Angewandte Chemie International Edition

Cover image for Vol. 48 Issue 23

May 25, 2009

Volume 48, Issue 23

Pages 4079–4253

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    12. Preview
    1. Cover Picture: Selectivity Control in Gold-Mediated Esterification of Methanol (Angew. Chem. Int. Ed. 23/2009) (page 4079)

      Bingjun Xu, Xiaoying Liu, Jan Haubrich, Robert J. Madix and Cynthia M. Friend

      Version of Record online: 19 MAY 2009 | DOI: 10.1002/anie.200990117

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      Atomic oxygen adsorbed on metallic gold promotes the low-temperature transformation of methanol to methyl formate, formaldehyde, and formic acid. The reactions occur with oxygen-containing gold nanoparticles (ca. 2 nm in diameter), which form when Au(111) is oxidized with ozone. The detailed reaction mechanism is discussed by C. M. Friend and co-workers in the Communication on page 4206 ff.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
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    1. Inside Cover: Matrix-Free Formation of Gas-Phase Biomolecular Ions by Soft Cluster-Induced Desorption (Angew. Chem. Int. Ed. 23/2009) (page 4080)

      Christoph. R. Gebhardt, Anna Tomsic, Hartmut Schröder, Michael Dürr and Karl L. Kompa

      Version of Record online: 19 MAY 2009 | DOI: 10.1002/anie.200990118

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      Mass spectrometry of biomolecules has developed into a key technology in bioanalytics. As described by C. R. Gebhardt, M. Dürr et al. in their Communication on page 4162 ff., surface collisions of neutral molecular clusters can be used for soft formation of the required gas-phase biomolecular ions. Upon impact on a surface, the clusters provide the energy for desorption of the adsorbed biomolecules and serve as a transient matrix. Subsequent evaporative cooling prevents shattering and finally leads to an isolated biomolecular ion in the gas phase.

  3. Graphical Abstract

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

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    12. Preview
    1. Wonwoo Nam (page 4100)

      Version of Record online: 29 APR 2009 | DOI: 10.1002/anie.200901784

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      “The secret of being a successful scientist is to devote oneself to one thing. The biggest challenge facing scientists is to recruit young talented students who are willing to enjoy ventures in science. …” This and more about Wonwoo Nam can be found on page 4100.

  6. News

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    12. Preview
    1. Tin Chemistry.Fundamentals, Frontiers, and Applications. Edited by Alwyn G. Davies, Marcel Gielen, Keith H. Pannell and Edward R. T. Tiekink. (pages 4102–4103)

      Stefanie Dehnen

      Version of Record online: 19 MAY 2009 | DOI: 10.1002/anie.200900842

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      John Wiley & Sons, Chichester 2008. 752 pp., hardcover € 199.00.—ISBN 978-0470517710

  8. Highlights

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
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    8. Book Review
    9. Highlights
    10. Review
    11. Communications
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    1. Hydrocarboxylation

      Synthesis of β,γ-Unsaturated Acids from Allenes and Carbon Dioxide (pages 4104–4105)

      Michael North

      Version of Record online: 28 APR 2009 | DOI: 10.1002/anie.200900638

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      Hidden talent: Often perceived to be too thermodynamically and kinetically inert to be a useful chemical feedstock, carbon dioxide adds to allenes under exceptionally mild reductive conditions in the presence of a palladium pincer complex to give β,γ-unsaturated carboxylic acids (see scheme). This transformation is discussed in the context of the requirements for CO2 fixation. DMF=N,N-dimethylformamide, Tf=trifluoromethanesulfonyl.

    2. Nanoparticle Bombs

      Nanoparticle Missiles from Exploding Polyelectrolyte Capsules (pages 4106–4108)

      Lars Dähne

      Version of Record online: 16 APR 2009 | DOI: 10.1002/anie.200900121

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      Out with a bang! Microcapsules have been prepared which, as a result of an explosion triggered by an external stimulus, distribute nanoparticles throughout the local environment both efficiently and rapidly (see picture). In this way a principle found in nature for the dispersal of seeds and defensive materials has now been realized in nanotechnology and might be utilized, for example, for the better distribution of drugs in organs.

