Chem. Int. Ed. 37/2014) (page 9677)

      Paul J. Ganssle, Hyun D. Shin, Dr. Scott J. Seltzer, Dr. Vikram S. Bajaj, Dr. Micah P. Ledbetter, Prof. Dmitry Budker, Dr. Svenja Knappe, Dr. John Kitching and Prof. Alexander Pines

      Article first published online: 30 JUL 2014 | DOI: 10.1002/anie.201406156

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      An optical magnetometer used for making ultra-low-field NMR measurements of relaxation and diffusion has the chemical sensitivity required to distinguish between hydrocarbons and water in Earth's magnetic field (0.5 G). P. J. Ganssle, A. Pines et al. describe in their Communication on page 9766 ff., this important proof-of-concept for the commercial applicability of these robust, portable NMR sensors, particularly in the context of oil-well logging.

    2. Inside Cover: Functionalized Graphene as a Gatekeeper for Chiral Molecules: An Alternative Concept for Chiral Separation (Angew. Chem. Int. Ed. 37/2014) (page 9678)

      Andreas W. Hauser, Narbe Mardirossian, Julien A. Panetier, Martin Head-Gordon, Alexis T. Bell and Peter Schwerdtfeger

      Article first published online: 15 JUL 2014 | DOI: 10.1002/anie.201406608

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      The attachment of a suitable “bouncer” molecule to the rim of a graphene pore prevents the passage of the undesired enantiomer while letting its mirror image through. In their Communication on page 9957 ff., A. W. Hauser, P. Schwerdtfeger et al. report that a small difference in the geometry of the temporary dimer complex, which is formed by the “bouncer” and the penetrating molecule, is transformed into a significant difference for the transmission barrier.

    3. Inside Back Cover: An Unusual Protein–Protein Interaction through Coupled Unfolding and Binding (Angew. Chem. Int. Ed. 37/2014) (page 9961)

      Tae-Kyung Yu, Seung-A Shin, Eun-Hee Kim, Dr. Sunghyun Kim, Dr. Kyung-Seok Ryu, Dr. Haekap Cheong, Prof. Dr. Hee-Chul Ahn, Prof. Dr. Sangyong Jon and Prof. Dr. Jeong-Yong Suh

      Article first published online: 7 JUL 2014 | DOI: 10.1002/anie.201406161

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      Protein–protein interactions can involve the folding of a disordered region to form the binding interface. In their Communication on page 9784 ff., J. Y. Suh and co-workers report the opposite case, in which binding is accompanied by local unfolding. The structure of an engineered peptide bound to fibronectin extradomain B reveals coupled unfolding and binding through β-strand displacement. The unfolding exposes a hydrophobic surface that provides key interactions for the complex.

    4. Back Cover: A High-Pressure NMR Probe for Aqueous Geochemistry (Angew. Chem. Int. Ed. 37/2014) (page 9962)

      Dr. Brent G. Pautler, Christopher A. Colla, Dr. Rene L. Johnson, Peter Klavins, Dr. Stephen J. Harley, Dr. C. André Ohlin, Prof. Dimitri A. Sverjensky, Dr. Jeffrey H. Walton and Prof. William H. Casey

      Article first published online: 22 JUL 2014 | DOI: 10.1002/anie.201406751

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      Geochemical models for aqueous solution equilibria extend to pressures and temperatures well beyond experimental spectroscopies that could test the predictions. W. H. Casey and co-workers describe in their Communication on page 9788 ff. a simple NMR probe that can allow spectroscopy on solutions at pressures near those of the Earth's continental crust. (Greg Pautler Graphic Design, Ontario, Canada, is thanked for designing and donating the artwork.)

  2. Frontispiece

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlight
    12. Minireview
    13. Review
    14. Communications
    1. Frontispiece: Selective Photoelectrochemical Reduction of Aqueous CO2 to CO by Solvated Electrons

      Linghong Zhang, Di Zhu, Prof. Gilbert M. Nathanson and Prof. Robert J. Hamers

      Article first published online: 2 SEP 2014 | DOI: 10.1002/anie.201483771

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      Photochemistry The efficient and selective reduction of CO2 to CO using solvated electrons, generated by illumination of inexpensive diamond substrates with UV light, is described by R. J. Hamers and co-workers in their Communication on page 9746 ff.

  3. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlight
    12. Minireview
    13. Review
    14. Communications
    1. Graphical Abstract: Angew. Chem. Int. Ed. 37/2014 (pages 9681–9695)

      Article first published online: 2 SEP 2014 | DOI: 10.1002/anie.201490035

  4. Corrigenda

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlight
    12. Minireview
    13. Review
    14. Communications
    1. You have free access to this content
      Corrigendum: Crowdsourcing Natural Products Discovery to Access Uncharted Dimensions of Fungal Metabolite Diversity (page 9695)

      Dr. Lin Du, Andrew J. Robles, Jarrod B. King, Dr. Douglas R. Powell, Prof. Dr. Andrew N. Miller, Prof. Dr. Susan L. Mooberry and Prof. Dr. Robert H. Cichewicz

      Article first published online: 2 SEP 2014 | DOI: 10.1002/anie.201407500

      This article corrects:

      Crowdsourcing Natural Products Discovery to Access Uncharted Dimensions of Fungal Metabolite Diversity1

      Vol. 53, Issue 3, 804–809, Article first published online: 27 NOV 2013

    2. You have free access to this content
  5. News

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlight
    12. Minireview
    13. Review
    14. Communications
  6. Author Profile

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlight
    12. Minireview
    13. Review
    14. Communications
    1. Andrew I. Cooper (page 9702)

      Article first published online: 2 JUL 2014 | DOI: 10.1002/anie.201402749

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      “My favorite scientific principle is thermodynamics. You can't beat it. My favorite quote is “It is not even wrong!” (attr. Wolfgang Pauli). …” This and more about Andrew I. Cooper can be found on page 9702.

