Angewandte Chemie International Edition

Cover image for Vol. 49 Issue 35

August 16, 2010

Volume 49, Issue 35

Pages 6003–6227

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Retraction
    6. News
    7. Author Profile
    8. Book Review
    9. Highlights
    10. Reviews
    11. Communications
    12. Retraction
    13. Preview
    1. Cover Picture: On the Reach of Chemical Synthesis: Creation of a Mini-Pipeline from an Academic Laboratory (Angew. Chem. Int. Ed. 35/2010) (page 6003)

      Rebecca M. Wilson and Samuel J. Danishefsky

      Version of Record online: 2 AUG 2010 | DOI: 10.1002/anie.201004265

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      Biologically active small molecules derived from natural sources, such as Panax ginseng plants and Streptomyces bacteria are shown in the title picture. In their Review on page 6032 ff., S. J. Danishefsky and R. M. Wilson demonstrate how chemical synthesis can be used to derive drug candidates from natural products.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Retraction
    6. News
    7. Author Profile
    8. Book Review
    9. Highlights
    10. Reviews
    11. Communications
    12. Retraction
    13. Preview
    1. Inside Cover: Reaction of Singlet Dioxygen with Phosphine–Borane Derivatives: From Transient Phosphine Peroxides to Crystalline Peroxoboronates (Angew. Chem. Int. Ed. 35/2010) (page 6004)

      Susana Porcel, Ghenwa Bouhadir, Nathalie Saffon, Laurent Maron and Didier Bourissou

      Version of Record online: 22 JUN 2010 | DOI: 10.1002/anie.201003227

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      Ambiphilic phosphine–boronates readily split singlet dioxygen under mild conditions. As described by D. Bourissou and co-workers in their Communication on page 6186 ff., the initially formed phosphine peroxides spontaneously rearrange into stable crystalline peroxoboronates. Artwork: Christian Pradel.

  3. Graphical Abstract

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Retraction
    6. News
    7. Author Profile
    8. Book Review
    9. Highlights
    10. Reviews
    11. Communications
    12. Retraction
    13. Preview
    1. You have free access to this content
      Retraction: Facile Palladium-Catalyzed Arylation of Heterocycles and Nonactivated Arenes with Aryl Chlorides (page 6017)

      Jan Pschierer and Herbert Plenio

      Version of Record online: 12 AUG 2010 | DOI: 10.1002/anie.201004790

      This article corrects:
  5. News

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Retraction
    6. News
    7. Author Profile
    8. Book Review
    9. Highlights
    10. Reviews
    11. Communications
    12. Retraction
    13. Preview
    1. Carsten Schmuck (page 6024)

      Version of Record online: 30 JUL 2010 | DOI: 10.1002/anie.201004128

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      “My favorite subjects at school were mathematics, chemistry, and French. The three qualities that make a good scientist are curiosity, enthusiasm, and persistence …” This and more about Carsten Schmuck can be found on page 6024.

  7. Book Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Retraction
    6. News
    7. Author Profile
    8. Book Review
    9. Highlights
    10. Reviews
    11. Communications
    12. Retraction
    13. Preview
    1. Organic Azides. Syntheses and Applications. Edited by Stefan Bräse and Klaus Banert. (page 6025)

      Gwilherm Evano

      Version of Record online: 28 JUL 2010 | DOI: 10.1002/anie.201003406

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      John Wiley & Sons, Hoboken 2009. 536 pp., hardcover € 139.00.—ISBN 978-0470519981

  8. Highlights

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Retraction
    6. News
    7. Author Profile
    8. Book Review
    9. Highlights
    10. Reviews
    11. Communications
    12. Retraction
    13. Preview
    1. Phthalide Synthesis

      Catalytic Intramolecular Ketone Hydroacylation: Enantioselective Synthesis of Phthalides (pages 6026–6027)

      Michael C. Willis

      Version of Record online: 20 MAY 2010 | DOI: 10.1002/anie.201000159

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      Controlling carbonyl groups: Identification of the correct ligand/counterion combination was essential to allow the efficient and selective rhodium-catalyzed conversion of a series of ketobenzaldehydes into the corresponding phthalides using the title reaction (see scheme; cod=cycloocta-l,5-diene).

