Angewandte Chemie International Edition

Cover image for Vol. 56 Issue 39

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, ChemPhotoChem, ChemPlusChem, Zeitschrift für Chemie

  1. Communications

    1. Dispersion Interactions

      Intramolecular π–π Interactions in Flexibly Linked Partially Fluorinated Bisarenes in the Gas Phase

      Dr. Sebastian Blomeyer, Marvin Linnemannstöns, Jan Hendrick Nissen, Jannik Paulus, Beate Neumann, Dr. Hans-Georg Stammler and Prof. Dr. Norbert W. Mitzel

      Version of Record online: 19 SEP 2017 | DOI: 10.1002/anie.201707716

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      Undistorted structures of compounds with C6H6 and C6F6 groups linked by (CH2)3 and (CH2)2SiMe2 moieties show folding by intramolecular dispersion forces in the gas phase whereas in the solid state, extended conformers are adopted that interact intermolecularly. The experimental data served as a reference for the quality of quantum-chemical calculations.

    2. Plasma Chemistry

      One-Step Reforming of CO2 and CH4 into High-Value Liquid Chemicals and Fuels at Room Temperature by Plasma-Driven Catalysis

      Dr. Li Wang, Dr. Yanhui Yi, Dr. Chunfei Wu, Prof. Hongchen Guo and Dr. Xin Tu

      Version of Record online: 19 SEP 2017 | DOI: 10.1002/anie.201707131

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      Liquid fuels and chemicals (e.g., acetic acid, methanol, ethanol, and formaldehyde) were synthesized in a one-step process from CO2 and CH4 at room temperature (30 °C) and atmospheric pressure for the first time by using a novel plasma reactor with a water electrode. The total selectivity to oxygenates was approximately 50–60 %, with acetic acid as the major component.

    3. Heterocycles

      Alkynyl Thioethers in Gold-Catalyzed Annulations to form Oxazoles

      Dr. Raju Jannapu Reddy, Matthew P. Ball-Jones and Dr. Paul W. Davies

      Version of Record online: 19 SEP 2017 | DOI: 10.1002/anie.201706850

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      Taking a different path: The first gold-catalyzed annulations with alkynyl thioethers are reported. This transformation provides ready and convergent access into densely-functionalized 1,3-oxazole motifs. The sulfur substituent is integral to accessing the desired reactivity and provides a useful synthetic handle for later elaboration. In contrast with recent reports, the reaction does not follow a ketenethionium pathway.

    4. Radical Reactions

      Radical Hydrodehalogenation of Aryl Bromides and Chlorides with Sodium Hydride and 1,4-Dioxane

      Tobias Hokamp, Dr. Abhishek Dewanji, Maximilian Lübbesmeyer, Dr. Christian Mück-Lichtenfeld, Prof. Dr. Ernst-Ulrich Würthwein and Prof. Dr. Armido Studer

      Version of Record online: 19 SEP 2017 | DOI: 10.1002/anie.201706534

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      It is the combo! NaH in combination with 1,4-dioxane serves as the reagent for the radical chain reduction of various aryl halides. Hydrodehalogenation is initiated by 1,10-phenanthroline (phen) at elevated temperature and can be combined with a typical radical cyclization reaction. the reactions proceed via electron catalysis.

    5. Silylation

      Iron-Catalyzed anti-Selective Carbosilylation of Internal Alkynes

      Takahiro Iwamoto, Tatsushi Nishikori, Naohisa Nakagawa, Hikaru Takaya and Masaharu Nakamura

      Version of Record online: 19 SEP 2017 | DOI: 10.1002/anie.201706333

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      Pin on: anti-Selective carbosilylation of internal alkynes with PhMe2SiBpin and alkyl halides was achieved using a FeBr2/dppe catalyst system. The reaction exhibits high anti selectivity irrespective of the structure of the alkyne and electrophile. Additionally, syn-selective carbosilylation was achieved using Ph2(MeO)SiBpin. The oxygen functional group plays a key role in the syn selectivity.

    6. Ionic Liquids

      Preorganization and Cooperation for Highly Efficient and Reversible Capture of Low-Concentration CO2 by Ionic Liquids

      Yanjie Huang, Dr. Guokai Cui, Dr. Yuling Zhao, Dr. Huiyong Wang, Zhiyong Li, Prof. Sheng Dai and Prof. Jianji Wang

      Version of Record online: 19 SEP 2017 | DOI: 10.1002/anie.201706280

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      Two for one: A novel preorganization and cooperation strategy has been designed for a superior capacity (22 wt %, 1.65 mol mol−1) to capture low-concentration CO2 (10 vol. % CO2 in N2) by imide-based ionic liquids with excellent reversibility (16 cycles). Multiple-site cooperative interactions between CO2 and active sites in the preorganized anion are operative.

    7. Ferrocene

      Protonation of Ferrocene: A Low-Temperature X-ray Diffraction Study of [Cp2FeH](PF6) Reveals an Iron-Bound Hydrido Ligand

      Dr. Moritz Malischewski, Prof. Dr. Konrad Seppelt, Dr. Jörg Sutter, Dr. Frank W. Heinemann, Priv.-Doz. Dr. Birger Dittrich and Prof. Dr. Karsten Meyer

      Version of Record online: 19 SEP 2017 | DOI: 10.1002/anie.201704854

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      After more than 50 years, the mechanism of electrophilic substitutions on ferrocene was reinvestigated for the simplest electrophile, H+, and the potential intermediate [Cp2FeH]+ was isolated. Single crystals of [Cp2FeH](PF6) were obtained from an anhydrous HF/PF5 system. X-ray diffraction analysis revealed a non-agostic structure with an iron-bound hydrido ligand.

    8. C−H Activation

      Meta-Selective C−H Borylation of Benzylamine, Phenethylamine and Phenylpropylamine-Derived Amides Enabled by a Single Anionic Ligand

      Holly J. Davis, Georgi R. Genov and Dr. Robert J. Phipps

      Version of Record online: 19 SEP 2017 | DOI: 10.1002/anie.201708967

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      Clever positioning: A bipyridine ligand incorporating a remote anionic sulfonate group directs iridium-catalyzed borylation to the meta-position on a range of amide-containing arenes. It is proposed that this selectivity is a result of a hydrogen bonding interaction to correctly position the iridium metal centre in the crucial C−H activation.

    9. NMR Spectroscopy

      Fluorine Pseudocontact Shifts Used for Characterizing the Protein–Ligand Interaction Mode in the Limit of NMR Intermediate Exchange

      Dr. Jia Gao, E Liang, Dr. Rongsheng Ma, Dr. Fudong Li, Dr. Yixiang Liu, Jiuyang Liu, Prof. Dr. Ling Jiang, Prof. Dr. Conggang Li, Prof. Dr. Haiming Dai, Prof. Jihui Wu, Xuncheng Su, Prof. Dr. Wei He and Prof. Dr. Ke Ruan

      Version of Record online: 19 SEP 2017 | DOI: 10.1002/anie.201707114

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      The severe line broadening in the intermediate exchange limits the applicability of NMR spectroscopy for interrogating the interaction modes of lead-like inhibitors with moderate affinities to target proteins. A 19F chemical exchange saturation transfer approach is used to retrieve the low-populated bound-state 19F pseudocontact shifts, which enable the identification of the best binding pose of the BRM bromodomain inhibitor.

    10. Organic Electronics | Hot Paper

      Constructing a Strongly Absorbing Low-Bandgap Polymer Acceptor for High-Performance All-Polymer Solar Cells

      Zhi-Guo Zhang, Yankang Yang, Jia Yao, Lingwei Xue, Shanshan Chen, Xiaojun Li, William Morrison, Changduk Yang and Yongfang Li

      Version of Record online: 19 SEP 2017 | DOI: 10.1002/anie.201707678

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      Energy conversion: Embedding an acceptor–donor–acceptor-structured organic semiconductor building block into a polymer main chain creates an excellent low-band-gap polymer acceptor with red-shifted absorption and high absorption coefficient. The polymer acceptor provides a record-high power conversion efficiency of 9.19 % for all-polymer solar cells.

    11. Gene Delivery | Very Important Paper

      Polyamine-Mediated Stoichiometric Assembly of Ribonucleoproteins for Enhanced mRNA Delivery

      Jiahe Li, Yanpu He, Wade Wang, Connie Wu, Celestine Hong and Paula T. Hammond

      Version of Record online: 19 SEP 2017 | DOI: 10.1002/anie.201707466

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      Although numerous carriers have been developed for mRNA delivery, the inefficient mRNA expression inside cells remains a major challenge. Inspired by the dependence of mRNA on 3′-terminal polyadenosine nucleotides (poly A) and poly A binding proteins (PABPs) for optimal expression, synthetic mRNA containing a poly A tail was complexed with PABPs in a stoichiometric manner.

