Angewandte Chemie International Edition

Cover image for Vol. 55 Issue 20

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

Editor: Peter Gölitz, Deputy Editors: Neville Compton, Haymo Ross

Online ISSN: 1521-3773

Associated Title(s): Angewandte Chemie, Chemistry - A European Journal, Chemistry – An Asian Journal, ChemistryOpen, ChemPlusChem, Zeitschrift für Chemie


  1. 1 - 100
  2. 101 - 200
  3. 201 - 276
  1. Communications

    1. CO2 Reduction

      You have full text access to this OnlineOpen article
      Electrocatalytic and Solar-Driven CO2 Reduction to CO with a Molecular Manganese Catalyst Immobilized on Mesoporous TiO2

      Timothy E. Rosser, Dr. Christopher D. Windle and Dr. Erwin Reisner

      Article first published online: 25 APR 2016 | DOI: 10.1002/anie.201601038

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      One small step for Mn: A Mn catalyst immobilized on TiO2 gave electrocatalytic CO2 reduction with a turnover number of 112. The low overpotential of 420 mV is a result of dimerization of the catalyst on the mesoporous electrode. The heterogeneous hybrid cathode was used in a photoelectrochemical cell enabling solar-driven CO production by a photo-unstable Mn catalyst for the first time.

    2. Ion Channel Mimics

      Thermal Responsive Ion Selectivity of Uranyl Peroxide Nanocages: An Inorganic Mimic of K+ Ion Channels

      Yunyi Gao, Jennifer E. S. Szymanowski, Xinyu Sun, Prof. Dr. Peter C. Burns and Prof. Dr. Tianbo Liu

      Article first published online: 23 APR 2016 | DOI: 10.1002/anie.201601852

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      U60 clusters demonstrate tunable ion selectivity at different temperatures that can mimic the function of protein ion channels. Adjustable permeability toward different alkali ions is mainly attributed to the thermal responsiveness of the U60 cluster's hydration shell thickness.

    3. Fatty Acid Binding Proteins

      Local Unfolding of Fatty Acid Binding Protein to Allow Ligand Entry for Binding

      Tianshu Xiao, Dr. Jing-song Fan, Hu Zhou, Dr. Qingsong Lin and Prof. Daiwen Yang

      Article first published online: 23 APR 2016 | DOI: 10.1002/anie.201601326

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      Open and shut case: Fatty acid binding proteins exist mainly in a closed conformation that is in equilibrium with two minor states: one native-like and one locally unfolded. Local unfolding of the second helix generates an opening to allow ligands to enter or leave the protein cavity and controls ligand association and dissociation rates.

    4. Gold Nanorod Analysis

      Nanorod Aspect Ratios Determined by the Nano-Impact Technique

      Dr. Blake J. Plowman, Dr. Neil P. Young, Dr. Christopher Batchelor-McAuley and Prof. Richard G. Compton

      Article first published online: 23 APR 2016 | DOI: 10.1002/anie.201602867

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      Shaping up: The electrochemical determination of the aspect ratio of gold nanorods on an individual basis through nano-impact experiments is demonstrated. The measured dimensions are in excellent agreement with electron microscopy results, establishing the use of nanoparticle impact electrochemistry for the characterization of anisotropic nanomaterials.

    5. Surface Modification

      You have full text access to this OnlineOpen article
      Thermally Induced Silane Dehydrocoupling on Silicon Nanostructures

      Dr. Dokyoung Kim, Dr. Jinmyoung Joo, Dr. Youlin Pan, Alice Boarino, Yong Woong Jun, Prof. Dr. Kyo Han Ahn, Dr. Barry Arkles and Prof. Dr. Michael J. Sailor

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201601010

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      Organic trihydridosilanes were grafted to hydrogen-terminated porous Si nanostructures with no catalyst. When intrinsically photoluminescent porous Si films or nanoparticles are used, photoluminescence is retained in the grafted products, indicating that the chemistry does not introduce substantial nonradiative surface traps.

    6. High-Throughput Screening

      MALDI-MS Patterning of Caspase Activities and Its Application in the Assessment of Drug Resistance

      Junjie Hu, Fei Liu and Prof. Huangxian Ju

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201601096

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      Clearly visible: A MALDI-MS patterning strategy for the convenient visual presentation of multiple enzyme activities with an easy-to-prepare chip is proposed. The activities of various caspases and the development of drug resistance could thus be visualized.

    7. Zeolites

      Open-Pore Two-Dimensional MFI Zeolite Nanosheets for the Fabrication of Hydrocarbon-Isomer-Selective Membranes on Porous Polymer Supports

      Han Zhang, Prof. Qiang Xiao, Prof. Xianghai Guo, Prof. Najun Li, Prashant Kumar, Neel Rangnekar, Mi Young Jeon, Prof. Shaeel Al-Thabaiti, Prof. Katabathini Narasimharao, Prof. Sulaiman Nasir Basahel, Prof. Berna Topuz, Frank J. Onorato, Prof. Christopher W. Macosko, Prof. K. Andre Mkhoyan and Prof. Michael Tsapatsis

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201601135

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      The detemplation and exfoliation of multilamellar MFI nanosheets was achieved by treatment with piranha solution (H2SO4/H2O2). A film obtained by directly coating a polymer support with the nanosheets exhibited an n-butane/isobutane selectivity of approximately 5.4.

    8. Light-Emitting Diodes

      Benzimidazobenzothiazole-based Bipolar Hosts to Harvest Nearly All of the Excitons from Blue Delayed Fluorescence and Phosphorescent Organic Light-Emitting Diodes

      Lin-Song Cui, Jong Uk Kim, Hiroko Nomura, Hajime Nakanotani and Prof. Chihaya Adachi

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201601136

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      Gotta catch them all: Over 20 % external quantum efficiency were achieved in both blue thermally activated delayed fluorescence (TADF) and phosphorescent organic light-emitting diodes (OLEDs) using benzimidazobenzothiazole-bipolar host materials.

    9. Chirality

      Selective Dynamic Assembly of Disulfide Macrocyclic Helical Foldamers with Remote Communication of Handedness

      Dr. Christos Tsiamantas, Dr. Xavier de Hatten, Dr. Céline Douat, Dr. Brice Kauffmann, Dr. Victor Maurizot, Prof. Hirotaka Ihara, Dr. Makoto Takafuji, Prof. Nils Metzler-Nolte and Dr. Ivan Huc

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201601156

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      Hand signals: Remote chiral communication of handedness is conveyed between aromatic helical foldamers through disulfide-bridged side chains without any direct contact between helices.

    10. Cross-Coupling

      Intra- and Intermolecular Nickel-Catalyzed Reductive Cross-Electrophile Coupling Reactions of Benzylic Esters with Aryl Halides

      Mikhail O. Konev, Luke E. Hanna and Prof. Dr. Elizabeth R. Jarvo

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201601206

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      Crossed off: Nickel-catalyzed cross-electrophile coupling reactions of benzylic esters and aryl halides have been developed. Both inter- and intramolecular variants proceed under mild reaction conditions, and a range of heterocycles and functional groups are tolerated. Additionally, the first example of a stereospecific cross-electrophile coupling of a secondary benzylic ester is described.

    11. Carbenoid Compounds

      Alkali Metal Carbenoids: A Case of Higher Stability of the Heavier Congeners

      M. Sc. Sebastian Molitor and Priv.-Doz. Dr. Viktoria H. Gessner

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201601356

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      Heavy but stable: The reactivity of s-block metal organyl compounds generally increases when going down the group of the periodic table, often limiting applications of the heavier congeners. However, the reverse of this trend has now been demonstrated for alkali metal carbenoids by replacement of Li by Na or K. The resulting compounds exhibit an increased thermal stability, which allows their isolation and selective application.

    12. C−C coupling

      Z-Selective (Cross-)Dimerization of Terminal Alkynes Catalyzed by an Iron Complex

      Dr. Orestes Rivada-Wheelaghan, Dr. Subrata Chakraborty, Dr. Linda J. W. Shimon, Yehoshoa Ben-David and Prof. David Milstein

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201601382

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      Ironing out the kinks: Iron-catalyzed homocoupling of terminal alkynes and cross-dimerization of aryl acetylenes with a silylacetylene avoided problems of precious metal catalysis, usage of additives, and selectivity issues encountered with other catalysts in the past. The complex [Fe(H)(BH4)(iPr-PNP)] (1) operated efficiently at room temperature without a base or other additives to give the corresponding products with Z selectivity in 79–99 % yield (see scheme).

    13. siRNA delivery

      In Situ Functionalized Polymers for siRNA Delivery

      Juan M. Priegue, Daniel N. Crisan, Dr. José Martínez-Costas, Prof. Dr. Juan R. Granja, Dr. Francisco Fernandez-Trillo and Dr. Javier Montenegro

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201601441

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      Signed, sealed, delivered: The chemical functionality of a polyhydrazide scaffold was modified by careful choice of cationic (blue box; see picture) and hydrophobic (red) aldehydes to produce amphiphilic vectors for supramolecular polynucleotide delivery.

