Chemistry - A European Journal

Cover image for Vol. 22 Issue 19

Early View (Online Version of Record published before inclusion in an issue)

Editor: Neville Compton, Deputy Editors: Anne Deveson, Elisabeth Roedern

Impact Factor: 5.731

ISI Journal Citation Reports © Ranking: 2014: 22/157 (Chemistry Multidisciplinary)

Online ISSN: 1521-3765

Associated Title(s): Angewandte Chemie International Edition, Chemistry – An Asian Journal, ChemistryOpen, ChemistrySelect, ChemBioChem, ChemCatChem, ChemElectroChem, ChemMedChem, ChemPhysChem, ChemPlusChem, ChemSusChem, European Journal of Inorganic Chemistry, European Journal of Organic Chemistry

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  2. 101 - 195
  1. Full Papers

    1. Sensors

      Monolayer Co3O4 Inverse Opals as Multifunctional Sensors for Volatile Organic Compounds

      Chul-Soon Lee, Zhengfei Dai, Seong-Yong Jeong, Chang-Hoon Kwak, Bo-Young Kim, Do Hong Kim, Prof. Ho Won Jang, Joon-Shik Park and Prof. Jong-Heun Lee

      Article first published online: 29 APR 2016 | DOI: 10.1002/chem.201505210

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      Multi-gas sensor: Co3O4 inverse opal (IO) thin films for gas sensing (see figure) were prepared by template synthesis. Unprecedentedly high ethanol response and temperature-modulated selective detection of ethanol, xylene, and methyl benzenes were attributed to the highly chemiresistive IO nanoarchitecture and to the tuned catalytic promotion of different gas-sensing reactions, respectively.

  2. Minireviews

    1. Palladium Complexes

      Understanding Palladium Acetate from a User Perspective

      William A. Carole and Dr. Thomas J. Colacot

      Article first published online: 29 APR 2016 | DOI: 10.1002/chem.201601450

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      Palladium acetate, a user perspective! This minireview provides a concise update on the synthesis, structure, and purity determination of palladium acetate from a user perspective from both academia and industry. Also discussed are the reported activation pathways for pure palladium acetate and the impact of its common impurities in organic synthesis.

  3. Communications

    1. Nanostructures

      Hierarchically Self-Assembled Star-Shaped ZnO Microparticles for Electrochemical Sensing of Amines

      Prof. Dr. Jianping Du, Xiaoxi Huang, Dr. Ruihua Zhao, Prof. Jinping Li and Prof. Dr. Tewodros Asefa

      Article first published online: 29 APR 2016 | DOI: 10.1002/chem.201601110

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      Stellar detection: Hierarchically nanostructured star-shaped ZnO (SSZ) microparticles that can serve as efficient electrochemical sensors for ethylenediamine (EDA) are synthesized by a simple hydrothermal synthetic route. The SSZ microparticles show a high sensitivity for detection of EDA with a value of 2.98×10−2 mA cm−2 mm−1 and with a short response time of 8 s.

    2. Synthetic Methods

      Cross-Electrophile Coupling of Vinyl Halides with Alkyl Halides

      Keywan A. Johnson, Dr. Soumik Biswas and Prof. Daniel J. Weix

      Article first published online: 28 APR 2016 | DOI: 10.1002/chem.201601320

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      Win/Win! An improved method for the coupling of aryl and vinyl bromides with alkyl halides that gave high yields for a variety of substrates while lowering the catalyst loading and temperature of the reactions is presented. Alkenyl bromides gave the desired olefins with near complete stereoretention. Reactions can be run with as low as 0.5 mol % catalyst loading or reactions with a higher loading finish in as little as 20 minutes (see scheme).

  4. Full Papers

    1. Nanotubes

      Effect of Photoinduced Size Changes on Protein Refolding and Transport Abilities of Soft Nanotubes

      Dr. Naohiro Kameta, Dr. Haruhisa Akiyama, Dr. Mitsutoshi Masuda and Dr. Toshimi Shimizu

      Article first published online: 28 APR 2016 | DOI: 10.1002/chem.201504613

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      Denatured proteins have been encapsulated in the nanochannels of soft nanotubes produced by self-assembly of azobenzene-modified amphiphiles in water. Photoinduced trans-to-cis photoisomerization of the azobenzene units of the amphiphiles packed in the solid bilayer membrane resulted in narrowing of the nanochannels, which in turn led to rapid squeezing out of the encapsulated proteins into the bulk solution and simultaneous refolding of the proteins (see figure; i.d.=internal diameter).

  5. Communications

    1. Energy Transfer

      Employing Core-Shell Quantum Dots as Triplet Sensitizers for Photon Upconversion

      Keisuke Okumura, Kazuma Mase, Dr. Nobuhiro Yanai and Prof. Dr. Nobuo Kimizuka

      Article first published online: 28 APR 2016 | DOI: 10.1002/chem.201600998

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      Heroes in a core-shell: CdSe/ZnS core-shell quantum dots (QDs) can work as triplet sensitizers for photon upconversion (UC). Higher UC quantum yield was achieved by using the core-shell QDs compared with core-only CdSe QDs, thanks to the passivation of non-radiative surface recombination sites by the shell layer with wider bandgap.

  6. Full Papers

    1. Ion-Pairing Assemblies

      Ion-Pairing Assemblies Based on Pentacyano-Substituted Cyclopentadienide as a π-Electronic Anion

      Dr. Yuya Bando, Dr. Yohei Haketa, Dr. Tsuneaki Sakurai, Dr. Wakana Matsuda, Prof. Shu Seki, Prof. Hikaru Takaya and Prof. Hiromitsu Maeda

      Article first published online: 27 APR 2016 | DOI: 10.1002/chem.201600686

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      Taking charge: Ion-pairing assemblies of pentacyanocyclopentadienide (PCCp), a stable π-electronic anion, were constructed in combination with various cations. PCCp-based assemblies exist as single crystals and mesophases owing to interionic interactions with π-electronic and aliphatic cations with a variety of geometries, substituents, and electronic structures (see figure).

    2. Structure–Activity Relationships | Hot Paper

      Anisotropic Dissociation of π–π Stacking and Flipping-Motion-Induced Crystal Jumping in Alkylacridones and Their Dicyanomethylene Derivatives

      Dr. Takashi Takeda and Prof. Tomoyuki Akutagawa

      Article first published online: 27 APR 2016 | DOI: 10.1002/chem.201600794

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      Jump around! A systematic investigation into crystal-jumping behavior was achieved through chemical modification of acridones. Anisotropic dissociation of π stacking in a dimer was important for inducing crystal jumping in ethylacridone, whereas the collective fluctuation/flipping motion of a dicyanomethylene unit induced crystal jumping in dicyanomethylenated acridones (see figure).

  7. Communications

    1. Organic Chemistry

      Rhodium-Catalyzed Enantioselective Arylation of Aliphatic Imines

      Naoya Kato, Tomohiko Shirai and Prof. Dr. Yasunori Yamamoto

      Article first published online: 27 APR 2016 | DOI: 10.1002/chem.201601246

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      Chiral rhodium(I)/N-Me-BIPAM-catalyzed highly enantioselective arylation of aliphatic N-sulfonyl aldimines with arylboronic acids gave the optically active α-branched amines (up to 99 % ee). In addition, this asymmetric arylation achieved efficient synthesis of (+)-NPS R-568 and Cinacalcet which are calcimimetic agents.

    2. Coupling Reaction | Hot Paper

      Palladium-Catalyzed Construction of Amidines from Arylboronic Acids under Oxidative Conditions

      Fengxiang Zhu, Yahui Li, Zechao Wang, Prof. Dr. Romano V. A. Orru, Prof. Dr. Bert U. W. Maes and Prof. Dr. Xiao-Feng Wu

      Article first published online: 27 APR 2016 | DOI: 10.1002/chem.201601262

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      A valuable palladium-catalyzed three-component coupling reaction for the synthesis of amidines has been developed. Using arylboronic acids, isocyanides, and anilines as the reactants under oxidative conditions, various amidines were isolated in good yields with good functional group tolerances (see scheme).

  8. Full Papers

    1. Aromaticity | Hot Paper

      You have free access to this content
      Hückel's Rule of Aromaticity Categorizes Aromatic closo Boron Hydride Clusters

      Dr. Jordi Poater, Prof. Dr. Miquel Solà, Prof. Dr. Clara Viñas and Prof. Dr. Francesc Teixidor

      Article first published online: 27 APR 2016 | DOI: 10.1002/chem.201600510

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      The incredible Hückel: Aromatic closo boron hydride clusters can be categorized into different series, according to the n value of the Hückel (4 n+2) π rule. This classification arises from a link between the two-dimensional Hückel rule, followed by aromatic [n]annulenes, and Wade–Mingos’ rule of three-dimensional aromaticity, applied to the aromatic [BnHn]2− closo boron hydride clusters.

    2. Quantum Chemistry

      Tuning the Protein-Induced Absorption Shifts of Retinal in Engineered Rhodopsin Mimics

      Carl-Mikael Suomivuori, Lucas Lang, Prof. Dr. Dage Sundholm, Dr. Ana P. Gamiz-Hernandez and Prof. Dr. Ville R. I. Kaila

      Article first published online: 27 APR 2016 | DOI: 10.1002/chem.201505126

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      Color tuning: The light-capturing properties of engineered rhodopsin mimics are studied using large-scale correlated quantum chemical calculations. The calculations show that these proteins absorb across a large part of the visible spectrum by combined polarization and electrostatic effects.

