Angewandte Chemie International Edition

Cover image for Vol. 51 Issue 27

July 2, 2012

Volume 51, Issue 27

Pages 6537–6792

  1. Cover Picture

    1. Top of page
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    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. Flashback
    8. News
    9. Author Profile
    10. News
    11. Obituary
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
    17. Preview
    1. Cover Picture: Silicon Nanowires as Photoelectrodes for Carbon Dioxide Fixation (Angew. Chem. Int. Ed. 27/2012) (page 6537)

      Rui Liu, Guangbi Yuan, Candice L. Joe, Dr. Thomas E. Lightburn, Prof. Dr. Kian L. Tan and Prof. Dr. Dunwei Wang

      Article first published online: 13 JUN 2012 | DOI: 10.1002/anie.201204212

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      Photofixation of CO2 to produce synthetically valuable molecules can be achieved on a photoelectrode based on silicon nanowires. In their Communication on page 6709 ff., K. L. Tan, D. Wang et al. develop a strategy that uses aromatic ketones to receive the photogenerated electrons. The resulting radicals then react with carbon dioxide to afford α-hydroxy acids, which are precursors for the drugs ibuprofen and naproxen. In close resemblance to natural photosynthesis, their strategy gains reaction specificity by avoiding the direct reduction of CO2.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. Flashback
    8. News
    9. Author Profile
    10. News
    11. Obituary
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
    17. Preview
    1. Inside Cover: Watching Water Migration around a Peptide Bond (Angew. Chem. Int. Ed. 27/2012) (page 6538)

      Kohei Tanabe, Dr. Mitsuhiko Miyazaki, Matthias Schmies, Alexander Patzer, Markus Schütz, Prof. Dr. Hiroshi Sekiya, Prof. Dr. Makoto Sakai, Prof. Dr. Otto Dopfer and Prof. Dr. Masaaki Fujii

      Article first published online: 22 JUN 2012 | DOI: 10.1002/anie.201204562

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      The motion of a single water ligand around a peptide bond in acetanilide was probed in real time by time-resolved IR spectroscopy. In their Communication on page 6604 ff., O. Dopfer, M. Fujii et al. observe that triggered by photo-ionization, the H2O ligand is released from the CO site of the peptide linkage and trapped after a migration time of 5 ps at the NH site of the same peptide bond. The migration occurs via an intermediate in which the H2O molecule binds neither to the CO nor the NH site.

  3. Inside Back Cover

    1. Top of page
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    5. Back Cover
    6. Graphical Abstract
    7. Flashback
    8. News
    9. Author Profile
    10. News
    11. Obituary
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
    17. Preview
    1. Inside Back Cover: Reconstitution of the B12 Macrocycle by Radical Ring Closure of a Blue Secocorrin (Angew. Chem. Int. Ed. 27/2012) (page 6793)

      Mag. Markus Ruetz, Dr. Sergey N. Fedosov and Prof. Dr. Bernhard Kräutler

      Article first published online: 13 JUN 2012 | DOI: 10.1002/anie.201204200

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      The reconstitution of the B12 macrocycle by a radical reaction of a blue secocorrinoid, itself a product of B12 degradation, is described by B. Kräutler et al. on page 6780 ff. The epicobalamin obtained is a new type of vitamin B12 derivative, and the first B12 analogue containing the major elements of the B12 structure that is poorly bound by the human B12-binding proteins.

  4. Back Cover

    1. Top of page
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    5. Back Cover
    6. Graphical Abstract
    7. Flashback
    8. News
    9. Author Profile
    10. News
    11. Obituary
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
    17. Preview
    1. Back Cover: Controlled Synthesis of Titanate Nanodisks as Versatile Building Blocks for the Design of Hybrid Nanostructures (Angew. Chem. Int. Ed. 27/2012) (page 6794)

      Cao-Thang Dinh, Yongbeom Seo, Thanh-Dinh Nguyen, Prof. Freddy Kleitz and Prof. Trong-On Do

      Article first published online: 22 JUN 2012 | DOI: 10.1002/anie.201204357

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      Inorganic nanocrystals play a central role in nanoscience and nanotechnology. In their Communication on page 6608 ff., F. Kleitz, T.-O. Do et al. present the bottom-up, non-aqueous synthesis of uniform titanate nanodisks with diameters of 12–35 nm. These nanodisks have been used as building blocks for a variety of hybrid nanostructures, such as titanate-based mesoporous hybrids with high surface areas and tailored porosity, as well as metal-titanate colloidal hybrids exhibiting enhanced catalytic activity.

  5. Graphical Abstract

    1. Top of page
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    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. Flashback
    8. News
    9. Author Profile
    10. News
    11. Obituary
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
    17. Preview
    1. Graphical Abstract: Angew. Chem. Int. Ed. 27/2012 (pages 6541–6555)

      Article first published online: 27 JUN 2012 | DOI: 10.1002/anie.201290050

  6. Flashback

    1. Top of page
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    7. Flashback
    8. News
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    10. News
    11. Obituary
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
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    1. 50 Years Ago... (page 6552)

      Article first published online: 27 JUN 2012 | DOI: 10.1002/anie.201203982

  7. News

    1. Top of page
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    6. Graphical Abstract
    7. Flashback
    8. News
    9. Author Profile
    10. News
    11. Obituary
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
    17. Preview
  8. Author Profile

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. Flashback
    8. News
    9. Author Profile
    10. News
    11. Obituary
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
    17. Preview
    1. V. Gevorgyan (page 6562)

      Article first published online: 13 JUN 2012 | DOI: 10.1002/anie.201201015

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      ”When I was eighteen I wanted to be Bruce Lee, or at least Chuck Norris. My motto is give serendipity a chance! …“ This and more about V. Gevorgyan can be found on page 6562.