    14. Desymmetrization

      Asymmetric Induction at Remote Quaternary Centers of Cyclohexadienones by Rhodium-Catalyzed Conjugate Hydrosilylation

      Dr. Yuki Naganawa, Mayu Kawagishi, Dr. Jun-ichi Ito and Prof. Dr. Hisao Nishiyama

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201601636

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      Remote control: The catalytic asymmetric construction of a quaternary stereocenter—one of the most challenging issues in synthetic organic chemistry—was possible by the desymmetrizing conjugate hydrosilylation of prochiral differently γ,γ-disubstituted cyclohexadienones in the presence of a chiral rhodium complex (see scheme). The cyclohexenone products with a remote stereogenic quaternary center were formed with high stereoselectivity.

    15. Asymmetric Catalysis

      Base-Free Conditions for Rhodium-Catalyzed Asymmetric Arylation To Produce Stereochemically Labile α-Aryl Ketones

      Dr. Xiaowei Dou, Prof. Dr. Yixin Lu and Prof. Dr. Tamio Hayashi

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201601709

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      Forget about bases, score a home run: The asymmetric arylation of 2,2-dialkyl cyclopent-4-ene-1,3-diones with aryl boronic acids was efficiently catalyzed by a chiral diene–rhodium μ-chloro dimer without a base in toluene/H2O (see scheme). The resulting α-aryl ketones can not be obtained with high ee values under the standard basic conditions for rhodium-catalyzed asymmetric arylation owing to their racemization in the presence of a base.

    16. Optogenetics | Very Important Paper

      A Phytochrome Sensory Domain Permits Receptor Activation by Red Light

      Eva Reichhart, Dr. Alvaro Ingles-Prieto, Alexandra-Madelaine Tichy, Catherine McKenzie and Dr. Harald Janovjak

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201601736

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      Go deep with red: The sensory domain (S) of the cyanobacterial phytochrome 1 (CPH1) was repurposed to induce the homodimerization of proteins in living cells by red light. By using this domain, light-activated protein kinases were engineered that can be activated orthogonally from many fluorescent proteins and through mammalian tissue. Pr/Pfr=red-/far-red-absorbing state of CPH1.

    17. Ferric NO Complexes

      Structural and Spectroscopic Characterization of a High-Spin {FeNO}6 Complex with an Iron(IV)−NO Electronic Structure

      Amy L. Speelman, Dr. Bo Zhang, Prof. Carsten Krebs and Prof. Nicolai Lehnert

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201601742

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      One-electron oxidation of the high-spin ferrous nitrosyl complex [Fe(TMG3tren)(NO)]2+ yields a rare high-spin (S=1) ferric NO adduct ({FeNO}6). Spectroscopic investigations and DFT calculations indicate that this species has an FeIV-NO electronic structure. This finding demonstrates that high-spin non-heme iron nitrosyl complexes have fundamentally different redox behavior compared to corresponding low-spin heme systems.

    18. Halide Perovskites

      Pressure-Dependent Polymorphism and Band-Gap Tuning of Methylammonium Lead Iodide Perovskite

      Shaojie Jiang, Dr. Yanan Fang, Dr. Ruipeng Li, Dr. Hai Xiao, Jason Crowley, Dr. Chenyu Wang, Prof. Timothy J. White, Prof. William A. Goddard III, Dr. Zhongwu Wang, Dr. Tom Baikie and Prof. Jiye Fang

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201601788

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      Band aid: With a determination of methylammonium lead iodide perovskite crystallographic transitions under pressure, in situ laser-excited photoluminescence suggests a reduction in band gap in the tetragonal phase with increasing the pressure up to about 0.3 GPa and then an increase in band gap in ReO3-type cubic phase up to a pressure of 2.7 GPa, a result that is supported by DFT calculations.

    19. Suzuki–Miyaura Coupling

      Synthesis of Biaryls through Nickel-Catalyzed Suzuki–Miyaura Coupling of Amides by Carbon–Nitrogen Bond Cleavage

      Shicheng Shi, Guangrong Meng and Prof. Dr. Michal Szostak

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201601914

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      Breaking and making: The first nickel-catalyzed Suzuki–Miyaura coupling of amides for the synthesis of biaryl compounds through N−C amide bond cleavage is reported. The reaction tolerates a wide range of sensitive and electronically diverse substituents on both coupling partners.

    20. Radical Reduction

      Radical Hydrodeiodination of Aryl, Alkenyl, Alkynyl and Alkyl Iodides with an Alcoholate as Organic Chain Reductant through Electron Catalysis

      Abhishek Dewanji, Dr. Christian Mück-Lichtenfeld and Prof. Dr. Armido Studer

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201601930

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      H-donor and e-donor: Alcoholates are used as cheap radical reducing reagents for the efficient reduction of various iodides. Chains are initiated by O2 and alcoholates serve as efficient H-donors and one-electron reducing reagents in these electron-catalyzed chain reactions. Chemoselective hydrodeiodination over hydrodebromination is achieved.

    21. Nanostructures

      Controlling the Atomic Structure of Au30 Nanoclusters by a Ligand-Based Strategy

      Tatsuya Higaki, Chong Liu, Chenjie Zeng, Renxi Jin, Yuxiang Chen, Prof. Nathaniel L. Rosi and Prof. Rongchao Jin

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201601947

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      In control: Structural control of an Au30 nanocluster is realized through a strategy based on the use of the 1-adamantanethiol ligand to stabilize the metal core. The newly obtained Au30(S-Adm)18 nanocluster comprises a hexagonal-close-packed kernel protected by six dimeric Au2(SR)3 motifs. This structure is different from a previously reported Au30S(S-tBu)18 cluster that comprises a face-centered-cubic kernel.

    22. Tin Compounds

      A Tin Analogue of Carbenoid: Isolation and Reactivity of a Lithium Bis(imidazolin-2-imino)stannylenoid

      Tatsumi Ochiai, Dr. Daniel Franz, Dr. Xiao-Nan Wu, Dr. Elisabeth Irran and Prof. Dr. Shigeyoshi Inoue

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201602178

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      Ambiphilic tin(II): An elusive bis(imino)stannylenoid, a tin carbenoid analogue, was synthesized by using the highly basic imidazolin-2-imino group. Through investigations into the reactivity of the system and computational studies, the ambiphilic character of the stannylenoid was demonstrated.

    23. Lanthanides

      Pentavalent Lanthanide Compounds: Formation and Characterization of Praseodymium(V) Oxides

      Qingnan Zhang, Dr. Shu-Xian Hu, Hui Qu, Dr. Jing Su, Dr. Guanjun Wang, Jun-Bo Lu, Dr. Mohua Chen, Prof. Dr. Mingfei Zhou and Prof. Dr. Jun Li

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201602196

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      Very im-Pr-essive: Infrared spectroscopic studies and quantum chemical calculations show that PrO4 and PrO2+ oxide species involve the unprecedented PrV oxidation state. In the gas phase, species such as [(PrO)+(O2)n] and [(PrO2)+(O2)n] (n=1–7), which contain the linear PrO2+ ion are formed. These studies demonstrate that the pentavalent state is viable for lanthanide elements in a suitable coordination environment.

    24. Overall Water Splitting

      Interface Engineering of MoS2/Ni3S2 Heterostructures for Highly Enhanced Electrochemical Overall-Water-Splitting Activity

      Dr. Jian Zhang, Dr. Tao Wang, Dr. Darius Pohl, Dr. Bernd Rellinghaus, Dr. Renhao Dong, Dr. Shaohua Liu, Dr. Xiaodong Zhuang and Prof. Xinliang Feng

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201602237

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      Split happens: The preparation of novel MoS2/Ni3S2 heterostructures with abundant interfaces shows that these interfaces synergistically favor the chemisorption of hydrogen and oxygen-containing intermediates, thus leading to highly enhanced water-splitting activity. DFT calculations support these findings.

    25. Metal–Organic Frameworks

      An In Situ One-Pot Synthetic Approach towards Multivariate Zirconium MOFs

      Yujia Sun, Prof. Dr. Lixian Sun, Dr. Dawei Feng and Prof. Dr. Hong-Cai Zhou

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201602274

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      Mix and match MOFs: Porphyrinic ligands are incorporated into UiO-66 through a one-pot, thermodynamically controlled synthesis from mixed ligands (ditopic 1,4-benzenedicarboxylate or its derivatives and tetratopic tetrakis(4-carboxyphenyl)porphyrin ligands). This strategy provides a facile route to introduce multiple functionalities into stable Zr-MOFs for an extensive variety of potential applications.

    26. Nonlinear Optics

      Na2BaMQ4 (M=Ge, Sn; Q=S, Se): Infrared Nonlinear Optical Materials with Excellent Performances and that Undergo Structural Transformations

      Dr. Kui Wu, Prof. Zhihua Yang and Prof. Shilie Pan

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201602317

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      Energy doubling: Four new nonlinear optical (NLO) materials were obtained and found to crystallize in two different space groups, namely Iinline image 2d (for compound Na2BaSnS4) and R3c (Na2BaSnSe4, Na2BaGeS4, and Na2BaGeSe4), constituting a novel tetragonal to trigonal structural transformation. The optical properties of Na2BaSnS4 and Na2BaGeS4 were found to meet the key requirements for IR NLO application.