    3. Cluster Compounds

      Bridging the Gap between Coordination and Cluster Compounds: Unusual Bonding Modes for Zinc (pages 4109–4111)

      Deborah L. Kays and Simon Aldridge

      Version of Record online: 9 APR 2009 | DOI: 10.1002/anie.200900491

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      Inner virtue: The reaction of [Mo0(GaCp*)6] with ZnMe2 yields the novel multinuclear zinc system [MoZn12Me9Cp*3] which geometrically resembles a classical Wade–Mingos cluster (with an interstitial molybdenum atom, see picture). In reality, its electronic structure features little direct Zn[BOND]Zn bonding, relying instead on Mo[BOND]Zn three-center, two-electron bonds spanning the body diagonals of the approximately icosahedral framework.

  9. Review

    1. Top of page
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    8. Book Review
    9. Highlights
    10. Review
    11. Communications
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    1. Palladium Catalysis

      Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds (pages 4114–4133)

      Anne Brennführer, Helfried Neumann and Matthias Beller

      Version of Record online: 8 MAY 2009 | DOI: 10.1002/anie.200900013

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      A CO group richer: (Hetero)arenes are vital intermediates in the manufacture of agrochemicals, dyes, pharmaceuticals, and other industrial products. In the past decades transition-metal-catalyzed coupling reactions of aryl halides with all types of nucleophiles have been developed. This Review summarizes recent work in the area of palladium-catalyzed carbonylation reactions of aryl halides and related compounds (see scheme).

  10. Communications

    1. Top of page
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    1. DNA Nanotechnology

      Icosahedral DNA Nanocapsules by Modular Assembly (pages 4134–4137)

      Dhiraj Bhatia, Shabana Mehtab, Ramya Krishnan, Shantinath S. Indi, Atanu Basu and Yamuna Krishnan

      Version of Record online: 16 FEB 2009 | DOI: 10.1002/anie.200806000

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      It's a trap! DNA polyhedra formed through molecular self-assembly may function as nanocapsules for the targeted delivery of encapsulated entities. This functional aspect was demonstrated for the most complex DNA-based platonic solid: During the stepwise amalgamation of discrete polyhedra to form icosahedra, gold nanoparticles (GNPs) were encapsulated from solution (see illustration and TEM image of icosahedral cages containing GNPs).

    2. Calcium Sensors

      Bioinspired Colorimetric Detection of Calcium(II) Ions in Serum Using Calsequestrin-Functionalized Gold Nanoparticles (pages 4138–4141)

      Sunghyun Kim, Jeong Won Park, Dongkyu Kim, Daejin Kim, In-Hyun Lee and Sangyong Jon

      Version of Record online: 7 MAY 2009 | DOI: 10.1002/anie.200900071

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      Seeing is sensing: Calsequestrin (CSQ) functionalized gold nanoparticles undergo calcium-dependent CSQ polymerization, which results in a clear color change (see picture) together with precipitation. The sensing system is specific for Ca2+ ions and the differences between normal and disease-associated abnormal (hypercalcemia) Ca2+ ion levels in serum can be distinguished with the naked eye.

    3. Molecular Targeting

      A Xenon-129 Biosensor for Monitoring MHC–Peptide Interactions (pages 4142–4145)

      Andreas Schlundt, Wolfgang Kilian, Michael Beyermann, Jana Sticht, Sebastian Günther, Sabine Höpner, Kirsten Falk, Olaf Roetzschke, Lorenz Mitschang and Christian Freund

      Version of Record online: 30 APR 2009 | DOI: 10.1002/anie.200806149

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      Caged in: The formation of a complex between a peptide ligand and a major histocompatibility complex (MHC) class II protein is detected by a 129Xe biosensor. Cryptophane molecules that trap Xe atoms are modified with a hemagglutinin (HA) peptide, which binds to the MHC protein. The interaction can be monitored by an NMR chemical shift change of cage–HA bound 129Xe.

