Angewandte Chemie International Edition

Cover image for Angewandte Chemie International Edition

June 18, 2012

Volume 51, Issue 25

Pages 6017–6278

  1. Cover Picture

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    6. Graphical Abstract
    7. Corrigenda
    8. News
    9. Author Profile
    10. Obituary
    11. Book Reviews
    12. Highlight
    13. Essay
    14. Minireview
    15. Review
    16. Communications
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    1. Cover Picture: Photoassisted Ti[BOND]O Activation in a Decamethyltitanocene Dihydroxido Complex: Insights into the Elemental Steps of Water Splitting (Angew. Chem. Int. Ed. 25/2012) (page 6017)

      Monty Kessler, Stefanie Schüler, Dr. Dirk Hollmann, Dr. Marcus Klahn, Dr. Torsten Beweries, Dr. Anke Spannenberg, Prof. Dr. Angelika Brückner and Prof. Dr. Uwe Rosenthal

      Article first published online: 24 MAY 2012 | DOI: 10.1002/anie.201203655

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      Splitting water is a tough goal, but it can in principle be performed by titanium compounds. In their Communication on page 6272 ff., U. Rosenthal et al. describe studies on light-induced titanium–oxygen bond activations in a decamethyltitanocene complex. These studies serve as model reactions for water splitting. The picture shows Oceanus and Hyperion, the titans of water and light, discussing this reaction.

  2. Inside Cover

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    1. Inside Cover: A Tetrathiafulvalene-Functionalized Radiaannulene with Multiple Redox States (Angew. Chem. Int. Ed. 25/2012) (page 6018)

      Dr. Kasper Lincke, Anders Floor Frellsen, Dr. Christian Richard Parker, Prof. Dr. Andrew D. Bond, Prof. Dr. Ole Hammerich and Prof. Dr. Mogens Brøndsted Nielsen

      Article first published online: 23 MAY 2012 | DOI: 10.1002/anie.201203660

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      A fused Weitz/Wurster-type redox system has been prepared by fusing a central expanded radiaannulene core with two tetrathiafulvalene units. The system formally gains Hückel aromaticity by either oxidation (6π-dithiolium units) or reduction (14π-octadehydroannulene unit) and can exist in several redox states with characteristic UV/Vis/IR absorptions. More about this system can be found in the Communication by M. Brøndsted Nielsen and co-workers on page 6099 ff.

  3. Inside Back Cover

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    1. Inside Back Cover: Multi-Timescale Conformational Dynamics of the SH3 Domain of CD2-Associated Protein using NMR Spectroscopy and Accelerated Molecular Dynamics (Angew. Chem. Int. Ed. 25/2012) (page 6279)

      Dr. Loïc Salmon, Dr. Levi Pierce, Alexander Grimm, Dr. Jose-Luis Ortega Roldan, Dr. Luca Mollica, Dr. Malene Ringkjøbing Jensen, Prof. Nico van Nuland, Dr. Phineus R. L. Markwick, Prof. J. Andrew McCammon and Dr. Martin Blackledge

      Article first published online: 24 MAY 2012 | DOI: 10.1002/anie.201203658

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      Mapping the protein conformational energy landscape is possible by using a combination of high-resolution nuclear magnetic resonance spectroscopy and accelerated molecular dynamics simulation. In their Communication on page 6103 ff., M. Blackledge and co-workers provide a detailed description of the different conformational sub-states of the interaction site of the SH3C domain of CD2 associated protein that are sampled on nanosecond to millisecond timescales.

  4. Back Cover

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    1. Back Cover: Recent Advances in Azaborine Chemistry (Angew. Chem. Int. Ed. 25/2012) (page 6280)

      Patrick G. Campbell, Dr. Adam J. V. Marwitz and Prof. Dr. Shih-Yuan Liu

      Article first published online: 12 JUN 2012 | DOI: 10.1002/anie.201203752

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      Ouroboros, from the Greek oura meaning tail and boros meaning eating, is a symbol imbued with great meaning across various diciplines and cultures. For example, the vision of a snake devouring its tail led Kekulé to the structure of the quintessential arene benzene almost 150 years ago. In their Review on page 6074 ff., S.-Y. Liu and co-workers summarize recent progress in the development of boron–nitrogen-containing heteroarenes. Cover illustration: Patrick Blower.

  5. Graphical Abstract

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    1. Graphical Abstract: Angew. Chem. Int. Ed. 25/2012 (pages 6021–6035)

      Article first published online: 13 JUN 2012 | DOI: 10.1002/anie.201290046

  6. Corrigenda

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      Corrigendum: Isolation and Total Synthesis of Icumazoles and Noricumazoles—Antifungal Antibiotics and Cation-Channel Blockers from Sorangium cellulosum (page 6035)

      Jenny Barbier, Dr. Rolf Jansen, Dr. Herbert Irschik, Dr. Stefan Benson, Dr. Klaus Gerth, Bettina Böhlendorf, Prof. Dr. Gerhard Höfle, Prof. Dr. Hans Reichenbach, Jens Wegner, Dr. Carsten Zeilinger, Prof. Dr. Andreas Kirschning and Prof. Dr. Rolf Müller

      Article first published online: 13 JUN 2012 | DOI: 10.1002/anie.201201953

      This article corrects:
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  7. News

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  8. Author Profile

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    1. Akio Baba (page 6042)

      Article first published online: 19 MAR 2012 | DOI: 10.1002/anie.201201014

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      “If I could be described as an animal it would be a white bull. My motto is to accept my fate …” This and more about Akio Baba can be found on page 6042.