    27. Hydrogen Evolution

      Enhanced Photoexcited Carrier Separation in Oxygen-Doped ZnIn2S4 Nanosheets for Hydrogen Evolution

      Wenlong Yang, Lei Zhang, Dr. Junfeng Xie, Dr. Xiaodong Zhang, Prof. Qinghua Liu, Prof. Tao Yao, Prof. Shiqiang Wei, Prof. Qun Zhang and Prof. Yi Xie

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201602543

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      Doping control: A model of ultrathin ZnIn2S4 nanosheets with oxygen doping offers insights into the influence of oxygen doping on the separation of photogenerated electron–hole pairs and the photocatalytic activity of catalysts at the atomic level. Experimental and theoretical studies reveal that the oxygen-doped ZnIn2S4 ultrathin nanosheets have enhanced photocatalytic activity.

  2. Highlights

    1. Carbon Materials

      Silicon-Compatible Carbon-Based Micro-Supercapacitors

      Dr. Xiaodong Zhuang and Prof. Xinliang Feng

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201603040

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      CSi electronics: Recently, Simon and co-workers demonstrated silicon-wafer-supported elastic carbide-derived carbons (CDCs) films without any delamination or cracks for micro-supercapacitor application. The fabrication of these CDC films is particularly important for the practical application of micro-supercapacitors in silicon-based electronics and flexible electronics.

  3. Communications

    1. Protein Structure

      Weak and Transient Protein Interactions Determined by Solid-State NMR

      Dr. Hugh R. W. Dannatt, Michele Felletti, Dr. Stefan Jehle, Yao Wang, Prof. Lyndon Emsley, Prof. Nicholas E. Dixon, Dr. Anne Lesage and Dr. Guido Pintacuda

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201511609

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      In a spin: A solid-state NMR approach based on high magnetic fields, fast magic-angle spinning, and deuteration was used to provide chemical-shift and relaxation mapping for characterizing the transient association between two regions in a 80 kDa protein assembly, the homotetrameric ssDNA-binding protein (SSB). Comparison of the wildtype (wt) and the truncated mutant SSBΔCt led to direct verification of a mechanism of regulation of E. coli DNA metabolism.

    2. Biosynthesis

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      Heterologous Production of Fungal Maleidrides Reveals the Cryptic Cyclization Involved in their Biosynthesis

      Dr. Katherine Williams, Agnieszka J. Szwalbe, Dr. Nicholas P. Mulholland, Dr. Jason L. Vincent, Dr. Andrew M. Bailey, Prof. Christine L. Willis, Prof. Thomas J. Simpson and Prof. Russell J. Cox

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201511882

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      Ring cycle: The enzymes involved in cyclisation of the maleidride family of bioactive fungal natural products, including agnestadride A and byssochlamic acid, were identified. These previously unknown proteins show homology to ketosteroid isomerases (KI-like) and phosphatidylethanolamine-binding proteins (PEBP-like).

    3. Nanocrystal Assemblies | Hot Paper

      3D Assembly of All-Inorganic Colloidal Nanocrystals into Gels and Aerogels

      Vladimir Sayevich, Bin Cai, Albrecht Benad, Danny Haubold, Luisa Sonntag, Prof. Nikolai Gaponik, Dr. Vladimir Lesnyak and Prof. Alexander Eychmüller

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201600094

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      An assembly approach for a variety of electrostatically stabilized all-inorganic semiconductor nanocrystals is based on their linking with appropriate ions into multibranched gel networks. The resulting aerogels are highly porous monolithic structures, which preserve the quantum confinement of their building blocks.

    4. Total Synthesis

      Stereoselective Substrate-Controlled Asymmetric Syntheses of both 2,5-cis- and 2,5-trans-Tetrahydrofuranoid Oxylipids: Stereodivergent Intramolecular Amide Enolate Alkylation

      Hongjun Jang, Iljin Shin, Prof. Dr. Dongjoo Lee, Prof. Dr. Hyoungsu Kim and Prof. Dr. Deukjoon Kim

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201600637

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      Two from one: The title reaction leads to both isomers of the tetrahydrofuranoid nematocidal oxylipids in a stereodivergent fashion from a common intermediate. Each of the stereoisomers results from exploiting either chelate or nonchelate control in the reaction. PMB=para-methoxybenzyl, TIPS=triisopropylsilyl.

    5. Noble-Metal-Free Electrocatalysts

      Two-Dimensional Core-Shelled Porous Hybrids as Highly Efficient Catalysts for Oxygen Reduction Reaction

      Kai Yuan, Dr. Xiaodong Zhuang, Haiyan Fu, Dr. Gunther Brunklaus, Dr. Michael Forster, Prof. Dr. Yiwang Chen, Prof. Dr. Xinliang Feng and Prof. Dr. Ullrich Scherf

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201600850

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      Hierarchically porous MoS2/N-doped carbon hybrids were fabricated by pyrolysis of MoS2-templated microporous polymer sandwiches. The hybrids are characterized by high specific surface areas and aspect ratios and show promising oxygen reduction reaction and supercapacitor performance.

    6. Self-Assembly | Hot Paper

      Molecularly Regulated Reversible DNA Polymerization

      Dr. Niancao Chen, Xuechen Shi and Prof. Dr. Yong Wang

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201601008

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      Reversible DNA polymerization: Linear and branched DNA polymers were synthesized and decomposed using molecular triggers under physiological conditions (see picture). The polymerization mechanism is based on the well-known hybridization chain reaction.

    7. Amine–Borane Dehydropolymerization

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      The Simplest Amino-borane H2B=NH2 Trapped on a Rhodium Dimer: Pre-Catalysts for Amine-Borane Dehydropolymerization

      Amit Kumar, Nicholas A. Beattie, Dr. Sebastian D. Pike, Prof. Stuart A. Macgregor and Prof. Andrew S. Weller

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201600898

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      Bridges of boron: Mechanistic investigations show that rhodium dimers bridged by amino-borane can form by a boronium-mediated route starting from amine–borane. These types of complexes are pre-catalysts for amine-borane dehydropolymerization, suggesting a possible role for bimetallic motifs in catalysis.

    8. Biogeochemical Iron Transport

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      Photoreduction of Terrigenous Fe-Humic Substances Leads to Bioavailable Iron in Oceans

      Amir Blazevic, Ewelina Orlowska, Dr. Wolfgang Kandioller, Dr. Franz Jirsa, Prof. Dr.Dr. Bernhard K. Keppler, Dr. Myrvete Tafili-Kryeziu, Prof. Dr. Wolfgang Linert, Dr. Rudolf F. Krachler, Prof. Dr. Regina Krachler and Prof. Dr. Annette Rompel

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201600852

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      Let there be light: Terrigenous humic substances (THS) are a major transporter of iron from freshwater systems to coastal and deep waters. Their iron-binding properties are solely dependent on oxygen-containing functional groups. A major iron uptake mechanism by marine organisms in the upper-ocean is governed by photoreduction processes of Fe-THS complexes.

    9. Nanoparticles

      Size-Controlled Formation of Noble-Metal Nanoparticles in Aqueous Solution with a Thiol-Free Tripeptide

      Stefano Corra, Dr. Urszula Lewandowska, Dr. Edmondo M. Benetti and Prof. Dr. Helma Wennemers

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201510337

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      A coat of peptides: Monodisperse Pd-, Pt-, and AuNPs were formed in aqueous solution in the presence of a thiol-free tripeptide. The NPs were stable for months as a result of the formation of a compact peptidic monolayer around the metal core within which each amino acid fulfills a specific role.

    10. Chlorophyll

      Fine Tuning of Chlorophyll Spectra by Protein-Induced Ring Deformation

      Dr. Dominika Bednarczyk, Dr. Orly Dym, Dr. Vadivel Prabahar, Dr. Yoav Peleg, Douglas H. Pike and Dr. Dror Noy

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201512001

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      A change for the redder: A new crystal structure of type IIa water-soluble chlorophyll binding protein (WSCP) from cauliflower is compared to the type IIb WSCP structure. It reveals how ring deformation is exploited for red shifting the red-most chlorophyll absorption peak. A single mutation of asparagine to alanine changes the hydrogen-bonding pattern of a tryptophan residue repositioning it to perturb the planarity of the chlorophyll macrocycle.

    11. Medicinal Chemistry

      Self-Assembly of Multi-nanozymes to Mimic an Intracellular Antioxidant Defense System

      Yanyan Huang, Zhen Liu, Chaoqun Liu, Enguo Ju, Yan Zhang, Prof. Jinsong Ren and Prof. Xiaogang Qu

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201600868

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      Artificial enzyme complexes: A multi-nanozyme cooperative platform was constructed to mimic an intracellular antioxidant enzyme-based defense system and protect cells against oxidative stress (see picture). This development holds great promise for potential applications in cancer and inflammation therapy.

    12. Polymorphism

      Defect-Controlled Formation of Triclinic Na2CoP2O7 for 4 V Sodium-Ion Batteries

      Dr. Heejin Kim, Chan Sun Park, Prof. Jang Wook Choi and Prof. Yousung Jung

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201601022

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      Simple defects such as sodium deficiencies can induce the selective synthesis of triclinic Na2CoP2O7, providing an increase in energy density of more than 40 % compared to the stoichiometric polymorph that is preferentially formed under the commonly used synthesis conditions. Computational and experimental studies provide insight into the influence of the defects on phase stability.

