Angewandte Chemie International Edition

Cover image for Vol. 54 Issue 37

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. Editorials

    1. You have free access to this content
      More Chemistry with Light! More Light in Chemistry!

      Prof. Dr. Thorsten Bach

      Article first published online: 2 SEP 2015 | DOI: 10.1002/anie.201507439

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      “… Why is chemistry overlooked when talking about light? Is the photon a physical particle per se? Are all important light-induced processes biological? Maybe the role of light for chemistry and the role of chemistry for light may be far less important than a few eccentric scientists would like to believe. From the perspective of a synthetically oriented photochemist, however, the facts are different …” Read more in the Editorial by Thorsten Bach.

  2. Cover Pictures

    1. Six-Coordinate Group 13 Complexes: The Role of d Orbitals and Electron-Rich Multi-Center Bonding

      Maarten G. Goesten, Dr. Celia Fonseca Guerra, Prof. Dr. Freek Kapteijn, Prof. Dr. Jorge Gascon and Prof. Dr. F. Matthias Bickelhaupt

      Article first published online: 2 SEP 2015 | DOI: 10.1002/anie.201507909

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      The d or not the d, that is the question that F. M. Bickelhaupt, M. G. Goesten et al. address in their Communication on six-coordinate Group 13 complexes (DOI: 10.1002/anie.201504864). Their resemblance with transition-metal analogues has formerly been suggested to hint at an involvement of the d atomic orbitals of the Group 13 elements. It is now shown that these orbitals play essentially no role, and that the bonding in these six-coordinate complexes is best described in terms of 7-center-12-electron bonds.

  3. Communications

    1. Chiral Polymerization

      Autoresolution of Segregated and Mixed p-n Stacks by Stereoselective Supramolecular Polymerization in Solution

      Bhawani Narayan, Karteek K. Bejagam, Prof. Sundaram Balasubramanian and Prof. Subi J. George

      Article first published online: 2 SEP 2015 | DOI: 10.1002/anie.201506435

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      Chiral stacking: A chirality-driven self-sorting strategy has been introduced for the construction of mixed and segregated donor-acceptor supramolecular arrays in solution.

    2. Metathesis

      The Triple-Bond Metathesis of Aryldiazonium Salts: A Prospect for Dinitrogen Cleavage

      Dr. Aaron D. Lackner and Prof. Alois Fürstner

      Article first published online: 2 SEP 2015 | DOI: 10.1002/anie.201506546

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      Who knows? Although the extrusion of molecular nitrogen from aryldiazonium salts is extremely facile, the metathetic cleavage of the N[BOND]N triple bond on treatment with alkylidyne ate complexes of molybdenum or tungsten is shown to be even faster. The analogy between [Ar-N2]+ and known [M-N2] complexes makes this process a potential model for dinitrogen cleavage devoid of any redox steps.

  4. Editorials

    1. You have free access to this content
      The Scientific Bridge: Fifty Years of Germany–Israel Diplomatic Relations

      Prof. Dr. Helmut Schwarz, Prof. Dr. Itamar Willner and Prof. Dr. Ilan Marek

      Article first published online: 2 SEP 2015 | DOI: 10.1002/anie.201506694

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      “… Fifty years ago, out of the ashes of the Second World War, the German Chancellor, Konrad Adenauer, and the Israeli Prime Minister, David Ben-Gurion, initiated the establishment of diplomatic relations between Germany and Israel. This special issue commemorates the fruitful and mutually enriching long-term collaborations between Israeli and German scientists … Read more in the Editorial by Helmut Schwarz, Itamar Willner, and Ilan Marek.

  5. Communications

    1. Bioinorganic Chemistry | Hot Paper

      A Photoactive Carbon-Monoxide-Releasing Protein Cage for Dose-Regulated Delivery in Living Cells

      Kenta Fujita, Dr. Yuya Tanaka, Dr. Satoshi Abe and Prof. Dr. Takafumi Ueno

      Article first published online: 2 SEP 2015 | DOI: 10.1002/anie.201506738

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      Photoactivable protein cage: A ferritin protein cage retaining manganese–carbonyl complexes released carbon monoxide (CO; see picture) under visible-light irradiation. The amount of released CO is modulated by the irradiation period. The system showed an optimized CO dose for activating a cellular transcriptional factor.

    2. Butterfly Complexes

      E4 Butterfly Complexes (E=P, As) as Chelating Ligands

      Dr. Christoph Schwarzmaier, Dr. Sebastian Heinl, Dr. Gábor Balázs and Prof. Dr. Manfred Scheer

      Article first published online: 2 SEP 2015 | DOI: 10.1002/anie.201506784

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      The butterfly has landed: The first examples of the coordination of E4 butterfly complexes (E=P, As) are presented. It is shown that the “wing-tip” E atoms are capable of acting as ligands towards Cu+ cations. The E4 moieties act as bidentate ligands with a very narrow bite-angle, which is comparable to that of dppm (bis(diphenylphosphino)methane).

    3. Dehydrogenation | Very Important Paper

      Al2O3 Nanosheets Rich in Pentacoordinate Al3+ Ions Stabilize Pt-Sn Clusters for Propane Dehydrogenation

      Dr. Lei Shi, Gao-Ming Deng, Prof. Wen-Cui Li, Dr. Shu Miao, Qing-Nan Wang, Prof. Wei-Ping Zhang and Prof. An-Hui Lu

      Article first published online: 2 SEP 2015 | DOI: 10.1002/anie.201507119

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      Stable and selective: γ-Al2O3 nanosheets rich in pentacoordinate Al3+ ions can well disperse and stabilize raft-like Pt-Sn clusters, which results in an increase of the electron density of the Pt sites. This material catalyzes the conversion of propane into propylene with >99 % selectivity, and minimizes coke formation and sintering processes.

    4. Alkenes

      Rhodium-Catalyzed Dehydrogenative Borylation of Aliphatic Terminal Alkenes with Pinacolborane

      Dr. Masao Morimoto, Dr. Tomoya Miura and Prof. Dr. Masahiro Murakami

      Article first published online: 2 SEP 2015 | DOI: 10.1002/anie.201506328

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      Crazy like a fox: Aliphatic terminal alkenes react with pinacolborane at ambient temperature in the presence of [Rh(cod)2]BF4/iPr-Foxap and norbornene to produce dehydrogenative borylation compounds as the major product. The reaction is applied to the one-pot syntheses of aldehydes and homoallylic alcohols from aliphatic terminal alkenes. cod=1,5-cyclooctadiene.

    5. Structural Biology

      Resolution of Stepwise Cooperativities of Copper Binding by the Homotetrameric Copper-Sensitive Operon Repressor (CsoR): Impact on Structure and Stability

      Alexander D. Jacobs, Dr. Feng-Ming James Chang, Dr. Lindsay Morrison, Dr. Jonathan M. Dilger, Prof. Vicki H. Wysocki, Prof. David E. Clemmer and Prof. David P. Giedroc

      Article first published online: 2 SEP 2015 | DOI: 10.1002/anie.201506349

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      Working together: The step-wise cooperativities of Cu binding to the homotetrameric copper-sensitive operon repressor (CsoR) were resolved by mass spectrometry, with the extent of cooperativity related to gas phase properties. The gas phase holo (Cu4) structure was found to favor a more compact state, and was markedly more resistant to fragmentation than apo- or partially Cu-ligated species.

    6. Metalloradicals

      Kinetic Destabilization of Metal–Metal Single Bonds: Isolation of a Pentacoordinate Manganese(0) Monoradical

      Douglas W. Agnew, Dr. Curtis E. Moore, Prof. Arnold L. Rheingold and Prof. Joshua S. Figueroa

      Article first published online: 2 SEP 2015 | DOI: 10.1002/anie.201506498

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      Staying neutral: The unstable 17e monoradical [Mn(CO)5] is known to dimerize rapidly to form a Mn[BOND]Mn single bond. Two sterically encumbering isocyanide ligands are used to destabilize the Mn[BOND]Mn bond, leading to the formation of the isolable manganese(0) monoradical [Mn(CO)3(CNArDipp2)2] (ArDipp2=2,6-(2,6-iPr2C6H3)2C6H3). The persistence of this species is exploited to gain insight into nitrosarene spin-trapping studies of [Mn(CO)5].

    7. Molecular-Sieve Films

      In Situ Electrochemical Synthesis of Oriented and Defect-Free AEL Molecular-Sieve Films Using Ionic Liquids

      Tongwen Yu, Prof. Wenling Chu, Prof. Rui Cai, Yanchun Liu and Prof. Weishen Yang

      Article first published online: 2 SEP 2015 | DOI: 10.1002/anie.201506183

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      Al be back: An in situ electrochemical ionothermal method allows highly oriented and defect-free AlPO4-11 molecular-sieve films to be synthesized using an Al electrode as the Al source. The AlPO4-11 film shows excellent corrosion resistance.

    8. Silylamide Complexes

      The Instability of Ni{N(SiMe3)2}2: A Fifty Year Old Transition Metal Silylamide Mystery

      Michelle Faust, Aimee M. Bryan, Akseli Mansikkamäki, Petra Vasko, Prof. Marilyn M. Olmstead, Prof. Heikki M. Tuononen, Prof. Fernande Grandjean, Prof. Gary J. Long and Prof. Philip P. Power

      Article first published online: 2 SEP 2015 | DOI: 10.1002/anie.201505518

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      The singular instability of Ni{N(SiMe3)2}2, one of the original transition metal silylamides of Bürger and Wannagat, was re-investigated: it likely results from its tendency to undergo autoreduction into the dispersion force stabilized NiI tetramer [Ni{N(SiMe3)2}]4 (see picture; Si light blue, N dark blue, Ni green), the first neutral homoleptic NiI amide.

