Angewandte Chemie International Edition

Cover image for Vol. 50 Issue 51

December 16, 2011

Volume 50, Issue 51

Pages 12111–12365

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. Corrigendum
    7. News
    8. Author Profile
    9. News
    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Cover Picture: Hierarchically Assembled ZnO Nanocrystallites for High-Efficiency Dye-Sensitized Solar Cells (Angew. Chem. Int. Ed. 51/2011) (page 12111)

      Nafiseh Memarian, Isabella Concina, Antonio Braga, Seyed Mohammad Rozati, Alberto Vomiero and Giorgio Sberveglieri

      Article first published online: 5 OCT 2011 | DOI: 10.1002/anie.201106766

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      Hierarchically structured ZnO photoanodes for dye-sensitized solar cells can be fabricated by spray pyrolysis, as shown by A. Vomiero and co-workers in their Communication on page 12 321 ff. These photoanodes can achieve a top photoconversion efficiency of 7.5 %, as for ZnO-based cells. The technique is simple, cheap, and it can be scaled up to cover large areas.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. Corrigendum
    7. News
    8. Author Profile
    9. News
    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Inside Cover: Catalytic Redox Reactions in the CO/N2O System Mediated by the Bimetallic Oxide-Cluster Couple AlVO3+/AlVO4+ (Angew. Chem. Int. Ed. 51/2011) (page 12112)

      Dr. Zhe-Chen Wang, Dipl.-Chem. Nicolas Dietl, Dipl.-Chem. Robert Kretschmer, Dr. Thomas Weiske, Dr. Maria Schlangen and Prof. Dr. Helmut Schwarz

      Article first published online: 4 OCT 2011 | DOI: 10.1002/anie.201106676

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      No need to look into the crystal ball mass spectrometric studies and computational methods reveal for the first time that a bimetallic oxide cluster couple, AlVO3+/AlVO4+, provides an ideal model for the room-temperature catalytic oxidation of CO by N2O. In their Communication on page 12 351 ff. H. Schwarz, M. Schlangen, and co-workers show that the overall catalytic process is promoted by the radical oxygen center of the Al[BOND]Oterminal. unit and not by the V[DOUBLE BOND]Oterminal moiety.

  3. Back Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. Corrigendum
    7. News
    8. Author Profile
    9. News
    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Back Cover: Active-Metal Template Synthesis of a Molecular Trefoil Knot (Angew. Chem. Int. Ed. 51/2011) (page 12366)

      Dr. Perdita E. Barran, Harriet L. Cole, Dr. Stephen M. Goldup, Prof. David A. Leigh, Dr. Paul R. McGonigal, Dr. Mark D. Symes, Jhenyi Wu and Michael Zengerle

      Article first published online: 4 OCT 2011 | DOI: 10.1002/anie.201106646

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      The marriage of coordination chemistry and catalysis enables metal ions to work in partnership in the active-template synthesis of the smallest molecular trefoil knot reported to date. In their Communication on page 12 280 ff., D. A. Leigh et al. describe how one copper(I) ion entangles an acyclic building block to create a loop in the ligand whilst a second copper(I) ion gathers the ligand′s reactive end groups, threads the loop, and catalyzes the covalent capture of the 76-atom knot by an alkyne–azide “click” reaction.

  4. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. Corrigendum
    7. News
    8. Author Profile
    9. News
    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Graphical Abstract: Angew. Chem. Int. Ed. 51/2011 (pages 12115–12128)

      Article first published online: 14 DEC 2011 | DOI: 10.1002/anie.201190107

  5. Corrigendum

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. Corrigendum
    7. News
    8. Author Profile
    9. News
    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
    15. Preview
    1. You have free access to this content
      Corrigendum: Hydrogen-Independent Reductive Transformation of Carbohydrate Biomass into γ-Valerolactone and Pyrrolidone Derivatives with Supported Gold Catalysts (page 12128)

      Xian-Long Du, Lin He, She Zhao, Dr. Yong-Mei Liu, Prof. Dr. Yong Cao, Prof. Dr. He-Yong He and Prof. Kang-Nian Fan

      Article first published online: 14 DEC 2011 | DOI: 10.1002/anie.201107773

  6. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. Corrigendum
    7. News
    8. Author Profile
    9. News
    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
    15. Preview
  7. Author Profile

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. Corrigendum
    7. News
    8. Author Profile
    9. News
    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Aiwen Lei (page 12136)

      Article first published online: 30 NOV 2011 | DOI: 10.1002/anie.201106054

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      “The biggest problem that scientists face is the pursuit of fame and fortune. If I won the lottery, I would stop applying for grants and concentrate on oxidative coupling research just for fun! …” This and more about Aiwen Lei can be found on page 12136.

  8. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. Corrigendum
    7. News
    8. Author Profile
    9. News
    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
    15. Preview
  9. Book Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. Corrigendum
    7. News
    8. Author Profile
    9. News
    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Statistical Mechanics: Theory and Molecular Simulation. By Mark E. Tuckerman. (pages 12138–12139)

      Saman Alavi

      Article first published online: 7 NOV 2011 | DOI: 10.1002/anie.201105752

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      Oxford University Press, 2010. 712 pp., hardcover, $ 90.00.—ISBN 978-0198525264

  10. Highlights

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. Corrigendum
    7. News
    8. Author Profile
    9. News
    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Reaction Mechanisms

      Metal-Mediated Deformylation Reactions: Synthetic and Biological Avenues (pages 12140–12142)

      Tuhin Patra, Srimanta Manna and Dr. Debabrata Maiti

      Article first published online: 24 OCT 2011 | DOI: 10.1002/anie.201103860

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      No two ways about it: The title reaction is immensely important in synthesis and biology. Whereas biological systems oxygenate aldehydes to generate formate and alkanes or alkenes, synthetic deformylation reactions primarily rely on rapid oxidative addition into the C(O)[BOND]H bond and subsequent rate-determining extrusion of CO.