  9. News

    1. Top of page
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    6. Graphical Abstract
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    8. News
    9. Author Profile
    10. News
    11. Obituary
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
    17. Preview
  10. Obituary

    1. Top of page
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    8. News
    9. Author Profile
    10. News
    11. Obituary
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
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    1. Robert E. Ireland (19292012) (page 6564)

      James A. Marshall

      Article first published online: 31 MAY 2012 | DOI: 10.1002/anie.201203366

  11. Book Review

    1. Top of page
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    7. Flashback
    8. News
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    10. News
    11. Obituary
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
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    1. Writing Chemistry Patents and Intellectual Property. A Practical Guide. By Francis J. Waller. (page 6565)

      Shankar Manyem and Christine A. Goddard

      Article first published online: 25 MAY 2012 | DOI: 10.1002/anie.201202629

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      John Wiley & Sons, Hoboken, 2011. 256 pp., hardcover, € 69.90.—ISBN 978-0470497401

  12. Highlights

    1. Top of page
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    6. Graphical Abstract
    7. Flashback
    8. News
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    10. News
    11. Obituary
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
    17. Preview
    1. Phosphorus Chemistry

      Multiple-Charged P1-Centered Cations: Perspectives in Synthesis (pages 6566–6568)

      Kai-Oliver Feldmann and Dr. Jan J. Weigand

      Article first published online: 31 MAY 2012 | DOI: 10.1002/anie.201201600

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      Taking center stage: Several new features of the title compounds were recently uncovered. P1-centered cations are employed as reagents for the preparation of unprecedented phosphorus compounds and transition-metal complexes. This represents a remarkable extension of their chemistry, which might make an impact on the field of homogeneous catalysis.

    2. Nanocarbons

      Elements for a Rational Polymer Approach towards Carbon Nanostructures (pages 6569–6571)

      Stephen Schrettl and Prof. Holger Frauenrath

      Article first published online: 25 MAY 2012 | DOI: 10.1002/anie.201201423

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      Growth spurt: A recent series of publications promises to pave the way for a polymer approach towards well-defined carbon nanostructures by combining the stepwise organic synthesis of carbon nanotube (CNT) end caps and their use as templates for CNT growth by Diels–Alder addition of nitroethylene as a masked acetylene derivative.

  13. Minireview

    1. Top of page
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    11. Obituary
    12. Book Review
    13. Highlights
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    15. Review
    16. Communications
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    1. Supramolecular Chemistry

      Self-Assembled Multivalency: Dynamic Ligand Arrays for High-Affinity Binding (pages 6572–6581)

      Anna Barnard and Prof. David K. Smith

      Article first published online: 11 JUN 2012 | DOI: 10.1002/anie.201200076

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      The power of many: The use of self-assembly to create dynamic multivalency (see scheme) is a powerful strategy, with some significant advantages over the use of static multivalent arrays. It mimics processes which occur naturally within cell membranes, and has a wide range of potential applications, both in nanomaterials science and nanomedicine.

  14. Review

    1. Top of page
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    7. Flashback
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    11. Obituary
    12. Book Review
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    15. Review
    16. Communications
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    1. Materials Synthesis

      Biomineralization as an Inspiration for Materials Chemistry (pages 6582–6596)

      Fabio Nudelman and Nico A. J. M. Sommerdijk

      Article first published online: 25 MAY 2012 | DOI: 10.1002/anie.201106715

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      Living organisms build special organic–inorganic hybrid materials such as bones, teeth, and shells that are highly sophisticated in terms of their adaptation to function. Chemists and materials scientists mimic these natural strategies to build biominerals and to tune their properties for biomedical and technical applications.

  15. Communications

    1. Top of page
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    12. Book Review
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    14. Minireview
    15. Review
    16. Communications
    17. Preview
    1. Protein Labeling

      Bioorthogonal Imaging of Aurora Kinase A in Live Cells (pages 6598–6603)

      Dr. Katherine S. Yang, Dr. Ghyslain Budin, Dr. Thomas Reiner, Dr. Claudio Vinegoni and Prof. Ralph Weissleder

      Article first published online: 29 MAY 2012 | DOI: 10.1002/anie.201200994

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      In living color: Aurora kinase A (AKA) was imaged in live cells using a bioorthogonal two-step reaction with a small molecule AKA inhibitor (see scheme) and a fluorescent reporter. The fluorescent molecule was localized to spindle poles and microtubules during metaphase, consistent with the localization of both endogenous and green fluorescent protein tagged AKA. By using this approach, changes in AKA distribution during mitosis were also observed.

    2. Hydrogen Bonds

      Watching Water Migration around a Peptide Bond (pages 6604–6607)

      Kohei Tanabe, Dr. Mitsuhiko Miyazaki, Matthias Schmies, Alexander Patzer, Markus Schütz, Prof. Dr. Hiroshi Sekiya, Prof. Dr. Makoto Sakai, Prof. Dr. Otto Dopfer and Prof. Dr. Masaaki Fujii

      Article first published online: 15 JUN 2012 | DOI: 10.1002/anie.201203296

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      A long and winding road: The motion of a single water ligand around a peptide bond in acetanilide was probed in real time by time-resolved IR spectroscopy. Triggered by photoionization, the H2O ligand is released from the CO site of the peptide linkage and trapped after a migration time of 5 ps at the NH site of the same peptide bond (see picture).

