Chemistry - A European Journal

Cover image for Vol. 16 Issue 37

October 4, 2010

Volume 16, Issue 37

Pages 11193–11495

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Communications
    8. Full Papers
    9. Preview
    1. Cover Picture: A Gram-Scale Batch and Flow Total Synthesis of Perhydrohistrionicotoxin (Chem. Eur. J. 37/2010) (page 11193)

      Dr. Malte Brasholz, Dr. James M. Macdonald, Dr. Simon Saubern, Dr. John H. Ryan and Prof. Dr. Andrew B. Holmes

      Article first published online: 24 SEP 2010 | DOI: 10.1002/chem.201090183

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      Biologically valuable histrionicotoxin spiropiperidine alkaloids are found in the Colombian poison arrow frog Dendrobates histrionicus (shown on the cover). In their Full Paper on page 11471 ff., J. H. Ryan et al. describe efforts to synthesize an unnatural analogue, perhydrohistrionicotoxin, by combining conventional with microreactor techniques. (Photograph of Dendrobates histrionicus by Mauricio Rivera. Design by Martin Kowalski.)

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Communications
    8. Full Papers
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    1. Inside Cover: Hydrogen-Atom Abstraction from Methane by Stoichiometric Vanadium–Silicon Heteronuclear Oxide Cluster Cations (Chem. Eur. J. 37/2010) (page 11194)

      Dr. Xun-Lei Ding, Yan-Xia Zhao, Xiao-Nan Wu, Zhe-Chen Wang, Jia-Bi Ma and Prof. Sheng-Gui He

      Article first published online: 24 SEP 2010 | DOI: 10.1002/chem.201090184

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      Time-of-flight mass spectrometry and density functional theory were used to study the reactions of vanadium–silicon heteronuclear oxide cluster cations with methane. In their Full Paper on page 11463 ff., S.-G. He et al. demonstrate that the stoichiometric oxide clusters [V2O5(SiO2)1–4]+ and [(V2O5)2SiO2]+, which contain terminal-oxygen-centered radicals (Ot.) responsible for high C[BOND]H activation, are able to activate methane under near-room-temperature conditions.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Communications
    8. Full Papers
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    1. Graphical Abstract: Chem. Eur. J. 37/2010 (pages 11197–11205)

      Article first published online: 24 SEP 2010 | DOI: 10.1002/chem.201090185

  4. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Communications
    8. Full Papers
    9. Preview
  5. Review

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Communications
    8. Full Papers
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    1. Homogeneous Catalysis

      Oxidative Coupling of Aromatic Substrates with Alkynes and Alkenes under Rhodium Catalysis (pages 11212–11222)

      Prof. Dr. Tetsuya Satoh and Prof. Dr. Masahiro Miura

      Article first published online: 25 AUG 2010 | DOI: 10.1002/chem.201001363

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      Controlled fusion: Aromatic substrates with oxygen- and nitrogen-containing substituents undergo oxidative coupling with alkynes and alkenes under rhodium catalysis through regioselective C[BOND]H bond cleavage. Coordination of the substituents to the rhodium center is the key to activate the C[BOND]H bonds effectively. Various fused-ring systems can be constructed through these reactions.

  6. Communications

    1. Top of page
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    4. Graphical Abstract
    5. News
    6. Review
    7. Communications
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    1. Aromatic Ring Umpolung

      An Oxidative Prins–Pinacol Tandem Process and its Application to the synthesis of (−)-Platensimycin (pages 11224–11228)

      Marc-André Beaulieu, Dr. Cyrille Sabot, Nabil Achache, Kimiaka C. Guérard and Prof. Dr. Sylvain Canesi

      Article first published online: 25 AUG 2010 | DOI: 10.1002/chem.201001813

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      Center stage: An oxidative Prins–pinacol tandem process mediated by a hypervalent iodine reagent has been accomplished. The strategy allows rapid access to highly functionalized spirocyclic cores (see scheme) present in many natural products. A first application to the formal synthesis of (−)-platensimycin has been achieved.