    12. Biosensors

      Peroxidyme-Amplified Radical Chain Reaction (PARCR): Visible Detection of a Catalytic Reporter

      John P. Goertz and Ian M. White

      Version of Record online: 19 SEP 2017 | DOI: 10.1002/anie.201706163

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      A weakness becomes an asset: The oxidative activity of catalytic nucleic acids in tandem with the much-maligned photosensitivity of the phenoxazine dye Amplex Red is leveraged to engineer an exponentially propagating reaction which creates a visible readout via multiple positive-feedback loops. This novel assay enables visible detection of the catalytic reporter from 1 μm to 100 pm.

    13. Cellular Imaging

      Conjugated Polymer with Intrinsic Alkyne Units for Synergistically Enhanced Raman Imaging in Living Cells

      Dr. Shengliang Li, Dr. Tao Chen, Dr. Yunxia Wang, Dr. Libing Liu, Dr. Fengting Lv, Dr. Zhiliang Li, Prof. Yanyi Huang, Prof. Kirk S. Schanze and Prof. Shu Wang

      Version of Record online: 19 SEP 2017 | DOI: 10.1002/anie.201707042

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      Cell watching: Cationic poly(phenylene ethynylene) (PPE) derivatives are explored for use as Raman probes for living cell imaging due to a synergetic-enhancement effect of alkyne vibrations in Raman-silent regions. The enhanced alkyne signals result from the integration of alkyne groups into the rigid polymer backbone. PPE-based conjugated polymer nanoparticles were also prepared as Raman-responsive nanomaterials for distinct imaging application.

    14. Diazo Compounds

      Catalytic Enantioselective Synthesis of Highly Functionalized Difluoromethylated Cyclopropanes

      Dr. Maxence Bos, Wei-Sheng Huang, Dr. Thomas Poisson, Prof. Dr. Xavier Pannecoucke, Prof. Dr. André B. Charette and Prof. Dr. Philippe Jubault

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201707375

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      Small rings: The first catalytic asymmetric synthesis of difluorinated cyclopropanes is described. The methodology employs a rhodium catalyst and affords access to functionalized cyclopropanes in high yields with high diastereo- and enantioselectivities. PMP=para-methoxyphenyl.

    15. Inhibitors

      Discovery of a Novel Inhibitor of the Hedgehog Signaling Pathway through Cell-based Compound Discovery and Target Prediction

      M. Sc. Lea Kremer, Dr. Carsten Schultz-Fademrecht, Dr. Matthias Baumann, Dr. Peter Habenberger, Dr. Axel Choidas, Dr. Bert Klebl, Dr. Susanne Kordes, Prof. Dr. Hans R. Schöler, Dr. Jared Sterneckert, Dr. Slava Ziegler, Prof. Gisbert Schneider and Prof. Dr. Herbert Waldmann

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201707394

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      Better together: Joint application of chemical biology and computational target prediction enabled the identification of the pyrazolo-imidazole derivative smoothib as a novel inhibitor of hedgehog signaling and the membrane protein smoothened as its target.

    16. Bioorganic Chemistry | Hot Paper

      Osmium-Mediated Transformation of 4-Thiouridine to Cytidine as Key To Study RNA Dynamics by Sequencing

      Christian Riml, Dr. Thomas Amort, Dr. Dietmar Rieder, Catherina Gasser, Prof. Alexandra Lusser and Prof. Ronald Micura

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201707465

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      RNA modification: The osmium-mediated conversion of thiouridine (4sU) to cytidine (C) is a so far disregarded reaction with great potential for comparative sequencing approaches.

    17. Porphyrinoids

      Conformationally Flexible Bis(9-fluorenylidene)porphyrin Diradicaloids

      Hejian Zhang, Dr. Hoa Phan, Dr. Tun Seng Herng, Dr. Tullimilli Y. Gopalakrishna, Dr. Wangdong Zeng, Prof. Jun Ding and Prof. Jishan Wu

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201707480

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      Protonation with a twist! A quinoidal bis(9-fluorenylidene)porphyrin and its NiII complex showed closed-shell saddle-shaped geometry in the crystalline state but they can be thermally populated to paramagnetic triplet species through geometric change. Protonation also dramatically changes the conformation and physical properties.

    18. Organic Semiconductors

      4,5,9,10-Pyrene Diimides: A Family of Aromatic Diimides Exhibiting High Electron Mobility and Two-Photon Excited Emission

      Ze-Hua Wu, Zhuo-Ting Huang, Rui-Xue Guo, Dr. Chun-Lin Sun, Li-Chuan Chen, Bing Sun, Prof. Zi-Fa Shi, Prof. Xiangfeng Shao, Prof. Hanying Li and Prof. Hao-Li Zhang

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201707529

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      Conductive and emissive: Facile synthetic routes to reach the K-region of pyrene and produce 4,5,9,10-pyrene diimide (PyDI) derivatives are reported. The PyDI derivatives exhibited efficient electron transport properties, with the highest electron mobility of up to 3.08 cm2 V−1 s−1. The tert-butyl-substituted compounds (t-PyDI) also showed good one- and two-photon excited fluorescence properties.

    19. Heterogeneous Catalysis

      Tuning the Structure of Platinum Particles on Ceria In Situ for Enhancing the Catalytic Performance of Exhaust Gas Catalysts

      Andreas M. Gänzler, Dr. Maria Casapu, Dr. Philippe Vernoux, Dr. Stéphane Loridant, Dr. Francisco J. Cadete Santos Aires, Dr. Thierry Epicier, Benjamin Betz, Dr. Rüdiger Hoyer and Prof. Dr. Jan-Dierk Grunwaldt

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201707842

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      Under control: The low temperature oxidation activity of diesel oxidation catalysts was improved by unraveling the dynamic structural behavior of Pt nanoparticles on ceria using operando X-ray absorption spectroscopy (XAS) and environmental transmission electron microscopy (ETEM). This led to a general concept to finely adjust the size and structure of noble metal particles on strongly interacting supports during real operation.

    20. Cheminformatics

      Discovery of Key Physicochemical, Structural, and Spatial Properties of RNA-Targeted Bioactive Ligands

      Brittany S. Morgan, Jordan E. Forte, Rebecca N. Culver, Dr. Yuqi Zhang and Prof. Dr. Amanda E. Hargrove

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201707641

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      A space for RNA: The curation and analysis of the RNA-targeted BIoactive ligaNd Database (R-BIND) uncovered distinguishing 2D and 3D molecular properties that support the existence of an RNA-privileged chemical space. These guiding principles can facilitate the future design of selective ligands targeted toward therapeutically relevant RNAs.

  2. Author Profile

    1. Sensuke Ogoshi

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201708270

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  3. Communications

    1. Computational Chemistry

      Heavy-Atom Tunneling Calculations in Thirteen Organic Reactions: Tunneling Contributions are Substantial, and Bell's Formula Closely Approximates Multidimensional Tunneling at ≥250 K

      Dr. Charles Doubleday, Randy Armas, Dana Walker, Christopher V. Cosgriff and Dr. Edyta M. Greer

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201708489

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      Several common reaction types were studied to assess the importance of heavy-atom tunneling in organic reactions. The results are consistent with the hypothesis that heavy-atom tunneling is widespread. The success of Bell's formula suggests it is a useful first choice for predicting transmission coefficients in heavy-atom tunnelling.

  4. Author Profile

    1. Chan Beum Park

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201709297

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  5. Communications

    1. Photomagnetic Materials

      Octacyanidotungstate(IV) Coordination Chains Demonstrate a Light-Induced Excited Spin State Trapping Behavior and Magnetic Exchange Photoswitching

      Michał Magott, Dr. Olaf Stefańczyk, Prof. Barbara Sieklucka and Dr. Dawid Pinkowicz

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201703934

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      Let it shine! Octacyanidotungstate(IV) demonstrates a light-induced excited spin state trapping photomagnetic effect that can be used to produce very strong magnetic exchange photoswitching functionality in various bimetallic coordination polymers.

    2. Mass Spectrometrie

      Native Desorption Electrospray Ionization Liberates Soluble and Membrane Protein Complexes from Surfaces

      Stephen Ambrose, Nicholas G. Housden, Kallol Gupta, Jieyuan Fan, Paul White, Hsin-Yung Yen, Julien Marcoux, Colin Kleanthous, Jonathan T. S. Hopper and Carol V. Robinson

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201704849

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      Folded soluble and membrane proteins can be released directly from surfaces using a desorption electrospray ionization source coupled to a high-resolution mass spectrometer. Desorbed protein complexes maintain non-covalent interactions enabling rapid measurement of subunit stoichiometries and capturing specific ligand binding to a GPCR.

    3. Photocatalysis | Hot Paper

      Optimizing Optical Absorption, Exciton Dissociation, and Charge Transfer of a Polymeric Carbon Nitride with Ultrahigh Solar Hydrogen Production Activity

      Dr. Guigang Zhang, Guosheng Li, Zhi-An Lan, Lihua Lin, Dr. Aleksandr Savateev, Dr. Tobias Heil, Dr. Spiros Zafeiratos, Prof. Xinchen Wang and Prof. Markus Antonietti

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201706870

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      Free to dissociate: The simultaneous modification of the electronic band structures, layer-stacking geometry, and crystallinity of carbon nitride polymers enables the liberation of Frenkel exciton dissociation and magnification of the hot-charges yield, which dramatically enhances the visible-light photocatalytic activities.