    2. DNA Demethylation

      Oxidized Cytosine Metabolites Offer a Fresh Perspective for Active DNA Demethylation (pages 12143–12145)

      Dr. Kathrin I. Ladwein and Prof. Dr. Manfred Jung

      Article first published online: 23 NOV 2011 | DOI: 10.1002/anie.201106690

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      DNA methyltransferases catalyze the transfer of methyl groups to cytosines within DNA. Afterwards, 5-methylcytosine is oxidized to 5-hydroxymethylcytosine. Two further cytosine derivatives, 5-formylcytosine and 5-carboxycytosine, have been discovered recently. The existence of the seventh and eighth nucleobase provides new hints for deciphering the process of active DNA demethylation (see scheme).

    3. Organocatalysis

      Asymmetric α Alkylation of Aldehydes: Efficiency with Elegance (pages 12146–12147)

      Lotfi Tak-Tak, Prof. Dr. Hamid Dhimane and Dr. Peter I. Dalko

      Article first published online: 23 NOV 2011 | DOI: 10.1002/anie.201105001

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      Simple and practical: Direct intermolecular α alkylation reactions by SN1-type transformations have been developed and offer flexible and robust routes to major compound classes, for which the direct preparations were unavailable before.

  11. Minireview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. Corrigendum
    7. News
    8. Author Profile
    9. News
    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Synthetic Methods

      The Urea Renaissance (pages 12148–12155)

      Dr. Nicole Volz and Prof. Jonathan Clayden

      Article first published online: 15 NOV 2011 | DOI: 10.1002/anie.201104037

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      It's back: This Minireview summarizes the development of urea chemistry during the last few years by taking examples to illustrate each of the themes associated with this renaissance—ureas as lithiation directors, the design of urea-based catalysts and supramolecular structures, the increased reactivity that is characteristic of more hindered ureas, and the electrophilicity disguised within electron-rich aromatic ureas (see picture).

  12. Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. Corrigendum
    7. News
    8. Author Profile
    9. News
    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Chemical Genetics

      Optochemical Genetics (pages 12156–12182)

      Timm Fehrentz, Matthias Schönberger and Dirk Trauner

      Article first published online: 23 NOV 2011 | DOI: 10.1002/anie.201103236

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      Light of my life: The merger of natural transmembrane proteins with synthetic photoswitches creates hybrid receptors that can be integrated into complex systems and regulated with the precision that only light provides. This strategy allows for the optical control of single cells, neural systems, and can even be used to control animal behavior.

  13. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. Corrigendum
    7. News
    8. Author Profile
    9. News
    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Nanoparticle Catalysis

      Au–Pd Core–Shell Nanoparticles Catalyze Suzuki–Miyaura Reactions in Water through Pd Leaching (pages 12184–12188)

      Ping-Ping Fang, Prof. Anny Jutand, Prof. Zhong-Qun Tian and Prof. Christian Amatore

      Article first published online: 26 SEP 2011 | DOI: 10.1002/anie.201103465

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      Away from the surface: Novel nanoparticles (NPs) consisting of 16 nm Au cores surrounded by Pd shells of various thicknesses catalyze Suzuki–Miyaura cross-coupling reactions in water at room temperature. NPs having shells of two to five Pd monolayers thick exhibit the highest catalytic activity. Catalysis was attributed to the leaching of Pd species from the NPs through the synergistic action of the carbonate base and the arylboronic acid.

    2. Asymmetric Catalysis

      Enantioselective Diels–Alder Reactions with Anomalous endo/exo Selectivities Using Conformationally Flexible Chiral Supramolecular Catalysts (pages 12189–12192)

      Dr. Manabu Hatano, Tomokazu Mizuno, Dr. Atsuto Izumiseki, Ryota Usami, Dr. Takafumi Asai, Dr. Matsujiro Akakura and Prof. Dr. Kazuaki Ishihara

      Article first published online: 25 OCT 2011 | DOI: 10.1002/anie.201106497

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      Swapped selectivities: The use of tailor-made catalysts results in anomalous endo/exo selectivities and high enantioselectivities in the Diels–Alder reactions of cyclopentadiene with different acroleins (see scheme). These supramolecular catalysts are prepared in situ from chiral diols, arylboronic acid, and tris(pentafluorophenyl)borane, and can discriminate the re/si face of the dienophile as well as the endo/exo approach of the diene.

    3. Functional MOFs

      Metal–Organic Framework Regioisomers Based on Bifunctional Ligands (pages 12193–12196)

      Dr. Min Kim, Jake A. Boissonnault, Phuong V. Dau and Prof. Dr. Seth M. Cohen

      Article first published online: 24 OCT 2011 | DOI: 10.1002/anie.201106429

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      Regioisomeric MOFs: A series of bifunctional metal–organic framework (MOF) regioisomers has been produced from amino-halo benzene dicarboxylate (NH2X-BDC) ligands. ZrIV- and ZnII-based MOFs were synthesized and for the flexbile ZnII-based MOFs, gas sorption properties were dependent on the ligand substitution pattern.

