Angewandte Chemie International Edition

Cover image for Vol. 53 Issue 25

June 16, 2014

Volume 53, Issue 25

Pages 6279–6567

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Minireview
    11. Review
    12. Communications
    1. You have free access to this content
      Cover Picture: Organ Repair, Hemostasis, and In Vivo Bonding of Medical Devices by Aqueous Solutions of Nanoparticles (Angew. Chem. Int. Ed. 25/2014) (page 6279)

      Prof. Dr. Anne Meddahi-Pellé , Aurélie Legrand, Dr. Alba Marcellan , Liliane Louedec, Prof. Dr. Didier Letourneur and Prof. Dr. Ludwik Leibler

      Version of Record online: 6 MAY 2014 | DOI: 10.1002/anie.201404300

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      Rapid and efficient repair in vivo by the concept of nanobridging—adhesion by aqueous solutions of nanoparticles—even under hemorrhagic conditions in soft organs, such as the liver, for which sutures are traumatic, is described by D. Letourneur, L. Leibler et al. in their Communication on page 6369 ff. The method also leads to the remarkably aesthetic healing of deep skin wounds. Nanobridging also allows medical devices to be fixed to tissues, thereby opening new avenues for surgery and regenerative medicine.

    2. You have free access to this content
      Inside Cover: Polydopamine as a Biomimetic Electron Gate for Artificial Photosynthesis (Angew. Chem. Int. Ed. 25/2014) (page 6280)

      Dr. Jae Hong Kim, Minah Lee and Prof. Dr. Chan Beum Park

      Version of Record online: 28 APR 2014 | DOI: 10.1002/anie.201404170

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      The role of mussel-inspired polydopamine (PDA) as an electron gate and a versatile adhesive for mimicking natural photosynthesis is described in the Communication by C. B. Park and co-workers on page 6364 ff. The introduction of PDA as a charge separator significantly increased the rate of photochemical water oxidation by efficient and forward electron transfer. Furthermore, simple incorporation of a PDA ad-layer on the surface of conducting materials also facilitated fast charge separation and oxygen evolution.

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      Inside Back Cover: Accelerating Diffusion-Ordered NMR Spectroscopy by Joint Sparse Sampling of Diffusion and Time Dimensions (Angew. Chem. Int. Ed. 25/2014) (page 6569)

      Mateusz Urbańczyk, Prof. Dr. Wiktor Koźmiński and Dr. Krzysztof Kazimierczuk

      Version of Record online: 6 MAY 2014 | DOI: 10.1002/anie.201404172

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      Diffusion-ordered NMR spectroscopy is an effective method for the analysis of chemical mixtures. However, its resolution is often not sufficient for unambiguous spectral assignment. Multidimensional spectroscopy may enhance the resolution, but is rarely employed in diffusion-ordered NMR spectroscopy because of lengthy sampling of a signal. In their Communication on page 6464 ff., K. Kazimierczuk et al. show how the measurement can be accelerated by exploiting the principles of compressed sensing.

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      Back Cover: Flow-Through Synthesis on Teflon-Patterned Paper To Produce Peptide Arrays for Cell-Based Assays (Angew. Chem. Int. Ed. 25/2014) (page 6570)

      Dr. Frédérique Deiss, Wadim L. Matochko, Natasha Govindasamy, Edith Y. Lin and Dr. Ratmir Derda

      Version of Record online: 28 APR 2014 | DOI: 10.1002/anie.201404171

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      Teflon-patterned paper that can be used for multistep organic synthesis and then used in cell-based assays has been developed. In their Communication on page 6374 ff., R. Derda and co-workers describe the deposition of Teflon onto paper to create solvent-resistant barriers. The reagents confined by the pattern flow through the layer(s) of paper, thus permitting parallel flow-through syntheses of 96 peptides on one sheet of paper to produce arrays that can be used for cell-based assays.

  2. Frontispiece

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Minireview
    11. Review
    12. Communications
    1. You have free access to this content
      Frontispiece: Irreversible Denaturation of Proteins through Aluminum-Induced Formation of Backbone Ring Structures

      Prof. Dr. Bo Song, Dipl. Qian Sun, Dr. Haikuo Li, Dr. Baosheng Ge, Dr. Ji Sheng Pan, Prof. Dr. Andrew Thye Shen Wee, Dr. Yong Zhang, Dr. Shaohua Huang, Dr. Ruhong Zhou, Xingyu Gao, Prof. Dr. Fang Huang and Haiping Fang

      Version of Record online: 12 JUN 2014 | DOI: 10.1002/anie.201482571

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      B. Song, X. Gao, F. Huang et al. describe in their Communication on page 6358 ff. the ability of Al ions to induce the formation of backbone ring structures in a wide range of peptides, including neurodegenerative disease related motifs.

  3. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Minireview
    11. Review
    12. Communications
  4. Corrigendum

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Minireview
    11. Review
    12. Communications
    1. You have free access to this content
      Corrigendum: Intact P4 Tetrahedra as Terminal and Bridging Ligands in Neutral Complexes of Manganese (page 6296)

      M. Sc. Sebastian Heinl, Dr. Eugenia V. Peresypkina, Prof. Dr. Alexey Y. Timoshkin, Prof. Dr. Piero Mastrorilli, Dr. Vito Gallo and Prof. Dr. Manfred Scheer

      Version of Record online: 12 JUN 2014 | DOI: 10.1002/anie.201404981

      This article corrects:

      Intact P4 Tetrahedra as Terminal and Bridging Ligands in Neutral Complexes of Manganese1

      Vol. 52, Issue 41, 10887–10891, Version of Record online: 3 SEP 2013

  5. News

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Minireview
    11. Review
    12. Communications
  6. Author Profile

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Minireview
    11. Review
    12. Communications
    1. Joseph Wang (pages 6304–6305)

      Version of Record online: 24 FEB 2014 | DOI: 10.1002/anie.201400645

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      “My greatest achievement has been the success of my students and postdocs. The most exciting thing about my research is the ability to move to new topics and explore exciting frontiers …” This and more about Joseph Wang can be found on page 6304.