    2. Synthetic Methodology

      A Concise Route to α′-Methoxy-γ-pyrones and Verticipyrone Based Upon the Desymmetrization of α,α′-Dimethoxy-γ-pyrone (pages 11229–11232)

      Dr. Michaël De Paolis, Helèna Rosso, Matthias Henrot, Prof. Dr. Cristina Prandi, Florent d'Herouville and Dr. Jacques Maddaluno

      Article first published online: 19 AUG 2010 | DOI: 10.1002/chem.201001780

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      Two steps is the rule: A concise synthesis of versatile α′-methoxy-γ-pyrones (see scheme) is described that uses an innovative desymmetrization of α,α′-dimethoxy-γ-pyrone, relying upon conjugate addition of nucleophiles. This new strategy is applied to the preparation of α-methyl- and α-carboxaldehyde-α′-methoxy-γ-pyrones and to a short synthesis of verticipyrone.

    3. Synthesis Design

      Total Synthesis and Antibiotic Activity of Dehydrohomoplatencin (pages 11233–11236)

      Dennis C. J. Waalboer, Stefan H. A. M. Leenders, Dr. Tanja Schülin-Casonato, Dr. Floris L. van Delft and Prof. Dr. Floris P. J. T. Rutjes

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.201001744

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      Expanding antibiotics: A concise synthesis of dehydrohomoplatencin, a novel derivative of the naturally occurring antibiotic platencin, has been realized (see scheme). Notably, the synthesis of the ketolide portion of the molecule was achieved in only two exceedingly simple steps. Compared to platencin, dehydrohomoplatencin showed virtually equipotent antibacterial activity against Gram-positive bacteria and may serve as a novel lead structure for the development of new antibiotics.

    4. Organocatalysis

      Merging Organocatalysis with an Indium(III)-Mediated Process: A Stereoselective α-Alkylation of Aldehydes with Allylic Alcohols (pages 11237–11241)

      Montse Guiteras Capdevila, Dr. Fides Benfatti, Dr. Luca Zoli, Dr. Marco Stenta and Prof. Pier Giorgio Cozzi

      Article first published online: 18 AUG 2010 | DOI: 10.1002/chem.201001693

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      Curiosity killed the CAT…ions! The use of stabilized cationic intermediates can be considered as a new frontier in the development of stereoselective reactions. An organocatalytic procedure mediated by the MacMillan imidazolidinone catalyst was coupled with an InBr3-mediated process for the development of a novel stereoselective allylation reaction of aldehydes. Up to 98 % ee and up to 5:1 d.r. were obtained in the process.

    5. Radical Clusters

      Oxidative Perhydroxylation of [closo-B12H12]2− to the Stable Inorganic Cluster Redox System [B12(OH)12]2−/.−: Experiment and Theory (pages 11242–11245)

      Dr. Nguyen Van, Dr. Ioannis Tiritiris, Prof. Dr. Rainer F. Winter, Dr. Biprajit Sarkar, Dr. Priti Singh, Dr. Carole Duboc, Dr. Alvaro Muñoz-Castro, Prof. Dr. Ramiro Arratia-Pérez, Prof. Dr. Wolfgang Kaim and Prof. Dr. Thomas Schleid

      Article first published online: 19 AUG 2010 | DOI: 10.1002/chem.201001374

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      It′s radical: A surprisingly simple reaction converts the normally inert prototypical hydridoborate cluster [closo-B12H12]2− not only to [closo-B12(OH)12]2− but also, at less-elevated temperatures, to the new [hypocloso-B12(OH)12].− radical anion (see figure). Both approximately icosahedral closo and hypocloso cluster ions were structurally characterized as the cesium salts and their properties were assessed experimentally and theoretically.

    6. Hydroarylation

      Calcium-Catalyzed Hydroarylation of Alkenes at Room Temperature (pages 11246–11249)

      Prof. Dr. Meike Niggemann and Dr. Nicola Bisek

      Article first published online: 20 AUG 2010 | DOI: 10.1002/chem.201001375

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      Calcium-catalyst gaining ground: A variety of electron-poor, electron-rich, and trisubstituted styrene derivatives were reacted to give the desired diarylalkanes within less than an hour at room temperature in the presence of 2.5 mol % of Ca(NTf2)2/Bu4NPF6 (see scheme). Additionally, the highly reactive calcium catalyst was successfully applied for the hydroarylation of dienes and even trisubstituted olefins.

