Angewandte Chemie International Edition

Cover image for Vol. 48 Issue 52

December 21, 2009

Volume 48, Issue 52

Pages 9757–9987

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Review
    12. Communications
    13. Preview
    1. Cover Picture: Templated Ligand Environments for the Selective Incorporation of Different Metals into DNA (Angew. Chem. Int. Ed. 52/2009) (page 9757)

      Hua Yang, Andrzej Z. Rys, Christopher K. McLaughlin and Hanadi F. Sleiman

      Article first published online: 27 NOV 2009 | DOI: 10.1002/anie.200905811

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      DNA can template the formation of different ligand environments that are selective for their binding metals. H. F. Sleiman and co-workers describe in their Communication on page 9919 ff. how placement of a metal in the incorrect DNA-templated environment results in the occurrence of “error-checking”: the metal can spontaneously adjust its redox state, displace another labile metal to form a more-stable complex, or reorganize the coordination site to create a more-favored complex.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Review
    12. Communications
    13. Preview
    1. Inside Cover: Surface Passivation and Transfer Doping of Silicon Nanowires (Angew. Chem. Int. Ed. 52/2009) (page 9758)

      Chun-Sheng Guo, Lin-Bao Luo, Guo-Dong Yuan, Xiao-Bao Yang, Rui-Qin Zhang, Wen-Jun Zhang and Shuit-Tong Lee

      Article first published online: 27 NOV 2009 | DOI: 10.1002/anie.200906383

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      The large surface-to-volume ratio of nanomaterials could facilitate efficient doping using purely surface passivation and adsorption. In their Communication on page 9896 ff., R. Q. Zhang, S. T. Lee, and co-workers describe surface passivation and transfer doping in silicon nanowires (SiNWs, see picture) by surface termination with hydrogen atoms and adsorption of ammonia molecules. The approach is an alternative to conventional volume doping to modulate the conductivity of SiNWs or other nanomaterials.

  3. Graphical Abstract

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Review
    12. Communications
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    1. Graphical Abstract: Angew. Chem. Int. Ed. 52/2009 (pages 9761–9773)

      Article first published online: 15 DEC 2009 | DOI: 10.1002/anie.200990256

  4. Corrigenda

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Review
    12. Communications
    13. Preview
    1. You have free access to this content
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      Snapshots of the Al[BOND]Al σ-Bond Formation Starting from {AlR2} Units: Experimental and Computational Observations (page 9773)

      Patrick Henke, Tobias Pankewitz, Wim Klopper, Frank Breher and Hansgeorg Schnöckel

      Article first published online: 15 DEC 2009 | DOI: 10.1002/anie.200990260

      This article corrects:

      Snapshots of the Al[BOND]Al σ-Bond Formation Starting from {AlR2} Units: Experimental and Computational Observations1

      Vol. 48, Issue 43, 8141–8145, Article first published online: 25 AUG 2009

  5. News

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Review
    12. Communications
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    1. Masaki Shimizu (page 9778)

      Article first published online: 24 NOV 2009 | DOI: 10.1002/anie.200905814

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      “The biggest challenge facing scientists is the highly effective use of solar energy. If I could be anyone for a day, I would be Michael Jordan …” This and more about Masaki Shimizu can be found on page 9778.

  7. News

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
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    8. News
    9. Book Review
    10. Highlights
    11. Review
    12. Communications
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    1. Handbook of Ring-Opening Polymerization. Edited by Philippe Dubois, Olivier Coulembier and Jean-Marie Raquez. (page 9780)

      Laurent Fontaine

      Article first published online: 15 DEC 2009 | DOI: 10.1002/anie.200904840

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      Wiley-VCH, Weinheim 2009. 408 pp., hardcover € 149.00.—ISBN 978-3527319534

  9. Highlights

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

      Linear Energy Relations and the Computational Design of Selective Hydrogenation/Dehydrogenation Catalysts (pages 9782–9784)

      Thomas Bligaard

      Article first published online: 24 NOV 2009 | DOI: 10.1002/anie.200905141

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      Mind over matter: Electronic structure calculations have been used to establish linear energy relations for chemical reactions on solid surfaces which aid in the design of new catalytic materials. Newly discovered accurate linear relations for the hydrogenation of organic molecules on transition metals suggest that the computational design of selective hydrogenation catalysts for complex reactions may soon be feasible.