  7. News

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlight
    12. Minireview
    13. Review
    14. Communications
  8. Obituary

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlight
    12. Minireview
    13. Review
    14. Communications
    1. Carlos F. Barbas III (19642014) (pages 9704–9705)

      Prof. Dr. Phil S. Baran

      Article first published online: 31 JUL 2014 | DOI: 10.1002/anie.201407049

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  9. Book Review

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlight
    12. Minireview
    13. Review
    14. Communications
    1. Bioinorganic Chemistry. By Dieter Rehder. (page 9706)

      Felix Zelder

      Article first published online: 21 AUG 2014 | DOI: 10.1002/anie.201406318

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      Oxford University Press, Oxford, 2014. 240 pp., hardcover, £ 34.99.—ISBN 978-0199655199

  10. Highlight

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlight
    12. Minireview
    13. Review
    14. Communications
    1. Cycloadditions

      Münchnones—New Facets after 50 Years (pages 9708–9710)

      Prof. Dr. Hans-Ulrich Reissig and Dr. Reinhold Zimmer

      Article first published online: 18 JUL 2014 | DOI: 10.1002/anie.201405092

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      Developed and named 50 years ago in Munich, the mesoionic münchnones have had an astonishing career. New multicomponent reactions and enantioselective cycloadditions are discussed. They demonstrate the versatility of the münchnone approach to nitrogen heterocycles.

  11. Minireview

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlight
    12. Minireview
    13. Review
    14. Communications
    1. Bioinorganic Chemistry

      Carbon-Monoxide-Releasing Molecules for the Delivery of Therapeutic CO In Vivo (pages 9712–9721)

      Dr. Sandra García-Gallego and Dr. Gonçalo J. L. Bernardes

      Article first published online: 28 JUL 2014 | DOI: 10.1002/anie.201311225

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      On target: Carbon-monoxide-releasing molecules (CORMs) are promising agents for the treatment of several diseases. CORMs are particularly good for enabling CO delivery in a controlled manner without affecting oxygen transport by hemoglobin. Significant progress in the methods for CO detection in live cells and the understanding of the reactivity of CORMs in vivo provides insights into CO biology and the design of safer, and more selective and efficient CORMs for clinical use.

  12. Review

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlight
    12. Minireview
    13. Review
    14. Communications
    1. Polyolefins

      Post-Metallocenes in the Industrial Production of Polyolefins (pages 9722–9744)

      M. Sc. Moritz C. Baier, Dr. Martin A. Zuideveld and Prof. Dr. Stefan Mecking

      Article first published online: 21 AUG 2014 | DOI: 10.1002/anie.201400799

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      “Post-metallocene” polymerization catalysis research ranges from fundamental mechanistic studies by catalyst design to material properties of polyolefins. A common goal of these studies is the creation of practically useful new materials or processes. A comprehensive overview of post-metallocene polymerization catalysts that have been put into practice is provided. The decisive properties for this success of a given catalyst structure are delineated.

  13. Communications

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlight
    12. Minireview
    13. Review
    14. Communications
    1. Photochemistry | Hot Paper

      Selective Photoelectrochemical Reduction of Aqueous CO2 to CO by Solvated Electrons (pages 9746–9750)

      Linghong Zhang, Di Zhu, Prof. Gilbert M. Nathanson and Prof. Robert J. Hamers

      Article first published online: 14 JUL 2014 | DOI: 10.1002/anie.201404328

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      Diamond in the rough: Illumination of diamond substrates leads to emission of electrons into aqueous media. The solvated electrons are potent reducing agents and induce the direct one-electron reduction of CO2 to CO2.−, which then forms CO. This approach represents a new concept in catalysis by directly releasing electrons into reactant liquids.

    2. Protein Dynamics | Hot Paper

      Local Transient Unfolding of Native State PAI-1 Associated with Serpin Metastability (pages 9751–9754)

      Dr. Morten B. Trelle, Dr. Jeppe B. Madsen, Prof. Peter A. Andreasen and Prof. Dr. Thomas J. D. Jørgensen

      Article first published online: 22 JUL 2014 | DOI: 10.1002/anie.201402796

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      Serpin proteins are prone to pathological conformational change, for instance by conversion into an inactive, so-called latent form. By using advanced hydrogen/deuterium-exchange mass spectrometry, transient unfolding of a serpin is shown under native conditions. Based on these observations, a new mechanism (see picture) is proposed.

    3. Biomass Conversion

      Pd/NbOPO4 Multifunctional Catalyst for the Direct Production of Liquid Alkanes from Aldol Adducts of Furans (pages 9755–9760)

      Qi-Neng Xia, Qian Cuan, Xiao-Hui Liu, Prof. Xue-Qing Gong, Prof. Guan-Zhong Lu and Prof. Yan-Qin Wang

      Article first published online: 18 JUL 2014 | DOI: 10.1002/anie.201403440

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      Fueling fuel production: Biomass conversion into liquid fuel depends on the design of multifunctional catalysts. In the direct conversion of furan-based aldol adducts into liquid alkanes over a Pd/NbOPO4 catalyst under mild conditions (see scheme), NbOx species played an important role in C[BOND]O bond cleavage.

    4. Lewis Acids

      Highly Electron-Deficient and Air-Stable Conjugated Thienylboranes (pages 9761–9765)

      Dr. Xiaodong Yin, Jiawei Chen, Prof. Roger A. Lalancette, Prof. Dr. Todd B. Marder and Prof. Dr. Frieder Jäkle

      Article first published online: 17 JUL 2014 | DOI: 10.1002/anie.201403700

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      The bigger the better: Sterically demanding 2,4,6-tri-tert-butylphenyl (Mes*) or 2,4,6-tris(trifluoromethyl)phenyl (FMes) groups do not prevent but rather promote coplanarity and enhance electronic communication within conjugated thienylboranes. FMes exerts a strong electron-withdrawing effect which results in significant lowering of the LUMO energy level and high Lewis acidity toward fluoride anions, while ensuring stability in air and towards acid or base.