    3. Hybrid Materials

      Controlled Synthesis of Titanate Nanodisks as Versatile Building Blocks for the Design of Hybrid Nanostructures (pages 6608–6612)

      Cao-Thang Dinh, Yongbeom Seo, Thanh-Dinh Nguyen, Prof. Freddy Kleitz and Prof. Trong-On Do

      Article first published online: 25 MAY 2012 | DOI: 10.1002/anie.201202046

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      Building with nanobricks: Uniform titanate nanodisks with a controlled diameter of 12–35 nm were synthesized by a non-aqueous method. These nanodisks were used for the design of various titanate-based mesoporous hybrids with a high specific surface area and tailored porosity. They could also be used as efficient stabilizers for the synthesis of small, uniform metal nanoparticles that exhibit enhanced catalytic activity.

    4. Enantioselective Catalysis

      Copper-Catalyzed Enantioselective Allylic Substitution with Readily Accessible Carbonyl- and Acetal-Containing Vinylboron Reagents (pages 6613–6617)

      Fang Gao, Dr. James L. Carr and Prof. Amir H. Hoveyda

      Article first published online: 25 MAY 2012 | DOI: 10.1002/anie.201202856

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      More with boron: The title reaction was developed to generate quaternary carbon stereogenic centers through the use of commercially available vinylboron reagents (see scheme, MOM=methoxymethyl, NHC=N-heterocyclic carbene, pin=pinacolato). Application of the method to the two isomeric forms of an intermediate in morphine biosynthesis demonstrates its utility.

    5. A Robust, Efficient, and Highly Enantioselective Method for Synthesis of Homopropargyl Amines (pages 6618–6621)

      Erika M. Vieira, Dr. Fredrik Haeffner, Prof. Marc L. Snapper and Prof. Amir H. Hoveyda

      Article first published online: 23 MAY 2012 | DOI: 10.1002/anie.201202694

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      Fast, robust, selective: Copper-catalyzed enantioselective additions of homopropargyl groups to a wide range of aldimines proceed readily and with high enantioselectivity. The catalytic method is scalable and practical, the allenylboron reagent is commercially available, and conversion into amines is inexpensive and high-yielding.

    6. Bioimaging

      Ytterbium-Based Bioprobes for Near-Infrared Two-Photon Scanning Laser Microscopy Imaging (pages 6622–6625)

      Dr. Anthony D'Aléo, Dr. Adrien Bourdolle, Dr. Sophie Brustlein, Dr. Teddy Fauquier, Dr. Alexei Grichine, Dr. Alain Duperray, Dr. Patrice L. Baldeck, Dr. Chantal Andraud, Dr. Sophie Brasselet and Dr. Olivier Maury

      Article first published online: 23 MAY 2012 | DOI: 10.1002/anie.201202212

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      Cleanly separated by two photons: The design and photophysical characterization of a new highly stable macrocyclic ytterbium complex featuring a two-photon antenna ligand is described (see picture). The biphotonic sensitization of the near-infrared ytterbium(III) luminescence and the conception of an unconventional near-infrared biphotonic microscope allow performing in-depth imaging of thick tissues.

    7. Nanomaterials

      Nanoparticulate Iron Oxide Tubes from Microporous Organic Nanotubes as Stable Anode Materials for Lithium Ion Batteries (pages 6626–6630)

      Narae Kang, Dr. Ji Hoon Park, Jaewon Choi, Jaewon Jin, Jiseul Chun, Dr. Il Gu Jung, Jaehong Jeong, Prof. Je-Geun Park, Dr. Sang Moon Lee, Dr. Hae Jin Kim and Prof. Seung Uk Son

      Article first published online: 24 MAY 2012 | DOI: 10.1002/anie.201202244

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      Tubes from tubes: Microporous organic nanotubes were prepared by Sonogashira coupling between tetrakis(4-ethynylphenyl)methane and N,N′-di(4-iodophenyl)-4,4′-bipyridinium dichloride. These nanotubes were used as a template for secondary inorganic materials, namely Fe2O3 nanotubes with a high discharge capacity and excellent stability.

    8. Crystal Engineering

      Uranyl Hybrid Material Derived from In Situ Ligand Synthesis: Formation, Structure, and an Unusual Phase Transformation (pages 6631–6634)

      Dr. Michael B. Andrews and Prof. Christopher L. Cahill

      Article first published online: 24 MAY 2012 | DOI: 10.1002/anie.201202402

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      Phase to phase: The in situ hydrolysis of 4-(bromomethyl)benzoic acid to 4-(hydroxymethyl)benzoic acid (HMBA) in the presence of the uranyl cation has resulted in the novel hybrid material (A)[UO2(HMBA)3] (A=NH4+ or H3O+), which was characterized by X-ray diffraction. On exposure to ethanol the material undergoes a solid-state phase transformation, accompanied by the loss of a ligand and counterion to form [UO2(HMBA)2] (see scheme; O red, C black).

