Angewandte Chemie International Edition

Cover image for Vol. 54 Issue 14

Early View (Online Version of Record published before inclusion in an issue)

Editor: Peter Gölitz, Deputy Editors: Neville Compton, Haymo Ross

Online ISSN: 1521-3773

Associated Title(s): Angewandte Chemie, Chemistry - A European Journal, Chemistry – An Asian Journal, ChemistryOpen, ChemPlusChem, Zeitschrift für Chemie

  1. Communications

    1. Carbon Dots | Hot Paper

      Red, Green, and Blue Luminescence by Carbon Dots: Full-Color Emission Tuning and Multicolor Cellular Imaging

      Kai Jiang, Shan Sun, Dr. Ling Zhang, Yue Lu, Prof. Aiguo Wu, Prof. Congzhong Cai and Prof. Hengwei Lin

      Article first published online: 31 MAR 2015 | DOI: 10.1002/anie.201501193

      Thumbnail image of graphical abstract

      On the dot: A facile approach to photoluminescent carbon dots (CDs) that can be excited by a single wavelength and demonstrate emission of the three primary colors (red, green, and blue) is reported. The resulting CDs can be potentially used in the fabrication of flexible full-color emission films and in multicolor cellular imaging.

    2. Mesoporous Materials

      Highly Ordered Mesoporous Few-Layer Graphene Frameworks Enabled by Fe3O4 Nanocrystal Superlattices

      Yucong Jiao, Dandan Han, Limin Liu, Li Ji, Guannan Guo, Prof. Jianhua Hu, Prof. Dong Yang and Prof. Angang Dong

      Article first published online: 31 MAR 2015 | DOI: 10.1002/anie.201501398

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      Framed: The title frameworks were fabricated from self-assembled Fe3O4 nanocrystal superlattices. Because of their unique architectures and superior structure durability, the mesoporous graphene frameworks exhibit excellent electrochemical performance when used as anode materials for lithium-ion batteries.

    3. Sensors | Hot Paper

      Next-Generation Sequencing as Input for Chemometrics in Differential Sensing Routines

      Sara Goodwin, Alexandra M. Gade, Michelle Byrom, Baine Herrera, Camille Spears, Dr. Eric V. Anslyn and Dr. Andrew D. Ellington

      Article first published online: 31 MAR 2015 | DOI: 10.1002/anie.201501822

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      Keeping score: Nucleic acid sequences and sequence counts were used as multivariate data without the necessity of a spatial array. Aptamers were used as semi-specific receptors for cell line differentiation, and cross-reactivity between the aptamers was observed. The principal component analysis (PCA) generates high-dimensionality score plots, thus differentiating a mixture of complex and subtly different analytes.

    4. EPR Spectroscopy

      Distance Measurement on an Endogenous Membrane Transporter in E. coli Cells and Native Membranes Using EPR Spectroscopy

      Dr. Benesh Joseph, Arthur Sikora, Prof. Dr. Enrica Bordignon, Prof. Dr. Gunnar Jeschke, Prof. Dr. David S. Cafiso and Prof. Dr. Thomas F. Prisner

      Article first published online: 31 MAR 2015 | DOI: 10.1002/anie.201501086

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      A novel general strategy was used for precise distance measurements on an outer membrane protein in whole E. coli cells and isolated outer membranes. This approach provides an elegant way to study conformational changes or protein–protein/ligand interactions under native conditions and provides a method to validate high-resolution structures of membrane proteins in their native environment.

  2. Highlights

    1. Azidation

      Cyclic Hypervalent Iodine Reagents and Iron Catalysts: The Winning Team for Late-Stage C[BOND]H Azidation

      Maria Victoria Vita and Prof. Dr. Jerome Waser

      Article first published online: 30 MAR 2015 | DOI: 10.1002/anie.201501666

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      1+1=3: By combining the exceptional reactivities of cyclic hypervalent iodine reagents and iron catalysts, Sharma and Hartwig achieved the azidation of C[BOND]H bonds with unprecedented efficiency and selectivity. The late-stage introduction of azides into complex bioactive molecules will greatly facilitate the synthesis of analogues and accelerate the discovery of new chemical entities.

  3. Communications

    1. Polymers

      Self-Immolative Poly(4,5-dichlorophthalaldehyde) and its Applications in Multi-Stimuli-Responsive Macroscopic Plastics

      Anthony M. DiLauro, Gregory G. Lewis and Prof. Scott T. Phillips

      Article first published online: 30 MAR 2015 | DOI: 10.1002/anie.201501320

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      Selective laser sintering has been used to prepare synthetic materials from a new type of self-immolative polymer. These materials autonomously amplify macroscopic and nonlocalized changes in the material in response to specific molecular inputs, and alter the response of the material depending on the identity of an applied signal.

    2. Metallacycles

      Stabilizing Two Classical Antiaromatic Frameworks: Demonstration of Photoacoustic Imaging and the Photothermal Effect in Metalla-aromatics

      Dr. Congqing Zhu, Yuhui Yang, Ming Luo, Caixia Yang, Jingjing Wu, Lina Chen, Prof. Dr. Gang Liu, Prof. Dr. Tingbin Wen, Dr. Jun Zhu and Prof. Dr. Haiping Xia

      Article first published online: 30 MAR 2015 | DOI: 10.1002/anie.201501349

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      Two birds with one stone: Two classical antiaromatic molecules, cyclobutadiene and pentalene, were stabilized by introducing one metal fragment by a [2+2] cycloaddition reaction of osmapentalyne with alkynes. These metalla-aromatic molecules absorb broadly from the UV to the near-IR region and show significant photoacoustic and photothermal effects.

    3. Total Synthesis

      Synthesis of Each Enantiomer of Rocaglamide by Means of a Palladium(0)-Catalyzed Nazarov-Type Cyclization

      Zhe Zhou and Prof. Dr. Marcus A. Tius

      Article first published online: 30 MAR 2015 | DOI: 10.1002/anie.201501374

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      Start to finish: A recently reported Pd0-catalyzed asymmetric Nazarov-type cyclization was applied in the key step of the first catalytic asymmetric total synthesis of (−)-rocaglamide (natural) and (+)-rocaglamide. The stereochemistry at the C3 position controls the stereochemistry of all other stereocenters and is determined in the cyclization step. dba=dibenzylidene acetone.

    4. Electrocatalysis

      Phosphorus-Modified Tungsten Nitride/Reduced Graphene Oxide as a High-Performance, Non-Noble-Metal Electrocatalyst for the Hydrogen Evolution Reaction

      Dr. Haijing Yan, Prof. Chungui Tian, Dr. Lei Wang, Dr. Aiping Wu, Meichen Meng, Lu Zhao and Prof. Honggang Fu

      Article first published online: 30 MAR 2015 | DOI: 10.1002/anie.201501419

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      Boosting HER activity by phosphorus modification of tungsten nitride/reduced graphene oxide leads to a low-cost, high-performance, non-noble metal electrocatalyst for the hydrogen evolution reaction. The catalyst has a very small onset overpotential, a low Tafel slope, a large exchange current density in acid, and was stable in accelerated durability testing.

    5. Energetic Materials

      The Many Faces of FOX-7: A Precursor to High-Performance Energetic Materials

      Prof. Dr. Haixiang Gao and Prof. Dr. Jean'ne M. Shreeve

      Article first published online: 30 MAR 2015 | DOI: 10.1002/anie.201501973

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      Fox in a box: New derivatives created from 1-diamino-2, 2-dinitroethene (FOX-7) often have properties superior to those of RDX. The compounds exhibit good thermal stability, high density, positive heats of formation, an acceptable oxygen balance, and excellent detonation properties. These findings contribute to the value of FOX-7 as an energetic precursor.

    6. Asymmetric Synthesis

      Stereoselective Synthesis of the Halaven C14–C26 Fragment from D-Quinic Acid: Crystallization-Induced Diastereoselective Transformation of an α-Methyl Nitrile

      Francis Belanger, Dr. Charles E. Chase, Dr. Atsushi Endo, Dr. Francis G. Fang, Dr. Jing Li, Steven R. Mathieu, Dr. Annie Z. Wilcoxen and Huiming Zhang

      Article first published online: 30 MAR 2015 | DOI: 10.1002/anie.201501143

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      Crystallization-induced diastereoselective transformation of an α-methyl nitrile completes an entirely non-chromatographic synthesis of the halichondrin B C14–C26 stereochemical array. All four stereogenic centers in the Halaven C14–C26 fragment were assembled on a crystalline polycyclic template derived from the single chiral source D-quinic acid.