  9. Obituary

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    1. D. Wayne Goodman (19452012) (pages 6043–6044)

      Charles T. Campbell, John T. Yates Jr. and Hans-Joachim Freund

      Article first published online: 30 MAY 2012 | DOI: 10.1002/anie.201203579

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  10. Book Reviews

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    1. Dendrimers. Towards Catalytic, Material and Biomedical Uses. By Anne-Marie Caminade, Cédric-Olivier Turrin, Régis Laurent, Armelle Ouali, and Beátrice Delavaux-Nicot. (page 6045)

      Mauri Kostiainen

      Article first published online: 26 APR 2012 | DOI: 10.1002/anie.201201578

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      John Wiley & Sons, Hoboken, 2011. 566 pp., hardcover, € 155.00.—ISBN 978-0470748817

    2. Designing Dendrimers. Edited by Sebastiano Campagna, Paula Ceroni and Fausto Puntoriero. (pages 6045–6046)

      David K. Smith

      Article first published online: 23 MAY 2012 | DOI: 10.1002/anie.201201994

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      John Wiley & Sons, Hoboken, 2011. 600 pp., hardcover, € 129.00.—ISBN 978-0470433553

  11. Highlight

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    1. Metal–Organic Frameworks

      Superhydrophobicity in Highly Fluorinated Porous Metal–Organic Frameworks (pages 6048–6050)

      Dr. Christian Serre

      Article first published online: 25 MAY 2012 | DOI: 10.1002/anie.201201440

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      A new job: Highly fluorinated porous MOFs (see picture) that exhibit a superior hydrophobic character can possibly find an application as new superhydrophobic adsorbents in aqueous-phase separation processes.

  12. Essay

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    1. Coordination Chemistry

      At Least 60 Years of Ferrocene: The Discovery and Rediscovery of the Sandwich Complexes (pages 6052–6058)

      Prof. Dr. Helmut Werner

      Article first published online: 9 MAY 2012 | DOI: 10.1002/anie.201201598

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      “Elusion, Confusion” could well be the title of the story of the discovery and re-discovery of the sandwich complexes, best represented by the accidentally found prototype ferrocene. The two most important competitors in this fiercely contested field, E. O. Fischer und G. Wilkinson, were reconciled (even in terms of dancing) only after they were jointly awarded the Nobel Prize. This keen competition in the 1950s contributed decisively to what R. S. Nyholm called the “Renaissance of Inorganic Chemistry”.

  13. Minireview

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    1. Asymmetric Catalysis

      Brønsted Acid Activation Strategy in Transition-Metal Catalyzed Asymmetric Hydrogenation of N-Unprotected Imines, Enamines, and N-Heteroaromatic Compounds (pages 6060–6072)

      Prof. Dr. Zhengkun Yu, Weiwei Jin and Quanbin Jiang

      Article first published online: 10 MAY 2012 | DOI: 10.1002/anie.201200963

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      Protection free: Asymmetric hydrogenation of the title compounds has been realized under transition-metal catalysis by means of Brønsted acid activators (see scheme). Activation of the Lewis-basic substrates by protonation or hydrogen bonding with a Brønsted acid leads to highly enantioselective hydrogenation, thus providing efficient and atom-economical access to the corresponding chiral amines.

  14. Review

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    1. B,N Heteroarenes

      Recent Advances in Azaborine Chemistry (pages 6074–6092)

      Patrick G. Campbell, Dr. Adam J. V. Marwitz and Prof. Dr. Shih-Yuan Liu

      Article first published online: 29 MAY 2012 | DOI: 10.1002/anie.201200063

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      Ring around the boron: The BN/CC isosterism of arenes, which results in azaborine structures, has emerged as a viable strategy to increase the range of compounds relevant to biomedical research and materials science. As a tribute to Dewar's first synthesis of a monocyclic 1,2-azaborine 50 years ago, this review summarizes recent advances in the synthesis and characterization of carbon(C)–boron(B)–nitrogen(N)-containing heteroaromatics.

  15. Communications

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    1. Oligotwistacene

      Synthesis and Structure Characterization of a Stable Nonatwistacene (pages 6094–6098)

      Dr. Jinchong Xiao, Dr. Hieu M. Duong, Dr. Yi Liu, Dr. Wenxiong Shi, Li Ji, Dr. Gang Li, Prof. Dr. Shuzhou Li, Prof. Xue-Wei Liu, Jan Ma, Prof. Fred Wudl and Prof. Dr. Qichun Zhang

      Article first published online: 4 MAY 2012 | DOI: 10.1002/anie.201200949

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      A clean reaction strategy based on thermally eliminating lactam bridges from a soluble acene precursor through a retro-Diels–Alder reaction, led to the synthesis and characterization of a novel, stable, green crystalline 6,8,10,17,19,21-hexaphenyl-1.22,4.5,11.12,15.16-tetrabenzononatwistacene. An analysis of the single crystal structure of the nonatwistacene indicates that this molecule is twisted at an angle of 25.44°.