    3. Vitamin Substituent Effects

      Vitamin B12 Phosphate Conjugation and Its Effect on Binding to the Human B12-Binding Proteins Intrinsic Factor and Haptocorrin

      Keith Ó Proinsias, Michał Ociepa, Katarzyna Pluta, Mikołaj Chromiński, Prof. Ebba Nexo and Prof. Dorota Gryko

      Article first published online: 27 APR 2016 | DOI: 10.1002/chem.201504898

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      Vitamins to deliver: The first vitamin B12 derivatives modified at the phosphate moiety have been reported. A series of functionalized derivatives have been synthesized, some of which were used in CuAAC reactions and examined as possible photocleavable delivery vehicles (see scheme). Selected compounds were tested for their binding ability towards haptocorrin and intrinsic factor.

  9. Communications

    1. Phthalocyanines

      Pyrene-Bridged Boron Subphthalocyanine Dimers: Combination of Planar and Bowl-Shaped π-Conjugated Systems for Creating Uniquely Curved π-Conjugated Systems

      Shota Nakano, Yuto Kage, Prof. Hiroyuki Furuta, Prof. Nagao Kobayashi and Prof. Soji Shimizu

      Article first published online: 27 APR 2016 | DOI: 10.1002/chem.201600548

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      Pyrene-bridged boron subphthalocyanine (SubPc) dimers were synthesized from a mixed-condensation reaction of tetracyanopyrene and tetrafluorophthalonitrile, and their syn and anti isomers were successfully separated. In addition to the redshift of the Q band absorption, combining the curved π-conjugation of SubPc with the planar π-conjugation of pyrene enabled facile embracement of C60 molecules, owing to the enhanced concave–convex π–π stacking interactions.

  10. Full Papers

    1. Quantum Dots

      Chemical Functionalisation and Photoluminescence of Graphene Quantum Dots

      Prof. Dr. Ryo Sekiya, Yuichiro Uemura, Prof. Dr. Hiroyoshi Naito, Prof. Dr. Kensuke Naka and Prof. Dr. Takeharu Haino

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201504963

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      On edge: Three types of functionalised graphene quantum dots (GQDs) were synthesised by the CuI-catalysed Huisgen cycloaddition reaction of an edge-modified GQD with organic azides (see scheme). These functionalised GQDs displayed white-light-emission upon excitation at 360 nm. Size-exclusion chromatography demonstrated that the white-light emission originated from the coexistence of differently sized GQDs that emit at different photoluminescence wavelengths.

    2. Fullerenes

      Singly Bonded Monoadduct rather than Methanofullerene: Manipulating the Addition Pattern of Trimetallic Nitride Clusterfullerene through One Endohedral Metal Atom Substitution

      Song Wang, Dr. Jing Huang, Congli Gao, Fei Jin, Prof. Dr. Qunxiang Li, Prof. Dr. Suyuan Xie and Prof. Dr. Shangfeng Yang

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201600388

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      Functionalized fullerenes: The first singly bonded Bingel–Hirsch derivative of trimetallic nitride clusterfullerene (NCF) is synthesized through a Bingel–Hirsch reaction of TiY2N@Ih-C80 and diethyl bromomalonate, and its structure is unambiguously determined. Upon substituting one endohedral yttrium (Y) atom of Y3N@Ih-C80 with titanium (Ti), the Bingel–Hirsch derivative changes from the cyclopropane to the singly bonded monoadduct.

  11. Communications

    1. Metal–Organic Frameworks

      Intercalation of Coordinatively Unsaturated FeIII Ion within Interpenetrated Metal–Organic Framework MOF-5

      Rebecca J. Holmberg, Thomas Burns, Samuel M. Greer, Dr. Libor Kobera, Dr. Sebastian A. Stoian, Dr. Ilia Korobkov, Prof. Stephen Hill, Prof. David L. Bryce, Prof. Tom K. Woo and Prof. Muralee Murugesu

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201600566

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      Coordinatively unsaturated FeIII metal sites were successfully incorporated into the iconic MOF-5 framework. This new structure, FeIII-iMOF-5, is the first example of an interpenetrated MOF linked through intercalated metal ions, which displays the potential for metal-site addition as a framework connector, thus creating further opportunity for the innovative development of new MOF materials.

  12. Full Papers

    1. Heterogeneous Catalysis

      Ionic Polymer Microspheres Bearing a CoIII–Salen Moiety as a Bifunctional Heterogeneous Catalyst for the Efficient Cycloaddition of CO2 and Epoxides

      Prof. Dr. Yan Leng, Dan Lu, Chenjun Zhang, Prof. Dr. Pingping Jiang, Weijie Zhang and Prof. Dr. Jun Wang

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201600755

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      This cat has five lives: Novel ionic polymer microspheres bearing a CoIII–salen moiety were demonstrated to be highly efficient catalysts (high activity, easy recovery, and reusable) for the cycloaddition reaction of CO2 and epoxides (see figure).

  13. Communications

    1. Hydrosilylation

      Selective Metal-Free Hydrosilylation of CO2 Catalyzed by Triphenylborane in Highly Polar, Aprotic Solvents

      Dr. Debabrata Mukherjee, Daniel F. Sauer, Dr. Alessandro Zanardi and Prof. Dr. Jun Okuda

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201601006

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      Polar power: Triphenylborane in highly polar, aprotic solvents catalyzes the hydrosilylation of CO2 under mild conditions to silyl formates with remarkable selectivity (>95 %) and without over-reductions. This system also promotes reductive hydrosilylation of tertiary amides and dehydrogenative coupling of silane with alcohols.

  14. Full Papers

    1. Inhibitors

      In Situ Proteome Profiling and Bioimaging Applications of Small-Molecule Affinity-Based Probes Derived From DOT1L Inhibitors

      Biwei Zhu, Dr. Hailong Zhang, Sijun Pan, Chenyu Wang, Dr. Jingyan Ge, Prof. Dr. Jun-Seok Lee and Prof. Dr. Shao Q. Yao

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201600259

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      Minimalist “clickable” probes: Small-molecule probes P1 and P2 based on FED1 (a known DOT1L inhibitor) were developed and successfully used in experiments including live-cell imaging, in situ proteome profiling, and off-target identification (see scheme).

  15. Communications

    1. Organic Synthesis | Hot Paper

      RhI-Catalyzed Cyclizative Addition Reaction of 1,6-Enyne and Sulfonyl Chloride by Carbophilic Activation

      Mengyao Dang, Longlei Hou and Dr. Xiaofeng Tong

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201601098

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      C−C bond formation: Cyclizative addition reactions of 1,6-enynes and sulfonyl chlorides by using a [Rh(cod)Cl/dppf] (see scheme) catalyst system are described. The process features the involvement of oxidative addition of sulfonyl chloride to RhI catalyst, which generates [(dppf)(RSO2)RhCl2] as a π-acid species to trigger cyclizative addition in a 6-endo-dig manner by carbophilic activation.

    2. Solvothermal Synthesis

      High Nuclearity Antimonato-Polyoxovanadate Cluster {V15Sb6O42} as a Synthon for the Solvothermal in situ Generation of α- and β-{V14Sb8O42} Isomers

      Michael Wendt, Prof. Dr. Christian Näther and Prof. Dr. Wolfgang Bensch

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201601401

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      Using a water-soluble heteroatom polyoxovanadate cluster with a {V15Sb6O42} cluster as a synthon led to a transformation into a complete different cluster shell of {V14Sb8O42} during various reactions, exhibiting two isomers with different symmetries (D2h and D2d). It resulted into a complicate rearrangement of the origin cluster shell with D3 symmetry (see scheme).

  16. Full Papers

    1. Synthetic Methods | Hot Paper

      Intramolecular Alkene Aminocarbonylation Using Concerted Cycloadditions of Amino-Isocyanates

      Ryan A. Ivanovich, Christian Clavette, Jean-François Vincent-Rocan, Jean-Grégoire Roveda, Dr. Serge I. Gorelsky and Prof. Dr. André M. Beauchemin

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201600574

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      Unusual cycloadditions: Rare N-substituted isocyanates are shown to provide efficient access to cyclic heterocycles containing β-aminocarbonyl motifs through an alkene aminocarbonylation reaction. This study includes an investigation using DFT and the development of several reaction variants. These provide controlled reactions of reactive N-isocyanate intermediates, resulting in milder conditions, improved yields, and a better substrate scope (see scheme).

    2. Efficient Preparation of TMSCCl2Br and Its Use in Dichlorocyclopropanation of Electron-Deficient Alkenes

      Dr. Darren S. Lee, Dr. María Jesús Durán-Peña, Dr. Laurence Burroughs and Prof. Dr. Simon Woodward

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201600607

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      Halo-ed be thy frame: The efficient synthesis of TMSCCl2Br provides easy access to an alternative dichlorocyclopropanation reagent (see scheme). Cyclopropanes from electron-deficient alkenes have been synthesised and the mechanism has been probed with NMR spectroscopy and DFT calculations.

    3. Heterocycles

      Synthesis of Novel Imidazo[1,2-a]pyridin-2-amines from Arylamines and Nitriles via Sequential Addition and I2/KI-Mediated Oxidative Cyclization

      Xianhai Tian, Lina Song, Manman Wang, Zhigang Lv, Dr. Jie Wu, Dr. Wenquan Yu and Prof. Dr. Junbiao Chang

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201600849

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      A novel and practical methodology for the construction of imidazo[1,2-a]pyridin-2-amine frameworks has been developed via sequential addition of arylamines to nitriles and I2/KI-mediated oxidative cyclization.