    9. Peptide Amphiphile Self-Assembly

      Remodeling Cross-β Nanotube Surfaces with Peptide/Lipid Chimeras (pages 6635–6638)

      Dr. Rong Ni, Dr. W. Seth Childers, Dr. Kenneth I. Hardcastle, Dr. Anil K. Mehta and Prof. David G. Lynn

      Article first published online: 27 JUN 2012 | DOI: 10.1002/anie.201201173

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      Between the sheets: A unique cross-β-peptide amphiphile assembly positions the acyl chain within the hydrophobic cross-β laminate (see picture; acyl chain: red, peptide: gray, lysine: blue). The atomic-level structure of the self-assembled surface can also be systematically altered, opening the possibility to create a wide range of nanostructured biomaterials.

    10. Porous Aromatic Frameworks

      Lithiated Porous Aromatic Frameworks with Exceptional Gas Storage Capacity (pages 6639–6642)

      Dr. Kristina Konstas, James W. Taylor, Dr. Aaron W. Thornton, Dr. Cara M. Doherty, Wei Xian Lim, Dr. Timothy J. Bastow, Dr. Danielle F. Kennedy, Dr. Colin D. Wood, Dr. Barry J. Cox, Prof. James M. Hill, Dr. Anita J. Hill and Dr. Matthew R. Hill

      Article first published online: 5 JUN 2012 | DOI: 10.1002/anie.201201381

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      A porous treasure: Porous aromatic framework PAF-1 (see picture, blue structure) has been lithiated, giving a reduced framework with an increased gas storage capacity compared to native PAF-1 (by 22, 71, and 320 % for H2, CH4, and CO2, respectively). The reduced framework was examined spectroscopically, and the potential hydrogen storage capacity was calculated.

    11. Self-Assembly

      Self-Organization of Hydrogen-Bonding Naphthalene Chromophores into J-type Nanorings and H-type Nanorods: Impact of Regioisomerism (pages 6643–6647)

      Prof. Dr. Shiki Yagai, Yusaku Goto, Dr. Xu Lin, Prof. Dr. Takashi Karatsu, Prof. Dr. Akihide Kitamura, Dr. Daiki Kuzuhara, Prof. Dr. Hiroko Yamada, Dr. Yoshihiro Kikkawa, Dr. Akinori Saeki and Prof. Dr. Shu Seki

      Article first published online: 24 MAY 2012 | DOI: 10.1002/anie.201201436

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      Regioisomers of self-assembling molecules resulted in the evolution of distinct 0D and 1D nanostructures, namely nanorings and nanorods (see picture). J- and H-type excitonic coupling of naphthalene chromophores was found in the nanostructures. The bulk liquid-crystalline states contain hydrogen-bonded rosettes, which explains how the observed regioisomers generate distinct nanostructures with characteristic excitonic interactions.

    12. Electrochemical Imaging

      Local Redox-Cycling-Based Electrochemical Chip Device with Deep Microwells for Evaluation of Embryoid Bodies (pages 6648–6652)

      Dr. Kosuke Ino, Taku Nishijo, Toshiharu Arai, Yusuke Kanno, Dr. Yasufumi Takahashi, Dr. Hitoshi Shiku and Prof. Dr. Tomokazu Matsue

      Article first published online: 25 MAY 2012 | DOI: 10.1002/anie.201201602

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      Monitoring cellular activity: A local redox-cycling-based electrochemical chip device (see picture) has been used to entrap three-dimensional culture cells and evaluate their activity. Deep microwells were incorporated into the chip device for the trapping of embryoid bodies. This chip device is useful for the evaluation of 3D organ tissues.

    13. Magnetic Properties

      Unconventional Colossal Magnetoresistance in Sodium Chromium Oxide with a Mixed-Valence State (pages 6653–6656)

      Dr. Hiroya Sakurai, Dr. Taras Kolodiazhnyi, Dr. Yuichi Michiue, Dr. Eiji Takayama-Muromachi, Yuichi Tanabe and Prof. Dr. Hikomitsu Kikuchi

      Article first published online: 18 JUN 2012 | DOI: 10.1002/anie.201201884

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      Spin frustration and the unusual electronic state of Cr4+ ions are the origins of unconventional colossal magnetoresistance (CMR) in NaCr2O4, a new member of the rare mixed-valence chromium oxides. CMR materials have previously been limited to almost only manganese oxides; the discovery of the CMR in a non-manganese-based material opens a new dimension in the quest for novel CMR materials.

    14. Heterogeneous Catalysis

      Structural Origin: Water Deactivates Metal Oxides to CO Oxidation and Promotes Low-Temperature CO Oxidation with Metals (pages 6657–6661)

      Hai-Feng Wang, Richard Kavanagh, Prof. Yang-Long Guo, Prof. Yun Guo, Prof. Guan-Zhong Lu and Prof.  P. Hu

      Article first published online: 23 MAY 2012 | DOI: 10.1002/anie.201108981

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      Test the water: Calculations have been used to investigate why water deactivates Co3O4 to CO oxidation and activates platinum group metals in the same reaction. The significant difference in the potential energy surfaces of OH on metal versus metal oxides is the origin of the different effects water has in these systems.