    7. Synthesis Design

      The Use of Tethered Addends to Decrease the Number of Isomers of Bisadduct Analogues of PCBM (pages 11250–11253)

      Ricardo K. M. Bouwer and Prof. Dr. Jan C. Hummelen

      Article first published online: 20 AUG 2010 | DOI: 10.1002/chem.201000537

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      Roped in: The number of isomers present in the bisadduct analogue PCBM (bis-PCBM; PCBM=phenyl-C61-butyric acid methyl ester), a recently introduced acceptor for bulk heterojunction organic photovoltaic devices, has been reduced to seven by linking two tosylhydrazone addends with an ethylene glycol tether and reacting them with C60.

    8. Antitumor Agents

      A “Neck-Formation” Strategy for an Antiquenching Magnetic/Upconversion Fluorescent Bimodal Cancer Probe (pages 11254–11260)

      Feng Chen, Shengjian Zhang, Prof. Wenbo Bu, Xiaohang Liu, Yu Chen, Qianjun He, Min Zhu, Prof. Lingxia Zhang, Liangping Zhou, Prof. Weijun Peng and Prof. Jianlin Shi

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.201000525

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      Up to the neck! Bio-safe upconversion fluorescent nanocrystals (NaYF4:Er,Yb) and biocompatible superparamagnetic iron oxide nanocrystals (SPION) were effectively combined by means of a general “neck-formation” strategy, forming a size-controlled, Cd2+- and Gd3+-free, silica-shielded, magnetic upconversion fluorescent oligomer (SMUFO), bimodal cancer probe that offers high resistance to photoquenching as well as a synergistic T2-weighted magnetic resonance enhanced effect (see graphic).

    9. Metallaoxetanes

      Rhodium Mediated C[BOND]H Bond Functionalisation Leading to Carboxylate Derivatives (pages 11261–11265)

      Dr. Cristina Tejel, Dr. M. Pilar del Río, Dr. José A. López and Prof. Miguel A. Ciriano

      Article first published online: 18 AUG 2010 | DOI: 10.1002/chem.201001453

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      Selective functionalisation of 1,5-cyclooctadiene, either to a carboxylic acid or to a γ-lactone, is achieved by a novel sequence of reactions involving quantitative oxygenation with oxygen and C[BOND]C coupling with carbon monoxide (see graphic). The rhodium hydroxy–alkyl–allyl complex shown is the active intermediate that promotes the elimination of the organic compounds.

    10. Nanostructures

      Strategic Synthesis of Hierarchical TiO2 Microspheres with Enhanced Photocatalytic Activity (pages 11266–11270)

      Zhaoke Zheng, Prof. Dr. Baibiao Huang, Xiaoyan Qin, Prof. Xiaoyang Zhang and Prof. Dr. Ying Dai

      Article first published online: 25 AUG 2010 | DOI: 10.1002/chem.201001280

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      Superior hierarchy: A facile method was developed to synthesize hierarchical TiO2 microspheres with nanotubular and dendritic structures. Owing to the high surface area and open porous networks, the synthesized TiO2 microspheres exhibit a superior photocatalytic activity. This method provides a new strategy for the synthesis of hierarchical materials with particular morphologies.

    11. Enantioselectivity

      Hg(OTf)2–BINAPHANE-Catalyzed Enantioselective Anilino Sulfonamide Allyl Alcohol Cyclization (pages 11271–11274)

      Dr. Hirofumi Yamamoto, Elisabeth Ho, Dr. Kosuke Namba, Dr. Hiroshi Imagawa and Prof. Dr. Mugio Nishizawa

      Article first published online: 20 AUG 2010 | DOI: 10.1002/chem.201001656

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      Chiral ligands: Hg(OTf)2-catalyzed cyclization of anilino sulfonamide allyl alcohol is described; this reaction gives 2-vinyl indoline derivatives in good yields and excellent enantioselectivity by using a chiral BINAPHANE ligand (see scheme).