    5. NMR Spectroscopy | Hot Paper

      Ultra-Low-Field NMR Relaxation and Diffusion Measurements Using an Optical Magnetometer (pages 9766–9770)

      Paul J. Ganssle, Hyun D. Shin, Dr. Scott J. Seltzer, Dr. Vikram S. Bajaj, Dr. Micah P. Ledbetter, Prof. Dmitry Budker, Dr. Svenja Knappe, Dr. John Kitching and Prof. Alexander Pines

      Article first published online: 31 JUL 2014 | DOI: 10.1002/anie.201403416

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      Portable NMR: NMR relaxometry and diffusometry can be highly effective in applications where high-resolution NMR spectroscopy is unnecessary or impractical, as is the case in the emerging field of portable chemical characterization. A proof-of-concept experiment is presented that demonstrates the use of high-sensitivity optical magnetometers as detectors for ultra-low-field NMR relaxation and diffusion measurements.

    6. Molecular Electronics

      Orientation-Controlled Single-Molecule Junctions (pages 9771–9774)

      Sepideh Afsari, Dr. Zhihai Li and Prof. Dr. Eric Borguet

      Article first published online: 15 JUL 2014 | DOI: 10.1002/anie.201402343

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      The conductivity of a single aromatic ring, perpendicular to its plane, is determined (see picture; I=current). The formation of highly ordered structures of mesitylene oriented parallel to an Au (111) plane enables direct contact between a scanning tunneling microscopy tip and the π-system of mesitylene to create highly conductive Au/aromatic/Au junctions under ambient conditions.

    7. Membrane Preparation | Hot Paper

      Coordination-Driven In Situ Self-Assembly Strategy for the Preparation of Metal–Organic Framework Hybrid Membranes (pages 9775–9779)

      Rong Zhang, Prof. Shulan Ji, Dr. Naixin Wang, Lin Wang, Prof. Guojun Zhang and Jian-Rong Li

      Article first published online: 22 JUL 2014 | DOI: 10.1002/anie.201403978

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      Mopping up the mess: A hybrid membrane composed of the metal–organic framework (MOF) ZIF-8 and poly(sodium 4-styrenesulfonate) was prepared by a coordination-driven in situ self-assembly method. The MOF particles were well-dispersed in the polymer in the resulting stable membrane (see picture), which showed excellent performance in the nanofiltration and separation of dyes from water.

    8. Solid Electrolytes

      Poly(dimethylsiloxane)-Supported Ionogels with a High Ionic Liquid Loading (pages 9780–9783)

      Ariel I. Horowitz and Prof. Matthew J. Panzer

      Article first published online: 15 JUL 2014 | DOI: 10.1002/anie.201405691

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      Supportive, despite their differences: The immiscibility of poly(dimethylsiloxane) (PDMS) and ionic liquids (ILs) has been overcome by a simple sol–gel reaction (see picture) to create PDMS-supported ILs (ionogels) with IL loadings of up to 80 % by mass. The ionogels exhibited high ionic conductivity and excellent mechanical behavior, with an elastic modulus of approximately 60 kPa without fatigue over 5000 cycles, even at elevated temperatures.

    9. Protein–Protein Interactions | Hot Paper

      An Unusual Protein–Protein Interaction through Coupled Unfolding and Binding (pages 9784–9787)

      Tae-Kyung Yu, Seung-A Shin, Eun-Hee Kim, Dr. Sunghyun Kim, Dr. Kyung-Seok Ryu, Dr. Haekap Cheong, Prof. Dr. Hee-Chul Ahn, Prof. Dr. Sangyong Jon and Prof. Dr. Jeong-Yong Suh

      Article first published online: 1 JUL 2014 | DOI: 10.1002/anie.201404750

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      Unfold and hold: It is known that protein–protein interactions can involve coupled folding and binding, but coupled unfolding and binding is not well characterized. An unusual protein–protein interaction is described in which the binding of an aptide (APT) to fibronectin extradomain B (EDB) involves partial unfolding to expose the binding surface. The structural and energetic details were determined by NMR spectroscopy and thermodynamic analysis.

    10. High-Pressure NMR Spectroscopy | Very Important Paper

      A High-Pressure NMR Probe for Aqueous Geochemistry (pages 9788–9791)

      Dr. Brent G. Pautler, Christopher A. Colla, Dr. Rene L. Johnson, Peter Klavins, Dr. Stephen J. Harley, Dr. C. André Ohlin, Prof. Dimitri A. Sverjensky, Dr. Jeffrey H. Walton and Prof. William H. Casey

      Article first published online: 2 JUL 2014 | DOI: 10.1002/anie.201404994

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      A non-magnetic piston-cylinder pressure cell has been developed for solution-state NMR spectroscopy up to 20 kbar for aqueous geochemical applications. 11B NMR spectroscopic investigations into the H3BO3–catechol equilibrium demonstrates a large pressure-driven exchange rate. The success of these experiments suggests that this probe design can be applied to a wide variety of NMR-active nuclei.

    11. Polymer Sensors

      Fluorescence Sensing of Amine Vapors Using a Cationic Conjugated Polymer Combined with Various Anions (pages 9792–9796)

      Dr. Sébastien Rochat and Prof. Dr. Timothy M. Swager

      Article first published online: 18 JUL 2014 | DOI: 10.1002/anie.201404439

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      A sensor array comprising a conjugated cationic polymer combined with various counteranions has been developed. This simple approach allows the creation of polymer formulations able to detect vapors of industrially relevant amines in low ppm concentrations by fluorescence quenching measurements. Furthermore the array's response is useful to identify the nature of the analyte through pattern-based recognition algorithms.