    4. Drug Nanocarriers

      Disterolphospholipids: Nonexchangeable Lipids and Their Application to Liposomal Drug Delivery (pages 4146–4149)

      Zhaohua Huang, Mahmoud Reza Jaafari and Francis C. Szoka Jr.

      Version of Record online: 7 MAY 2009 | DOI: 10.1002/anie.200900111

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      Extreme makeover of cholesterol: Cholesterol exchange is a major reason for the instability of liposomes in blood. The formation of a covalent hybrid between cholesterol and glycerophosphocholine preserves the bilayer-stabilizing effect of free cholesterol but prevents its transfer from the bilayer. Thus, disterolphospholipids (e.g. 1) are valuable new components for liposome formulation.

    5. Enzyme Models

      Structural Characterization and Remarkable Axial Ligand Effect on the Nucleophilic Reactivity of a Nonheme Manganese(III)–Peroxo Complex (pages 4150–4153)

      Jamespandi Annaraj, Jaeheung Cho, Yong-Min Lee, Sung Yeon Kim, Reza Latifi, Sam P. de Visser and Wonwoo Nam

      Version of Record online: 7 MAY 2009 | DOI: 10.1002/anie.200900118

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      The dark side of the Mn: A manganese(III) complex bearing a 13-membered macrocyclic ligand (1, see picture) binds a peroxo ligand in a side-on η2 fashion. The reactivity of 1 is influenced by the introduction of anionic ligands trans to the peroxo group. Electronic and structural changes upon trans-ligand binding explain the increased nucleophilicity of the resulting complexes 1-X.

    6. Protein Dynamics

      Protein Conformational Flexibility from Structure-Free Analysis of NMR Dipolar Couplings: Quantitative and Absolute Determination of Backbone Motion in Ubiquitin (pages 4154–4157)

      Loïc Salmon, Guillaume Bouvignies, Phineus Markwick, Nils Lakomek, Scott Showalter, Da-Wei Li, Korvin Walter, Christian Griesinger, Rafael Brüschweiler and Martin Blackledge

      Version of Record online: 4 MAY 2009 | DOI: 10.1002/anie.200900476

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      A robust procedure for the determination of protein-backbone motions on time scales of pico- to milliseconds directly from residual dipolar couplings has been developed that requires no additional scaling relative to external references. The results for ubiquitin (blue in graph: experimental N[BOND]HN order parameters) correspond closely to the amplitude, nature, and distribution of motion found in a 400 ns molecular-dynamics trajectory of ubiquitin (red).

    7. Asymmetric Catalysis

      Asymmetric Syntheses of l,l- and l,d-Di-myo-inositol-1,1′-phosphate and their Behavior as Stabilizers of Enzyme Activity at Extreme Temperatures (pages 4158–4161)

      Christina M. Longo, Yang Wei, Mary F. Roberts and Scott J. Miller

      Version of Record online: 7 MAY 2009 | DOI: 10.1002/anie.200900480

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      The big “DIP”per: The preparation of both l,l-DIP and l,d-DIP (see structures) involves a complex case of double asymmetric induction in the key step of the synthesis. The differential ability of each isomer to contribute to thermoprotection in the context of a key enzyme has been assessed and both isomers of DIP are shown to possess biological activity.

    8. Mass Spectrometry

      Matrix-Free Formation of Gas-Phase Biomolecular Ions by Soft Cluster-Induced Desorption (pages 4162–4165)

      Christoph. R. Gebhardt, Anna Tomsic, Hartmut Schröder, Michael Dürr and Karl L. Kompa

      Version of Record online: 12 MAR 2009 | DOI: 10.1002/anie.200804431

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      All in a ball: Neutral molecular clusters consisting of a few thousand molecules can be seen as tiny snow balls; if they are thrown fast enough onto a surface, they are able to pick up biomolecules such as insulin from that surface. Since they break down and evaporate during and after the collision, bare biomolecular ions are available for mass spectrometry after such an energetic throw.