  6. Minireviews

    1. Small-Ring Systems

      Cyclobutane and Cyclobutene Synthesis: Catalytic Enantioselective [2+2] Cycloadditions

      Yao Xu, Michael L. Conner and Prof. M. Kevin Brown

      Article first published online: 2 SEP 2015 | DOI: 10.1002/anie.201502815

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      Squared away: Cyclobutanes and cyclobutenes are important structural motifs found in numerous biologically significant molecules, and they are useful intermediates for chemical synthesis. Consequently, catalytic enantioselective [2+2] cycloadditions to access cyclobutanes and cyclobutenes have emerged as an attractive target for method development. The advances made in catalytic enantioselective [2+2] cycloadditions are described herein.

  7. Communications

    1. Boron Monolayers

      Two-Dimensional Boron Monolayers Mediated by Metal Substrates

      Dr. Zhuhua Zhang, Yang Yang, Guoying Gao and Prof. Boris I. Yakobson

      Article first published online: 2 SEP 2015 | DOI: 10.1002/anie.201505425

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      Concerto in B flat: 2D materials usually have a specific lattice structure that is independent of external conditions. In contrast, the structure of 2D boron (red, see picture) depends on the metal substrate. On weakly interacting metals, 2D boron shows significant off-plane buckling but on more reactive metals, it strongly favors a planar structure.

    2. Thermoelectrics

      Thermoelectricity Generation and Electron–Magnon Scattering in a Natural Chalcopyrite Mineral from a Deep-Sea Hydrothermal Vent

      Prof. Ran Ang, Dr. Atta Ullah Khan, Dr. Naohito Tsujii, Dr. Ken Takai, Dr. Ryuhei Nakamura and Prof. Takao Mori

      Article first published online: 2 SEP 2015 | DOI: 10.1002/anie.201505517

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      It came from the deep: A chalcopyrite mineral from a deep-sea hydrothermal vent has been found to have a large thermoelectric power and a high power factor, in which electron–magnon scattering and a large effective mass were detected. These findings highlight the feasibility of the generation of thermoelectric energy from natural materials that are abundant in the Earth’s crust.

    3. Cobalt Catalysts

      Coordination Chemistry of [Co(acac)2] with N-Doped Graphene: Implications for Oxygen Reduction Reaction Reactivity of Organometallic Co-O4-N Species

      Jongwoo Han, Young Jin Sa, Yeonjun Shim, Min Choi, Prof. Dr. Noejung Park, Prof. Dr. Sang Hoon Joo and Prof. Dr. Sungjin Park

      Article first published online: 2 SEP 2015 | DOI: 10.1002/anie.201504707

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      Active species for ORR: Hybrid materials are synthesized by the reaction of a Co-based organometallic complex with N-doped graphene at room temperature. These materials show high electrocatalytic activity for the oxygen reduction reaction. The coordination around Co is revealed by experimental and theoretical studies, and the catalytically active species is identified as a Co-O4-N structure.

    4. Cycloarylenes

      Belt-Shaped Cyclonaphthylenes

      Dr. Zhe Sun, Dr. Parantap Sarkar, Takuya Suenaga, Dr. Sota Sato and Prof. Dr. Hiroyuki Isobe

      Article first published online: 1 SEP 2015 | DOI: 10.1002/anie.201506424

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      Being persistent: Cyclonaphthylene nanohoops have been synthesized and characterized in solution and in the solid state. The naphthylene units in [8]cyclo-amphi-naphthylene, prepared by linking naphthylene units at the 2,6-positions, can undergo rotation, but rigidification with the aid of methylene bridges affords persistent molecular structures in solution.

    5. Cross-Coupling

      Palladium-Catalyzed Catellani ortho-Acylation Reaction: An Efficient and Regiospecific Synthesis of Diaryl Ketones

      Yunze Huang, Rui Zhu, Kun Zhao and Prof. Dr. Zhenhua Gu

      Article first published online: 1 SEP 2015 | DOI: 10.1002/anie.201506446

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      In position: A palladium-catalyzed Catellani ortho-acylation of aryl halides using either acid chlorides or acid anhydrides was developed. The reaction efficiently and regiospecifically introduces an acyl group to the position ortho to the halogen atom. Preliminary kinetic studies indicate that H2O plays an important role, and that acid anhydrides might be the active acylating reagents. TFP=tri(2-furyl)phosphine.

    6. C[BOND]C Activation

      Manganese-Catalyzed Oxidative Azidation of Cyclobutanols: Regiospecific Synthesis of Alkyl Azides by C[BOND]C Bond Cleavage

      Rongguo Ren, Huijun Zhao, Leitao Huan and Prof. Dr. Chen Zhu

      Article first published online: 1 SEP 2015 | DOI: 10.1002/anie.201506578

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      Cleaved: An efficient manganese-catalyzed synthesis of alkyl azides is based on the C[BOND]C bond cleavage of cyclobutanols. A wide range of primary, secondary, and tertiary alkyl azides and a series of medium-sized cyclic azides were generated in synthetically useful yields. Preliminary mechanistic studies suggest that the reaction proceeds by a radical mechanism.

    7. Enzyme Catalysis

      Probing the Catalytic Promiscuity of a Regio- and Stereospecific C-Glycosyltransferase from Mangifera indica

      Dawei Chen, Dr. Ridao Chen, Dr. Ruishan Wang, Dr. Jianhua Li, Kebo Xie, Chuancai Bian, Lili Sun, Xiaolin Zhang, Jimei Liu, Prof. Dr. Lin Yang, Prof. Dr. Fei Ye, Prof. Dr. Xiaoming Yu and Prof. Dr. Jungui Dai

      Article first published online: 1 SEP 2015 | DOI: 10.1002/anie.201506505

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      C-glycodiversification: MiCGT, as the first benzophenone C-glycosyltransferase (CGT) from Mangifera indica, showed robust regio- and stereospecific C-glycosylation activity for 35 structurally diverse acceptors with UDP-glucose or xylose. The aryl-C-glycoside 1 exhibited potent antidiabetic activity toward SGLT2.

    8. Synthetic Methods

      Intramolecular Aminoboration of Unfunctionalized Olefins

      Chun-Hua Yang, Yu-Shi Zhang, Wen-Wen Fan, Dr. Gong-Qing Liu and Prof. Dr. Yue-Ming Li

      Article first published online: 1 SEP 2015 | DOI: 10.1002/anie.201505489

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      All cats banned! BCl3 (1 equiv) was used as the sole boron source for the direct intramolecular aminoboration of alkenes. The intramolecular aminoboration of sulfonamide derivatives of 4-penten-1-amines, 5-hexen-1-amines, and 2-allylanilines proceeded readily without a catalyst and was followed by straightforward hydrolysis and treatment with pinacol to give the corresponding boronates (see scheme).

    9. C[BOND]H Activation

      Ortho C[BOND]H Acylation of Aryl Iodides by Palladium/Norbornene Catalysis

      Zhe Dong, Jianchun Wang, Zhi Ren and Prof. Dr. Guangbin Dong

      Article first published online: 1 SEP 2015 | DOI: 10.1002/anie.201506397

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      Double (re)agent: A palladium/norbornene-catalyzed ortho-acylation of aryl iodides was developed, and is enabled by isopropyl carbonate anhydrides, which function as both an acyl cation equivalent and a hydride source. This reaction exhibits excellent functional-group compatibility and broad substrate scope. Heterocycle moieties can be tolerated on both the aryl and acyl partners. FG=functional group.

    10. Natural Product Synthesis

      You have full text access to this OnlineOpen article
      Total Synthesis of (+)-Rubriflordilactone A

      Shermin S. Goh, Dr. Guilhem Chaubet, Dr. Birgit Gockel, Marie-Caroline A. Cordonnier, Hannah Baars, Andrew W. Phillips and Prof. Edward A. Anderson

      Article first published online: 1 SEP 2015 | DOI: 10.1002/anie.201506366

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      Two in one: Two enantioselective total syntheses of the nortriterpenoid natural product rubriflordilactone A are described, which use palladium- or cobalt-catalyzed cyclizations to converge on a late-stage synthetic intermediate. These key processes are set up through the coupling of a common diyne component with appropriate AB-ring aldehydes, a strategy that enables a broad exploration of this family of natural products, as well as synthetic analogues.

    11. Allenes

      Highly Regioselective Radical Amination of Allenes: Direct Synthesis of Allenamides and Tetrasubstituted Alkenes

      Ge Zhang, Prof. Tao Xiong, Zining Wang, Guoxing Xu, Xuedan Wang and Prof. Qian Zhang

      Article first published online: 1 SEP 2015 | DOI: 10.1002/anie.201506066

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      Radical highway: By employing N-fluoroarylsulfonimide as a nitrogen source, a facile, mild, and highly regioselective copper-catalyzed oxidative radical amination of various allenes was developed. In addition, a protocol involving nitrogen radical addition/fluorine-atom transfer affords fluorinated tetrasubstituted alkenes by using silver as catalyst.