    7. Biosensors

      Electrochemical Assay to Detect Influenza Viruses and Measure Drug Susceptibility

      Xiaohu Zhang, Dr. Abasaheb N. Dhawane, Joyce Sweeney, Dr. Yun He, Dr. Mugdha Vasireddi and Prof. Suri S. Iyer

      Article first published online: 30 MAR 2015 | DOI: 10.1002/anie.201412164

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      Flu finder: An electrochemical assay has been developed for the detection of influenza viruses using glucose-bearing substrates (SG1). By monitoring the release of glucose upon introduction of the virus, 19 different influenza strains have been successfully detected. The assay can also be used to rapidly measure drug susceptibility.

    8. Gold Photocatalysis

      A Highly Efficient Gold-Catalyzed Photoredox α-C(sp3)[BOND]H Alkynylation of Tertiary Aliphatic Amines with Sunlight

      Dr. Jin Xie, Dr. Shuai Shi, M. Sc. Tuo Zhang, M. Sc. Nina Mehrkens, Dr. Matthias Rudolph and Prof. Dr. A. Stephen K. Hashmi

      Article first published online: 30 MAR 2015 | DOI: 10.1002/anie.201412399

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      Golden sunshine: With 1-iodoalkynes as radical alkynylation reagents, unactivated tertiary aliphatic amines react in the presence of [Au2(μ-dppm)2]2+ (dppm=bis(diphenylphosphanyl)methane) in sunlight to afford propargylamines. A C[BOND]C coupling of an α-aminoalkyl radical and an alkynyl radical was proposed as the mechanism.

    9. Mechanochemistry

      Mechanophores with a Reversible Radical System and Freezing-Induced Mechanochemistry in Polymer Solutions and Gels

      Dr. Keiichi Imato, Atsushi Irie, Takahiro Kosuge, Dr. Tomoyuki Ohishi, Dr. Masamichi Nishihara, Prof. Atsushi Takahara and Prof. Hideyuki Otsuka

      Article first published online: 30 MAR 2015 | DOI: 10.1002/anie.201412413

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      Freezing-induced mechanochemistry: A new diarylbibenzofuranone-based mechanophore showed reversible color change by external forces through radical mechanism. By incorporating the mechanophore into polymer chains, it was revealed that freezing gels induced mechanical force along the chains, but the force was not large enough to cleave usual covalent bonds.

    10. Organic Electronics

      Synthesis of Polybenzoquinolines as Precursors for Nitrogen-Doped Graphene Nanoribbons

      Dr. David J. Dibble, Dr. Young S. Park, Amir Mazaheripour, Mehran J. Umerani, Dr. Joseph W. Ziller and Prof. Alon A. Gorodetsky

      Article first published online: 30 MAR 2015 | DOI: 10.1002/anie.201411740

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      Towards nitrogen-doped nanoribbons: A previously unknown class of benzoquinoline-based materials was synthesized via the aza-Diels–Alder reaction. The reported straightforward and facile methodology provides ready access to a potentially diverse range of polybenzoquinolines. These materials hold promise as key intermediates for the synthesis of modular nitrogen-doped graphene nanoribbons.

  4. News

  5. Communications

    1. Asymmetric Catalysis

      Direct Catalytic Asymmetric Aldol Reaction of an α-Azido Amide

      Dr. Karin Weidner, Zhongdong Sun, Dr. Naoya Kumagai and Prof. Dr. Masakatsu Shibasaki

      Article first published online: 30 MAR 2015 | DOI: 10.1002/anie.201501607

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      The direct aldol reaction of an α-azido 7-azaindolinylamide is promoted by a Cu-based catalyst. Aromatic aldehydes bearing an ortho substituent exhibited diastereodivergency depending on the nature of the chiral ligands used. A vicinal azido alcohol unit led to the corresponding aziridine, and facile hydrolysis of the 7-azaindolinylamide moiety furnished enantioenriched β-hydroxy-α-azido carboxylic acid derivatives.

    2. Porphycenes

      meso-Dibenzoporphycene has a Large Bathochromic Shift and a Porphycene Framework with an Unusual Cis Tautomeric Form

      Dr. Koji Oohora, Ayumu Ogawa, Tamaki Fukuda, Dr. Akira Onoda, Prof. Dr. Jun-ya Hasegawa and Prof. Dr. Takashi Hayashi

      Article first published online: 30 MAR 2015 | DOI: 10.1002/anie.201501496

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      Put a ring on it: The insertion of two benzene moieties at the meso positions of a porphycene framework yields meso-dibenzoporphycene (mDBPc). The compound has a small electrochemical HOMO–LUMO gap (0.81 eV) and an NIR absorption band at 1047 nm. X-ray photoelectron spectroscopy and a theoretical study indicate that, unusually for a porphycene derivative, the cis tautomeric form of the porphycene framework is more stable than the trans form.

    3. High-Energy-Density Materials

      Energetic Materials with Promising Properties: Synthesis and Characterization of 4,4′-Bis(5-nitro-1,2,3-2H-triazole) Derivatives

      Dr. Chunlin He and Prof. Jean'ne M. Shreeve

      Article first published online: 30 MAR 2015 | DOI: 10.1002/anie.201412303

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      The hunt for high energy: Derivatives of 4,4′-bis(5-nitro-1,2,3-2H-triazole) were synthesized by different functionalization strategies. Competitive detonation properties were achieved and compared to reported analogues of fully carbon-nitrated bis(azole) compounds.

    4. Porphyrinoids

      meso,β-Oligohaloporphyrins as Useful Synthetic Intermediates of Diphenylamine-Fused Porphyrin and meso-to-meso β-to-β Doubly Butadiyne-Bridged Diporphyrin

      Norihito Fukui, Prof. Dr. Hideki Yorimitsu and Prof. Dr. Atsuhiro Osuka

      Article first published online: 30 MAR 2015 | DOI: 10.1002/anie.201501149

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      Doubled over: Chlorination of β-haloporphyrins with 2-chloro-1,3-bis(methoxycarbonyl)guanidine (Palau′Chlor) proceeded selectively at the neighboring unsubstituted meso position to afford meso,β-oligohaloporphyrins, which are useful intermediates of porphyrin-based extended π systems. For example, meso-chloro-β-iodoporphyrin was transformed stepwise into an efficiently conjugated meso-to-meso,β-to-β doubly butadiyne-linked porphyrin dimer.

  6. Cover Pictures

    1. Intracellular Modulation of Excited-State Dynamics in a Chromophore Dyad: Differential Enhancement of Photocytotoxicity Targeting Cancer Cells

      Dr. Safacan Kolemen, Dr. Murat Işık, Gyoung Mi Kim, Dabin Kim, Hao Geng, Muhammed Buyuktemiz, Tugce Karatas, Prof. Xian-Fu Zhang, Prof. Yavuz Dede, Prof. Juyoung Yoon and Prof. Engin U. Akkaya

      Article first published online: 27 MAR 2015 | DOI: 10.1002/anie.201502270

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      Orthogonal BODIPY dimers offer exciting potential as activatable photosensitizers for photodynamic therapy. In their Communication (DOI: 10.1002/anie.201411962), J. Yoon, E. U. Akkaya et al. report a photosensitizer that is switched on by a reaction with glutathione (GSH). Comparative cell culture data reveal that the agent is preferentially activated in cancer cells as they feature a higher glutathione level than normal cells.

    2. Formation of a Fluorous/Organic Biphasic Supramolecular Octopus Assembly for Enhanced Porphyrin Phosphorescence in Air

      Prof. Dr. Chi Yang, Dr. Ravi K. Arvapally, Dr. Sammer M. Tekarli, Gustavo A. Salazar, Dr. Oussama Elbjeirami, Dr. Xiaoping Wang and Prof. Dr. Mohammad A. Omary

      Article first published online: 27 MAR 2015 | DOI: 10.1002/anie.201502476

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      Supramolecular octopus couples form when a positively quadrupolar cyclic AgI–triazolate trimer with fluorous octopus arms electrostatically attracts a negatively quadrupolar free porphyrin or a PtII porphyrin with shorter alkyl octopus arms. In their Communication (DOI: 10.1002/anie.201411462), C. Yang, M. A. Omary et al. show that in this system, the phosphorescence of the PtII porphyrin is enhanced under ambient conditions as O2 and self-quenching processes are suppressed.