  7. News

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Minireview
    11. Review
    12. Communications
  8. Book Review

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Minireview
    11. Review
    12. Communications
    1. Electrons in Molecules. From Basic Principles to Molecular Electronics. By Jean-Pierre Launay and Michel Verdaguer. (page 6307)

      Robert Stadler

      Version of Record online: 12 JUN 2014 | DOI: 10.1002/anie.201403853

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      Oxford University Press, Oxford, 2013. 512 pp., hardcover, £ 55.00.—ISBN 978-0199297788

  9. Minireview

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Minireview
    11. Review
    12. Communications
    1. Carbonylation

      Carbonylations of Alkenes with CO Surrogates (pages 6310–6320)

      Lipeng Wu, Dr. Qiang Liu, Dr. Ralf Jackstell and Prof. Dr. Matthias Beller

      Version of Record online: 27 MAY 2014 | DOI: 10.1002/anie.201400793

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      All current industrial carbonylation processes rely on highly toxic and flammable carbon monoxide. Since these properties impede the wider use of carbonylation reactions in industry and academia, performing carbonylations with CO surrogates is highly desired and will contribute to further advances in sustainable chemistry. This Minireview summarizes the carbonylations of alkenes using different CO surrogates.

  10. Review

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Minireview
    11. Review
    12. Communications
    1. Covalent Monolayers

      Covalent Surface Modification of Oxide Surfaces (pages 6322–6356)

      Dr. Sidharam P. Pujari, Dr. Luc Scheres, Dr. Antonius T. M. Marcelis and Prof. Dr. Han Zuilhof

      Version of Record online: 21 MAY 2014 | DOI: 10.1002/anie.201306709

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      Not just scratching the surface: Covalently attached monolayers on oxide surfaces are reviewed with an eye to improved robustness, increased functionalization, understanding structural details, and the resulting potential for applications. Such monolayers, provided they are robust enough, provide a way of improving the properties of the bulk oxide material.

  11. Communications

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Minireview
    11. Review
    12. Communications
    1. Protein Structures

      Irreversible Denaturation of Proteins through Aluminum-Induced Formation of Backbone Ring Structures (pages 6358–6363)

      Prof. Dr. Bo Song, Dipl. Qian Sun, Dr. Haikuo Li, Dr. Baosheng Ge, Dr. Ji Sheng Pan, Prof. Dr. Andrew Thye Shen Wee, Dr. Yong Zhang, Dr. Shaohua Huang, Dr. Ruhong Zhou, Xingyu Gao, Prof. Dr. Fang Huang and Haiping Fang

      Version of Record online: 28 APR 2014 | DOI: 10.1002/anie.201307955

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      A good Al-rounder: Al ions can induce the formation of backbone ring structures in a wide range of peptides, including neurodegenerative disease related motifs. The rings are formed by the Al ion forming bonds simultaneously with the amide nitrogen and carbonyl oxygen atoms on the peptide backbone, which destabilizes the protein and results in irreversible denaturation.

    2. Biomimetic Materials

      Polydopamine as a Biomimetic Electron Gate for Artificial Photosynthesis (pages 6364–6368)

      Dr. Jae Hong Kim, Minah Lee and Prof. Dr. Chan Beum Park

      Version of Record online: 1 APR 2014 | DOI: 10.1002/anie.201402608

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      Nature as role model: Comparable to quinones that extract electrons from chlorophyll in the natural photosystem II, polydopamine (PDA) accelerates proton-coupled electron transfer and enables efficient charge separation of [Ru(bpy)3]2+. The introduction of PDA as an electron gate as well as a versatile adhesive significantly increases the efficiency of photochemical water oxidation.

    3. Organ Repair | Hot Paper

      You have full text access to this OnlineOpen article
      Organ Repair, Hemostasis, and In Vivo Bonding of Medical Devices by Aqueous Solutions of Nanoparticles (pages 6369–6373)

      Prof. Dr. Anne Meddahi-Pellé , Aurélie Legrand, Dr. Alba Marcellan , Liliane Louedec, Prof. Dr. Didier Letourneur and Prof. Dr. Ludwik Leibler

      Version of Record online: 16 APR 2014 | DOI: 10.1002/anie.201401043

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      Nanobridging is obtained by spreading a drop of aqueous nanoparticle solution on a wound edge and bringing edges into contact. In less than a minute, a strong closure and hemostasis can be achieved even within a wet and dynamic environment. Nanoparticle solutions can be also used to attach medical devices to organs.

    4. Solid-Phase Synthesis | Hot Paper

      Flow-Through Synthesis on Teflon-Patterned Paper To Produce Peptide Arrays for Cell-Based Assays (pages 6374–6377)

      Dr. Frédérique Deiss, Wadim L. Matochko, Natasha Govindasamy, Edith Y. Lin and Dr. Ratmir Derda

      Version of Record online: 11 APR 2014 | DOI: 10.1002/anie.201402037

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      On the same page: The patterned deposition of Teflon on paper creates barriers resistant to organic solvents. The solvents confined by the pattern flow through the paper at a controlled flow-rate, which permits the flow-through synthesis of 96 peptides in parallel on one sheet of paper. The resulting peptide arrays can be used to perform cell-based assays and discover 3D materials that support cell adhesion and growth.