    12. C[BOND]H Activation

      Readily Removable Directing Group Assisted Chemo- and Regioselective C(sp3)[BOND]H Activation by Palladium Catalysis

      Yun-Fei Zhang, Prof. Dr. Hong-Wei Zhao, Hui Wang, Jiang-Bo Wei and Prof. Dr. Zhang-Jie Shi

      Article first published online: 1 SEP 2015 | DOI: 10.1002/anie.201505932

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      Director’s cut: 2-Piconimide, prepared from commercially available 2-picolinamide/2-picolic acid as precursors, was used for the first time to direct C[BOND]H arylation/alkenylation by palladium catalysis. The directing group promotes a sequential primary and secondary C(sp3)[BOND]H arylation with different aryl iodides in one substrate and can be easily removed.

    13. Metal–Metal Interactions

      Direct X-Ray Scattering Evidence for Metal–Metal Interactions in Solution at the Molecular Level

      Andrea Cebollada, Alba Vellé, Dr. Manuel Iglesias, Lauren B. Fullmer, Dr. Sara Goberna-Ferrón, Dr. May Nyman and Dr. Pablo J. Sanz Miguel

      Article first published online: 1 SEP 2015 | DOI: 10.1002/anie.201505736

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      In close quarters: Small-angle X-ray scattering (SAXS) is used to identify structure in solution by taking advantage of the excellent scattering intensity of heavy metals which have associated through metallophilic interactions. The close relationship between the solid-state and solution arrangements of a [Ag2(bisNHC)2]2+ system is described.

    14. NMR Spectroscopy

      Shaped Ceria Nanocrystals Catalyze Efficient and Selective Para-Hydrogen-Enhanced Polarization

      Evan W. Zhao, Haibin Zheng, Dr. Ronghui Zhou, Prof. Helena E. Hagelin-Weaver and Prof. Clifford R. Bowers

      Article first published online: 1 SEP 2015 | DOI: 10.1002/anie.201506045

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      Intense NMR signals are induced by the incorporation of para-hydrogen into propene and propane through pairwise addition and replacement over octahedron-, cube-, or rod-shaped ceria nanocrystals. The synthesis of ceria nanoparticles with well-defined shapes and different surface facets was essential to gaining detailed insights into the mechanisms of these processes.

    15. Protein Ligation

      Oxidative Deselenization of Selenocysteine: Applications for Programmed Ligation at Serine

      Dr. Lara R. Malins, Dr. Nicholas J. Mitchell, Dr. Sheena McGowan and Prof. Richard J. Payne

      Article first published online: 1 SEP 2015 | DOI: 10.1002/anie.201504639

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      An operationally simple method for the rapid and chemoselective conversion of selenocysteine (Sec) to serine (Ser) in aqueous media is described. This mechanistically distinct transformation at selenium facilitates the synthesis of complex peptides and proteins, as highlighted in the synthesis of fragments of the epithelial glycoproteins MUC5AC and MUC4 and in the total synthesis of the serine protease inhibitor eglin C.

    16. Antibiotics | Hot Paper

      An Accurate In Vitro Model of the E. coli Envelope

      Dr. Luke A. Clifton, Dr. Stephen A. Holt, Dr. Arwel V. Hughes, Dr. Emma L. Daulton, Dr. Wanatchaporn Arunmanee, Dr. Frank Heinrich, Dr. Syma Khalid, Damien Jefferies, Dr. Timothy R. Charlton, Dr. John R. P. Webster, Dr. Christian J. Kinane and Prof. Jeremy H. Lakey

      Article first published online: 1 SEP 2015 | DOI: 10.1002/anie.201504287

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      Understanding the outer membranes of Gram-negative bacteria is important for the development of new antibacterial compounds. However, their structure and dynamics are poorly understood because of their small in vivo size and inaccurate in vitro models. A stable asymmetric model of the outer membrane that can be analyzed by a range of biophysical techniques and accurately imitates the in vivo behavior of natural outer membranes is herein presented.

  8. Reviews

    1. Surface Functionalization

      Efficient Photochemical Approaches for Spatially Resolved Surface Functionalization

      Dr. Guillaume Delaittre, Dr. Anja S. Goldmann, Jan O. Mueller and Prof. Dr. Christopher Barner-Kowollik

      Article first published online: 1 SEP 2015 | DOI: 10.1002/anie.201504920

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      “There are only patterns”: A range of efficient photochemical platforms for the spatially resolved functionalization of surfaces is described in this Review together with their specific advantages relative to alternative methods. There is already a powerful range of methods available, but orthogonal ligation processes driven by visible light remain largely elusive.

  9. Communications

    1. Tuberculosis

      Isoniazid@Fe2O3 Nanocontainers and Their Antibacterial Effect on Tuberculosis Mycobacteria

      Dr. Peter Leidinger, Jens Treptow, Kristine Hagens, Jacqueline Eich, Dr. Nicole Zehethofer, Dr. Dominik Schwudke, Dr. Wulf Oehlmann, Dr. Heinrich Lünsdorf, Dr. Oliver Goldmann, Prof. Dr. Ulrich E. Schaible, Dr. Kurt E. J. Dittmar and Prof. Dr. Claus Feldmann

      Article first published online: 31 AUG 2015 | DOI: 10.1002/anie.201505493

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      Like a Trojan horse: Isoniazid-filled Fe2O3 nanocontainers are actively taken up by tuberculosis-infected macrophages and show high activity against the pathogen Mycobacterium tuberculosis (M.tb.). This type of container allows a much higher drug loading than other nanocontainer drug-delivery systems, and has a high biocompatibility and biodegradability.

    2. Cyclizations

      Functionalization of Styrenes by Copper-Catalyzed Borylation/ ortho-Cyanation and Silver-Catalyzed Annulation Processes

      Dr. Wanxiang Zhao and Prof. John Montgomery

      Article first published online: 31 AUG 2015 | DOI: 10.1002/anie.201507303

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      A Cu and Ag sequence: The bis-functionalization of styrenes is accomplished through a copper-catalyzed process that enables hydroboration of the alkene and regioselective ortho cyanation of the arene. The resulting adducts are converted, by a radical cyclization process, into a cyclopentanone unit fused to the original aromatic ring. Together, these methods allow efficient cyclopentannulation of a broad range of styrene derivatives.

    3. Anthraquinones

      Practical Synthesis of p- and o-Amino- and Methoxyphenolic Anthraquinones

      Prof. Dr. K. C. Nicolaou, Dr. Min Lu, Pengxi Chen and Dr. Akshay A. Shah

      Article first published online: 31 AUG 2015 | DOI: 10.1002/anie.201507007

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      Fusion: 3-Cyanophthalides (V) react with substituted amino semiquinone aminals (VI, VII) under basic conditions to provide selectively a diverse array of substituted amino- and methoxyphenolic anthraquinones (IIV).

  10. Essays

    1. Solar Energy Conversion

      Light: A Very Peculiar Reactant and Product

      Prof. Vincenzo Balzani, Dr. Giacomo Bergamini and Prof. Paola Ceroni

      Article first published online: 31 AUG 2015 | DOI: 10.1002/anie.201502325

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      See the light of day: Light is the fastest way of transferring energy and information through space, and in chemistry it can perform the dual role of reactant and product. Sunlight, a really unique reactant, represents our ultimate energy source. Chemists are engaged in designing systems for the conversion of light into electrical or chemical energy and vice versa to create a more sustainable way of life.

  11. Communications

    1. Photocatalysis

      Increased Water Reduction Efficiency of Polyelectrolyte-Bound Trimetallic [Ru,Rh,Ru] Photocatalysts in Air-Saturated Aqueous Solutions

      Theodore R. Canterbury, Dr. Shamindri M. Arachchige, Prof. Robert B. Moore and Prof. Karen J. Brewer

      Article first published online: 31 AUG 2015 | DOI: 10.1002/anie.201506567

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      Better together: A photocatalytic system that functions under aerobic conditions by electrostatically binding water reduction photocatalysts to poly(4-styrenesulfonate) (PSS) is reported. The water-soluble complex–PSS assemblies were formed in situ upon addition of PSS to the photocatalyst solutions. Substantial H2 production under aerobic conditions occured for PSS-containing aqueous solutions (see picture).

    2. Nanoparticles

      Reversible Size Control of Liquid-Metal Nanoparticles under Ultrasonication

      Dr. Akihisa Yamaguchi, Yu Mashima and Prof. Dr. Tomokazu Iyoda

      Article first published online: 31 AUG 2015 | DOI: 10.1002/anie.201506469

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      An ultrasonication method for reversibly changing the size of gallium nanoparticles (GaNPs) has been developed. By changing the temperature or adding acid, the balance between the break-up and coalescence of the GaNPs can be adjusted by modulating the natural surface oxide layer and the stabilizing effect of a surfactant. Moreover, these GaNPs display size-dependent plasmonic absorption.

    3. Ruthenium Carbenes | Very Important Paper

      Formation of Ruthenium Carbenes by gem-Hydrogen Transfer to Internal Alkynes: Implications for Alkyne trans-Hydrogenation

      M. Sc. Markus Leutzsch, Dr. Larry M. Wolf, Puneet Gupta, Dr. Michael Fuchs, Prof. Walter Thiel, Dr. Christophe Farès and Prof. Alois Fürstner

      Article first published online: 31 AUG 2015 | DOI: 10.1002/anie.201506075

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      Let′s stay together: Certain ruthenium complexes are able to catalyze the stereochemically highly unusual trans-hydrogenation of internal alkynes, but can also effect a geminal hydrogenation, during which both H atoms of a single H2 precursor are delivered to the very same alkyne C atom whilst the neighboring C atom is converted into a metal carbene. The significance of this finding is analyzed by PHIP NMR spectroscopy (PHIP=para-hydrogen-induced polarization transfer) and density functional calculations.