    15. Tunable Luminescence

      Tunable Photoluminescence from Graphene Oxide (pages 6662–6666)

      Chih-Tao Chien, Shao-Sian Li, Wei-Jung Lai, Yun-Chieh Yeh, Hsin-An Chen, I-Shen Chen, Dr. Li-Chyong Chen, Dr. Kuei-Hsien Chen, Dr. Takashi Nemoto, Prof. Seiji Isoda, Prof. Mingwei Chen, Dr. Takeshi Fujita, Dr. Goki Eda, Hisato Yamaguchi, Prof. Manish Chhowalla and Prof. Chun-Wei Chen

      Article first published online: 23 MAY 2012 | DOI: 10.1002/anie.201200474

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      Tuning to G(O) flat: Photoluminescence in graphene oxide (GO) suspensions can be tuned from red to blue emission (see scheme) by gradually changing the amounts of sp2- and sp3-bonded carbon atoms through reduction of the surface oxide groups. Electron–hole recombination from two different types of excited states is proposed to explain the luminescence in GO at varying degrees of reduction.

    16. Solar Cells

      Generation of Alternating Current in Response to Discontinuous Illumination by Photoelectrochemical Cells Based on Photosynthetic Proteins (pages 6667–6671)

      Dr. Swee Ching Tan, Dr. Lucy I. Crouch, Dr. Michael R. Jones and Prof. Mark Welland

      Article first published online: 23 MAY 2012 | DOI: 10.1002/anie.201200466

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      AC or DC? Protein-based photoelectrochemical cells that were constructed using a photosynthetic reaction center (left) generated a conventional direct current (DC) output during continuous illumination but an alternating current (AC) during regular light-on/light-off cycles (right). The mechanism of AC generation exploits the ability of nature's reaction centers to store charge as well as to catalyze highly efficient photochemical charge separation.

    17. Boron Chemistry

      Dynamic Combinatorial Chemistry Employing Boronic Acids/Boronate Esters Leads to Potent Oxygenase Inhibitors (pages 6672–6675)

      Marina Demetriades, Ivanhoe K. H. Leung, Dr. Rasheduzzaman Chowdhury, Mun Chiang Chan, Dr. Michael A. McDonough, Dr. Kar Kheng Yeoh, Dr. Ya-Min Tian, Dr. Timothy D. W. Claridge, Prof. Peter J. Ratcliffe, Dr. Esther C. Y. Woon and Prof. Christopher J. Schofield

      Article first published online: 25 MAY 2012 | DOI: 10.1002/anie.201202000

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      Dynamic duo: The reversible reaction of boronic acids with alcohols to form boronate esters, coupled to protein mass spectrometry analyses, was used to discover potent oxygenase inhibitors. This dynamic combinatorial mass spectrometry technique could potentially be applied to the identification of other protein inhibitors.

    18. Water Splitting

      Development of an O2-Sensitive Fluorescence-Quenching Assay for the Combinatorial Discovery of Electrocatalysts for Water Oxidation (pages 6676–6680)

      Dr. James B. Gerken, Jamie Y. C. Chen, Robert C. Massé, Dr. Adam B. Powell and Prof. Shannon S. Stahl

      Article first published online: 24 MAY 2012 | DOI: 10.1002/anie.201201999

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      Realizing their potential: The title assay has enabled rapid screening of diverse mixed-metal oxide electrocatalysts composed exclusively of earth-abundant metal ions. Several newly discovered catalyst compositions (e.g., Ni/Al/Fe oxides) exhibit substantially lower overpotentials for water oxidation than known, widely used electrocatalysts.

    19. Self-Sorting

      Integrative Self-Sorting Synthesis of a Fe8Pt6L24 Cubic Cage (pages 6681–6685)

      Dr. Maarten M. J. Smulders, Dr. Azucena Jiménez and Dr. Jonathan R. Nitschke

      Article first published online: 5 JUN 2012 | DOI: 10.1002/anie.201202050

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      96 bonds were formed when 62 building blocks (heterotopic ligands with FeII and PtII ions) self-assembled in a one-pot reaction into a heterometallic Fe8Pt6L24 cubic cage (see model, Fe purple, Pt orange, N blue). The dynamic nature of this method also allowed an efficient cage-to-cage conversion: a tetrahedral Fe4L6 cage was converted into the Fe8Pt6L24 cube, which was subsequently converted into a second tetrahedral Fe4L′6 cage.

    20. Enzyme Mechanisms

      Topological Study of Mechanistic Diversity in Conjugated Fatty Acid Biosynthesis (pages 6686–6690)

      Palash Bhar, Darwin W. Reed, Dr. Patrick S. Covello and Prof. Peter H. Buist

      Article first published online: 23 MAY 2012 | DOI: 10.1002/anie.201202080

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      Variations on an oxidative theme: The precision with which FAD2-type desaturases carry out C[BOND]H activation reactions on flexible lipidic substrates is astonishing. The conformational space available within the active site of these enzymes has been explored using deuterium-labeled substrates, and evidence for a novel quasi-eclipsed conformer has been uncovered. The scheme shows some prototypical substrate conformations.

    21. Phenalenyl Radicals

      Chiral Stable Phenalenyl Radical: Synthesis, Electronic-Spin Structure, and Optical Properties of [4]Helicene-Structured Diazaphenalenyl (pages 6691–6695)

      Dr. Akira Ueda, Hideki Wasa, Dr. Shuichi Suzuki, Prof. Dr. Keiji Okada, Prof. Dr. Kazunobu Sato, Prof. Dr. Takeji Takui and Prof. Dr. Yasushi Morita

      Article first published online: 25 MAY 2012 | DOI: 10.1002/anie.201202654

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      A new spin on an old system: The title neutral radicals have been synthesized and characterized for the first time. Thanks to two terminal methoxy groups and three tert-butyl groups, the chiral radicals are configurationally and chemically stable. The three-dimensional π-electron network shows extensive spin delocalization, and the distinct CD properties are attributed to the chirality of the helicene unit (see picture).