    4. Reaction Kinetics

      Solvation Accounts for the Counterintuitive Nucleophilicity Ordering of Peroxide Anions

      Robert J. Mayer, Dr. Takahiro Tokuyasu, Dr. Peter Mayer, Dr. Jérôme Gomar, Dr. Stéphane Sabelle, Prof. Benedetta Mennucci, Prof. Herbert Mayr and Dr. Armin R. Ofial

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201707086

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      Weak bases, but strong nucleophiles: Peroxybenzoate ions can be generated in aqueous solution under much less basic conditions than alkyl peroxide anions. Nevertheless, their nucleophilic reactivities exceed those of the alkyl peroxide anions significantly. Quantum chemical calculations reveal solvation to be the origin of the unexpected ordering of reactivity.

  6. Highlights

    1. Rearrangement Reactions

      Enantioselective [2,3]-Sigmatropic Rearrangements: Metal-Bound or Free Ylides as Reaction Intermediates?

      M. Sc. Katharina J. Hock and Prof. Dr. Rene M. Koenigs

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201707092

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      Out of bounds: Enantioselective rearrangement reactions are a long-standing challenge in organic synthesis. Recent advances are highlighted that led to the development of the first enantioselective Doyle–Kirmse reaction and enantioselective rearrangement reactions of iodonium ylides.

  7. Communications

    1. Gel Materials

      Biphasic Synergistic Gel Materials with Switchable Mechanics and Self-Healing Capacity

      Dr. Ziguang Zhao, Yuxia Liu, Kangjun Zhang, Shuyun Zhuo, Dr. Ruochen Fang, Prof. Jianqi Zhang, Prof. Lei Jiang and Prof. Mingjie Liu

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201707239

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      It's morphin’ time: Closely packed switchable micro-inclusions in a hydrogel matrix produce biphasic synergistic gel materials with switchable mechanics, self-healing capacity, and shape-memory properties.

  8. Highlights

    1. Electrocatalysis

      An Active and Robust Bifunctional Oxygen Electrocatalyst through Carbon-Free Hierarchical Functionalization

      Prof. Dr. Kevin Huang

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201707322

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      A hierarchically functionalized hybrid electrode for Zn–air batteries is discussed that requires no carbon. Instead, an oxygen evolution reaction (OER)-active, porous, conductive, and corrosion-resistant nitride Ni3FeN is used as a support for oxygen reduction reaction (ORR)-active ordered intermetallic Fe3Pt NPs. The porosity in the Ni3FeN substrate is an important enabling factor for the high OER activity.

  9. Communications

    1. Synthetic Methods

      Copper-Catalyzed Borylacylation of Activated Alkenes with Acid Chlorides

      Dr. Yuan Huang, Kevin B. Smith and Prof. M. Kevin Brown

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201707323

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      Give 'em the new one, two: A range of activated alkenes underwent rapid copper-catalyzed borylacylation at room temperature at low catalyst loadings (see scheme). The reaction involves borylcupration of the alkene and capture of the resulting alkyl–copper intermediate with an acid chloride. In the case of vinyl arenes, the transformation could be carried out in an enantioselective manner.

    2. Host–Guest Systems | Very Important Paper

      Encapsulation of Isolated Luminophores within Supramolecular Cages

      Dr. Marcel Handke, Dr. Takuji Adachi, Dr. Chunhua Hu and Prof. Michael D. Ward

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201707097

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      The supramolecular cages of a zeolite-like framework were used to encapsulate and isolate molecular luminophores with a range of sizes and emission wavelengths. The luminescence spectra of these host–guest systems were consistent with the presence of isolated monomers and the absence of self-quenching.

    3. Ultrafast Protein Dynamics

      Ultrafast Vibrational Dynamics of Membrane-Bound Peptides at the Lipid Bilayer/Water Interface

      Junjun Tan, Baixiong Zhang, Prof. Yi Luo and Prof. Shuji Ye

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201706996

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      The energy transfer within amide bonds along the backbone of membrane peptides has been studied. Femtosecond infrared-pump sum-frequency generation (SFG) vibrational spectroscopy was used to track the energy transfer from the N−H group to the C=O group within the peptide backbone.

    4. Supramolecules

      You have full text access to this OnlineOpen article
      An Icosidodecahedral Supramolecule Based on Pentaphosphaferrocene: From a Disordered Average Structure to Individual Isomers

      Dr. Claudia Heindl, Dr. Eugenia Peresypkina, Dr. Alexander V. Virovets, Dr. Ivan S. Bushmarinov, M. Sc. Michael G. Medvedev, Barbara Krämer, Priv.-Doz. Dr. Birger Dittrich and Prof. Dr. Manfred Scheer

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201706756

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      With the CF3SO3 anion as a spacer, a new type of giant supramolecule was obtained from pentaphosphaferrocene and Cu+. With 20 copper atoms distributed over the 30 vertices of a giant icosidodecahedron, its unprecedented scaffold contains intrinsic vacancies and exists as four isomers.

    5. Photocatalysis

      Carboxylation of Aromatic and Aliphatic Bromides and Triflates with CO2 by Dual Visible-Light–Nickel Catalysis

      Dr. Qing-Yuan Meng, Shun Wang and Prof. Burkhard König

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201706724

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      Not only good for plants, CO2 (formed in situ from K2CO3) and light enabled the efficient and mild carboxylation of bromides and triflates in the presence of an organic fluorophore and a nickel complex (see scheme). A variety of functional groups were tolerated, and non-activated cyclic alkyl bromides reacted well. The synthesis and derivatization of biologically active molecules demonstrated the applicability of the method in multistep synthesis.

    6. Electrochemical CO2 Reduction

      Role of the Adsorbed Oxygen Species in the Selective Electrochemical Reduction of CO2 to Alcohols and Carbonyls on Copper Electrodes

      Dr. Cécile S. Le Duff, Matthew J. Lawrence and Dr. Paramaconi Rodriguez

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201706463

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      More oxygen, more oxygenation: Pulse voltammetry and copper single crystal electrodes were implemented to determine the influence of oxygen species adsorbed on copper electrodes in the electrochemical reduction of CO2. Product selectivity towards the formation of oxygenated hydrocarbons was associated to the coverage of oxygen species, which is surface-structure- and potential-dependent.

    7. Single-Molecule Magnetism | Hot Paper

      “Isolated” DyO+ Embedded in a Ceramic Apatite Matrix Featuring Single-Molecule Magnet Behavior with a High Energy Barrier for Magnetization Relaxation

      Prof. Pavel E. Kazin, Dr. Mikhail A. Zykin, Dr. Valentina V. Utochnikova, Dr. Oxana V. Magdysyuk, Dr. Alexander V. Vasiliev, Dr. Yan V. Zubavichus, Dr. Walter Schnelle, Prof. Claudia Felser and Prof. Martin Jansen

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201706391

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      Dy2O3-doped apatites show low-temperature hysteresis magnetization with a blocking temperature of up to 11 K and slow relaxation of magnetization with an energy barrier (Ueff) of up to 1043 cm−1. The barrier was determined by an electron spin tunneling through the third and fourth exited Kramers doublet for calcium and strontium compounds, respectively.

    8. C−H Activation

      Divergent C–H Annulation for Multifused N-Heterocycles: Regio- and Stereospecific Cyclizations of N-Alkynylindoles

      Khyarul Alam, Sung Won Hong, Kyung Hwan Oh and Prof. Dr. Jin Kyoon Park

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201705514

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      A short fuse: N-Alkynylindoles were divergently cyclized to give multifused N-heterocycles. The Pd(OAc)2-catalyzed reaction with PPh3 led to 5-exo-dig cycloisomerization, while the PtCl2-catalyzed reaction led to 6-endo-dig cycloisomerization. With PdCl2 and oxidant, β-addition and tandem α-addition, followed by a second ring closure provided bright yellow benzo[7,8]indolizino[2,3,4,5-ija]quinoline, which was also synthesized by a different synthetic route.

    9. Synthetic Methods

      Catalytic Reductive Pinacol-Type Rearrangement of Unactivated 1,2-Diols through a Concerted, Stereoinvertive Mechanism

      Nikolaos Drosos, Dr. Gui-Juan Cheng, Dr. Erhan Ozkal, Bastien Cacherat, Prof. Walter Thiel and Dr. Bill Morandi

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201704936

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      Opportunities for insiders: A catalytic pinacol-type reductive rearrangement of 1,2-internal diols was developed by the use of a simple boron catalyst and two silanes (see scheme). The reaction occurs through a concerted, stereoinvertive mechanism and is applicable to several substrate scaffolds not usually amenable to pinacol-type reactions, such as aliphatic secondary–secondary diols, without the need for prefunctionalization.