    13. Heterogeneous Catalysis

      Controllable Hydrocarbon Formation from the Electrochemical Reduction of CO2 over Cu Nanowire Arrays

      Ming Ma, Dr. Kristina Djanashvili and Dr. Wilson A. Smith

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201601282

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      Catalytic activity: A Cu nanowire array for CO2 reduction was developed. The length and density of the Cu nanowire array could be altered by a simple electroetching method. With varying length and density of the nanowire the chemical selectivity for CO2 reduction could be systematically tuned. The results provide an experimental evidence for a nanostructure-dependent catalytic activity.

    14. Cycloaddition

      Temporary Generation of a Cyclopropyl Oxocarbenium Ion Enables Highly Diastereoselective Donor–Acceptor Cyclopropane Cycloaddition

      Juliette Sabbatani and Prof. Dr. Nuno Maulide

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201601340

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      Hide-and-seek with a dipole: A novel formal [3+2] cycloaddition of cyclopropylacetals and aldehydes was developed. This reaction affords trisubstituted tetrahydrofurans displaying three newly formed chiral centers with high diastereoselectivity. The reaction relies on the transient generation of cyclopropyl oxocarbenium ions under mild conditions and is based on the concept of temporary activation of an otherwise inert protecting group.

    15. Phosphorus Ligands

      Unexpected Reactivity of [(η5-1,2,4-tBu3C5H2)Ni(η3-P3)] towards Main Group Nucleophiles and by Reduction

      Dr. Eric Mädl, Dr. Gábor Balázs, Dr. Eugenia V. Peresypkina and Prof. Dr. Manfred Scheer

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201601775

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      Stacking the deck: The reaction of [(η5-1,2,4-tBu3C5H2)Ni(η3-P3)] with potassium leads to the formation of a realgar-like P8 ligand. Triple-decker sandwich complexes with a P3 middle deck or unprecedented bicyclic P7 ligands are formed with nucleophiles.

    16. Photochemistry

      Photoassisted Synthesis of Complex Molecular Architectures: Dearomatization of Benzenoid Arenes with Aza-o-xylylenes via an Unprecedented [2+4] Reaction Topology

      Dmitry M. Kuznetsov, Dr. Olga A. Mukhina and Prof. Dr. Andrei G. Kutateladze

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201602288

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      I'm so excited: Photoinduced dearomatization of arenes was achieved through intramolecular cycloaddition with aza-o-xylylenes generated by excited-state intramolecular proton transfer in the readily available photoprecursors. The [2+4] topology of this cycloaddition is unprecedented for photo-dearomatizations of benzenoid aromatic carbocycles and produces the novel heterocycles cyclohexadieno-oxazolidino-quinolinols.

    17. C−H Activation

      Synthesis of 2-Indolyltetrahydroquinolines by Zinc(II)-Catalyzed Intramolecular Hydroarylation-Redox Cross-Dehydrogenative Coupling of N-Propargylanilines with Indoles

      Dr. Guangzhe Li and Prof. Dr. Hiroyuki Nakamura

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201602416

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      Three C−H bonds (two sp2 and one sp3) are activated in one shot in the zinc(II)-catalyzed intramolecular hydroarylation-redox cross-dehydrogenative coupling (CDC) of propargylic anilines with indoles to give 2-indolyltetrahydroquinolines in good to high yields.

    18. Energy Storage Materials | Very Important Paper

      Dual-Doped Molybdenum Trioxide Nanowires: A Bifunctional Anode for Fiber-Shaped Asymmetric Supercapacitors and Microbial Fuel Cells

      Minghao Yu, Xinyu Cheng, Yinxiang Zeng, Zilong Wang, Prof. Yexiang Tong, Prof. Xihong Lu and Prof. Shihe Yang

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201602631

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      High-performance fiber-shaped electrodes: A strategy for dual doping with nitrogen and low-valent molybdenum atoms was used to improve the electrochemical properties of MoO3. The dual-doped MoO3 nanowires showed exceptional device performances as bifunctional anode material for both fiber-shaped asymmetric supercapacitors (ASCs) and microbial fuel cells (MFCs).

    19. Zintl Anions

      Cluster Fusion: Face-Fused Nine-Atom Deltahedral Clusters in [Sn14Ni(CO)]4−

      Luis G. Perla and Prof. Slavi C. Sevov

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201602837

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      Face-to-face: Two nine-atom clusters, each in the shape of a tricapped trigonal prism (the prismatic edges parallel to the threefold axes are shown as broken lines), are “welded” at a triangular face made of two Sn and one Ni atoms to form [Sn14Ni(CO)]4−. The “welding” is achieved by heating of an ethylenediamine solution of the known clusters [Ni@Sn9Ni(CO)]3−.

    20. CO2 Reduction

      Molybdenum–Bismuth Bimetallic Chalcogenide Nanosheets for Highly Efficient Electrocatalytic Reduction of Carbon Dioxide to Methanol

      Xiaofu Sun, Dr. Qinggong Zhu, Xinchen Kang, Prof. Dr. Huizhen Liu, Dr. Qingli Qian, Dr. Zhaofu Zhang and Prof. Dr. Buxing Han

      Article first published online: 21 APR 2016 | DOI: 10.1002/anie.201603034

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      MoBi thin: Mo-Bi bimetallic chalcogenide nanosheets were utilized as an electrocatalyst for CO2 reduction to produce methanol. The Faradaic efficiency (FE) could reach 71.2 % with a current density of 12.1 mA cm−2 in 0.5 m [Bmim]BF4 MeCN solution, which are the highest values to date.

    21. Electrochemistry

      Synthesis, Crystal Structure, and Electrochemical Properties of a Simple Magnesium Electrolyte for Magnesium/Sulfur Batteries

      Dr. Wanfei Li, Shuang Cheng, Jian Wang, Dr. Yongcai Qiu, Zhaozhao Zheng, Dr. Hongzhen Lin, Sanjay Nanda, Qian Ma, Yan Xu, Dr. Fangmin Ye, Dr. Meinan Liu, Lisha Zhou and Prof. Yuegang Zhang

      Article first published online: 20 APR 2016 | DOI: 10.1002/anie.201600256

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      Simple but effective: A simple magnesium salt [Mg(THF)6][AlCl4]2 can be used as a magnesium electrolyte that possesses a high reversible Mg cycling efficiency, good anodic stability, and good ionic conductivity. Mg/S batteries containing the electrolyte could be cycled over 20 cycles, thus indicating electrochemically reversible conversion of sulfur to MgS.

    22. Hydrogen Evolution

      Hierarchical Integration of Photosensitizing Metal–Organic Frameworks and Nickel-Containing Polyoxometalates for Efficient Visible-Light-Driven Hydrogen Evolution

      Dr. Xiang-Jian Kong, Zekai Lin, Dr. Zhi-Ming Zhang, Teng Zhang and Prof. Wenbin Lin

      Article first published online: 20 APR 2016 | DOI: 10.1002/anie.201600431

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      POM & MOF work hand in hand: A tetra-nickel-containing polyoxometalate (POM) was encapsulated into the pores of phosphorescent metal–organic frameworks (MOFs). The hierarchical POM@MOF assemblies effect highly efficient photocatalytic hydrogen evolution reactions via facile multi-electron transfer processes.

    23. Hydrogen-Evolution Reaction

      Ultrasmall Cu7S4@MoS2 Hetero-Nanoframes with Abundant Active Edge Sites for Ultrahigh-Performance Hydrogen Evolution

      Jun Xu, Jiabin Cui, Chong Guo, Zipeng Zhao, Rui Jiang, Prof. Suying Xu, Zhongbin Zhuang, Prof. Dr. Yu Huang, Prof. Dr. Leyu Wang and Prof. Dr. Yadong Li

      Article first published online: 20 APR 2016 | DOI: 10.1002/anie.201600686

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      HER donuts: Ultrasmall donut-shaped Cu7S4@MoS2 hetero-nanoframes were fabricated and served as highly efficient and stable catalysts for the hydrogen-evolution reaction (HER) because of their good crystallinity and abundant MoS2 active edge sites.

    24. Cluster Compounds

      Amphoteric Aqueous Hafnium Cluster Chemistry

      Dr. Sara Goberna-Ferrón, Deok-Hie Park, Jenn M. Amador, Prof. Douglas A. Keszler and Prof. May Nyman

      Article first published online: 20 APR 2016 | DOI: 10.1002/anie.201601134

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      Crossing the amphoteric desert: Beyond the acidic region, the chemistry of hafnium oxo-hydroxo clusters has been a barren landscape. The first hafnium polynuclear hydroxo cluster was now isolated from basic solution, and it has surprising similarities to clusters isolated on the opposite end of the pH-scale.

