Angewandte Chemie International Edition

Cover image for Vol. 50 Issue 17

April 18, 2011

Volume 50, Issue 17

Pages 3817–4021

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Obituary
    9. Highlights
    10. Correspondence
    11. Review
    12. Communications
    13. Preview
    1. Cover Picture: Synergy of Homogeneous and Heterogeneous Chemistry Probed by In Situ Spatially Resolved Measurements of Temperature and Composition (Angew. Chem. Int. Ed. 17/2011) (page 3817)

      Dr. Alessandro Donazzi, Dario Livio, Dr. Matteo Maestri, Prof. Alessandra Beretta, Prof. Gianpiero Groppi, Prof. Enrico Tronconi and Prof. Pio Forzatti

      Article first published online: 23 MAR 2011 | DOI: 10.1002/anie.201101593

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      The combination … … of a novel in situ sampling technique and a detailed model analysis was used to elucidate the interplay between the heterogeneous and homogeneous pyrolytic routes to H2 and CO in the catalytic partial oxidation of C3H8 over rhodium, as described by A. Beretta et al. in their Communication on page 3943 ff. The grasshopper in the picture represents the homogeneous chemistry, which skips the Rh surface and produces hydrocarbons in the gas phase. The gecko stands for the heterogeneous chemistry, which sticks on the Rh surface and leads to synthesis gas. The authors thank F. Tosi for the picture.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Obituary
    9. Highlights
    10. Correspondence
    11. Review
    12. Communications
    13. Preview
    1. Inside Cover: Semiconductor Anisotropic Nanocomposites Obtained by Directly Coupling Conjugated Polymers with Quantum Rods (Angew. Chem. Int. Ed. 17/2011) (page 3818)

      Lei Zhao, Dr. Xinchang Pang, Ramkrishna Adhikary, Prof. Jacob W. Petrich and Prof. Zhiqun Lin

      Article first published online: 13 APR 2011 | DOI: 10.1002/anie.201101731

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      Semiconductor anisotropic nanocomposites are promising materials for the use in organic–inorganic nanohybrid solar cells. In their Communication on page 3958 ff. Z. Lin and co-workers report such nanocomposites synthesized by a catalyst-free click reaction. In these architectures, CdSe nanorods and poly(3-hexylthiophene) are in intimate contact.

  3. Back Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Obituary
    9. Highlights
    10. Correspondence
    11. Review
    12. Communications
    13. Preview
    1. Back Cover: Double Switching of a Magnetic Coordination Framework through Intraskeletal Molecular Rearrangement (Angew. Chem. Int. Ed. 17/2011) (page 3818)

      Dr. Dawid Pinkowicz, Dr. Robert Podgajny, Dr. Bartłomiej Gaweł, Dr. Wojciech Nitek, Prof. Dr. Wiesław Łasocha, Marcin Oszajca, Dr. Mariusz Czapla, Magdalena Makarewicz, Dr. Maria Bałanda and Prof. Dr. Barbara Sieklucka

      Article first published online: 25 MAR 2011 | DOI: 10.1002/anie.201101733

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      The reversible removal of guest molecules in Mn2Nb magnetic coordination framework materials, as described by D. Pinkowicz, B. Sieklucka et al. in their Communication on page 3973 ff., causes a spectacular two-step molecular rearrangement of their skeleton involving the topotactic formation of an additional molecular bridge and the translocation of the incorporated organic ligand. These structural changes impact the magnetic ordering temperature and allow for its switching between 43, 68, and 100 K.

  4. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Obituary
    9. Highlights
    10. Correspondence
    11. Review
    12. Communications
    13. Preview
    1. Graphical Abstract: Angew. Chem. Int. Ed. 17/2011 (pages 3821–3832)

      Article first published online: 13 APR 2011 | DOI: 10.1002/anie.201190031

  5. News

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Obituary
    9. Highlights
    10. Correspondence
    11. Review
    12. Communications
    13. Preview
    1. Luis M. Liz-Marzán (page 3838)

      Article first published online: 13 APR 2011 | DOI: 10.1002/anie.201100259

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      “My greatest achievement has been bringing up two wonderful children. The biggest problem that scientists face is public awareness about the need for basic research …” This and more about Luis M. Liz-Marzán can be found on page 3838.