    9. Photothermal Release

      An Efficient Method Based on the Photothermal Effect for the Release of Molecules from Metal Nanoparticle Surfaces (pages 4166–4169)

      Amir Bahman Samsam Bakhtiari, Dennis Hsiao, Guoxia Jin, Byron D. Gates and Neil R. Branda

      Version of Record online: 30 APR 2009 | DOI: 10.1002/anie.200805303

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      Please release me: The heat generated when metal nanoparticles absorb light results in a significant increase in the temperature of the environment around the particles and is used to selectively break bonds within a molecular system anchored to the nanoparticle surface (see picture). This process represents an advantageous and more universal method to deliver chemicals locally, while avoiding excessive tissue damage.

    10. Functional Nanobeacons

      Molecular Photoacoustic Tomography with Colloidal Nanobeacons (pages 4170–4173)

      Dipanjan Pan, Manojit Pramanik, Angana Senpan, Xinmai Yang, Kwang H. Song, Mike J. Scott, Huiying Zhang, Patrick J. Gaffney, Samuel A. Wickline, Lihong V. Wang and Gregory M. Lanza

      Version of Record online: 5 MAY 2009 | DOI: 10.1002/anie.200805947

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      Spotting clots: Vascularly constrained colloidal gold nanobeacons (GNBs; see picture) can be used as exogenous photoacoustic contrast agents for the targeted detection of fibrin, a major biochemical feature of thrombus. Fibrin-targeted GNBs provide a more than tenfold signal enhancement in photoacoustic tomography in the near-IR wavelength window, indicating their potential for diagnostic imaging.

    11. Bionanotechnology

      All-in-One Target-Cell-Specific Magnetic Nanoparticles for Simultaneous Molecular Imaging and siRNA Delivery (pages 4174–4179)

      Jae-Hyun Lee, Kyuri Lee, Seung Ho Moon, Yuhan Lee, Tae Gwan Park and Jinwoo Cheon

      Version of Record online: 30 APR 2009 | DOI: 10.1002/anie.200805998

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      Cancer-cell-targeted gene silencing was observed with a magnetic-nanoparticle platform (MEIO, magnetism-engineered iron oxide) on which a fluorescent dye, siRNA, and a RGD-peptide targeting moiety were attached (see picture). The different functionalities enable the macroscopic (magnetic resonance) and microscopic (fluorescence) imaging of target cells. This system may be suitable for concurrent diagnostic and therapeutic applications.

    12. Excited-State Structures

      Structural Tracking of a Bimolecular Reaction in Solution by Time-Resolved X-Ray Scattering (pages 4180–4184)

      Kristoffer Haldrup, Morten Christensen, Marco Cammarata, Qingyu Kong, Michael Wulff, Simon O. Mariager, Klaus Bechgaard, Robert Feidenhans'l, Niels Harrit and Martin M. Nielsen

      Version of Record online: 29 APR 2009 | DOI: 10.1002/anie.200900741

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      Molecular movies: Time-resolved X-ray scattering provides direct structural information on an electronically excited complex while it is formed in the bimolecular reaction between excited octahydrogen[tetrakis-μ-diphosphito-1κP:2κP′-diplatinate](4-) (PtPOP*) and thallium ions. In the exciplex one thallium(I) and two platinum(II) ions are found to be collinear.

    13. Supramolecular Chemistry

      Linear π-Acceptor-Templated Dynamic Clipping to Macrobicycles and [2]Rotaxanes (pages 4185–4189)

      Liana M. Klivansky, Gayane Koshkakaryan, Dennis Cao and Yi Liu

      Version of Record online: 30 APR 2009 | DOI: 10.1002/anie.200900716

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      Cage me! A linear dumbbell-shaped bipyridinium molecule can template cage formation around itself through sixfold imine bond formation to give an interlocked [2]rotaxane as the single product (see picture). This highly efficient [2+3] clipping occurs despite the symmetry mismatch between the template and the formed macrobicycle.