  7. Full Papers

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Communications
    8. Full Papers
    9. Preview
    1. Cyclopropanes

      From Furan to Molecular Stairs: Syntheses, Structural Properties, and Theoretical Investigations of Oligocyclic Oligoacetals (pages 11276–11288)

      Dipl.-Chem. Tobias F. Schneider, Dipl.-Chem. Johannes Kaschel, Shahid I. Awan, Dr. Birger Dittrich and Dr. Daniel B. Werz

      Article first published online: 9 SEP 2010 | DOI: 10.1002/chem.201000468

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      Not a ladder, but stairs: A repetition of a three-step sequence consisting of twofold cyclopropanation, reduction, and oxidation starting from furan leads to anti-oligoannelated tetrahydrofuran moieties. The structures were investigated by X-ray diffraction and computational methods (see figure).

    2. Supramolecular Chemistry

      Surprising Properties of a Furo-Furanone (pages 11289–11299)

      Prof. Dr. Gion Calzaferri, Dr. Dominik Brühwiler, Dr. Tao Meng, Dr. Le-Quyenh Dieu, Dr. Vladimir L. Malinovskii and Prof. Dr. Robert Häner

      Article first published online: 19 AUG 2010 | DOI: 10.1002/chem.201000728

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      Nanochannel: Insertion of molecules into a nanochannel helps us to understand weak intermolecular interactions. Molecules that form different kinds of aggregates in solution arrange into well-oriented molecular aggregates when embedded in the nanochannels of zeolite L (see graphic).

    3. Lipid-Binding Proteins

      Site-Specific Investigation of the Steady-State Kinetics and Dynamics of the Multistep Binding of Bile Acid Molecules to a Lipid Carrier Protein (pages 11300–11310)

      Dr. Clelia Cogliati, Dr. Laura Ragona, Dr. Mariapina D'Onofrio, Prof. Ulrich Günther, Dr. Sara Whittaker, Dr. Christian Ludwig, Dr. Simona Tomaselli, Dr. Michael Assfalg and Prof. Henriette Molinari

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.201000498

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      Stuck together: Line-shape analysis provides a direct view of the mechanism and the kinetic rate constants for the binding events in a complex macromolecular system (see figure). Two probes (1H, 15N) provide information on the effect of binding along the entire titration pathway. The two neighbouring nuclei experience the same kinetic mechanism, overcoming a possible lack of resolution in one dimension.

    4. Microreactors

      Palladium Membrane-Installed Microchannel Devices for Instantaneous Suzuki–Miyaura Cross-Coupling (pages 11311–11319)

      Dr. Yoichi M. A. Yamada, Toshihiro Watanabe, Tomohiko Beppu, Naoshi Fukuyama, Kaoru Torii and Prof. Dr. Yasuhiro Uozumi

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.201000511

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      Obtained in the membrane: Instantaneous catalytic carbon–carbon bond-forming reactions were achieved in catalytic membrane-installed microchannel devices that have a polymeric Pd membrane. The Suzuki–Miyaura reaction was performed with these devices to give quantitative yields of the corresponding products within 5 s of residence time (see image).

    5. Vesicle Formation

      Reverse-Vesicle Formation of Organic–Inorganic Polyoxometalate-Containing Hybrid Surfactants with Tunable Sizes (pages 11320–11324)

      Dr. Jie Zhang, Dr. Yu-Fei Song, Prof. Leroy Cronin and Prof. Tianbo Liu

      Article first published online: 19 AUG 2010 | DOI: 10.1002/chem.201000794

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      Getting in shape: The formation of reverse vesicles of polyoxometalate-containing hybrid surfactants in nonpolar medium was achieved by titration with toluene (see scheme; TBA=nBu4N). The impact of the toluene content and the alkyl chain length of the hybrid surfactant were investigated by light scattering and transmission electron microscopy.