    12. Photophysics

      UV Excited-State Photoresponse of Biochromophore Negative Ions (pages 9797–9801)

      Dr. Anastasia V. Bochenkova, Dr. Benedikte Klærke, Dr. Dennis B. Rahbek, Dr. Jyoti Rajput, Dr. Yoni Toker and Prof. Lars H. Andersen

      Article first published online: 15 JUL 2014 | DOI: 10.1002/anie.201404609

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      Higher electronically excited states of the green fluorescent protein chromophore anion have been probed directly by action absorption spectroscopy. The high density of these UV molecular resonances in the UV makes electron detachment in the gas phase efficient. Quantum calculations show this electronic band inside the protein to be resonant with the quasicontinuum of a solvated electron, thus suggesting its major role in the photophysics in the UV region.

    13. Nitrogen Photofixation | Hot Paper

      Plasmon-Induced Ammonia Synthesis through Nitrogen Photofixation with Visible Light Irradiation (pages 9802–9805)

      Dr. Tomoya Oshikiri, Prof. Kosei Ueno and Prof. Hiroaki Misawa

      Article first published online: 17 JUL 2014 | DOI: 10.1002/anie.201404748

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      See the light of day: A plasmon-induced ammonia synthesis technique that responds to visible light and is based on a strontium titanate (SrTiO3) photoelectrode loaded with gold nanoparticles has been developed. It is deduced that plasmon-induced charge separation at the Au/SrTiO3 interface promotes oxidation in the anodic chamber and subsequent nitrogen reduction on the cathodic side.

    14. Biocatalysis | Hot Paper

      Unprecedented Role of Hydronaphthoquinone Tautomers in Biosynthesis (pages 9806–9811)

      Dr. Syed Masood Husain, Dr. Michael A. Schätzle, Dr. Steffen Lüdeke and Prof. Dr. Michael Müller

      Article first published online: 22 JUL 2014 | DOI: 10.1002/anie.201404560

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      Breaking the cycle: In studies on the reduction of 2-hydroxynaphthoquinones to the stable 1,4-diketo tautomeric form of hydronaphthoquinones and their further reduction by fungal tetrahydroxynaphthalene reductase, diketo tautomers emerge as true intermediates in biosynthesis. Their formation breaks the (redox) cycle, thus protecting the cell from stress-related redox events.

    15. Glycopeptides

      Synthesis of the Highly Glycosylated Hydrophilic Motif of Extensins (pages 9812–9816)

      Dr. Akihiro Ishiwata, Dr. Sophon Kaeothip, Dr. Yoichi Takeda and Dr. Yukishige Ito

      Article first published online: 15 JUL 2014 | DOI: 10.1002/anie.201404904

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      Just a phase: Stereoselective synthesis of one of the highly glycosylated hydrophilic motifs of extensins has been completed. Key steps were a 2-naphthylmethyl ether-mediated intramolecular aglycon delivery to the stereoselective construction of the Ser(Galp1) and Hyp(Arafn) (n=1, 3, 4) fragments and Fmoc solid-phase peptide synthesis (SPPS) for the highly glycosylated pentapeptide motif.

    16. Gold–Carbenoids

      Chemoselective Carbophilic Addition of α-Diazoesters through Ligand-Controlled Gold Catalysis (pages 9817–9821)

      Yumeng Xi, Yijin Su, Zhaoyuan Yu, Boliang Dong, Edward J. McClain, Prof. Yu Lan and Prof. Xiaodong Shi

      Article first published online: 23 JUL 2014 | DOI: 10.1002/anie.201404946

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      Carbocation or carbene? The chemoselective addition of arenes and 1,3-diketones to α-aryldiazoesters was achieved through ligand-controlled gold catalysis. The gold catalyst with electron-deficient phosphite as the ancillary ligand exclusively gave the carbophilic addition products, thus representing a new and efficient approach to form “carbophilic carbocations”, which selectively react with carbon nucleophiles.

    17. Luminescence Imaging

      Image-Contrast Technology Based on the Electrochemiluminescence of Porous Silicon and Its Application in Fingerprint Visualization (pages 9822–9826)

      Jie Tan, Linru Xu, Tong Li, Prof. Bin Su and Prof. Jianmin Wu

      Article first published online: 17 JUL 2014 | DOI: 10.1002/anie.201404948

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      Fit for a modern Sherlock: Electrochemiluminescence by porous silicon (pSi) has a regular dynamic process involving activation, strong emission, and fading. This process can be perturbed by chemicals adsorbed on the pSi surface. The contrast in luminescence intensity between adjacent areas with different surface chemistry enabled the visualization of latent fingerprints and a trinitrotoluene (TNT) residue in a fingerprint with high resolution (see picture).

    18. Metal–Metal Interactions

      First Stabilization of 14-Electron Rhodium(I) Complexes by Hemichelation (pages 9827–9831)

      Christophe Werlé, Corinne Bailly, Dr. Lydia Karmazin-Brelot, Xavier-Frédéric Le Goff, Dr. Michel Pfeffer and Dr. Jean-Pierre Djukic

      Article first published online: 17 JUL 2014 | DOI: 10.1002/anie.201405240

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      Touching from a distance: The syntheses of unprecedented T-shaped 14-electron RhI hemichelates is made possible by choosing the anti-[(η66-fluorenyl){Cr(CO)3}2]-based benzylic anion as an ambiphilic hemichelating ligand, and treating it with [{Rh(nbd)Cl}2] (nbd=norbornadiene) or [{Rh(CO)2Cl}2].