    5. Organic Phosphorescence | Hot Paper

      Metal-Free Triplet Phosphors with High Emission Efficiency and High Tunability (pages 6378–6382)

      Michael Koch, Karthikeyan Perumal, Dr. Olivier Blacque, Dr. Jai Anand Garg, Dr. Ramanathan Saiganesh, Dr. Senthamaraikannan Kabilan, Prof. Dr. Kallupattu Kuppusamy Balasubramanian and Dr. Koushik Venkatesan

      Version of Record online: 12 MAY 2014 | DOI: 10.1002/anie.201402199

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      By taking advantage of the singlet fission process highly efficient phosphorescent emitters based on metal- and heavy atom-free boron compounds were synthesized. The combination of a suitable molecular scaffold and appropriate electronic properties of the substituents was utilized to tailor the phosphorescence emission properties in solution, neat solid, and in doped PMMA films.

    6. Asymmetric Catalysis

      Enantioselective Copper-Catalyzed Carboetherification of Unactivated Alkenes (pages 6383–6387)

      Michael T. Bovino, Timothy W. Liwosz, Nicole E. Kendel, Dr. Yan Miller, Dr. Nina Tyminska, Prof. Eva Zurek and Prof. Sherry R. Chemler

      Version of Record online: 5 MAY 2014 | DOI: 10.1002/anie.201402462

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      A general scheme: A highly enantioselective copper-catalyzed carboetherification of 4-pentenols has been developed. Both intramolecular (formal C[BOND]H functionalization) and intermolecular (net alkyl Heck-type coupling; see scheme) C[BOND]C bond formation can occur, thus forming a range of chiral functionalized tetrahydrofurans. DFT transition-state calculations provide a rationale for the observed asymmetric induction.

    7. Enzyme Models

      Highly Reactive Nonheme Iron(III) Iodosylarene Complexes in Alkane Hydroxylation and Sulfoxidation Reactions (pages 6388–6392)

      Dr. Seungwoo Hong, Dr. Bin Wang, Dr. Mi Sook Seo, Dr. Yong-Min Lee, Myoung Jin Kim, Prof. Dr. Hyung Rok Kim, Prof. Dr. Takashi Ogura, Dr. Ricardo Garcia-Serres, Dr. Martin Clémancey, Prof. Dr. Jean-Marc Latour and Prof. Dr. Wonwoo Nam

      Version of Record online: 12 MAY 2014 | DOI: 10.1002/anie.201402537

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      An iron boost: High-spin iron(III) iodosylarene complexes bearing an N-methylated cyclam ligand are prepared. The nonheme high-spin iron(III) iodosylarene intermediates are highly reactive oxidants capable of activating strong C[BOND]H bonds of alkanes. The electrophilic character of the iron(III) iodosylarene complexes is demonstrated in sulfoxidation reactions.

    8. Natural Products

      Total Synthesis of the Biphenyl Alkaloid (−)-Lythranidine (pages 6393–6396)

      M. Sc. Konrad Gebauer and Prof. Alois Fürstner

      Version of Record online: 12 MAY 2014 | DOI: 10.1002/anie.201402550

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      Triple: The distinguishing piperidine-metacyclophane framework of the Lythraceum alkaloid lythanidine was formed by ring-closing alkyne metathesis (RCAM) of a propargylic alcohol derivative followed by redox isomerization and a proton-catalyzed transannular aza-Michael addition as the key steps. This straightforward approach illustrates the enabling power of catalytic alkyne chemistry for target-oriented synthesis.

    9. Heterogeneous Catalysis | Hot Paper

      Design and Synthesis of Copper–Cobalt Catalysts for the Selective Conversion of Synthesis Gas to Ethanol and Higher Alcohols (pages 6397–6401)

      Dr. Gonzalo Prieto, Steven Beijer, Dr. Miranda L. Smith, Dr. Ming He, Yuen Au, Zi Wang, Prof. David A. Bruce, Prof. Krijn P. de Jong, Prof. James J. Spivey and Prof. Petra E. de Jongh

      Version of Record online: 14 MAY 2014 | DOI: 10.1002/anie.201402680

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      Coupling DFT simulations, microkinetic modeling and synthesis tools allowed the development of supported CuCo bimetallic nanoparticles as highly efficient catalysts for the selective conversion of synthesis gas (CO+H2) into ethanol and longer-chain alcohols. As predicted by theory, maximizing the contribution from mixed Cu–Co sites, while preventing Cu phase segregation, results in superior yields to high alcohols.

    10. Hyperfluorescence

      Luminous Butterflies: Efficient Exciton Harvesting by Benzophenone Derivatives for Full-Color Delayed Fluorescence OLEDs (pages 6402–6406)

      Sae Youn Lee, Prof. Dr. Takuma Yasuda, Dr. Yu Seok Yang, Dr. Qisheng Zhang and Prof. Dr. Chihaya Adachi

      Version of Record online: 18 MAY 2014 | DOI: 10.1002/anie.201402992

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      Lighting up: Butterfly-shaped benzophenone derivatives with small excited singlet–triplet energy gaps are demonstrated to exhibit efficient full-color delayed fluorescence. Organic light-emitting diodes employing these benzophenones as emitters can generate electroluminescence across most of the color gamut range, including white.