    22. Giant Conjugated Macrocycles

      Two Vernier-Templated Routes to a 24-Porphyrin Nanoring (pages 6696–6699)

      Dmitry V. Kondratuk, Dr. Luis M. A. Perdigao, Dr. Melanie C. O'Sullivan, Simon Svatek, Gareth Smith, Dr. James N. O'Shea, Prof. Peter H. Beton and Prof. Harry L. Anderson

      Article first published online: 31 MAY 2012 | DOI: 10.1002/anie.201202870

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      Many hands make light work: Small templates working together have directed the formation of a giant π-conjugated macrocycle with a diameter of 10 nm—larger than many enzymes. The 24 porphyrin subunits of the nanoring are well resolved in the STM image. The conformation of the nanoring can be controlled by self-assembly of a stable 2:24 double-strand sandwich complex with 1,4-diazabicyclo[2.2.2]octane (DABCO).

    23. Homogeneous Catalysis

      A Bifunctional Tungstate Catalyst for Chemical Fixation of CO2 at Atmospheric Pressure (pages 6700–6703)

      Toshihiro Kimura, Dr. Keigo Kamata and Prof. Dr. Noritaka Mizuno

      Article first published online: 5 JUN 2012 | DOI: 10.1002/anie.201203189

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      No pressure: A simple monomeric tungstate, [WO4]2−, serves as a highly efficient homogeneous catalyst for various transformations of CO2 at atmospheric pressure. The tungsten-oxo moiety activates CO2 and the substrate simultaneously. The catalyst system is high yielding and applicable to a wide range of substrates such as amines (see scheme), 2-aminobenzonitriles, and propargylic alcohols.

    24. Synthetic Methods

      Asymmetric Catalytic Alkynylation of Acetaldehyde: Application to the Synthesis of (+)-Tetrahydropyrenophorol (pages 6704–6708)

      Prof. Barry M. Trost and Dr. Adrien Quintard

      Article first published online: 5 JUN 2012 | DOI: 10.1002/anie.201203035

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      In control: By controlling the kinetics of alkynylation over aldolization, the challenging asymmetric catalytic alkynylation of acetaldehyde has been realized. The resulting products are attractive synthons which are produced with good to excellent enantiocontrol, and show broad tolerance and applicability, as demonstrated by the synthesis (+)-tetrahydropyrenophorol.

    25. CO2 Photochemistry

      Silicon Nanowires as Photoelectrodes for Carbon Dioxide Fixation (pages 6709–6712)

      Rui Liu, Guangbi Yuan, Candice L. Joe, Dr. Thomas E. Lightburn, Prof. Dr. Kian L. Tan and Prof. Dr. Dunwei Wang

      Article first published online: 22 MAY 2012 | DOI: 10.1002/anie.201202569

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      Lights on: When illuminated, p-type Si nanowires donate photogenerated electrons to aromatic ketones, producing reactive radicals that can harvest CO2 to yield α-hydroxy acids (see scheme). The reaction scheme closely resembles that of natural photosynthesis and gives up to 98 % yield and selectivity. Products obtained by this reaction include important precursors for nonsteroidal anti-inflammatory drugs, such as ibuprofen and naproxen.

    26. Regioselective Bioamination

      Regio- and Stereoselective Monoamination of Diketones without Protecting Groups (pages 6713–6716)

      Dr. Robert C. Simon, Barbara Grischek, Dr. Ferdinand Zepeck, Dr. Andreas Steinreiber, Prof. Dr. Ferdinand Belaj and Prof. Dr. Wolfgang Kroutil

      Article first published online: 22 MAY 2012 | DOI: 10.1002/anie.201202375

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      Hitting the right target: Differentiation between two keto moieties was accomplished by a regio- and enantioselective bioamination employing ω-transaminases. Using 1,5-diketones as substrates gave access to the optically pure 2,6-disubstituted piperidine scaffold. The approach allowed the shortest synthesis of the alkaloid dihydropinidine, as well as its enantiomer, by choosing an appropriate ω-transaminase.

    27. Biosensors

      Re-engineering Electrochemical Biosensors To Narrow or Extend Their Useful Dynamic Range (pages 6717–6721)

      Di Kang, Dr. Alexis Vallée-Bélisle, Alessandro Porchetta, Prof. Dr. Kevin W. Plaxco and Dr. Francesco Ricci

      Article first published online: 5 JUN 2012 | DOI: 10.1002/anie.201202204

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      By combining DNA probes having different target affinities, but with similar specificity on the same electrode, an extended dynamic response of a biosensor spanning three orders of magnitude in target concentration was obtained. By using a different strategy, the useful dynamic range of an electrochemical DNA sensor was narrowed to only an 8-fold range of target concentrations.