  7. Obituary

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Obituary
    9. Highlights
    10. Correspondence
    11. Review
    12. Communications
    13. Preview
    1. Kurt Dehnicke (1931–2011) (pages 3839–3840)

      Evamarie Hey-Hawkins

      Article first published online: 25 MAR 2011 | DOI: 10.1002/anie.201100900

  8. Highlights

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Obituary
    9. Highlights
    10. Correspondence
    11. Review
    12. Communications
    13. Preview
    1. CO2 Fixation

      Transition-Metal-Catalyzed Carboxylation of C[BOND]H Bonds (pages 3842–3844)

      Prof. Dr. Lutz Ackermann

      Article first published online: 22 MAR 2011 | DOI: 10.1002/anie.201007883

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      CO2 in a fix: Gold and copper complexes of N-heterocyclic carbenes recently enabled efficient direct carboxylation of (hetero)arenes having moderately acidic C[BOND]H bonds under remarkably mild reaction conditions (IPr=1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene).

    2. Metal-Catalyzed Hydrosilylation

      1,4-Hydrosilylation of Pyridine by Ruthenium Catalyst: A New Reaction and Mechanism (pages 3845–3846)

      Prof. Kohtaro Osakada

      Article first published online: 24 FEB 2011 | DOI: 10.1002/anie.201008199

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      Making introductions: A half-sandwich Ru complex catalyzes the hydrosilylation of pyridine derivatives to produce N-silyl-3-hydropyridine through a 1,4-addition of the Si–H group (see scheme). The reversibility of the hydrosilylation was suggested based on the experimental results.

    3. Organocatalysis

      Atroposelective Organocatalysis (pages 3847–3849)

      Prof. Pier Giorgio Cozzi, Dr. Enrico Emer and Dr. Andrea Gualandi

      Article first published online: 29 MAR 2011 | DOI: 10.1002/anie.201008031

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      Spin off: The synthesis of optically active biaryl compounds using enantioselective organocatalysis is highlighted. Foldamers coupled with organocatalysis, specifically hydrogen-bonding interactions (see scheme; Boc=tert-butoxycarbonyl), can be used to access compounds with a stereogenic axis. New selective syntheses of atropoisomers can be inspired by these findings, thus enhancing the use of atropoisomeric compounds in synthesis and catalysis.

  9. Correspondence

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Obituary
    9. Highlights
    10. Correspondence
    11. Review
    12. Communications
    13. Preview
    1. Oxo Complexes

      Comment on “A Low-Spin Ruthenium(IV)–Oxo Complex: Does the Spin State Have an Impact on the Reactivity” (pages 3850–3851)

      Dr. Detlef Schröder and Prof. Dr. Sason Shaik

      Article first published online: 25 MAR 2011 | DOI: 10.1002/anie.201007636

      Slippery spin states: When the metal center in a transition-metal complex can adopt multiple spin states, the reactivity of the complex may be influenced. In such cases, care must be taken that experimental and computational evidence are interpreted correctly.

    2. Reply (pages 3852–3853)

      Prof. Dr. Takahiko Kojima and Prof. Dr. Shunichi Fukuzumi

      Article first published online: 13 APR 2011 | DOI: 10.1002/anie.201100719

      Trust in experiments: As DFT calculations suggest that the hydrogen bonding of water molecules can stabilize a seven-coordinate ruthenium–oxo complex to exhibit a singlet spin state, experiments have shown that the novel seven-coordinate pentaganol-bipyramidal ruthenium–oxo complex has a singlet ground state. Nevertheless, it displays the same reactivity as an analogous triplet-state complex.

  10. Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Obituary
    9. Highlights
    10. Correspondence
    11. Review
    12. Communications
    13. Preview
    1. Renewable Raw Materials

      Oils and Fats as Renewable Raw Materials in Chemistry (pages 3854–3871)

      Dr. Ursula Biermann, Prof. Dr. Uwe Bornscheuer, Prof. Dr. Michael A. R. Meier, Prof. Dr. Jürgen O. Metzger and Prof. Dr. Hans J. Schäfer

      Article first published online: 29 MAR 2011 | DOI: 10.1002/anie.201002767

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      More than just a greasy spoon: Oils and fats are the most important renewable feedstock of the chemical industry. Recent and exciting advances in chemistry and biotechnology were made within the last 10 years concerning their utilization as a chemical feedstock. This progress in organic synthesis, catalysis, and biotechnology using plant oils and their derivatives is highlighted.

  11. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Obituary
    9. Highlights
    10. Correspondence
    11. Review
    12. Communications
    13. Preview
    1. Molecular Rotors

      Assembly and Manipulation of Rotatable Cerium Porphyrinato Sandwich Complexes on a Surface (pages 3872–3877)

      Dr. David Écija, Dr. Willi Auwärter, Saranyan Vijayaraghavan, Knud Seufert, Felix Bischoff, Dr. Kentaro Tashiro and Prof. Johannes V. Barth

      Article first published online: 11 APR 2011 | DOI: 10.1002/anie.201007370

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      Stacked up: Use of scanning tunneling microscopy allows manipulation of the upper porphyrin of tris(porphyrinato) cerium triple-decker complexes, which are obtained by a new synthetic route on a smooth Ag(111) surface (see picture).