    4. Mercurated Nucleobase

      5-Mercuricytosine: An Organometallic Janus Nucleobase

      Dattatraya Ukale, Dr. Vaishali S. Shinde and Dr. Tuomas Lönnberg

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201600851

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      Ianus et Mercurius: 5-Mercuricytosine forms HgII-mediated base pairs with thymine and guanine (see graphic). The contribution of the former to the melting temperature of a double-helical oligonucleotide is similar to that of a Watson–Crick base pair. Both of the HgII-mediated base pairs are characterized by a relatively low entropic penalty of formation.

  17. Communications

    1. C−H Functionalization

      Visible-Light-Driven Photocatalytic Activation of Inert Sulfur Ylides for 3-Acyl Oxindole Synthesis

      Xu-Dong Xia, Dr. Liang-Qiu Lu, Wen-Qiang Liu, Dong-Zhen Chen, Yu-Han Zheng, Prof. Dr. Li-Zhu Wu and Prof. Dr. Wen-Jing Xiao

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201600871

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      Visible-light photocatalytic, single-electron-transfer oxidations of inert sulfur ylides generate active radical cations, which enable subsequent intramolecular C−H functionalization to provide significant 3-acyl oxindoles (see scheme). This result is the first example of photochemical annulations of dicarbonyl-stabilized sulfur ylides under extremely mild reaction conditions.

    2. Self-Assembly

      Fluorescent H-Aggregates Hosted by a Charged Cyclodextrin Cavity

      Niyati H. Mudliar and Dr. Prabhat K. Singh

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201600925

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      Flava flavin: A negatively charged β-cyclodextrin derivative, was found to induce aggregation of a well-known amyloid sensing dye, Thioflavin-T, and lead to an unprecedented formation of the rarely observed emissive H-type aggregates of the dye.

    3. Magnetic Resonance Imaging

      Gadolinium-Decorated Silica Microspheres as Redox-Responsive MRI Probes for Applications in Cell Therapy Follow-Up

      Dr. Monica Muñoz Úbeda, Dr. Fabio Carniato, Dr. Valeria Catanzaro, Sergio Padovan, Dr. Cristina Grange, Dr. Stefano Porta, Dr. Carla Carrera, Prof. Lorenzo Tei and Dr. Giuseppe Digilio

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201600962

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      Redox-responsive cellular imaging: Silica microspheres have been decorated with Gd-HP-DO3A-like (gadoteridol-like) complexes through a disulfide bond to obtain a redox-responsive MRI probe. This probe is designed to be interspersed with therapeutic cells within hydrogel capsules to enable the longitudinal follow-up of the redox microenvironment surrounding the embedded cells by MRI.

    4. Photooxidation

      Singlet Oxygen-Induced Furan Oxidation for Site-Specific and Chemoselective Peptide Ligation

      Eirini Antonatou, Dr. Kurt Hoogewijs, Dr. Dimitris Kalaitzakis, Andreas Baudot, Prof. Georgios Vassilikogiannakis and Prof. Annemieke Madder

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201601113

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      Site-specific orthogonal peptide labeling: An efficient and site-selective methodology for the modification of peptides in water has been developed. This mild and controllable technique relies on the combination of molecular oxygen and visible light, which efficiently transforms furan-containing peptides into stable conjugates by using a variety of fluorescent hydrazides.

    5. Aminoboranes

      Ammonium Aminodiboranate: A Long-Sought Isomer of Diammoniate of Diborane and Ammonia Borane Dimer

      Weidong Chen, Dr. Haibo Yu, Dr. Guotao Wu, Dr. Teng He, Zhao Li, Prof. Dr. Zaiping Guo, Prof. Dr. Huakun Liu, Dr. Zhenguo Huang and Prof. Dr. Ping Chen

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201601375

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      At last! Ammonium aminodiboranate ([NH4][BH3NH2BH3]), which is long sought for more than 90 years, is shown to be stable in tetrahydrofuran at −18 °C and decomposes rapidly to NH3BH2NH2BH3 and H2 at elevated temperatures. The decomposition pathway is dictated by the dihydrogen bonding between Hδ+ on NH4+ and Hδ− on BH3, as confirmed by theoretical calculations and experimental results (see scheme). This is different to the interconversion between diammoniate of diborane ([NH3BH2NH3][BH4]) and ammonia borane (NH3BH3).

    6. Heterocycles

      Efficient Synthesis of Dimeric Oxazoles, Piperidines and Tetrahydroisoquinolines from N-Substituted 2-Oxazolones

      Prof. Dr. Yun He, Dr. Piyush K. Agarwal, Dr. I. N. Chaithanya Kiran, Ruocheng Yu, Bei Cao, Cheng Zou, Xinghua Zhou, Huacheng Xu, Biao Xu, Lei Zhu, Prof. Dr. Yu Lan and Prof. Dr. K. C. Nicolaou

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201601471

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      Cascades to molecular complexity and diversity: N-Substituted 2-oxazolones such as depicted, are selectively converted to an array of heterocyclic compounds including dimeric oxazoles, iminosugars and tetrahydroisoquinolines.

  18. Cover Profiles

    1. Synthesis of (E)-4-Bromo-3-methoxybut-3-en-2-one, the Key Fragment in the Polyhydroxylated Chain Common to Oscillariolide and Phormidolides A–C

      Alejandro Gil, Dr. Janire Lamariano-Merketegi, Dr. Adriana Lorente, Prof. Fernando Albericio and Prof. Mercedes Álvarez

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201601578

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      “Confronting a total synthesis is always an attractive challenge and this final objective cannot be achieved without completing minor milestones” Read more about the story behind the cover in the Cover Profile and about the research itself on page ▪▪ ff. (DOI: 10.1002/chem.201600770).

  19. Cover Pictures

    1. You have free access to this content
      Adjacent Lone Pair (ALP) Effect: A Computational Approach for Its Origin

      Huaiyu Zhang, Prof. Wei Wu, Basil M. Ahmed, Prof. Gellert Mezei and Prof. Yirong Mo

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201601555

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      1-Substituted pyrazole can be deprotonated either at its 3- or 5-position, but the 5-position is overwhelmingly preferred as the resulting anion is more stable than the deprotonated anion at the 3-position by both enhanced π conjugation and nucleus–electron electrostatic attraction. Thus, the nature of the renowned adjacent lone pair (ALP) effect is not the generally believed Pauli exchange repulsion between the lone pairs. More information can be found in the Full Paper by W. Wu, Y. Mo et al. (DOI: 10.1002/chem.201600509).

  20. Full Papers

    1. Supramolecular Chemistry

      From Binuclear Complexes to Molecular Necklaces: Incorporating Flexible Ligands into Rotaxanes

      Dr. Elizabeth Viljoen, Dr. Kelong Zhu and Prof. Stephen J. Loeb

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201504831

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      A flexible bipyridine linker forms a simple binuclear, molecular square, complex when coordinated to two convergent PtII corners, but when the linker is converted to the axle of a [2]rotaxane it is rigidified and becomes linear resulting in the formation of a larger molecular necklace; a triangular shaped, molecular necklace is shown in the figure.

    2. Macrocycles

      One-Pot Approach to Organo-Phosphorus–Chalcogen Macrocycles Incorporating Double OP(S)SCn or OP(Se)SeCn Scaffolds: A Synthetic and Structural Study

      Dr. Guoxiong Hua, Junyi Du, Prof. Alexandra M. Z. Slawin and Prof. J. Derek Woollins

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201504832

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      Easy accesses to macrocycles! A variety of phosphorus–chalcogen macrocycles have been synthesised (see figure) readily by using a one-pot three-component condensation reaction of the four-membered ring chalcogenation reagents, disodium alkenyl-diols, and dibromoalkanes.

    3. Hydrides | Hot Paper

      Access to Base Adducts of Low-Valent Organotin-Hydride Compounds by Controlled, Stepwise Hydrogen Abstraction from a Tetravalent Organotin Trihydride

      Dr. Christian P. Sindlinger, Wiebke Grahneis, Frederik S. W. Aicher and Prof. Dr. Lars Wesemann

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201505081

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      Tin-tin time! Formation of a variety of organotin hydrides with tin in the oxidation states SnII, SnI–SnIII, and SnIII–SnIII, all accessed by the controlled removal of hydrogen from the tetravalent Ar′SnIV trihydride (Ar′=2,6-dimesitylphenyl, mesityl=2,4,6-trimethylphenyl; see scheme), is reported.

    4. Photophysics | Hot Paper

      You have full text access to this OnlineOpen article
      Multiple Decay Mechanisms and 2D-UV Spectroscopic Fingerprints of Singlet Excited Solvated Adenine-Uracil Monophosphate

      Dr. Quansong Li, Dr. Angelo Giussani, Dr. Javier Segarra-Martí, Dr. Artur Nenov, Dr. Ivan Rivalta, Prof. Alexander A. Voityuk, Prof. Shaul Mukamel, Dr. Daniel Roca-Sanjuán, Prof. Marco Garavelli and Prof. Lluís Blancafort

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201505086

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      2D-UV fingerprints: Calculations of the excited state decay channels of the adenine uracil monophosphate (ApU) dinucleoside show that several species may contribute to the lifetimes measured experimentally. Simulations of the 2D-UV spectra provide specific fingerprints for each state that will help to discern the mechanistic scenarios (see figure).

    5. Structure–Activity Relationships

      Host–Guest [2+2] Cycloaddition Reaction: Postsynthetic Modulation of CO2 Selectivity and Magnetic Properties in a Bimodal Metal–Organic Framework

      Dr. Arpan Hazra, Dr. Satyanarayana Bonakala, Karteek K. Bejagam, Prof. Dr. Sundaram Balasubramanian and Prof. Dr. Tapas Kumar Maji

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201505131

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      See the light! Modification of pore surfaces by covalent fusion of guest molecules with a host framework and corresponding gas uptake selectivity (e.g., CO2 vs. N2) has been achieved in a porous magnetic host framework by photoinduced postsynthetic modification of the host–guest system through a [2+2] cycloaddition reaction (see figure). The photomodified structure also demonstrates guest-induced reversible magnetic modulation.