    2. Annulenes

      A Tetrathiafulvalene-Functionalized Radiaannulene with Multiple Redox States (pages 6099–6102)

      Dr. Kasper Lincke, Anders Floor Frellsen, Dr. Christian Richard Parker, Prof. Dr. Andrew D. Bond, Prof. Dr. Ole Hammerich and Prof. Dr. Mogens Brøndsted Nielsen

      Article first published online: 29 MAY 2012 | DOI: 10.1002/anie.201202324

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      Multiple states: Fusing a central expanded radiaannulene (RA) core with two tetrathiafulvalene (TTF) units furnishes a molecule that can exist in several redox states with characteristic UV/Vis/IR absorptions. The radical cation was found to be of mixed valence (MV) character as reflected by a low-energy intervalence transition.

    3. Protein Dynamics

      You have full text access to this OnlineOpen article
      Multi-Timescale Conformational Dynamics of the SH3 Domain of CD2-Associated Protein using NMR Spectroscopy and Accelerated Molecular Dynamics (pages 6103–6106)

      Dr. Loïc Salmon, Dr. Levi Pierce, Alexander Grimm, Dr. Jose-Luis Ortega Roldan, Dr. Luca Mollica, Dr. Malene Ringkjøbing Jensen, Prof. Nico van Nuland, Dr. Phineus R. L. Markwick, Prof. J. Andrew McCammon and Dr. Martin Blackledge

      Article first published online: 8 MAY 2012 | DOI: 10.1002/anie.201202026

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      An extensive set of experimental NMR residual dipolar couplings (RDCs) has been used to determine the conformational behavior of the SH3 domain of CD2-associated protein. Analytical descriptions of the local dynamics were compared to restraint-free accelerated molecular dynamics simulation, providing a convergent and comprehensive description of conformational fluctuations on picosecond to millisecond timescales.

    4. Coordination Polymers

      An Alkaline Earth I3O0 Porous Coordination Polymer: [Ba2TMA(NO3)(DMF)] (pages 6107–6111)

      Dr. Maw Lin Foo, Dr. Satoshi Horike, Yasutaka Inubushi and Prof. Dr. Susumu Kitagawa

      Article first published online: 8 MAY 2012 | DOI: 10.1002/anie.201202285

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      A CO2 sieve: [Ba2TMA(NO3)(DMF)] (DMF=dimethylformamide, H3TMA=trimesic acid) is a main group, porous I3O0 coordination polymer that is connected in all three dimensions with barium-oxygen-barium bonds, leading to good thermal stability. The one-dimensional channels of this framework are decorated with protruding oxygen atoms and can separate carbon dioxide from methane under kinetic breakthrough conditions at 273 K.

    5. Biomimetic Gels

      Autonomous Intestine-Like Motion of Tubular Self-Oscillating Gel (pages 6112–6116)

      Yusuke Shiraki and Prof. Dr. Ryo Yoshida

      Article first published online: 9 MAY 2012 | DOI: 10.1002/anie.201202028

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      Totally tubular (chemical) wave! A tubular self-oscillating gel has been designed that converts the chemical energy of the Belousov–Zhabotinsky (BZ) reaction into a mechanical swelling–deswelling of the gel (see scheme). It exhibits peristaltic motion, similar to a living worm, with propagation of the chemical wave. In the gel tube, a bubble is autonomously transported by the peristaltic pumping motion.

    6. Polymers

      Fabrication of Large-Area Two-Dimensional Colloidal Crystals (pages 6117–6120)

      Dr. Jian-Tao Zhang, Luling Wang, Daniel N. Lamont, Prof. Sachin S. Velankar and Prof. Sanford A. Asher

      Article first published online: 8 MAY 2012 | DOI: 10.1002/anie.201105439

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      Nanoparticle coating: A suspension of colloidal particles in a water/propanol solution was layered onto a water surface, where the particles self-assembled into ordered two-dimensional hexagonal crystal arrays (>280 cm2) within two minutes. These arrays were transferred from the water surface to other substrates (see picture) and embedded in a chitosan hydrogel for visual detection of the pH value.

    7. Imaging Agents

      Biomimetic Surface Engineering of Lanthanide-Doped Upconversion Nanoparticles as Versatile Bioprobes (pages 6121–6125)

      Dr. Le-Le Li, Dr. Ruobing Zhang, Dr. Leilei Yin, Kezhi Zheng, Prof. Dr. Weiping Qin, Prof. Dr. Paul R. Selvin and Prof. Dr. Yi Lu

      Article first published online: 8 MAY 2012 | DOI: 10.1002/anie.201109156

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      Coat of lipids: Water-dispersible and functionalizable upconverting nanoparticles (UCNPs) for selective imaging of live cancer cells were synthesized. The synthetic approach involves coating the surface of the UCNPs with a monolayer of phospholipids that contain different functional groups (see picture), thus allowing for conjugation of many molecules for applications in fields such as bioinspired nanoassembly, biosensing, and biomedicine.

      Corrected by:

      Corrigendum: Corrigendum: Biomimetic Surface Engineering of Lanthanide-Doped Upconversion Nanoparticles as Versatile Bioprobes

      Vol. 52, Issue 32, 8190, Article first published online: 2 AUG 2013

    8. Microfluidics

      Polydopamine Microfluidic System toward a Two-Dimensional, Gravity-Driven Mixing Device (pages 6126–6130)

      Inseong You, Dr. Sung Min Kang, Sunhee Lee, Young Ook Cho, Prof. Dr. Jin Back Kim, Prof. Dr. Sang Bok Lee, Prof. Dr. Yoon Sung Nam and Prof. Dr. Haeshin Lee

      Article first published online: 4 MAY 2012 | DOI: 10.1002/anie.201200329

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      Given path: A polydopamine-based, pump-free, two-dimensional microfluidic system is energy-efficiently operated by gravity (see picture). The device consists of polydopamine (pD) micro-patterns on nanostructured, superhydrophobic anodized aluminum oxide (AAO) surfaces on which liquid droplets move along the micro-patterned paths of the polydopamine.