    2. Mechanochemistry

      Reconfiguration of Stereoisomers under Sonomechanical Activation (pages 6028–6030)

      Giancarlo Cravotto and Pedro Cintas

      Version of Record online: 20 JUL 2010 | DOI: 10.1002/anie.201001360

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      Let's twist to the music: In an unprecedented reconfiguration of thermally stable atropisomers, mechanical stress induced by ultrasound waves on a polymer-bound substrate (see structure) did effectively cause racemization facilitating enantiomer interconversion.

      Corrected by:

      Corrigendum: Corrigendum: Reconfiguration of Stereoisomers under Sonomechanical Activation

      Vol. 54, Issue 28, 8021, Version of Record online: 30 JUN 2015

  9. Reviews

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Retraction
    6. News
    7. Author Profile
    8. Book Review
    9. Highlights
    10. Reviews
    11. Communications
    12. Retraction
    13. Preview
    1. Drug Discovery

      On the Reach of Chemical Synthesis: Creation of a Mini-Pipeline from an Academic Laboratory (pages 6032–6056)

      Rebecca M. Wilson and Samuel J. Danishefsky

      Version of Record online: 26 JUL 2010 | DOI: 10.1002/anie.201000775

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      Successful journey: This retrospective Review describes investigations into the total synthesis and evaluation of biologically active small molecules (such as iso-fludelone; see structure), as well as the development of a program directed toward the chemical synthesis of therapeutically relevant larger molecules, including the glycoprotein erythropoietin.

    2. Carbon Dioxide Capture

      Carbon Dioxide Capture: Prospects for New Materials (pages 6058–6082)

      Deanna M. D'Alessandro, Berend Smit and Jeffrey R. Long

      Version of Record online: 22 JUL 2010 | DOI: 10.1002/anie.201000431

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      Getting CO2under control: This Review highlights the challenges for carbon capture and storage technologies which have been proposed to reduce CO2 emissions from large point sources. The most recent developments in new materials and emerging concepts for CO2 separations by absorption, adsorption, and membranes, amongst other approaches, are discussed, with particular attention on progress in the burgeoning field of metal–organic frameworks (see example).

  10. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Retraction
    6. News
    7. Author Profile
    8. Book Review
    9. Highlights
    10. Reviews
    11. Communications
    12. Retraction
    13. Preview
    1. Surface Structure Elucidation

      Real-Space Observation of Surface Termination of a Complex Metal Oxide Catalyst (pages 6084–6089)

      Wei Zhang, Annette Trunschke, Robert Schlögl and Dangsheng Su

      Version of Record online: 22 JUN 2010 | DOI: 10.1002/anie.201000910

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      Looking good: High-resolution TEM can be used to determine the surface structure of a metal oxide catalyst in real space. The picture shows HR-TEM images of one catalyst particle along 〈001〉 direction far from Scherzer focus. The perimeter of the particle is highlighted by the fractured structural units.

    2. Protein Synthesis

      Synthesis of the Rheb and K-Ras4B GTPases (pages 6090–6095)

      Yong-Xiang Chen, Sebastian Koch, Katharina Uhlenbrock, Katrin Weise, Debapratim Das, Lothar Gremer, Luc Brunsveld, Alfred Wittinghofer, Roland Winter, Gemma Triola and Herbert Waldmann

      Version of Record online: 22 JUL 2010 | DOI: 10.1002/anie.201001884

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      Now available! Farnesylated and carboxymethylated Rheb (see picture) and K-Ras4B GTPases were synthesized in useful amounts by a combination of expressed protein ligation and solid-phase lipopeptide synthesis. The functionality of the proteins was proven by biochemical, biophysical, and cell-based investigations.

    3. Polyoxometalate Chemistry

      Zinc(II) Containing γ-Keggin Sandwich-Type Silicotungstate: Synthesis in Organic Media and Oxidation Catalysis (pages 6096–6100)

      Yuji Kikukawa, Kazuya Yamaguchi and Noritaka Mizuno

      Version of Record online: 15 JUL 2010 | DOI: 10.1002/anie.201001468

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      Zinc in: Polyoxometalate 1 reacts with Zn2+ ions in acetone to form a novel sandwich-type POM 2 in almost quantitative yield. The H2O2-based oxidation of secondary alcohols with 2 efficiently proceeds, with an activity and chemoselectivity that is very different from those of tungsten-based catalysts including 1 (see scheme; green Zn).