    25. Thermoelectrics | Very Important Paper

      Facile Surfactant-Free Synthesis of p-type SnSe Nanoplates with Exceptional Thermoelectric Power Factors

      Dr. Guang Han, Dr. Srinivas R. Popuri, Dr. Heather F. Greer, Dr. Jan-Willem G. Bos, Prof. Wuzong Zhou, Prof. Andrew R. Knox, Dr. Andrea Montecucco, Dr. Jonathan Siviter, Dr. Elena A. Man, Dr. Martin Macauley, Prof. Douglas J. Paul, Prof. Wen-guang Li, Dr. Manosh C. Paul, Dr. Min Gao, Dr. Tracy Sweet, Prof. Robert Freer, Dr. Feridoon Azough, Dr. Hasan Baig, Dr. Nazmi Sellami, Prof. Tapas K. Mallick and Prof. Duncan H. Gregory

      Article first published online: 20 APR 2016 | DOI: 10.1002/anie.201601420

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      A surfactant-free aqueous solution methodology has been developed for the straightforward synthesis of SnSe nanoplates in gram quantities, which can be hot-pressed into nanostructured compacts with much higher thermoelectric power factors than surfactant-prepared products and comparable values to bulk polycrystalline counterparts.

    26. Metallo-Borophene

      The Planar CoB18 Cluster as a Motif for Metallo-Borophenes

      Wan-Lu Li, Tian Jian, Xin Chen, Teng-Teng Chen, Dr. Gary V. Lopez, Prof. Dr. Jun Li and Prof. Dr. Lai-Sheng Wang

      Article first published online: 20 APR 2016 | DOI: 10.1002/anie.201601548

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      No bending: The CoB18 cluster was investigated experimentally and theoretically. It is found to be a highly stable and perfectly planar structure consisting of a monovalent Co atom centered in a seven-membered ring.

    27. C−H Activation

      Manganese(I)-Catalyzed Substitutive C−H Allylation

      Weiping Liu, Sven C. Richter, Yujiao Zhang and Prof. Dr. Lutz Ackermann

      Article first published online: 20 APR 2016 | DOI: 10.1002/anie.201601560

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      Manganese(I) carboxylate catalysts allow step-economical C−H allylations with broad substrate scope. The reaction proceeds through redox-neutral organometallic C(sp2)−H activation, which has the advantage of enabling the transformative late-stage diversification of functionalized molecules.

    28. Organocatalysis

      Quinine-Catalyzed Asymmetric Synthesis of 2,2′-Binaphthol-Type Biaryls under Mild Reaction Conditions

      Mauro Moliterno, Riccardo Cari, Antonio Puglisi, Achille Antenucci, Céline Sperandio, Erica Moretti, Antonio Di Sabato, Dr. Riccardo Salvio and Prof. Marco Bella

      Article first published online: 20 APR 2016 | DOI: 10.1002/anie.201601660

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      Simple is better: Commercially available reagents such as quinones and naphthols are combined under mild reaction conditions in the presence of quinine to afford halogenated 2,2′-binaphthol-like biaryls in gram quantities. The products are isolated in good yield and stereoselectivity.

    29. Nanospheres

      Synthesis of Highly Uniform Molybdenum–Glycerate Spheres and Their Conversion into Hierarchical MoS2 Hollow Nanospheres for Lithium-Ion Batteries

      Dr. Yawen Wang, Dr. Le Yu and Prof. Xiong Wen (David) Lou

      Article first published online: 20 APR 2016 | DOI: 10.1002/anie.201601673

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      Dr Mo: Hierarchical MoS2 hollow nanospheres are synthesized with a self-templating method from highly uniform Mo–glycerate solid spheres. By sulfidation and annealing, these Mo–glycerate solid spheres can be converted into hierarchical MoS2 hollow nanospheres. Owing to their unique structures, the hierarchical nanospheres show enhanced electrochemical properties as the anode material for lithium-ion batteries.

    30. Bonding Analysis

      Unusually Short Be−Be Distances with and without a Bond in Be2F2 and in the Molecular Discuses Be2B8 and Be2B7

      Dr. Zhong-hua Cui, Prof. Wen-sheng Yang, Dr. Lili Zhao, Prof. Yi-hong Ding and Prof. Gernot Frenking

      Article first published online: 20 APR 2016 | DOI: 10.1002/anie.201601890

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      Very close but not bonded: The discus-shaped molecules Be2B8 and Be2B7 possess double (6σ and 6π) aromaticity and extremely short Be–Be distances of 1.9 Å without a chemical bond between these atoms. Be2F2, on the other hand, has a Be−Be bond length of 2.05 Å and displays a record-high bond dissociation energy of 76.9 kcal mol−1.

    31. Biofilms

      Hamamelitannin Analogues that Modulate Quorum Sensing as Potentiators of Antibiotics against Staphylococcus aureus

      Arno Vermote, Dr. Gilles Brackman, Dr. Martijn D. P. Risseeuw, Bieke Vanhoutte, Prof. Dr. Paul Cos, Prof. Dr. Kristof Van Hecke, Dr. Koen Breyne, Prof. Dr. Evelyne Meyer, Prof. Dr. Tom Coenye and Prof. Dr. Serge Van Calenbergh

      Article first published online: 20 APR 2016 | DOI: 10.1002/anie.201601973

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      Don't Let the Bad Bugs Bite: Staphylococcus aureus (blue) is notorious for causing antibiotic (yellow) resistant biofilm-related infections. The discovery of hamamelitannin as an antimicrobial potentiator led to an investigation of its structure–activity relationship. A potent and metabolically stable analogue (see structure, green) was identified that shows improved activity and drug-like properties.

    32. Sustainable Chemistry

      Lactamization of sp2 C−H Bonds with CO2: Transition-Metal-Free and Redox-Neutral

      Zhen Zhang, Li-Li Liao, Si-Shun Yan, Lei Wang, Yun-Qi He, Jian-Heng Ye, Dr. Jing Li, Prof. Dr. Yong-Gang Zhi and Prof. Dr. Da-Gang Yu

      Article first published online: 20 APR 2016 | DOI: 10.1002/anie.201602095

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      CO2=CO+O: Carbon dioxide was used directly as the carbonyl source for the lactamization of alkenyl and heteroaryl C−H bonds, allowing for the synthesis of important 2-quinolinones and polyheterocycles. These transition-metal-free and redox-neutral reactions featured a broad substrate scope, good functional group tolerance, scalability, and facile product derivatization.

    33. Host–Guest Chemistry

      Peripheral Templation Generates an MII6L4 Guest-Binding Capsule

      Felix J. Rizzuto, Dr. Wen-Yuan Wu, Dr. Tanya K. Ronson and Prof. Jonathan R. Nitschke

      Article first published online: 20 APR 2016 | DOI: 10.1002/anie.201602135

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      Are you in or out? A new series of MII6L4 pseudo-octahedra can bind endo and exo guests concurrently; however, only in the presence of a peripherally bound tetraphenylborate anion do the shown subcomponents assemble to form their intended architecture. This templated structure can then encapsulate a carborate anion in its central cavity.

    34. Anions

      The 2-Arsaethynolate Anion: Synthesis and Reactivity Towards Heteroallenes

      Dr. Alexander Hinz and Prof. Dr. Jose M. Goicoechea

      Article first published online: 20 APR 2016 | DOI: 10.1002/anie.201602310

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      A look at As and Co.: Reported is the synthesis and isolation of the 2-arsaethynolate anion, AsCO, and its subsequent reactivity towards heteroallenes. Reactions with ketenes and carbodiimides afford four-membered anionic heterocycles in formal [2+2] cycloaddition reactions. By contrast, reaction with an isocyanate yielded a 1,4,2-diazaarsolidine-3,5-dionide anion and the unprecedented cluster anions As102− and As124−.

    35. Total Synthesis

      Enantioselective Total Synthesis of (−)-Terengganensine A

      Cyril Piemontesi, Dr. Qian Wang and Prof. Dr. Jieping Zhu

      Article first published online: 20 APR 2016 | DOI: 10.1002/anie.201602374

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      Simplifying complexity: A seven-step synthesis of (−)-terengganensine A was achieved featuring a) Noyori's catalytic enantioselective transfer hydrogenation of an iminium salt, b) a highly diastereoselective C7 benzoyloxylation and c) an integrated oxidative cleavage of cyclopentene/triple cyclization/hydrolysis that converts in one pot compound 2 into the natural product 1.

    36. Chemoenzymatic Synthesis

      An Enantio- and Diastereoselective Chemoenzymatic Synthesis of α-Fluoro β-Hydroxy Carboxylic Esters

      Dr. James K. Howard, Dr. Marion Müller, Prof. Alan Berry and Prof. Adam Nelson

      Article first published online: 19 APR 2016 | DOI: 10.1002/anie.201602852

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      Making high-quality building blocks: The trans-o-hydroxybenzylidene pyruvate aldolase-catalysed reaction between fluoropyruvate and many (hetero)aromatic aldehydes yield aldol adducts without subsequent dehydration. Treatment of the reaction products with hydrogen peroxide gives the corresponding syn-configured α-fluoro β-hydroxy carboxylic acids with >98 % ee.