    2. In Vivo Protein Labeling

      You have full text access to this OnlineOpen article
      Genetically Encoded Copper-Free Click Chemistry (pages 3878–3881)

      Tilman Plass, Sigrid Milles, Christine Koehler, Priv.-Doz. Dr. Carsten Schultz and Dr. Edward A. Lemke

      Article first published online: 23 MAR 2011 | DOI: 10.1002/anie.201008178

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      A bright click of life: Strained alkynes are genetically encoded into E. coli by use of an engineered pyrrolysine amber suppressor tRNA/synthetase pair from Methanosarcina mazei. As a result cyclooctynyl lysine derivatives were incorporated site-specifically in proteins allowing efficient labeling with fluorogenic azide-bearing dyes by means of a click reaction under physiological conditions in vitro and in vivo (see scheme).

    3. Biosynthesis

      Molecular Basis of Elansolid Biosynthesis: Evidence for an Unprecedented Quinone Methide Initiated Intramolecular Diels–Alder Cycloaddition/Macrolactonization (pages 3882–3887)

      Dr. Richard Dehn, Dr. Yohei Katsuyama, Arne Weber, Dr. Klaus Gerth, Dr. Rolf Jansen, Heinrich Steinmetz, Prof. Dr. Gerhard Höfle, Prof. Dr. Rolf Müller and Prof. Dr. Andreas Kirschning

      Article first published online: 29 MAR 2011 | DOI: 10.1002/anie.201006880

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      Total control: The key steps in the biosynthesis of elansolide A1, a new and structurally unique polyketide metabolite from the gliding bacterium Chitinophaga sancti, have been elucidated from feeding experiments, by analysis of the biosynthetic gene cluster, and through the synthesis of model substrates. These steps include an unprecedented dehydration reaction, an intramolecular Diels–Alder cycloaddition (IMDA), and an unusual macrolactonization.

    4. Heterogeneous Catalysis

      Ligand Capping of Colloidally Synthesized Nanoparticles—A Way to Tune Metal–Support Interactions in Heterogeneous Gas-Phase Catalysis (pages 3888–3891)

      Dr. Patrick Sonström, Darius Arndt, Dr. Xiaodong Wang, Dr. Volkmar Zielasek and Prof. Dr. Marcus Bäumer

      Article first published online: 29 MAR 2011 | DOI: 10.1002/anie.201004573

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      Better be capped: Ligand-capped, colloidally prepared Pt nanoparticles deposited on nanostructured iron oxide catalyze CO oxidation at unusually low temperatures when compared to the action of identical ligand-free Pt nanoparticles. The ligands efficiently modify the interaction between the metal and the iron oxide support and cause a beneficial strong metal–support interaction. As a result, the limitations resulting from CO poisoning at low temperatures can be overcome.

    5. Natural Product Synthesis

      A Total Synthesis of (±)-Codeine by 1,3-Dipolar Cycloaddition (pages 3892–3894)

      Thomas Erhard, Dr. Gunnar Ehrlich and Prof. Dr. Peter Metz

      Article first published online: 23 MAR 2011 | DOI: 10.1002/anie.201007448

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      Nitrone cycloaddition on a dearomatized bicyclic phenol enabled the facile construction of the correctly configured phenanthrene skeleton of codeine. Further steps yielded allopseudocodeine in a completely diastereoselective manner and finally (±)-codeine by allylic transposition through the hydrolysis of chlorocodides.

    6. Orthogonal Cross-Couplings

      Differentiating C[BOND]Br and C[BOND]Cl Bond Activation by Using Solvent Polarity: Applications to Orthogonal Alkyl–Alkyl Negishi Reactions (pages 3896–3899)

      Dr. Niloufar Hadei, George T. Achonduh, Dr. Cory Valente, Dr. Christopher J. O'Brien and Prof. Michael G. Organ

      Article first published online: 25 MAR 2011 | DOI: 10.1002/anie.201100705

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      A pot to share: A Calkyl[BOND]Cl bond can be rendered “dormant” or “active” in the Negishi alkyl–alkyl cross-coupling by a simple solvent polarity “switch” (see scheme). Adjustment from a 1:2 to a 2:1 solvent ratio of dimethylimidazolidinone:tetrahydrofuran enables orthogonal alkyl–alkyl Negishi cross-coupling strategies to be carried out on bifunctional bromochloroalkanes in one pot at room temperature.