    4. Self-Assembled Monolayers

      Oligomers and Cyclooligomers of Rigid Phenylene–Ethynylene–Butadiynylenes: Synthesis and Self-Assembled Monolayers (pages 6101–6105)

      Stefan-S. Jester, Natalia Shabelina, Stephan M. Le Blanc and Sigurd Höger

      Version of Record online: 20 JUL 2010 | DOI: 10.1002/anie.201001625

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      Starting from the same bisacetylene, different reaction conditions (palladium or copper catalysis) selectively yielded cyclic or acyclic oligomers with n=2–6 (see picture for n=3) linked by freely rotating corner units. STM images of self-assembled monolayers revealed the difference in the adsorption behavior of the acyclic and cyclic oligomers.

    5. Organocatalysis

      Mechanistic Complexity in Organo–SOMO Activation (pages 6106–6110)

      James J. Devery III, Jay C. Conrad, David W. C. MacMillan and Robert A. Flowers II

      Version of Record online: 14 JUL 2010 | DOI: 10.1002/anie.201001673

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      Wet chemistry: Organo-SOMO activation is an intricate process. The catalyst is deactivated in the absence of H2O and its concentration is maintained with 2 equivalents of H2O. The kinetic role of ceric ammonium nitrate (CAN) is masked by phase transfer and its limited solubility is enhanced by added H2O. Mechanistic studies show that careful addition of H2O to dried reagents greatly enhances reaction. TMS=trimethylsilyl.

    6. Enantioselectivity

      Enantioselectivity of Haloalkane Dehalogenases and its Modulation by Surface Loop Engineering (pages 6111–6115)

      Zbynek Prokop, Yukari Sato, Jan Brezovsky, Tomas Mozga, Radka Chaloupkova, Tana Koudelakova, Petr Jerabek, Veronika Stepankova, Ryo Natsume, Jan G. E. van Leeuwen, Dick B. Janssen, Jan Florian, Yuji Nagata, Toshiya Senda and Jiri Damborsky

      Version of Record online: 19 JUL 2010 | DOI: 10.1002/anie.201001753

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      In the loop: Engineering of the surface loop in haloalkane dehalogenases affects their enantiodiscrimination behavior. The temperature dependence of the enantioselectivity (lnE versus 1/T) of β-bromoalkanes by haloalkane dehalogenases is reversed (red data points) by deletion of the surface loop; the selectivity switches back when an additional single-point mutation is made. This behavior is not observed for α-bromoesters.

    7. Ultrathin Films

      Covalent Layer-by-Layer Assembly and Solvent Memory of Multilayer Films from Homobifunctional Poly(dimethylsiloxane) (pages 6116–6119)

      Rohama Gill, Muhammad Mazhar, Olivier Félix and Gero Decher

      Version of Record online: 21 JUL 2010 | DOI: 10.1002/anie.200907161

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      Catching the end groups: A simple procedure was used for the covalent layer-by-layer assembly of homobifunctional H2N-poly(dimethoxysilane)-NH2 on SiO2 surfaces that leads to robust layer-by-layer films of optical quality (see picture; photo on left) despite the use of non-purified commercial starting materials. The films show a solvent memory for swelling and de-swelling when immersed in the corresponding solvent for each polymer.

    8. Monolayers

      Nanotexture Switching of Single-Layer Hexagonal Boron Nitride on Rhodium by Intercalation of Hydrogen Atoms (pages 6120–6124)

      Thomas Brugger, Haifeng Ma, Marcella Iannuzzi, Simon Berner, Adolf Winkler, Jürg Hutter, Jürg Osterwalder and Thomas Greber

      Version of Record online: 14 JUL 2010 | DOI: 10.1002/anie.201001064

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      Playing nano-tectonics: The interaction of atomic hydrogen with a single layer of hexagonal boron nitride on rhodium leads to the removal of the h-BN surface corrugation (see picture; blue region: corrugated, orange region: flat). This change of surface texture arises from the intercalation of hydrogen atoms between the h-BN skin and the metal, and can be restored by annealing to about 600 K to expel the hydrogen atoms.