  21. Concepts

    1. Metal–Organic Frameworks

      You have free access to this content
      Metal–Organic Frameworks as Catalysts for Oxidation Reactions

      Prof. Dr. Amarajothi Dhakshinamoorthy, Prof. Dr. Abdullah M. Asiri and Prof. Dr. Hermenegildo Garcia

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201505141

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      The state of the art in the use of metal–organic frameworks (MOFs) as heterogeneous catalysts for liquid-phase oxidation of alkenes, alkanes, and alcohols is discussed, with emphasis on the nature of the active sites and on future targets to be set in this area.

  22. Full Papers

    1. Homogeneous Catalysis

      Highly Active Multidentate Ligand-Based Alkyne Metathesis Catalysts

      Dr. Ya Du, Dr. Haishen Yang, Chengpu Zhu, Michael Ortiz, Kenji D. Okochi, Prof. Dr. Richard Shoemaker, Dr. Yinghua Jin and Prof. Dr. Wei Zhang

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201505174

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      Alkyne metathesis catalysts composed of molybdenum(VI) propylidyne and multidentate triphenolmethine ligands have been developed, which show high activity, excellent functional-group tolerance, and long lifetime (remains active in solution for three months at RT).

    2. Self-Assembly

      Control over the Self-Assembly Modes of PtII Complexes by Alkyl Chain Variation: From Slipped to Parallel π-Stacks

      Dr. Naveen Kumar Allampally, Dr. María José Mayoral, Dr. Sarayute Chansai, Dr. María Cristina Lagunas, Prof. Christopher Hardacre, Dr. Vladimir Stepanenko, Prof. Rodrigo Q. Albuquerque and Prof. Dr. Gustavo Fernández

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201600176

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      Weak but significant: The absence or presence of long alkyl side groups (methoxy vs. dodecyloxy) is found to govern the packing modes (parallel vs. slipped stacks) of hydrophobic bis(pyridyl) PtII complexes featuring an extended π-surface (see figure). Unconventional weak interactions involving metal-polarized chlorine groups have thereby established themselves as new synthons in the field of supramolecular chemistry.

    3. Molecular Switches

      Multistate Switches: Ruthenium Alkynyl–Dihydroazulene/Vinylheptafulvene Conjugates

      Alexandru Vlasceanu, Cecilie L. Andersen, Dr. Christian R. Parker, Prof. Dr. Ole Hammerich, Dr. Thorbjørn J. Morsing, Dr. Martyn Jevric, Dr. Søren Lindbæk Broman, Prof. Dr. Anders Kadziola and Prof. Dr. Mogens Brøndsted Nielsen

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201600178

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      Multimode switching: Combining the dihydroazulene/vinylheptafulvene (DHA/VHF) photo/thermoswitch with a Ru–acetylide ([Ru*]) metal complex in four examples provides molecules that can potentially exist in six different states, individually stimulated by using light/heat, oxidation/reduction, and acid/base. Switching and access to these states were found to depend strongly on the electronic communication between the two units in these conjugates.

    4. Green Chemistry

      Applying Mechanochemistry for Bottom-Up Synthesis and Host–Guest Surface Modification of Semiconducting Nanocrystals: A Case of Water-Soluble β-Cyclodextrin-Coated Zinc Oxide

      Piotr Krupiński, Arkadiusz Kornowicz, Dr. Kamil Sokołowski, Anna M. Cieślak and Prof. Janusz Lewiński

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201600182

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      Go dry to get wet: Solventless synthesis of water-soluble ZnO nanocrystals is achieved by a mild mechanochemical pathway based on rational design of oxo-zinc precursors. The applied bottom-up methodology allows for synthesis of organic ligand-coated nanocrystals as well as their host–guest surface modification with cyclodextrins in both one-pot sequential or one-step three-component process (see figure).

  23. Communications

    1. Electronic Structure

      Ferrocene-Substituted Naphthalenediimide with Broad Absorption and Electron-Transport Properties in the Segregated-Stack Structure

      Dr. Atsuro Takai, Dr. Daisuke Sakamaki, Prof. Dr. Shu Seki, Dr. Yoshitaka Matsushita and Dr. Masayuki Takeuchi

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201600196

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      Ferrocene-Assisted π-Stacking: A new naphthalenediimide-ferrocene conjugate (Fc-NDI-Fc) was designed. The Fc units work as electron-donating substituents, in contrast to the electron-deficient NDI unit, resulting in broad charge-transfer absorption of Fc-NDI-Fc up to 1500 nm in the solid state. The Fc-NDI-Fc crystal has a segregated-stack structure with the extended π-orbital overlap of the NDI units, leading to the electron-transport events.

  24. Full Papers

    1. Multicomponent Reactions

      Trityl Isocyanide as a Mechanistic Probe in Multicomponent Chemistry: Walking the Line between Ugi- and Strecker-type Reactions

      Răzvan C. Cioc, Hans D. Preschel, Gydo van der Heijden, Dr. Eelco Ruijter and Prof. Dr. Romano V. A. Orru

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201600285

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      Fate of the nitrilium ion: The application of trityl isocyanide as a mechanistic tool to dissect different reaction pathways in multicomponent chemistry is described. This reagent can be employed as a cyanide source in the Strecker reaction and as a convertible isocyanide in the preparation of N-acyl amino acids by Ugi 4CR/detritylation and free imidazo[1,2-a]pyridin-3-amines by Groebke–Blackburn–Bienaymé 3CR condensation/deprotection. Chemoselective transformations were achieved by the rational choice of reaction conditions.

    2. Structure Elucidation | Hot Paper

      Total Synthesis and Complete Stereostructure of a Marine Macrolide Glycoside, (−)-Lyngbyaloside B

      Prof. Dr. Haruhiko Fuwa, Naoya Yamagata, Yuta Okuaki, Yuya Ogata, Asami Saito and Prof. Dr. Makoto Sasaki

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201600341

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      Structural reassignment: Total synthesis of the proposed and correct structures of (−)-lyngbyaloside B (see figure), a marine macrolide glycoside, has been achieved. The synthesis entailed an Abiko–Masamune aldol reaction, a vinylogous Mukaiyama aldol reaction, and an acyl ketene macrocyclization to forge the 14-membered macrolactone. The present work established the complete stereostructure of this natural product in an unambiguous manner.

    3. Hydrogen Bonds | Hot Paper

      Weak Intermolecular Hydrogen Bonds with Fluorine: Detection and Implications for Enzymatic/Chemical Reactions, Chemical Properties, and Ligand/Protein Fluorine NMR Screening

      Dr. Claudio Dalvit and Dr. Anna Vulpetti

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201600446

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      Detection and relevance of weak HB with fluorine: Weak hydrogen bonds between fluorine and water and other donors have been detected using a combination of 1H and 19F NMR spectroscopies. Their implications for reactivity, chemical and physical properties, and the relative sensitivities of ligand- and protein-based 19F NMR screening methods have been analyzed (see graphic).

    4. Bioinorganic Chemistry

      Ferrous Iron Binding Key to Mms6 Magnetite Biomineralisation: A Mechanistic Study to Understand Magnetite Formation Using pH Titration and NMR Spectroscopy

      Dr. Andrea E. Rawlings, Dr. Jonathan P. Bramble, Andrea M. Hounslow, Prof. Michael P. Williamson, Dr. Amy E. Monnington, Dr. David J. Cooke and Dr. Sarah S. Staniland

      Article first published online: 26 APR 2016 | DOI: 10.1002/chem.201600322

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      Biomimetic synthesis: Mms6 is a key protein involved in the formation of magnetite nanocrystals by magnetotactic bacteria. To understand the role of Mms6 during in vitro iron oxide precipitation, in situ pH titrations (see figure), NMR spectroscopy, and molecular simulations were performed. The results suggest that Mms6 functions as a magnetite nucleating protein under conditions where ferrous ions predominate.

    5. Radical Reactions

      Peroxyl Radical Reactions in Water Solution: A Gym for Proton-Coupled Electron-Transfer Theories

      Dr. Riccardo Amorati, Dr. Andrea Baschieri, Gloria Morroni, Rossana Gambino and Prof. Luca Valgimigli

      Article first published online: 25 APR 2016 | DOI: 10.1002/chem.201504492

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      Radical kinetics: A simple and reliable method to measure the kinetics of peroxyl radical reactions in water is described (see figure). The proton-coupled electron transfer from a variety of compounds was investigated. Electron-poorer phenols react by concerted electron-proton transfer (EPT or CPET), whereas electron-richer phenols and phenoxide anions react by multi-site EPT (separated CPET) in which water acts as proton relay, similarly to the chemistry of radical enzymes.

    6. Anticancer Agents

      Nucleotide Binding Preference of the Monofunctional Platinum Anticancer-Agent Phenanthriplatin

      Dr. Imogen A. Riddell, Dr. Timothy C. Johnstone, Dr. Ga Young Park and Prof. Stephen J. Lippard

      Article first published online: 25 APR 2016 | DOI: 10.1002/chem.201600236

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      Purine preference: Phenanthriplatin generates biologically relevant adducts at both adenosine and guanosine nucleotides. In contrast to reactions with 9-alkylguanine, phenanthriplatin generates a mixture of isomeric and diastereomeric species upon reaction with 9-methyladenine. Characterization of the different adducts facilitates kinetic analysis into the relative rates of adduct formation (see figure).