    7. Catalytic Hydrogenation

      Z-Selective Semihydrogenation of Alkynes Catalyzed by a Cationic Vanadium Bisimido Complex (pages 3900–3903)

      Henry S. La Pierre, Prof. Dr. John Arnold and Prof. Dr. F. Dean Toste

      Article first published online: 21 MAR 2011 | DOI: 10.1002/anie.201007876

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      Early metal gets the H: Under 1 atm of H2, the vanadium complex 1 (PFTB=perfluoro-tert-butoxide) catalytically semihydrogenates alkynes to Z alkenes. Synthetic and DFT studies, in combination with H2/D2 and NMR experiments, indicate that H2 is activated by 1,2-addition to 1. Upon insertion of an alkyne into the V[BOND]H bond of A, the product alkene and 1 are generated by the 1,2-α-NH-elimination of the alkenyl ligand.

    8. Cross-Coupling Reactions

      Copper-Catalyzed Cross-Coupling Reaction of Organoboron Compounds with Primary Alkyl Halides and Pseudohalides (pages 3904–3907)

      Chu-Ting Yang, Zhen-Qi Zhang, Yu-Chen Liu and Prof. Dr. Lei Liu

      Article first published online: 31 MAR 2011 | DOI: 10.1002/anie.201008007

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      Non-activated alkyl electrophiles, including alkyl iodides, bromides, tosylates, mesylates, and even chlorides, underwent copper-catalyzed cross-coupling with aryl boron compounds and alkyl 9-BBN reagents (see scheme; 9-BBN=9-borabicyclo[3.3.1]nonane). The reactions proceed with practically useful reactivities and thus complement palladium- and nickel-catalyzed Suzuki–Miyaura coupling reactions of alkyl halides.

    9. Cluster Compounds

      A Family of Heterometallic Cubane-Type Clusters with an exo-Fe(CO)3 Fragment Anchored to the Cubane (pages 3908–3911)

      K. Geetharani, Shubhankar Kumar Bose, Satyanarayan Sahoo and Dr. Sundargopal Ghosh

      Article first published online: 21 MAR 2011 | DOI: 10.1002/anie.201008101

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      Metal-rich metallaboranes: An exo-Fe(CO)3 moiety linked to a cubane core is the most prominent feature of complexes [(Cp*M)23-E)2B2H(μ-H){Fe(CO)2}2Fe(CO)3] (M=Mo, E=S, Se; M=Ru, E=CO; Cp*=η5-C5Me5), which are the first heterobimetallic cubane-type clusters with a boride unit (see structure).

    10. Domino Reactions

      Cyclization–Carbonylation–Cyclization Coupling Reactions of Propargyl Acetates and Amides with Palladium(II)–Bisoxazoline Catalysts (pages 3912–3915)

      Sumie Yasuhara, Makiko Sasa, Dr. Taichi Kusakabe, Dr. Hiroyuki Takayama, Prof. Dr. Masayuki Kimura, Prof. Dr. Tomoyuki Mochida and Prof. Dr. Keisuke Kato

      Article first published online: 22 MAR 2011 | DOI: 10.1002/anie.201008139

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      Clever boxing: A cyclization–carbonylation–cyclization–coupling reaction of propargyl acetates 1 or amides 2 in the presence of a palladium(II)–bisoxazoline (box) catalyst afforded symmetrical ketones of types 3 and 4, respectively, containing two heterocyclic groups in moderate to excellent yields (see scheme; tfa=trifluoroacetate). Compounds 3 were converted into ketones containing two 3(2H)-furanone rings.

    11. Alkaloid Synthesis

      Total Synthesis of (±)-Alopecuridine and Its Biomimetic Transformation into (±)-Sieboldine A (pages 3916–3919)

      Xiao-Ming Zhang, Prof. Dr. Yong-Qiang Tu, Prof. Dr. Fu-Min Zhang, Hui Shao and Xing Meng

      Article first published online: 22 MAR 2011 | DOI: 10.1002/anie.201008147

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      The features you need: The first total synthesis of lycopodium alkaloid alopecuridine has been achieved in 13 steps in the longest linear sequence, and its biomimetic conversion into sieboldine A has been validated through a two-step oxidation. The synthesis features a semipinacol rearrangement of a functionalized medium-sized ring and an intramolecular pinacol coupling mediated by SmI2 (see scheme; Boc=tert-butoxycarbonyl).