    9. Analyzing Works of Art

      Revealing the sfumato Technique of Leonardo da Vinci by X-Ray Fluorescence Spectroscopy (pages 6125–6128)

      Laurence de Viguerie, Philippe Walter, Eric Laval, Bruno Mottin and V. Armando Solé

      Version of Record online: 14 JUL 2010 | DOI: 10.1002/anie.201001116

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      Not just a pretty face: Non-invasive X-ray fluorescence spectroscopy was used to reveal the sfumato paint layer stacking method that was used by Leonardo da Vinci to paint the faces in seven of his paintings. A strong diversity in his technique could clearly be seen with this method.

    10. Superhydrophobic Coatings

      Bioinspired Self-Healing Superhydrophobic Coatings (pages 6129–6133)

      Yang Li, Long Li and Junqi Sun

      Version of Record online: 19 JUL 2010 | DOI: 10.1002/anie.201001258

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      Heal thyself! Self-healing superhydrophobic coatings are fabricated by preserving healing agents of reacted fluoroalkylsilane in layered polymeric coatings that are porous and rigidly flexible. When the top layer of fluoroalkyl chains decomposes or the coatings are scratched, the healing agents migrate to the surface to restore the superhydrophobicity of the coatings (see picture).

    11. Fluorescent Probes

      A Significant Improvement of the Efficacy of Radical Oxidant Probes by the Kinetic Isotope Effect (pages 6134–6138)

      Kousik Kundu, Sarah F. Knight, Seungjun Lee, W. Robert Taylor and Niren Murthy

      Version of Record online: 19 JUL 2010 | DOI: 10.1002/anie.201002228

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      A breath of fresh air: The rate of aerial oxidation of dihydroethidium and hydrocyanine radical oxidant probes can be selectively reduced by deuteration (see picture). The reaction rate between the deuterated compounds and the superoxide radical was reduced by a much smaller factor because of mechanistic differences between the two reactions. The deuterated probes are more effective than their hydrogen analogues in vitro, in cell culture, and in vivo.

    12. Total Synthesis

      Total Synthesis of Chloptosin (pages 6139–6142)

      Alexander J. Oelke, David J. France, Tatjana Hofmann, Georg Wuitschik and Steven V. Ley

      Version of Record online: 19 JUL 2010 | DOI: 10.1002/anie.201002880

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      Two is better that one: A new organocatalytic route for the asymmetric preparation of the embedded piperazic acids and a Stille coupling of an ortho-chloropyrroloindole served as key steps in the total synthesis of the dimeric cyclopeptide chloptosin (see structure).

    13. Niobium Compounds

      σ-Organoniobium Compounds with [NbR4] and NbR4 Stoichiometries (pages 6143–6146)

      Pablo J. Alonso, Irene Ara, Ana B. Arauzo, M. Angeles García-Monforte, Babil Menjón and Conrado Rillo

      Version of Record online: 22 JUL 2010 | DOI: 10.1002/anie.201002666

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      Securely nested: The first examples of σ-organoniobium compounds with [NbIIIR4] and NbIVR4 stoichiometries are reported. The Nb centers within the [Nb(C6Cl5)4]q units (q=0, 1) are located in triakis tetrahedral environments formed by the combination of inner NbC4 (see picture; gray) and outer NbCl4 (green) tetrahedra.

    14. Total Synthesis

      An Enantioselective Total Synthesis of (+)-Peloruside A (pages 6147–6150)

      Meredeth A. McGowan, Christian P. Stevenson, Matthew A. Schiffler and Eric N. Jacobsen

      Version of Record online: 28 JUN 2010 | DOI: 10.1002/anie.201002177

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      Short and sweet: Chiral epoxides, prepared using (salen)cobalt-catalyzed ring-opening reactions, and a chromium catalyst controlled hetero-Diels–Alder reaction were used to set most of the stereocenters in the total synthesis of the microtubule-stabilizing agent peloruside A. The overall highly convergent route required only 20 steps in the longest linear sequence. MOM=methoxymethyl, TBS=tert-butyldimethylsilyl.