    9. Heterogeneous Catalysis

      Hydrogen-Evolution Catalysts Based on Non-Noble Metal Nickel–Molybdenum Nitride Nanosheets (pages 6131–6135)

      Dr. Wei-Fu Chen, Dr. Kotaro Sasaki, Dr. Chao Ma, Dr. Anatoly I. Frenkel, Dr. Nebojsa Marinkovic, Dr. James T. Muckerman, Dr. Yimei Zhu and Dr. Radoslav R. Adzic

      Article first published online: 8 MAY 2012 | DOI: 10.1002/anie.201200699

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      Not noble but effective: A new class of heterogeneous hydrogen-evolving electrocatalysts based on inexpensive components was developed. The carbon-supported nickel–molybdenum nitride (NiMoNx, see picture) catalyst had a nanoscale sheet structure comprising a few layers and an abundance of highly accessible reactive sites.

    10. Amyloid β Peptides

      An Asymmetric Dimer as the Basic Subunit in Alzheimer’s Disease Amyloid β Fibrils (pages 6136–6139)

      Juan Miguel Lopez del Amo, Matthias Schmidt, Uwe Fink, Muralidar Dasari, Marcus Fändrich and Bernd Reif

      Article first published online: 8 MAY 2012 | DOI: 10.1002/anie.201200965

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      Two-faced culprit: Fibrils of recombinantly produced amyloid β peptides (Aβs; residues 1–40) gave well-resolved solid-state NMR spectra. Two sets of resonances corresponding to residues 12–40 and 21–38 of the Aβ primary sequence were observed (see picture). Statistical analysis of electron microscopy data revealed that it was composed of a single Aβ polymorph, thus indicating that this Aβ fibril is composed of an asymmetric dimer.

    11. Fragment-Based Screening

      Discovery of Small Molecules that Bind to K-Ras and Inhibit Sos-Mediated Activation (pages 6140–6143)

      Qi Sun, Dr. Jason P. Burke, Prof. Jason Phan, Michael C. Burns, Prof. Edward T. Olejniczak, Prof. Alex G. Waterson, Prof. Taekyu Lee, Prof. Olivia W. Rossanese and Prof. Stephen W. Fesik

      Article first published online: 8 MAY 2012 | DOI: 10.1002/anie.201201358

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      Looking for fragments: A fragment-based screen using NMR spectroscopy was applied to discover ligands that bind to the GTPase K-Ras and modulate the activity of the nucleotide exchange factor Sos. Structural data on how these fragment-derived hits bind to the guanosine diphosphate–K-Ras complex (see picture) provides a starting point for the future discovery of drugs that target K-Ras activation and signaling.

    12. High-Throughput Screening

      Reaction Discovery by Using a Sandwich Immunoassay (pages 6144–6148)

      Dr. Julia Quinton, Sergii Kolodych, Dr. Manon Chaumonet, Valentina Bevilacqua, Marie-Claire Nevers, Dr. Hervé Volland, Sandra Gabillet, Dr. Pierre Thuéry, Dr. Christophe Créminon and Dr. Frédéric Taran

      Article first published online: 4 MAY 2012 | DOI: 10.1002/anie.201201451

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      Mmm, a reaction sandwich… Using an immunoassay-based technique able to monitor any kind of cross-coupling reaction, a systematic and rapid evaluation of a large panel of random reactions was carried out. This approach led to the discovery of two new copper-promoted reactions: a desulfurization reaction of thioureas leading to isoureas and a cyclization reaction leading to thiazole derivatives from alkynes and N-hydroxy thioureas.

    13. Mesoporous Materials

      Synthesis of Dual-Mesoporous Silica Using Non-Ionic Diblock Copolymer and Cationic Surfactant as Co-Templates (pages 6149–6153)

      Jing Wei, Qin Yue, Zhenkun Sun, Prof. Dr. Yonghui Deng and Prof. Dr. Dongyuan Zhao

      Article first published online: 13 MAY 2012 | DOI: 10.1002/anie.201202232

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      It takes two: Ordered dual-mesoporous silica with two sets of well-configured pores can be synthesized by evaporation-induced step-by-step aggregating assembly in which the non-ionic block copolymer PEO-b-PMMA (red spheres) and the cationic surfactant alkyltrimethyl ammonium bromide (yellow rods) serve as co-templates in an acidic THF/H2O solution containing tetraethyl orthosilicate as the silica source (SiO2 oligomers shown as green balls in the picture).

    14. Nanoclusters

      Isolation of the Magic-Size CdSe Nanoclusters [(CdSe)13(n-octylamine)13] and [(CdSe)13(oleylamine)13] (pages 6154–6157)

      Yuanyuan Wang, Dr. Yi-Hsin Liu, Ying Zhang, Dr. Fudong Wang, Dr. Paul J. Kowalski, Dr. Henry W. Rohrs, Prof. Richard A. Loomis, Prof. Michael L. Gross and Prof. William E. Buhro

      Article first published online: 13 MAY 2012 | DOI: 10.1002/anie.201202380

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      Pure magic: CdSe nanoclusters with a magic size have previously been obtained only as mixtures. Two ligated forms of (CdSe)13 have now been isolated by exfoliation of nanocluster–n-octylamine bilayer aggregates followed by release of [(CdSe)13(n-octylamine)13] or freely soluble [(CdSe)13(oleylamine)13] nanoclusters by ligand exchange.