    19. Self-Assembly

      A Supramolecular Sorting Hat: Stereocontrol in Metal–Ligand Self-Assembly by Complementary Hydrogen Bonding (pages 9832–9836)

      Michael C. Young, Lauren R. Holloway, Amber M. Johnson and Prof. Richard J. Hooley

      Article first published online: 17 JUL 2014 | DOI: 10.1002/anie.201405242

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      Abracadabra: The stereoselective self-assembly of an unsymmetrical metal–ligand cage can be controlled by self-complementary hydrogen bonding between alcohol-containing ligands as well as between ligands and suitable anion guests.

    20. Noncovalent Interactions

      Understanding a Host–Guest Model System through 129Xe NMR Spectroscopic Experiments and Theoretical Studies (pages 9837–9840)

      Emmanuelle Dubost, Jean-Pierre Dognon, Bernard Rousseau, Gaëlle Milanole, Christophe Dugave, Yves Boulard, Estelle Léonce, Céline Boutin and Patrick Berthault

      Article first published online: 22 JUL 2014 | DOI: 10.1002/anie.201405349

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      How hosts handle a noble guest: A combination of NMR spectroscopy and quantum chemistry enabled thorough analysis of the noncovalent interactions inside a xenon–host complex. The validation of this approach with a family of cryptophane hosts derived by treatment of the structure shown with H2O2 paves the way for the design of potent smart hyperpolarized 129Xe NMR sensors.

    21. Cancer Immunotherapy

      Targeting Human C-Type Lectin-like Molecule-1 (CLL1) with a Bispecific Antibody for Immunotherapy of Acute Myeloid Leukemia (pages 9841–9845)

      Dr. Hua Lu, Dr. Quan Zhou, Vishal Deshmukh, Dr. Hardeep Phull, Dr. Jennifer Ma, Dr. Virginie Tardif, Dr. Rahul R. Naik, Dr. Claire Bouvard, Dr. Yong Zhang, Dr. Seihyun Choi, Dr. Brian R. Lawson, Dr. Shoutian Zhu, Dr. Chan Hyuk Kim and Dr. Peter G. Schultz

      Article first published online: 23 JUL 2014 | DOI: 10.1002/anie.201405353

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      A bispecific antibody, αCLL1-αCD3, was synthesized using a genetically encoded unnatural amino acid, and shown to recruit cytotoxic T cells to CLL1-positive cells. The reported results validate the clinical potential of CLL1 as an AML-specific antigen for the generation of bispecific antibodies for the treatment of acute myeloid leukemia (AML).

    22. Homologation | Very Important Paper

      Stereocontrolled Synthesis of 1,5-Stereogenic Centers through Three-Carbon Homologation of Boronic Esters (pages 9846–9850)

      Phillip J. Unsworth, Dr. Daniele Leonori and Prof. Varinder K. Aggarwal

      Article first published online: 15 JUL 2014 | DOI: 10.1002/anie.201405700

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      Three more: The 3C homologation of chiral pinacol boronic esters gives di- or trisubstituted allylic boronic esters with high yield and E selectivities. The combination of this method with lithiation–borylation enables the synthesis of alkyl chains that bear 1,5-stereogenic centers. The utility of the process was demonstrated in a formal synthesis of (+)-jasplakinolide.

    23. C[BOND]H Functionalization

      Simple Sulfinate Synthesis Enables C[BOND]H Trifluoromethylcyclopropanation (pages 9851–9855)

      Ryan Gianatassio, Dr. Shuhei Kawamura, Cecil L Eprile, Dr. Klement Foo, Jason Ge, Dr. Aaron C. Burns, Dr. Michael R. Collins and Prof. Dr. Phil S. Baran

      Article first published online: 3 AUG 2014 | DOI: 10.1002/anie.201406622

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      An interrupted Barton decarboxylation reaction has been used to convert readily available carboxylic acids into sulfinate salts (see scheme). Ten new sulfinate reagents were created and the reactivity of six of them towards C[BOND]H functionalization was tested on a range of heterocycles. The simplicity of this approach (a cheap industrial oxidant, simple solvent, and no metals) is a clear advantage over other radical donors.

    24. Water Oxidation

      Ligand Modification Transforms a Catalase Mimic into a Water Oxidation Catalyst (pages 9856–9859)

      Dr. Wei-Tsung Lee, Salvador B. Muñoz III, Dr. Diane A. Dickie and Prof. Jeremy M. Smith

      Article first published online: 15 JUL 2014 | DOI: 10.1002/anie.201402407

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      Ligand-controlled switch: Simple modification of the substituent on a pyridinophane macrocycle ligand converts the corresponding MnII complex from a hydrogen peroxide disproportionation catalyst into a water oxidation catalyst. Preliminary results indicate that the catalyst is mononuclear.

    25. Asymmetric Synthesis

      Asymmetric Hydroxylative Phenol Dearomatization Promoted by Chiral Binaphthylic and Biphenylic Iodanes (pages 9860–9864)

      Cyril Bosset, Romain Coffinier, Dr. Philippe A. Peixoto, Mourad El Assal, Dr. Karinne Miqueu, Dr. Jean-Marc Sotiropoulos, Dr. Laurent Pouységu and Prof. Stéphane Quideau

      Article first published online: 22 JUL 2014 | DOI: 10.1002/anie.201403571

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      The selective oxygenation of iodobinaphthyls and iodobiphenyls afforded either λ3- or λ5-iodanes, which were evaluated for their capacity to promote asymmetric intermolecular hydroxylative phenol dearomatizations (HPDs). Most remarkably, a C2-symmetrical biphenylic λ5-iodane induced the HPD reaction/[4+2] cyclodimerization cascade of thymol into bis(thymol) with enantiomeric excesses of up to 94 %.