    15. Natural Products

      Total Synthesis of Peloruside A through Kinetic Lactonization and Relay Ring-Closing Metathesis Cyclization Reactions (pages 6151–6155)

      Thomas R. Hoye, Junha Jeon, Lucas C. Kopel, Troy D. Ryba, Manomi A. Tennakoon and Yini Wang

      Version of Record online: 19 JUL 2010 | DOI: 10.1002/anie.201002293

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      The other side: A convergent total synthesis of peloruside A (1) is described. The key strategic features are a diastereoselective lactonization to generate a C5–C9 valerolactone from the C2-symmetric ketone 3, and a relay ring-closing metathesis reaction to produce a dehydrovalerolactone 2. A new isomer of 1, the valerolactone isopeloruside A (iso-1), was identified. MOM=methoxymethyl.

    16. Metal Nanocrystals

      Size- and Shape-Selective Synthesis of Metal Nanocrystals and Nanowires Using CO as a Reducing Agent (pages 6156–6159)

      Yijin Kang, Xingchen Ye and Christopher B. Murray

      Version of Record online: 26 JUL 2010 | DOI: 10.1002/anie.201003383

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      Putting the pedal to the metal: A facile strategy for the synthesis of metal nanocrystals is demonstrated that employs carbon monoxide as a reducing agent. Highly monodisperse platinum nanocubes, spherical palladium nanocrystals, and ultrathin gold nanowires can be produced within 15 minutes.

    17. Asymmetric Catalysis

      Catalytic Asymmetric Bromoamination of Chalcones: Highly Efficient Synthesis of Chiral α-Bromo-β-Amino Ketone Derivatives (pages 6160–6164)

      Yunfei Cai, Xiaohua Liu, Yonghai Hui, Jun Jiang, Wentao Wang, Weiliang Chen, Lili Lin and Xiaoming Feng

      Version of Record online: 20 JUL 2010 | DOI: 10.1002/anie.201002355

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      Stand and deliver: The first highly regio- and enantioselective bromoamination of chalcones has been developed which proceeds via an unusual bromonium-based mechanism to deliver the title compounds. Excellent results were obtained using 0.05 mol % of the C2-symmetric N,N′-dioxide/scandium(III) complex under mild conditions (see scheme).

    18. Natural Product Synthesis

      Total Synthesis of (−)-Virginiamycin M2 (pages 6165–6168)

      Jie Wu and James S. Panek

      Version of Record online: 20 JUL 2010 | DOI: 10.1002/anie.201002220

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      Has a nice ring to it: A concise and modular total synthesis of the naturally occurring antibiotic virginiamycin M2 is described. A Barbier-type cyclization was used to close the 23-membered macrocycle and deliver virginiamycin M2 in 19 steps from a chiral organosilane.

    19. C[BOND]H Activation

      Constructing Multiply Substituted Arenes Using Sequential Palladium(II)-Catalyzed C[BOND]H Olefination (pages 6169–6173)

      Keary M. Engle, Dong-Hui Wang and Jin-Quan Yu

      Version of Record online: 14 JUL 2010 | DOI: 10.1002/anie.201002077

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      A balancing act: Complementary catalytic systems are described, in which the reactivity/selectivity balance in PdII-catalyzed ortho-C[BOND]H olefination can be modulated to enable sequential C[BOND]H functionalization for the rapid preparation of 1,2,3-trisubstituted arenes 1. Additionally, a rare example of iterative C[BOND]H activation, in which a newly installed functional group directs subsequent C[BOND]H activation has been demonstrated (2).

    20. Azo Compounds

      Copper-Catalyzed Aerobic Oxidative Dehydrogenative Coupling of Anilines Leading to Aromatic Azo Compounds using Dioxygen as an Oxidant (pages 6174–6177)

      Chun Zhang and Ning Jiao

      Version of Record online: 22 JUL 2010 | DOI: 10.1002/anie.201001651

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      In the air tonight: A novel approach to symmetric and unsymmetric aromatic azo compounds from simple anilines catalyzed by inexpensive CuBr has been disclosed. Air (or dioxygen) was used as an oxidant under mild reaction conditions, with H2O as the byproduct, to make this transformation environmentally benign and very easy to handle.