    10. Total Synthesis

      Total Synthesis of Crocagin A

      Prof. Dr. Filip Bihelovic, Dr. Desiree Stichnoth, Dr. Frank Surup, Prof. Dr. Rolf Müller and Prof. Dr. Dirk Trauner

      Version of Record online: 18 SEP 2017 | DOI: 10.1002/anie.201612641

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      Let it RiPP: A concise synthesis of the ribosomally produced and post-translationally modified peptides (RiPP) crocagin A is presented. The approach hinges on early formation of the heterotricyclic core, an electrophilic amination, and the stereoselective hydrogenation of a tetrasubstituted double bond.

    11. Molecular Motion | Very Important Paper

      Because the Light is Better Here: Correlation-Time Analysis by NMR Spectroscopy

      Dr. Albert A. Smith, Prof. Dr. Matthias Ernst and Prof. Dr. Beat H. Meier

      Version of Record online: 14 SEP 2017 | DOI: 10.1002/anie.201707316

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      Fighting bias: NMR Dynamics data are more sensitive to some correlation times than to others. Models of the correlation function tend to be biased towards where the light is better, that is, where the experiment is more sensitive, yielding an unreliable characterization of the motion. Replacing modeling by detectors that are sensitive to different ranges of correlation times could help to overcome this bias.

    12. C−H Activation

      Cross-Coupling of α-Carbonyl Sulfoxonium Ylides with C−H Bonds

      Manuel Barday, Christopher Janot, Dr. Nathan R. Halcovitch, Dr. James Muir and Dr. Christophe Aïssa

      Version of Record online: 14 SEP 2017 | DOI: 10.1002/anie.201706804

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      A new alliance: The rhodium-catalyzed cross-coupling of sulfoxonium ylides with carbon–hydrogen bonds, in hexafluoroisopropanol at 60–90 °C, brings these reagents into the realm of C−H activation. When allied to an iridium-catalyzed dehydrative cyclization, this cross-coupling streamlines the synthesis of valuable heterocycles.

    13. Self-Assembly

      Enantioselective Light Harvesting with Perylenediimide Guests on Self-Assembled Chiral Naphthalenediimide Nanofibers

      Ramarani Sethy, Dr. Jatish Kumar, Dr. Rémi Métivier, Marine Louis, Prof. Keitaro Nakatani, Nila Mohan Thazhe Mecheri, Akhila Subhakumari, Prof. K. George Thomas, Prof. Tsuyoshi Kawai and Dr. Takuya Nakashima

      Version of Record online: 14 SEP 2017 | DOI: 10.1002/anie.201707160

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      The enantioselective recognition of a chiral perylenediimide (PDI) molecule by chiral supramolecular nanofibers of a bichromophoric naphthalenediimide (NDI) derivative is described. The chiral recognition was evaluated through the Förster resonance energy transfer (FRET) from the NDI nanofibers to the PDI molecules, which demonstrated the light-harvesting capability of these hybrid systems.

  10. Reviews

    1. Biotechnology

      Cascades in Compartments: En Route to Machine-Assisted Biotechnology

      Dr. Kersten S. Rabe, Dipl.-Chem. Joachim Müller, M. Sc. Marc Skoupi and Prof. Dr. Christof M. Niemeyer

      Version of Record online: 14 SEP 2017 | DOI: 10.1002/anie.201703806

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      Machine-generated multienzyme cascades: The machine-assisted development of biomimetic compartments and catalytic cascades will pave the way towards a novel generation of biotechnological processes. Molecular scaffolds with small cross-linkers, proteins, nucleic acids, colloids, and patterned surfaces can be used to arrange the catalytic units. S: substrate, P: product.

  11. Highlights

    1. Natural Product Synthesis

      Construction of Quaternary Stereogenic Centers in the Total Synthesis of Natural Products

      Dr. Evgeny V. Prusov

      Version of Record online: 14 SEP 2017 | DOI: 10.1002/anie.201706629

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      Total syntheses of the tetracyclic terpene waihoensene and the densely functionalized tetracyclic compound ryanodol have recently been reported. Both approaches constitute examples of the efficient and innovative construction of multiple quaternary centers.

  12. Communications

    1. Imaging Agents | Hot Paper

      Flavylium Polymethine Fluorophores for Near- and Shortwave Infrared Imaging

      Emily D. Cosco, Dr. Justin R. Caram, Dr. Oliver T. Bruns, Daniel Franke, Rachael A. Day, Erik P. Farr, Prof. Moungi G. Bawendi and Prof. Ellen M. Sletten

      Version of Record online: 14 SEP 2017 | DOI: 10.1002/anie.201706974

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      Moving beyond the NIR: A series of polymethine dyes containing a 7-dimethylamino flavylium heterocycle were designed and synthesized. These dyes display distinctly red-shifted absorption and emission. The flavylium heptamethine dye is a bright shortwave infrared (SWIR) emitter and was employed for in vivo SWIR imaging.

    2. Dinuclear Catalysts

      You have full text access to this OnlineOpen article
      Divergent Reactivity of a Dinuclear (NHC)Nickel(I) Catalyst versus Nickel(0) Enables Chemoselective Trifluoromethylselenolation

      Alexander B. Dürr, Dr. Henry C. Fisher, Indrek Kalvet, Khai-Nghi Truong and Prof. Dr. Franziska Schoenebeck

      Version of Record online: 14 SEP 2017 | DOI: 10.1002/anie.201706423

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      A nickel(I) dimer catalyzes the chemoselective trifluoromethylselenolation of aryl iodides, and computational and experimental reactivity data suggest dinuclear NiI catalysis to be operative. The corresponding Ni0 species, on the other hand, suffers from preferred reaction with the product, ArSeCF3, over productive cross-coupling and is hence inactive.

    3. Quantum Chemistry | Hot Paper

      Correct Modeling of Cisplatin: a Paradigmatic Case

      Dr. Nicola Tasinato, Prof. Cristina Puzzarini and Prof. Vincenzo Barone

      Version of Record online: 14 SEP 2017 | DOI: 10.1002/anie.201707683

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      Two are needed for a valid prediction: A dimer of cis-[Pt(NH3)2Cl2] as a quantum chemical model for cisplatin provides the first quantitative agreement with experiment for structural and vibrational properties. This result points out that a reliable in-silico drug design requires a model capturing the essential physical picture of the system and a proper theoretical protocol.

    4. Protein Dynamics

      Analytical Description of NMR Relaxation Highlights Correlated Dynamics in Intrinsically Disordered Proteins

      Dr. Nicola Salvi, Dr. Anton Abyzov and Dr. Martin Blackledge

      Version of Record online: 14 SEP 2017 | DOI: 10.1002/anie.201706740

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      Conformational dynamics of intrinsically disordered proteins (IDPs) define their biological function but remain poorly understood. By combining MD simulation and NMR distinct contributions to this motion are identified, including backbone dihedral jumps and longer-range segmental dynamics.

    5. Gold Nanoparticles

      Evolution of the Ligand Shell Morphology during Ligand Exchange Reactions on Gold Nanoparticles

      Zhi Luo, Jing Hou, Dr. Laure Menin, Dr. Quy Khac Ong and Prof. Francesco Stellacci

      Version of Record online: 14 SEP 2017 | DOI: 10.1002/anie.201708190

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      Patchy ligand distributions: The evolution of the ligand shell morphology during ligand exchange reactions on surfaces of nanoparticles is elucidated for the first time. Kinetics and thermodynamics both play important roles on the formation of patchy domains at different reaction stages.

    6. Electrochemistry | Very Important Paper

      Electrochemically Enabled, Nickel-Catalyzed Amination

      Dr. Chao Li, Dr. Yu Kawamata, Dr. Hugh Nakamura, Julien C. Vantourout, Dr. Zhiqing Liu, Qinglong Hou, Dr. Denghui Bao, Dr. Jeremy T. Starr, Dr. Jinshan Chen, Ming Yan and Prof. Dr. Phil S. Baran

      Version of Record online: 14 SEP 2017 | DOI: 10.1002/anie.201707906

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      Amination electrified: Arguably one of the most important types of bonds, the C−N bond, can now be forged under nickel-catalysis with the aid of electrochemistry. Broad scope, scalability, sustainability, mildness, and rapid reacion rates are some highlights of this interesting new reaction. Tf=trifluoromethanesulfonyl.

    7. NMR Spectroscopy

      A Self-Assembled Oligopeptide as a Versatile NMR Alignment Medium for the Measurement of Residual Dipolar Couplings in Methanol

      Prof. Dr. Xinxiang Lei, Feng Qiu, Dr. Han Sun, Liwen Bai, Wen-Xuan Wang, Prof. Dr. Wensheng Xiang and Prof. Hongping Xiao

      Version of Record online: 13 SEP 2017 | DOI: 10.1002/anie.201705123

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      Alignment medium: A novel, robust, versatile anisotropic medium composed of self-assembled peptides, which are stable at very low concentrations, is used for the measurement of residual dipolar couplings (RDCs) in MeOH. The presented alignment medium is highly homogeneous, and the size of RDCs can be scaled with the concentration of the peptide.