    2. Catalysis with Light

      Photoredox Catalysis with Visible Light (pages 9785–9789)

      Kirsten Zeitler

      Article first published online: 27 NOV 2009 | DOI: 10.1002/anie.200904056

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      On the sunny side: Recent examples of visible-light-promoted photoredox catalysis in the presence of [Ru(bpy)3]2+ as an efficient photocatalyst have set new standards for conducting challenging reactions under mild and environmentally benign conditions.

  10. Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Author Profile
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    9. Book Review
    10. Highlights
    11. Review
    12. Communications
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    1. C[BOND]H Functionalization

      Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C[BOND]H Bond Cleavage (pages 9792–9826)

      Lutz Ackermann, Rubén Vicente and Anant R. Kapdi

      Article first published online: 8 DEC 2009 | DOI: 10.1002/anie.200902996

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      Cutting across: Direct arylations are increasingly viable alternatives to conventional cross-coupling reactions with stoichiometric amounts of organometallic reagents (see Scheme). This Review summarizes recent progress in the rapidly evolving research area of transition-metal-catalyzed C[BOND]H bond-cleavage reactions for (hetero)aryl syntheses.

  11. Communications

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

      Direct Assessment of Electron Delocalization Using NMR Chemical Shifts (pages 9828–9833)

      Stephan N. Steinmann, Daniel F. Jana, Judy I.-C. Wu, Paul von R. Schleyer, Yirong Mo and Clémence Corminboeuf

      Article first published online: 30 NOV 2009 | DOI: 10.1002/anie.200905390

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      Probe it: The new BLW-IGLO approach evaluates the magnetic responses of molecules in which conjugative interactions are “disabled” (see picture, red bonds). The NMR spectroscopy parameters of the localized structures provide ideal non-aromatic olefinic hydrogen δ(1H) references for the fully conjugated systems.

    2. Asymmetric Catalysis

      Asymmetric Organocatalytic Relay Cascades: Catalyst-Controlled Stereoisomer Selection in the Synthesis of Functionalized Cyclohexanes (pages 9834–9838)

      Yao Wang, Rong-Gang Han, Yong-Long Zhao, Shu Yang, Peng-Fei Xu and Darren J. Dixon

      Article first published online: 27 NOV 2009 | DOI: 10.1002/anie.200905014

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      Passing the baton: A relay cascade process provides cyclohexanes in a direct, efficient, and stereoselective manner. The triple-cascade reaction is efficient, affords high selectivities, and has a broad scope, and different diastereomers are readily accessible by judicious choice of organocatalysts.

    3. CO2 Reduction

      Non-Metal-Mediated Homogeneous Hydrogenation of CO2 to CH3OH (pages 9839–9843)

      Andrew E. Ashley, Amber L. Thompson and Dermot O'Hare

      Article first published online: 24 NOV 2009 | DOI: 10.1002/anie.200905466

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      Turning a problem to advantage: CO2, a contributor to global warming, was converted into the valuable resource CH3OH by adding it to 2,2,6,6-tetramethylpiperidine and B(C6F5)3 in toluene under H2 (1–2 atm), heating the mixture at 160 °C, and vacuum distillation. CH3OH was formed via the complex shown (C blue, N purple, O red, B orange, F green) as the sole C1 product.

    4. Main-Group Chemistry

      Abnormal Reactivity of an N-Heterocyclic Carbene (NHC) with a Phosphaalkene: A Route to a 4-Phosphino-Substituted NHC (pages 9844–9847)

      Joshua I. Bates, Pierre Kennepohl and Derek P. Gates

      Article first published online: 24 NOV 2009 | DOI: 10.1002/anie.200905401

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      A naughty NHC: A stable N-heterocyclic carbene (NHC) reacts with a phosphaalkene not at the expected 2-position, but through the 4-position, which leads to an unprecedented 4-phosphino-substituted NHC that functions as a novel bifunctional ligand for gold(I). The mechanism of this reaction has been investigated using density functional calculations.