    15. Photosensitizers

      Targeting the Oncofetal Thomsen–Friedenreich Disaccharide Using Jacalin-PEG Phthalocyanine Gold Nanoparticles for Photodynamic Cancer Therapy (pages 6158–6162)

      Girgis Obaid, Dr. Isabelle Chambrier, Prof. Michael J. Cook and Prof. David A. Russell

      Article first published online: 9 MAY 2012 | DOI: 10.1002/anie.201201468

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      Light-sensitive: Targeted photodynamic therapy is achieved by using gold nanoparticles that are stabilized by a mixed monolayer of a hydrophobic zinc phthalocyanine photosensitizer, which produces cytotoxic singlet oxygen, and a water-soluble thiol-functionalized poly(ethylene glycol) carrying the lectin jacalin, which targets the Thomsen–Friedenreich disaccharide antigen at the surface of cancer cells.

    16. Heterofullerenes

      Fullerene Doping: Preparation of Azafullerene C59NH and Oxafulleroids C59O3 and C60O4 (pages 6163–6166)

      Nana Xin, Huan Huang, Dr. Jianxin Zhang, Zhifei Dai and Prof. Dr. Liangbing Gan

      Article first published online: 9 MAY 2012 | DOI: 10.1002/anie.201202777

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      Breaking the surface: Replacement of a fullerene cage carbon with a nitrogen or oxygen atom is achieved by reactions mediated with fullerene peroxide. Similar procedures have also generated oxafulleroids with oxygen atoms inserted into the cage skeleton. The dioxafullerene C58O2 was selectively generated in the gas phase under MALDI-TOF conditions.

    17. Chelate Ligands

      Bis(silylenyl)- and Bis(germylenyl)-Substituted Ferrocenes: Synthesis, Structure, and Catalytic Applications of Bidentate Silicon(II)–Cobalt Complexes (pages 6167–6171)

      Dipl.-Chem. Wenyuan Wang, Prof. Dr. Shigeyoshi Inoue, Dr. Stephan Enthaler and Prof. Dr. Matthias Driess

      Article first published online: 4 MAY 2012 | DOI: 10.1002/anie.201202175

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      Strong bite: The two respective SiII and GeII centers in ferrocene-containing bis(silylene) and bis(germylene) ligands 1 can serve as excellent σ donors, as shown in the formation of Co complexes 2 (see scheme, Cp=η5-cyclopentadienyl). Unexpectedly, only the bis(silylene)–Co complex 2 is a precatalyst for the [2+2+2] cycloaddition of phenylacetylene and MeCN, possibly because of a stronger coordination of the GeII donor centers to Co.

    18. Stable Carbenes

      A Cyclic Diaminocarbene with a Pyramidalized Nitrogen Atom: A Stable N-Heterocyclic Carbene with Enhanced Electrophilicity (pages 6172–6175)

      Dr. David Martin, Dr. Nicolas Lassauque, Bruno Donnadieu and Prof. Dr. Guy Bertrand

      Article first published online: 8 MAY 2012 | DOI: 10.1002/anie.201202137

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      An anti-Bredt NHC! Placing one of the adjacent nitrogen atoms of an NHC in the bridgehead position of a bicyclic scaffold prevents the donation of its lone pair. Thus, the π-electron-accepting properties of the carbene center are enhanced, while the strong σ-electron-donating properties of classical NHCs are retained.

    19. Hydrogen Bonding

      You have full text access to this OnlineOpen article
      An Unexpected and Significantly Lower Hydrogen-Bond-Donating Capacity of Fluorohydrins Compared to Nonfluorinated Alcohols (pages 6176–6180)

      Dr. Jérôme Graton, Zhong Wang, Anne-Marie Brossard, Daniela Gonçalves Monteiro, Prof. Dr. Jean-Yves Le Questel and Dr. Bruno Linclau

      Article first published online: 10 MAY 2012 | DOI: 10.1002/anie.201202059

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      Rewriting the rules as fluorination does not always increase hydrogen-bond acidity: while the strongly electron-withdrawing fluorine significantly enhances alcohol H-bond acidity in anti-vicinal fluorohydrins, an intramolecular F⋅⋅⋅HO interaction overrules completely the inductive effect. This leads to an overall decrease in alcohol H-bond acidity, compared to the corresponding nonfluorinated alcohol.

    20. Gold Catalysis

      Gold-Catalyzed Cyclization of 1,6-Diyne-4-en-3-ols: Stannyl Transfer from 2-Tributylstannylfuran Through Au/Sn Transmetalation (pages 6181–6186)

      Yifeng Chen, Ming Chen and Prof. Yuanhong Liu

      Article first published online: 9 MAY 2012 | DOI: 10.1002/anie.201201523

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      Gold-tinted: A gold catalyzed cyclization reaction of 1,6-diyne-4-en-3-ols, incorporating an in situ stannyl transfer reaction involving 2-tributylstannylfuran, gives synthetically valuable 2-stannylnaphthalenes (see scheme; DCE=dichloroethane). A gem-diaurated furan complex, was isolated and fully characterized by X-ray crystallographic analysis, and provides strong evidence for a tin to gold transmetalation step.