    4. Multiple Bonds

      A Two-Coordinate Cobalt(II) Imido Complex with NHC Ligation: Synthesis, Structure, and Reactivity

      Jingzhen Du, Linbo Wang, Prof. Dr. Meihua Xie and Prof. Dr. Liang Deng

      Article first published online: 31 AUG 2015 | DOI: 10.1002/anie.201505937

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      It takes two: A two-coordinate Co complex with a metal–element multiple bond [(IPr)Co(NDmp)] (IPr=1,3-bis(2′,6′-diisopropylphenyl)imidazole-2-ylidene; Dmp=2,6-dimesitylphenyl) was prepared and structurally characterized. The low-coordinate CoII complex underwent group-transfer reactions with CO and ethylene, and activated E[BOND]H (E=C, Si) bonds to form CoII alkynyl and hydride complexes as 1,2-addition products. Dipp=2,6-diisopropylphenyl.

    5. Membrane Proteins

      Solid-state NMR Study of the YadA Membrane-Anchor Domain in the Bacterial Outer Membrane

      Dr. Shakeel A. Shahid, Dr. Madhu Nagaraj, Nandini Chauhan, Dr. Trent W. Franks, Dr. Benjamin Bardiaux, Dr. Michael Habeck, Dr. Marcella Orwick-Rydmark, Prof. Dirk Linke and Dr. Barth-J. van Rossum

      Article first published online: 31 AUG 2015 | DOI: 10.1002/anie.201505506

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      Going native: Solid-state NMR was used to study the structure and dynamics at ambient temperature of the membrane-anchor domain of YadA in a native membrane environment, specifically the outer membrane of E. coli. YadA is an adhesin from the pathogen Yersinia enterocolitica that is involved in host-cell interactions and is used as a model protein for studying the autotransport process.

    6. Core/Shell Nanoparticles

      Precisely Size-Tunable Magnetic/Plasmonic Core/Shell Nanoparticles with Controlled Optical Properties

      Prof. Di Yang, Xinchang Pang, Yanjie He, Prof. Yiquan Wang, Genxiang Chen, Wenzhong Wang and Prof. Zhiqun Lin

      Article first published online: 31 AUG 2015 | DOI: 10.1002/anie.201504676

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      Star-like amphiphilic triblock copolymers with narrow molecular weight distributions were synthesized by combining two sequential atom-transfer radical polymerizations with a click reaction. A family of uniform magnetic/plasmonic core/shell nanoparticles with precisely controllable core diameters and shell thicknesses were then obtained by capitalizing on these triblock copolymers as nanoreactors [PAA=poly(acrylic acid), PEO=poly(ethylene oxide)].

    7. Photophysics

      Excited-State Dynamic Planarization of Cyclic Oligothiophenes in the Vicinity of a Ring-to-Linear Excitonic Behavioral Turning Point

      Kyu Hyung Park, Dr. Pyosang Kim, Woojae Kim, Dr. Hideyuki Shimizu, Dr. Minwoo Han, Prof. Dr. Eunji Sim, Prof. Dr. Masahiko Iyoda and Prof. Dr. Dongho Kim

      Article first published online: 31 AUG 2015 | DOI: 10.1002/anie.201504588

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      Going around in circles: Excited-state dynamic planarization processes of π-conjugated cyclic oligothiophenes were investigated using time-resolved fluorescence spectra and molecular dynamics simulations. Excitons formed in a cyclic oligothiophene composed of six subunits fully delocalize (“cyclic exciton”), whereas those formed in larger systems fail to achieve complete delocalization (“acyclic exciton”).

    8. H2S Nanosensors

      Monitoring of Endogenous Hydrogen Sulfide in Living Cells Using Surface-Enhanced Raman Scattering

      Dr. Da-Wei Li, Lu-Lu Qu, Kai Hu, Prof. Dr. Yi-Tao Long and Prof. Dr. He Tian

      Article first published online: 28 AUG 2015 | DOI: 10.1002/anie.201505025

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      Rapid, selective, and sensitive: The endogenous H2S in living cells can be detected rapidly, selectively, and sensitively using a surface-enhanced Raman scattering (SERS) nanosensor, 4-acetamidobenzenesulfonyl azide-functionalized gold nanoparticles (AuNPs/4-AA). Based on the rapid and specific reaction between H2S and 4-AA, combined with the sensitive fingerprinting capability of SERS, the nanosensor can monitor the endogenous H2S generated in a variety of pathophysiological pathways.

    9. Diazo Compounds

      Activation of α-Diazocarbonyls by Organic Catalysts: Diazo Group Acting as a Strong N-Terminal Electrophile

      Lei Li, Jia-Jia Chen, Yi-Jin Li, Xiu-Bin Bu, Qun Liu and Yu-Long Zhao

      Article first published online: 28 AUG 2015 | DOI: 10.1002/anie.201505064

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      Active duty: 1,8-Diazabicyclo[5.4.0]undec-7-ene catalyzes the C[BOND]N bond-forming reactions of active methylenes, as C nucleophiles, with α-diazocarbonyls, as N-terminal electrophiles, under ambient reaction conditions. DBU plays activates both the active methylene and α-diazocarbonyl.

    10. Gold Nanoparticles

      Controlled Light-Mediated Preparation of Gold Nanoparticles by a Norrish Type I Reaction of Photoactive Polymers

      Florian Mäsing, Dr. Artur Mardyukov, Carsten Doerenkamp, Prof. Dr. Hellmut Eckert, Ursula Malkus, Harald Nüsse, Prof. Dr. Jürgen Klingauf and Prof. Dr. Armido Studer

      Article first published online: 28 AUG 2015 | DOI: 10.1002/anie.201505133

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      Instant preparation of Au nanoparticles! Mixing a photoactive polymer with HAuCl4 and NaOH in DMF/H2O and irradiating with light for a few minutes provides stable, spherical, polymer-coated Au nanoparticles with defined diameter. The diameter can be adjusted from 1.5 to 9.6 nm by varying the length and composition of the photoactive polymer.

    11. Synthetic Methods

      An Indoxyl-Based Strategy for the Synthesis of Indolines and Indolenines

      Yuanyuan Yu, Dr. Guang Li, Long Jiang and Prof. Dr. Liansuo Zu

      Article first published online: 28 AUG 2015 | DOI: 10.1002/anie.201505173

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      Making other arrangements: The chemical synthesis of a diverse range of functionalized indolines/indolenines and the formal total synthesis of the indoline natural product minfiensine were achieved by using an indoxyl-based strategy that proceeds via unprecedented aza-pinacol rearrangements. This method provides direct access to the core structures of several classes of indole alkaloids by employing conceptually distinct bond disconnections.

    12. Natural Product Synthesis

      Biomimetic Total Syntheses of (−)-Leucoridines A and C through the Dimerization of (−)-Dihydrovalparicine

      Praveen Kokkonda, Keaon R. Brown, Trevor J. Seguin, Dr. Steven E. Wheeler, Dr. Shivaiah Vaddypally, Dr. Michael J. Zdilla and Dr. Rodrigo B. Andrade

      Article first published online: 28 AUG 2015 | DOI: 10.1002/anie.201505198

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      Concise biomimetic syntheses of the Strychnos-Strychnos-type bis-indole alkaloids (−)-leucoridine A and C were accomplished through the biomimetic dimerization of (−)-dihydrovalparicine. DFT calculations were used to elucidate the mechanism, which favors a stepwise aza-Michael/spirocyclization sequence over the alternate hetero-Diels–Alder cycloaddition reaction.

    13. Asymmetric Catalysis

      Copper-Catalyzed Enantioselective 1,6-Boration of para-Quinone Methides and Efficient Transformation of gem-Diarylmethine Boronates to Triarylmethanes

      Yazhou Lou, Prof. Dr. Peng Cao, Tao Jia, Yongling Zhang, Dr. Min Wang and Prof. Dr. Jian Liao

      Article first published online: 28 AUG 2015 | DOI: 10.1002/anie.201505926

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      Quite a gem: The first enantioselective copper-catalyzed 1,6-conjugate addition of bis(pinacolato)diboron to para-quinone methides is presented. It proceeds with excellent yields and good to excellent enantioselectivities, and provides an attractive approach for the construction of optically active gem-diarylmethine boronic esters, which can be converted into triarylmethanes with highly enantiospecificity.

    14. Drug Delivery | Hot Paper

      Enzymatic Prenylation and Oxime Ligation for the Synthesis of Stable and Homogeneous Protein–Drug Conjugates for Targeted Therapy

      Dr. Joong-jae Lee, Hyo-Jung Choi, Misun Yun, YingJin Kang, Ji-Eun Jung, Dr. Yiseul Ryu, Tae Yoon Kim, Young-je Cha, Prof. Hyun-Soo Cho, Prof. Jung-Joon Min, Dr. Chul-Woong Chung and Prof. Hak-Sung Kim

      Article first published online: 28 AUG 2015 | DOI: 10.1002/anie.201505964

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      A chemoenzymatic conjugation method that is based on enzymatic prenylation and oxime ligation is a simple and efficient means for generating highly stable and homogeneous protein–drug conjugates in a site-specific manner. It can be generally applied to the conjugation of drugs to a wide range of protein binders, facilitating the development of targeted therapies with high efficacies and low off-target effects.