    21. Phosphorus Chemistry

      Preparation of Ligand-Stabilized [P4O4]2+ by Controlled Hydrolysis of a Janus Head Type Diphosphorus Trication (pages 6178–6181)

      Jan J. Weigand, Kai-Oliver Feldmann, Antje K. C. Echterhoff, Andreas W. Ehlers and Koop Lammertsma

      Version of Record online: 19 JUL 2010 | DOI: 10.1002/anie.201001363

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      A door to new opportunities: The stepwise hydrolysis of a diphosphorus trication is an efficient method for the preparation of an unusual ligand-stabilized dication that contains a novel cationic [P4O4]2+ framework (see Scheme; gray C, blue N, red O, orange P). This approach demonstrates the potential of the diphosphorus trication as a source for phosphorus building blocks to be used in the construction of novel cationic ring and cluster systems.

    22. NMR Spectroscopy

      Scavenging Free Radicals To Preserve Enhancement and Extend Relaxation Times in NMR using Dynamic Nuclear Polarization (pages 6182–6185)

      Pascal Miéville, Puneet Ahuja, Riddhiman Sarkar, Sami Jannin, Paul R. Vasos, Sandrine Gerber-Lemaire, Mor Mishkovsky, Arnaud Comment, Rolf Gruetter, Olivier Ouari, Paul Tordo and Geoffrey Bodenhausen

      Version of Record online: 21 JUL 2010 | DOI: 10.1002/anie.201000934

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      Vitamin C for longer lifetimes: N-oxide radicals that are widely used for dynamic nuclear polarization can be reduced by scavengers such as sodium ascorbate (vitamin C) during the dissolution process, thus diminishing losses of polarization during the transfer and extending transverse and longitudinal relaxation times in NMR spectroscopy (see picture).

    23. Singlet Dioxygen Fixation

      Reaction of Singlet Dioxygen with Phosphine–Borane Derivatives: From Transient Phosphine Peroxides to Crystalline Peroxoboronates (pages 6186–6189)

      Susana Porcel, Ghenwa Bouhadir, Nathalie Saffon, Laurent Maron and Didier Bourissou

      Version of Record online: 22 JUN 2010 | DOI: 10.1002/anie.201000520

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      Singlet dioxygen is readily split by phosphine–boronates under mild conditions. The initially formed phosphine peroxides spontaneously rearrange by B[RIGHTWARDS ARROW]O migration. The resulting peroxoboronates have been structurally characterized, and their ability to undergo oxygen transfer reactions substantiated.

    24. Conjugated Oligomers

      A Modular Synthetic Approach to Conjugated Pentacene Di-, Tri-, and Tetramers (pages 6190–6194)

      Dan Lehnherr, Adrian H. Murray, Robert McDonald and Rik R. Tykwinski

      Version of Record online: 19 JUL 2010 | DOI: 10.1002/anie.201000555

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      Mind the band gap: π-conjugated pentacene di-, tri-, and tetramers can be synthesized by using a versatile building block in Hay homocoupling as well as Cadiot–Chodkiewicz cross-coupling reactions. This modular approach allows the evaluation of solubility, stability, and the HOMO–LUMO gap as a function of compound length. Long-range three-dimensional π overlap occurs in the iBu3Si-substituted pentacene dimer (see figure; n=2).

    25. Iterative Synthesis

      Asymmetric Conjugate Silyl Transfer in Iterative Catalytic Sequences: Synthesis of the C7–C16 Fragment of (+)-Neopeltolide (pages 6195–6198)

      Eduard Hartmann and Martin Oestreich

      Version of Record online: 20 JUL 2010 | DOI: 10.1002/anie.201002916

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      Matched or mismatched, that is not the question! The anti,anti configuration of the C7–C16 fragment of (+)-neopeltolide is stereoselectively installed in an iterative sequence of catalyst-controlled Si group and Me group transfers, even with mismatched selectivity in the former (Si=Me2PhSi, see scheme; TBS=tert-butyldimethylsilyl).

    26. Biomimetic Synthesis

      Biomimetic Synthesis of (−)-Pycnanthuquinone C through the Diels–Alder Reaction of a Vinyl Quinone (pages 6199–6202)

      Florian Löbermann, Peter Mayer and Dirk Trauner

      Version of Record online: 19 JUL 2010 | DOI: 10.1002/anie.201001862

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      Three strikes and you're out! A concise, asymmetric synthesis of pycnanthuquinone C underscores the biosynthetic relevance of Diels–Alder reactions of vinyl quinones. The relative and absolute configuration of the natural product has been elucidated.