    12. Asymmetric Catalysis

      Oxidative and Enantioselective Cross-Coupling of Aldehydes and Nitromethane Catalyzed by Diphenylprolinol Silyl Ether (pages 3920–3924)

      Prof. Dr. Yujiro Hayashi, Takahiko Itoh and Dr. Hayato Ishikawa

      Article first published online: 25 MAR 2011 | DOI: 10.1002/anie.201006885

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      Synthetically important β-substituted γ-nitro aldehydes have been synthesized with excellent enantioselectivity by the cross-coupling reaction of β-aryl substituted aldehydes or γ,δ-unsaturated aldehydes and nitromethane using 2,3-dichloro-5,6-dicyanoquinone (DDQ) and diphenylprolinol silyl ether as an oxidant and catalyst, respectively (see scheme; TMS=trimethylsilyl).

    13. Frustrated Lewis Pairs

      Geminal Phosphorus/Aluminum-Based Frustrated Lewis Pairs: C[BOND]H versus C[TRIPLE BOND]C Activation and CO2 Fixation (pages 3925–3928)

      Christian Appelt, Dr. Hauke Westenberg, Federica Bertini, Dr. Andreas W. Ehlers, Dr.  J. Chris Slootweg, Prof. Dr. Koop Lammertsma and Prof. Dr. Werner Uhl

      Article first published online: 21 MAR 2011 | DOI: 10.1002/anie.201006901

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      Catch it! Geminal phosphorus/aluminum-based frustrated Lewis pairs (FLPs) are easily obtained by hydroalumination of alkynylphosphines. These FLPs can activate terminal acetylenes by two competitive pathways, which were analyzed by DFT calculations, and they can bind carbon dioxide reversibly. Therefore, alongside polyfluorinated boranes, alanes are also ideal Lewis acids for FLP chemistry.

    14. Switchable Pores

      Observation of Pore-Switching Behavior in Porous Layered Carbon through a Mesoscale Order–Disorder Transformation (pages 3929–3933)

      Kasibhatta Kumara Ramanatha Datta, Dr. Dinesh Jagadeesan, Chidambar Kulkarni, Anushree Kamath, Dr. Ranjan Datta and Prof. Muthusamy Eswaramoorthy

      Article first published online: 29 MAR 2011 | DOI: 10.1002/anie.201007031

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      A structural chameleon: A porous layered carbon material (PLC) containing nanographene domains was prepared by graphitizing glucose within the nanoscopic voids of an aminoclay template. The size of the pores in the PLC was altered reversibly by a mesoscale order–disorder transformation brought about by an applied mechanical force (see picture). This pore flexibility was exploited for the size-selective separation of dye molecules.

    15. Photocatalysis

      Selective Formation of Imines by Aerobic Photocatalytic Oxidation of Amines on TiO2 (pages 3934–3937)

      Dr. Xianjun Lang, Dr. Hongwei Ji, Prof. Chuncheng Chen, Prof. Wanhong Ma and Prof. Jincai Zhao

      Article first published online: 4 MAR 2011 | DOI: 10.1002/anie.201007056

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      An oxygenation pathway: The title transformation involves a two-step process: a selective oxygenation step to generate aldehyde intermediates and a subsequent condensation step to afford the imine products (see scheme).

    16. H/D Exchange

      Mild and Selective H/D Exchange at the β Position of Aromatic α-Olefins by N-Heterocyclic Carbene–Hydride–Rhodium Catalysts (pages 3938–3942)

      Dipl.-Chem. Andrea Di Giuseppe, Dr. Ricardo Castarlenas, Prof. Jesús J. Pérez-Torrente, Prof. Fernando J. Lahoz, Dr. Victor Polo and Prof. Luis A. Oro

      Article first published online: 25 MAR 2011 | DOI: 10.1002/anie.201007238

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      Pacman bites selectively! Stable rhodium(III)–N-heterocyclic carbene–hydride complexes (Pacman-like catalysts) are highly active and selective catalysts for H/D exchange at the β position of aromatic α-olefins (see picture). The interplay between bulky N-heterocyclic carbene and quinolinate ligands determines the size of the steric window responsible for this selectivity.

    17. Hydrocarbon Conversion

      Synergy of Homogeneous and Heterogeneous Chemistry Probed by In Situ Spatially Resolved Measurements of Temperature and Composition (pages 3943–3946)

      Dr. Alessandro Donazzi, Dario Livio, Dr. Matteo Maestri, Prof. Alessandra Beretta, Prof. Gianpiero Groppi, Prof. Enrico Tronconi and Prof. Pio Forzatti

      Article first published online: 22 MAR 2011 | DOI: 10.1002/anie.201007346

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      By land or by air: Ultrafast catalytic processes for converting hydrocarbons at short contact times are characterized by extremely severe operating conditions. In situ sampling and detailed modeling of surface and gas-phase kinetics allowed the elucidation of the complex interplay between heterogeneous and homogenous pyrolytic routes to H2 and CO in the catalytic partial oxidation (CPO) of C3H8.