    5. Organocatalysis

      anti-Selective Asymmetric Michael Reactions of Aldehydes and Nitroolefins Catalyzed by a Primary Amine/Thiourea (pages 9848–9852)

      Hisatoshi Uehara and Carlos F. Barbas III

      Article first published online: 26 NOV 2009 | DOI: 10.1002/anie.200905313

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      It′s finally here: Highly anti-selective Michael reactions of a functionalized aldehyde with nitroolefins have been realized using a primary amine/thiourea catalyst (see scheme; TBS=tert-butyldimethylsilyl). The reaction relies on a conformational strategy based on directing the formation of a Z-configured enamine intermediate.

    6. Cyclobutadiene Hopping

      Photo–Thermal Haptotropism in Cyclopentadienylcobalt Complexes of Linear Phenylenes: Intercyclobutadiene Metal Migration (pages 9853–9857)

      Thomas A. Albright, Peter I. Dosa, Tom N. Grossmann, Victor N. Khrustalev, Oluwakemi A. Oloba, Robin Padilla, Renaud Paubelle, Amnon Stanger, Tatiana V. Timofeeva and K. Peter C. Vollhardt

      Article first published online: 26 NOV 2009 | DOI: 10.1002/anie.200905088

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      The CpCo-shuffle: {CpCo} complexes of linear [3]- and [5]phenylene undergo a light-induced haptotropic migration from a more strongly bound cyclobutadiene moiety to a less strongly bound (see scheme). The shift is thermally reversible and proceeds along the periphery of the intervening arene rings. As such, the systems constitute photo–thermal storage systems, as well the first examples of cyclobutadiene-to-cyclobutadiene haptotropism.

    7. Fluorinated Alkenes

      Highly Stereoselective Synthesis of Monofluoroalkenes from α-Fluorosulfoximines and Nitrones (pages 9858–9861)

      Wei Zhang, Weizhou Huang and Jinbo Hu

      Article first published online: 24 NOV 2009 | DOI: 10.1002/anie.200905077

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      A fine fusion: α-fluorosulfoximines readily react with simple nitrones to give monofluoroalkenes with excellent E/Z stereocontrol (see scheme). This novel fluoroolefination method shows promising applications in medicinal chemistry as monofluoroalkenes are potential mimetics for peptide units as protein inhibitors.

    8. Immunoassay

      Phospholipid-Coated Carbon Nanotubes as Sensitive Electrochemical Labels with Controlled-Assembly-Mediated Signal Transduction for Magnetic Separation Immunoassay (pages 9862–9866)

      Huagui Nie, Sijia Liu, Ruqin Yu and Jianhui Jiang

      Article first published online: 24 NOV 2009 | DOI: 10.1002/anie.200903503

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      A coat to note: An electrochemical immunoassay strategy is developed using phospholipid-coated multiwalled carbon nanotubes (MWNTs) as the electrochemical labels (see scheme; PSA=antigen protein; MB=magnetic bead). This strategy affords great sensitivity and specificity in signal transduction.

    9. Drug Delivery

      Externally Triggered Glass Transition Switch for Localized On-Demand Drug Delivery (pages 9867–9870)

      Jos T. F. Keurentjes, Maartje F. Kemmere, Henny Bruinewoud, Micky A. M. E. Vertommen, Stefan A. Rovers, Richard Hoogenboom, Léon F. S. Stemkens, Fabiènne L. A. M. A. Péters, Naomi J. C. Tielen, Dirk T. A. van Asseldonk, Anne F. Gabriel, Elbert A. Joosten and Marco A. E. Marcus

      Article first published online: 26 NOV 2009 | DOI: 10.1002/anie.200904172

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      I want a new drug dose: External on-demand laser triggering is used in a drug-delivery concept, with on/off ratios in excess of 1000/1. The switching mechanism involves the glass transition of hydrophobic polymers with a large change in diffusivity. Formation of a glassy surface layer of the implant in the off state plays a key role, resulting in negligible off-release. (Picture: data points indicate ibuprofen concentration).