    6. Amine Catalysis

      Synthesis of 2-Isoxazolines: Enantioselective and Racemic Methods Based on Conjugate Additions of Oximes (pages 11325–11339)

      Antti Pohjakallio, Prof. Petri M. Pihko and Ulla M. Laitinen

      Article first published online: 19 AUG 2010 | DOI: 10.1002/chem.201000861

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      A salty solution: Acidic anilinium salts catalyze the direct formation of racemic 2-isoxazolines from enals and oximes by means of consecutive oxime conjugate-addition and oxime-transfer reactions (see scheme). This process can also be rendered enantioselective.

    7. π-Conjugated Systems

      3,4-Dithiaphosphole and 3,3′,4,4′-Tetrathia-1,1′-Biphosphole π-Conjugated Systems: S Makes the Impact (pages 11340–11356)

      Dr. Omrane Fadhel, Dr. Zoltán Benkö, Michael Gras, Valérie Deborde, Damien Joly, Christophe Lescop, Prof. László Nyulászi, Prof. Muriel Hissler and Prof. Régis Réau

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.201001463

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      The S effect: Introducing S atoms at the 3,4-positions of phospholes (see figure) results in many appealing properties: a decrease of the HOMO–LUMO separation, electron affinity enhancement, and the possibility to perform multiaddressing by means of chemoselective transformations of the heteroatoms.

    8. Metallaboranes

      From Metallaborane to Borylene Complexes: Syntheses and Structures of Triply Bridged Ruthenium and Tantalum Borylene Complexes (pages 11357–11366)

      K. Geetharani, Shubhankar Kumar Bose, Babu Varghese and Dr. Sundargopal Ghosh

      Article first published online: 20 AUG 2010 | DOI: 10.1002/chem.201001208

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      Arachnophilia: Mild reaction of arachno-[(Cp*RuCO)2B2H6] with [Fe2(CO)9] and [Mn2(CO)10] yielded triply bridged borylene species 1 and 2 and bis-borylene complexes 3 and [{(μ3-BH)(Cp*Ru)Fe(CO)3}2(μ-CO)]. The first bridged tantalum borylene complex, 4, was synthesized by the reaction of [(Cp*Ta)2B4H8(μ-BH4)] with [Fe2(CO)9] at ambient temperature (see picture).

      Corrected by:

      Corrigendum: Corrigendum: From Metallaborane to Borylene Complexes: Syntheses and Structures of Triply Bridged Ruthenium and Tantalum Borylene Complexes

      Vol. 16, Issue 48, 14224, Article first published online: 5 JAN 2011

    9. Asymmetric Catalysis

      Investigation of Lewis Acid versus Lewis Base Catalysis in Asymmetric Cyanohydrin Synthesis (pages 11367–11375)

      Prof. Michael North, Marta Omedes-Pujol and Courtney Williamson

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.201001078

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      To be (Lewis acid catalysed) or not to be, that is the question: A Hammett analysis based on the structure of aldehyde substrates allows the determination of the relative importance of Lewis acid and Lewis base catalysis. The methodology is applied to asymmetric cyanohydrin synthesis catalysed by four complexes and shows that they differ in the degree of Lewis acid catalysis (see figure). Based on the results, it was predicted, and experimentally verified, that an aluminium-based catalyst would accept ketones as substrates.

    10. Copolymerization

      A Joint Experimental/Theoretical Investigation of the Statistical Olefin/Conjugated Diene Copolymerization Catalyzed by a Hemi-Lanthanidocene [(Cp*)(BH4)LnR] (pages 11376–11385)

      Dr. Lionel Perrin, Dr. Fanny Bonnet, Dr. Thomas Chenal, Prof. Dr. Marc Visseaux and Prof. Dr. Laurent Maron

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.200903455

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      Copolymerization catalyzed: Statistical copolymerization of a mono- and a diene was achieved by using a borohydride hemilanthanidocene (see figure). Analysis of the microstructure of the copolymers revealed successive short sequences of ethylene/ethylene, 1,4-isoprene/ethylene, and 1,4-isoprene/1,4-isoprene. DFT calculations of the initial steps in the copolymerization provides some insight into the catalyst's activity and selectivity.