    15. Core–Shell Nanostructures

      Establishing the Structural Integrity of Core–Shell Nanoparticles against Elemental Migration using Luminescent Lanthanide Probes

      Bing Chen, Dr. Dengfeng Peng, Xian Chen, Prof. Xvsheng Qiao, Prof. Xianping Fan and Prof. Feng Wang

      Article first published online: 28 AUG 2015 | DOI: 10.1002/anie.201506157

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      Border control: The diffusion of dopant ions in core–shell nanostructures is detected using luminescent lanthanide probes (Ce3+ and Tb3+). Core–shell nanoparticles synthesized by a wet-chemistry route retain high structural integrity and after annealing at elevated temperatures, migration of elements across the core–shell interface is detected.

    16. Ring Expansion

      1,2-Phosphaborines: Hybrid Inorganic/Organic P–B Analogues of Benzene

      Dr. Jonathan H. Barnard, Paul A. Brown, Prof. Dr. Kevin L. Shuford and Prof. Dr. Caleb D. Martin

      Article first published online: 28 AUG 2015 | DOI: 10.1002/anie.201507003

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      Jamming PB into benzene: 1,2-Phosphaborines were synthesized by the ring expansion reaction of boroles with the cyclic phosphine [PPh]5 under UV irradiation. The products were structurally characterized revealing a planar central ring. The nature of the bonding was analyzed computationally and indicated that the heterocycle had appreciable aromatic character.

    17. Viruses | Hot Paper

      Whole-Genome Sequencing of a Single Viral Species from a Highly Heterogeneous Sample

      Dr. Hee-Sun Han, Paul G. Cantalupo, Dr. Assaf Rotem, Dr. Shelley K. Cockrell, Martial Carbonnaux, Prof. James M. Pipas and Prof. David A. Weitz

      Article first published online: 28 AUG 2015 | DOI: 10.1002/anie.201507047

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      On a drop-in basis: A new platform that integrates drop-based microfluidics and computational analysis was developed for purification of a single viral species from a mixed sample and retrieval of its complete genome sequence. This method was used to retrieve the genome sequence of SV40 spiked into wastewater with more than 96 % sequence coverage and 99.8 % sequence identity. The platform can also be used to detect and identify unknown viruses.

  12. Book Reviews

    1. Chemistry of Organo-Hybrids. Synthesis and Characterization of Functional Nano-Objects. Edited by Bernadette Charleux, Christophe Coperet, and Emmanuel Lacote.

      Andreas F. M. Kilbinger

      Article first published online: 28 AUG 2015 | DOI: 10.1002/anie.201507587

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      John Wiley and Sons, Hoboken 2015. 552 pp., hardcover, € 135.00.—ISBN 978-1118379028

  13. Communications

    1. Electrocatalysis | Hot Paper

      Stability of Fe-N-C Catalysts in Acidic Medium Studied by Operando Spectroscopy

      Dr. Chang Hyuck Choi, Claudio Baldizzone, Jan-Philipp Grote, Dr. Anna K. Schuppert, Dr. Frédéric Jaouen and Dr. Karl J. J. Mayrhofer

      Article first published online: 28 AUG 2015 | DOI: 10.1002/anie.201504903

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      The stable potential window of Fe-N-C catalysts for oxygen reduction reactions is studied using a scanning flow cell equipped with advanced online analytical techniques. Fe demetalation and carbon oxidation (see picture) are observed in low (<0.7 V) and high (>0.9 V) potential regions, respectively, which can introduce significant performance drops in a fuel cell.

    2. Composite Materials

      Biological Chitin–MOF Composites with Hierarchical Pore Systems for Air-Filtration Applications

      Dorothea Wisser, Florian M. Wisser, Silvia Raschke, Dr. Nicole Klein, Dr. Matthias Leistner, Dr. Julia Grothe, Prof. Dr. Eike Brunner and Prof. Dr. Stefan Kaskel

      Article first published online: 28 AUG 2015 | DOI: 10.1002/anie.201504572

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      Sponge bag: A composite material is formed from a metal–organic framework (MOF) and a chitin biopolymeric network extracted from a marine sponge. The inner surface functionalities of the biomatrix cause the MOF HKUST-1 (Cu3BTC2) to crystalize inside the hollow chitin fibers, resulting in a hierarchical pore system with a surface area of up to 800 m2 g−1. The composite shows a high affinity for toxic industrial gases such as NH3.

    3. Asymmetric Catalysis

      Carbamate-Catalyzed Enantioselective Bromolactamization

      Dr. Yi An Cheng, Wesley Zongrong Yu and Prof. Dr. Ying-Yeung Yeung

      Article first published online: 28 AUG 2015 | DOI: 10.1002/anie.201504724

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      A splash of EtOH: A highly facile, efficient, and enantioselective bromolactamization of olefinic amides was effected by a carbamate catalyst and ethanol additive. The amide substrates undergo N-cyclization predominantly to give a diverse range of enantioenriched bromolactam products which contain up to two chiral centers. Ts=4-toluenesulfonyl.

    4. Unconventional Retrosynthesis

      Final-Stage Site-Selective Acylation for the Total Syntheses of Multifidosides A–C

      Dr. Yoshihiro Ueda, Dr. Takumi Furuta and Prof. Dr. Takeo Kawabata

      Article first published online: 28 AUG 2015 | DOI: 10.1002/anie.201504729

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      On ′site′: A new retrosynthetic route to 4-O-acylated natural and unnatural glycosides is demonstrated. The title reaction of unprotected glycoside precursors, possessing multiple hydroxy groups, was performed successfully. The total syntheses of multifidosides A, B, and C were completed using this acylation strategy.

    5. Coatings

      Fluorine-Free Anti-Smudge Polyurethane Coatings

      Muhammad Rabnawaz, Guojun Liu and Heng Hu

      Article first published online: 28 AUG 2015 | DOI: 10.1002/anie.201504892

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      Wear and tear without a smear: Anti-smudge polyurethane coatings produced without fluorinated reagents were clear at thicknesses up to tens of micrometers. The coatings were applied to a diverse range of substrates and shown to repel ink, a fingerprint liquid, paint, and water. Moreover, they retained their anti-smudge properties even after extensive wear.

    6. Large-Molecule Adsorption

      Clicked Isoreticular Metal–Organic Frameworks and Their High Performance in the Selective Capture and Separation of Large Organic Molecules

      Dr. Pei-Zhou Li, Dr. Xiao-Jun Wang, Si Yu Tan, Chung Yen Ang, Hongzhong Chen, Dr. Jia Liu, Prof. Dr. Ruqiang Zou and Prof. Dr. Yanli Zhao

      Article first published online: 28 AUG 2015 | DOI: 10.1002/anie.201504346

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      Color me pretty: Highly porous metal–organic frameworks with uniform topological networks were constructed by isoreticular extension through click reactions. The accessibility of their pores to large molecules make them highly promising materials for size-dependent large-molecule capture and separation, as demonstrated visually by the selective capture of dye molecules (see picture; MeB=methylene blue, R6G=rhodamine 6G, BBR=brilliant blue R).

    7. Membrane Proteins

      Spontaneous Reconstitution of Functional Transmembrane Proteins During Bioorthogonal Phospholipid Membrane Synthesis

      Christian M. Cole, Dr. Roberto J. Brea, Young Hun Kim, Michael D. Hardy, Prof. Jerry Yang and Prof. Neal K. Devaraj

      Article first published online: 28 AUG 2015 | DOI: 10.1002/anie.201504339

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      Membrane Proteins Inc.: The spontaneous reconstitution of functional integral membrane proteins (gray) during the de novo synthesis of biomimetic phospholipid bilayers is described. The method takes advantage of bioorthogonal coupling reactions for the non-enzymatic generation of proteoliposomes from micelle-solubilized proteins. This chemoselective approach results in a fast and clean reconstitution without the need for dialysis to remove excess detergent.

    8. Porous Aromatic Frameworks

      Highly Efficient Enrichment of Volatile Iodine by Charged Porous Aromatic Frameworks with Three Sorption Sites

      Dr. Zhuojun Yan, Dr. Ye Yuan, Dr. Yuyang Tian, Prof. Daming Zhang and Prof. Guangshan Zhu

      Article first published online: 28 AUG 2015 | DOI: 10.1002/anie.201503362

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      Polymers for iodine capture: Targeted synthesis of porous aromatic frameworks has been achieved by choosing the monomer lithium tetrakis(4-iodophenyl)borate (LTIPB) as the building block. Three effective sorption sites are assembled into the frameworks: an aromatic ring, triple bond, and ionic bond. These frameworks exhibit the highest values for iodine sorption among all porous materials (zeolites, MOFs, and POFs).

    9. Asymmetric Catalysis

      Chiral Cyclopentadienyl Iridium(III) Complexes Promote Enantioselective Cycloisomerizations Giving Fused Cyclopropanes

      Dr. Michael Dieckmann, Yun-Suk Jang and Prof. Dr. Nicolai Cramer

      Article first published online: 27 AUG 2015 | DOI: 10.1002/anie.201506483

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      Be selective! A set of chiral CpxIrIII complexes (Cpx=chiral cyclopentadienyl) based on atropchiral cyclopentadienyl ligands are presented. The complexes, in particular the tert-butoxy-substituted derivative (see picture), are shown to promote the asymmetric cycloisomerization of enynes to form fused cyclopropanes with high enantioselectivities.