    10. Polymerization

      Metalloorganic Polymerization Catalysis as a Tool To Probe Crystallization Properties of Polymers: The Case of Isotactic Poly(1-butene) (pages 9871–9874)

      Claudio De Rosa, Finizia Auriemma and Luigi Resconi

      Article first published online: 26 NOV 2009 | DOI: 10.1002/anie.200904300

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      Age shall not weary them: Stereodefective isotactic polybutene samples, synthesized with single-center metallocene catalysts, crystallize from the melt into the stable form I (see picture) and do not undergo phase transformation upon aging at room temperature. Hence, the corresponding physical and mechanical properties of molded objects are not altered by aging.

    11. Asymmetric Catalysis

      Intramolecular Alkynylcyclopropanation of Olefins Catalyzed by Bi(OTf)3: Stereoselective Synthesis of 1-Alkynyl-3-azabicyclo[3.1.0]hexanes (pages 9875–9878)

      Kimihiro Komeyama, Natsuko Saigo, Motoyoshi Miyagi and Ken Takaki

      Article first published online: 26 NOV 2009 | DOI: 10.1002/anie.200904610

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      The postman always rings twice: 1-Alkynyl-3-azabicyclo[3.1.0]hexanes 2 were obtained in good to excellent yields from the stereoselective Bi(OTf)3-catalyzed dehydrative alkynylcyclopropanation of azaenynols 1, in which the propargyl alcohol motif of 1 acted as a propargyl carbene synthetic equivalent.

    12. Click Chemistry

      Analysis and Optimization of Copper-Catalyzed Azide–Alkyne Cycloaddition for Bioconjugation (pages 9879–9883)

      Vu Hong, Stanislav I. Presolski, Celia Ma and M. G. Finn

      Article first published online: 26 NOV 2009 | DOI: 10.1002/anie.200905087

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      How to click with biomolecules: Copper-catalyzed azide–alkyne cycloaddition has been optimized for use with biological molecules. The key development is the addition of two reagents that allow ascorbate to be used as reducing agent whilst eliminating problems caused by copper ascorbate side reactions. The result is a robust, rapid, and convenient procedure for the modification of proteins, DNA, RNA, and other biomolecules (see scheme).

    13. Zeolites

      Diversification of RTH-Type Zeolite and Its Catalytic Application (pages 9884–9887)

      Toshiyuki Yokoi, Masato Yoshioka, Hiroyuki Imai and Takashi Tatsumi

      Article first published online: 24 NOV 2009 | DOI: 10.1002/anie.200905214

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      The RTH-type zeolite (see picture) has an attractive pore structure, but its compositional variation is limited. Now, metallosilicates with the RTH-topology can be synthesized by two routes, one of which does not use structure-directing agents. Thus prepared Al-containing RTH-type zeolites exhibited a remarkable catalytic performance for the methanol-to-olefins reaction, producing propene with high selectivity.

    14. Amine Synthesis

      Efficient Catalytic Synthesis of Tertiary and Secondary Amines from Alcohols and Urea (pages 9888–9891)

      Jinling He, Jung Won Kim, Kazuya Yamaguchi and Noritaka Mizuno

      Article first published online: 26 NOV 2009 | DOI: 10.1002/anie.200905385

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      Urea as a nitrogen source: The supported ruthenium hydroxide, Ru(OH)x/TiO2, acts as an efficient heterogeneous catalyst for the title reaction. The retrieved catalyst after the reaction could be reused without a significant loss of its catalytic performance.