  25. Communications

    1. Organometallic Chemistry

      Siloxymethylamines as Aminomethylation Reagents for Amines Leading to Labile Diaminomethanes That can be Trapped as Their [Mo(CO)4] Complexes

      Hemant K. Sharma, Paulina E. Gonzalez, Alexander L. Craig, Sanchita Chakrabarty, Alejandro Metta-Magaña and Prof. Keith H. Pannell

      Article first published online: 25 APR 2016 | DOI: 10.1002/chem.201600810

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      Previously unreported simple diaminomethanes were readily obtained from reactions of siloxymethylamines with secondary amines. They are labile materials that readily disproportionate, but can be trapped by metal coordination (see scheme).

  26. Full Papers

    1. Heterogeneous Catalysis

      Mild and Selective Catalytic Hydrogenation of the C=C Bond in α,β-Unsaturated Carbonyl Compounds Using Supported Palladium Nanoparticles

      Dr. Anuja Nagendiran, Vlad Pascanu, Dr. Antonio Bermejo Gómez, Greco González Miera, Dr. Cheuk-Wai Tai, Dr. Oscar Verho, Prof. Dr. Belén Martín-Matute and Prof. Dr. Jan-E. Bäckvall

      Article first published online: 25 APR 2016 | DOI: 10.1002/chem.201600878

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      Make it selective! Make it porous! Chemoselective reduction of the C=C bond in a variety of α,β-unsaturated carbonyl compounds using supported palladium nanoparticles is reported (see figure). Studies revealed that both palladium on mesocellular foam (MCF) and palladium on metal–organic framework (MOF) were superior in activity and selectivity compared to commercial Pd/C.

  27. Communications

    1. Fused Heterocycles

      Aromatic Fused [30] Heteroannulenes with NIR Absorption and NIR Emission: Synthesis, Characterization, and Excited-State Dynamics

      Abhijit Mallick, Juwon Oh, Prof. Dr. Dongho Kim and Prof. Dr. Harapriya Rath

      Article first published online: 25 APR 2016 | DOI: 10.1002/chem.201600917

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      Two hitherto unknown planar aromatic [30] fused heteroannulenes (1.1.0.1.1.0) with near-IR (NIR) absorption in free-base form and protonation-induced enhanced NIR emission are reported.

    2. Amination

      Defined Palladium–Phthalimidato Catalysts for Improved Oxidative Amination

      Dr. Claudio Martínez and Prof. Dr. Kilian Muñiz

      Article first published online: 25 APR 2016 | DOI: 10.1002/chem.201601128

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      Coordination mission completed! Free phthalimide forms stable monomeric or trimeric coordination compounds with palladium. These complexes serve as defined palladium catalysts for oxidative amination reactions with phthalimide as the nitrogen source (see scheme). Examples include the diamination and aminooxygenation of alkenes and the C−H amination of benzene.

    3. Magnetic Properties

      White Light Emissive DyIII Single-Molecule Magnets Sensitized by Diamagnetic [CoIII(CN)6]3− Linkers

      Dr. Szymon Chorazy, Dr. Michał Rams, Dr. Koji Nakabayashi, Prof. Dr. Barbara Sieklucka and Prof. Dr. Shin-ichi Ohkoshi

      Article first published online: 25 APR 2016 | DOI: 10.1002/chem.201601244

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      Emissive Dy–Co molecular magnet: Magnetically anisotropic DyIII complexes with 3-hydroxypyridine were embedded with diamagnetic [CoIII(CN)6]3− anions into the zig-zag cyanido-bridged chains (see scheme). They combine the single-molecule magnet (SMM) behavior with a significant zero-field energy barrier of spin inversion, ΔE≈460 K, and the white light Dy-centered emission sensitized both by organic ligand and hexacyanidocobaltate(III) linkers.

    4. Synthetic Methods

      Low-pressure Cobalt-Catalyzed Enantioselective Hydrovinylation of Vinylarenes

      Dr. Sohajl Movahhed, Julia Westphal, Dr. Mehmet Dindaroğlu, Dr. Anna Falk and Prof. Dr. Hans-Günther Schmalz

      Article first published online: 25 APR 2016 | DOI: 10.1002/chem.201601283

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      Combination of a chiral TADDOL-derived phosphine–phosphite ligand with CoCl2 was the key for the development of a robust and reliable protocol for the enantioselective codimerization of various functionalized vinylarenes with ethylene (see scheme).

  28. Corrigenda

    1. You have free access to this content
  29. Full Papers

    1. Tripodal Ligands

      A Boron-Fluorinated Tris(pyrazolyl)borate Ligand (FTp*) and Its Mono- and Dinuclear Copper Complexes [Cu(FTp*)2] and [Cu2(FTp*)2]: Synthesis, Structures, and DFT Calculations

      Dr. Timo Augenstein, Franziska Dorner, Kevin Reiter, Hanna E. Wagner, Dr. Delphine Garnier, Prof. Dr. Wim Klopper and Prof. Dr. Frank Breher

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201504545

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      Fluorinated at boron: The mono- and dinuclear copper complexes [CuII(FTp*)2] and [CuI2(FTp*)2] containing the so-far unprecedented boron-fluorinated tris(pyrazolyl)borate ligand (FTp*) are reported. The short Cu⋅⋅⋅Cu distance in [CuI2(FTp*)2] was predicted by DFT-D3 calculations to be dictated by dispersion interactions between all atoms in the complex, whereas the Cu–Cu dispersion contribution itself is only very small.

    2. Doping

      Methyllithium-Doped Naphthyl-Containing Conjugated Microporous Polymer with Enhanced Hydrogen Storage Performance

      Dr. Dan Xu, Dr. Lei Sun, Dr. Gang Li, Dr. Jin Shang, Rui-Xia Yang and Prof. Wei-Qiao Deng

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201504666

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      Increased H2 storage: Based on a combined theoretical and experimental approach, a new strategy was developed to enhance hydrogen uptake of naphthyl-containing conjugated microporous polymers through methyllithium doping (see figure).

    3. Mesoporous Materials

      On the Mesoporogen-Free Synthesis of Single-Crystalline Hierarchically Structured ZSM-5 Zeolites in a Quasi-Solid-State System

      Dr. Tongguang Ge, Prof. Dr. Zile Hua, Dr. Xiaoyun He, Dr. Jian Lv, Prof. Dr. Hangrong Chen, Prof. Dr. Lingxia Zhang, Dr. Heliang Yao, Dr. Ziwei Liu, Dr. Chucheng Lin and Prof. Dr. Jianlin Shi

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201504813

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      Full steam ahead! Based on the steam-assisted crystallization (SAC) approach, ZSM-5-type single-crystalline hierarchically structured zeolites with penetrating and three-dimensionally well-interconnected mesoporosity have been obtained by using no mesoporogens and a minimized amount of microporous-structure-directing agent, tetrapropylammonium hydroxide (see figure).

    4. Supramolecular Assemblies

      An Elaborate Supramolecular Assembly for a Smart Nanodevice for Ratiometric Molecular Recognition and Logic Gates

      Yu-Jie Xie, Wen-Yu Wu, Hao Chen, Xiang Li, Prof. Hao-Li Zhang, Liang-Liang Liu, Xing-Xin Shao, Chang-Fu Shan, Prof. Wei-Sheng Liu and Prof. Yu Tang

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201505082

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      A smart nanodevice for ratiometric molecular recognition and nano-logic gates has been successfully fabricated by using an elaborate supramolecular assembly strategy that includes the precise assembly of a bifunctional connector sulfonatocalix[4]arene on quaternized cationic carbon dots by inclusion complexation and electrostatic interactions, and the incorporation of Tb3+ ions by in situ coordination.

    5. Cancer

      Mono- and Dinuclear Phosphorescent Rhenium(I) Complexes: Impact of Subcellular Localization on Anticancer Mechanisms

      Rui-Rong Ye, Dr. Cai-Ping Tan, Mu-He Chen, Liang Hao, Prof. Liang-Nian Ji and Prof. Zong-Wan Mao

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201505160

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      Directing by design: The anticancer mechanisms of phosphorescent rhenium(I) tricarbonyl polypyridine complexes are found to be closely associated with their organelle-specific localizations (see figure).

    6. Polysilane Reactions

      You have full text access to this OnlineOpen article
      Cationic Si−H−Si Bridges in Polysilanes: Their Detection and Targeted Formation in Stable Ion Studies

      Dr. Lena Albers, Dr. Judith Baumgartner, Prof. Christoph Marschner and Prof. Thomas Müller

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201600116

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      The hydrogen trick: A new synthetic approach has been established for trapping highly reactive and short-lived cationic intermediates of sila-Wagner–Meerwein rearrangements of polysilanes (see figure). The preference for 2e–3c Si−H−Si bridges can be used to identify transient intermediates by low-temperature 29Si NMR spectroscopy. This method allows for a general understanding of rearrangement processes in Lewis acid catalyzed polysilane transformations.

    7. Host–Guest Systems

      Disorder of Hydrofluorocarbon Molecules Entrapped in the Water Cages of Structure I Clathrate Hydrate

      Dr. Satoshi Takeya, Dr. Konstantin A. Udachin, Dr. Igor L. Moudrakovski, Dr. Ryo Ohmura and Dr. John A. Ripmeester

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201600122

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      Water versus fluorine: Clathrate hydrates encaging hydrofluorocarbons as guests show both isotropic and anisotropic distributions within host water cages, depending on the number of fluorine atoms in the guest molecule; this is caused by changes in intermolecular interactions to host water molecules in the hydrates (see figure).