    11. Nanocarbide Catalysts

      Multiple Phases of Molybdenum Carbide as Electrocatalysts for the Hydrogen Evolution Reaction (pages 6407–6410)

      Cheng Wan, Yagya N. Regmi and Prof. Brian M. Leonard

      Version of Record online: 14 MAY 2014 | DOI: 10.1002/anie.201402998

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      Four phases of Mo-C, including γ-MoC which was stabilized for the first time as a nanomaterial, were synthesized and investigated for their catalytic activity and stability in the hydrogen evolution reaction (HER). X-ray photoelectron spectroscopy and valence band studies were also conducted for the first time on γ-MoC.

    12. Monodispersed Polymers

      Synthesis of Poly(ethylene oxide) Approaching Monodispersity (pages 6411–6413)

      Dr. Krzysztof Maranski, Dr. Yuri G. Andreev and Prof. Dr. Peter G. Bruce

      Version of Record online: 14 MAY 2014 | DOI: 10.1002/anie.201403436

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      Counting mers: Poly(ethylene oxide) (PEO) is one of the most widely used polymers, but polydispersity hinders establishing its structure–property relationships. A synthetic procedure that provides PEO with an unprecedented low level of dispersity is reported. In addition a mass spectrometric method is presented to measure such low dispersity.

    13. Metal Nanoparticles

      Highly Stable, Water-Dispersible Metal-Nanoparticle-Decorated Polymer Nanocapsules and Their Catalytic Applications (pages 6414–6418)

      Gyeongwon Yun, Dr. Zahid Hassan, Jiyeong Lee, Jeehong Kim, Dr. Nam-Suk Lee, Dr. Nam Hoon Kim, Dr. Kangkyun Baek, Dr. Ilha Hwang, Prof. Dr. Chan Gyung Park and Prof. Dr. Kimoon Kim

      Version of Record online: 19 MAY 2014 | DOI: 10.1002/anie.201403438

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      Desirable tailoring: Hollow polymer nanocapsules (PNs) made of cucurbit[6]uril (CB) serve as a versatile platform since various metal nanoparticles (NPs) can be introduced on the surface. They allow for a controlled synthesis, prevent self-aggregation, and provide high stability and dispersibility. Pd@CB-PNs show outstanding properties as heterogeneous catalysts in C[BOND]C and C[BOND]N bond-forming reactions in water.

    14. Biomimetic Synthesis | Hot Paper

      Spontaneous Biomimetic Formation of (±)-Dictazole B under Irradiation with Artificial Sunlight (pages 6419–6424)

      Adam Skiredj, Dr. Mehdi A. Beniddir, Prof. Dr. Delphine Joseph, Karine Leblanc, Dr. Guillaume Bernadat, Dr. Laurent Evanno and Prof. Dr. Erwan Poupon

      Version of Record online: 9 MAY 2014 | DOI: 10.1002/anie.201403454

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      Always the sun? Biosynthetic considerations guided the first total synthesis of dictazole B. Furthermore, insights into the biosynthetic pathway towards the aplysinopsin family were gained, and an easy access to challenging cyclobutane alkaloids of marine origin, which are often postulated to be biosynthetic precursors of more complex structures, was developed.

    15. Nanocrystal Growth

      Screw-Dislocation-Driven Bidirectional Spiral Growth of Bi2Se3 Nanoplates (pages 6425–6429)

      Awei Zhuang, Jia-Jun Li, You-Cheng Wang, Xin Wen, Yue Lin, Prof. Bin Xiang, Prof. Xiaoping Wang and Prof. Jie Zeng

      Version of Record online: 14 MAY 2014 | DOI: 10.1002/anie.201403530

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      Interesting faces with chiseled features: No longer limited to nanoribbons and smooth nanoplates, Bi2Se3 nanostructures in the form of spiral-type nanoplates with a bipyramid-like shape characterized by two sets of centrosymmetric helical fringes on the top and bottom faces were formed by a bidirectional growth process. Other evidence for the unique structure and growth mode include herringbone contours, spiral arms, and hollow cores (see picture).

    16. Nanostructures

      Synthesis, Characterization, and Properties of [4]Cyclo-2,7-pyrenylene: Effects of Cyclic Structure on the Electronic Properties of Pyrene Oligomers (pages 6430–6434)

      Takahiro Iwamoto, Dr. Eiichi Kayahara, Dr. Nobuhiro Yasuda, Prof. Dr. Toshiyasu Suzuki and Prof. Dr. Shigeru Yamago

      Version of Record online: 13 MAY 2014 | DOI: 10.1002/anie.201403624

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      Changing the landscape: A cyclic tetramer of pyrene, [4]cyclo-2,7-pyrenylene ([4]CPY), was synthesized by the platinum-mediated cyclotetramerization and subsequent dehydrogenation. DFT calculations and electrochemical analyses showed that the electronic structure of [4]CPY was completely altered from that of pyrene and linear oligopyrenes. The results clearly show there is modulation of the topology of molecular orbitals upon formation of a cyclic structure.

    17. Tandem Reactions

      Formation of Four Different Aromatic Scaffolds from Nitriles through Tandem Divergent Catalysis (pages 6435–6438)

      Dr. Ju Hyun Kim, Prof. Jean Bouffard and Prof. Sang-gi Lee

      Version of Record online: 20 MAY 2014 | DOI: 10.1002/anie.201403698

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      Four roads diverged: A zinc bromide complex, generated by the sequential reaction of nitriles with a Reformatsky reagent and 1-alkynes, is used as an intermediate for divergent palladium-catalyzed reactions. The reaction pathway depends on the choice of reaction solvents and palladium catalysts. The method provides a simple and efficient approach to four different frameworks starting from readily available nitriles.