    21. Homogeneous Catalysis

      Boronic Acid Catalysis as a Mild and Versatile Strategy for Direct Carbo- and Heterocyclizations of Free Allylic Alcohols (pages 6187–6190)

      Hongchao Zheng, Sina Ghanbari, Shinji Nakamura and Prof. Dr. Dennis G. Hall

      Article first published online: 15 MAY 2012 | DOI: 10.1002/anie.201201620

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      BAC to the future: Boronic acid catalysis (BAC) was applied to the direct activation of alcohols leading to the preparation of carbocycles (see scheme), benzofurans, tetrahydrofurans, pyrrolidines, pyrans, piperidines, and various polycyclic compounds. The reactions proceed under mild conditions that circumvent the use of reactive leaving groups like halides.

    22. Heterogeneous Catalysis

      A Noble-Metal-Free Catalyst Derived from Ni-Al Hydrotalcite for Hydrogen Generation from N2H4⋅H2O Decomposition (pages 6191–6194)

      Lei He, Dr. Yanqiang Huang, Dr. Aiqin Wang, Dr. Xiaodong Wang, Dr. Xiaowei Chen, Dr. Juan José Delgado and Prof. Tao Zhang

      Article first published online: 8 MAY 2012 | DOI: 10.1002/anie.201201737

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      Free of nobility: A supported nickel catalyst derived from Ni-Al hydrotalcite is a promising candidate to replace noble metals for hydrogen generation from the catalytic decomposition of N2H4⋅H2O under ambient conditions. The catalyst produces H2 at 30 °C in 93 % selectivity. The catalytic function is due to the cooperation of highly dispersed Ni nanoparticles and strong basic sites located nearby.

    23. Biomimetic Model

      Oxidative Carbon[BOND]Carbon Bond Cleavage of a α-Hydroxy Ketone by a Functional Model of 2,4′-Dihydroxyacetophenone Dioxygenase (pages 6195–6199)

      Sayantan Paria, Partha Halder and Dr. Tapan Kanti Paine

      Article first published online: 9 MAY 2012 | DOI: 10.1002/anie.201201825

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      Bond cleavage: An iron(II)–α-hydroxy ketone complex of a facial tridentate nitrogen donor ligand undergoes a C[BOND]C bond cleavage reaction in the presence of dioxygen to form two equivalents of carboxylic acids. This reaction is a functional model of 2,4′-dihydroxyacetophenone dioxygenase.

    24. Organocatalysis

      Bifunctional Cinchona Alkaloid/Thiourea Catalyzes Direct and Enantioselective Vinylogous Michael Addition of 3-Alkylidene Oxindoles to Nitroolefins (pages 6200–6204)

      Dr. Claudio Curti, Dr. Gloria Rassu, Dr. Vincenzo Zambrano, Dr. Luigi Pinna, Prof. Dr. Giorgio Pelosi, Dr. Andrea Sartori, Dr. Lucia Battistini, Prof. Dr. Franca Zanardi and Prof. Dr. Giovanni Casiraghi

      Article first published online: 8 MAY 2012 | DOI: 10.1002/anie.201202027

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      Vinylogy: Advances in asymmetric catalysis using the bifunctional cinchona alkaloid/thioureas enabled an umpolung of the classical Cβ reactivity of 3-alkylidene oxindoles, thus allowing the development of the first and sole example of a direct, organocatalytic asymmetric vinylogous Michael (AVM) reaction with nitroolefins.

    25. Nanostructures

      A Nanosheet-Structured Three-Dimensional Macroporous Material with High Ionic Conductivity Synthesized Using Glucose as a Transforming Template (pages 6205–6208)

      Dr. Junjie Ge, Hanping Ding and Prof. Xingjian Xue

      Article first published online: 4 MAY 2012 | DOI: 10.1002/anie.201107838

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      Building with sugar: Glucose acts as a transforming template for the synthesis of the three-dimensional macroporous oxide Sm0.2Ce0.8O1.9. The material has a two-dimensional nanosheet microstructure and has a high surface area and great potential for the fabrication of gas-tight membranes with high ionic conductivity.

    26. Homogeneous Catalysis

      Synthesis of Eight-Membered Lactones: Intermolecular [6+2] Cyclization of Amphoteric Molecules with Siloxy Alkynes (pages 6209–6213)

      Wanxiang Zhao, Zhaobin Wang and Prof. Dr. Jianwei Sun

      Article first published online: 15 MAY 2012 | DOI: 10.1002/anie.201200513

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      That's about the size of it: The title molecules react with siloxy alkynes in the presence of a Brønsted acid to deliver medium-sized lactones through a [6+2] cyclization (see scheme; TIPS=triisopropylsilyl). This process is the first intermolecular synthesis of such lactones and involves a sequence of several selective ring-opening/ring-closing events.

    27. Synthetic Methods

      Chromium(0)-Catalyzed Tandem Cyclization of α,β-Unsaturated Thioimidates Containing an Enyne Moiety (pages 6214–6218)

      Yusuke Karibe, Dr. Hiroyuki Kusama and Prof. Dr. Nobuharu Iwasawa

      Article first published online: 8 MAY 2012 | DOI: 10.1002/anie.201201505

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      Bicyclic: The diastereoselective synthesis of functionalized 1-azabicyclo[5.3.0]decane derivatives proceeds through 1,7-electrocyclization of the zwitterionic intermediates that are formed in the cyclization of α,β-unsaturated thioimidates containing an enyne moiety (see scheme). Furthermore 1,4-addition of nucleophiles to α,β-unsaturated carbene complex intermediates was also achieved.