    28. Cascade Reactions

      Rhodium-Catalyzed Cascade Reactions of Dienynes Leading to Substituted Dihydronaphthalenes and Naphthalenes (pages 6722–6727)

      Eri Okazaki, Ryuichi Okamoto, Yu Shibata, Prof. Dr. Keiichi Noguchi and Prof. Dr. Ken Tanaka

      Article first published online: 24 MAY 2012 | DOI: 10.1002/anie.201202125

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      Five in one: Catalytic cascade reactions of dienynes catalyzed by cationic rhodium(I)–binap complexes lead to the formation of 1,2-dihydronaphthalenes, naphthalenes, and 1,4-dihydronaphthalenes. These cascade reactions involve up to five fundamentally different transformations, including the catalytic enantioselective carboformylation of alkenes with aldehydes or the cycloisomerization of enallenes.

    29. Protein–Ligand Interactions

      Assessment of Molecular Interactions through Magnetic Relaxation (pages 6728–6732)

      Oscar J. Santiesteban, Dr. Charalambos Kaittanis and Prof. J. Manuel Perez

      Article first published online: 24 MAY 2012 | DOI: 10.1002/anie.201202077

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      Just relax: The dissociation constants (KD) of various molecular interactions can be determined using a novel competition assay with binding magnetic relaxation nanosensors. In this assay, changes in the magnetic relaxation (MR) of an aqueous suspension of the nanosensors facilitate the fast determination of KD values by using nanomolar protein concentrations (see picture).

    30. Radiochemistry

      Metal-Free Oxidative Fluorination of Phenols with [18F]Fluoride (pages 6733–6737)

      Dr. Zhanghua Gao, Dr. Yee Hwee Lim, Dr. Matthew Tredwell, Dr. Lei Li, Stefan Verhoog, Dr. Matthew Hopkinson, Wojciech Kaluza, Dr. Thomas Lee Collier, Dr. Jan Passchier, Dr. Mickael Huiban and Prof. Véronique Gouverneur

      Article first published online: 25 MAY 2012 | DOI: 10.1002/anie.201201502

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      The radiochemical synthesis of [18F]4-fluorophenols is based on phenol umpolung under oxidative conditions and direct nucleophilic fluorination with [18F]fluoride (see scheme, TBAF=tetra-n-butylammonium fluoride, TFA=trifluoroacetic acid). Readily available O-unprotected 4-tert-butyl phenols are used as precursors in this one-pot protocol. The reaction is completed in less than 30 minutes at room temperature and can be performed using standard or microfluidic technology.

    31. Main Group Chemistry

      Low-Coordinate Germanium(II) Centers Within Distorted Axially Chiral Seven-Membered Chelates: Stereo- and Enantioselective Cycloadditions (pages 6738–6741)

      Dr. Hidekazu Arii, Taiyo Amari, Prof. Dr. Junji Kobayashi, Prof. Dr. Kunio Mochida and Prof. Dr. Takayuki Kawashima

      Article first published online: 5 JUN 2012 | DOI: 10.1002/anie.201201566

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      Distorted germylene: A distorted seven-membered N-heterocyclic germylene, which has a germanium center of relatively high Lewis acidity, reacts with benzaldehyde to give (2+1+1) or (2+2+1) cycloadducts. The type of cycloadduct produced in the reaction is dependent on the ratio of substrates used. It is considered that the reactions involve stereoselective 1,3-dipolar cycloadditions of an in situ generated carbonyl germaylide.

    32. Platinum Drugs

      Combating the Drug Resistance of Cisplatin Using a Platinum Prodrug Based Delivery System (pages 6742–6747)

      Yuanzeng Min, Cheng-Qiong Mao, Siming Chen, Guolin Ma, Prof. Jun Wang and Prof. Yangzhong Liu

      Article first published online: 25 MAY 2012 | DOI: 10.1002/anie.201201562

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      Resistance is futile: A platinum(IV) prodrug conjugated to a gold-nanorod-based delivery agent avoids the type of drug resistance that is associated with cisplatin (see picture). This conjugate is taken up into cells through endocytosis, thus avoiding the resistance-associated uptake mediated by the copper transport protein Ctr1. The platinum(IV) prodrug is more inert than cisplatin to glutathione and metallothionein, which cause deactivation.

    33. Phosphorus Heterocycles

      1H-Phosphindoles as Structural Units in the Synthesis of Chiral Helicenes (pages 6748–6752)

      Keihann Yavari, Dr. Souad Moussa, Prof. Béchir Ben Hassine, Dr. Pascal Retailleau, Dr. Arnaud Voituriez and Dr. Angela Marinetti

      Article first published online: 22 MAY 2012 | DOI: 10.1002/anie.201202024

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      Building helicenes: A photochemical cyclization approach affords helicenes in which the fused ring sequence ends with a phosphole unit (see scheme). The stereogenic phosphorus centers of the substrates control the screw sense of helical chirality. The terminal phosphole units undergo photochemical [2+2] annulations to give dimeric helical structures.

    34. Heterogeneous Catalysis

      Highly Dispersed Surfactant-Free Nickel Nanoparticles and Their Remarkable Catalytic Activity in the Hydrolysis of Ammonia Borane for Hydrogen Generation (pages 6753–6756)

      Pei-Zhou Li, Dr. Arshad Aijaz and Prof. Dr. Qiang Xu

      Article first published online: 24 MAY 2012 | DOI: 10.1002/anie.201202055

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      Highly active: Surfactant-free Ni nanocatalysts were highly dispersed into the nanoporous carbon support MSC-30 through a dry process, and the obtained Ni@MSC-30 catalyzed the generation of H2 from the hydrolysis of ammonia borane at room temperature (see picture). The improvement of the performance of surfactant-free non-noble metal nanocatalysts is a promising step toward the application of NH3BH3 as an applicable chemical hydrogen storage material.