    26. Cycloaddition

      [HCo(CO)4]-Catalyzed Three-component Cycloaddition of Epoxides, Imines, and Carbon Monoxide: Facile Construction of 1,3-Oxazinan-4-ones (pages 9865–9869)

      Lixia Liu and Prof. Huailin Sun

      Article first published online: 18 JUL 2014 | DOI: 10.1002/anie.201403998

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      Cobalt and CO: The title reaction is described to proceed in the presence of [HCo(CO)4] as the catalyst. The reaction occurs for a wide variety of imines and various substituted epoxides, thus providing an efficient and atom-economic route to 1,3-oxazinan-4-ones, with various substitution patterns, from simple and readily available starting materials.

    27. Flavin Fluorescence

      A Conical Intersection Controls the Deactivation of the Bacterial Luciferase Fluorophore (pages 9870–9875)

      Dr. Samer Gozem, Dr. Ekaterina Mirzakulova, Dr. Igor Schapiro, Dr. Federico Melaccio, Prof. Dr. Ksenija D. Glusac and Prof. Dr. Massimo Olivucci

      Article first published online: 14 JUL 2014 | DOI: 10.1002/anie.201404011

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      How nature lights up flavins: 4a-hydroxy flavins display weak fluorescence and ultrafast excited-state decay in solution, but exhibit strong fluorescence when produced in a protein cavity. A joint experimental and theoretical study explains the fluorescence properties of these flavin adducts in terms of a deactivation pathway mediated by a conical intersection that becomes inaccessible in sterically constrained environments.

    28. Carbohydrates

      Synthesis of the Heparin-Based Anticoagulant Drug Fondaparinux (pages 9876–9879)

      Dr. Cheng-Hsiu Chang, Larry S. Lico, Dr. Teng-Yi Huang, Dr. Shu-Yi Lin, Dr. Chi-Liang Chang, Prof. Dr. Susan D. Arco and Prof. Dr. Shang-Cheng Hung

      Article first published online: 15 JUL 2014 | DOI: 10.1002/anie.201404154

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      Working against the clot: The synthetic anticoagulant fondaparinux, a pentasaccharide based on the antithrombin-binding domain of heparin, was prepared in a concise and efficient manner in the shortest route reported to date. The application of one-pot strategies, the use of common intermediates, and the efficient preparation of monosaccharide building blocks from commercial sources are key features of this approach.

    29. Strained Polycycles

      Synthesis of Bridged Oxafenestranes from Pleuromutilin (pages 9880–9883)

      Robert W. Hicklin, Tania L. López Silva and Prof. Paul J. Hergenrother

      Article first published online: 17 JUL 2014 | DOI: 10.1002/anie.201404765

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      Fenestranes are highly strained molecules possessing a quaternary carbon atom with bonds that deviate from the canonical tetrahedral geometry. The natural product pleuromutilin can be used as a starting material for the synthesis of bridged [4.5.5.5]- and [4.5.7.5]oxafenestranes through a carbocation rearrangement cascade. X-ray crystallography shows that these compounds exhibit significant planarization of the central tetracoordinate carbon center.

    30. C[BOND]H Activation

      Easily Accessible Auxiliary for Palladium-Catalyzed Intramolecular Amination of C(sp2)[BOND]H and C(sp3)[BOND]H Bonds at δ- and ε-Positions (pages 9884–9888)

      Chao Wang, Changpeng Chen, Jingyu Zhang, Jian Han, Qian Wang, Kun Guo, Pei Liu, Mingyu Guan, Dr. Yingming Yao and Prof. Dr. Yingsheng Zhao

      Article first published online: 22 JUL 2014 | DOI: 10.1002/anie.201404854

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      Remote access: The first application of an oxalyl amide to direct C[BOND]H functionalizations at remote positions is reported. The results show both C(sp2)[BOND]H and C(sp3)[BOND]H bonds at δ- and ε-positions are effectively activated, thus giving tetrahydroquinolines, benzomorpholines, pyrrolidines, and indolines in moderate to excellent yields by palladium-catalyzed intramolecular C[BOND]H amination.

    31. Multiple C[BOND]H Activation | Hot Paper

      One-Pot Synthesis of Highly Substituted Polyheteroaromatic Compounds by Rhodium(III)-Catalyzed Multiple C[BOND]H Activation and Annulation (pages 9889–9892)

      Jayachandran Jayakumar, Dr. Kanniyappan Parthasarathy, Yi-Hsiang Chen, Tai-Hua Lee, Prof. Dr. Shih-Ching Chuang and Prof. Dr. Chien-Hong Cheng

      Article first published online: 17 JUL 2014 | DOI: 10.1002/anie.201405183

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      Activated and annulated: A rhodium-catalyzed one-pot synthesis of highly substituted polyheteroaromatic compounds from N-hydroxybenzamidines and alkynes is described. This reaction likely proceeds through multiple C[BOND]H bond activation and annulation.

    32. Modified Nucleosides

      Synthesis and Duplex-Stabilizing Properties of Fluorinated N-Methanocarbathymidine Analogues Locked in the C3′-endo Conformation (pages 9893–9897)

      Michael E. Jung, Timothy A. Dwight, Frederic Vigant, Michael E. Østergaard, Eric E. Swayze and Punit P. Seth

      Article first published online: 15 JUL 2014 | DOI: 10.1002/anie.201405283

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      The power of conviction: The efficient synthesis, antiviral activity, and duplex-stabilizing properties of both isomers, A and B, of the 2′-fluoro analogue of N-methanocarbathymidine (N-MCT) are reported. Incorporation of the fluorine substituent at the 2′-position of the N-MCT scaffold was found to have a strong positive effect on duplex thermal stability.