    11. Surface Chemistry

      Probing Surface Sites of TiO2: Reactions with [HRe(CO)5] and [CH3Re(CO)5] (pages 11386–11398)

      Rodrigo J. Lobo-Lapidus and Bruce C. Gates

      Article first published online: 19 AUG 2010 | DOI: 10.1002/chem.201000267

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      Adsorb and release: [HRe(CO)5] and [CH3Re(CO)5] were used as probes to elucidate the reactivity of the surface of the anatase phase of titania (see scheme). The adsorbed species were characterized by EXAFS and IR spectroscopy. During the adsorption, OH groups were found to react with the probes and form carbonates and water. This information was used to provide a ranking of the various OH groups based on their reactivity and ease of removal by thermal treatment.

    12. Catalysis

      Do Dynamic Effects Play a Significant Role in Enzymatic Catalysis? A Theoretical Analysis of Formate Dehydrogenase (pages 11399–11411)

      Dr. Maite Roca, Dr. Mónica Oliva, Dr. Raquel Castillo, Prof. Vicente Moliner and Prof. Iñaki Tuñón

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.201000635

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      Molecular dynamic trajectories: A theoretical study of the protein dynamics effects on hydride transfer between formate anions and nicotinamide adenine dinucleotide (NAD+) catalyzed by formate dehydrogenase (FDH) has allowed the estimation of a contribution to catalysis of 0.5 kcal mol−1 (see figure). This result, although small, is not negligible considering the low efficiency of FDH. The results also reveal how the relative movements of some amino acids precede and promote the chemical reaction.

    13. Nanomaterials

      General Strategy for a Large-Scale Fabric with Branched Nanofiber–Nanorod Hierarchical Heterostructure: Controllable Synthesis and Applications (pages 11412–11419)

      Meng Shang, Prof. Wenzhong Wang, Wenzong Yin, Jia Ren, Songmei Sun and Dr. Ling Zhang

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.201000639

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      The power of magic fabric: A family of branched hierarchical heterostructure fabrics can be synthesized on a large scale by a general approach that combines the electrospinning technique with a controllable hydrothermal method (see picture; MO=metal oxide, HMT=hexamethylenetetramine). The fabric exhibits high mobility of charge carriers and enhanced photocatalytic activity.

    14. Pt–DNA Adducts

      Photolysis and Thermolysis of Platinum(IV) 2,2′-Bipyridine Complexes Lead to Identical Platinum(II)–DNA Adducts (pages 11420–11431)

      Christophe Loup , Dr. Ana Tesouro Vallina , Dr. Yannick Coppel , Dr. Ulla Létinois , Prof. Dr. Yasuo Nakabayashi , Dr. Bernard Meunier , Prof. Dr. Bernhard Lippert and Dr. Geneviève Pratviel 

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.201000850

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      Spontaneous reduction of two PtIV complexes containing a 2,2′-bipyridine (bpy) ligand to the corresponding PtII complexes occurs not only under light irradiation but also upon moderate heating (37 or 50 °C) in the dark. In the presence of DNA the PtII complexes readily form (bpy)Pt–DNA adducts (see scheme).

    15. Carbenes

      Electronic Tuning of a Carbene Center via Remote Chemical Induction, and Relevant Effects in Catalysis (pages 11432–11442)

      Dr. Vincent César, Dr. Noël Lugan and Dr. Guy Lavigne

      Article first published online: 6 SEP 2010 | DOI: 10.1002/chem.201000870

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      The right tone: The donor properties of a metal-bound NHC ligand possessing a malonate backbone can be finely tuned by simple addition of a selected electrophile interacting with the remote nucleophilic part of the ligand in the outer coordination sphere of the complex. Relevant consequences on the catalytic behavior of these species were observed and rationalized on the basis of two test catalytic reactions.