    15. σ-Acceptor Ligands

      Gold–Silane and Gold–Stannane Complexes: Saturated Molecules as σ-Acceptor Ligands (pages 9892–9895)

      Pauline Gualco, Tzu-Pin Lin, Marie Sircoglou, Maxime Mercy, Sonia Ladeira, Ghenwa Bouhadir, Lisa M. Pérez, Abderrahmane Amgoune, Laurent Maron, François P. Gabbaï and Didier Bourissou

      Article first published online: 24 NOV 2009 | DOI: 10.1002/anie.200905391

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      Gold gets a grip: Spectroscopic, structural, and computational results provide evidence for unprecedented Au[RIGHTWARDS ARROW]Si and Au[RIGHTWARDS ARROW]Sn interactions in gold(I) complexes derived from diphosphino-substituted silane and stannane ligands (see scheme).

    16. Passivation Doping

      Surface Passivation and Transfer Doping of Silicon Nanowires (pages 9896–9900)

      Chun-Sheng Guo, Lin-Bao Luo, Guo-Dong Yuan, Xiao-Bao Yang, Rui-Qin Zhang, Wen-Jun Zhang and Shuit-Tong Lee

      Article first published online: 8 DEC 2009 | DOI: 10.1002/anie.200904890

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      Staying on top: Altering the surface of silicon nanowires (SiNWs) by terminating the surface with different species and/or introducing surface adsorbates can change the electrical properties of the SiNWs. Such easy, nondestructive conductivity modification would expand possible applications of SiNWs.

    17. Coordination Polymers

      Iodinated Nanoscale Coordination Polymers as Potential Contrast Agents for Computed Tomography (pages 9901–9904)

      Kathryn E. deKrafft, Zhigang Xie, Guohua Cao, Sylvie Tran, Liqing Ma, Otto Z. Zhou and Wenbin Lin

      Article first published online: 24 NOV 2009 | DOI: 10.1002/anie.200904958

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      Nanoscale coordination polymers (NCPs), prepared with metal ions and an iodinated ligand, were synthesized using reverse-phase microemulsion techniques and rapid precipitation procedures. The NCPs carry high payloads of iodine (ca. 63 wt %) and have potential applications as a new class of contrast agents for computed tomography (CT), as demonstrated by phantom studies (see figure).

    18. Metal–Organic Frameworks

      Freeze Drying Significantly Increases Permanent Porosity and Hydrogen Uptake in 4,4-Connected Metal–Organic Frameworks (pages 9905–9908)

      Liqing Ma, Athena Jin, Zhigang Xie and Wenbin Lin

      Article first published online: 20 NOV 2009 | DOI: 10.1002/anie.200904983

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      Freeze the flood: After replacing high boiling-point solvents inside the channels of a metal–organic framework (MOF), benzene is frozen and then removed under vacuum by sublimation. Bypassing the liquid phase eliminates the detrimental effects of surface tension that induce mesopore collapse in MOFs, thereby enhancing their permanent porosity and hydrogen-uptake capacity (see scheme).

    19. Nanostructures

      Photoresponsive Supramolecular Organometallic Nanosheets Induced by PtII⋅⋅⋅PtII and C[BOND]H⋅⋅⋅π Interactions (pages 9909–9913)

      Yong Chen, Kai Li, Wei Lu, Stephen Sin-Yin Chui, Chun-Wah Ma and Chi-Ming Che

      Article first published online: 20 NOV 2009 | DOI: 10.1002/anie.200905678

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      It's a flat world: Charge-neutral pincer-type cyclometalated platinum(II) aryl acetylides can be assembled into quasi-two-dimensional nanosheets through bilateral intermolecular noncovalent interactions (see picture). These nanosheets can be further self-organized into layered materials on a flat substrate and exhibit NIR phosphorescence and light-modulated conductivity.

    20. Drug Delivery

      Reversibly Stabilized Multifunctional Dextran Nanoparticles Efficiently Deliver Doxorubicin into the Nuclei of Cancer Cells (pages 9914–9918)

      Yu-Ling Li, Li Zhu, Zhaozhong Liu, Ru Cheng, Fenghua Meng, Jing-Hao Cui, Shun-Jun Ji and Zhiyuan Zhong

      Article first published online: 24 NOV 2009 | DOI: 10.1002/anie.200904260

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      Getting in there: Efficient intracellular delivery of anticancer drugs is achieved by using reversibly cross-linked dextran nanoparticles, which are rapidly destabilized under reductive environments that mimic those of the intracellular compartments. These nanoparticles show high drug loading efficiency and reduction-triggered release of doxorubicin in vitro as well as inside tumor cells, particularly to the cell nucleus (see scheme).