    8. Homogeneous Catalysis

      Direct Synthesis of Highly Substituted Pyrroles and Dihydropyrroles Using Linear Selective Hydroacylation Reactions

      Manjeet K. Majhail, Dr. Paul M. Ylioja and Prof. Michael C. Willis

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201600311

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      Down the line: Rhodium catalysts featuring small-bite-angle bisphosphine ligands allow the linear-selective combination of aldehydes and propargylic amines (see scheme). The resultant γ-amino-enone products are converted in situ to a diverse range of substituted pyrroles. Allylic amine substrates can also be employed, leading in these cases to dihydropyrrole products.

    9. Structure Elucidation

      Montecrinanes A–C: Triterpenes with an Unprecedented Rearranged Tetracyclic Skeleton from Celastrus vulcanicola. Insights into Triterpenoid Biosynthesis Based on DFT Calculations

      Dr. Martín Purino, Dr. Alejandro E. Ardiles, Dr. Oliver Callies, Dr. Ignacio A. Jiménez and Prof. Isabel L. Bazzocchi

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201600294

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      Uncovering skeletons: Three new triterpenes (montecrinanes A–C) with an unprecedented 6/6/6/6-fused tetracyclic carbon skeleton were isolated from the root bark of Celastrus vulcanicola. The biogenetic pathway for the montecrinane and D:B-friedobaccharane skeletons were proposed through DFT calculations (see figure).

    10. Metal–Organic Frameworks | Hot Paper

      Adsorption of Carbon Dioxide on Unsaturated Metal Sites in M2(dobpdc) Frameworks with Exceptional Structural Stability and Relation between Lewis Acidity and Adsorption Enthalpy

      Ga Young Yoo, Dr. Woo Ram Lee, Hyuna Jo, Joonho Park, Jeong Hwa Song, Kwang Soo Lim, Dr. Dohyun Moon, Hyun Jung, Juhyung Lim, Dr. Sang Soo Han, Prof. Dr. Yousung Jung and Prof. Dr. Chang Seop Hong

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201600189

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      Open access: A series of metal–organic frameworks M2(dobpdc) (M=Mn, Co, Ni, Zn; H4dobpdc=4,4′-dihydroxy-1,1′-biphenyl-3,3′-dicarboxylic acid) with a highly dense arrangement of open metal sites along hexagonal channels were prepared. The Lewis acidity (Δinline image ) of the open metal sites, which follows the order Mn<Co< Ni >Zn, is correlated with the CO2 adsorption enthalpy (Qst; see figure).

    11. Reaction Mechanisms

      DFT Rationalization of the Diverse Outcomes of the Iodine(III)-Mediated Oxidative Amination of Alkenes

      Ignacio Funes-Ardoiz, Dr. W. M. C. Sameera, R. Martín Romero, Dr. Claudio Martínez, Dr. José A. Souto, Dr. Diego Sampedro, Prof. Dr. Kilian Muñiz and Prof. Dr. Feliu Maseras

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201600415

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      The Janus face of bissulfonimides: DFT uncovers the dual role of the bissulfonimide nitrogen source in iodine(III)-promoted oxidative amination of alkenes. These show a Janus-type behavior and react as O-centered nucleophiles in the initial step of alkene functionalization (see scheme). Subsequently, they provide N-nucleophilicity to arrive at two selective C−N bond forming events leading to the final diamine product (in 1,2-disubstituted alkenes) or the allylic amination product (in 1,1-disubstituted alkenes).

    12. Dyes/Pigments

      Soluble Flavanthrone Derivatives: Synthesis, Characterization, and Application to Organic Light-Emitting Diodes

      Kamil Kotwica, Dr. Piotr Bujak, Dr. Przemyslaw Data, Wojciech Krzywiec, Damian Wamil, Dr. Piotr A. Gunka, Lukasz Skorka, Dr. Tomasz Jaroch, Prof. Robert Nowakowski, Prof. Adam Pron and Prof. Andrew Monkman

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201600513

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      New life for an old dye: Simple modification of flavanthrone, an old, intractable, and almost-forgotten vat dye, by reduction of its carbonyl groups to phenolates followed by O-alkylation, gave a new group of solution-processable, electroactive, conjugated compounds (see figure). Their HOMO and LUMO energies, as well as their ionization potentials and electron affinities, make them suitable for application as components of organic light-emitting diodes.

    13. Helicenes

      Electronic Structures and Chiroptical Properties of Post-functionalized Helicene Quinones

      Dr. David Schweinfurth, Marcella Mazzolini, Dr. Dmytro Neshchadin, Carolin Hoyer, Roman Geier, Dr. Karl Gatterer, Dr. Nils Trapp, Prof. Dr. Georg Gescheidt and Prof. Dr. François Diederich

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201600611

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      Let's get curly: Post-functionalization reactions of helicenes are presented that allowed for the synthesis of redox-active helicene o- and p-quinones (see figure). UV/Vis, ECD, and EPR spectroscopy, electrochemical analysis, and DFT calculations were used to reveal structure–property relationships.

    14. Macrocycles | Hot Paper

      Aggregation-Induced Emission of Platinum(II) Metallacycles and Their Ability to Detect Nitroaromatics

      Aniket Chowdhury, Prodip Howlader and Prof. Partha Sarathi Mukherjee

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201600698

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      Glowing sensors: Platinum(II) acceptors, containing platinum–carbazole and –triphenylamine backbones, self-assemble with linear dipyridyl donors to form molecular squares and hexagons. Two of the macrocycles are white-light emitters in THF (see figure; AIE=aggregation- induced emission). The luminescent nature of the macrocycles is utilized for the detection of nitroaromatic compounds (NACs).

  30. Communications

    1. Materials Chemistry

      Ultrafast Preparation of Black Phosphorus Quantum Dots for Efficient Humidity Sensing

      Dr. Chongyang Zhu, Prof. Feng Xu, Dr. Ling Zhang, Prof. Minli Li, Prof. Jing Chen, Dr. Shuhong Xu, Dr. Guangguang Huang, Dr. Wenhao Chen and Prof. Litao Sun

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201600719

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      High turbulent shear rate generated by a household kitchen blender has been utilized to disintegrate bulk black phosphorus (BP) crystals into black phosphorous quantum dots (BPQDs), which has been demonstrated to exhibit excellent humidity sensing and photothermal converting properties (see figure).

  31. Full Papers

    1. Synthetic Methods | Hot Paper

      Asymmetric Hydrogenation of Isoxazolium Triflates with a Chiral Iridium Catalyst

      Ryuhei Ikeda and Prof. Ryoichi Kuwano

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201600732

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      Optically active isoxazolines or isoxazolidines were obtained with high stereoselectivity by hydrogenation of isoxazolium triflates with a chiral iridium catalyst (see scheme). The undesirable N−O bond cleavage that commonly accompanies the reaction of oxazoles with H2 was completely avoided by using the iridium catalyst.

    2. Photophysics

      Benzoporphyrins: Selective Co-sensitization in Dye-Sensitized Solar Cells

      Fabian Lodermeyer, Dr. Rubén D. Costa, Dr. Jenny Malig, Prof. Dr. Norbert Jux and Prof. Dr. Dirk M. Guldi

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201600802

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      The dream team: The complementary absorptions of benzoporphyrins and N719 renders them promising candidates for co-sensitization of DSSCs. More important is, however, the fact that metallated benzoporphyrins reveal a TiO2–nanoparticle attachment that is size and aggregation dependent. In light of the latter, an efficiency improvement of 39 % has been achieved upon selective adsorption of benzoporphyrins and N719 onto different layers of TiO2 photoelectrode (see figure).

    3. Rearrangement Reactions

      Direct Observation of Carbamoylnitrenes

      Hongmin Li, Huabin Wan, Zhuang Wu, Dingqing Li, Prof. Dr. Didier Bégué, Prof. Dr. Curt Wentrup and Prof. Dr. Xiaoqing Zeng

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201600824

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      Rearrange it! Elusive carbamoylnitrenes, R2NC(O)N (R=H, Me), assumed since the 1890s to be key intermediates in the Curtius rearrangement of carbamoyl azides, have been generated and observed directly for the first time by IR spectroscopy following ArF laser matrix photolysis of the corresponding azides (see figure).

  32. Communications

    1. Total Synthesis

      A General, Concise Strategy that Enables Collective Total Syntheses of over 50 Protoberberine and Five Aporhoeadane Alkaloids within Four to Eight Steps

      Shiqiang Zhou and Prof. Dr. Rongbiao Tong

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201601245

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      One strategy for all members: A concise, catalytic, and general strategy is developed for efficient total syntheses of more than 50 protoberberine alkaloid natural products and five aporhoeadane alkaloids within 4–8 steps for each molecule. This synthesis features two key catalytic processes: CuI-catalyzed redox-A3 reaction and Pd-catalyzed reductive carbocyclization, in combination with other catalytic reactions, such as PtO2-catalyzed hydrogenation, RhI-catalyzed decarbonylation, and RuO4-catalyzed oxidation/isomerization, etc.

  33. Cover Pictures

    1. You have free access to this content
      Hückel's Rule of Aromaticity Categorizes Aromatic closo Boron Hydride Clusters

      Dr. Jordi Poater, Prof. Dr. Miquel Solà, Prof. Dr. Clara Viñas and Prof. Dr. Francesc Teixidor

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201601248

      Thumbnail image of graphical abstract

      By means of the electronic confined space analogy (ECSA), the (4 n+2) π Hückel rule, as followed by 2D aromatic [n]annulenes, has been connected to the 3D aromatic Wade-Mingos’ rule found for closo [BnHn]2- clusters. Application of the ESCA method to medium and large boron clusters allows their classification into different series according to the n value of the Hückel (4 n+2) π rule (photo credit: Iñaqui Sanjuán Pertusa). More information can be found in the Full Paper by M. Solá, F. Teixidor, et al. (DOI: 10.1002/chem.201600510).