    18. Fatty Acid Hydrogenation

      Unprecedented Shape Selectivity in Hydrogenation of Triacylglycerol Molecules with Pt/ZSM-5 Zeolite (pages 3947–3949)

      An Philippaerts, Dr. Ir. Sabine Paulussen, Annika Breesch, Dr. Stuart Turner, Dr. Oleg I. Lebedev, Prof. Gustaaf Van Tendeloo, Prof. Bert Sels and Prof. Pierre Jacobs

      Article first published online: 18 MAR 2011 | DOI: 10.1002/anie.201007513

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      Well tuned: ZSM-5 with platinum nanoparticles preferably hydrogenates trans fatty acids over cis isomers in model triacylglycerols for geometric reasons. The central fatty acid chain reacts faster, pointing to pore mouth adsorption in a tuning fork conformation (see picture). This conformation induces stepwise hydrogenation, resulting in fast removal of the unstable central triene, while formation of saturated chains is limited.

    19. Asymmetric Synthesis

      Synthesis of syn and anti 1,4-Diols by Copper-Catalyzed Boration of Allylic Epoxides (pages 3950–3953)

      Dr. Mariola Tortosa

      Article first published online: 23 MAR 2011 | DOI: 10.1002/anie.201100613

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      Two sides of the same coin: Syn and anti 1,4-diols have been synthesized through the regio- and diastereoselective CuI-catalyzed boration of allylic epoxides (see scheme; pin=pinacolato, TES=triethylsilyl). In situ protection of the alcohol allows isolation of syn and anti 1,4-silyloxyboronates. Monoprotected 1,4-diols can be prepared by a one-pot addition–protection–oxidation sequence.

    20. Natural Product Synthesis

      Protecting-Group-Free Total Synthesis of (E)- and (Z)-Alstoscholarine (pages 3954–3957)

      Dr. Thibaud Gerfaud, Dr. Chunsong Xie, Dr. Luc Neuville and Prof. Dr. Jieping Zhu

      Article first published online: 31 MAR 2011 | DOI: 10.1002/anie.201100257

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      Looking for hidden symmetry: The first asymmetric total synthesis of pentacyclic compounds 1 and 2 has been accomplished starting from a cyclic meso-anhydride. The absolute configuration of the final products was set by an organocatalytic desymmetrization of the meso-anhydride. The economic synthesis is protecting-group-free and confirms the assigned absolute configuration.

    21. Semiconductor Nanocomposites

      Semiconductor Anisotropic Nanocomposites Obtained by Directly Coupling Conjugated Polymers with Quantum Rods (pages 3958–3962)

      Lei Zhao, Dr. Xinchang Pang, Ramkrishna Adhikary, Prof. Jacob W. Petrich and Prof. Zhiqun Lin

      Article first published online: 25 MAR 2011 | DOI: 10.1002/anie.201100200

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      Semiconductor organic–inorganic nanocomposites were synthesized by a catalyst-free click reaction of ethynyl-terminated polythiophene) with azide-functionalized CdSe nanorods. Such rationally designed nanocomposites possess a well-defined interface between polymer and nanorods, thereby facilitating electronic interaction.

    22. Asymmetric Catalysis

      Palladium-Catalyzed Enantioselective Intramolecular Hydroarylation of Alkynes To Form Axially Chiral 4-Aryl 2-Quinolinones (pages 3963–3967)

      Tetsuro Shibuya, Yu Shibata, Prof. Dr. Keiichi Noguchi and Prof. Dr. Ken Tanaka

      Article first published online: 31 MAR 2011 | DOI: 10.1002/anie.201100152

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      A long-awaited asymmetric version of the intramolecular hydroarylation of alkynes to form fused ring systems has been developed. A cationic palladium(II)/(S)-xyl-H8-binap complex was used to catalyze an enantioselective hydroarylation of alkynes at room temperature to furnish axially chiral 4-aryl 2-quinolinone derivatives in good yields with good enantioselectivity (see scheme; Bn=benzyl).

    23. Heterobimetallic Catalysis

      Assembling Zirconium and Calcium Moieties through an Oxygen Center for an Intramolecular Hydroamination Reaction: A Single System for Double Activation (pages 3968–3972)

      Arup Mukherjee, Dr. Sharanappa Nembenna, Tamal K. Sen, Dr. Sankaranarayana Pillai Sarish, Dr. Pradip Kr. Ghorai, Dr. Holger Ott, Prof. Dr. Dietmar Stalke, Dr. Swadhin K. Mandal and Prof. Dr. Herbert W. Roesky

      Article first published online: 23 MAR 2011 | DOI: 10.1002/anie.201100022

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      One for two: A zirconium compound combined with a main-group alkaline earth metal through an oxygen bridge has been synthesized. A number of primary and secondary aminoalkenes were successfully converted into cyclic products using this heterobimetallic complex as catalyst. The calcium center activates primary aminoalkenes, and the zirconium center activates secondary aminoalkenes.