  7. Communications

    1. Protein Structure Determination

      The Double-Histidine Cu2+-Binding Motif: A Highly Rigid, Site-Specific Spin Probe for Electron Spin Resonance Distance Measurements

      Timothy F. Cunningham, Miriam R. Putterman, Astha Desai, Prof. W. Seth Horne and Prof. Sunil Saxena

      Article first published online: 27 MAR 2015 | DOI: 10.1002/anie.201501968

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      That’s great, DEER! When a double-histidine Cu2+-binding motif (shown in blue) assembled in situ from natural amino acid residues and a metal salt was used as a rigid spin probe for double electron–electron resonance (DEER) distance measurements, dramatically narrower and readily interpretable distance distributions were observed than with a commonly used flexible spin label (red). Molecular modeling of an unlabeled protein gave a distance within 0.5 Å of the experimental value.

    2. Polycycles

      A Metal-Free N-Annulated Thienocyclopentaperylene Dye: Power Conversion Efficiency of 12 % for Dye-Sensitized Solar Cells

      Zhaoyang Yao, Dr. Min Zhang, Dr. Renzhi Li, Lin Yang, Yongna Qiao and Prof. Peng Wang

      Article first published online: 27 MAR 2015 | DOI: 10.1002/anie.201501195

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      Power trip: A perylene dye derived from N-annulated thienocyclopentaperylene, which is characterized by a low-energy gap and a high electron injection yield, was synthesized for dye-sensitized solar cells. A high power conversion efficiency of 12 %, at an irradiance of the AM1.5G sunlight, was achieved. This efficiency is the highest achieved thus far by using just a metal-free organic dye.

    3. Polycyclic π Systems

      A Pyrene-Fused N-Heteroacene with Eleven Rectilinearly Annulated Aromatic Rings

      Dipl.-Chem. Bernd Kohl, Dr. Frank Rominger and Prof. Dr. Michael Mastalerz

      Article first published online: 27 MAR 2015 | DOI: 10.1002/anie.201411972

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      Acenes eleven: A highly soluble pyrene-fused undecacene is prepared by adding end-capping triptycenylene units to the linear π system (see structure, N blue). The new compound shows a high tendency to crystallize; two polymorphs from dichlorobenzene and chloroform solutions could be obtained.

    4. Heterocycle Synthesis

      The Cyano Group as a Traceless Activation Group for the Intermolecular [3+2] Cycloaddition of Azomethine Ylides: A Five-Step Synthesis of (±)-Isoretronecanol

      Jundong Li, Huaibo Zhao, Xunjin Jiang, Xiance Wang, Haiming Hu, Lei Yu and Prof. Dr. Yandong Zhang

      Article first published online: 27 MAR 2015 | DOI: 10.1002/anie.201500961

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      Without a trace… A highly stereoselective cycloaddition strategy provided efficient access to a diverse array of 5-unsubstituted pyrrolidines and enabled a five-step total synthesis of isoretronecanol (see scheme). A novel role of sodium borohydride in reductive decyanation was observed.

    5. Bacterial Detection

      Simultaneous Capture, Detection, and Inactivation of Bacteria as Enabled by a Surface-Enhanced Raman Scattering Multifunctional Chip

      Dr. Houyu Wang, Dr. Yanfeng Zhou, Xiangxu Jiang, Bin Sun, Ying Zhu, Hui Wang, Dr. Yuanyuan Su and Prof. Yao He

      Article first published online: 27 MAR 2015 | DOI: 10.1002/anie.201412294

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      No chip off the old block: A multifunctional platform was developed for the simultaneous capture, sensing by surface-enhanced Raman scattering (SERS), and inactivation of bacteria (see picture). The SERS chip featured excellent reproducibility, good bacterial-capture efficiency, high sensitivity, and a high antibacterial rate, and was found to be suitable for capturing and discriminating bacteria in real systems.

  8. Book Reviews

    1. Pincer and Pincer-Type Complexes Applications in Organic Synthesis and Catalysis. Edited by Kálmán J. Szabó and Ola F. Wendt

      Karl Kirchner

      Article first published online: 26 MAR 2015 | DOI: 10.1002/anie.201501805

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      , Wiley-VCH, Weinheim 2014. 320 pp., € 139.00.—ISBN 978-3527334421.

  9. Cover Pictures

    1. Dipolar Rotors Orderly Aligned in Mesoporous Fluorinated Organosilica Architectures

      Dr. Silvia Bracco, Dr. Mario Beretta, Dr. Alice Cattaneo, Prof. Angiolina Comotti, Prof. Andrea Falqui, Dr. Ke Zhao, Prof. Charles Rogers and Prof. Piero Sozzani

      Article first published online: 25 MAR 2015 | DOI: 10.1002/anie.201502272

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      Like dancers on ice who make pirouettes, dipolar molecular rotors have been programmed to spin in mesoporous fluorinated organosilica materials. In their Communication (DOI: 10.1002/anie.201412412), A. Comotti, P. Sozzani, et al. report on the fast reorientation of the carbon–fluorine dipole. The relaxation rates obtained by NMR spectroscopy were modulated by the dipole dynamics, which in turn were regulated by I2 vapor entering the pores.

  10. Obituaries

    1. Carl Djerassi (19232015)

      Prof. Dr. Richard N. Zare

      Article first published online: 25 MAR 2015 | DOI: 10.1002/anie.201501335

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      Carl Djerassi died at the age of 91 on January 30, 2015. He is best known for developing the synthetic hormone used to the present day in the oral contraceptive commonly known as The Pill. Djerassi’s other achievements include the use of mass spectrometry in organic chemistry, and extensive research on antibiotics and marine natural products. He was also an author of plays, poems, and short stories, including Oxygen, written together with Roald Hoffmann.

  11. Communications

    1. NMR Spectroscopy

      1D NMR Homodecoupled 1H Spectra with Scalar Coupling Constants from 2D NemoZS-DIAG Experiments

      Axelle Cotte and Dr. Damien Jeannerat

      Article first published online: 25 MAR 2015 | DOI: 10.1002/anie.201500831

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      Clear separation: The overlapping 1H multiplets of a 1D NMR spectrum are easily resolved in a 2D nemoZS-DIAG spectrum. An automatic analysis can extract the scalar coupling constants and produce a homodecoupled 1D 1H spectrum.

    2. Crystallization | Very Important Paper

      Secondary Crystal Nucleation: Nuclei Breeding Factory Uncovered

      Prof. Jamshed Anwar, Dr. Shahzeb Khan and Prof. Dr. Lennart Lindfors

      Article first published online: 25 MAR 2015 | DOI: 10.1002/anie.201501216

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      Crystal clear: Molecular dynamics simulations uncover the nuclei breeding factory responsible for secondary nucleation in crystal growth. The question why a few crystal seeds give rise to a many-fold increase in new crystals is answered. This mechanistic insight will enable better control in engineering crystalline products to design.

    3. Synthetic Methods

      Organocatalytic Enantioselective Oxidative C[BOND]H Alkenylation and Arylation of N-Carbamoyl Tetrahydropyridines and Tetrahydro-β-carbolines

      Xigong Liu, Zhilin Meng, Chengkun Li, Prof. Hongxiang Lou and Prof. Lei Liu

      Article first published online: 25 MAR 2015 | DOI: 10.1002/anie.201500703

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      Without a metal: A large variety of N-heterocycles and boronates were subjected to the title reactions, which proceeded with high efficiency and excellent regio- and enantioselectivity. The new method was applied in complex molecule synthesis.

    4. DNA Nanocages | Very Important Paper

      Structural Transformation: Assembly of an Otherwise Inaccessible DNA Nanocage

      Dr. Yulin Li, Dr. Cheng Tian, Zhiyu Liu, Prof. Wen Jiang and Prof. Chengde Mao

      Article first published online: 25 MAR 2015 | DOI: 10.1002/anie.201500755

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      One way or another: A strategy has been developed for the assembly of DNA nanocages that can not be assembled directly. In this approach a precursor DNA nanocage is assembled first and is then isothermally transformed into a desired, complicated nanocage. Dramatic changes in the 3D structures and topologies accompany the transformation, as shown by native polyacrylamide gel electrophoresis and cryogenic electron microscopy imaging.

    5. Cluster Compounds

      Alkynyl-Protected Au23 Nanocluster: A 12-Electron System

      Xian-Kai Wan, Shang-Fu Yuan, Dr. Qing Tang, Prof. Dr. De-en Jiang and Prof. Dr. Quan-Ming Wang

      Article first published online: 25 MAR 2015 | DOI: 10.1002/anie.201500590

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      A heart of gold: Gold nanocluster [Au23(PhC[TRIPLE BOND]C)9(Ph3P)6]2+ has an unprecedented Au17 kernel protected by three PhC2-Au-C2(Ph)-Au-C2Ph motifs (see picture; green, yellow, and red) and six Ph3P units. DFT electronic structure analysis suggests that the stability of the 12-electron cluster is due to the splitting of the superatomic 1D orbitals under the D3h symmetry of the Au17 core. Atom colors: Au=orange/blue; P=purple; C=gray.