    16. Fluorinated Amines

      Highly Diastereoselective Synthesis of α-Difluoromethyl Amines from N-tert-Butylsulfinyl Ketimines and Difluoromethyl Phenyl Sulfone (pages 11443–11454)

      Dr. Jun Liu and Prof. Dr. Jinbo Hu

      Article first published online: 19 AUG 2010 | DOI: 10.1002/chem.201000893

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      Difluoromethylation of ketimines: A highly efficient and stereoselective difluoromethylation of N-tert-butylsulfinyl ketimines has been achieved with an in situ generated PhSO2CF2 anion, which provides a powerful synthetic method for the preparation of structurally diverse homochiral α-difluoromethyl tertiary carbinamines (see scheme). The use of an appropriate base, such as potassium hexamethyldisilazide (KHMDS), was crucial in these nucleophilic difluoromethylation reactions.

    17. Gold Nanocatalysis

      An Atomic-Level Strategy for Unraveling Gold Nanocatalysis from the Perspective of Aun(SR)m Nanoclusters (pages 11455–11462)

      Dr. Yan Zhu, Huifeng Qian and Prof. Rongchao Jin

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.201001086

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      All that glitters: An atomic-level strategy is adopted to reveal the fundamentals of nanogold catalysis for styrene oxidation by using the atomically monodisperse Aun(SR)m/support nanoclusters as catalysts (see scheme).

      Corrected by:

      Corrigendum: Corrigendum: An Atomic-Level Strategy for Unraveling Gold Nanocatalysis from the Perspective of Aun(SR)m Nanoclusters

      Vol. 17, Issue 47, 13117, Article first published online: 14 NOV 2011

    18. Methane Activation

      Hydrogen-Atom Abstraction from Methane by Stoichiometric Vanadium–Silicon Heteronuclear Oxide Cluster Cations (pages 11463–11470)

      Dr. Xun-Lei Ding, Yan-Xia Zhao, Xiao-Nan Wu, Zhe-Chen Wang, Jia-Bi Ma and Prof. Sheng-Gui He

      Article first published online: 8 SEP 2010 | DOI: 10.1002/chem.201001297

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      Art of abstraction: Hydrogen abstraction reactions over the stoichiometric V–Si heteronuclear oxide cluster cations [(V2O5)n(SiO2)m]+ (n=1, m=1–4; n=2, m=1) are identified. Terminal-oxygen-centered radicals (Ot.) in these clusters are the active sites for CH4 activation. The Ot. radicals are bonded to Si rather than V in [V2O5(SiO2)1–4]+ clusters (see figure). The multivalence states of V (+5 and +4) are also found in some of the cluster isomers.

    19. Total Synthesis

      A Gram-Scale Batch and Flow Total Synthesis of Perhydrohistrionicotoxin (pages 11471–11480)

      Dr. Malte Brasholz, Dr. James M. Macdonald, Dr. Simon Saubern, Dr. John H. Ryan and Prof. Dr. Andrew B. Holmes

      Article first published online: 8 SEP 2010 | DOI: 10.1002/chem.201001435

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      The best of both worlds: A combined flow and batch approach leads to the spirocyclic poison frog alkaloid (−)-perhydrohistrionicotoxin on a gram scale. Microreactor processing of key synthetic intermediates, including organometallic species, gave similar yields and stereoselectivites to conventional round-bottomed flask procedures, but at milder temperatures, in shorter reaction times and in a telescoped fashion (see scheme).

    20. Hydrozincite

      In and Ex Situ Studies of the Formation of Layered Microspherical Hydrozincite as Precursor for ZnO (pages 11481–11488)

      Marko Bitenc, Peter Podbršček, Dr. Pavo Dubček, Dr. Sigrid Bernstorff, Prof. Dr. Goran Dražić, Prof. Dr. Bojan Orel, Prof. Dr. Stane Pejovnik and Dr. Zorica Crnjak Orel

      Article first published online: 19 AUG 2010 | DOI: 10.1002/chem.201001411

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      Two-minute mechanism: The formation of a layered hydrozincite precursor was studied with the combination of in situ and ex situ techniques. The growth mechanism follows the “nonclassical crystallization” concept of a rapid (≈2 min) self-assembling mechanism (see graphic).

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    4. Graphical Abstract
    5. News
    6. Review
    7. Communications
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      Preview: Chem. Eur. J. 38/2010 (page 11495)

      Article first published online: 24 SEP 2010 | DOI: 10.1002/chem.201090187

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