    28. Dearomatization Reaction

      Dearomatization of Fused Arenes Using Platinum-Catalyzed Intramolecular Formation of Two C[BOND]C Bonds (pages 6219–6222)

      Tetsuro Shibuya, Prof. Dr. Keiichi Noguchi and Prof. Dr. Ken Tanaka

      Article first published online: 8 MAY 2012 | DOI: 10.1002/anie.201202165

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      The (de)aroma of success: A cationic platinum(II) complex generated in situ catalyzes dearomatization of fused arenes by forming two intramolecular C[BOND]C bonds (see scheme). Mechanistic studies reveal that this reaction could proceed through alkyne activation by the cationic platinum(II) complex followed by a Friedel–Crafts-type reaction.

    29. Photocatalysis

      Active Facets on Titanium(III)-Doped TiO2: An Effective Strategy to Improve the Visible-Light Photocatalytic Activity (pages 6223–6226)

      Fan Zuo, Dr. Krassimir Bozhilov, Robert J. Dillon, Le Wang, Phillip Smith, Xiang Zhao, Prof. Christopher Bardeen and Prof. Pingyun Feng

      Article first published online: 4 MAY 2012 | DOI: 10.1002/anie.201202191

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      Partially reduced TiO2 with highly active facets has been fabricated: Ti3+ was successfully incorporated without any additional reducing agent and surfactant, and highly active facets developed preferentially. The product shows improved photocatalytic activity in H2 production over previously reported material. Photocatalytic activity over an extended time period demonstrates the stability of reduced TiO2 made by this approach.

    30. Fluorine Chemistry

      A Facile Parallel Synthesis of Trifluoroethyl-Substituted Alkynes (pages 6227–6230)

      Cui-Bo Liu, Wei Meng, Feng Li, Shuai Wang, Jing Nie and Prof. Jun-An Ma

      Article first published online: 8 MAY 2012 | DOI: 10.1002/anie.201202372

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      Trifluoroethylation made easy: The ease of execution of the reaction (see scheme), which runs under mild conditions and without the need for additional base or ligands, allows for the rapid parallel synthesis of a broad variety of trifluoroethylated alkynes. Both experimental and theoretical analyses indicate that the trifluoromethylcarbene could undergo concerted insertion into the Csp[BOND]H bond of the alkyne.

    31. Organocatalysis

      Nucleophilic Reactivities of Deoxy Breslow Intermediates: How Does Aromaticity Affect the Catalytic Activities of N-Heterocyclic Carbenes? (pages 6231–6235)

      M. Sc. Biplab Maji, Dr. Markus Horn and Prof. Dr. Herbert Mayr

      Article first published online: 9 MAY 2012 | DOI: 10.1002/anie.201202327

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      Aromatic or nonaromatic? Kinetic investigations show that structurally analogous saturated and unsaturated N-heterocyclic carbenes have almost identical nucleophilic reactivities, while the corresponding deoxy Breslow intermediates differ dramatically.

    32. Hydrogen Bonds

      Low-Frequency Vibrational Modes of Protic Molten Salts and Ionic Liquids: Detecting and Quantifying Hydrogen Bonds (pages 6236–6240)

      Dr. Koichi Fumino, Dr. Elena Reichert, Dipl.-Chem. Kai Wittler, Prof. Dr. Rolf Hempelmann and Prof. Dr. Ralf Ludwig

      Article first published online: 4 MAY 2012 | DOI: 10.1002/anie.201200508

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      The subtle balance between Coulomb forces, hydrogen bonds, and dispersion forces is important for the understanding of the unique properties of molten salts and ionic liquids. Vibrational modes with peak frequencies falling in the 140–180 cm−1 range of far-infrared spectra were assigned unequivocally to hydrogen bonds, which are local and directional in nature, but almost insensitive to the molecular weight of the ions.

    33. Phosphorus Azides

      Low-Temperature Isolation of An Azidophosphenium Cation (pages 6241–6245)

      Christian Hering, Prof. Dr. Axel Schulz and Dr. Alexander Villinger

      Article first published online: 4 MAY 2012 | DOI: 10.1002/anie.201201851

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      Trapped in the cold: The synthesis and structural characterization of a GaCl4 salt bearing an azidophosphenium cation is presented for the first time. This formal phosphapentacenium ion with a planar molecular skeleton is only stable at temperatures below −30 °C.

    34. Heterogeneous Catalysis

      The Intimate Relationship between Bulk Electronic Conductivity and Selectivity in the Catalytic Oxidation of n-Butane (pages 6246–6250)

      Dr. Maik Eichelbaum, Dr. Michael Hävecker, Christian Heine, Dr. Andrey Karpov, Cornelia-Katharina Dobner, Dr. Frank Rosowski, Dr. Annette Trunschke and Prof. Dr. Robert Schlögl

      Article first published online: 8 MAY 2012 | DOI: 10.1002/anie.201201866

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      Don't touch! Without electrode contacts, but contact-free with microwaves in a resonant cavity the electronic conductivity of a VPO powder catalyst could be measured under the reaction conditions of the selective oxidation of n-butane to maleic anhydride. As a result, a linear correlation between conductivity and formation rate of maleic anhydride was observed.