    6. Structure Elucidation

      Superstructure of a Substituted Zeolitic Imidazolate Metal–Organic Framework Determined by Combining Proton Solid-State NMR Spectroscopy and DFT Calculations

      Dr. Maria Baias, Dr. Anne Lesage, Dr. Sonia Aguado, Dr. Jerome Canivet, Dr. Virginie Moizan-Basle, Dr. Nathalie Audebrand, Dr. David Farrusseng and Prof. Lyndon Emsley

      Article first published online: 25 MAR 2015 | DOI: 10.1002/anie.201500518

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      The superstructure of a substituted zeolitic imidazolate metal–organic framework was determined from a combination of experimental NMR chemical shifts and DFT-calculated shifts (see picture). The study indicates the presence of two different environments for each type of functional group in the metal–organic framework.

    7. Cell Adhesion

      Molecular Encryption and Reconfiguration for Remodeling of Dynamic Hydrogels

      Shihui Li, Erin R. Gaddes, Dr. Niancao Chen and Prof. Yong Wang

      Article first published online: 25 MAR 2015 | DOI: 10.1002/anie.201500397

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      Reversible encryption: Dynamic materials for regulation of cell adhesion are important to a variety of biological and biomedical applications. This study demonstrates an encrypted ligand and hydrogel with the capability of inducing and inhibiting cell adhesion, which is controlled by hybridization reaction-driven molecular reconfiguration. U=unblocking sequence, R=recovering sequence.

    8. Proteomics | Hot Paper

      Multifunctional Reagents for Quantitative Proteome-Wide Analysis of Protein Modification in Human Cells and Dynamic Profiling of Protein Lipidation During Vertebrate Development

      Dr. Malgorzata Broncel, Dr. Remigiusz A. Serwa, Paulina Ciepla, Dr. Eberhard Krause, Prof. Margaret J. Dallman, Prof. Anthony I. Magee and Prof. Edward W. Tate

      Article first published online: 25 MAR 2015 | DOI: 10.1002/anie.201500342

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      Catch and release: Multifunctional capture reagents were developed that enable enzymatically-triggered release and direct detection of lipid-modified peptides by mass spectrometry. Dynamic proteome lipidation was visualized, enriched, and identified on an unprecedented scale, both in cells and in a developing zebrafish embryo.

    9. Boron-Doped Graphite

      Theory and Practice: Bulk Synthesis of C3B and its H2- and Li-Storage Capacity

      Timothy C. King, Peter D. Matthews, Hugh Glass, Jonathan A. Cormack, Dr. Juan Pedro Holgado, Dr. Michal Leskes, Dr. John M. Griffin, Dr. Oren A. Scherman, Dr. Paul D. Barker, Prof. Clare P. Grey, Dr. Siân E. Dutton, Prof. Richard M. Lambert, Dr. Gary Tustin, Prof. Ali Alavi and Prof. Dominic S. Wright

      Article first published online: 25 MAR 2015 | DOI: 10.1002/anie.201412200

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      C3B or not C3B that is the question—Previous theoretical predictions suggest that the stoichiometrically doped graphite C3B should be a promising H2- and Li-storage material, with potentially important applications in power storage. The first experimental measurements of the real material indicate, however, that disorder is a limiting factor for the use of C3B as an energy storage material.

    10. Biosynthetic Pathways

      Unprecedented Quassinoids with Promising Biological Activity from Harrisonia perforata

      Dr. Xin Fang, Ying Tong Di, Yu Zhang, Dr. Zhi Ping Xu, Prof. Yang Lu, Qian Qian Chen, Prof. Qi Tai Zheng and Prof. Dr. Xiao Jiang Hao

      Article first published online: 25 MAR 2015 | DOI: 10.1002/anie.201412126

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      An active family: A quassinoid with a unique cagelike 2,4-dioxaadamantane ring system (see structure) was isolated along with biosynthetically related quassinoids from the twigs and stem of Harrisonia perforata. The compounds demonstrated insecticidal activity, antagonist activity at the nicotinic acetylcholine receptor of insects, and potent cytotoxicity. Their discovery provides an alternative origin of the quassinoid family of compounds.

    11. Photocatalysis

      Activation of Water in Titanium Dioxide Photocatalysis by Formation of Surface Hydrogen Bonds: An In Situ IR Spectroscopy Study

      Dr. Hua Sheng, Hongna Zhang, Dr. Wenjing Song, Dr. Hongwei Ji, Prof. Wanhong Ma, Prof. Chuncheng Chen and Prof. Jincai Zhao

      Article first published online: 25 MAR 2015 | DOI: 10.1002/anie.201412035

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      Switching the water adsorption mode on TiO2 to dual H-bonding by the presence of fluorine atoms at the surface not only thermodynamically enables the hole transfer to the water molecules, but also facilitates the proton-coupled electron transfer during water oxidation. This phenomenon is established by IR spectroscopy studies and calculations.

    12. Radical Cascades

      Metal Bridging for Directing and Accelerating Electron Transfer as Exemplified by Harnessing the Reactivity of AIBN

      Dr. Yinjun Xie, Dr. Shengmei Guo, Prof. Longmin Wu, Prof. Chungu Xia and Prof. Dr. Hanmin Huang

      Article first published online: 25 MAR 2015 | DOI: 10.1002/anie.201411974

      Thumbnail image of graphical abstract

      Electron bridge: An efficient strategy for improving the electron transfer between radicals and enolates has been developed. A redox-active copper species activates the free radical and brings the radical and enolate within proximity, which in turn facilitates the electron transfer. Thus, a cascade reaction for the synthesis of highly functionalized pyrrolidine-2,5-diones was developed.

    13. Lignin Valorization

      Ruthenium-Catalyzed C[BOND]C Bond Cleavage in Lignin Model Substrates

      Thorsten vom Stein, Dr. Tim den Hartog, Dr. Julien Buendia, Dr. Spas Stoychev, Jakob Mottweiler, Prof. Dr. Carsten Bolm, Prof. Dr. Jürgen Klankermayer and Prof. Dr. Walter Leitner

      Article first published online: 25 MAR 2015 | DOI: 10.1002/anie.201410620

      Thumbnail image of graphical abstract

      Sele-C-C-tivity! Highly selective C[BOND]C bond cleavage of model compounds for the lignin β-O-4 linkage was promoted by a catalyst formed in situ from [Ru(Cl)(H)(PPh3)3] and the ligand triphos (see scheme). Mechanistic investigations indicated a hydrogen-transfer-based retro-aldol pathway for this transformation.

    14. B,N Azo Dyes | Hot Paper

      Formation of BN Isosteres of Azo Dyes by Ring Expansion of Boroles with Azides

      Prof. Dr. Holger Braunschweig, Dr. Mehmet Ali Celik, Florian Hupp, Dr. Ivo Krummenacher and Lisa Mailänder

      Article first published online: 25 MAR 2015 | DOI: 10.1002/anie.201500970

      Thumbnail image of graphical abstract

      Azo borealis: The first 1,2-azaborinine-substituted azo dyes have been synthesized using sterically demanding boroles and organic azides. The ring-expansion mechanism of the unexpected formation of the bright yellow chromophores was investigated by DFT calculations.

  12. Highlights

    1. Cycloaddition

      Thrilling Strain! Donor–Acceptor-Substituted Cyclobutanes for the Synthesis of (Hetero)Cyclic Compounds

      Prof. Dr. Hans-Ulrich Reissig and Dr. Reinhold Zimmer

      Article first published online: 24 MAR 2015 | DOI: 10.1002/anie.201501135

      Thumbnail image of graphical abstract

      The analogy goes further: Following the often-studied donor–acceptor-substituted cyclopropanes, the corresponding cyclobutane derivatives were employed for the ring-strain-driven stereoselective syntheses of carbo- and heterocycles.

  13. Cover Pictures

    1. Catalytic Asymmetric Hydroalkenylation of Vinylarenes: Electronic Effects of Substrates and Chiral N-Heterocyclic Carbene Ligands

      Prof. Dr. Chun-Yu Ho, Chun-Wa Chan and Lisi He

      Article first published online: 24 MAR 2015 | DOI: 10.1002/anie.201502318

      Thumbnail image of graphical abstract

      An asymmetric cross-hydroalkenylation catalyzed by [NiH] complexes provides branched gem-disubstituted olefins with high enantio- and chemoselectivity, depending on the steric and electronic effects of the substrates and N-heterocyclic carbene (NHC) ligands. In their Communication (DOI: 10.1002/anie.201411882), C.-Y. Ho and co-workers rule out a π,π-stacking mechanism and suggest that the N-aryl rings of the NHCs possibly “move like wings” by coordinating a π system with NiII.