    4. Synthetic Methods

      Heteropoly Compound Catalyzed Synthesis of Both Z- and E-α,β-Unsaturated Carbonyl Compounds (pages 12197–12200)

      Dr. Masahiro Egi, Megumi Umemura, Takuya Kawai and Prof. Dr. Shuji Akai

      Article first published online: 25 OCT 2011 | DOI: 10.1002/anie.201106381

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      AnEZswitch: The cationic species of the heteropoly compounds has a critical impact on the Z/E selectivity of the Meyer–Schuster rearrangement of propargyl alcohols (see scheme). The isolation of the thermodynamically unfavorable Z-α,β-unsaturated carbonyl compounds is notable. The high Z selectivities were obtained at a reaction temperature as high as 50 °C.

    5. Protein Mimetics

      Induced-Fit Binding of a Polyproline Helix by a β-Hairpin Peptide (pages 12201–12204)

      Dr. Dale J. Wilger, Jessica H. Park, Dr. Robert M. Hughes, Dr. Matthew E. Cuellar and Prof. Marcey L. Waters

      Article first published online: 28 OCT 2011 | DOI: 10.1002/anie.201106177

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      Form-fitting: The study of a minimal mimic of a protein domain that binds to type II polyproline helices through an aromatic cleft is reported. This binding motif mimics that of protein domains, including those important in disease states such as HIV infection and cancer. This study provides insight into the structure–function relationship in binding as well as quantitative data on the magnitude of prolyl–π interactions relevant to inhibitor design.

    6. Electron-Deficient Bonding

      Dinucleating Naphthyridine-Based Ligand for Assembly of Bridged Dicopper(I) Centers: Three-Center Two-Electron Bonding Involving an Acetonitrile Donor (pages 12205–12208)

      Timothy C. Davenport and Prof. T. Don Tilley

      Article first published online: 31 OCT 2011 | DOI: 10.1002/anie.201106081

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      Unusual bonding: A ligand system that promotes formation of a rare μ-η11 acetonitrile-bridged dicopper(I) complex (see picture) has been developed. The acetonitrile ligand is involved in a three-center two-electron bond supported by a cuprophilic interaction. The labile acetonitrile ligand can be substituted with xylyl isocyanide or CO.

    7. Photocatalysis

      Efficient Photocatalytic Hydrogen Production in a Single-Component System Using Ru,Rh,Ru Supramolecules Containing 4,7-Diphenyl-1,10-Phenanthroline (pages 12209–12213)

      Travis A. White, Samantha L. H. Higgins, Dr. Shamindri M. Arachchige and Prof. Karen J. Brewer

      Article first published online: 25 OCT 2011 | DOI: 10.1002/anie.201105170

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      Small changes go a long way: Modification of the terminal ligand to incorporate 4,7-diphenyl-1,10-phenanthroline has generated superior Ru,Rh,Ru photocatalysts (see scheme; ochre Ru, red Rh, blue N, yellow Cl or Br) displaying significantly enhanced photocatalytic H2 production from H2O with long-term functioning: H2O is reduced to H2 with over 1300 turnovers per Rh site and a maximum efficiency of 7.3 %.

    8. Fluorescence

      High Stokes Shift Anilido-Pyridine Boron Difluoride Dyes (pages 12214–12217)

      Juan F. Araneda, Warren E. Piers, Belinda Heyne, Masood Parvez and Robert McDonald

      Article first published online: 21 OCT 2011 | DOI: 10.1002/anie.201105228

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      To dye for: Three related families of fluorescent dyes, rigidified by boron difluoride and based on bidentate anilido-pyridyl donor ligands, are reported (see picture). The dyes show quantum yields up to 0.75 and improved Stokes shifts of >100 nm relative to the widely employed BODIPY family of dyes. Furthermore, the new dyes are exceptionally photostable and membrane-specific.

    9. Mesoporous Materials

      Highly Efficient Extraction of Serum Peptides by Ordered Mesoporous Carbon (pages 12218–12221)

      Hongqiang Qin, Peng Gao, Fangjun Wang, Liang Zhao, Jun Zhu, Prof. Dr. Aiqin Wang, Prof. Dr. Tao Zhang, Prof. Dr. Ren'an Wu and Prof. Dr. Hanfa Zou

      Article first published online: 26 OCT 2011 | DOI: 10.1002/anie.201103666

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      Size matters: A highly ordered mesoporous carbon material (OMC) was synthesized by a soft-template method, and was applied as an adsorbent for the highly efficient extraction of endogenous peptides from human serum (see scheme). A total of 3402 different peptides were identified from only 20 μL of human serum.

    10. Synthetic Methods

      Development of a Catalytic Platform for Nucleophilic Substitution: Cyclopropenone-Catalyzed Chlorodehydration of Alcohols (pages 12222–12226)

      Christine M. Vanos and Prof. Tristan H. Lambert

      Article first published online: 26 OCT 2011 | DOI: 10.1002/anie.201104638

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      Cyclopropenone makes the switch: 2,3-Bis-(p-methoxyphenyl)cyclopropenone is a highly efficient catalyst for the chlorodehydration of 20 diverse alcohol substrates (see scheme; X=Cl). With oxalyl chloride as catalytic activator, this nucleophilic substitution proceeded through cyclopropenium-activated intermediates and resulted in complete stereochemical inversion in substrates with chiral centers.