    18. Asymmetric Catalysis

      Palladium-Catalyzed Decarboxylative Cycloaddition of Vinylethylene Carbonates with Formaldehyde: Enantioselective Construction of Tertiary Vinylglycols (pages 6439–6442)

      Ajmal Khan, Dr. Renfeng Zheng, Prof. Dr. Yuhe Kan, Jiang Ye, Juxiang Xing and Prof. Dr. Yong Jian Zhang

      Version of Record online: 14 MAY 2014 | DOI: 10.1002/anie.201403754

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      A Pd complex: An efficient method for the enantioselective construction of tertiary vinylglycols by the title reaction was developed. The palladium complex generated from [Pd2(dba)3]⋅CHCl3 and L catalyzes the cycloaddition under mild reaction conditions, thus converting racemic 1 into the corresponding 1,3-dioxolanes 2 in high yields with good to excellent enantioselectivities. dba=dibenzylideneacetone.

    19. Protein–Protein Interactions | Hot Paper

      A Natural-Product Switch for a Dynamic Protein Interface (pages 6443–6448)

      Marcel Scheepstra, Dr. Lidia Nieto, Dr. Anna K. H. Hirsch, Dr. Sascha Fuchs, Dr. Seppe Leysen, Chan Vinh Lam, Leslie in het Panhuis, Prof. Dr. Constant A. A. van Boeckel, Dr. Hans Wienk, Prof. Dr. Rolf Boelens, Dr. Christian Ottmann, Dr. Lech-Gustav Milroy and Prof. Dr. Luc Brunsveld

      Version of Record online: 12 MAY 2014 | DOI: 10.1002/anie.201403773

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      Rational splitting of the dual-binding properties of a natural product delivers two mechanistically different ligands, which selectively target opposite sides of a dynamic protein interface (see picture; AF2=activation function 2). This work highlights the value of screening natural products against transient protein complexes.

    20. Protein Labeling | Hot Paper

      Monitoring Endocytic Trafficking of Anthrax Lethal Factor by Precise and Quantitative Protein Labeling (pages 6449–6453)

      Siqi Zheng, Gong Zhang, Jie Li and Prof. Dr. Peng R. Chen

      Version of Record online: 14 MAY 2014 | DOI: 10.1002/anie.201403945

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      Visualizing toxin trafficking: Coupling the genetic-code expansion strategy with bioorthogonal reactions allowed site-specific fluorescent labeling of anthrax lethal factor (LF) with little perturbation to its native structure and function. Time-lapse visualization of the endocytic trafficking of a precisely labeled LF revealed molecular details underlying its virulence mechanism inside host cells. PA=protective antigen.

    21. Conductive Polymers

      Electrochemical Synthesis of a Microporous Conductive Polymer Based on a Metal–Organic Framework Thin Film (pages 6454–6458)

      Chunjing Lu, Prof. Dr. Teng Ben, Shixian Xu and Prof. Dr. Shilun Qiu

      Version of Record online: 22 MAY 2014 | DOI: 10.1002/anie.201402950

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      A 3D microporous conductive polymer has been achieved in the electrochemical synthesis of a porous polyaniline network with a MOF thin film. The prepared microporous polyaniline with well-defined uniform micropores of 0.84 nm exhibits a high BET surface area of 986 m2 g−1 and a high electric conductivity of 0.125 S cm−1 when doped with I2.

    22. Imaging Agents

      Catching Bubbles: Targeting Ultrasound Microbubbles Using Bioorthogonal Inverse-Electron-Demand Diels–Alder Reactions (pages 6459–6463)

      Aimen Zlitni, Nancy Janzen, Dr. F. Stuart Foster and Dr. John F. Valliant

      Version of Record online: 14 MAY 2014 | DOI: 10.1002/anie.201402473

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      Catching bubbles: Tetrazine-functionalized microbubbles were prepared for use as ultrasound contrast agents, and shown to selectively localize on cells labeled with a TCO-derivatized antibody against VEGFR2. This capture approach based on labeling and bioorthogonal chemistry was validated in a flow-chamber assay and in vivo through ultrasound imaging of VEGFR2-positive and VEGFR2-negative murine tumor models. TCO=trans-cyclooctene.

    23. Sparse Sampling Techniques

      Accelerating Diffusion-Ordered NMR Spectroscopy by Joint Sparse Sampling of Diffusion and Time Dimensions (pages 6464–6467)

      Mateusz Urbańczyk, Prof. Dr. Wiktor Koźmiński and Dr. Krzysztof Kazimierczuk

      Version of Record online: 24 APR 2014 | DOI: 10.1002/anie.201402049

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      Diffusion-ordered multidimensional NMR spectroscopy is a valuable technique for the analysis of complex mixtures, but the sampling of a multidimensional signal can be very time-consuming. Various sparse sampling techniques have been proposed to accelerate the measurement, but they have always been limited to frequency dimensions of NMR spectra. It is now revealed how sparse sampling can be extended to diffusion dimensions.

    24. Asymmetric Catalysis

      Highly Enantioselective Carbonyl–Ene Reactions of 2,3-Diketoesters: Efficient and Atom-Economical Process to Functionalized Chiral α-Hydroxy-β-Ketoesters (pages 6468–6472)

      Phong M. Truong, Dr. Peter Y. Zavalij and Prof. Michael P. Doyle

      Version of Record online: 20 MAY 2014 | DOI: 10.1002/anie.201402233

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      Outside the box: Carbonyl–ene reactions of 2,3-diketoesters, catalyzed by [Cu{(S,S)-tBu-box}](SbF6)2 [box=bis(oxazoline)], generate chiral α-functionalized α-hydroxy-β-ketoesters in up to 94 % yield and 97 % ee. The 2,3-diketoesters are conveniently accessed from the corresponding α-diazo-β-ketoester, and a catalyst loading as low as 1.0 mol % can be used.