  14. Communications

    1. Synthetic Methods

      Palladium-Catalyzed C[BOND]H Activation of N-Allyl Imines: Regioselective Allylic Alkylations to Deliver Substituted Aza-1,3-Dienes

      Prof. Dr. Barry M. Trost, Dr. Subham Mahapatra and Dr. Martin Hansen

      Article first published online: 24 MAR 2015 | DOI: 10.1002/anie.201501322

      Thumbnail image of graphical abstract

      Making one into two: Palladium-catalyzed direct C(sp3)[BOND]H activation of an N-allyl imine led to the generation of an all-carbon π-allyl complex which presumably remains in equilibrium with a rare 2-aza π-allyl species. Nucleophilic attack on the π-allyl intermediates gave either a 1-aza-1,3-diene or 2-aza-1,3-diene in a completely regioselective manner.

    2. Alloys | Very Important Paper

      Origin of Extraordinary Stability of Square-Planar Carbon Atoms in Surface Carbides of Cobalt and Nickel

      Anjan Nandula, Quang Thang Trinh, Prof. Mark Saeys and Prof. Anastassia N. Alexandrova

      Article first published online: 24 MAR 2015 | DOI: 10.1002/anie.201501049

      Thumbnail image of graphical abstract

      Out for the count: The unusual stability and reconstruction of surface cobalt and nickel carbides containing square-planar carbon atoms is explained by local aromaticity and electron count. A chemical bonding model for these systems is presented and explains the unusual structure, special stability, and the reconstruction. Several new aromatic and stable two-dimensional alloys are predicted.

    3. Asymmetric Catalysis

      Assembly of Fluorinated Quaternary Stereogenic Centers through Catalytic Enantioselective Detrifluoroacetylative Aldol Reactions

      Chen Xie, Lingmin Wu, Dr. Jianlin Han, Prof. Dr. Vadim A. Soloshonok and Dr. Yi Pan

      Article first published online: 24 MAR 2015 | DOI: 10.1002/anie.201500908

      Thumbnail image of graphical abstract

      High selectivity: Asymmetric catalytic detrifluoroacetylative aldol addition reactions between 2-fluoro-1,3-diketones/hydrates and aldehydes afford α-fluoro-β-hydroxyketone products containing C[BOND]F quaternary stereogenic centers in good yields, high diastereo-, and enantioselectivities.

    4. Terpene Biosynthesis

      Structures and Biosynthesis of Corvol Ethers—Sesquiterpenes from the Actinomycete Kitasatospora setae

      Patrick Rabe, Dr. Khomaizon A. K. Pahirulzaman and Prof. Dr. Jeroen S. Dickschat

      Article first published online: 24 MAR 2015 | DOI: 10.1002/anie.201501119

      Thumbnail image of graphical abstract

      Ether way: Two new sesquiterpene ethers were obtained by incubation of farnesyl diphosphate with a recombinant terpene cyclase from Kitasatospora setae. The structures of both terpenes were elucidated by NMR spectroscopic methods. Incubation experiments with isotopically labeled precursors gave detailed insight into the mechanism of the bacterial sesquiterpene cyclase.

    5. Synthetic Methods

      Palladium(II)/Brønsted Acid-Catalyzed Enantioselective Oxidative Carbocyclization–Borylation of Enallenes

      Tuo Jiang, Dr. Teresa Bartholomeyzik, Dr. Javier Mazuela, Jochen Willersinn and Prof. Dr. Jan-E. Bäckvall

      Article first published online: 24 MAR 2015 | DOI: 10.1002/anie.201501048

      Thumbnail image of graphical abstract

      Biphenol-type chiral phosphoric acids serve as co-catalysts to induce enantioselectivity in the palladium(II)-catalyzed oxidative carbocyclization–borylation of enallenes. The method was used to prepare a number of enantioenriched borylated carbocycles in high yields and enantioselectivities (up to 93 %). BQ=benzoquinone, pin=pinacolato.

    6. Mononuclear Lanthanide SMMs

      A Trigonal-Pyramidal Erbium(III) Single-Molecule Magnet

      Andrew J. Brown, Dr. Dawid Pinkowicz, Dr. Mohamed R. Saber and Prof. Kim R. Dunbar

      Article first published online: 24 MAR 2015 | DOI: 10.1002/anie.201411190

      Thumbnail image of graphical abstract

      Riding the wave of erbium SMMs: The first trigonal pyramidal mononuclear erbium(III) single-molecule magnet (SMM) was synthesized and its magnetic properties investigated. Despite containing an axial Cl ligand, which is expected to reduce the prolate nature of the erbium(III) ion, the molecule exhibits out-of-phase signals in the ac susceptibility data in the absence of an external field and hysteresis behavior up to 3 K.

    7. Porous capsules | Very Important Paper

      A Unique Fluoride Nanocontainer: Porous Molecular Capsules Can Accommodate an Unusually High Number of “Rather Labile” Fluoride Anions

      Somenath Garai, Dr. Mirta Rubčić, Dr. Hartmut Bögge, Dr. Erhard T. K. Haupt, Prof. Dr. Pierre Gouzerh and Prof. Dr. Achim Müller

      Article first published online: 24 MAR 2015 | DOI: 10.1002/anie.201411814

      Thumbnail image of graphical abstract

      Overloaded: Porous molecular nanocontainers of the {Mo132} Keplerate type can integrate a uniquely large number of fluorides. These F ions (see structure, green) are partly as coordinated ligands at both the {(MoVI)MoVI5O21(H2O)5(F)} pentagonal units (orange) and the linkers (blue), partly as a disordered water/fluoride assembly inside the cavity. The H2O ligands are shown as red spheres (larger red spheres are for H2O coordinated e.g. to the MoV centers of the linkers).

    8. Photodynamic Therapy | Hot Paper

      Intracellular Modulation of Excited-State Dynamics in a Chromophore Dyad: Differential Enhancement of Photocytotoxicity Targeting Cancer Cells

      Dr. Safacan Kolemen, Dr. Murat Işık, Gyoung Mi Kim, Dabin Kim, Hao Geng, Muhammed Buyuktemiz, Tugce Karatas, Prof. Xian-Fu Zhang, Prof. Yavuz Dede, Prof. Juyoung Yoon and Prof. Engin U. Akkaya

      Article first published online: 24 MAR 2015 | DOI: 10.1002/anie.201411962

      Thumbnail image of graphical abstract

      Selective switch: A dimeric BODIPY dye with reduced symmetry is ineffective as a photosensitizer unless it is activated by a reaction with intracellular glutathione (GSH). Staining with red-fluorescent Annexin V shows that the photosensitizer is preferentially switched on in cancer cells, which feature a higher GSH level than normal cells.

    9. Monofluoromethylation

      Nickel-Catalyzed Monofluoromethylation of Aryl Boronic Acids

      Yi-Ming Su, Guang-Shou Feng, Zhen-Yu Wang, Dr. Quan Lan and Prof. Dr. Xi-Sheng Wang

      Article first published online: 24 MAR 2015 | DOI: 10.1002/anie.201412026

      Thumbnail image of graphical abstract

      Aryl boronic acids can be monofluoromethylated under nickel catalysis. The utility of this method is demonstrated by the monofluoromethylation of a borylated and acyl-protected derivative of the statin drug ezetimibe. Mechanistic investigations indicate that a fluoromethyl radical is involved in the NiI/NiIII catalytic cycle.

    10. DNA Nanostructures

      A Signal-Passing DNA-Strand-Exchange Mechanism for Active Self-Assembly of DNA Nanostructures

      Dr. Jennifer E. Padilla, Dr. Ruojie Sha, Dr. Martin Kristiansen, Prof. Junghuei Chen, Prof. Natasha Jonoska and Prof. Nadrian C. Seeman

      Article first published online: 24 MAR 2015 | DOI: 10.1002/anie.201500252

      Thumbnail image of graphical abstract

      Signal passing in DNA: A triggered self-assembly process of DNA nanostructured tiles is demonstrated. The DNA-strand-exchange mechanism sends a signal across a tile leading to a binding event by activation of a second binding site 18 nm away. Five unique DNA tiles self-assemble sequentially in a domino-like cascade.