  34. Communications

    1. Donor–Acceptor Systems

      Stibinidene and Bismuthinidene as Two-Electron Donors for Transition Metals (Co and Mn)

      Iva Vránová, Dr. Mercedes Alonso, Dr. Roman Jambor, Prof. Aleš Růžička, Dr. Milan Erben and Dr. Libor Dostál

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201601272

      Thumbnail image of graphical abstract

      Generous donation: The synthesis, structure and bonding analysis of stibinidene and bismuthinidene ionic complexes of cobalt and manganese is presented. The pnictinidenes are coordinated as terminal ligands and act as two-electron donors in this set of compounds, an unprecedented feature in the chemistry of heavy Group 15 elements.

  35. Cover Profiles

    1. Total Synthesis and Complete Stereostructure of a Marine Macrolide Glycoside, (−)-Lyngbyaloside B

      Prof. Dr. Haruhiko Fuwa, Naoya Yamagata, Yuta Okuaki, Yuya Ogata, Asami Saito and Prof. Dr. Makoto Sasaki

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201601518

      Thumbnail image of graphical abstract

      What puzzled us very much in this study was the structure of lyngbyaloside B.” Read more about the story behind the cover in the Cover Profile and about the research itself on page ▪▪ ff. (DOI: 10.1002/chem.201600341).

  36. Cover Pictures

    1. You have free access to this content
      Monolayer Co3O4 Inverse Opals as Multifunctional Sensors for Volatile Organic Compounds

      Chul-Soon Lee, Zhengfei Dai, Seong-Yong Jeong, Chang-Hoon Kwak, Bo-Young Kim, Do Hong Kim, Prof. Ho Won Jang, Joon-Shik Park and Prof. Jong-Heun Lee

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201601557

      Thumbnail image of graphical abstract

      Monolayer Co3O4 inverse opal thin film sensors containing periodic arrays of pores have been synthesized by using sacrificial templates. The Co3O4 sensor showed high response to ethanol at 200 oC, as well as high selectivity to xylene and toluene at 250 and 275 oC, respectively. Unprecedentedly, high ethanol response and temperature-modulated control of gas selectivity were attributed to the highly chemiresistive inverse opal nanoarchitectures and to the tuned catalytic promotion of different gas-sensing reactions. More information can be found in the Full Paper by J.-H. Lee et al. (DOI: 10.1002/chem.201505210).

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      Structure–Reactivity Relationship in the Frustrated Lewis Pair (FLP)-Catalyzed Hydrogenation of Imines

      Dipl.-Chem. Sebastian Tussing, Dr. Karl Kaupmees and Prof. Dr. Jan Paradies

      Article first published online: 23 APR 2016 | DOI: 10.1002/chem.201601558

      Thumbnail image of graphical abstract

      What makes an FLP a good catalyst? Thus far, a number of frustrated Lewis pairs (FLPs) are reported in the literature, but not all of them activate molecular hydrogen. This phenomenon has been addressed by the physical-organic investigation of the Lewis base as component in an FLP catalyst. The FLP′s performance in the autoinduced hydrogenation is intrinsically dependent on the electron-donating ability of the Lewis base providing a detailed structure–reactivity relationship in FLP catalysis. More information can be found in the Full Paper by J. Paradies, et al. (DOI: 10.1002/chem.201600716).

  37. Full Papers

    1. Chiral Crystals

      Mechanical Motion of Chiral Azobenzene Crystals with Twisting upon Photoirradiation

      Takuya Taniguchi, Juri Fujisawa, Dr. Motoo Shiro, Prof. Dr. Hideko Koshima and Prof. Dr. Toru Asahi

      Article first published online: 21 APR 2016 | DOI: 10.1002/chem.201505149

      Thumbnail image of graphical abstract

      Twist and bent: A plate-like chiral azobenzene crystal bent backward with twisting upon UV irradiation from the front. UV irradiation from the rear bent forward the crystal with twisting (see figure).

    2. Hydrogen Bonds

      Uncovering Intramolecular π-Type Hydrogen Bonds in Solution by NMR Spectroscopy and DFT Calculations

      Prof. Dr. Piero Mastrorilli, Prof. Vito Gallo, Dr. Stefano Todisco, Prof. Mario Latronico and Dr. Giacomo Saielli

      Article first published online: 21 APR 2016 | DOI: 10.1002/chem.201600078

      Thumbnail image of graphical abstract

      Hydrogen bonds in solution: The existence of a π-type hydrogen bond between the PO−H and the C≡C triple bond in the σ-acetylide complex [(PHCy2)(η1-Me3SiC≡C)Pt(μ-PCy2)Pt(PHCy2){κP-P(OH)Cy2}](Pt–Pt) (2) in solution was proven by multinuclear NMR spectroscopy and confirmed by relativistic DFT calculations on model systems of 2. The estimated hydrogen-bonding energy and the calculated coupling values and chemical shift indicate a remarkably strong π-type interaction (see scheme).

    3. Hydroboration

      η4-HBCC-σ,π-Borataallyl Complexes of Ruthenium Comprising an Agostic Interaction

      Koushik Saha, Benson Joseph, Rongala Ramalakshmi, Dr. R. S. Anju, Dr. Babu Varghese and Prof. Sundargopal Ghosh

      Article first published online: 21 APR 2016 | DOI: 10.1002/chem.201600181

      Thumbnail image of graphical abstract

      Building bridges: Hydroboration of σ-borane complexes with alkynes form novel η4-σ,π-borataallyl complexes (see figure). An agostic interaction was also found to be present, which is rare among the borataallyl complexes.

    4. Natural Products

      Engyodontochones, Antibiotic Polyketides from the Marine Fungus Engyodontium album Strain LF069

      Prof. Dr. Bin Wu, Dr. Jutta Wiese, Arlette Wenzel-Storjohann, Susan Malien, Dr. Rolf Schmaljohann and Prof. Dr. Johannes F. Imhoff

      Article first published online: 21 APR 2016 | DOI: 10.1002/chem.201600430

      Thumbnail image of graphical abstract

      Continuing the MRSA fight: Six new and two known polyketides with a basic structure of an anthraquinone-xanthone were isolated from mycelia and culture broth of the fungus Engyodontium album strain LF069 (see figure). A number of the compounds exhibited inhibitory activity against methicillin-resistant Staphylococcus aureus (MRSA) that was 10-fold stronger than chloramphenicol.

    5. Macrocyclic Structures

      Incorporation of a Phenanthrene Subunit into a Sapphyrin Framework: Synthesis of Expanded Aceneporphyrinoids

      Dr. Bartosz Szyszko, Marcin Małecki, Dr. Anna Berlicka, Michał J. Białek, Dr. Agata Białońska, Kamil Kupietz, Dr. Ewa Pacholska-Dudziak and Prof. Lechosław Latos-Grażyński

      Article first published online: 21 APR 2016 | DOI: 10.1002/chem.201600606

      Thumbnail image of graphical abstract

      Combining differences: 32-Hetero-5,6-dimethoxyphenanthrisapphyrins link the structural features of expanded porphyrins and polycyclic aromatic hydrocarbons. Their demethoxylation yield nonaromatic 32-hetero-5,6-dioxophenanthrisapphyrins (see scheme).

  38. Communications

    1. Acylation

      Exploring Cooperative Effects in Oxidative NHC Catalysis: Regioselective Acylation of Carbohydrates

      Dr. David L. Cramer, Srikrishna Bera and Prof. Dr. Armido Studer

      Article first published online: 21 APR 2016 | DOI: 10.1002/chem.201601398

      Thumbnail image of graphical abstract

      Sweet and Selective! Various sugar derivatives, including amino sugars, are acylated with complete selectivity for O-acylation over N-acylation using oxidative N-heterocyclic carbene (NHC) catalysis (see scheme). Secondary alcohols in sugars are differentiated with high selectivity and the concept of using two different NHCs in NHC catalysis is introduced.

    2. Organic Chemistry

      Rhodium-Catalyzed Intramolecular [5+2] Cycloaddition of Inverted 3-Acyloxy-1,4-enyne and Alkyne: Experimental and Theoretical Studies

      Dr. Xiaoxun Li, Wangze Song, Xiaona Ke, Prof. Dr. Xiufang Xu, Prof. Dr. Peng Liu, Prof. Dr. K. N. Houk, Dr. Xian-liang Zhao and Prof. Dr. Weiping Tang

      Article first published online: 20 APR 2016 | DOI: 10.1002/chem.201601195

      Thumbnail image of graphical abstract

      Go cyclo! A new intramolecular [5+2] cycloaddition has been developed for the synthesis of bicyclic ring systems (see scheme). Multiple mechanistic pathways become possible for this new [5+2] cycloaddition and they are investigated by computational studies.

  39. Full Papers

    1. Mesoporous Materials | Hot Paper

      Synthesis of Mesoporous Transition-Metal Phosphates by Polymeric Micelle Assembly

      Dr. Bishnu Prasad Bastakoti, Dr. Yunqi Li, Dr. Sudhina Guragain, Dr. Malay Pramanik, Prof. Saad M. Alshehri, Dr. Tansir Ahamad, Dr. Zongwen Liu and Prof. Yusuke Yamauchi

      Article first published online: 18 APR 2016 | DOI: 10.1002/chem.201600435

      Thumbnail image of graphical abstract

      Micelle assembly: One-pot synthesis of mesoporous transition-metal phosphates with variable metal compositions is reported. This simple and flexible polymeric micelles-assembly approach allowed an easy synthesis of various mesoporous metal phosphates (see figure).