    25. Phase-Transfer Catalysis

      Mild Copper-Catalyzed Fluorination of Alkyl Triflates with Potassium Fluoride (pages 6473–6476)

      Hester Dang, Melrose Mailig and Prof. Gojko Lalic

      Version of Record online: 18 MAY 2014 | DOI: 10.1002/anie.201402238

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      Teacher′s PET: The title reaction delivers excellent yields of the desired alkyl fluorides by using potassium fluoride as a fluoride source in the presence of the copper catalyst [IPrCuOTf]. This procedure is potentially suited for the preparation of 18F-labeled PET probes. IPr=1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, Tf=trifluoromethanesulfonyl.

    26. Photocatalysis

      Towards a Practical Development of Light-Driven Acceptorless Alkane Dehydrogenation (pages 6477–6481)

      Dr. Abhishek Dutta Chowdhury, Dr. Nico Weding, Dr. Jennifer Julis, Prof. Dr. Robert Franke, Dr. Ralf Jackstell and Prof. Dr. Matthias Beller

      Version of Record online: 14 MAY 2014 | DOI: 10.1002/anie.201402287

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      Blue (light) is green: The efficient light-induced atom-economical alkane dehydrogenation of various linear and cyclic alkanes (including shale gas constituents and liquid organic hydrogen carriers) was accomplished using trans-[Rh(PMe3)2(CO)Cl] as a catalyst in the presence of a specific nitrogenous additive. It provides a benign alternative to the direct use of alkanes as olefin feedstocks.

    27. Carbene Chemistry

      Skeleton Decoration of NHCs by Amino Groups and its Sequential Booster Effect on the Palladium-Catalyzed Buchwald–Hartwig Amination (pages 6482–6486)

      Yin Zhang, Dr. Vincent César, Golo Storch, Dr. Noël Lugan and Dr. Guy Lavigne

      Version of Record online: 6 MAY 2014 | DOI: 10.1002/anie.201402301

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      Boosting the PEPPSI: A sequential enhancement of the activity of the PEPPSI NHC-based palladium pre-catalyst in the Buchwald–Hartwig amination was obtained by a rational modification of its standard N-heterocyclic carbene (IMes or IPr), consisting of a “simple” incorporation of one, and then two, dimethylamino groups as substituents. These results highlight the valuable benefits of NHC-skeleton decoration in C–N cross-coupling.

    28. Bioinspired Catalysts

      Arginine-Containing Ligands Enhance H2 Oxidation Catalyst Performance (pages 6487–6491)

      Dr. Arnab Dutta, Dr. John A. S. Roberts and Dr. Wendy J. Shaw

      Version of Record online: 12 MAY 2014 | DOI: 10.1002/anie.201402304

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      Learning from nature: An amino acid-based outer coordination sphere results in the homogeneous [Ni(PCy2NArg2)]8+ complex that can electrochemically oxidize H2 in water with a turnover frequency of 210 s−1 at acidic pH. The outer coordination sphere improves the H2 addition and H+ movement from the active center.

    29. O2-Promoted C[BOND]H Activation

      Oxygen-Promoted C[BOND]H Bond Activation at Palladium (pages 6492–6495)

      Dr. Margaret L. Scheuermann, David W. Boyce, Prof. Kyle A. Grice, Prof. Werner Kaminsky, Prof. Stefan Stoll, Prof. William B. Tolman, Prof. Ole Swang and Prof. Karen I. Goldberg

      Version of Record online: 9 MAY 2014 | DOI: 10.1002/anie.201402484

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      Oxygen leads the way: [Pd(P(Ar)(tBu)2)2] (Ar=naphthyl) undergoes a reaction with molecular oxygen in which C[BOND]H and O[BOND]O bonds are cleaved. Observation of the reaction at low temperature suggests the initial formation of a superoxo complex, which then generates a peroxo complex prior to the C[BOND]H activation step. The transition state for an energetically viable C[BOND]H activation across a Pd[BOND]peroxo bond was located computationally.

    30. Carbon Nanomaterials

      Facile One-Pot, One-Step Synthesis of a Carbon Nanoarchitecture for an Advanced Multifunctonal Electrocatalyst (pages 6496–6500)

      Dr. Zhenhai Wen, Dr. Suqin Ci, Dr. Yang Hou and Prof. Junhong Chen

      Version of Record online: 5 MAY 2014 | DOI: 10.1002/anie.201402574

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      Not ones to laze about on the lawn, nitrogen-doped graphene/carbon-nanotube (CNT) hybrids showed high electrocatalytic activity for a series of important electrochemical reactions as a result of nitrogen doping and their unique structure with the graphene nanosheets entrapped in the inner void of the CNTs. The hybrids were prepared by a facile low-cost method from solid-phase sources with high efficiency.

    31. Peptide Bond Cleavage

      Serine-Selective Aerobic Cleavage of Peptides and a Protein Using a Water-Soluble Copper–Organoradical Conjugate (pages 6501–6505)

      Yohei Seki, Dr. Kana Tanabe, Dr. Daisuke Sasaki, Dr. Youhei Sohma, Dr. Kounosuke Oisaki and Prof. Dr. Motomu Kanai

      Version of Record online: 14 MAY 2014 | DOI: 10.1002/anie.201402618

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      Peptides and proteins can be cleaved selectively at serine residues under mild (room temperature, near neutral pH value) aerobic conditions by a water-soluble copper–organoradical conjugate. The method is applicable to the site-selective cleavage of polypeptides that possess various functional groups, D-amino acids, or sensitive disulfide pairs. The system was also used for the site-selective cleavage of a native protein comprising more than 70 amino acid residues.