    11. Hydrogen Activation

      Heterolytic Cleavage of Dihydrogen by “Frustrated Lewis Pairs” Comprising Bis(2,4,6-tris(trifluoromethyl)phenyl)borane and Amines: Stepwise versus Concerted Mechanism (pages 12227–12231)

      Zhenpin Lu, Zhonghua Cheng, Dr. Zhenxia Chen, Prof. Linhong Weng, Prof. Zhen Hua Li and Prof. Huadong Wang

      Article first published online: 25 OCT 2011 | DOI: 10.1002/anie.201104999

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      Channeling the frustration: Frustrated Lewis pairs (FLPs) consisting of ArF2BH 1 with NEt3 or DABCO can activate H2 under mild conditions. Theoretical calculations suggest two distinct reaction pathways for these two FLPs. For the “more frustrated” ArF2BH/NEt3, H2 is activated in a stepwise manner; for the “less frustrated” ArF2BH/DABCO, H2 is activated in a concerted fashion (see scheme).

    12. Carbonyl Reactivity

      Reversing the Reactivity of Carbonyl Functions with Phosphonium Salts: Enantioselective Total Synthesis of (+)-Centrolobine (pages 12232–12235)

      Prof. Dr. Hiromichi Fujioka, Kenzo Yahata, Ozora Kubo, Yoshinari Sawama, Tomohito Hamada and Dr. Tomohiro Maegawa

      Article first published online: 3 NOV 2011 | DOI: 10.1002/anie.201106046

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      Step saver: Carbonyl groups with lower reactivities can be transformed in the presence of more reactive ones by treatment with PPh3 (or PEt3) and TMSOTf prior to the reaction (see scheme; TMS=trimethylsilyl, Tf=trifluoromethanesulfonyl). This methodology can be applied to reduction and alkylation reactions, and enabled the short asymmetric total synthesis of (+)-centrolobine with the highest overall yield reported to date.

    13. C[BOND]H Activation

      Synergistic Palladium-Catalyzed C(sp3)[BOND]H Activation/C(sp3)[BOND]O Bond Formation: A Direct, Step-Economical Route to Benzolactones (pages 12236–12239)

      Dr. Petr Novák, Dr. Arkaitz Correa, Dr. Joan Gallardo-Donaire and Dr. Ruben Martin

      Article first published online: 31 OCT 2011 | DOI: 10.1002/anie.201105894

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      Simplified access: Substituted benzolactones can be obtained in one step by a Pd-catalyzed ligand-accelerated C(sp3)[BOND]H bond-activation/C(sp3)[BOND]O bond-formation protocol. This step-economical approach enables the preparation of benzolactones with a wide variety of functional groups and different substitution patterns. The method is characterized by its simplicity and the avoidance of protecting groups.

    14. Homogeneous Catalysis

      Synthesis of Peptides and Pyrazines from β-Amino Alcohols through Extrusion of H2 Catalyzed by Ruthenium Pincer Complexes: Ligand-Controlled Selectivity (pages 12240–12244)

      Dr. Boopathy Gnanaprakasam, Dr. Ekambaram Balaraman, Yehoshoa Ben-David and Prof. David Milstein

      Article first published online: 26 OCT 2011 | DOI: 10.1002/anie.201105876

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      Your choice: The choice of the Ru-pincer-complex catalyst determines if peptides or pyrazines are formed from β-amino alcohols. Use of PNN complex 1 leads to linear poly(alanine) or to cyclic dipeptides, depending on the R group (see scheme). With the PNP complex 2, pyrazines are formed. These reactions are homogeneously catalyzed under neutral conditions and are environmentally benign.

    15. Gold Nanoplates

      Synthesis of Gold Square-like Plates from Ultrathin Gold Square Sheets: The Evolution of Structure Phase and Shape (pages 12245–12248)

      Dr. Xiao Huang, Dr. Hai Li, Dr. Shaozhou Li, Dr. Shixin Wu, Prof. Freddy Boey, Prof. Jan Ma and Prof. Hua Zhang

      Article first published online: 3 NOV 2011 | DOI: 10.1002/anie.201105850

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      It's hip to be square: Gold square-like plates exhibit alternating hexagonal close-packed (hcp, see picture, yellow) and face-centered cubic (fcc, red) structures in the center and defect-free fcc structures at one pair of the opposite thick edges. They can be synthesized from Au square sheets in a secondary growth process. For the first time, the hcp-to-fcc phase transformation associated with shape variation in Au nanostructures is demonstrated.

    16. Asymmetric Catalysis

      Asymmetric Synthesis of Chiral 1,3-Diaminopropanols: Bisoxazolidine-Catalyzed C[BOND]C Bond Formation with α-Keto Amides (pages 12249–12252)

      Hanhui Xu and Prof. Dr. Christian Wolf

      Article first published online: 31 OCT 2011 | DOI: 10.1002/anie.201105778

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      Three high-yielding steps lead to the formation of chiral 1,3-diaminopropanols from aliphatic and aromatic α-keto amides. In this approach, a nitroaldol reaction, which is catalyzed by Cu(SO2CF3)2 and the bisoxazolidine ligand L1, is followed by two mild reduction reactions (see scheme). Laborious protection and deprotection steps can be avoided by using this method.