    37. Antimalarials

      A Click Chemistry-Based Proteomic Approach Reveals that 1,2,4-Trioxolane and Artemisinin Antimalarials Share a Common Protein Alkylation Profile

      Hanafy M. Ismail, Victoria E. Barton, Matthew Panchana, Sitthivut Charoensutthivarakul, Giancarlo A. Biagini, Stephen A. Ward and Paul M. O'Neill

      Article first published online: 18 APR 2016 | DOI: 10.1002/anie.201512062

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      Clickable 1,2,4-trioxolane activity-based protein-profiling probes (ABPPs) were designed to retain antimalarial activity and alkylate the molecular targets of the blood stage of Plasmodium falciparum in situ. Comparison of the 1,2,4-trioxolane protein alkylation signature with the corresponding artemisinin ABPPs indicates that both drug classes target key proteins in the glycolytic, hemoglobin degradation, antioxidant defence and protein synthesis pathways.

    38. Ladder Polymers

      Incorporating an Alternating Donor–Acceptor Structure into a Ladder Polymer Backbone

      Kim-Julia Kass, Dr. Michael Forster and Prof. Dr. Ullrich Scherf

      Article first published online: 18 APR 2016 | DOI: 10.1002/anie.201600580

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      Up on the ladder: The donor–acceptor structure of an alternating conjugated copolymer was incorporated into a rigid ladder polymer backbone. The resulting ladder polymers show optical features typical of rigid ladder polymers, but present an increased Stokes shift corresponding to charge transfer processes during excitation, leading to a positive solvatochromism.

    39. Borylation

      You have full text access to this OnlineOpen article
      Palladium-Catalyzed Oxidative Carbocyclization–Borylation of Enallenes to Cyclobutenes

      Dr. Youai Qiu, Bin Yang, Dr. Can Zhu and Prof. Dr. Jan-E. Bäckvall

      Article first published online: 18 APR 2016 | DOI: 10.1002/anie.201601613

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      Fair and square: An efficient palladium-catalyzed oxidative borylating carbocyclization of enallenes to cyclobutene derivatives was developed. Cyclobutenes are produced as the exclusive products in MeOH in the presence of H2O with catalytic amount of Et3N, whereas the formation of alkenylboron compounds is favored in AcOH. Broad substrate scope and good tolerance for various functional groups could be achieved in both reactions.

    40. C−H Bond Functionalization

      Iron and Manganese Catalysts for the Selective Functionalization of Arene C(sp2)−H Bonds by Carbene Insertion

      Dr. Ana Conde, Gerard Sabenya, Mònica Rodríguez, Verònica Postils, Dr. Josep M. Luis, Dr. M. Mar Díaz-Requejo, Dr. Miquel Costas and Prof. Dr. Pedro J. Pérez

      Article first published online: 18 APR 2016 | DOI: 10.1002/anie.201601750

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      Exclusive catalysis: Iron- and-manganese-based catalysts selectively functionalize the C(sp2)−H bonds of benzene or alkylbenzenes through the formal insertion of the CHCO2Et group from N2CHCO2Et (see scheme). When using alkylbenzenes, the alkylic C(sp3)−H bonds of the substituents remain unmodified.

    41. Asymmetric Hydrogenation

      Chloride-Bridged Dinuclear Rhodium(III) Complexes Bearing Chiral Diphosphine Ligands: Catalyst Precursors for Asymmetric Hydrogenation of Simple Olefins

      Dr. Yusuke Kita, Shoji Hida, Kenya Higashihara, Dr. Himanshu Sekhar Jena, Kosuke Higashida and Prof. Dr. Kazushi Mashima

      Article first published online: 18 APR 2016 | DOI: 10.1002/anie.201601748

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      Dinuclear rhodium(III) complexes were highly catalytically active for asymmetric hydrogenation of simple olefins in contrast to widely utilized rhodium(I) catalytic systems.

    42. Cross-Coupling

      Iron-Catalyzed Stereoselective Cross-Coupling Reactions of Stereodefined Enol Carbamates with Grignard Reagents

      Ana Cristina Parra Rivera, Raymond Still and Prof. Doug E. Frantz

      Article first published online: 18 APR 2016 | DOI: 10.1002/anie.201601899

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      Ironing out olefin synthesis: A practical and highly stereoselective iron-catalyzed cross-coupling reaction between stereodefined enol carbamates and alkyl Grignard reagents yields tri- and tetrasubstituted acrylates. A facile method for the stereoselective generation of these enol carbamates is also reported.

    43. Organometallic Halides

      A Photoferroelectric Perovskite-Type Organometallic Halide with Exceptional Anisotropy of Bulk Photovoltaic Effects

      Dr. Zhihua Sun, Dr. Xitao Liu, Tariq Khan, Chengmin Ji, Muhammad Adnan Asghar, Dr. Sangen Zhao, Dr. Lina Li, Prof. Maochun Hong and Prof. Junhua Luo

      Article first published online: 18 APR 2016 | DOI: 10.1002/anie.201601933

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      Photoferroelectric crystals of a perovskite-type organometallic halide show highly anisotropic photovoltaic activities, including a large photocurrent and remarkable photoconductivity. The critical contribution of electric polarization is confirmed by temperature-dependent photovoltage for the first time.

    44. Solar Cells

      A Graphene Composite Material with Single Cobalt Active Sites: A Highly Efficient Counter Electrode for Dye-Sensitized Solar Cells

      Xiaoju Cui, Dr. Jianping Xiao, Dr. Yihui Wu, Peipei Du, Prof. Rui Si, Prof. Huaixin Yang, Prof. Huanfang Tian, Prof. Jianqi Li, Prof. Wen-Hua Zhang, Prof. Dehui Deng and Prof. Xinhe Bao

      Article first published online: 18 APR 2016 | DOI: 10.1002/anie.201602097

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      The incorporation of single cobalt active sites in the basal plane of graphene leads to a composite material with superior activity and stability when used as a counter electrode for the interconversion of the redox couple I/I3. DFT calculations revealed the superior properties of CoN4/GN to be due to the appropriate adsorption energy of iodine on the confined Co sites.

    45. Gas-Phase Reactions

      Thermal Activation of Methane by [HfO].+ and [XHfO]+ (X=F, Cl, Br, I) and the Origin of a Remarkable Ligand Effect

      Dr. Shaodong Zhou, Dr. Jilai Li, Dr. Maria Schlangen and Prof. Dr. Helmut Schwarz

      Article first published online: 18 APR 2016 | DOI: 10.1002/anie.201602312

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      I get by with a little help from halogens: The thermal reactions of methane with [HfO].+ and [XHfO]+ (X=F, Cl, Br, I) were investigated by using FT-ICR mass spectrometry complemented by high-level quantum chemical calculations. In contrast to the inertness of [HfO].+ towards methane (left; C gray, H blue, Hf turquoise, O red), the closed-shell oxide ions [XHfO]+ (X=F, Cl, Br) activate the H3C−H bond to form the insertion products [Hf(X)(OH)(CH3)]+ (right, X green).

    46. Na–CO2 batteries | Very Important Paper

      Rechargeable Room-Temperature Na–CO2 Batteries

      Dr. Xiaofei Hu, Jianchao Sun, Zifan Li, Qing Zhao, Chengcheng Chen and Prof. Jun Chen

      Article first published online: 18 APR 2016 | DOI: 10.1002/anie.201602504

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      Building a better battery: Developing rechargeable metal–CO2 batteries represents a “clean” strategy for advanced energy storage/conversion systems. A rechargeable room-temperature Na–CO2 battery with superior performance is reported, with the reaction of 4 Na+3 CO2⇄2 Na2CO3+C.

    47. Hydroformylation

      Rhodium-Catalyzed Desymmetrization by Hydroformylation of Cyclopentenes: Synthesis of Chiral Carbocyclic Nucleosides

      Cai You, Biao Wei, Xiuxiu Li, Yusheng Yang, Yue Liu, Prof. Dr. Hui Lv and Prof. Dr. Xumu Zhang

      Article first published online: 18 APR 2016 | DOI: 10.1002/anie.201601478

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      Efficient access: A Rh/Yanphos complex catalyzed the desymmetrization of cyclopentenes through hydroformylation, thus giving cyclopentane carboxaldehydes with good yields and excellent diastereo- and enantioselectivities. This protocol provides efficient access to chiral carbocyclic nucleosides and exhibits good application prospects in organic synthesis.

    48. Oxygen Reduction Reaction

      Theoretical Modelling and Facile Synthesis of Highly Active Boron-Doped Palladium Catalyst for the Oxygen Reduction Reaction

      Tat Thang Vo Doan, Jingbo Wang, Kee Chun Poon, Desmond C. L. Tan, Bahareh Khezri, Prof. Richard D. Webster, Prof. Haibin Su and Prof. Hirotaka Sato

      Article first published online: 18 APR 2016 | DOI: 10.1002/anie.201601727

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      Better with a B in its bonnet: Theoretical modelling shows that B doping negatively shifts the surface core level of Pd and lowers the barrier to O2 dissociation for the oxygen reduction reaction (ORR). A B-doped Pd nanoparticle catalyst was and then rationally designed, and facilely synthesized by electroless deposition and shown to be highly active ORR catalyst compared to commercial Pd and Pt catalysts.