    10. Drug Delivery | Hot Paper

      Self-Assembled DNA Nanoclews for the Efficient Delivery of CRISPR–Cas9 for Genome Editing

      Wujin Sun, Wenyan Ji, Jordan M. Hall, Quanyin Hu, Dr. Chao Wang, Prof. Dr. Chase L. Beisel and Prof. Dr. Zhen Gu

      Article first published online: 27 AUG 2015 | DOI: 10.1002/anie.201506030

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      All rolled into one: A biologically inspired delivery vehicle for CRISPR–Cas9 is based on yarn-like DNA nanoparticles that are synthesized by rolling circle amplification. The DNA nanoclews were efficiently loaded with Cas9 protein/single guide RNA complexes and delivered them into human cells, enabling targeted gene disruption.

    11. Mesoporous Materials | Hot Paper

      Periodic Mesoporous Organosilica with Molecular-Scale Ordering Self-Assembled by Hydrogen Bonds

      Dr. Norihiro Mizoshita and Dr. Shinji Inagaki

      Article first published online: 27 AUG 2015 | DOI: 10.1002/anie.201505538

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      Host–guest systems: Self-assembly of an organosilane precursor by hydrogen bonding is the key to construction of a new class of crystal-like periodic mesoporous organosilicas (see picture). The present mesoporous materials can stably accomodate silane-free H-bonding guest molecules within the pore walls, which is applicable to non-covalent modification of organosilica hybrids.

    12. Foldamers

      A Hollow Foldecture with Truncated Trigonal Bipyramid Shape from the Self-Assembly of an 11-Helical Foldamer

      Jae-Hoon Eom, Jintaek Gong, Dr. Sunbum Kwon, Dr. Aram Jeon, Rokam Jeong, Dr. Russell W. Driver and Prof. Dr. Hee-Seung Lee

      Article first published online: 27 AUG 2015 | DOI: 10.1002/anie.201504248

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      Gigantic molecular containers: The self-assembly of an 11-helical foldamer provided highly crystalline, hollow foldectures with truncated trigonal bipyramid shape. These foldectures are molecular hosts in a way reminiscent of a biological microcompartment.

    13. Nanostructures | Hot Paper

      Large-Area, Free-Standing, Two-Dimensional Supramolecular Polymer Single-Layer Sheet for Highly Efficient Electrocatalytic Hydrogen Evolution

      Dr. Renhao Dong, Martin Pfeffermann, Dr. Haiwei Liang, Dr. Zhikun Zheng, Dr. Xiang Zhu, Dr. Jian Zhang and Prof. Dr. Xinliang Feng

      Article first published online: 26 AUG 2015 | DOI: 10.1002/anie.201506048

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      Standing up: The Langmuir–Blodgett method can be used to prepare two-dimensional supramolecular polymer (2DSP) sheets from nickel bis(dithiolene) complexes at the air–water interface (see figure). These free-standing single-layer sheets, which are 0.7–0.9 nm thick and square millimeters in area, showed excellent electrocatalytic activities in the hydrogen evolution reaction from water.

    14. Anticancer Nanoparticles

      Near-Infrared-Activated Nanocalorifiers in Microcapsules: Vapor Bubble Generation for In Vivo Enhanced Cancer Therapy

      Jingxin Shao, Mingjun Xuan, Dr. Luru Dai, Dr. Tieyan Si, Prof. Junbai Li and Prof. Qiang He

      Article first published online: 26 AUG 2015 | DOI: 10.1002/anie.201506115

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      Antitumor bubbles: A photothermal theranostic platform based on biocompatible gold nanorod-assembled capsules was demonstrated with good deformability behavior and behavior similar to red blood cells. The resulting vapor bubbles, induced by a cumulative thermal effect between adjacent gold nanorods, can locally damage tumor cells and enable photothermal therapy with high efficacy compared to single gold nanorods.

    15. Orthogonal Translation

      Ribosome Subunit Stapling for Orthogonal Translation in E. coli

      Dr. Stephen D. Fried, Dr. Wolfgang H. Schmied, Dr. Chayasith Uttamapinant and Prof. Jason W. Chin

      Article first published online: 26 AUG 2015 | DOI: 10.1002/anie.201506311

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      Stapling the ribosome together: An orthogonal ribosome was designed in which the large and small subunits are connected through a covalent RNA staple, and directed to an orthogonal mRNA. This ribosome is active in protein synthesis in cells and enables otherwise lethal mutations to be introduced into the large subunit. This paves the way for the ribosome-catalyzed synthesis of unnatural polymers by cellular orthogonal translation.

    16. Perovskite Phases

      Large Magnetization and Frustration Switching of Magnetoresistance in the Double-Perovskite Ferrimagnet Mn2FeReO6

      Dr. Angel M. Arévalo-López, Graham M. McNally and Prof. J. Paul Attfield

      Article first published online: 26 AUG 2015 | DOI: 10.1002/anie.201506540

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      Double-perovskite magnetism: The double perovskite Mn2FeReO6 synthesized at high pressure has magnetic transition-metal cations at all sites. High-spin Mn2+ cations lead to record magnetizations for double-perovskite ferrimagnets and their frustrated magnetic order at 75 K switches magnetoresistance from negative to large positive values at low temperatures.

    17. Strontium guanidinate | Hot Paper

      Synthesis, Structure, and Properties of SrC(NH)3, a Nitrogen-Based Carbonate Analogue with the Trinacria Motif

      M. Sc. Ronja Missong, M. Sc. Janine George, Dr. Andreas Houben, Dr. Markus Hoelzel and Prof. Dr. Richard Dronskowski

      Article first published online: 26 AUG 2015 | DOI: 10.1002/anie.201507113

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      Keeping an ion guanidinate: Strontium guanidinate, SrC(NH)3, the first compound with a doubly deprotonated guanidine unit, was synthesized, and its properties investigated using X-ray and neutron powder diffraction as well as IR spectroscopy. Combined with quantum-theoretical calculations, allows a qualitative and quantitative discussion some first insights into the structure of the anionic guanidine unit.

  14. Meeting Reviews

    1. Symposium Report

      Supramolecular Chemistry … and Beyond

      Dr. Anna K. H. Hirsch

      Article first published online: 26 AUG 2015 | DOI: 10.1002/anie.201506536

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      The research group of Jean-Marie Lehn recently celebrated its 50th anniversary. Lehn, who shared the Nobel Prize in Chemistry 1987 with Donald J. Cram and Charles J. Pedersen, has been active in many initiatives in the European chemical community, and was instrumental in the founding of Chemistry—A European Journal and ChemBioChem. This Meeting Report summarizes the symposium that was recently held to commemorate the achievements of the Lehn group.

  15. Reviews

    1. Multidimensional Spectroscopy

      Multidimensional Electronic Spectroscopy of Photochemical Reactions

      Prof. Dr. Patrick Nuernberger, Dr. Stefan Ruetzel and Prof. Dr. Tobias Brixner

      Article first published online: 26 AUG 2015 | DOI: 10.1002/anie.201502974

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      Two dimensions provide more insight than one: Coherent electronic multidimensional spectroscopy in different variations allows the separation of photochemical reaction channels. This is demonstrated exemplarily for a molecular switch capable of light-induced ring-opening and ring-closure reactions, cis—trans isomerization, vibrational wave-packet dynamics, radical cation formation, and population relaxation.

  16. Communications

    1. Biosensors | Hot Paper

      Site-Directed, On-Surface Assembly of DNA Nanostructures

      Dr. Rebecca Meyer, Dr. Barbara Saccà and Prof. Dr. Christof M. Niemeyer

      Article first published online: 26 AUG 2015 | DOI: 10.1002/anie.201505553

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      From micro to nano: Orthogonal topographic modification of planar DNA nanostructures combined with site-directed on-surface assembly provides a means to bridge top-down micropatterning with bottom-up nanotechnology.

    2. C[BOND]H Activation

      Redox-Neutral Rhodium-Catalyzed C[BOND]H Functionalization of Arylamine N-Oxides with Diazo Compounds: Primary C(sp3)[BOND] H/C(sp2)[BOND]H Activation and Oxygen-Atom Transfer

      Dr. Bing Zhou, Zhaoqiang Chen, Dr. Yaxi Yang, Wen Ai, Huanyu Tang, Yunxiang Wu, Dr. Weiliang Zhu and Dr. Yuanchao Li

      Article first published online: 26 AUG 2015 | DOI: 10.1002/anie.201505302

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      Untapped reactivity: The title reaction affords 1H-benzo[g]indolines under mild reaction conditions and external oxidants are not required. The only by-products are dinitrogen and water. This reaction represents the first example of dual functionalization of an unactivated primary C(sp3)[BOND]H and C(sp2)[BOND]H bond with diazocarbonyl compounds. Moreover, a method to access various aminomandelic acid derivatives by an O-atom-transfer strategy is described.