    17. C[BOND]C coupling

      Exception to the ortho Effect in Palladium/Norbornene Catalysis (pages 12253–12256)

      Marie-Hélène Larraufie, Dr. Giovanni Maestri, Aurore Beaume, Dr. Étienne Derat, Dr. Cyril Ollivier, Prof. Louis Fensterbank, Prof. Christine Courillon, Dr. Emmanuel Lacôte, Prof. Marta Catellani and Prof. Max Malacria

      Article first published online: 21 OCT 2011 | DOI: 10.1002/anie.201104356

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      Out of the norm: The first deviation from the ortho effect in palladium/norbornene catalysis, as evidenced by the resulting products, is reported (see scheme). DFT calculations indicate that this deviation is likely to originate from a distortion, caused by specific chelation, in the reductive-elimination pathway from the PdIV intermediate initially formed. Addition of water restores the normal selectivity, but also it leads to dearomatization.

    18. Heterocycles

      Palladium-Catalyzed Reaction of Aryl Iodides with ortho-Bromoanilines and Norbornene/Norbornadiene: Unexpected Formation of Dibenzoazepine Derivatives (pages 12257–12261)

      Dr. Nicola Della Ca', Dr. Giovanni Maestri, Prof. Max Malacria, Dr. Etienne Derat and Prof. Marta Catellani

      Article first published online: 26 OCT 2011 | DOI: 10.1002/anie.201104363

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      Expecting the unexpected: The title reaction leads to satisfactory yields of dihydrodibenzoazepines 1 a from norbornene. The dibenzoazepines 2 can also be accessed from compounds of type 1 b when norbornadiene is used as a reactant. Theoretical studies show that the reaction represents a chelation-driven deviation from the usual selectivity observed in the presence of ortho-substituents on the aryl iodide.

    19. Asymmetric Catalysis

      Chiral Zinc-Catalyzed Asymmetric α-Alkylallylation and α-Chloroallylation of Aldehydes (pages 12262–12265)

      Prof. Dr. Shū Kobayashi, Toshimitsu Endo and Dr. Masaharu Ueno

      Article first published online: 25 OCT 2011 | DOI: 10.1002/anie.201106433

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      Two birds with one stone: In the presence of Zn(OH)2 and a chiral bipyridine ligand, racemic α-substituted allylboronates 2 reacted with aldehydes 1 (see scheme) exclusively in an α-addition fashion to afford various homoallylic alcohols 3 bearing two neighboring stereogenic centers in high yields with high diastereo- and enantioselectivities.

    20. Bioelectronics

      A Photo-Thermal-Electrical Converter Based On Carbon Nanotubes for Bioelectronic Applications (pages 12266–12270)

      Dr. Eijiro Miyako, Dr. Chie Hosokawa, Dr. Masami Kojima, Dr. Masako Yudasaka, Dr. Ryoji Funahashi, Dr. Isao Oishi, Dr. Yoshihisa Hagihara, Dr. Mototada Shichiri, Mizuki Takashima, Keiko Nishio and Dr. Yasukazu Yoshida

      Article first published online: 26 OCT 2011 | DOI: 10.1002/anie.201106136

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      Electrifying! A device based on carbon nanotubes wrapped with poly(3-hexylthiophene) (and dispersed in poly(dimethylsiloxane)) sheets can effectively convert laser light into thermal energy and subsequently to electricity. The converter is flexible and extremely compact (see picture), and can be manipulated by using a laser that functions in the wavelength range that can be transmitted through living tissue.

    21. Surface Functionalization

      Molecular Camouflage: Making Use of Protecting Groups To Control the Self-Assembly of Inorganic Janus Particles onto Metal–Chalcogenide Nanotubes by Pearson Hardness (pages 12271–12275)

      Jugal Kishore Sahoo, Dr. Muhammad Nawaz Tahir, Faegheh Hoshyargar, Bahar Nakhjavan, Robert Branscheid, Ute Kolb and Prof. Dr. Wolfgang Tremel

      Article first published online: 26 OCT 2011 | DOI: 10.1002/anie.201105337

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      Hard and soft: Binding of inorganic Pt@Fe3O4 Janus particles to WS2 nanotubes through their Pt or Fe3O4 domains is governed by the difference in Pearson hardness: the soft Pt block has a higher sulfur affinity than the harder magnetite face; thus the binding proceeds preferentially through the Pt face. This binding preference can be reversed by masking the Pt face with an organic protecting group.

    22. Water Splitting

      Highly Efficient Oxidation of Water by a Molecular Catalyst Immobilized on Carbon Nanotubes (pages 12276–12279)

      Dr. Fei Li, Biaobiao Zhang, Xiaona Li, Yi Jiang, Lin Chen, Yanqing Li and Prof. Licheng Sun

      Article first published online: 26 OCT 2011 | DOI: 10.1002/anie.201105044

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      A successful team: A molecular device based on multiwalled carbon nanotubes functionalized by a mononuclear ruthenium catalyst has been shown to split water electrochemically (see picture; ITO=indium tin oxide). The readily prepared electrode showed excellent electrocatalytic activity for the oxidation of water, a high current density, and a low overpotential, and constitutes one step forward in the design of artificial photosynthetic systems.