    11. NMR Spectroscopy

      Quantitative Structural Constraints for Organic Powders at Natural Isotopic Abundance Using Dynamic Nuclear Polarization Solid-State NMR Spectroscopy

      Dr. Giulia Mollica, Myriam Dekhil, Dr. Fabio Ziarelli, Dr. Pierre Thureau and Prof. Stéphane Viel

      Article first published online: 23 MAR 2015 | DOI: 10.1002/anie.201501172

      Thumbnail image of graphical abstract

      Structure elucidation: 13C–13C double-quantum (DQ) build-up curves (see picture, center) are recorded using dynamic nuclear polarization solid-state NMR spectroscopy. Structural constraints based on these curves are quantitatively related to the crystal structures of organic microcrystalline powders at natural isotopic abundance, as shown herein for theophylline. τDQ=DQ excitation time.

    12. Heterogeneous Catalysis

      SBA-15-Oxynitrides as a Solid-Base Catalyst: Effect of Nitridation Temperature on Catalytic Activity

      Baljeet Singh, Dr. Kaustubh R. Mote, Dr. C. S. Gopinath, Prof. Dr. P. K. Madhu and Prof. Dr. Vivek Polshettiwar

      Article first published online: 20 MAR 2015 | DOI: 10.1002/anie.201501015

      Thumbnail image of graphical abstract

      Oxynitride solid: Solid bases, such as SBA-15-oxynitrides, have attracted considerable interest for potential applications as catalysts in important industrial processes. Reported here is that tuning the temperature of nitridation (ammonolysis) leads to enhanced catalytic activity of these solid bases. Detailed studies are discussed to explain this change in activity.

    13. Difluoromethylation

      In Situ Generation of Difluoromethyl Diazomethane for [3+2] Cycloadditions with Alkynes

      Dr. Pavel K. Mykhailiuk

      Article first published online: 20 MAR 2015 | DOI: 10.1002/anie.201501529

      Thumbnail image of graphical abstract

      A new reagent: The elusive chemical reagent CF2HCHN2 was generated in situ for the first time and further reacted with alkynes in a [3+2] cycloaddition reaction. This transformation constitutes a novel and efficient approach to agrochemically important difluoromethylated pyrazoles.

  15. News

  16. Reviews

    1. Asymmetric Synthesis

      Development of Chiral Sulfoxide Ligands for Asymmetric Catalysis

      Prof. Dr. Barry M. Trost and Dr. Meera Rao

      Article first published online: 20 MAR 2015 | DOI: 10.1002/anie.201411073

      Thumbnail image of graphical abstract

      Auspicious ligands: Sulfoxides with chirality at the sulfur atom have mainly been used as chiral auxiliaries for diastereoselective reactions and have only recently emerged as a versatile class of chiral ligands. In this Review, the development of chiral sulfoxide ligands for asymmetric catalysis is discussed, and metal–sulfoxide bonding and strategies for the synthesis of enantiopure sulfoxides are described.

  17. Communications

    1. Fluorescent Probes | Hot Paper

      Strained Cyclooctyne as a Molecular Platform for Construction of Multimodal Imaging Probes

      Yao Sun, Dr. Xiaowei Ma, Kai Cheng, Biying Wu, Jianli Duan, Hao Chen, Lihong Bu, Ruiping Zhang, Prof. Xianming Hu, Zixin Deng, Lei Xing, Xuechuan Hong and Prof. Zhen Cheng

      Article first published online: 20 MAR 2015 | DOI: 10.1002/anie.201500941

      Thumbnail image of graphical abstract

      Spitting image: The products of the base-catalyzed addition of various functional molecules to bicyclo[6.1.0]nonyne-based scaffolds provided precursors for novel dual-modality (PET and NIRF) uPAR-targeted imaging probes. The probes were evaluated in U87MG cells and tumor-bearing mice models, thus demonstrating excellent imaging characteristics.

    2. Self-Assembly

      Self-Discriminating Termination of Chiral Supramolecular Polymerization: Tuning the Length of Nanofibers

      Dr. Jatish Kumar, Dr. Hiroyuki Tsumatori, Dr. Junpei Yuasa, Prof. Tsuyoshi Kawai and Dr. Takuya Nakashima

      Article first published online: 20 MAR 2015 | DOI: 10.1002/anie.201500292

      Thumbnail image of graphical abstract

      Going to great lengths: The length of chiral supramolecular polymers was precisely controlled through varying the enantiomeric excess. The homochiral assembly favors fibrous growth whereas heterochiral assembly preferentially leads to nanoparticles. The stronger heterochiral bindings at the growing ends of fibers effectively terminate the elongation of the fibers.

    3. B,N Heterocycles

      Reversible 1,1-Hydroboration: Boryl Insertion into a C[BOND]N Bond and Competitive Elimination of HBR2 or R[BOND]H

      Deng-Tao Yang, Soren K. Mellerup, Xiang Wang, Dr. Jia-Sheng Lu and Prof. Dr. Suning Wang

      Article first published online: 20 MAR 2015 | DOI: 10.1002/anie.201500487

      Thumbnail image of graphical abstract

      NBC news: Boranes (HBR2) have been found to undergo facile and unprecedented 1,1-hydroboration with pyrido[1,2-a]isoindole (A) via an intermediate D, generating a variety of BN heterocycles (B) that can either undergo thermal retro-hydroboration, or, R[BOND]H elimination producing brightly fluorescent BN-phenanthrenes (C).

    4. Reaction Mechanisms | Very Important Paper

      A Constellation of Deuterium-Labeled Silanes as a Simple Mechanistic Probe not Requiring Absolute Configuration Determination

      Dr. Thomas Fallon and Prof. Dr. Martin Oestreich

      Article first published online: 20 MAR 2015 | DOI: 10.1002/anie.201500750

      Thumbnail image of graphical abstract

      Silicon stargazing: A new type of mechanistic probe is designed and evaluated. A cocktail of deuterium-labeled hydrosilanes provides a “silent” stereochemical relationship between the silicon atom and the probe’s backbone as the basis of the analysis. This technique does not suffer from the biases of traditional methods, nor does it require the determination of the absolute configuration.

  18. Reviews

    1. Electrode Materials

      Nickel-Rich Layered Lithium Transitional-Metal Oxide for High-Energy Lithium-Ion Batteries

      Dr. Wen Liu, Pilgun Oh, Dr. Xien Liu, Min-Joon Lee, Woongrae Cho, Sujong Chae, Prof. Dr. Youngsik Kim and Prof. Dr. Jaephil Cho

      Article first published online: 20 MAR 2015 | DOI: 10.1002/anie.201409262

      Thumbnail image of graphical abstract

      The end is Ni: Over the past two decades, nickel-rich materials, have become highly promising candidates for high-energy cathode materials for lithium-ion batteries. This Review brings a new perspective to Ni-rich materials as well as providing a comprehensive account of recent progress and limits, and new utilization possibilities for these materials. ESS=energy storage systems, EV=electric vehicles, HEV=hybrid electric vehicles, Mobile=mobile appliances.

  19. Communications

    1. Zeolite Synthesis | Hot Paper

      Widening Synthesis Bottlenecks: Realization of Ultrafast and Continuous-Flow Synthesis of High-Silica Zeolite SSZ-13 for NOx Removal

      Zhendong Liu, Prof. Dr. Toru Wakihara, Dr. Kazunori Oshima, Daisuke Nishioka, Yuusuke Hotta, Dr. Shanmugam P. Elangovan, Yutaka Yanaba, Prof. Dr. Takeshi Yoshikawa, Dr. Watcharop Chaikittisilp, Takeshi Matsuo, Takahiko Takewaki and Prof. Dr. Tatsuya Okubo

      Article first published online: 20 MAR 2015 | DOI: 10.1002/anie.201501160

      Thumbnail image of graphical abstract

      Bottle opener: SSZ-13 is a zeolite commercialized as a catalyst to remove nitrogen oxides (NOx). However, its long synthesis time is one of the biggest barriers to large-scale production. An ultrafast synthesis route now allows SSZ-13 to be synthesized in 10 min and thus facilitates continuous preparation of SSZ-13. The fast-synthesized SSZ-13 exhibits outstanding performance for the NOx removal.

  20. Cover Pictures

    1. Environment-Sensitive Fluorescent Probe: A Benzophosphole Oxide with an Electron-Donating Substituent

      Eriko Yamaguchi, Chenguang Wang, Prof. Dr. Aiko Fukazawa, Prof. Dr. Masayasu Taki, Dr. Yoshikatsu Sato, Taeko Sasaki, Dr. Minako Ueda, Prof. Dr. Narie Sasaki, Prof. Dr. Tetsuya Higashiyama and Prof. Dr. Shigehiro Yamaguchi

      Article first published online: 20 MAR 2015 | DOI: 10.1002/anie.201502276

      Thumbnail image of graphical abstract

      An electron-accepting benzophosphole oxide is combined with an electron-donating aminophenyl group to form a fluorescent probe. A. Fukazawa, T. Higashiyama, S. Yamaguchi et al. show in their Communication (10.1002/anie.201500229) that the probe exhibits a fluorescence color change as a function of solvent polarity while retaining high fluorescence quantum yields. The molecule was used as an adipocyte dye and allowed a fluorescence-based discrimination of the polarity of subcellular components.