    32. Heterocycles | Hot Paper

      Access to Oxoquinoline Heterocycles by N-Heterocyclic Carbene Catalyzed Ester Activation for Selective Reaction with an Enone (pages 6506–6510)

      Dr. Zhenqian Fu, Dr. Ke Jiang, Dr. Tingshun Zhu, Prof. Dr. Jaume Torres and Prof. Dr. Yonggui Robin Chi

      Version of Record online: 18 MAY 2014 | DOI: 10.1002/anie.201402620

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      Under construction: A single-step enantioselective access to multicyclic oxoquinoline-type heterocycles is possible. The process takes advantage of the unique reaction patterns of esters under N-heterocyclic carbene (NHC) catalysis. It involves activation of the β-carbon atom of an ester as the key step with a subsequent chemoselective cascade reaction with amino enone substrates. Ts=4-toluenesulfonyl.

    33. Asymmetric Catalysis

      Palladium-Catalyzed Asymmetric Amination of Allenyl Phosphates: Enantioselective Synthesis of Allenes with an Additional Unsaturated Unit (pages 6511–6514)

      Qiankun Li, Prof. Dr. Chunling Fu and Prof. Dr. Shengming Ma

      Version of Record online: 2 MAY 2014 | DOI: 10.1002/anie.201402647

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      Chiral 2,3-allenyl amines with or without (an) additional C[BOND]C double or triple bond(s) can be prepared through asymmetric Pd-catalyzed amination of allenyl phosphates. Under the optimized conditions, which involve the use of (R)-3,4,5-(MeO)3-MeOBIPHEP as the ligand and the reaction being performed at 0 °C, the products were obtained with up to 90 % yield and 88–94 % ee.

    34. Biocatalysis

      Enzyme-Catalyzed Oxidation of 5-Hydroxymethylfurfural to Furan-2,5-dicarboxylic Acid (pages 6515–6518)

      Willem P. Dijkman, Daphne E. Groothuis and Prof. Dr. Marco W. Fraaije

      Version of Record online: 6 MAY 2014 | DOI: 10.1002/anie.201402904

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      A fourpeat: The recently discovered 5-hydroxymethylfurfural oxidase (HMFO) was found to perform a quadruple oxidation of [5-(hydroxymethyl)furan-2-yl]methanol (see scheme). The biocatalyst can also be used to convert 5-hydroxymethylfurfural into furan-2,5-dicarboxylic acid, thus providing a biobased platform chemical for the production of polymers. The oxidase acts on alcohol groups only and therefore depends on the hydration of aldehyde groups.

    35. Macrolide Synthesis | Very Important Paper

      Synthesis of Tetrahydropyran/Tetrahydrofuran-Containing Macrolides by Palladium-Catalyzed Alkoxycarbonylative Macrolactonizations (pages 6519–6522)

      Yu Bai, Dexter C. Davis and Prof. Dr. Mingji Dai

      Version of Record online: 13 MAY 2014 | DOI: 10.1002/anie.201403006

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      CO for bridged macrolides: An efficient Pd-catalyzed cascade alkoxycarbonylative macrolactonization to synthesize various THP/THF-containing macrolactones in one step from relatively simple alkendiols is possible. Challenging macrolactones involving tertiary alcohols were synthesized smoothly as well. The method was applied to the synthesis of the potent anticancer compound 9-demethylneopeltolide.

    36. C[BOND]H Activation

      You have full text access to this OnlineOpen article
      Iridium-Catalyzed Arylative Cyclization of Alkynones by 1,4-Iridium Migration (pages 6523–6527)

      Dr. Benjamin M. Partridge, Jorge Solana González and Prof. Hon Wai Lam

      Version of Record online: 19 MAY 2014 | DOI: 10.1002/anie.201403271

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      Migrating to iridium: Iridium catalysis enables the arylative cyclization of alkynones with arylboronic acids to give complex polycycles with high stereoselectivities. These reactions involve the first reported examples of 1,4-iridium migration.

    37. C[BOND]C Bond Cleavage | Hot Paper

      Copper-Catalyzed Aerobic Oxidative C[BOND]C Bond Cleavage for C[BOND]N Bond Formation: From Ketones to Amides (pages 6528–6532)

      Conghui Tang and Dr. Ning Jiao

      Version of Record online: 14 MAY 2014 | DOI: 10.1002/anie.201403528

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      A copper-catalyzed aerobic oxidative C(CO)[BOND]C(alkyl) bond cleavage of aryl alkyl ketones for C[BOND]N bond formation proceeds with high chemoselectivity. A series of acetophenone derivatives as well as more challenging aryl ketones with long-chain alkyl groups could be cleaved efficiently to give the corresponding amides, which are frequently found in biologically active compounds and pharmaceuticals.

    38. Total Synthesis | Hot Paper

      Total Synthesis and Stereochemical Reassignment of Mandelalide A (pages 6533–6537)

      Honghui Lei, Jialei Yan, Jie Yu, Dr. Yuqing Liu, Zhuo Wang, Prof. Zhengshuang Xu and Prof. Tao Ye

      Version of Record online: 18 MAY 2014 | DOI: 10.1002/anie.201403542

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      Structural revision: A revised configurational assignment for the marine macrolide mandelalide A is proposed and validated by total synthesis. This study is one of several recent examples in a growing list of investigations that correct misassigned structures of natural products by stereocontrolled total synthesis.