    23. Chemical Topology

      Active-Metal Template Synthesis of a Molecular Trefoil Knot (pages 12280–12284)

      Dr. Perdita E. Barran, Harriet L. Cole, Dr. Stephen M. Goldup, Prof. David A. Leigh, Dr. Paul R. McGonigal, Dr. Mark D. Symes, Jhenyi Wu and Michael Zengerle

      Article first published online: 14 SEP 2011 | DOI: 10.1002/anie.201105012

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      Tying the knot: The marriage of catalysis and coordination chemistry enables two CuI ions (red; see picture) to work in partnership for the synthesis of a molecular trefoil knot. One ion entangles an acyclic building block to create a loop in the ligand, and the other gathers the ligand's reactive end-groups, threads the loop, and catalyzes the covalent capture of the knotted architecture by an alkyne–azide “click” reaction.

    24. Morphological Transitions

      Programmed Morphological Transitions of Multisegment Assemblies by Molecular Chaperone Analogues (pages 12285–12289)

      Job Boekhoven, Dr. Aurelie M. Brizard, Dr. Patrick van Rijn, Dr. Marc C. A. Stuart, Dr. Rienk Eelkema and Prof. Dr. Jan H. van Esch

      Article first published online: 14 JUL 2011 | DOI: 10.1002/anie.201102364

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      A multisegment amphiphile, made of a gelator and a surfactant, self-assembles into architectures with properties inherited from both segments. By addition of a surfactant, the surfactant segment of the amphiphile is selectively switched off, leading to the formation of fibrils. The addition of urea or hexafluoroisopropyl alcohol (HFIP) switches off the gelator segment, giving micelles.

    25. Magnetoresponsive Biomaterials

      Conversion of Magnetic Impulses into Cellular Responses by Self-Assembled Nanoparticle–Vesicle Hydrogels (pages 12290–12293)

      Felicity de Cogan, Andrew Booth, Dr. Julie E. Gough and Dr. Simon J. Webb

      Article first published online: 25 OCT 2011 | DOI: 10.1002/anie.201103469

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      Crosslinking vesicles with magnetic nanoparticles produced MNPVs, self-assembled “nanopills” that can be “unlocked” by an alternating magnetic field (AMF), releasing chemical messengers stored within the vesicles. When MNPVs are co-immobilized with cells in a hydrogel matrix, exposure to an AMF magnetic signal releases the chemical messengers, which then induce a cellular response.

    26. Nanocatalysis

      Crystal-Plane-Controlled Surface Restructuring and Catalytic Performance of Oxide Nanocrystals (pages 12294–12298)

      Huizhi Bao, Dr. Wenhua Zhang, Qing Hua, Dr. Zhiquan Jiang, Prof. Dr. Jinlong Yang and Prof. Dr. Weixin Huang

      Article first published online: 26 OCT 2011 | DOI: 10.1002/anie.201103698

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      Crystal clear: Uniform Cu2O nanooctahedra (o-Cu2O) and nanocubes (c-Cu2O) undergo surface restructuring during CO oxidation for the in-situ formation of catalytically active CuO thin films to give CuO/o-Cu2O and CuO/c-Cu2O, respectively (see picture). The structure and catalytic performance of CuO thin films are controlled by the crystal plane exposed on the underlying Cu2O nanocrystals.

    27. Imaging Agents

      Ultrasmall Rigid Particles as Multimodal Probes for Medical Applications (pages 12299–12303)

      Dr. François Lux, Dr. Anna Mignot, Dr. Pierre Mowat, Dr. Cédric Louis, Dr. Sandrine Dufort, Dr. Claire Bernhard, Prof. Franck Denat, Dr. Frédéric Boschetti, Dr. Claire Brunet, Prof. Rodolphe Antoine, Prof. Philippe Dugourd, Dr. Sophie Laurent, Prof. Luce Vander Elst, Prof. Robert Muller, Dr. Lucie Sancey, Dr. Véronique Josserand, Prof. Jean-Luc Coll, Dr. Vasile Stupar, Dr. Emmanuel Barbier, Dr. Chantal Rémy, Dr. Alexis Broisat, Prof. Catherine Ghezzi, Dr. Géraldine Le Duc, Prof. Stéphane Roux, Prof. Pascal Perriat and Prof. Olivier Tillement

      Article first published online: 4 NOV 2011 | DOI: 10.1002/anie.201104104

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      Ultrasmall but multifunctional: Rigid imaging particles that are smaller than 5 nm in size can be obtained in a top-down process starting from a core–shell structure (core=gadolinium oxide; shell=polysiloxane). They represent the first multifunctional silica-based particles that are sufficiently small to escape hepatic clearance and enable animal imaging by four complementary techniques.

    28. Enzyme Mechanisms

      Mechanistic Studies of an IspH-Catalyzed Reaction: Implications for Substrate Binding and Protonation in the Biosynthesis of Isoprenoids (pages 12304–12307)

      Wei-chen Chang, Dr. Youli Xiao, Prof. Dr. Hung-wen Liu and Prof. Dr. Pinghua Liu

      Article first published online: 24 OCT 2011 | DOI: 10.1002/anie.201104124

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      Chosen handle: Mechanistic studies of the IspH-catalyzed reductive dehydroxylation of 4-hydroxy-3-methyl-2-(E)-1-diphosphate (HMBPP) to isopentenyl diphosphate and dimethylallyl diphosphate suggest that both the 4-OH group and the double bond of HMBPP may contribute to the formation of substrate–IspH complex. Labeling studies now show that the 4-hydroxy group of the substrate plays the dominant role in positioning the substrate in the enzyme active site.