  21. Essays

    1. Bürgenstock Conference

      50 Years in the Sun of Bürgenstock—On the Success Factors of a Famous Conference

      Prof. Dr. Klaus Müller

      Article first published online: 20 MAR 2015 | DOI: 10.1002/anie.201501161

      Thumbnail image of graphical abstract

      The secret of success: This year the famous “Bürgenstock Conference” will take place for the 50th time. This conference has become internationally one of the, if not the, most highly regarded conference in chemistry, chemical biology, and physical chemistry. What are the success factors of this conference? These as well as a number of perhaps more hidden figures and facts are discussed.

  22. Book Reviews

    1. Semiconductor Photocatalysis: Principles and Applications. By Horst Kisch

      Horst Hennig

      Article first published online: 20 MAR 2015 | DOI: 10.1002/anie.201501876

      Thumbnail image of graphical abstract

      Wiley-VCH, Weinheim 2015. 264 pp., € 126.00.—ISBN 978-3527335534

  23. Cover Pictures

    1. Early Formation of the Ion-Conducting Pore in Channelrhodopsin-2

      Jens Kuhne, Kirstin Eisenhauer, Dr. Eglof Ritter, Prof. Dr. Peter Hegemann, Prof. Dr. Klaus Gerwert and Prof. Franz Bartl

      Article first published online: 20 MAR 2015 | DOI: 10.1002/anie.201502275

      Thumbnail image of graphical abstract

      The light-gated ion channel channelrhodopsin-2 (ChR2) is the key protein in optogenetics. In their Communication (DOI: 10.1002/anie.201410180), K. Gerwert et al. elucidate channel opening at a molecular level by a combination of time-resolved FTIR spectroscopy and molecular dynamics simulations.

  24. Communications

    1. Metal–Organic Frameworks

      Crystalline Capsules: Metal–Organic Frameworks Locked by Size-Matching Ligand Bolts

      Dr. Hao Wang, Jian Xu, Da-Shuai Zhang, Qiang Chen, Rong-Mei Wen, Ze Chang and Prof. Xian-He Bu

      Article first published online: 20 MAR 2015 | DOI: 10.1002/anie.201500468

      Thumbnail image of graphical abstract

      Lock, stock, and barrel: A two-step “loading-locking” process has been developed to encapsulate target guest molecules in porous metal–organic frameworks (MOFs). In this approach, size-matching organic ligands are preselected and deliberately grafted onto open metal sites to lock the pores of the MOFs to prevent the leaching of guests. Rapid release of the encapsulated guests can be achieved by application of an external stimulus.

    2. Heterogeneous Catalysis

      Beyond Acid Strength in Zeolites: Soft Framework Counteranions for Stabilization of Carbocations on Zeolites and Its Implication in Organic Synthesis

      Dr. Jose R. Cabrero-Antonino, Dr. Antonio Leyva-Pérez and Prof. Avelino Corma

      Article first published online: 20 MAR 2015 | DOI: 10.1002/anie.201500864

      Thumbnail image of graphical abstract

      Stabilized carbocations: Zeolites are able to generate and stabilize medium-size (molecular weight ≈300 Da) delocalized carbocations on their surface under mild conditions to perform multifunctionalization reactions with catalytic activities comparable to that of strong homogenous Brønsted acids. Some of the products obtained here exhibit significant inhibition percentages against colon cancer cells.

    3. Ether Synthesis

      Alkyl Aryl Ether Bond Formation with PhenoFluor

      Dr. Xiao Shen, Constanze N. Neumann, Claudia Kleinlein, Nathaniel W. Goldberg and Prof. Dr. Tobias Ritter

      Article first published online: 20 MAR 2015 | DOI: 10.1002/anie.201500902

      Thumbnail image of graphical abstract

      From fluorination to etherification: A method for the formation of alkyl aryl ethers directly from the corresponding alcohols and phenols with PhenoFluor has been developed. The reaction features a broad substrate scope, and substrates that are challenging for more conventional ether bond forming processes may be coupled. TMS=trimethylsilyl.

    4. Borenium Cations

      A Stable but Highly Reactive Phosphine-Coordinated Borenium: Metal-free Dihydrogen Activation and Alkyne 1,2-Carboboration

      Dr. Marc Devillard, Dr. Rémy Brousses, Dr. Karinne Miqueu, Dr. Ghenwa Bouhadir and Dr. Didier Bourissou

      Article first published online: 20 MAR 2015 | DOI: 10.1002/anie.201500959

      Thumbnail image of graphical abstract

      Versatile reactivity: A new type of borenium cation is reported in which a naphthyl bridge supports a strong P[RIGHTWARDS ARROW]B interaction. Borenium reacts with H2 through side-on coordination of H2 to boron, heterolytic splitting, and concomitant cleavage of the B[BOND]Mes bond. The molecule also reacts with 3-hexyne through a syn 1,2-carboboration reaction. NTf2=triflimide.

    5. Peptidomimetics | Hot Paper

      Controlling the Origins of Inflammation with a Photoactive Lipopeptide Immunopotentiator

      Dr. Rock J. Mancini, Lalisa Stutts, Dr. Troy Moore and Prof. Aaron P. Esser-Kahn

      Article first published online: 20 MAR 2015 | DOI: 10.1002/anie.201500416

      Thumbnail image of graphical abstract

      The origin of inflammation in cell culture is commonly obscured by paracrine and autocrine signaling. A small-molecule immunopotentiator was developed that tags cells and initiates inflammation of the tagged cells using light. BMDCs=bone-marrow-derived dendritic cells, TNF=tumor necrosis factor.

    6. Nanoparticles

      Mannose-6-Phosphate Receptor: A Target for Theranostics of Prostate Cancer

      Dr. Ophélie Vaillant, Dr. Khaled El Cheikh, Dr. David Warther, Dr. David Brevet, Dr. Marie Maynadier, Dr. Elise Bouffard, Dr. Frédéric Salgues, Dr. Audrey Jeanjean, Dr. Pierre Puche, Dr. Catherine Mazerolles, Dr. Philippe Maillard, Dr. Olivier Mongin, Dr. Mireille Blanchard-Desce, Dr. Laurence Raehm, Dr. Xavier Rébillard, Dr. Jean-Olivier Durand, Dr. Magali Gary-Bobo, Dr. Alain Morère and Dr. Marcel Garcia

      Article first published online: 20 MAR 2015 | DOI: 10.1002/anie.201500286

      Thumbnail image of graphical abstract

      On target: The over-expression of a mannose-6-phosphate receptor was demonstrated in prostate tissues and cancer cell lines. This receptor was targeted with a mannose-6-phosphate analogue grafted onto the surface of mesoporous silica nanoparticles (MSNs). MSNs were efficient for cancer imaging and therapy, thus demonstrating the potential of M6PR targeting for prostate cancer theranostics.

    7. Hydrides

      Air-Stable (CAAC)CuCl and (CAAC)CuBH4 Complexes as Catalysts for the Hydrolytic Dehydrogenation of BH3NH3

      Dr. Xingbang Hu, Dr. Michèle Soleilhavoup, Dr. Mohand Melaimi, Dr. Jiaxiang Chu and Prof. Guy Bertrand

      Article first published online: 20 MAR 2015 | DOI: 10.1002/anie.201500224

      Thumbnail image of graphical abstract

      Copper works! [(CAAC)CuCl] reacts with both NaBH4 and BH3NH3 to afford [(CAAC)CuBH4] as a thermally and air-stable complex. Both complexes efficiently promote the hydrolytic dehydrogenation of ammonia borane at room temperature, with a turnover frequency of up to 8400 molinline image molcat−1 h−1. In addition, these air-stable catalysts are readily recyclable. CAAC=cyclic (alkyl)(amino)carbene.

  25. Minireviews

    1. Olefin Cross Metathesis

      Z-Selective Cross Metathesis with Ruthenium Catalysts: Synthetic Applications and Mechanistic Implications

      Dr. Myles B. Herbert and Prof. Dr. Robert H. Grubbs

      Article first published online: 20 MAR 2015 | DOI: 10.1002/anie.201411588

      Thumbnail image of graphical abstract

      Zo Zelective: After the initial discovery that ruthenium alkylidene catalysts with cyclometalated NHC ligands could enable the Z-selective homodimerization of terminal olefins, research into forming more complex products containing internal Z-double bonds has moved at a fast pace. This Minireview serves as a guide for the use of these catalysts and similarly powerful Z-selective ruthenium catalysts for the formation of complex cross products with Z-olefins.