    27. Vibrational Spectroscopy

      Chirality Recognition in Menthol and Neomenthol: Preference for Homoconfigurational Aggregation (pages 6203–6206)

      Merwe Albrecht, Jan Will and Martin A. Suhm

      Version of Record online: 22 JUL 2010 | DOI: 10.1002/anie.201001565

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      Cool chirality: L-Menthol (see ball-and-stick model), a most important fragrance, is characterized in terms of its conformation, selective aggregation, and sublimation. The data indicate a preference for homoconfigured aggregates.

    28. Push–Pull Chromophores

      Homoconjugated Push–Pull and Spiro Systems: Intramolecular Charge-Transfer Interactions and Third-Order Optical Nonlinearities (pages 6207–6211)

      Shin-ichiro Kato, Marten T. Roberts Beels, Philip La Porta, W. Bernd Schweizer, Corinne Boudon, Jean-Paul Gisselbrecht, Ivan Biaggio and François Diederich

      Version of Record online: 20 JUL 2010 | DOI: 10.1002/anie.201002236

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      Homoconjugated push–pull chromophores are obtained by [2+2] cycloaddition of 2,3-dichloro-5,6-dicyano-p-benzoquinone to anilino or ferrocene donor-substituted alkynes, and in one case a spiro compound (see picture: examples with corresponding electron adsorption spectra; C gray, Cl green, N blue, O red). Significant third-order optical nonlinearities could be measured for the first time for homoconjugated push–pull systems.

    29. Metal–Organic Frameworks

      Reduction of a Metal–Organic Framework by an Organometallic Complex: Magnetic Properties and Structure of the Inclusion Compound [(η5-C5H5)2Co]0.5@MIL-47(V) (pages 6212–6215)

      Mikhail Meilikhov, Kirill Yusenko, Antonio Torrisi, Bettina Jee, Caroline Mellot-Draznieks, Andreas Pöppl and Roland A. Fischer

      Version of Record online: 22 JUL 2010 | DOI: 10.1002/anie.200907126

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      The stoichiometric reduction of the MIL-47(V) framework (see picture; green VO6 octahedra) was performed using cobaltocene as an organometallic reducing agent. The formation of a mixed-valence compound with a V3+/V4+ ratio of 1:1 was confirmed by magnetic susceptibility measurements. Incorporation of cobaltocene into the MIL-47(V) framework can be reversed upon treatment with water.

    30. RNA–Ligand Interactions

      Highly Modular Structure and Ligand Binding by Conformational Capture in a Minimalistic Riboswitch (pages 6216–6219)

      Elke Duchardt-Ferner, Julia E. Weigand, Oliver Ohlenschläger, Sina R. Schmidtke, Beatrix Suess and Jens Wöhnert

      Version of Record online: 14 JUL 2010 | DOI: 10.1002/anie.201001339

      Thumbnail image of graphical abstract

      Be prepared: The structure of an synthetic neomycin riboswitch RNA (N1) is investigated by NMR spectroscopy. A largely disordered free structural ensemble also contains a compact conformation that resembles the ligand-bound state thus suggesting a binding mechanism by conformational capture (see scheme, red=ligand).

    31. Self-Assembled Monolayers

      Isophthalic Acid: A Basis for Highly Ordered Monolayers (pages 6220–6223)

      Izabela Cebula, Cai Shen and Manfred Buck

      Version of Record online: 15 JUL 2010 | DOI: 10.1002/anie.201002082

      Thumbnail image of graphical abstract

      Standing on their own two feet: Underpotential deposition of Cu on Au(111) yields a surface onto which 1,3-benzenedicarboxylic acid (IPA) and 1,3,5-benzenetricarboxylic acid (TMA) adsorb in a bipodal configuration. Both molecules form highly crystalline isostructural monolayers, thus demonstrating the potential of the IPA moiety as tecton for self-assembled monolayers. A thin film of a Cu–TMA coordination polymer was grown on a patterned TMA monolayer.

  11. Retraction

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    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Retraction
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    7. Author Profile
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    1. Direct Cross-Coupling

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    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Retraction
    6. News
    7. Author Profile
    8. Book Review
    9. Highlights
    10. Reviews
    11. Communications
    12. Retraction
    13. Preview
    1. You have free access to this content

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