    49. Photochemistry

      A Visible-Light-Promoted O-Glycosylation with a Thioglycoside Donor

      Mark L. Spell, Kristina Deveaux, Caitlin G. Bresnahan, Bradley L. Bernard, William Sheffield, Revati Kumar and Prof. Dr. Justin R. Ragains

      Article first published online: 18 APR 2016 | DOI: 10.1002/anie.201601566

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      Visible-light irradiation of 4-p-methoxyphenyl-3-butenylthioglucoside donors in the presence of Umemoto's reagent serves as an exceptionally mild and orthogonal approach to O-glycosylation. Alkyl- and arylthioglycosides not containing the p-methoxystyrene moiety are inert to these conditions, and evidence suggests that an intervening electron donor–acceptor complex is necessary for reactivity.

    50. Cancer Imaging

      Bioorthogonal Turn-On Probe Based on Aggregation-Induced Emission Characteristics for Cancer Cell Imaging and Ablation

      Dr. Youyong Yuan, Shidang Xu, Dr. Xiamin Cheng, Xiaolei Cai and Prof. Bin Liu

      Article first published online: 15 APR 2016 | DOI: 10.1002/anie.201601744

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      Fast and specific: A bioorthogonal turn-on probe based on a red-emissive fluorogen with aggregation-induced emission characteristics (AIEgen) was developed for cancer cell imaging and photodynamic ablation. The fluorescence is immediately turned on upon click reaction with azide-functionalized glycans on cancer cell surface.

    51. Palladium Catalysis

      Palladium-Catalyzed Intramolecular Carbene Insertion into C(sp3)−H Bonds

      Prof. Dr. Daniel Solé, Francesco Mariani, Prof. Dr. M.-Lluïsa Bennasar and Dr. Israel Fernández

      Article first published online: 15 APR 2016 | DOI: 10.1002/anie.201602020

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      Pd in action: Palladium is used to catalyze the C(sp3)−H insertion of metal carbenoids derived from α-diazoesters to form pyrrolidines through intramolecular assembly of C(sp3)−C(sp3) bonds. A reaction mechanism involving a metalation–deprotonation step instead of the usual concerted but asynchronous process is proposed.

    52. Porphyrinoids

      Aromaticity Reversal in the Lowest Excited Triplet State of Archetypical Möbius Heteroannulenic Systems

      Juwon Oh, Dr. Young Mo Sung, Woojae Kim, Dr. Shigeki Mori, Prof. Dr. Atsuhiro Osuka and Prof. Dr. Dongho Kim

      Article first published online: 15 APR 2016 | DOI: 10.1002/anie.201602083

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      Aromaticity reversal: Optical spectroscopy and quantum calculations reveal that metalated expanded porphyrins that are Möbius aromatic in the S0 state become Möbius antiaromatic in the lowest triplet (T1) state. The Möbius antiaromatic nature is indicated by characteristically weak, broad, and ill-defined spectral features in the T1 absorption spectra.

    53. Drug Delivery | Very Important Paper

      Magnetically and Near-Infrared Light-Powered Supramolecular Nanotransporters for the Remote Control of Enzymatic Reactions

      Dr. Svetlana A. Chechetka, Dr. Eiji Yuba, Prof. Kenji Kono, Dr. Masako Yudasaka, Dr. Alberto Bianco and Dr. Eijiro Miyako

      Article first published online: 15 APR 2016 | DOI: 10.1002/anie.201602453

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      Nanorobots: Magnetic nanoparticle–carbon nanohorn–liposome supramolecular nanotransporters were developed. The remotely controlled release of functional molecules contained in the nanotransporters was achieved by applying a magnetic field and near-infrared laser light. The nanotransporters enabled enzymatic reactions at target sites in cells and mice.

  4. Highlights

    1. Drug Design

      Rational Design of Proteasome Inhibitors as Antimalarial Drugs

      Dr. Camille Le Chapelain and Prof. Dr. Michael Groll

      Article first published online: 15 APR 2016 | DOI: 10.1002/anie.201602519

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      One life, two strategies: Crucial structural differences between the human and the Plasmodium falciparum proteasomes were recently identified. A combination of cryo-EM and functional characterization enabled the design of a selective antimalarial proteasome inhibitor that shows low toxicity in the host. When used with artemisinin, this ligand offers a new approach for efficient treatment of malaria at all stages of the parasite lifecycle.

  5. Communications

    1. Gene Editing

      A Powerful CRISPR/Cas9-Based Method for Targeted Transcriptional Activation

      M. Sc. Shota Katayama, Dr. Tetsuo Moriguchi, Dr. Naoki Ohtsu and Prof. Toru Kondo

      Article first published online: 15 APR 2016 | DOI: 10.1002/anie.201601708

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      Epigenome Editing: A novel CRISPR/Cas9-based method for transcriptional activation through microhomology-mediated end-joining (MMEJ) was developed. CRISPR/Cas9 was used to specifically replace the methylated promotor region of a target gene with an unmethylated copy, thereby leading to efficient gene activation at levels sufficient to bring about changes in cell fate.

    2. Catalyst Design

      The Influence of Elastic Strain on Catalytic Activity in the Hydrogen Evolution Reaction

      Dr. Kai Yan, Dr. Tuhina Adit Maark, Alireza Khorshidi, Dr. Vijay A. Sethuraman, Prof. Dr. Andrew A. Peterson and Prof. Dr. Pradeep R. Guduru

      Article first published online: 15 APR 2016 | DOI: 10.1002/anie.201508613

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      Strain-tuned catalysis: Elastic strain affects catalytic reaction rates, but is often coupled with a ligand effect. To isolate the strain effect, three thin metal films on elastic substrates were subjected to uniaxial loading and unloading, and investigated for their activity in the hydrogen evolution reaction.

    3. Alkenes

      Reductive Cross-Coupling of Conjugated Arylalkenes and Aryl Bromides with Hydrosilanes by Cooperative Palladium/Copper Catalysis

      Dr. Kazuhiko Semba, Kenta Ariyama, Dr. Hong Zheng, Ryohei Kameyama, Prof. Dr. Shigeyoshi Sakaki and Prof. Dr. Yoshiaki Nakao

      Article first published online: 15 APR 2016 | DOI: 10.1002/anie.201511975

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      Forming a Co-op: A method for the reductive cross-coupling of conjugated arylalkenes or internal alkynes and aryl bromides with hydrosilanes using cooperative palladium/copper catalysis was developed. The resulting 1,1-diarylalkanes and trisubstituted alkenes were isolated with high regio- and stereoselectivity. Under the applied reaction conditions, high levels of functional-group tolerance were observed.

    4. Cycloaddition

      Phosphine-mediated Highly Enantioselective Spirocyclization with Ketimines as Substrates

      Dr. Xiaoyu Han, Wai-Lun Chan, Dr. Weijun Yao, Dr. Yongjiang Wang and Prof. Dr. Yixin Lu

      Article first published online: 15 APR 2016 | DOI: 10.1002/anie.201600453

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      Like a circle in a spiral: A highly enantioselective [3+2] cycloaddition reaction that makes use of isatin-derived ketimines as reaction partners was developed. Both simple and γ-substituted allenoates could be utilized, and various 3,2′-pyrrolidinyl spirooxindoles with a tetrasubstituted stereocenter were obtained in excellent yields and with nearly perfect enantioselectivity (>98 % ee in all cases).

    5. ADP-ribosylation

      Bioorthogonally Functionalized NAD+ Analogues for In-Cell Visualization of Poly(ADP-Ribose) Formation

      Sarah Wallrodt, Annette Buntz, Dr. Yan Wang, Prof. Dr. Andreas Zumbusch and Prof. Dr. Andreas Marx

      Article first published online: 15 APR 2016 | DOI: 10.1002/anie.201600464

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      Now you see it: NAD+ is metabolized and built into poly(ADP-ribose) by ADP-ribosyltransferases, and this PARylation affects various biological processes. Methods for the intracellular visualization of this process are rare and limited. To overcome this, new NAD+ analogues functionalized with bioorthogonal reporter groups were developed and successfully applied to the selective two-color labeling of poly(ADP-ribose) formation in cells.

    6. Lithium-Ion Batteries

      A Sulfur Heterocyclic Quinone Cathode and a Multifunctional Binder for a High-Performance Rechargeable Lithium-Ion Battery

      Dr. Ting Ma, Dr. Qing Zhao, Dr. Jianbin Wang, Dr. Zeng Pan and Prof. Jun Chen

      Article first published online: 15 APR 2016 | DOI: 10.1002/anie.201601119

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      A noncovalent interaction: A sulfur heterocyclic quinone compound (DTT) and a multifunctional binder (PEDOT:PSS) were prepared and used together as a high-performance cathode in a rechargeable lithium-ion battery (see picture). Through a noncovalent interaction between DTT and PEDOT:PSS the dissolution of DTT into an electrolyte was reduced and the conductivity of DTT was enhanced.

    7. Coordination Chemistry

      Ultrafine Metal–Organic Right Square Prism-Shaped Nanowires

      Ken-ichi Otake, Dr. Kazuya Otsubo, Dr. Kunihisa Sugimoto, Prof. Akihiko Fujiwara and Prof. Hiroshi Kitagawa

      Article first published online: 15 APR 2016 | DOI: 10.1002/anie.201601678

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      A homometallic platinum nanowire was obtained through oxidative polymerization of square units. Three kinds of isostructral Pd/Pt heterometallic nanowires were also obtained by coordination-driven self-assembly of two mononuclear units. The electronic state of these nanowires can be widely controlled by substitution of metal and halide species.