    8. Gold Complexes

      The First Gold(III) Formate: Evidence for β-Hydride Elimination

      Roopender Kumar, Dr. Jean-Philippe Krieger, Prof. Enrique Gómez-Bengoa, Dr. Thomas Fox, Prof. Anthony Linden and Prof. Cristina Nevado

      Version of Record online: 13 SEP 2017 | DOI: 10.1002/anie.201705557

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      An anionic ligand exchange reaction on [(N^C^C)AuIIIF] in the presence of formic acid delivered the first example of a stable gold(III) formate. Its ability to undergo β-hydride elimination and its reactivity in the dehydrogenation of formic acid (FA) have been experimentally and computationally demonstrated.

    9. Catalyst Design | Very Important Paper

      Enzyme Activity by Design: An Artificial Rhodium Hydroformylase for Linear Aldehydes

      Dr. Amanda G. Jarvis, Dr. Lorenz Obrecht, Dr. Peter J. Deuss, Dr. Wouter Laan, Dr. Emma K. Gibson, Dr. Peter P. Wells and Prof. Paul C. J. Kamer

      Version of Record online: 13 SEP 2017 | DOI: 10.1002/anie.201705753

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      Artificial metalloenzymes are hybrid catalysts that offer a unique opportunity to combine the superior performance of natural protein structures with the unnatural reactivity of transition-metal catalytic centers. An artificial rhodium hydroformylase has been developed that displays remarkable activities and selectivities in the biphasic production of long-chain linear aldehydes.

    10. Bioimaging | Hot Paper

      HKOH-1: A Highly Sensitive and Selective Fluorescent Probe for Detecting Endogenous Hydroxyl Radicals in Living Cells

      Xiaoyu Bai, Yueyang Huang, Mingyang Lu and Prof. Dan Yang

      Version of Record online: 13 SEP 2017 | DOI: 10.1002/anie.201705873

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      Highly sensitive and selective probes for hydroxyl radical detection have been developed. The fluorescent probe HKOH-1 has been applied in the screening of antioxidant capacities of several reported hydroxyl radical scavengers. Endogenous hydroxyl radical generation in multiple cell types has been detected with HKOH-1r by both confocal imaging and flow cytometry.

    11. Interfaces

      The Hydrophobic Gap at High Hydrostatic Pressures

      Dr. Florian J. Wirkert, M. Sc. Christoph Hölzl, Dr. Michael Paulus, Dr. Paul Salmen, Prof. Dr. Metin Tolan, Prof. Dr. Dominik Horinek and Dr. Julia Nase

      Version of Record online: 13 SEP 2017 | DOI: 10.1002/anie.201706662

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      The hydrophobic gap, a thin layer of decreased electron density at the interface between water and a solid hydrophobic surface, was studied by X-ray reflectivity experiments and molecular dynamics simulations. The electron depletion in the interfacial region strongly decreases with increasing hydrostatic pressure, which indicates that the interfacial region is compressed more strongly than bulk water. OTS=octadecyltrichlorosilane.

    12. OLEDs

      Highly Efficient Nondoped OLEDs with Negligible Efficiency Roll-Off Fabricated from Aggregation-Induced Delayed Fluorescence Luminogens

      Jian Huang, Han Nie, Jiajie Zeng, Zeyan Zhuang, Shifeng Gan, Yuanjing Cai, Jingjing Guo, Prof. Shi-Jian Su, Prof. Zujin Zhao and Prof. Ben Zhong Tang

      Version of Record online: 13 SEP 2017 | DOI: 10.1002/anie.201706752

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      Neat films of luminogens with aggregation-induced delayed fluorescence (AIDF) were employed in nondoped OLEDs. These systems afford remarkable current, power, and external quantum efficiencies as the concentration-caused emission quenching and exciton annihilation are well suppressed, which leads to high emission efficiencies and efficient exciton utilization in the neat films.

    13. Polymers

      Selective Ring-Opening Polymerization of Non-Strained γ-Butyrolactone Catalyzed by A Cyclic Trimeric Phosphazene Base

      Dr. Na Zhao, Dr. Chuanli Ren, Huaike Li, Yunxin Li, Prof. Dr. Shaofeng Liu and Prof. Dr. Zhibo Li

      Version of Record online: 13 SEP 2017 | DOI: 10.1002/anie.201707122

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      Superbase! Sustainable poly(γ-butyrolactone) was prepared by ring-opening polymerization using a metal-free superbase, that is, a cyclic trimeric phosphazene base. The reaction features high conversion (up to 98%), high molecular weights (up to 22.9 kDa), and selective synthesis of the linear polymer.

    14. Anion Recognition

      High-Fidelity Multistate Switching with Anion–Anion and Acid–Anion Dimers of Organophosphates in Cyanostar Complexes

      Dr. Wei Zhao, Dr. Bo Qiao, Dr. Chun-Hsing Chen and Prof. Dr. Amar H. Flood

      Version of Record online: 13 SEP 2017 | DOI: 10.1002/anie.201707869

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      On–off relationship: Anions in high-fidelity 2:2 complexes formed from phosphate homodimers and cyanostar macrocycles switch directly in and out of the macrocycles when a strong base and acid is added, respectively. An unexpected complex of an acid–anion heterodimer was discovered in step-wise switching with weaker acids.

    15. Zintl Clusters

      Between Localization and Delocalization: Ru(cod)2+ Units in the Zintl Clusters [Bi9{Ru(cod)}2]3− and [Tl2Bi6{Ru(cod)}]2−

      Niels Lichtenberger, Nils Spang, Dr. Andreas Eichhöfer and Prof. Dr. Stefanie Dehnen

      Version of Record online: 13 SEP 2017 | DOI: 10.1002/anie.201707632

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      A little bit of each: DFT studies confirm a hybrid bonding situation in [Bi9{Ru(cod)}2]3− with both localized and delocalized bonds. This cluster and [Tl2Bi6{Ru(cod)}]2− were obtained upon reaction of the binary Zintl anion (TlBi3)2− with [Ru(cod)(H2CC(Me)CH2)2]. Both clusters are rare examples of Zintl anions comprising Ru atoms and illustrate the electronic flexibility of Group 15 polyanions with (pseudo)atoms of other groups.

    16. Rechargeable Batteries | Hot Paper

      Rocking-Chair Ammonium-Ion Battery: A Highly Reversible Aqueous Energy Storage System

      Dr. Xianyong Wu, Yitong Qi, Jessica J. Hong, Zhifei Li, Alexandre S. Hernandez and Prof. Xiulei Ji

      Version of Record online: 13 SEP 2017 | DOI: 10.1002/anie.201707473

      Thumbnail image of graphical abstract

      Charging ahead: An ammonium Prussian white analogue serves as the cathode, an organic solid, 3,4,9,10-perylenetetracarboxylic diimide (PTCDI), as the anode, and 1.0 m (NH4)2SO4 as the electrolyte in an aqueous rocking-chair ammonium-ion battery. The topochemistry of NH4+ in these electrodes points to a new paradigm of NH4+-based energy storage.

    17. Magnetic Materials

      A Material Showing Colossal Positive and Negative Volumetric Thermal Expansion with Hysteretic Magnetic Transition

      Dr. Ji-Xiang Hu, Yang Xu, Dr. Yin-Shan Meng, Dr. Liang Zhao, Prof. Shinya Hayami, Prof. Osamu Sato and Prof. Tao Liu

      Version of Record online: 13 SEP 2017 | DOI: 10.1002/anie.201707258

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      We got both kinds of expansion: A Fe−Co layered network was synthesized. This material exhibits colossal positive and negative thermal expansion (PTE and NTE) at different temperature regions accompanying hysteretic magnetic transitions.

    18. Annulation

      Palladium-Catalyzed [3+3] Annulation of Vinyl Chromium(0) Carbene Complexes through Carbene Migratory Insertion/Tsuji–Trost Reaction

      Kang Wang, Yifan Ping, Taiwei Chang and Prof. Dr. Jianbo Wang

      Version of Record online: 12 SEP 2017 | DOI: 10.1002/anie.201707590

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      Give me a ring: Vinyl chromium(0) carbenes were employed as the three-carbon unit for carbene-based migratory insertion/Tsuji–Trost-type coupling. The annulation of α,β-unsaturated chromium(0) Fischer carbene complexes with 2-iodophenol and 2-iodoanilines was realized through palladium catalysis.

    19. Catalyst Design

      Rational Optimization of Supramolecular Catalysts for the Rhodium-Catalyzed Asymmetric Hydrogenation Reaction

      Dr. Julien Daubignard, Dr. Remko J. Detz, Anne C. H. Jans, Prof. Dr. Bas de Bruin and Prof. Dr. Joost N. H. Reek

      Version of Record online: 12 SEP 2017 | DOI: 10.1002/anie.201707670

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      How to make a catalyst run better: For the first time the computer-based optimization of a supramolecular catalyst for asymmetric hydrogenation reactions is demonstrated. According to DFT calculations and experiments two hydrogen bonds between the catalyst and the substrate exist; increasing the strength of this hydrogen bond interaction by replacing one ligand results in higher reaction rates and higher selectivities.