    21. Metal–DNA Structures

      Templated Ligand Environments for the Selective Incorporation of Different Metals into DNA (pages 9919–9923)

      Hua Yang, Andrzej Z. Rys, Christopher K. McLaughlin and Hanadi F. Sleiman

      Article first published online: 18 NOV 2009 | DOI: 10.1002/anie.200904186

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      Each to his own: DNA templates the formation of bis(terpyridine), bis(phenanthroline), and terpyridine:phenanthroline ligand environments, which strongly bind FeII, CuI, and CuII (see picture), respectively, to generate highly stable metal–DNA complexes. When a metal is placed in the “incorrect” environment, it can spontaneously adjust its redox state, be displaced by another metal, or reorganize the coordination site to create a more favored complex.

    22. Photothermal Effect

      Probing the Photothermal Effect of Gold-Based Nanocages with Surface-Enhanced Raman Scattering (SERS) (pages 9924–9927)

      Matthew Rycenga, Zhipeng Wang, Eric Gordon, Claire M. Cobley, Andrea G. Schwartz, Cynthia S. Lo and Younan Xia

      Article first published online: 15 DEC 2009 | DOI: 10.1002/anie.200904382

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      A spectral thermometer: The conformation of molecules on a metallic nanoparticle's surface is sensitive to temperature variations and can be easily monitored in situ by surface-enhanced Raman scattering (SERS). Excitation of the metallic nanoparticle for SERS can concurrently induce a photothermal effect whereby the light absorbed by the nanoparticle is released as heat. From the SERS spectra, the changes in temperature during the photothermal effect can be derived (see picture).

    23. Magnetism

      A Calix[4]arene 3d/4f Magnetic Cooler (pages 9928–9931)

      Georgios Karotsis, Marco Evangelisti, Scott J. Dalgarno and Euan K. Brechin

      Article first published online: 24 NOV 2009 | DOI: 10.1002/anie.200905012

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      Chilling out: The first 3d/4f cluster based on calix[4]arenes (see picture; purple Mn, brown Gd, red O, blue N) has a high magnetic isotropy and a large number of molecular spin states that are populated even at low temperatures, whereas its ferromagnetic limit is approached only at high applied fields. These results enable the complex to be an excellent magnetic refrigerant for low-temperature applications.

    24. Localized SERS

      Direct Evidence of High Spatial Localization of Hot Spots in Surface-Enhanced Raman Scattering (pages 9932–9935)

      Chang Chen, James Andell Hutchison, Francesca Clemente, Ronald Kox, Hiroshi Uji-I, Johan Hofkens, Liesbet Lagae, Guido Maes, Gustaaf Borghs and Pol Van Dorpe

      Article first published online: 20 NOV 2009 | DOI: 10.1002/anie.200905389

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      Hot and cold: The high degree of localization in SERS hot spots is demonstrated directly by a selective deposition of Raman analytes inside and outside the field-enhanced regions in a plasmonic cavity (see picture). The localization is demonstrated by measurements of both the absolute SERS intensities and the kinetics for photoinduced degradation at different positions.

    25. Conjugated Oligomers

      Pentiptycene-Derived Oligo(p-phenyleneethynylene)s: Conformational Control, Chain-Length Effects, Localization of Excitation, and Intrachain Resonance Energy Transfer (pages 9936–9939)

      Jye-Shane Yang, Jyu-Lun Yan, Cheng-Kai Lin, Chih-Yuan Chen, Zhen-Yu Xie and Chung-Hsuan Chen

      Article first published online: 26 NOV 2009 | DOI: 10.1002/anie.200905405

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      Do the twist: The preference of large pentiptycene–pentiptycene dihedral angles and the restricted torsional relaxation for pentiptycene-derived oligo (p-phenyleneethynylene)s in a 2-methyltetrahydrofuran glass at 80 K result in a localized excited state. These results demonstrate not only the concept of torsion-induced localization of excitation but also the efficient intrachain energy hopping processes in conjugated polymers.