    29. Cancer Imaging

      X-Ray Computed Tomography Imaging of Breast Cancer by using Targeted Peptide-Labeled Bismuth Sulfide Nanoparticles (pages 12308–12311)

      Dr. Joseph M. Kinsella, Rebecca E. Jimenez, Priya P. Karmali, Anthony M. Rush, V. Ramana Kotamraju, Prof. Nathan C. Gianneschi, Prof. Erkki Ruoslahti, Dr. Dwayne Stupack and Prof. Michael J. Sailor

      Article first published online: 26 OCT 2011 | DOI: 10.1002/anie.201104507

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      Enhanced visualization of breast cancer in X-ray computed tomography was achieved by using Bi2S3 nanoparticles of 10 nm diameter modified to display a tumor targeting peptide (LyP-1, CGNKRTRGC). Accumulation within the tumor was increased by 260 % over non-labeled nanoparticles.

    30. Delivery Platforms

      Oligonucleotide Delivery by Cell-Penetrating “Striped” Nanoparticles (pages 12312–12315)

      Dr. Christopher M. Jewell, Dr. Jin-Mi Jung, Prabhani U. Atukorale, Randy P. Carney, Prof. Francesco Stellacci and Prof. Darrell J. Irvine

      Article first published online: 26 OCT 2011 | DOI: 10.1002/anie.201104514

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      Gold nanoparticles coated with homogeneous (MUS) or “striped” (MUS-OT) ligand shells can be conjugated with double or single stranded DNA, and particles with either ligand configuration effectively carry DNA into melanoma tumor cells. When endocytosis is inhibited, however, MUS-OT particles continue to mediate DNA delivery, while the delivery ability of MUS particles is abolished.

    31. Nanotube Structures

      Synthesis of Copious Amounts of SnS2 and SnS2/SnS Nanotubes with Ordered Superstructures (pages 12316–12320)

      Gal Radovsky, Dr. Ronit Popovitz-Biro, Matthias Staiger, Dr. Konstantin Gartsman, Prof. Christian Thomsen, Tommy Lorenz, Prof. Gotthard Seifert and Prof. Dr. Reshef Tenne

      Article first published online: 28 OCT 2011 | DOI: 10.1002/anie.201104520

      Thumbnail image of graphical abstract

      Roll 'em up, move 'em out: The growth of SnS2 and SnS2/SnS nanotubes and nanoscrolls with ordered superstructures is promoted by the relaxation of stress between adjacent SnS2 and SnS layers. Partial decomposition of the SnS2 precursor to more sulfur-deficient SnS was manifested in the exfoliation of layers and scrolling. The presence of the two main structures (see picture) was confirmed by HRTEM and Raman spectroscopy.

    32. Dye-Sensitized Solar Cells

      Hierarchically Assembled ZnO Nanocrystallites for High-Efficiency Dye-Sensitized Solar Cells (pages 12321–12325)

      Nafiseh Memarian, Isabella Concina, Antonio Braga, Seyed Mohammad Rozati, Alberto Vomiero and Giorgio Sberveglieri

      Article first published online: 26 SEP 2011 | DOI: 10.1002/anie.201104605

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      Spray pyrolysis is effective in the formation of a nanoengineered photoanode. An unprecedented photoconversion efficiency of 7.5 % for ZnO-based dye-sensitized cells was achieved on a photoelectrode consisting of polydispersed ZnO aggregates of nanocrystallites over a compact ZnO buffer layer at a firing temperature of 450 °C. FTO= fluorine-doped tin oxide.

    33. Porous Capsules

      Softening of Pore and Interior Properties of a Metal-Oxide-Based Capsule: Substituting 60 Oxide by 60 Sulfide Ligands (pages 12326–12329)

      Christian Schäffer, Dr. Ana Maria Todea, Dr. Hartmut Bögge, Prof. Dr. Emmanuel Cadot, Prof. Dr. Pierre Gouzerh, Sivil Kopilevich, Prof. Dr. Ira A. Weinstock and Prof. Dr. Achim Müller

      Article first published online: 27 OCT 2011 | DOI: 10.1002/anie.201104642

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      A hard capsule gets soft: The exchange of 60 oxide by 60 sulfide ligands (see picture) in a well-known porous metal-oxide capsule skeleton conataining 132 metal atoms changes the interior properties as well as pore sizes, reactivities, flexibilities and affinities to guest molecules.

    34. Doped Nanocrystals

      Sodium Doping Controlled Synthesis of Monodisperse Lanthanide Oxysulfide Ultrathin Nanoplates Guided by Density Functional Calculations (pages 12330–12334)

      Yi Ding, Jun Gu, Jun Ke, Prof. Ya-Wen Zhang and Prof. Chun-Hua Yan

      Article first published online: 21 OCT 2011 | DOI: 10.1002/anie.201105025

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      Dopant-induced phenomena: Doping with sodium ions can stimulate the formation of monodisperse ultrathin La2O2S nanoplates with tunable self-assembled superstructures (see picture) and robust fluorescence in surfactant solutions by creating oxygen vacancies in the host lattice during sulfurization reactions.

    35. Asymmetric Catalysis

      Asymmetric Conjugate Addition of Glycine Derivatives under Copper Catalysis (pages 12335–12338)

      Dr. Mark Strohmeier, Kevin Leach and Dr. Matthew A. Zajac

      Article first published online: 26 OCT 2011 | DOI: 10.1002/anie.201105258

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      Coppertunity knocks: An inexpensive, practical, and environmentally benign procedure for the enantioselective addition of glycine derivatives to α,β-unsaturated ketones has been developed (see scheme). By modifying the workup, the conjugate addition product or a cyclic imine can be accessed. The solution structure of the catalyst–substrate complex is shown to be key to the overall reaction selectivity.