  40. Communications

    1. Dyes/Pigments

      Tetramethoxy-Aminorhodamine (TMARh): A Bichromophore, an Improved Fluorophore, and a pH Switch

      Dr. Thomas Just Sørensen, Dr. Dong Shi and Prof. Dr. Bo W. Laursen

      Article first published online: 18 APR 2016 | DOI: 10.1002/chem.201600496

      Thumbnail image of graphical abstract

      A new route to rhodamines is reported, resulting in tetramethoxy-rhodamines with improved photophysical properties. It was found that tetramethoxy-aminorhodamine is a bichromophore and a very efficient pH-responsive dye.

    2. Photocatalysis

      Nanoflower-Like Bi2WO6 Encapsulated in ORMOSIL as a Novel Photocatalytic Antifouling and Foul-Release Coating

      Gabriele Scandura, Dr. Rosaria Ciriminna, Prof. Yi-Jun Xu, Dr. Mario Pagliaro and Prof. Giovanni Palmisano

      Article first published online: 18 APR 2016 | DOI: 10.1002/chem.201600831

      Thumbnail image of graphical abstract

      A multipurpose antifouling and foul-release photocatalytic coating based on ORMOSIL thin films doped with nanoflower-like Bi2WO6 is described. Irradiation with visible light of the new films immersed in water produces significant amounts of H2O2 by photocatalytic oxidation of water, and allows the degradation of (bio)organic pollutants at the outer surface of the xerogel film (see figure).

  41. Cover Pictures

    1. You have free access to this content
      Ternary Hybrid γ-Fe2O3/CrVI/Amine Oxidase Nanostructure for Electrochemical Sensing: Application for Polyamine Detection in Tumor Tissue

      Dr. Emanuela Bonaiuto, Dr. Massimiliano Magro, Dr. Davide Baratella, Dr. Petr Jakubec, Elisabetta Sconcerle, Dr. Milo Terzo, Dr. Giovanni Miotto, Dr. Alberto Macone, Prof. Enzo Agostinelli, Dr. Silvano Fasolato, Dr. Rina Venerando, Prof. Gabriella Salviulo, Dr. Ondrej Malina, Prof. Radek Zboril and Prof. Dr. Fabio Vianello

      Article first published online: 18 APR 2016 | DOI: 10.1002/chem.201601077

      Thumbnail image of graphical abstract

      A stable core-shell nanostructure constituted of dichromate onto peculiar surface active maghemite nanoparticles was produced. The hybrid nanomaterial behaves as excellent electro-catalyst for hydrogen peroxide reduction and was used for the immobilization of bovine serum amino oxidase leading to a ternary hybrid nanostructured catalyst for polyamine oxidation, which was able to discriminate tumor tissues from healthy liver in human biopsies. More information can be found in the Full Paper by F. Vianello, et al. (DOI: 10.1002/chem.201600156).

    2. You have free access to this content
      Total Synthesis and Complete Stereostructure of a Marine Macrolide Glycoside, (−)-Lyngbyaloside B

      Prof. Dr. Haruhiko Fuwa, Naoya Yamagata, Yuta Okuaki, Yuya Ogata, Asami Saito and Prof. Dr. Makoto Sasaki

      Article first published online: 18 APR 2016 | DOI: 10.1002/chem.201601249

      Thumbnail image of graphical abstract

      Stereochemical assignment of conformationally flexible, complex macrolides is still a formidable challenge for organic chemists, even though remarkable advances have been made in NMR spectroscopic techniques. Through total synthesis, the complete stereostructure of lyngbyaloside B, a complex macrolide glycoside isolated from the cyanobacterium Lyngbya sp., has now been reassigned and unambiguously established for the first time. This work illustrates the importance of chemical synthesis in the structure determination of complex macrolides. More information can be found in the Full Paper by H. Fuwa et al. (DOI: 10.1002/chem.201600341).

    3. You have free access to this content
      Understanding the Origins of Nucleophilic Hydride Reactivity of Sodium Hydride–Iodide Composite

      Zonghan Hong, Derek Yiren Ong, Dr. Subas Kumar Muduli, Dr. Pei Chui Too, Guo Hao Chan, Dr. Ya Lin Tnay, Prof. Shunsuke Chiba, Dr. Yusuke Nishiyama, Prof. Hajime Hirao and Prof. Han Sen Soo

      Article first published online: 18 APR 2016 | DOI: 10.1002/chem.201601556

      Thumbnail image of graphical abstract

      NaH, as taught in organic chemistry textbooks, is typically unsuitable as a hydridic reagent. Like the space shuttle trapped in the cage of our molecular model, NaH is unable to escape the strong ionic lattice. With the help of the NaI booster, NaH forms a novel composite that can overcome a lower energy barrier. This work explains our breakthrough in using NaH as a nucleophilic hydride and—akin to the space shuttle—boldly going where no chemist has gone before. More information can be found in the Full Paper by S. Chiba, Y. Nishiyama, H. Hirao, H. S. Soo et al. (DOI: 10.1002/chem.201600340).

  42. Full Papers

    1. Self-Assembly

      Anion-Directed Copper(II) Metallocages, Coordination Chain, and Complex Double Salt: Structures, Magnetic Properties, EPR Spectra, and Density Functional Study

      Prof. Dr. Jing-Yun Wu, Ming-Shiou Zhong, Prof. Dr. Ming-Hsi Chiang, Dr. Dibyendu Bhattacharya, Yen-Wei Lee and Prof. Dr. Long-Li Lai

      Article first published online: 15 APR 2016 | DOI: 10.1002/chem.201505215

      Thumbnail image of graphical abstract

      Supramolecular metallo-assemblies: Five anion-templated metallocages, a complex double salt, and a coordination chain were obtained by self-assembly from dpma/CuX2/HX or dpma/CuSO4/H2SO4 systems (see scheme; dpma=bis(3-pyridylmethyl)amine). Formation of the metallocages is due to the shape of the anion and coordination and hydrogen-bonding interactions of the anionic guest with the cationic {Cu2(μ-Hdpma)4} host.

    2. Ring-Opening Polymerization

      Highly Stereocontrolled Ring-Opening Polymerization of Racemic Alkyl β-Malolactonates Mediated by Yttrium [Amino-alkoxy-bis(phenolate)] Complexes

      Dr. Cédric G. Jaffredo, Dr. Yulia Chapurina, Dr. Evgueni Kirillov, Prof. Dr. Jean-François Carpentier and Dr. Sophie M. Guillaume

      Article first published online: 15 APR 2016 | DOI: 10.1002/chem.201600223

      Thumbnail image of graphical abstract

      Line them up! Highly syndioselective yttrium catalysts based on halogenated ligand platforms for the ring-opening polymerization of functional β-lactones are presented (see figure; MLA=malolactonate, where R is a allyl, benzyl, or methyl lateral ester function, PMLA=poly(β-malolactonate)).

  43. Communications

    1. Organic Chemistry

      Ligand-Promoted C(sp3)−H Olefination en Route to Multi-functionalized Pyrazoles

      Dr. Weibo Yang, Dr. Shengqing Ye, Yvonne Schmidt, Dean Stamos and Prof. Dr. Jin-Quan Yu

      Article first published online: 15 APR 2016 | DOI: 10.1002/chem.201600704

      Thumbnail image of graphical abstract

      The right moves: A pyrazole-directed C(sp3)−H olefination has been developed (see scheme). The monoprotected amino acid ligands (MPAA) are found to significantly promote the reactivity in Pd-catalyzed C(sp3)−H olefination. The applicability of using this reaction for late-stage diversification of pyrazole-based complex scaffold is demonstrated.

  44. Full Papers

    1. Microporous Materials | Hot Paper

      Copper-Free Sonogashira Coupling for High-Surface-Area Conjugated Microporous Poly(aryleneethynylene) Networks

      Matthias Trunk, Anna Herrmann, Dr. Hakan Bildirir, Dr. Ali Yassin, Dr. Johannes Schmidt and Prof. Dr. Arne Thomas

      Article first published online: 15 APR 2016 | DOI: 10.1002/chem.201600783

      Thumbnail image of graphical abstract

      A modified one-pot Sonogashira cross-coupling reaction based on a copper-free methodology has been applied for the synthesis of conjugated microporous polymers (CMPs). Not only are the resulting structures much more defined than previously published materials, but they also show far superior Brunauer–Emmett–Teller (BET) surface areas of up to 2552 m2 g−1, setting a new record for this type of materials (see scheme).

  45. Cover Pictures

    1. You have free access to this content
      Synthesis of (E)-4-Bromo-3-methoxybut-3-en-2-one, the Key Fragment in the Polyhydroxylated Chain Common to Oscillariolide and Phormidolides A–C

      Alejandro Gil, Dr. Janire Lamariano-Merketegi, Dr. Adriana Lorente, Prof. Fernando Albericio and Prof. Mercedes Álvarez

      Article first published online: 15 APR 2016 | DOI: 10.1002/chem.201601577

      Thumbnail image of graphical abstract

      Natural products are extracted from biological organisms like bacteria, fungi, marine invertebrates, plants, or animals. This cover picture shows a typical sequential cycle in which the biology and the chemistry are closely related. Phormidolides and oscillariolides are secondary metabolites isolated from marine organisms. The bromo–methoxy–diene (BMD) is a synthetically challenging motif common to all the compounds in these families. The first stereoselective synthetic approach to “fish” this complicated domain has been described and this strategy may be applied to the total synthesis of all the compounds that share this BMD moiety. More information can be found in the Communication by M. Álvarez et al. (DOI: 10.1002/chem.201600770).

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