    26. Total Synthesis (1)

      Total Synthesis of Spirastrellolide F Methyl Ester—Part 1: Strategic Considerations and Revised Approach to the Southern Hemisphere (pages 9940–9945)

      Gregory W. O'Neil, Julien Ceccon, Stefan Benson, Marie-Pierre Collin, Bernhard Fasching and Alois Fürstner

      Article first published online: 8 DEC 2009 | DOI: 10.1002/anie.200906121

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      In readiness for closure: To ensure optimal convergence in the projected total synthesis of spirastrellolide F, the building block representing the southern hemisphere was prepared with a free carboxylic acid and an enol triflate (Tf) terminus (see picture). This unusual pattern allows the 38-membered macrocyclic core of this potent antimitotic agent to be constructed, while keeping late-stage protecting-group manipulations to a minimum.

    27. Total Synthesis (2)

      Total Synthesis of Spirastrellolide F Methyl Ester—Part 2: Macrocyclization and Completion of the Synthesis (pages 9946–9950)

      Stefan Benson, Marie-Pierre Collin, Gregory W. O'Neil, Julien Ceccon, Bernhard Fasching, Michaël D. B. Fenster, Cédrickx Godbout, Karin Radkowski, Richard Goddard and Alois Fürstner

      Article first published online: 8 DEC 2009 | DOI: 10.1002/anie.200906122

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      Marvel of the sea: A concise and highly convergent total synthesis of the methyl ester of the marine macrolide spirastrellolide F (see picture), which has exquisite antimitotic properties, is reported. In this approach, the northern and the southern hemispheres of this intricate target are stitched together in only two consecutive steps (Suzuki coupling, Yamaguchi lactonization) without any interim protecting-group manipulations.

    28. Conductive Organic Crystals

      Phosphonated Hexaphenylbenzene: A Crystalline Proton Conductor (pages 9951–9953)

      Lucía Jiménez-García, Anke Kaltbeitzel, Wojciech Pisula, Jochen S. Gutmann, Markus Klapper and Klaus Müllen

      Article first published online: 26 NOV 2009 | DOI: 10.1002/anie.200902116

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      Well stacked: Organic crystals of small molecules constitute an alternative to common polymeric electrolytes (Nafion 117) and inorganic crystals that are employed as proton exchange membranes in fuel cell systems. A phosphonic acid containing hexaphenylbenzene forms a columnar supramolecular array and exhibits a high and constant intrinsic conductivity of 3.2×10−3 S cm−1 from 120 to 180 °C under 1 bar H2O atmosphere (see picture).

    29. Porous Materials

      A Mesoporous Metal–Organic Framework (pages 9954–9957)

      Nicole Klein, Irena Senkovska, Kristina Gedrich, Ulrich Stoeck, Antje Henschel, Uwe Mueller and Stefan Kaskel

      Article first published online: 24 NOV 2009 | DOI: 10.1002/anie.200904599

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      MOF for more gas storage: A new mesoporous metal–organic framework (MOF) with extremely high adsorption capacities for methane, H2, and n-butane is prepared from the reaction of H3(btb), H2(2,6-ndc), and zinc nitrate (btb=benzene-1,3,5-tribenzoate; 2,6ndc=2,6-naphthalenedicarboxylate). The main structural motif is a dodecahedron formed from 12 Zn4O6+ clusters, four 2,6-ndc, and eight btb linkers (see picture; green: Zn4O6+, gray: C, red: O; the red sphere illustrates the pore volume).

    30. Organolithium Compounds

      A Dilithium 1,4-Butanediide with a Chlorine-Centered Li12 Icosahedral Structure (pages 9958–9961)

      Reinald Fischer, Helmar Görls and Matthias Westerhausen

      Article first published online: 24 NOV 2009 | DOI: 10.1002/anie.200904793

      Thumbnail image of graphical abstract

      Larger lithium clusters than tetrahedral and octahedral Lin aggregates can be prepared as cage structures with a central anion. The central chlorine atom (green) serves as a template for the formation of a Li12 icosahedral cage (orange), which is stabilized by 1,4-butanediide “clamps” (C gray).