    14. Nanomechanics

      Understanding Covalent Mechanochemistry (pages 4190–4193)

      Jordi Ribas-Arino, Motoyuki Shiga and Dominik Marx

      Version of Record online: 29 APR 2009 | DOI: 10.1002/anie.200900673

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      The time is ripe: A general theoretical framework based on force-transformed potential energy surfaces rationalizes the intriguing results of recent experiments in the emerging field of covalent mechanochemistry.

    15. Organocatalysis

      N-Heterocyclic Carbenes as Efficient Organocatalysts for CO2 Fixation Reactions (pages 4194–4197)

      Yoshihito Kayaki, Masafumi Yamamoto and Takao Ikariya

      Version of Record online: 4 MAY 2009 | DOI: 10.1002/anie.200901399

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      Getting a fix: N-heterocyclic carbenes (NHCs) and NHC–CO2 adducts serve as potent organocatalysts for carbonate synthesis by the addition of a CO2 unit to propargylic alcohols or epoxides under mild and solvent-free reaction conditions (see scheme). The enhanced Lewis basicity of imidazol-2-ylidenes bearing electron-donating alkyl groups on the nitrogen atoms leads to utilizing CO2 as a nucleophilic fragment in the chemical fixation processes.

    16. Total Synthesis

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      Total Synthesis and Stereochemical Assignment of Micrococcin P1 (pages 4198–4201)

      David Lefranc and Marco A. Ciufolini

      Version of Record online: 30 APR 2009 | DOI: 10.1002/anie.200900621

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      Fifty years after the discovery of the thiopeptide antibiotic micrococcin P1, the constitutional and stereochemical uncertainties concerning its structure have been lifted with its total synthesis and absolute stereochemical assignment (see picture).

    17. Asymmetric Synthesis

      Stereocontrolled Synthesis of Highly Functionalized Quaternary Carbon Centers: A Route to α-Substituted Serines (pages 4202–4205)

      Xavier Ariza, Josep Cornellà, Mercè Font-Bardia, Jordi Garcia, Jordi Ortiz, Carolina Sánchez and Xavier Solans

      Version of Record online: 4 MAY 2009 | DOI: 10.1002/anie.200900609

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      Three in a row! Highly functionalized quaternary amino polyols with three consecutive asymmetric carbon centers have been prepared through tandem hydroboration of allene 1 and addition to an aldehyde (see scheme; Cy=cyclohexyl, TBDPS=tert-butyldiphenylsilyl, Ts=4-toluenesulfonyl). This one-pot process provides access to advanced intermediates for the enantioselective synthesis of α-substituted serines.

    18. Alcohol Oxidation

      Selectivity Control in Gold-Mediated Esterification of Methanol (pages 4206–4209)

      Bingjun Xu, Xiaoying Liu, Jan Haubrich, Robert J. Madix and Cynthia M. Friend

      Version of Record online: 6 FEB 2009 | DOI: 10.1002/anie.200805404

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      The Midas touch: The low-temperature transformation of methanol to methyl formate, formaldehyde, and formic acid is promoted by atomic oxygen adsorbed on metallic gold (see picture). The reactions occur with O-containing Au nanoparticles formed on Au(111) upon oxidation with ozone at 200 K; the facile esterification to methyl formate occurs well below room temperature.

    19. Surface Analysis

      Surprisingly Long-Range Surface-Enhanced Raman Scattering (SERS) on Au–Ni Multisegmented Nanowires (pages 4210–4212)

      Wei Wei, Shuzhou Li, Jill E. Millstone, Matthew J. Banholzer, Xiaodong Chen, Xiaoyang Xu, George C. Schatz and Chad A. Mirkin

      Version of Record online: 8 MAY 2009 | DOI: 10.1002/anie.200806116

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      Very long range surface-enhanced Raman scattering is observed from a nickel nanowire that is separated by 120 nm from a pair of gold nanodisks. The excitation of the surface-plasmon resonance (SPR) from the gold nanodisk pair generates an enhanced electromagnetic field near the nickel segment (SEM, left), leading to Raman intensity greater than the nickel alone (right).