    3. Transfer Hydrogenation

      B(C6F5)3-Catalyzed Transfer of Dihydrogen from One Unsaturated Hydrocarbon to Another

      Dr. Indranil Chatterjee, Dr. Zheng-Wang Qu, Prof. Dr. Stefan Grimme and Prof. Dr. Martin Oestreich

      Article first published online: 26 AUG 2015 | DOI: 10.1002/anie.201504941

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      Well balanced: Wheland complexes that were generated by B(C6F5)3-mediated hydride abstraction from cyclohexa-1,4-dienes engage in the transfer hydrogenation of alkenes. Problems arising from the involvement of carbenium ion intermediates, resulting in cationic hetero- or homodimerization, are overcome by sterically shielding the hydridic C3 position of the dihydrogen surrogate (see Scheme). The mechanism was analyzed by quantum-chemical calculations.

    4. Solid-State NMR Spectroscopy

      Compensating Pulse Imperfections in Solid-State NMR Spectroscopy: A Key to Better Reproducibility and Performance

      Johannes J. Wittmann, Dr. Kazuyuki Takeda, Prof. Dr. Beat H. Meier and Prof. Dr. Matthias Ernst

      Article first published online: 26 AUG 2015 | DOI: 10.1002/anie.201504782

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      Deviations in the radio-frequency field (pulse transients) can have a severe impact on the performance of pulse sequences. A method based on transient-compensated pulses can greatly improve the efficiency and reproducibility of NMR experiments. The implementation is based on a measurement of the characteristics of the resonance circuit and does not rely on an experimental optimization of the NMR signal.

    5. Antibiotic Switches

      A Supramolecular Antibiotic Switch for Antibacterial Regulation

      Haotian Bai, Huanxiang Yuan, Chenyao Nie, Bing Wang, Prof. Fengting Lv, Prof. Libing Liu and Prof. Shu Wang

      Article first published online: 26 AUG 2015 | DOI: 10.1002/anie.201504566

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      A supramolecular antibiotic switch to reversibly “turn-on” and “turn-off” its antibacterial activity on demand was developed as a proof-of-concept to regulate antibacterial activity of biotics. The switch relies on the supramolecular assembly and disassembly of a poly(phenylene vinylene) derivative (PPV) with cucurbit[7]uril (CB[7]) that regulates their interactions with bacteria. This strategy does not require any chemical modification on the active sites of the antibacterial agent, and could also regulate the antibacterial activity of classical antibiotics or photosensitizers in photodynamic therapy.

    6. Ligand Design

      Enantioselective Palladium-Catalyzed C[BOND]H Functionalization of Indoles Using an Axially Chiral 2,2′-Bipyridine Ligand

      Xiang Gao, Bo Wu, Wen-Xue Huang, Mu-Wang Chen and Prof. Yong-Gui Zhou

      Article first published online: 26 AUG 2015 | DOI: 10.1002/anie.201504483

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      Get the axial: The title reaction involving diazo compounds was achieved with an axially chiral 2,2′-bipyridine ligand. Moreover, insertion into O[BOND]H bonds of phenols was also realized with up to 99 % ee by using this catalytic system.

  17. Reviews

    1. Spectroscopic Methods

      From Ultrafast Structure Determination to Steering Reactions: Mixed IR/Non-IR Multidimensional Vibrational Spectroscopy

      Dr. Luuk J. G. W. van Wilderen and Prof. Dr. Jens Bredenbeck

      Article first published online: 26 AUG 2015 | DOI: 10.1002/anie.201503155

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      Finger on the pulse: Combining IR with non-IR pulses in multidimensional vibrational spectroscopy creates techniques with possibilities far beyond those of IR experiments alone. These include powerful tools for studying photochemistry, dynamics at surfaces and interfaces, as well as non-equilibrium structural dynamics. This Review discusses important differences between useful pulse sequences and gives examples of their application.

  18. News

  19. Communications

    1. Apoptosis

      Optogenetic Apoptosis: Light-Triggered Cell Death

      Prof. Robert M. Hughes, David J. Freeman, Kelsey N. Lamb, Rebecca M. Pollet, Weston J. Smith and Prof. David S. Lawrence

      Article first published online: 25 AUG 2015 | DOI: 10.1002/anie.201506346

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      Optogenetic Apoptosis: An optogenetic design strategy is described that transforms the aberrant behavior of pro-apoptotic Bax mutants into light-responsive, genetically encoded constructs capable of triggering cell death in response to illumination.

    2. Molecular Biomimetics

      You have full text access to this OnlineOpen article
      Modular Architecture of Protein Binding Units for Designing Properties of Cellulose Nanomaterials

      Jani-Markus Malho, Suvi Arola, Prof. Päivi Laaksonen, Dr. Géza R. Szilvay, Prof. Olli Ikkala and Prof. Markus B. Linder

      Article first published online: 25 AUG 2015 | DOI: 10.1002/anie.201505980

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      Better together: Engineered proteins were combined with nanofibrillated cellulose (gray/brown fibres) to show how a multimodular architecture leads to tuned properties. Two cellulose-binding modules (red and blue structures) were separated by 12-, 24-, or 48-mer linkers (red, green, and blue lines), with an optional multimerizing domain (green structure). The linkers significantly affect the interaction between protein and NFC in the wet colloidal and dry film states.

    3. Green Chemistry

      Nanonickel-Catalyzed Suzuki–Miyaura Cross-Couplings in Water

      Dr. Sachin Handa, Eric D. Slack and Prof. Bruce H. Lipshutz

      Article first published online: 25 AUG 2015 | DOI: 10.1002/anie.201505136

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      Under water: Nickel nanoparticles, formed in situ and used in combination with micellar catalysis, catalyze Suzuki–Miyaura cross-couplings in water under very mild reaction conditions. A wide range of substrates is tolerated, and the reaction medium can be recycled.

    4. Organic Cages

      Porphyrin Boxes: Rationally Designed Porous Organic Cages

      Soonsang Hong, Dr. Md. Rumum Rohman, Dr. Jiangtao Jia, Dr. Youngkook Kim, Dr. Dohyun Moon, Dr. Yonghwi Kim, Dr. Young Ho Ko, Prof. Dr. Eunsung Lee and Prof. Dr. Kimoon Kim

      Article first published online: 25 AUG 2015 | DOI: 10.1002/anie.201505531

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      Find a way: A new strategy for synthesis of shape-persistent organic cages based on porphyrins through rational design is reported. The size of cavities and windows of the organic cages can be modulated using different sized building units while maintaining the topology of the cages.

    5. Polymer Chemistry | Very Important Paper

      Conductive Elastomers with Autonomic Self-Healing Properties

      Kun Guo, Da-Li Zhang, Xiao-Mei Zhang, Prof. Dr. Jian Zhang, Prof. Dr. Li-Sheng Ding, Prof. Dr. Bang-Jing Li and Prof. Dr. Sheng Zhang

      Article first published online: 25 AUG 2015 | DOI: 10.1002/anie.201505790

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      Candidates for smart robotics: Self-healing conductive composites were prepared by connecting single-walled carbon nanotubes (SWCNTs) to a polymer network through host–guest interactions (see picture). The poly(2-hydroxyethyl methacrylate)–SWCNT composite combines bulk electrical conductivity, proximity sensitivity, humidity sensitivity, and autonomic self-healing properties.

    6. Small-Ring Compounds

      Zinc-Catalyzed Alkene Cyclopropanation through Zinc Vinyl Carbenoids Generated from Cyclopropenes

      María J. González, Dr. Javier González, Dr. Luís A. López and Dr. Rubén Vicente

      Article first published online: 25 AUG 2015 | DOI: 10.1002/anie.201505954

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      Open and close! The title reaction provides a convenient and general route to relevant vinylcyclopropane derivatives. Mechanistic studies support the participation of a zinc vinylcarbene intermediate, which may be subsequently involved in a concerted cyclopropanation reaction. This method represents a step towards identifying suitable precursors for the catalytic generation of zinc carbenoids.

    7. Biosynthesis

      Structure, Biosynthesis, and Occurrence of Bacterial Pyrrolizidine Alkaloids

      Olivia Schimming, Dr. Victoria L. Challinor, Dr. Nicholas J. Tobias, Dr. Hélène Adihou, Peter Grün, Laura Pöschel, Dr. Christian Richter, Prof. Dr. Harald Schwalbe and Prof. Dr. Helge B. Bode

      Article first published online: 25 AUG 2015 | DOI: 10.1002/anie.201504877

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      The structures of bacterial pyrrolizidine alkaloids from Xenorhabdus, the pyrrolizixenamides, have been elucidated by two-dimensional NMR spectroscopy and mass spectrometry. Their biosynthesis is shown to involve the bimodular non-ribosomal peptide synthetase PxaA and the unique monooxygenase PxaB.

    8. Radical Cyclization

      Synthesis of Bridged Diketopiperazines by Using the Persistent Radical Effect and a Formal Synthesis of Bicyclomycin

      Tynchtyk Amatov, Dr. Radek Pohl, Dr. Ivana Císařová and Dr. Ullrich Jahn

      Article first published online: 25 AUG 2015 | DOI: 10.1002/anie.201504883

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      Persistent cyclization: A unified radical approach to diverse bridged diketopiperazines was developed by taking advantage of the persistent radical effect. The method allows rapid access to three-dimensional heterocyclic architectures and was applied to a formal synthesis of the antibiotic bicyclomycin.