    36. Heteroborane Ligands

      Diphosphaborane and Metalladiphosphaborane: Ligands for Transition-Metal Chemistry (pages 12339–12341)

      Dr. Ross McLellan, Dr. David Ellis, Dr. Georgina M. Rosair and Prof. Alan J. Welch

      Article first published online: 24 OCT 2011 | DOI: 10.1002/anie.201105820

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      New ligands: The first examples of a neutral heteroborane and a neutral metallaheteroborane acting as simple σ-bound ligands to transition metals are described. In [HCo(1,2-closo-P2B10H10)2(PEt3)2] (see structure, left) the P2B10H10 ligand coordinates to Co through one P atom, and in μ-[1,2-{HRu(p-cymene)}2-7′,8′-nido-P2B9H9]-3-(p-cymene)-3,1,2-closo-RuP2B9H9 (right) both closo-RuP2B9 and nido-P2B9 cages act as bridging κP:κP′ ligands.

    37. Catalytic Oxidation

      Catalytic Degenerate and Nondegenerate Oxygen Atom Transfers Employing N2O and CO2 and a MII/MIV Cycle Mediated by Group 6 MIV Terminal Oxo Complexes (pages 12342–12346)

      Brendan L. Yonke, Jonathan P. Reeds, Peter Y. Zavalij and Prof. Lawrence R. Sita

      Article first published online: 28 OCT 2011 | DOI: 10.1002/anie.201106074

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      Green oxidation: A new class of Group 6 metal complexes catalyzes the direct oxidation of isocyanides through nondegenerate oxygen atom transfer (OAT) utilizing N2O as a chemical oxidant. In addition they serve as photocatalysts for the reversible degenerate OAT between CO and CO2 (see scheme).

    38. Photosynthesis

      Electron Transport between Photosystem II and Photosystem I Encapsulated in Sol–Gel Glasses (pages 12347–12350)

      Dr. Frieda Kopnov, Dr. Ilit Cohen-Ofri and Dr. Dror Noy

      Article first published online: 21 OCT 2011 | DOI: 10.1002/anie.201106293

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      Happily coupled: Photosystem II and photosystem I can be coupled in a sol–gel system so that electron flow can be directly mediated from photooxidized water at the donor side of photosystem II to the highly reducing acceptor side of photosystem I. The electron transfer pathway is set up by addition of the amphipathic quinone analogue 2,6dichlorophenolindophenol (DCPIP) to the sol–gel mixture to provide a pool of redox carriers (see picture).

    39. Gas-Phase Reactions

      Catalytic Redox Reactions in the CO/N2O System Mediated by the Bimetallic Oxide-Cluster Couple AlVO3+/AlVO4+ (pages 12351–12354)

      Dr. Zhe-Chen Wang, Dipl.-Chem. Nicolas Dietl, Dipl.-Chem. Robert Kretschmer, Dr. Thomas Weiske, Dr. Maria Schlangen and Prof. Dr. Helmut Schwarz

      Article first published online: 27 SEP 2011 | DOI: 10.1002/anie.201105691

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      Exhaustive studies: The exact reaction pathway of catalytic conversion of automobile exhaust gases, such as N2O and CO, into N2 and CO2 is still not completely understood. Studying this reaction at room temperature using the bimetallic oxide cluster couple AlVO3+/AlVO4+ in the gas phase shows that the active M-Ot. site is located at the Al-bound and not the V-bound oxygen atom (see scheme, Al pink).

    40. Shuttling Oxygen

      Aerobic Alcohol Oxidations Mediated by Nitric Acid (pages 12355–12360)

      Christof Aellig, Christophe Girard and Prof. Dr. Ive Hermans

      Article first published online: 21 OCT 2011 | DOI: 10.1002/anie.201105620

      Thumbnail image of graphical abstract

      A touch of acid: Catalytic amounts of HNO3 can trigger the aerobic oxidation of alcohols in the presence of the solid acid amberlyst-15. The desired oxidation cycle, mediated by (H)NOx species, is in kinetic competition with the detrimental formation of N2O by HNO dimerization (see scheme). In situ water removal in a gas recirculation reactor increases the reaction rate and the end-conversion by minimizing N2O formation and increasing the (H)NOx turnover.

    41. Molecular Disulfate

      ReO2Cl(S2O7), a Molecular Disulfate (pages 12361–12363)

      Dipl.-Chem. Ulf Betke, Wilke Dononelli, Prof. Dr. Thorsten Klüner and Prof. Dr. Mathias S. Wickleder

      Article first published online: 26 OCT 2011 | DOI: 10.1002/anie.201105457

      Thumbnail image of graphical abstract

      A molecular metal disulfate, Re2O4Cl2(S2O7)2 forms in the reaction of ReCl5 and oleum (65 % SO3) under harsh conditions. The first of its kind, this unique ReVII compound contains two ReO2Cl fragments linked by two disulfate groups, leading to Ci-symmetric molecules (see picture; Re red, O blue, S yellow, Cl green).

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      Preview: Angew. Chem. Int. Ed. 52/2011 (page 12365)

      Article first published online: 14 DEC 2011 | DOI: 10.1002/anie.201190108

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