    20. Nitroxyl Complexes

      Three Redox States of Nitrosyl: NO+, NO., and NO/HNO Interconvert Reversibly on the Same Pentacyanoferrate(II) Platform (pages 4213–4216)

      Andrea C. Montenegro, Valentín T. Amorebieta, Leonardo D. Slep, Diego F. Martín, Federico Roncaroli, Daniel H. Murgida, Sara E. Bari and José A. Olabe

      Version of Record online: 7 MAY 2009 | DOI: 10.1002/anie.200806229

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      Not so elusive: [FeII(CN)5(HNO)]3− has been characterized spectroscopically after the two-electron reduction of nitroprusside (see scheme). The complex is stable at pH 6, slowly decomposing to [Fe(CN)6]4− and N2O. It is deprotonated at increasing pH value with oxidation of bound NO to [FeII(CN)5(NO)]3−. [FeII(CN)5(HNO)]3− is the first non-heme iron–nitroxyl complex prepared in aqueous solution that is reversibly redox-active under biologically relevant conditions.

    21. Electrocatalysis

      Solution-Based Evolution and Enhanced Methanol Oxidation Activity of Monodisperse Platinum–Copper Nanocubes (pages 4217–4221)

      Dan Xu, Zhaoping Liu, Hongzhou Yang, Qingsheng Liu, Jun Zhang, Jiye Fang, Shouzhong Zou and Kai Sun

      Version of Record online: 29 APR 2009 | DOI: 10.1002/anie.200900293

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      Shape-controlled catalysis: High-quality Pt–Cu nanocubes with an average size of about 8 nm (see picture, scale bar=20 nm) were synthesized from a high-temperature organic solution system in the presence of various capping ligands. These cubic Pt–Cu nanocrystals terminated with {100} facets demonstrated a superior catalytic activity towards methanol oxidation compared to similar sized Pt–Cu and Pt nanospheres.

    22. Heterocycles

      Efficient and Economical Access to Substituted Benzothiazoles: Copper-Catalyzed Coupling of 2-Haloanilides with Metal Sulfides and Subsequent Condensation (pages 4222–4225)

      Dawei Ma, Siwei Xie, Peng Xue, Xiaojing Zhang, Jinhua Dong and Yongwen Jiang

      Version of Record online: 7 MAY 2009 | DOI: 10.1002/anie.200900486

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      Don′t tell azole: The first metal-catalyzed direct coupling of metal sulfides with aryl halides and subsequent intramolecular condensation provided substituted benzothiazoles (see scheme). A wide range of functional groups are tolerated under the reaction conditions.

    23. Organocatalysis

      Enantioselective Robinson-Type Annulation Reaction Catalyzed by Chiral Phosphoric Acids (pages 4226–4228)

      Takahiko Akiyama, Takuya Katoh and Keiji Mori

      Version of Record online: 29 APR 2009 | DOI: 10.1002/anie.200901127

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      Let′s resolve our differences: Implementation of an enantioselective Michael addition followed by an intramolecular aldol reaction catalyzed by two phosphoric acids has enabled the synthesis of cyclohexenone derivatives with excellent enantioselectivities. Prominent kinetic resolution was observed in the latter reaction. Ar=aromatic group, X=H, halogen, Y=H, Me, halogen.

    24. Tamiflu Synthesis

      Symmetry-Based Design for the Chemoenzymatic Synthesis of Oseltamivir (Tamiflu) from Ethyl Benzoate (pages 4229–4231)

      Bradford Sullivan, Ignacio Carrera, Melissa Drouin and Tomas Hudlicky

      Version of Record online: 7 MAY 2009 | DOI: 10.1002/anie.200901345

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      A short chemoenzymatic formal synthesis of oseltamivir from ethyl benzoate has been achieved. The key steps involve a toluene dioxygenase-mediated dihydroxylation, hetero-Diels–Alder cycloaddition, and generation of C4 acetamido functionality. The formal synthesis of oseltamivir is achieved in ten steps and incorporates a unique translocation of the olefin with concomitant elimination of the C2 hydroxy group (see scheme).