    31. Hydrogen Generation

      Light-Driven Hydrogen Generation: Efficient Iron-Based Water Reduction Catalysts (pages 9962–9965)

      Felix Gärtner, Basker Sundararaju, Annette-Enrica Surkus, Albert Boddien, Björn Loges, Henrik Junge, Pierre H. Dixneuf and Matthias Beller

      Article first published online: 20 NOV 2009 | DOI: 10.1002/anie.200905115

      Thumbnail image of graphical abstract

      Let your light shine: A novel state-of-the-art system for light-driven proton reduction with iron catalysts was developed (see scheme; SR=sacrificial reagent). It consists of simple iron carbonyl complexes such as [Fe3(CO)12], triethylamine as sacrificial reagent (electron donor), and [Ir(bpy)(ppy)2]PF6 as photosensitizer (PS). High turnover numbers of more than 3000 for the sensitizer and 400 for the iron catalyst are obtained.

    32. Molecular Wires

      Single Molecular Wires Connecting Metallic and Insulating Surface Areas (pages 9966–9970)

      Christian Bombis, Francisco Ample, Leif Lafferentz, Hao Yu, Stefan Hecht, Christian Joachim and Leonhard Grill

      Article first published online: 30 NOV 2009 | DOI: 10.1002/anie.200904645

      Thumbnail image of graphical abstract

      Totally wired: A particular molecular adsorption geometry can be prepared by adsorbing single conjugated polyfluorene chains partially on a clean Au(111) surface and partially on a thin crystalline NaCl film, thus connecting metallic and insulating surface areas. This configuration allows the electronic characterization of one and the same molecular wire as a function of its atomic-scale environment in a planar configuration.

    33. Annulenes

      Is the [9]Annulene Cation a Möbius Annulene? (pages 9971–9974)

      Götz Bucher, Stefan Grimme, Robert Huenerbein, Alexander A. Auer, Eva Mucke, Felix Köhler, Jan Siegwarth and Rainer Herges

      Article first published online: 24 NOV 2009 | DOI: 10.1002/anie.200900886

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      Does it do the twist? High-level theoretical calculations show that the [9]annulene cation exists in two isomers: a twisted 4n electron Möbius aromatic compound, and a non-twisted boat-like Hückel conformation (see scheme). The latter form was detected by laser flash photolysis experiments; an example of a stable, charged, or uncharged parent Möbius annulene is still elusive.

    34. Organocatalysis

      A Catalytic Asymmetric 6 π Electrocyclization: Enantioselective Synthesis of 2-Pyrazolines (pages 9975–9978)

      Steffen Müller and Benjamin List

      Article first published online: 26 NOV 2009 | DOI: 10.1002/anie.200905035

      Thumbnail image of graphical abstract

      A closer look at α,β-unsaturated hydrazonium ions reveals that they are isoelectronic to the pentadienyl anion, making them suitable substrates to undergo 6π electrocyclizations. The enantioselective catalysis of this transformation is achieved for the first time by asymmetric Brønsted acid catalysis.

    35. Catalytic Asymmetric 6π Electrocyclization: Enantioselective Synthesis of Functionalized Indolines (pages 9979–9982)

      Eleanor E. Maciver, Sam Thompson and Martin D. Smith

      Article first published online: 4 NOV 2009 | DOI: 10.1002/anie.200905169

      Thumbnail image of graphical abstract

      How to close a ring: An approach to catalytic asymmetric 6π electrocyclization leads to a highly enantioselective process that was used in the synthesis of chiral indolines (see scheme). Treatment of N-aryl imines under phase transfer conditions in the presence of N-benzyl cinchonidinium chloride generates a delocalized 2-aza-pentadienyl anion system that cyclizes in up to 99 % yield and 98 % ee.

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      Article first published online: 15 DEC 2009 | DOI: 10.1002/anie.200990259

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