    35. Diyne Metathesis

      Catalytic Metathesis of Conjugated Diynes (pages 6757–6761)

      Dipl.-Chem. Sergej Lysenko, MSc Jeroen Volbeda, Prof. Peter G. Jones and Prof. Dr. Matthias Tamm

      Article first published online: 23 MAY 2012 | DOI: 10.1002/anie.201202101

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      The tungsten benzylidyne complex [PhC[TRIPLE BOND]W{OSi(OtBu)3}3] efficiently catalyzes the metathesis of conjugated diynes and ring-closing diyne metathesis (see scheme). Although this reaction implies C[BOND]C single-bond activation, 13C labeling studies reveal that it proceeds by classical alkylidyne group exchange and involves cleavage and formation of carbon–carbon triple bonds.

    36. Asymmetric Catalysis

      Enantioselective Rhodium-Catalyzed Addition of Potassium Alkenyltrifluoroborates to Cyclic Imines (pages 6762–6766)

      Dr. Yunfei Luo, Dr. Andrew J. Carnell and Dr. Hon Wai Lam

      Article first published online: 25 MAY 2012 | DOI: 10.1002/anie.201202136

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      Fixed: Cyclic imines, in which the C[DOUBLE BOND]N bond is constrained in the Z geometry, have been identified as highly effective substrates for enantioselective rhodium-catalyzed additions of potassium alkenyltrifluoroborates. Not only is the alkene in the products a useful functional handle for subsequent manipulations, products containing aryl sulfamates may be employed in nickel-catalyzed Suzuki–Miyaura and Kumada coupling reactions to generate further compounds of interest.

    37. Biomimetic Synthesis

      An Iron(III) Iodosylbenzene Complex: A Masked Non-Heme FeVO (pages 6767–6770)

      Dr. Anders Lennartson and Prof. Christine J. McKenzie

      Article first published online: 25 MAY 2012 | DOI: 10.1002/anie.201202487

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      Coordinative flexibility and ligand bifunctionality play important roles in a biomimetic iron complex of a hexadentate ligand (see picture). This system can bind an auxiliary iodosylbenzene ligand to give the first structurally characterized metal complex of this important oxidizing agent. The complex is a protected precursor for FeVO species, and the selective high-yielding catalytic oxygenation of a sulfide is demonstrated.

    38. DNA Nanostructures

      Design Strategy for DNA Rotaxanes with a Mechanically Reinforced PX100 Axle (pages 6771–6775)

      Dr. Damian Ackermann, Dr. Stefan-S. Jester and Prof. Michael Famulok

      Article first published online: 31 MAY 2012 | DOI: 10.1002/anie.201202816

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      Non-deformable axles based on paranemic crossover DNAs can serve as components for mechanically stable DNA rotaxanes. The required design strategies provide generally applicable guidelines for the incorporation of mechanically interlocked DNA architectures or even DNA origami structures. DNA rotaxanes with mechanically reinforced axles can serve as precursors for complex molecular machines capable of force transmission.

    39. Experimental Bond Orders

      The Significance of Ionic Bonding in Sulfur Dioxide: Bond Orders from X-ray Diffraction Data (pages 6776–6779)

      Dr. Simon Grabowsky, Prof. Dr. Peter Luger, Dr. Jürgen Buschmann, Dr. Thomas Schneider, Prof. Dr. Tanja Schirmeister, Dr. Alexandre N. Sobolev and Prof. Dylan Jayatilaka

      Article first published online: 29 MAY 2012 | DOI: 10.1002/anie.201200745

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      A novel refinement technique for X-ray diffraction data has been employed to derive S[BOND]O bond orders in sulfur dioxide experimentally. The results show that ionic S[BOND]O bonding dominates over hypervalency.

    40. Vitamin B12

      Reconstitution of the B12 Macrocycle by Radical Ring Closure of a Blue Secocorrin (pages 6780–6784)

      Mag. Markus Ruetz, Dr. Sergey N. Fedosov and Prof. Dr. Bernhard Kräutler

      Article first published online: 14 JUN 2012 | DOI: 10.1002/anie.201202878

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      A radical B12 synthesis: A recently described blue 7,8-secocorrinoid, a degradation product of vitamin B12, has a remarkable structural predisposition for ring closure. Reductive reconstitution of the corrin macrocycle by means of a stereospecific radical reaction leads to a 7-epicobalamin. Human B12-binding proteins bind this vitamin B12 analogue significantly less strongly than natural cobalamins.

    41. Si[BOND]Si Double Bonds

      Reversible Base Coordination to a Disilene (pages 6785–6788)

      Dr. Kinga Leszczyńska, Dipl.-Chem. Kai Abersfelder, Dr. Andreas Mix, Beate Neumann, Dr. Hans-Georg Stammler, Dr. Michael J. Cowley, Prof. Dr. Peter Jutzi and Prof. Dr. David Scheschkewitz

      Article first published online: 25 MAY 2012 | DOI: 10.1002/anie.201202277

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      Si[DOUBLE BOND]Si activation: Reversible formation of a donor–acceptor complex between an N-heterocyclic carbene and a cyclotrisilene with carbon-based substituents shifts the electron density of the double bond and thus induces strong polarization, as shown by the significantly pyramidal tricoordinate silicon atom.

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