    24. Switchable Materials

      Double Switching of a Magnetic Coordination Framework through Intraskeletal Molecular Rearrangement (pages 3973–3977)

      Dr. Dawid Pinkowicz, Dr. Robert Podgajny, Dr. Bartłomiej Gaweł, Dr. Wojciech Nitek, Prof. Dr. Wiesław Łasocha, Marcin Oszajca, Dr. Mariusz Czapla, Magdalena Makarewicz, Dr. Maria Bałanda and Prof. Dr. Barbara Sieklucka

      Article first published online: 22 MAR 2011 | DOI: 10.1002/anie.201100880

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      Stairway to heaven: An Mn2Nb coordination framework shows huge switching of the magnetic ordering temperature in two well-defined steps, finally reaching 100 K in its anhydrous form. The switching, controlled by removal/uptake of guest molecules, is related to an intraskeletal molecular rearrangement involving reversible formation/breaking of molecular bridges and translocation of an organic ligand on dehydration (see picture; VAC=vacuum).

    25. Heterogeneous Catalysis

      Selective Catalysis of the Aerobic Oxidation of Cyclohexane in the Liquid Phase by Carbon Nanotubes (pages 3978–3982)

      Prof. Hao Yu, Prof. Feng Peng, Jun Tan, Xiaowei Hu, Prof. Hongjuan Wang, Prof. Jian Yang and Prof. Wenxu Zheng

      Article first published online: 23 MAR 2011 | DOI: 10.1002/anie.201007932

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      Putting the N in nanotube: Carbon nanotubes (CNTs) catalyze the aerobic oxidation of cyclohexane into cyclohexanol, cyclohexanone, and adipic acid with excellent activity and controllable selectivity. The catalytic activity is further enhanced by nitrogen dopants in the nanotube (see diagram; AC=activated carbon, MWCNT=multiwalled CNT, N-CNT=nitrogen-doped CNT).

    26. DNA Actuator

      A DNA Tile Actuator with Eleven Discrete States (pages 3983–3987)

      Dr. Zhao Zhang, Eva M. Olsen, Mille Kryger, Niels V. Voigt, Thomas Tørring, Eda Gültekin, Morten Nielsen, Reza MohammadZadegan, Dr. Ebbe S. Andersen, Morten M. Nielsen, Prof. Jørgen Kjems, Dr. Victoria Birkedal and Prof. Kurt V. Gothelf

      Article first published online: 21 MAR 2011 | DOI: 10.1002/anie.201007642

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      Elegant control: A DNA actuator based on the most fundamental motif in DNA nanotechnology, the double crossover tile, has a linear sliding-gauge type of motion among eleven different states (see picture). The actuator has the ability to fine-tune the distances between attached components (resolution of less than 1 nm) for both physical studies and chemical control.

    27. Synthetic Enzymes

      Total Chemical Synthesis of an Integral Membrane Enzyme: Diacylglycerol Kinase from Escherichia coli (pages 3988–3992)

      Dr. Sunanda Lahiri, Manuel Brehs, Dr. Diana Olschewski and Prof. Dr. Christian F. W. Becker

      Article first published online: 23 MAR 2011 | DOI: 10.1002/anie.201006686

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      From the ground up: Chemical synthesis provided direct access to a catalytically active membrane-embedded kinase with three transmembrane domains (TMs). Three key segments formed from the individual amino acids (represented by red and gray balls) by solid-phase peptide synthesis were connected by native chemical ligation (NCL; see picture); the synthetic protein underwent spontaneous folding in detergent micelles. ATP=adenosine 5′-triphosphate.

    28. NMR Spectroscopy

      Structural Analysis of Large Protein Complexes Using Solvent Paramagnetic Relaxation Enhancements (pages 3993–3997)

      Dr. Tobias Madl, Dr. Thomas Güttler, Prof. Dr. Dirk Görlich and Prof. Dr. Michael Sattler

      Article first published online: 25 MAR 2011 | DOI: 10.1002/anie.201007168

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      The solvent helps out: Conventional protocols for structural analysis of protein complexes often fail if only sparse experimental data are available. NMR-spectroscopy-derived solvent paramagnetic relaxation enhancements (PREs) from a soluble spin label (picture) significantly improve the structural quality of a 150 kDa protein complex. This general protocol is an efficient approach for structural analysis of large protein complexes in solution.