    33. Perovskite Solar Cells | Hot Paper

      A Fast Deposition-Crystallization Procedure for Highly Efficient Lead Iodide Perovskite Thin-Film Solar Cells (pages 9898–9903)

      Manda Xiao, Dr. Fuzhi Huang, Wenchao Huang, Yasmina Dkhissi, Dr. Ye Zhu, Prof. Dr. Joanne Etheridge, Dr. Angus Gray-Weale, Prof. Dr. Udo Bach, Prof. Dr. Yi-Bing Cheng and Prof. Dr. Leone Spiccia

      Article first published online: 22 JUL 2014 | DOI: 10.1002/anie.201405334

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      Fast and thin: Flat, uniform thin films of CH3NH3PbI3 perovskites have been produced by a fast, one-step procedure involving spin-coating of a DMF solution of CH3NH3PbI3 and immediate exposure to chlorobenzene to induce crystallization. Planar heterojunction solar cells made with these films gave a maximum power conversion efficiency of 16.2 %.

    34. Heterocycles

      Expedient Synthesis of Fused Azepine Derivatives Using a Sequential Rhodium(II)-Catalyzed Cyclopropanation/1-Aza-Cope Rearrangement of Dienyltriazoles (pages 9904–9908)

      Erica E. Schultz, Vincent N. G. Lindsay and Prof. Richmond Sarpong

      Article first published online: 15 JUL 2014 | DOI: 10.1002/anie.201405356

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      A general method for the formation of fused dihydroazepines from 1-sulfonyl-1,2,3-triazoles bearing a tethered diene is reported. The process involves an intramolecular cyclopropanation of an α-imino rhodium(II) carbenoid, leading to a transient 1-imino-2-vinylcyclopropane intermediate which rapidly undergoes a 1-aza-Cope rearrangement to generate the products in moderate to excellent yields. Ts=4-toluenesulfonyl.

    35. Synthetic Methods

      Nickel-Catalyzed Cross-Coupling of Functionalized Difluoromethyl Bromides and Chlorides with Aryl Boronic Acids: A General Method for Difluoroalkylated Arenes (pages 9909–9913)

      Yu-Lan Xiao, Wen-Hao Guo, Guo-Zhen He, Qiang Pan and Prof. Dr. Xingang Zhang

      Article first published online: 17 JUL 2014 | DOI: 10.1002/anie.201405653

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      Simple and easy: The first example of a nickel-catalyzed difluoroalkylation of aryl boronic acids with functionalized difluoromethyl bromides and chlorides has been developed. This cross-coupling process features a broad substrate scope, a cheap catalyst, and excellent functional-group compatibility.

    36. Sustainable Chemistry

      An “All-Green” Catalytic Cycle of Aqueous Photoionization (pages 9914–9916)

      Prof. Dr. Martin Goez, Christoph Kerzig and Robert Naumann

      Article first published online: 22 JUL 2014 | DOI: 10.1002/anie.201405693

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      Green light and a cheap, even bioavailable, sacrificial donor produce hydrated electrons in the displayed catalytic cycle. The catalyst is a popular metal complex functioning as a “container” for a radical anion. The cycle could open a pathway toward the solar-driven reductive detoxification of halogenated organic waste. equation image=MeOPhO; equation image=MeOPhO.; MLCT=*[RuIII(bpy)2(bpy.)]2+; OER=[RuII(bpy)2(bpy.)]+; GS=[RuII(bpy)3]2+; bpy=2,2′-bipyridine.

    37. Self-Assembly | Hot Paper

      Reversible Supramolecular Assembly at Specific DNA Sites: Nickel-Promoted Bivalent DNA Binding with Designed Peptide and Bipyridyl–Bis(benzamidine) Components (pages 9917–9921)

      Mateo I. Sánchez, Jesús Mosquera, Prof.  M. Eugenio Vázquez and Prof. José L. Mascareñas

      Article first published online: 15 JUL 2014 | DOI: 10.1002/anie.201405726

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      Nickel(II) salts promote the assembly of a bis(histidine)-modified peptide that is derived from a bZIP transcription factor and a bipyridine-substituted bis(benzamidine) unit at specific DNA sites. This supramolecular system features some key properties of naturally occurring DNA-binding proteins, such as bivalence, selectivity, responsiveness to external agents, and reversibility.

    38. Electrocatalysis

      You have full text access to this OnlineOpen article
      Metal-Free Dihydrogen Oxidation by a Borenium Cation: A Combined Electrochemical/Frustrated Lewis Pair Approach (pages 9922–9925)

      Elliot J. Lawrence, Thomas J. Herrington, Dr. Andrew E. Ashley and Dr. Gregory G. Wildgoose

      Article first published online: 18 JUL 2014 | DOI: 10.1002/anie.201405721

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      The potential that is required for non-aqueous H2 oxidation at a carbon electrode can be significantly reduced by using a borenium cation in a combined electrochemical/frustrated Lewis pair approach. This system exhibits faster electrode kinetics, increased stability to electrogenerated protons, and improved catalyst recycling over a previously reported system that is based on the borane Lewis acid B(C6F5)3.

    39. Organocatalysis

      Phosphoric Acid Catalyzed Desymmetrization of Bicyclic Bislactones Bearing an All-Carbon Stereogenic Center: Total Syntheses of (−)-Rhazinilam and (−)-Leucomidine B (pages 9926–9930)

      Jean-Baptiste Gualtierotti, Delphine Pasche, Dr. Qian Wang and Prof. Dr. Jieping Zhu

      Article first published online: 22 JUL 2014 | DOI: 10.1002/anie.201405842

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      Breaking symmetry: Achiral bislactones (1) undergo desymmetrization by reaction with alcohol in the presence of chiral imidodiphosphoric acids. The monoacids 2, having an all-carbon stereogenic center, were obtained in good to excellent yields and enantioselectivities. Concise total syntheses of (−)-rhazinilam and (−)-leucomidine B were subsequently developed using 2 as a common starting material.