    39. P Dication

      The Highly Lewis Acidic Dicationic Phosphonium Salt: [(SIMes)PFPh2][B(C6F5)4]2 (pages 6538–6541)

      Dr. Michael H. Holthausen, Meera Mehta and Prof. Dr. Douglas W. Stephan

      Version of Record online: 14 MAY 2014 | DOI: 10.1002/anie.201403693

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      Versatile phosphonium salt: The dication [(SIMes)PFPh2][B(C6F5)4]2 is prepared by oxidation of an NHC-derived cationic phosphine followed by fluoride abstraction. This species exhibits remarkable Lewis acidity in stoichiometric reactions as well as in Lewis acid catalysis of hydrodefluorination of fluoroalkanes and the hydrosilylation of olefins and acetylenes.

    40. Heterocycle Synthesis

      Furan-Based o-Quinodimethanes by Gold-Catalyzed Dehydrogenative Heterocyclization of 2-(1-Alkynyl)-2-alken-1-ones: A Modular Entry to 2,3-Furan-Fused Carbocycles (pages 6542–6545)

      Liejin Zhou, Mingrui Zhang, Dr. Wenbo Li and Prof. Dr. Junliang Zhang

      Version of Record online: 18 MAY 2014 | DOI: 10.1002/anie.201403709

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      Caught in a trap: A novel strategy for in situ generation of furan-based ortho-quinodimethanes (o-QDMs) using the title reaction was developed. These furan-based o-QDMs were trapped by electron-deficient olefins and alkynes, thus leading to various 2,3-furan-fused carbocycles in good yields with high diastereo- and regioselectivities. EWG=electron-withdrawing group.

    41. Small Ring Systems

      Silylative Cyclopropanation of Allyl Phosphates with Silylboronates (pages 6546–6549)

      Dr. Ryo Shintani, Ryuhei Fujie, Dr. Momotaro Takeda and Prof. Dr. Kyoko Nozaki

      Version of Record online: 13 MAY 2014 | DOI: 10.1002/anie.201403726

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      β attack! A potassium-bis(trimethylsilyl)amide-mediated cyclopropanation of allyl phosphates with silylboronates has been developed. Unlike the reported copper-catalyzed allylic substitution reactions, the nucleophile selectively attacks at the β-position of the allylic substrates under the present conditions. The reaction mechanism has also been investigated, thus indicating the involvement of a silylpotassium species as the active nucleophilic component.

    42. Dimerization

      Cross-Coupling Reactions between Stable Carbenes (pages 6550–6553)

      Cory M. Weinstein, Dr. Caleb D. Martin, Liu Liu and Prof. Guy Bertrand

      Version of Record online: 18 MAY 2014 | DOI: 10.1002/anie.201404199

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      A couple of carbenes: By utilizing stable carbenes with low-lying LUMOs, coupling with the stable nucleophilic diaminocyclopropenylidene was achieved. This coupling resulted in the formation of two new and rare examples of a bent allene as well as the isolation of the first carbene–carbene heterodimer. Dipp=2,6-iPr2C6H3, Mes=2,4,6-Me3C6H2.

    43. Oxygen Activation

      Superoxide Formation on Isolated Cationic Gold Clusters (pages 6554–6557)

      Alex P. Woodham and Dr. André Fielicke

      Version of Record online: 21 MAY 2014 | DOI: 10.1002/anie.201402783

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      Act(ivat)ing positively: Cationic gold clusters are found to react with molecular oxygen and activate it by forming a superoxide (O2), as confirmed by vibrational spectroscopy. This process is spontaneous in clusters, which attain a closed shell within the spherical jellium model, whereas other cluster sizes exhibit a self-promoting effect whereby the presence of multiple oxygen ligands is required for activation.

    44. Tandem Catalysis | Hot Paper

      Tandem Organocatalysis and Photocatalysis: An Anthraquinone-Catalyzed Indole-C3-Alkylation/Photooxidation/1,2-Shift Sequence (pages 6558–6562)

      Dipl.-Chem. Stephanie Lerch, B. Sc. Lisa-Natascha Unkel and Juniorprof. Dr. Malte Brasholz

      Version of Record online: 21 MAY 2014 | DOI: 10.1002/anie.201402920

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      Orthogonal reactivities: Anthraquinone derivatives catalyze the thermal C3- alkylation of indoles with benzylamines in sequence with a visible-light-driven photooxidation/1,2-shift reaction to provide new fluorescent 2,2-disubstituted indoline-3-one derivatives. Quinones function as H2 shuttles in the indole C3-alkylation with amines and the subsequent photooxidation of the intermediate 3-arylmethyl-1H-indoles is remarkably selective.

    45. Heteroporphyrins

      Core-Modified Rubyrins Containing Dithienylethene Moieties (pages 6563–6567)

      Zhikuan Zhou, Dr. Yi Chang, Dr. Soji Shimizu, Dr. John Mack, Christian Schütt, Prof. Rainer Herges, Prof. Zhen Shen and Prof. Nagao Kobayashi

      Version of Record online: 29 APR 2014 | DOI: 10.1002/anie.201402711

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      Tuning aromaticity: Two stable core-modified rubyrins bearing one (1) and two (2) dithienylethene (DTE) units have been synthesized. Compound 1, with a “closed-form” DTE unit, has a cyclic conjugated system with 26 π-electrons. In contrast, macrocycle 2 containing one “open-form” DTE unit has nonaromatic properties.

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