  20. Reviews

    1. Expanded Genetic Alphabet

      The Expanded Genetic Alphabet

      Dr. Denis A. Malyshev and Prof. Floyd E. Romesberg

      Article first published online: 25 AUG 2015 | DOI: 10.1002/anie.201502890

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      Rule of three: Natural nucleic acids and the genetic information they encode are limited by the use of only four nucleotides that form two base pairs, (d)G-(d)C and d(A)-dT/U. In the past decade, three classes of unnatural base pairs have been developed to a high level of proof-of-concept. This Review summarizes their development and the potentially revolutionary applications that they are now enabling.

  21. Communications

    1. Hydrogen Production

      Silicification-Induced Cell Aggregation for the Sustainable Production of H2 under Aerobic Conditions

      Wei Xiong, Xiaohong Zhao, Genxing Zhu, Changyu Shao, Yaling Li, Prof. Dr. Weimin Ma, Dr. Xurong Xu and Prof. Dr. Ruikang Tang

      Article first published online: 25 AUG 2015 | DOI: 10.1002/anie.201504634

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      Green algae aggregates induced by biomineralization are a novel cell-material hybrid that can sustainably produce hydrogen even under natural aerobic conditions. Its evolution of photobiological hydrogen can be understood by the spatial–functional differentiation of the cells within the aggregate.

  22. Cover Pictures

    1. Unusual H-bond Topology and Bifurcated H-bonds in the 2-Fluoroethanol Trimer

      Dr. Javix Thomas, Dr. Xunchen Liu, Prof. Dr. Wolfgang Jäger and Prof. Dr. Yunjie Xu

      Article first published online: 24 AUG 2015 | DOI: 10.1002/anie.201507430

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      A unique hydrogen-bond topology is reported for the trimer of 2-fluoroethanol by J. Xu et al. in their Communication (10.1002/anie.201505934). Chirped-pulse and cavity-based Fourier transform microwave spectrometry are used to show that the trimer is heterochiral with an open OH⋅⋅⋅OH H-bond arrangement. This result is in stark contrast to trimers of other small alcohols and water which all adopt an OH⋅⋅⋅OH H-bonded ring geometry and exhibit a strong preference for homochirality if the subunits are chiral.

    2. Selective Alcohol Oxidation by a Copper-TEMPO Catalyst: Mechanistic Insights by Simultaneously Coupled Operando EPR/UV-Vis/ATR-IR Spectroscopy

      Dr. Jabor Rabeah, Dr. Ursula Bentrup, Prof. Dr. Reinhard Stößer and Prof. Dr. Angelika Brückner

      Article first published online: 24 AUG 2015 | DOI: 10.1002/anie.201507434

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      To unravel the mechanism of aerobic copper/TEMPO-catalyzed alcohol oxidation, operando ATR-IR, UV/Vis, and EPR spectroscopy are simultaneously coupled for the first time by A. Brückner, J. Rabeah, U. Bentrup, and R. Stößer in their Communication (DOI: 10.1002/anie.201504813). TEMPO activates the oxygen and stabilizes the active (bpy)(NMI)CuII-O2 intermediate, which is formed by electron transfer from the CuI precursor to molecular oxygen.

    3. Polymeric Micelle Assembly for the Smart Synthesis of Mesoporous Platinum Nanospheres with Tunable Pore Sizes

      Yunqi Li, Dr. Bishnu Prasad Bastakoti, Dr. Victor Malgras, Dr. Cuiling Li, Jing Tang, Prof. Jung Ho Kim and Prof. Yusuke Yamauchi

      Article first published online: 24 AUG 2015 | DOI: 10.1002/anie.201507608

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      A polymeric micelle assembly is used for the fabrication of well-dispersed mesoporous Pt nanospheres by Y. Yamauchi, B. P. Bastakoti et al. in their Communication (DOI: 10.1002/anie.201505232). A core–shell–corona triblock copolymer [poly(styrene-b-2-vinylpyridine-b-ethylene oxide), PS-b-P2VP-b-PEO] is employed as the pore-directing agent. The negatively charged Pt species preferably interact with the protonated P2VP blocks while the free PEO chains prevent the aggregation of the Pt nanospheres.

    4. Regioregular Synthesis of Azaborine Oligomers and a Polymer with a syn Conformation Stabilized by N[BOND]H⋅⋅⋅π Interactions

      Andrew W. Baggett, Fang Guo, Dr. Bo Li, Prof. Dr. Shih-Yuan Liu and Prof. Dr. Frieder Jäkle

      Article first published online: 24 AUG 2015 | DOI: 10.1002/anie.201507513

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      Regioregular 1,2-azaborine oligomers and a polymer were synthesized by F. Jäkle, S.-Y. Liu et al. As described in their Communication (10.1002/anie.201504822), these materials exhibit bathochromic shifts of absorption and emission maxima with increasing chain length that is consistent with a long effective conjugation length. An X-ray crystal structure of the dimer and computational studies reveal an N[BOND]H⋅⋅⋅π interaction between neighboring 1,2-azaborine units as a conformation-defining element that favors a coplanar arrangement.

    5. Very Important Paper

      Orthogonal Light-Induced Self-Assembly of Nanoparticles using Differently Substituted Azobenzenes

      Dr. Debasish Manna, Dr. Thumu Udayabhaskararao, Dr. Hui Zhao and Dr. Rafal Klajn

      Article first published online: 24 AUG 2015 | DOI: 10.1002/anie.201507476

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      Precise control of the assembly of selected components within complex mixtures is a challenging task. In their Communication (DOI: 10.1002/anie.201502419), R. Klajn et al. approach this challenge by decorating the surfaces of differently sized nanoparticles with two distinct azobenzenes that isomerize upon exposure to different wavelengths of light. The cover illustrates how ultraviolet and blue light can be used to selectively assemble large and small nanoparticles, respectively (Cover image: Ella Marushchenko).

    6. A Strategy to Control the Reactivation of Frustrated Lewis Pairs from Shelf-Stable Carbene Borane Complexes

      Dr. Yoichi Hoshimoto, Takuya Kinoshita, Prof. Dr. Masato Ohashi and Prof. Dr. Sensuke Ogoshi

      Article first published online: 24 AUG 2015 | DOI: 10.1002/anie.201507437

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      A magician is looking into his crystal ball to read the future of a Lewis acid–base adduct. When his hand (an external stimulus) catches and rotates the phosphine oxide moiety, a highly active frustrated Lewis pair is formed in a process that is studied by S. Ogoshi, Y. Hoshimoto et al. in their Communication (DOI: 10.1002/anie.201505974). This reactivation of frustration (and the high reactivity) is shown as a cracking of the crystal ball.

    7. Cyclic [2]Catenane Dimers, Trimers, and Tetramers

      Yi-Wei Wu, Shun-Te Tung, Prof. Chien-Chen Lai, Yi-Hung Liu, Prof. Shie-Ming Peng and Prof. Sheng-Hsien Chiu

      Article first published online: 24 AUG 2015 | DOI: 10.1002/anie.201507436

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      Dimeric, trimeric, and tetrameric cyclic [2]catenanes can be synthesized in a one-pot sodium-ion-templated process from a diamine and a tetraaldehyde. In their Communication (DOI: 10.1002/anie.201505903), S.-H. Chiu and co-workers describe the isolation and characterization of these oligomeric cyclic [2]catenanes as stable, covalently linked compounds after reduction and methylation.

  23. Communications

    1. Electrocatalysis

      Blending Cr2O3 into a NiO–Ni Electrocatalyst for Sustained Water Splitting

      Ming Gong, Dr. Wu Zhou, Michael James Kenney, Rich Kapusta, Sam Cowley, Dr. Yingpeng Wu, Dr. Bingan Lu, Dr. Meng-Chang Lin, Dr. Di-Yan Wang, Dr. Jiang Yang, Prof. Bing-Joe Hwang and Prof. Hongjie Dai

      Article first published online: 24 AUG 2015 | DOI: 10.1002/anie.201504815

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      A triphase electrocatalyst of Cr2O3-blended NiO coating on Ni nanocores (CrNN catalyst) synthesized on metal-foam substrates showed superior activity and stability for the hydrogen-evolution reaction in basic solutions. Using the CrNN catalyst, sustained electrolysis of water was achieved at a voltage lower than 1.5 V for at least 500 hours.

    2. Halogenation

      Selective Ruthenium-Catalyzed Hydrochlorination of Alkynes: One-Step Synthesis of Vinylchlorides

      Dr. Sylvie Dérien, Dr. Hubert Klein and Dr. Christian Bruneau

      Article first published online: 24 AUG 2015 | DOI: 10.1002/anie.201505144

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      A new addition: An efficient and straightforward access to vinylchlorides is reported. This selective ruthenium-catalyzed alkyne hydrochlorination proceeds in excellent yields under mild reaction conditions by the syn addition of HCl. cod=1,5-cyclooctadiene, Cp*=C5Me5, DCE=1,2-dichloroethane.

  24. Cover Pictures

    1. Switchable Lipids: Conformational Change for Fast pH-Triggered Cytoplasmic Delivery

      Warren Viricel, Dr. Amira Mbarek and Prof. Dr. Jeanne Leblond

      Article first published online: 24 AUG 2015 | DOI: 10.1002/anie.201507428

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      Liposomes must protect their cargo during delivery and then release it quickly and selectively at the target site. In their Communication (DOI: 10.1002/anie.201504661), J. Leblond et al. present the development of switchable liposomes that exploit the acidification that occurs after endocytosis. These liposomes are stable for months under physiological conditions and release their content in less than 15 min at acidic pH values. This approach drastically improves drug delivery to the cytosol.