    40. C[BOND]H Functionalization

      Catalytic 1,4-Rhodium(III) Migration Enables 1,3-Enynes to Function as One-Carbon Oxidative Annulation Partners in C[BOND]H Functionalizations (pages 9931–9935)

      Dr. David J. Burns and Prof. Hon Wai Lam

      Article first published online: 22 JUL 2014 | DOI: 10.1002/anie.201406072

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      When two become one: 1,3-Enynes containing allylic hydrogen atoms cis to the alkyne are shown to act as one-carbon partners, rather than two-carbon partners, in various rhodium-catalyzed oxidative annulations. The mechanism of these unexpected transformations is proposed to occur through double C[BOND]H activation, involving a hitherto rare example of the 1,4-migration of a RhIII species.

    41. Asymmetric Catalysis

      High Performance of a Palladium Phosphinooxazoline Catalyst in the Asymmetric Arylation of Cyclic N-Sulfonyl Ketimines (pages 9936–9939)

      Chunhui Jiang, Prof. Dr. Yixin Lu and Prof. Dr. Tamio Hayashi

      Article first published online: 18 JUL 2014 | DOI: 10.1002/anie.201406147

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      Chiral cyclic sulfamidates are obtained by the asymmetric addition of arylboronic acids to six-membered cyclic N-sulfonyl ketimines. A cationic palladium complex with a chiral phosphine-oxazoline ligand (iPr-phox) shows high catalytic activity and enantioselectivity to give the products in high yields with 96–99.9 % ee. The cyclic sulfamidates exhibit a tetrasubstituted stereogenic center with an amino group and a triaryl or alkyldiaryl group as substituents.

    42. Dihydrogen Bonding

      Evidence of Dihydrogen Bonding of a Chiral Amine–Borane Complex in Solution by VCD Spectroscopy (pages 9940–9943)

      Dr. Christian Merten, Christopher J. Berger, Dr. Robert McDonald and Prof. Dr. Yunjie Xu

      Article first published online: 15 JUL 2014 | DOI: 10.1002/anie.201403690

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      A chiral amine–borane is investigated by vibrational circular dichroism (VCD) spectroscopy. By comparison of experimental and calculated spectra, a unique VCD pattern associated with the formation of dihydrogen-bonded dimers in solution is identified. Different dihydrogen binding arrangements in solution and in the solid state are characterized.

    43. Single-Electron-Transfer Catalysis

      Oxidative Catalysis Using the Stoichiometric Oxidant as a Reagent: An Efficient Strategy for Single-Electron-Transfer-Induced Tandem Anion–Radical Reactions (pages 9944–9948)

      Ing. František Kafka, Ing. Martin Holan, M.Sc. Denisa Hidasová, Dr. Radek Pohl, Dr. Ivana Císařová, Dr. Blanka Klepetářová and Dr. Ullrich Jahn

      Article first published online: 28 JUL 2014 | DOI: 10.1002/anie.201403776

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      Making waste a functionality: Oxidative electron-transfer-mediated anion–radical transformations are rendered catalytic by employing a 2,2,6,6-tetramethyl-N-oxopiperidinium salt and ferrocene. The method provides an asymmetric approach to highly functionalized cyclopentane and pyrrolidine derivatives. At the same time the co-generated reduced species TEMPO serves as a useful oxygenating functionality.

    44. Iodine Adsorption

      Adsorption of I2 by Macrocyclic Polyazadithiophenolato Complexes Mediated by Charge-Transfer Interactions (pages 9949–9952)

      Matthias Golecki, Norman Beyer, Dr. Gunther Steinfeld, Dr. Vasile Lozan, Dr. Sergei Voitekhovich, Dr. Muhamed Sehabi, Dr. Jens Möllmer, Prof. Dr. Hans-Jörg Krüger and Prof. Dr. Berthold Kersting

      Article first published online: 30 JUL 2014 | DOI: 10.1002/anie.201405199

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      Seeing I to I: The macrocyclic complex [Ni2(L)(OAc)]ClO4 (1) adsorbs up to 17 molar equivalents (>270 wt %) of iodine, although it does not exhibit permanent porosity. IR and crystallographic studies reveal that two I2 molecules are captured by means of thiophenolate[RIGHTWARDS ARROW]I2 charge-transfer interactions, which enable the diffusion and sorption of further I2 molecules in a polyiodide-like network.

    45. Group 14 Chemistry

      N-Heterocyclic Carbene Coordinated Neutral and Cationic Heavier Cyclopropylidenes (pages 9953–9956)

      Dr. Anukul Jana, Dipl.-Chem. Isabell Omlor, Dr. Volker Huch, Prof. Dr. Henry S. Rzepa and Prof. Dr. David Scheschkewitz

      Article first published online: 24 JUL 2014 | DOI: 10.1002/anie.201405238

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      He is heavy and he′s my brother: NHC-coordinated cyclopropenylidene analogues with molecular scaffolds exclusively formed by heavier Group 14 elements are accessible from the corresponding vinylidene isomers by exchange of the NHC ligand for a smaller NHC. The residual chloride in one of these heavier cyclic carbenes can be expelled by a second equivalent of NHC to generate cationic derivatives of the imidazolium type.

    46. Chiral Separation

      Functionalized Graphene as a Gatekeeper for Chiral Molecules: An Alternative Concept for Chiral Separation (pages 9957–9960)

      Andreas W. Hauser, Narbe Mardirossian, Julien A. Panetier, Martin Head-Gordon, Alexis T. Bell and Peter Schwerdtfeger

      Article first published online: 13 JUL 2014 | DOI: 10.1002/anie.201403145

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      Selective entry: A mixture of enantiomers can be separated with functionalized nanoporous graphene. Density functional calculations indicate that a “bouncer” molecule attached to the pore rim prevents the passage of the undesired enantiomer while letting its mirror image through.

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