    8. Asymmetric Catalysis

      Asymmetric Conjugate Addition of Benzofuran-2-ones to Alkyl 2-Phthalimidoacrylates: Modeling Structure–Stereoselectivity Relationships With Steric and Electronic Parameters

      Chen Yang, En-Ge Zhang, Prof. Xin Li and Prof. Jin-Pei Cheng

      Article first published online: 15 APR 2016 | DOI: 10.1002/anie.201601028

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      A predictive model to correlate the steric and electronic parameters of tertiary amine thiourea catalysts with the stereoselectivity of the title reaction is described. As predicted, 3,5-bis(trifluoromethyl)benzyl- and methyl-substituted tertiary amine thioureas turned out to be highly suitable catalysts.

    9. Droplet Microfluidics | Hot Paper

      Quantitative Single-Cell mRNA Analysis in Hydrogel Beads

      Agata Rakszewska, Rosa J. Stolper, Anna B. Kolasa, Dr. Aigars Piruska and Prof. Dr. Wilhelm T. S. Huck

      Article first published online: 14 APR 2016 | DOI: 10.1002/anie.201601969

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      Catch me if you can: Hydrogel beads functionalized with LNA (locked nucleic acid) can serve as a matrix to capture mRNA from lysed single cells. mRNA quantification free of pre-amplification bias is ensured by using padlock probes and rolling circle amplification followed by hybridization with fluorescent probes. The number of transcripts in individual cells is assessed by counting fluorescent dots inside gel beads. Scale bar=50 µm.

    10. Imaging Agents

      Nanotexaphyrin: One-Pot Synthesis of a Manganese Texaphyrin-Phospholipid Nanoparticle for Magnetic Resonance Imaging

      Joseph M. Keca, Juan Chen, Marta Overchuk, Nidal Muhanna, Christina M. MacLaughlin, Cheng S. Jin, Warren D. Foltz, Jonathan C. Irish and Prof. Dr. Gang Zheng

      Article first published online: 13 APR 2016 | DOI: 10.1002/anie.201600234

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      Contrast and compare: A one-pot synthesis and self-assembly method is described for preparation of Mn-texaphyrin-phospholipids, allowing facile self-assembly of Mn-nanotexaphyrins. Each Mn-nanotexaphyrin constitutes a stable 1:1 porphyrin:metal chelation, equating to 8×104 MnII ions. The newly prepared contrast agent was applied to magnetic resonance imaging (MRI) of lymphatic metastasis drainage, revealing drainage from the tumor site to the adjacent metastatic lymph node.

    11. Flexible OLED

      Versatile p-Type Chemical Doping to Achieve Ideal Flexible Graphene Electrodes

      Dr. Tae-Hee Han, Sung-Joo Kwon, Dr. Nannan Li, Hong-Kyu Seo, Dr. Wentao Xu, Prof. Kwang S. Kim and Prof. Tae-Woo Lee

      Article first published online: 13 APR 2016 | DOI: 10.1002/anie.201600414

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      Anodic optimization: p-Type chemical doping of graphene with trifluoromethanesulfonic acid (TFMS) leads to a flexible graphene anode with 70 % reduced sheet resistance and 0.83 eV increased surface work function with excellent air-stability. An OLED with TFMS-doped graphene anode exhibited lower operating voltage and higher efficiency than those with conventional ITO anode.

    12. Ruthenium Catalysis | Very Important Paper

      (Enantio)selective Hydrogen Autotransfer: Ruthenium-Catalyzed Synthesis of Oxazolidin-2-ones from Urea and Diols

      Dr. Miguel Peña-López, Dr. Helfried Neumann and Prof. Dr. Matthias Beller

      Article first published online: 13 APR 2016 | DOI: 10.1002/anie.201600698

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      Oxazolidin-2-ones were synthesized from vicinal diols and urea or carbamates in a ruthenium-catalyzed process. The sequential formation of one C−O and one C−N bond takes place in a highly chemo- and regioselective, atom-efficient domino process, which can be rendered enantioselective when an appropriate chiral ligand is used.

    13. Polyketides

      Oxidative trans to cis Isomerization of Olefins in Polyketide Biosynthesis

      Dr. Tsuyoshi Yamamoto, Dr. Yuta Tsunematsu, Dr. Kodai Hara, Dr. Tomohiro Suzuki, Dr. Shinji Kishimoto, Prof. Dr. Hirokazu Kawagishi, Prof. Dr. Hiroshi Noguchi, Prof. Dr. Hiroshi Hashimoto, Prof. Dr. Yi Tang, Prof. Dr. Kinya Hotta and Prof. Dr. Kenji Watanabe

      Article first published online: 13 APR 2016 | DOI: 10.1002/anie.201600940

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      Strike a ‘PsoE‘: An in vitro study revealed that the glutathione S-transferase PsoE required the bifunctional PsoF to complete the isomerization of a pseurotin biosynthetic pathway intermediate. The PsoE crystal structure indicated that the intermediate–glutathione conjugation to be the sole function of PsoE. PsoF was identified to have an additional oxidative isomerase activity, thus making it a trifunctional enzyme which is key to generating complexity in pseurotin biosynthesis.

    14. Iron–Oxygen Species | Hot Paper

      Exceedingly Fast Oxygen Atom Transfer to Olefins via a Catalytically Competent Nonheme Iron Species

      Joan Serrano-Plana, Dr. Almudena Aguinaco, Dr. Raquel Belda, Dr. Enrique García-España, Dr. Manuel G. Basallote, Dr. Anna Company and Dr. Miquel Costas

      Article first published online: 13 APR 2016 | DOI: 10.1002/anie.201601396

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      A metastable nonheme iron–oxygen species undergoes exceedingly fast oxygen atom transfer (OAT) to olefins, providing epoxides with stereoretention. The reaction rates determined by stopped-flow UV/Vis analysis are in good agreement with the relative reactivities of different olefins, confirming that this compound is a competent OAT intermediate of relevance to nonheme iron catalyzed epoxidations.

    15. Chlorophyll

      You have full text access to this OnlineOpen article
      On the Exciton Coupling between Two Chlorophyll Pigments in the Absence of a Protein Environment: Intrinsic Effects Revealed by Theory and Experiment

      Dr. Bruce F. Milne, Christina Kjær, Jørgen Houmøller, Dr. Mark H. Stockett, Dr. Yoni Toker, Prof. Angel Rubio and Prof. Steen Brøndsted Nielsen

      Article first published online: 13 APR 2016 | DOI: 10.1002/anie.201601979

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      How strong is the coupling between two adjacent chlorophyll molecules in the absence of a protein environment? Mass spectrometry experiments now provide an answer to this question as chlorophyll a dimers tagged by quaternary ammonium ions could be produced in the gas phase by electrospray ionization.

    16. Protic Ionic Liquids

      A pH Scale for the Protic Ionic Liquid Ethylammonium Nitrate

      Prof. Ryo Kanzaki, Prof. Hitoshi Kodamatani, Prof. Takashi Tomiyasu, Hikari Watanabe and Prof. Yasuhiro Umebayashi

      Article first published online: 13 APR 2016 | DOI: 10.1002/anie.201511328

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      Tipping the pH scale: By using potentiometric acid–base titrations, a pH scale applicable to the protic ionic liquid ethylammonium nitrate (EAN) was determined. This water-based pH scale can be employed to directly compare the differences in H+ activity between EAN and water. For example, the H+ activity in the neutral EAN corresponds to the aqueous solution with pH=4.

    17. Hierarchical Nanoparticles

      Solution-Based Fabrication of Narrow-Disperse ABC Three-Segment and Θ-Shaped Nanoparticles

      Zhen Zhang, Changming Zhou, Haiyan Dong and Daoyong Chen

      Article first published online: 13 APR 2016 | DOI: 10.1002/anie.201511768

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      As easy as ABC: Narrow-disperse ABC three-segment hierarchical nanostructured polymeric nanoparticles (HNPs) with a size of tens of nm were prepared through solution-based hierarchical self-assembly of an A-b-B-b-C triblock copolymer. Further self-assembly of the ABC HNPs resulted in narrow-disperse NPs with a Θ-like morphology.

    18. Aggregation-Induced Emission | Very Important Paper

      Structure-Dependent cis/trans Isomerization of Tetraphenylethene Derivatives: Consequences for Aggregation-Induced Emission

      Dr. Chong-Jing Zhang, Dr. Guangxue Feng, Shidang Xu, Dr. Zhenshu Zhu, Prof. Dr. Xianmao Lu, Dr. Jien Wu and Prof. Dr. Bin Liu

      Article first published online: 13 APR 2016 | DOI: 10.1002/anie.201600244

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      The cis and trans isomers of a tetraphenylethene derivative with aggregation-induced emission, TPETH-MAL, were characterized by HPLC analysis and NMR spectroscopy. cis-TPETH-MAL emits yellow fluorescence in DMSO at −20 °C whereas trans-TPETH-MAL shows red fluorescence under the same conditions.


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