    35. Liquid Chromatography

      A Molecular Dynamics Study on the Partitioning Mechanism in Hydrophilic Interaction Chromatography (pages 6251–6254)

      Dr. Sergey M. Melnikov, Dr. Alexandra Höltzel, Prof. Dr. Andreas Seidel-Morgenstern and Prof. Dr. Ulrich Tallarek

      Article first published online: 8 MAY 2012 | DOI: 10.1002/anie.201201096

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      The retention mechanism in hydrophilic interaction chromatography is supposed to involve partitioning of analytes between a mostly organic mobile phase and a water layer at the surface of the stationary phase. By molecular dynamics simulations, in which a 9 nm diameter bare silica pore is fed with H2O/CH3CN mixtures (see picture: 10:90 (v/v)), the water layer is elucidated and interpreted regarding the retention of hydrophilic analytes.

    36. Borosulfates

      The First Borosulfate K5[B(SO4)4] (pages 6255–6257)

      Prof. Dr. Henning A. Höppe, Dr. Karolina Kazmierczak, Michael Daub, Katharina Förg, Franziska Fuchs and Prof. Dr. Harald Hillebrecht

      Article first published online: 8 MAY 2012 | DOI: 10.1002/anie.201109237

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      The first of its kind: K5[B(SO4)4], the first example of a borosulfate, comprises non-condensed [B(SO4)4]5− anions in which the boron atoms are tetrahedrally coordinated to sulfate tetrahedra (see picture; B brown, O red, S yellow). The compound, which crystallizes in a polar space group, was investigated by X-ray diffraction, vibrational spectroscopy, and calculations.

    37. Neutrophil Elastase

      Spatially Resolved Monitoring of Neutrophil Elastase Activity with Ratiometric Fluorescent Reporters (pages 6258–6261)

      Stefanie Gehrig, Prof. Dr. Marcus A. Mall and Priv.-Doz. Dr. Carsten Schultz

      Article first published online: 3 MAY 2012 | DOI: 10.1002/anie.201109226

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      Finding NEmo: In a mouse model for lung inflammation, the lipidated peptide-based ratiometric fluorescent reporter NEmo-2 indicates that neutrophil elastase (NE) activity is mainly associated with the surface of neutrophils (see scheme), whereas a soluble reporter variant showed no activity in the lung fluid, likely because of the abundance of antiproteases. Targeting the localization of NE activity has great potential for the development of improved antiinflammatory drugs.

    38. Spin Crossover

      Electron-Induced Spin Crossover of Single Molecules in a Bilayer on Gold (pages 6262–6266)

      Dr. Thiruvancheril G. Gopakumar, Dr. Francesca Matino, Holger Naggert, Dr. Alexander Bannwarth, Prof. Dr. Felix Tuczek and Prof. Dr. Richard Berndt

      Article first published online: 8 MAY 2012 | DOI: 10.1002/anie.201201203

      Thumbnail image of graphical abstract

      Single molecules of the iron(II) complex [Fe(bpz)2phen] (phen=1,10-phenanthroline, bpz=dihydrobis(pyrazolyl)borate) are reversibly switched between low spin and high spin by electron-induced spin crossover (ELIESST) in a bilayer on gold, as revealed by STM.

      Corrected by:

      Corrigendum: Corrigendum: Electron-Induced Spin Crossover of Single Molecules in a Bilayer on Gold

      Vol. 52, Issue 14, 3796, Article first published online: 26 MAR 2013

    39. sp2–sp3 Diboranes

      Phosphine Adducts of 1,2-Dibromo-1,2-dimesityldiborane(4): Between Bridging Halides and Rearrangement Processes (pages 6267–6271)

      Prof. Dr. Holger Braunschweig, Dipl.-Chem. Alexander Damme, Dr. Jose O. C. Jimenez-Halla, Dr. Thomas Kupfer and Dr. Krzysztof Radacki

      Article first published online: 10 MAY 2012 | DOI: 10.1002/anie.201201673

      Thumbnail image of graphical abstract

      To bridge or not to bridge depends on the size of the Lewis base in mixed sp2–sp3 phosphine adducts of Br2B2Mes2. Whereas reaction with bulky PMeCy2 induced a 1,2-rearrangement to afford the 1,1-dimesityl adduct as the major component, the “normal” 1,2-dimesityl adduct was favored for the smaller PEt3 molecule. The latter contains an uncommon B[BOND]Br[BOND]B bridge and a rare dative B[BOND]Hal bonding interaction to the sp2 boron center.

    40. Water Splitting

      Photoassisted Ti[BOND]O Activation in a Decamethyltitanocene Dihydroxido Complex: Insights into the Elemental Steps of Water Splitting (pages 6272–6275)

      Monty Kessler, Stefanie Schüler, Dr. Dirk Hollmann, Dr. Marcus Klahn, Dr. Torsten Beweries, Dr. Anke Spannenberg, Prof. Dr. Angelika Brückner and Prof. Dr. Uwe Rosenthal

      Article first published online: 8 MAY 2012 | DOI: 10.1002/anie.201202097

      Thumbnail image of graphical abstract

      Step by step: Irradiation of the decamethyltitanocene(IV) dihydroxido complex [Cp*2Ti(OH)2] (Cp*=η5-C5Me5) induces dissociation of Cp* and a rare homolytic Ti[BOND]O bond cleavage, most likely by elimination of an OH radical. Two independent reaction pathways are present, yielding the mononuclear TiIII monohydroxy complex [Cp*2Ti(OH)] as well as two tetranuclear TiIV complexes.

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      Preview: Angew. Chem. Int. Ed. 26/2012 (page 6278)

      Article first published online: 13 JUN 2012 | DOI: 10.1002/anie.201290047

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