    20. Allylic Compounds

      Ligand-Controlled Regiodivergent and Enantioselective Copper-Catalyzed Hydroallylation of Alkynes

      Dr. Guoxing Xu, Haiyan Zhao, Bin Fu, Aijie Cang, Dr. Ge Zhang, Qian Zhang, Prof. Tao Xiong and Prof. Qian Zhang

      Version of Record online: 12 SEP 2017 | DOI: 10.1002/anie.201707070

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      Under control: A ligand-controlled regiodivergent and enantioselective copper-catalyzed intermolecular hydroallylation of alkynes with allylic phosphates and hydrosilanes has been achieved. Chiral branched or achiral linear dienes can be obtained by proper choice of the ancillary N-heterocyclic carbene ligand.

    21. Cross-Coupling

      Nickel-Catalyzed Reductive Allylation of Tertiary Alkyl Halides with Allylic Carbonates

      Haifeng Chen, Xiao Jia, Yingying Yu, Dr. Qun Qian and Prof. Hegui Gong

      Version of Record online: 12 SEP 2017 | DOI: 10.1002/anie.201705521

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      All at C: Ni-catalyzed reductive coupling of tertiary alkyl bromides with allylic carbonates enables the formation of all-C(sp3) quaternary centers in good to excellent yields. The reactions exhibit excellent regioselectivity and functional-group tolerance, and a broad substrate scope.

    22. Deubiquitinating Enzymes | Very Important Paper

      You have full text access to this OnlineOpen article
      Release of Enzymatically Active Deubiquitinating Enzymes upon Reversible Capture by Disulfide Ubiquitin Reagents

      Annemieke de Jong, Katharina Witting, Raymond Kooij, Dr. Dennis Flierman and Prof. Dr. Huib Ovaa

      Version of Record online: 12 SEP 2017 | DOI: 10.1002/anie.201706738

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      Capture and release: Ubiquitin-based activity probes were developed that are the first of their kind to yield active deubiquitinating enzymes (DUBs) after capture and release. These reagents form disulfide linkages with the active-site cysteine residue of DUBs. After capture from cell extract using an affinity resin, the disulfide linkage can be mildly cleaved with reducing agents to yield active DUBs.

    23. Multi-Phase Systems

      Compartmentalizing Supramolecular Hydrogels Using Aqueous Multi-phase Systems

      Serhii Mytnyk, Dr. Alexandre G. L. Olive, Dr. Frank Versluis, Dr. Jos M. Poolman, Dr. Eduardo Mendes, Dr. Rienk Eelkema and Prof.Dr. Jan H. van Esch

      Version of Record online: 12 SEP 2017 | DOI: 10.1002/anie.201706272

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      Hydrogel compartments: A versatile approach is used to create aqueous microcompartments inside low-molecular-weight hydrogels using polymer phase separation. Distinct micrometer-sized domains are thus created with controlled composition and unrestricted exchange of even large polar solutes. The method may potentially find use for templating porous soft materials or in the fabrication of tissue engineering scaffolds.

  13. Highlights

    1. Antibiotics

      Pseudouridimycin: the first Nucleoside Analogue that Selectively Inhibits Bacterial RNA Polymerase

      Dr. Mathieu F. Chellat and Prof. Dr. Rainer Riedl

      Version of Record online: 12 SEP 2017 | DOI: 10.1002/anie.201708133

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      Seek, and ye shall find: After years of focusing research on synthetic antibiotics out of fear that all the useful natural ones had already been found, a novel antibacterial compound has been discovered through conventional microbial extract screening. The broad-spectrum nucleoside-analogue inhibitor pseudouridimycin is selective for bacterial RNA polymerase and elicits very low resistance rates.

  14. Communications

    1. Molecular Electronics

      Radical-Enhanced Charge Transport in Single-Molecule Phenothiazine Electrical Junctions

      Dr. Junyang Liu, Dr. Xiaotao Zhao, Qusiy Al-Galiby, Xiaoyan Huang, Jueting Zheng, Ruihao Li, Dr. Cancan Huang, Dr. Yang Yang, Dr. Jia Shi, Dr. David Zsolt Manrique, Prof. Colin J. Lambert, Prof. Martin R. Bryce and Prof. Dr. Wenjing Hong

      Version of Record online: 12 SEP 2017 | DOI: 10.1002/anie.201707710

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      Single-molecule conductances of phenothiazine radicals have been measured using the mechanically controllable break junction technique. Triggered by an acid oxidant, the radical cation of phenothiazine enhances the charge-transport property by up to 200 times with high stability and high junction formation probability at room temperature, which leads to promising applications in single-molecule electronics and spintronics.

    2. Supramolecular Interactions

      Opposing Phase-Segregation and Hydrogen-Bonding Forces in Supramolecular Polymers

      Dr. Senbin Chen, Dr. Tingzi Yan, Matthias Fischer, Anton Mordvinkin, Prof. Dr. Kay Saalwächter, Prof. Dr. Thomas Thurn-Albrecht and Prof. Dr. Wolfgang H. Binder

      Version of Record online: 11 SEP 2017 | DOI: 10.1002/anie.201707363

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      Forces to reckon with: Demixing and coupling through hydrogen bonding are two opposing forces observed in a set of supramolecular diblock copolymers. Hydrogen bonds were torn apart by phase segregation of the attached polymer chains (see picture), as shown by temperature-dependent small-angle X-ray scattering and solid-state 1H NMR spectroscopy.

    3. Annulations

      Synthesis of Phenalenyl-Fused Pyrylium Cations: Divergent C−H Activation/Annulation Reaction Sequence of Naphthalene Aldehydes with Alkynes

      Jiangliang Yin, Meiling Tan, Prof. Dr. Di Wu, Ruyong Jiang, Chengming Li and Prof. Dr. Jingsong You

      Version of Record online: 11 SEP 2017 | DOI: 10.1002/anie.201708127

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      Shell out: The rhodium-catalyzed C−H activation/annulation sequence of naphthalene-type aldehydes with internal alkynes has been developed to provide access to phenalenyl-fused pyrylium cations. Also disclosed is the open-shell radical character of the reduced products.

    4. Antifungal Agents | Hot Paper

      Neutralization of Pathogenic Fungi with Small-Molecule Immunotherapeutics

      Dr. Egor Chirkin, Dr. Viswanathan Muthusamy, Paul Mann, Dr. Terry Roemer, Dr. Philippe G. Nantermet and Prof. Dr. David A. Spiegel

      Version of Record online: 11 SEP 2017 | DOI: 10.1002/anie.201707536

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      Taking aim at chitin: Design and synthesis of non-peptidic small-molecule immunotherapeutics for treatment of fungal infection is reported. A drug candidate was able to recruit endogenous antibodies, thus promoting the dose-dependent phagocytosis of fungal pathogens by human immune effector cells.

    5. Cycloaddition

      Direct and Stereospecific [3+2] Synthesis of Pyrrolidines from Simple Unactivated Alkenes

      Jorge Otero-Fraga, Samuel Suárez-Pantiga, Marc Montesinos-Magraner, Dennis Rhein and Abraham Mendoza

      Version of Record online: 11 SEP 2017 | DOI: 10.1002/anie.201706682

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      Trimethylaluminum promotes the first [3+2] azomethine ylide cycloadditions that engage non-electrophilic olefins. This reaction allows the stereoselective combination of abundant feedstocks to access new polar polydentate scaffolds for ligand design.

  15. Reviews

    1. Robinson Annulation

      Enantioselective Access to Robinson Annulation Products and Michael Adducts as Precursors

      Dr. Florian Gallier, Prof. Arnaud Martel and Dr. Gilles Dujardin

      Version of Record online: 8 SEP 2017 | DOI: 10.1002/anie.201701401

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      Solving the access problem: The asymmetric synthesis of Robinson annulation products from simple non-activated cyclic ketones is still problematic. Solutions have been found by using activated substrates or alternative routes. This Review discusses the actual routes available and also provides an overview of the different asymmetric methods for obtaining those products. A representative illustration is the synthesis of α-cyperone.

  16. Communications

    1. Dynamic Covalent Chemistry

      You have full text access to this OnlineOpen article
      Molecular Recognition-Mediated Transformation of Single-Chain Polymer Nanoparticles into Crosslinked Polymer Films

      Dr. Clare S. Mahon, Dr. Christopher J. McGurk, Dr. Scott M. D. Watson, Dr. Martin A. Fascione, Dr. Chadamas Sakonsinsiri, Prof. Dr. W. Bruce Turnbull and Dr. David A. Fulton

      Version of Record online: 8 SEP 2017 | DOI: 10.1002/anie.201706379

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      Adaptive materials: Single-chain polymer nanoparticles possessing intramolecular dynamic covalent crosslinks can transform into polymer films through a molecular-recognition-mediated crosslinking process. This approach presents a potential method to “wrap” viral, cellular and bacterial surfaces within a layer of polymer film.