    29. Natural Products

      Total Synthesis and Biological Evaluation of (−)-Englerin A and B: Synthesis of Analogues with Improved Activity Profile (pages 3998–4002)

      Lea Radtke, Dr. Matthieu Willot, Dr. Hongyan Sun, Dr. Slava Ziegler, Stephanie Sauerland, Prof. Carsten Strohmann, Dr. Roland Fröhlich, Dr. Peter Habenberger, Prof. Herbert Waldmann and Prof. Mathias Christmann

      Article first published online: 29 MAR 2011 | DOI: 10.1002/anie.201007790

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      The large-scale synthesis of englerin A (see scheme) and subsequent structure-activity relationship studies have led to the discovery of highly potent analogues. TBS=tert-butyldimethylsilyl.

    30. Molecular Recognition

      You have full text access to this OnlineOpen article
      From Crystal Packing to Molecular Recognition: Prediction and Discovery of a Binding Site on the Surface of Polo-Like Kinase 1 (pages 4003–4006)

      Paweł Śledź, Christopher J. Stubbs, Dr. Steffen Lang, Dr. Yong-Qing Yang, Dr. Grahame J. McKenzie, Prof. Ashok R. Venkitaraman, Dr. Marko Hyvönen and Prof. Chris Abell

      Article first published online: 29 MAR 2011 | DOI: 10.1002/anie.201008019

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      Picking the pocket: Crystal-packing interactions are present in every macromolecular structure solved with X-ray methods; however, they have not been extensively used to gain insight into molecular recognition. A novel approach is described to utilize these packing interactions for the discovery of a flexible binding site and ligands recognized by it (see picture).

    31. Molecular Magnets

      A Spectroscopic Investigation of Magnetic Exchange Between Highly Anisotropic Spin Centers (pages 4007–4011)

      Dr. Angelika B. Boeer, Dr. Anne-Laure Barra, Prof. Liviu F. Chibotaru, Prof. David Collison, Prof. Eric J. L. McInnes, Dr. Richard A. Mole, Dr. Giovanna G. Simeoni, Dr. Grigore A. Timco, Dr. Liviu Ungur, Dr. Tobias Unruh and Prof. Richard E. P. Winpenny

      Article first published online: 29 MAR 2011 | DOI: 10.1002/anie.201100306

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      Structurally similar, magnetically diverse: The exchange and Zeeman parameters of two dimetallic, six-coordinate cobalt(II) compounds—i.e., with orbitally degenerate metal ions—have been determined by a combination of high-resolution EPR and INS spectroscopies, together with ab intio calculations. It is suggested that the correlation between the local crystal field about the CoII centers and the superexchange pathway controls the magnetic interaction.

    32. Gels

      Tunable Angle-Independent Structural Color from a Phase-Separated Porous Gel (pages 4012–4015)

      Naomi Kumano, Prof. Takahiro Seki, Dr. Masahiko Ishii, Dr. Hiroshi Nakamura and Prof. Yukikazu Takeoka

      Article first published online: 31 MAR 2011 | DOI: 10.1002/anie.201008182

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      A porous gel exhibiting angle-independent structural color was obtained by a facile self-assembly approach. The porous swollen gel changes color reversibly in response to changes in solvent composition and temperature as a result of changes in the wavelength dispersions of the refractive indices of the gel portion and the solvent portion in the pores.

    33. Single-Molecule Magnets

      Wheel-Shaped ErIIIZnII3 Single-Molecule Magnet: A Macrocyclic Approach to Designing Magnetic Anisotropy (pages 4016–4019)

      Aika Yamashita, Akiko Watanabe, Prof. Dr. Shigehisa Akine, Prof. Dr. Tatsuya Nabeshima, Prof. Dr. Motohiro Nakano, Dr. Tomoo Yamamura and Prof. Dr. Takashi Kajiwara

      Article first published online: 23 MAR 2011 | DOI: 10.1002/anie.201008180

      Thumbnail image of graphical abstract

      Designer SMM: An ErIII-based single-molecule magnet (SMM) was synthesized by designing the ligand-field anisotropy around an ErIII ion in an equatorial arrangement of donors using a rigid and planar macrocyclic Schiff base ligand including three ZnII ions. The resulting ErIIIZnII3 complex (see picture; C gray, O red, N blue) behaves as a SMM with an energy barrier of 24.6(9) K for flipping of the molecular magnetic moment.

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      Preview: Angew. Chem. Int. Ed. 18/2011 (page 4021)

      Article first published online: 13 APR 2011 | DOI: 10.1002/anie.201190032

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