    25. Electron Transfer

      Electron Transfer in Peptides with Cysteine and Methionine as Relay Amino Acids (pages 4232–4234)

      Min Wang, Jian Gao, Pavel Müller and Bernd Giese

      Version of Record online: 7 MAY 2009 | DOI: 10.1002/anie.200900827

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      Caught on the hop: In multistep electron transfer (ET) reactions through peptides, aliphatic amino acids can also act as relay stations. With cysteine, the reaction occurs as a proton-coupled electron transfer (PCET) with water used as a mediator for the proton transfer (see picture).

    26. Synthetic Methods

      Stereoselective Palladium-Catalyzed Carboaminoxylations of Indoles with Arylboronic Acids and TEMPO (pages 4235–4238)

      Sylvia Kirchberg, Roland Fröhlich and Armido Studer

      Version of Record online: 4 MAY 2009 | DOI: 10.1002/anie.200901072

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      Indoles are not indolent: Various indoles react with arylboronic acids chemodivergently. C[BOND]H arylation of free indole and N-methylindole gives the corresponding C(2)-arylated indoles A whereas N-acylated, N-benzoylated, and N-Boc-protected indoles provide the corresponding arylcarboaminoxylated products B with excellent diastereoselectivity in good to excellent yields.

    27. Beryllium Ligands

      Complexes with Dative Bonds between d- and s-Block Metals: Synthesis and Structure of [(Cy3P)2Pt[BOND]Be(Cl)X] (X=Cl, Me) (pages 4239–4241)

      Holger Braunschweig, Katrin Gruss and Krzysztof Radacki

      Version of Record online: 4 MAY 2009 | DOI: 10.1002/anie.200900521

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      A platinum–beryllium adduct (see structure) was prepared by the reaction of [Pt(PCy3)2] and BeCl2. Treatment with methyllithium resulted in ligand substitution at the beryllium center. Both complexes were structurally characterized and display unprecedented two-center two-electron bonds between a transition metal and beryllium.

    28. Redoxactive Ligands

      An Odd-Electron Complex [Ruk(NOm)(Qn)(terpy)]2+ with Two Prototypical Non-Innocent Ligands (pages 4242–4245)

      Atanu Kumar Das, Biprajit Sarkar, Carole Duboc, Sabine Strobel, Jan Fiedler, Stanislav Záliš, Goutam Kumar Lahiri and Wolfgang Kaim

      Version of Record online: 8 MAY 2009 | DOI: 10.1002/anie.200900767

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      Six combinations of oxidation states are conceivable for the paramagnetic title complex. Single-crystal X-ray diffraction, spectroscopic analysis (IR, EPR at conventional and high frequency), and DFT calculations establish that it is the iminosemiquinone radical structure that is formed: [Ruk(NOm)(Qn)(terpy)]2+ (k=2+, m=1+, n=1−).

    29. Nitrogen Insertion

      End-On Nitrogen Insertion of a Diazo Compound into a Germanium(II) Hydrogen Bond and a Comparable Reaction with Diethyl Azodicarboxylate (pages 4246–4248)

      Anukul Jana, Sakya S. Sen, Herbert W. Roesky, Carola Schulzke, Sudipta Dutta and Swapan K. Pati

      Version of Record online: 7 MAY 2009 | DOI: 10.1002/anie.200900617

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      A happy ending: The germanium(II) hydride [LGeH], where L=[HC{(CMe)(2,6-iPr2C6H3N)}2], reacts with a diazoalkane to form the hydrazone derivative (see picture). The reaction proceeds through the unprecedented end-on nitrogen insertion of the diazo compound.

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    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
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