    2. Radical Intermediates

      Titanocene-Catalyzed Radical Opening of N-Acylated Aziridines

      Dr. Yong-Qiang Zhang, Elisabeth Vogelsang, Dr. Zheng-Wang Qu, Prof. Dr. Stefan Grimme and Prof. Dr. Andreas Gansäuer

      Version of Record online: 8 SEP 2017 | DOI: 10.1002/anie.201707673

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      Useful intermediates for intermolecular additions, reductions, and cyclizations are obtained with excellent regioselectivity via β-amido-substituted radicals catalytically generated from N-acyl aziridines. DFT calculations indicate that the ring opening is concerted rather than stepwise as previously postulated.

    3. Photoacid Generators

      Enhanced Photophosphorylation of a Chloroplast-Entrapping Long-Lived Photoacid

      Youqian Xu, Dr. Jinbo Fei, Guangle Li, Tingting Yuan, Yue Li, Chenlei Wang, Xianbao Li and Prof. Dr. Junbai Li

      Version of Record online: 8 SEP 2017 | DOI: 10.1002/anie.201706368

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      Photophosphorylation efficiency is enhanced by coupling artificial photoacid generators (PAGs) to a natural photosynthesis system. The in situ proton gradient of the thylakoid lumen is increased under visible light by incorporating long-lived PAGs. An MEH/chloroplast biohybrid produces 3.9 times more adenosine triphosphate (ATP) compared to natural chloroplasts.

    4. Lithium-Ion Batteries | Hot Paper

      Electroless Formation of Hybrid Lithium Anodes for Fast Interfacial Ion Transport

      Snehashis Choudhury, Zhengyuan Tu, Sanjuna Stalin, Duylinh Vu, Kristen Fawole, Deniz Gunceler, Prof. Ravishankar Sundararaman and Prof. Lynden A. Archer

      Version of Record online: 8 SEP 2017 | DOI: 10.1002/anie.201707754

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      Fast interfacial ion transport: A simple electroless ion-exchange approach has been developed for creating coatings of indium on a lithium anode. Joint density functional theory calculation together with experimental results show that the formation of an In film on the Li anode suppresses the dendrite growth and facilitates the Li-ion transport (CE=coulombic efficiency.

    5. Electrochemistry

      Reagent-Free C−H/N−H Cross-Coupling: Regioselective Synthesis of N-Heteroaromatics from Biaryl Aldehydes and NH3

      Huai-Bo Zhao, Zhan-Jiang Liu, Dr. Jinshuai Song and Prof. Dr. Hai-Chao Xu

      Version of Record online: 8 SEP 2017 | DOI: 10.1002/anie.201707192

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      It's electricfying: An unprecedented synthesis of N-heteroaromatics from biaryl aldehydes and NH3 through reagent-free C−H/N-H cross-coupling has been developed. The electrosynthesis uses NH3 as an inexpensive and atom-economic nitrogen donor, requires no oxidizing agents, and allows efficient and regioselective access to a wide range of phenanthridines and structurally related polycyclic N-heteroaromatic products. HFIP=1,1,1,3,3,3-hexafluoro-2-propanol

    6. Bioelectrochemistry

      Real-Time Intracellular Measurements of ROS and RNS in Living Cells with Single Core–Shell Nanowire Electrodes

      Xin-Wei Zhang, Quan-Fa Qiu, Hong Jiang, Fu-Li Zhang, Dr. Yan-Lin Liu, Prof. Dr. Christian Amatore and Prof. Dr. Wei-Hua Huang

      Version of Record online: 8 SEP 2017 | DOI: 10.1002/anie.201707187

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      Nanoelectrodes for biology: A facile and robust strategy for the fabrication of high performance nanowire electrodes (NWEs) was developed. The NWEs allowed the measurement of reactive oxygen and nitrogen species (ROS/RNS) within individual phagolysosomes inside living macrophages.

    7. Chemoenzymatic Synthesis

      Stereoselective Total Synthesis of Bisorbicillinoid Natural Products by Enzymatic Oxidative Dearomatization/Dimerization

      Anna Sib and Prof. Dr. Tobias A. M. Gulder

      Version of Record online: 8 SEP 2017 | DOI: 10.1002/anie.201705976

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      An enzyme for diversity: A chemoenzymatic route to structurally challenging bisorbicillinoid natural products based on the highly stereoselective oxidative dearomatization of sorbicillin with the enzyme SorbC is presented. The streamlined method opens efficient access to a broad range of architecturally diverse compounds from this biomedically interesting natural product family.

    8. Asymmetric Catalysis

      Nickel-Catalyzed Conjugate Addition of Silyl Ketene Imines to In Situ Generated Indol-2-ones: Highly Enantioselective Construction of Vicinal All-Carbon Quaternary Stereocenters

      Jianfeng Zheng, Prof. Dr. Lili Lin, Li Dai, Qiong Tang, Prof. Dr. Xiaohua Liu and Prof. Dr. Xiaoming Feng

      Version of Record online: 8 SEP 2017 | DOI: 10.1002/anie.201705943

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      In a tight spot: An enantioselective conjugate addition of silyl ketene imines to in situ generated indol-2-ones was performed in the presence of a chiral N,N′-dioxide/NiII catalyst. This method provides efficient access to chiral β-alkyl nitriles bearing congested vicinal all-carbon quaternary stereocenters in up to 90 % yield with 23:1 d.r. and 98 % ee. The products can be transformed into chiral pyrroloindoline frameworks and spirocyclohexane oxindole derivatives.

    9. Molecular Dynamics

      Model for the Functional Active State of the TS Ribozyme from Molecular Simulation

      Colin S. Gaines and Prof. Dr. Darrin M. York

      Version of Record online: 8 SEP 2017 | DOI: 10.1002/anie.201705608

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      A new catalytic RNA, the TS ribozyme, is believed to be a metalloribozyme having novel mechanistic features. Molecular dynamic simulations predict a spontaneous local rearrangement of the active site, leading to solution structures consistent with available functional data and providing competing mechanistic hypotheses that can be experimentally tested.

    10. Catalysis | Hot Paper

      Anion–π Catalysis of Diels–Alder Reactions

      Dr. Le Liu, Dr. Yoann Cotelle, Anna-Bea Bornhof, Dr. Céline Besnard, Dr. Naomi Sakai and Prof. Stefan Matile

      Version of Record online: 8 SEP 2017 | DOI: 10.1002/anie.201707730

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      The grand old classic dancing on π-acidic surfaces finally enables otherwise elusive reactivity. For example, the endo/exo diastereoselectivity of the Diels–Alder reaction of hydroxypyrones with fumarates was inverted, and the enantioselective [4+2] cycloaddition of thiazolones and maleimides proceeded with exo specificity without a trace of the otherwise preferred Michael addition product.

  17. Author Profile

    1. Axel Jacobi von Wangelin

      Version of Record online: 7 SEP 2017 | DOI: 10.1002/anie.201708512

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  18. Communications

    1. Cyclization

      Synthesis of Bicyclo[n.1.0]alkanes by a Cobalt-Catalyzed Multiple C(sp3)−H Activation Strategy

      Zhuo-Zhuo Zhang, Ye-Qiang Han, Bei-Bei Zhan, Sai Wang and Prof. Dr. Bing-Feng Shi

      Version of Record online: 7 SEP 2017 | DOI: 10.1002/anie.201707638

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      Double the activation: Described is a cobalt-catalyzed dual C(sp3)−H activation strategy for the synthesis of bicyclo[4.1.0]heptanes and bicyclo[3.1.0]hexanes. A key to the success of this reaction is the conformation-induced C(sp3)−H activation of the resulting cobaltabicyclo[4.n.1] intermediate. Also, the synthesis of bicyclo[3.1.0]hexane from pivalamide by triple C(sp3)−H activation is demonstrated. Q=quinolin-8-yl.

    2. Protein Synthesis

      Chemical Synthesis of the Highly Hydrophobic Antiviral Membrane-Associated Protein IFITM3 and Modified Variants

      Thibault J. Harmand, Dr. Vijaya R. Pattabiraman and Prof. Dr. Jeffrey W. Bode

      Version of Record online: 7 SEP 2017 | DOI: 10.1002/anie.201707554

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      Let's get together: The hydrophobic antiviral membrane protein IFITM3 was assembled through chemoselective ester-forming ligations under acidic conditions that solubilize the peptide segments. The depsipeptides formed upon α-ketoacid-hydroxylamine (KAHA) ligation were rearranged to amides at the end of the synthesis to reveal the protein.

    3. Metalation

      Synthesis of Polyfunctional Diorganomagnesium and Diorganozinc Reagents through In Situ Trapping Halogen–Lithium Exchange of Highly Functionalized (Hetero)aryl Halides in Continuous Flow

      Marthe Ketels, Maximilian A. Ganiek, Niels Weidmann and Prof. Dr. Paul Knochel

      Version of Record online: 7 SEP 2017 | DOI: 10.1002/anie.201706609

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      Go with the flow: A halogen–lithium exchange using BuLi or PhLi was performed in the presence of various metal salts (ZnCl2, MgCl2⋅LiCl) on a broad range of sensitive bromo- or iodo(hetero)arenes using a commercially available continuous-flow setup. The resulting diarylmagnesium or diarylzinc species were trapped with various electrophiles to give polyfunctional (hetero)arenes in high yields and with excellent chemoselectivity.

    4. Controlled Release

      Intracellular Delivery of Functional Native Antibodies under Hypoxic Conditions by Using a Biodegradable Silica Nanoquencher

      Dr. Peiyan Yuan, Dr. Hailong Zhang, Dr. Linghui Qian, Xin Mao, Shubo Du, Dr. Changmin Yu, Bo Peng and Prof. Dr. Shao Q. Yao

      Version of Record online: 7 SEP 2017 | DOI: 10.1002/anie.201705578

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      Better delivery is possible: The first hypoxia-responsive antibody-encapsulated silica nanoquencher was developed to achieve endocytosis-independent cell uptake and on-demand intracellular release of native therapeutic antibodies in cancer cells, with the capability to simultaneously image both antibody release and hypoxic state of cells.

    5. Drug Discovery

      Beyond the BET Family: Targeting CBP/p300 with 4-Acyl Pyrroles

      Martin Hügle, Dr. Xavier Lucas, Dr. Dmytro Ostrovskyi, Dr. Pierre Regenass, Dr. Stefan Gerhardt, Prof. Dr. Oliver Einsle, Mirjam Hau, Prof. Dr. Manfred Jung, Prof. Dr. Bernhard Breit, Prof. Dr. Stefan Günther and Dr. Daniel Wohlwend

      Version of Record online: 7 SEP 2017 | DOI: 10.1002/anie.201705516

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      You better you BET: XDM-CBP is a highly potent and selective inhibitor for the bromodomains (BRDs) of CBP and p300 derived from a pan-selective BET (bromodomain and extra-terminal domain) BRD-binding fragment. Along with X-ray crystal structure analysis and thermodynamic profiling, XDM-CBP was used in screenings of several cancer cell lines in vitro to study its inhibitory potential on cancer cell proliferation.

    6. Chemical Biology | Hot Paper

      Targeting the Genome-Stability Hub Ctf4 by Stapled-Peptide Design

      Dr. Yuteng Wu, Dr. Fabrizio Villa, Dr. Joseph Maman, Dr. Yu Heng Lau, Lina Dobnikar, Dr. Aline C. Simon, Prof. Karim Labib, Prof. David R. Spring and Prof. Luca Pellegrini

      Version of Record online: 7 SEP 2017 | DOI: 10.1002/anie.201705611

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      Interfering with the replisome: The replisome hub protein Ctf4 represents an attractive potential target for developing cancer therapeutics. The development of stapled peptides that disrupt the interaction of Ctf4 with its client proteins in the replisome provides proof-of-principle evidence of how this can be achieved. CIP=Ctf4-interacting peptide.

    7. Soft Matter

      Liquid Tubule Formation and Stabilization Using Cellulose Nanocrystal Surfactants

      Xubo Liu, Dr. Shaowei Shi, Yanan Li, Dr. Joe Forth, Dr. Dong Wang and Prof. Thomas P. Russell

      Version of Record online: 7 SEP 2017 | DOI: 10.1002/anie.201706839

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      Free flowin': Cellulose nanocrystal (CNC)-based nanoparticle surfactants, termed CNC-surfactants, are reported. By adjusting the pH, concentrations of the CNC/polymer ligands, and flow conditions, the dripping-to-jetting transition can be achieved easily because of the reduced interfacial energy, and the aqueous tubules can be stabilized indefinitely, which opens a new platform for additive manufacturing techniques of all-liquid constructs.

    8. CO2 Reduction

      Self-Cleaning Catalyst Electrodes for Stabilized CO2 Reduction to Hydrocarbons

      Dr. Zhe Weng, Xing Zhang, Yueshen Wu, Prof. Shengjuan Huo, Dr. Jianbing Jiang, Dr. Wen Liu, Guanjie He, Prof. Yongye Liang and Prof. Hailiang Wang

      Version of Record online: 7 SEP 2017 | DOI: 10.1002/anie.201707478

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      A surface-restructuring strategy is presented for self-cleaning Cu catalyst electrodes with unprecedented catalytic stability toward CO2 reduction to hydrocarbons. Pd atoms pre-deposited on the Cu surface induce continuous restructuring of the surface (see scheme). This process constantly refreshes the catalyst surface and avoids deactivation by carbonaceous species.

    9. Photodynamic Therapy

      Homo- and Heteroleptic Phototoxic Dinuclear Metallo-Intercalators Based on RuII(dppn) Intercalating Moieties: Synthesis, Optical and Biological Studies

      Dr. Hiwa K. Saeed, Dr. Paul J. Jarman, Dr. Stuart Archer, Sreejesh Sreedharan, Dr. Ibrahim Q. Saeed, Luke K. Mckenzie, Prof. Julia A. Weinstein, Dr. Niklaas J. Buurma, Prof. Carl G. W. Smythe and Prof. Jim A. Thomas

      Version of Record online: 7 SEP 2017 | DOI: 10.1002/anie.201707350

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      2 for 1 on PDT: New dinuclear RuII(dppn) and mixed RuII(dppn)/RuII(dppz) complexes display much enhanced cellular uptake properties compared to simple RuII(dppz) analogues. They are phototoxic and are particularly potent against chemotherapeutically resistant cells. The luminescent RuII(dppn)/RuII(dppz) complex also offers potential as a theranostic lead.

    10. Magnetic Properties | Very Important Paper

      Molecular Dynamics of Hexamethylbenzene at Low Temperatures: Evidence of Unconventional Magnetism Based on Rotational Motion of Protons

      Dr. Fei Yen, Zhenzheng Zhao, Sixia Hu and Dr. Lang Chen

      Version of Record online: 7 SEP 2017 | DOI: 10.1002/anie.201707024

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      A strongly correlated system: A previously unidentified type of magnetism based on the rotational motion of protons within methyl groups is shown to occur in hexamethylbenzene. At lower temperatures spin–spin interactions exist between methyl groups aligned in a previously unclassified type of antiferromagnetic configuration.

    11. Electrochemistry

      Single Graphene Layer on Pt(111) Creates Confined Electrochemical Environment via Selective Ion Transport

      Dr. Yongchun Fu, Dr. Alexander V. Rudnev, Dr. Gustav K. H. Wiberg and Prof. Matthias Arenz

      Version of Record online: 7 SEP 2017 | DOI: 10.1002/anie.201705952

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      Nanocatalysis: A confined two-dimensional electrochemical environment has been created using the interspace between a single layer of graphene and a single-crystal Pt(111) surface while exposing it to electrolyte solutions. The penetration and intercalation of ions into the 2D confined space are found to be highly selective: only protons can enter while anions and larger cations are excluded.

    12. Biohybrid Micromotors

      Chemotaxis-Guided Hybrid Neutrophil Micromotors for Targeted Drug Transport

      Dr. Jingxin Shao, Dr. Mingjun Xuan, Hongyue Zhang, Dr. Xiankun Lin, Dr. Zhiguang Wu and Prof. Qiang He

      Version of Record online: 7 SEP 2017 | DOI: 10.1002/anie.201706570

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      Motoring in the right direction: Self-guided biohybrid micromotors were developed by integrating natural neutrophils with mesoporous silica nanoparticles camouflaged with bacterial membranes. The hybrid species inherited the intrinsic chemotaxis capability of the neutrophils and moved autonomously along chemoattractant gradients without external energy input to transport a cargo to the targeted site.

    13. Electrochemistry

      Fluorescence Electrochemical Microscopy: Capping Agent Effects with Ethidium Bromide/DNA Capped Silver Nanoparticles

      Dr. Eden E. L. Tanner, Stanislav V. Sokolov, Dr. Neil P. Young, Dr. Christopher Batchelor-McAuley and Prof. Richard G. Compton

      Version of Record online: 7 SEP 2017 | DOI: 10.1002/anie.201707809

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      Undercover investigation: Fluorescence electrochemical microscopy has been used to examine capping agent effects of intercalated ethidium bromide/DNA-capped silver nanoparticles, allowing insight into the role the capping agent plays in electron transfer from the nanoparticle.

    14. Heterogeneous Catalysis

      Observation and Identification of an Atomic Oxygen Structure on Catalytic Gold Nanoparticles

      Kai Liu, Tao Chen, Shuyue He, Jason P. Robbins, Prof. Simon G. Podkolzin and Prof. Fei Tian

      Version of Record online: 7 SEP 2017 | DOI: 10.1002/anie.201706647

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      Catalytic gold: An atomic oxygen structure Au-O-Au-O-Au was observed and identified on gold nanoparticles in catalytic decomposition of hydrogen peroxide to oxygen and water. Calculations confirm that on surfaces with coordinatively unsaturated gold atoms, two oxygen atoms preferentially share a gold atom and additionally bind to two other surface gold atoms with a larger bond distance.

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