  26. Author Profiles

    1. Shi Zhang Qiao

      Article first published online: 18 MAR 2015 | DOI: 10.1002/anie.201500725

      Thumbnail image of graphical abstract

      My favorite painter is Jan Vermeer. The most important thing I learned from my students is self-motivation.

  27. Communications

    1. Optogenetic Therapy

      A Synthetic Erectile Optogenetic Stimulator Enabling Blue-Light-Inducible Penile Erection

      Taeuk Kim, Marc Folcher, Marie Doaud-El Baba and Prof. Martin Fussenegger

      Article first published online: 18 MAR 2015 | DOI: 10.1002/anie.201412204

      Thumbnail image of graphical abstract

      A bolt from the blue: A synthetic designer guanylate cyclase producing a blue-light-inducible surge of the second messenger cyclic guanosine monophosphate (cGMP) in mammalian cells was used as an erectile optogenetic stimulator (EROS). Blue-light-dependent penile erection associated with occasional ejaculation was triggered in male rats by simple illumination of EROS-transfected corpus cavernosum with a portable commercial light-therapy device.

    2. Electrochemistry

      Formulation of Ionic-Liquid Electrolyte to Expand the Voltage Window of Supercapacitors

      Katherine L. Van Aken, Dr. Majid Beidaghi and Prof. Yury Gogotsi

      Article first published online: 18 MAR 2015 | DOI: 10.1002/anie.201412257

      Thumbnail image of graphical abstract

      Asymmetric behavior: Using model electrochemical cells based on two identical onion-like carbon electrodes and two different ionic-liquid electrolytes and their mixtures, it was shown that the asymmetric behavior of the electrolyte cation and anion toward the two electrodes (see picture) limits the operating potential window of the cell and therefore its energy density.

  28. Cover Pictures

    1. Hypercrosslinked Phenolic Polymers with Well-Developed Mesoporous Frameworks

      Dr. Jinshui Zhang, Dr. Zhen-An Qiao, Dr. Shannon M. Mahurin, Dr. Xueguang Jiang, Dr. Song-Hai Chai, Dr. Hanfeng Lu, Kimberly Nelson and Prof. Sheng Dai

      Article first published online: 18 MAR 2015 | DOI: 10.1002/anie.201502271

      Thumbnail image of graphical abstract

      A hierarchical porous framework with interconnected micro- and mesopores (analogous to a tree root system) has a unique structural advantage for carbon capture. The larger mesopores can substantially increase the accessibility of the micropores to guest molecules through enhanced diffusion. In their Communication (DOI: 10.1002/anie.201500305), S. Dai and co-workers introduce a soft-chemistry synthetic strategy based on a Friedel—Crafts alkylation for the creation of such porous phenolic polymers.

    2. A Facile and Versatile Approach to Double N-Heterohelicenes: Tandem Oxidative C[BOND]N Couplings of N-Heteroacenes via Cruciform Dimers

      Dr. Daisuke Sakamaki, Daisuke Kumano, Prof. Dr. Eiji Yashima and Prof. Dr. Shu Seki

      Article first published online: 18 MAR 2015 | DOI: 10.1002/anie.201502273

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      Double N-hetero[5]helicenes that consist of two nitrogen-substituted heteropentacenes were synthesized by tandem oxidative C[BOND]N couplings via the cruciform dimers. In their Communication (DOI: 10.1002/anie.201500684), D. Sakamaki, S. Seki, and co-workers describe the synthesis, structures, and electronic properties of these novel compounds, which are remarkably stable towards racemization.

    3. Synthesis of Carbon/Sulfur Nanolaminates by Electrochemical Extraction of Titanium from Ti2SC

      Dr. Meng-Qiang Zhao, Morgane Sedran, Zheng Ling, Maria R. Lukatskaya, Olha Mashtalir, Michael Ghidiu, Boris Dyatkin, Darin J. Tallman, Prof. Thierry Djenizian, Prof. Michel W. Barsoum and Prof. Yury Gogotsi

      Article first published online: 18 MAR 2015 | DOI: 10.1002/anie.201502316

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      An electrochemical method has been developed to selectively extract Ti from the MAX phase Ti2SC to give C/S nanolaminates composed predominantly of amorphous and some graphene-like nanoflakes. In their Communication (DOI: 10.1002/anie.201500110), Y. Gogotsi et al. demonstrate the C/S nanolaminates to be promising cathode candidates for Li/S batteries. They also show that it is possible to electrochemically selectively extract Ti from a number of other MAX phases to create a new class of “AX” phases, most of which should be nanolayered.

  29. Communications

    1. Synthetic Methods

      Well-Defined Copper(I) Fluoroalkoxide Complexes for Trifluoroethoxylation of Aryl and Heteroaryl Bromides

      Ronglu Huang, Yangjie Huang, Xiaoxi Lin, Mingguang Rong and Prof. Dr. Zhiqiang Weng

      Article first published online: 17 MAR 2015 | DOI: 10.1002/anie.201501257

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      Efficiency drive: A series of copper(I) fluoroalkoxide complexes bearing N,N ligands have been prepared and structurally characterized. These well-defined complexes serve as efficient reagents for the fluoroalkoxylation of aryl and heteroaryl bromides to produce a wide range of trifluoroethyl, pentafluoropropyl, and tetrafluoropropyl (hetero)aryl ethers in good to excellent yields.

    2. Electrochemistry | Very Important Paper

      Improving the Electrochemical Performance of the Li4Ti5O12 Electrode in a Rechargeable Magnesium Battery by Lithium–Magnesium Co-Intercalation

      Na Wu, Zhen-Zhong Yang, Hu-Rong Yao, Dr. Ya-Xia Yin, Prof. Lin Gu and Prof. Yu-Guo Guo

      Article first published online: 17 MAR 2015 | DOI: 10.1002/anie.201501005

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      Synergy between Mg2+ and Li+ ions: By controlling the collaborative electrochemistry of magnesium and lithium cations, Li4Ti5O12 electrodes (LTO; see picture) close to sub-micron size gain extraordinary electrochemical energy storage capability. The electrodes show improved kinetics in rechargeable magnesium batteries.

    3. Core–Shell Nanostructures

      Synthesis of Ultrathin Face-Centered-Cubic Au@Pt and Au@Pd Core–Shell Nanoplates from Hexagonal-Close-Packed Au Square Sheets

      Zhanxi Fan, Yihan Zhu, Dr. Xiao Huang, Prof. Yu Han, Qingxiao Wang, Dr. Qing Liu, Ying Huang, Prof. Chee Lip Gan and Prof. Hua Zhang

      Article first published online: 17 MAR 2015 | DOI: 10.1002/anie.201500993

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      Phase change: Ultrathin Au@Pt and Au@Pd core–shell nanoplates were prepared from Au square sheets. A phase transformation from hexagonal close-packed (hcp) to face-centered cubic (fcc) is observed upon coating the hcp Au square sheets with Pt or Pd under ambient conditions. The prepared fcc Au@Pt and Au@Pd rhombic nanoplates demonstrate unique (101)f orientation (picture shows a typical fcc Au@Pt rhombic nanoplate).

    4. Photochemistry

      Regioselective Chromatic Orthogonality with Light-Activated Metathesis Catalysts

      Efrat Levin, Dr. Sudheendran Mavila, Or Eivgi, Dr. Eyal Tzur and Prof. N. Gabriel Lemcoff

      Article first published online: 17 MAR 2015 | DOI: 10.1002/anie.201500740

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      A guiding light: By the combination of a light-activated sulfur-chelated olefin-metathesis catalyst with a photocleavable bulky silyl protecting group, two orthogonal pathways enabled the selective synthesis of five- or six-membered heterocycles according to the order in which the starting material was irradiated with light of different wavelengths. Thus, protecting-group removal and metathesis gave either a dihydropyran or a dihydrofuran.

    5. Cascade Reactions

      Synthesis of Cyclopropyl-Substituted Furans by Brønsted Acid Promoted Cascade Reactions

      Prof. Dr. J. Stephen Clark, Filippo Romiti, Kirsten F. Hogg, Dr. Malai Haniti S. A. Hamid, Sven C. Richter, Dr. Alistair Boyer, Joanna C. Redman and Dr. Louis J. Farrugia

      Article first published online: 17 MAR 2015 | DOI: 10.1002/anie.201500625

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      Chloroacetic acid promotes an efficient and diastereoselective intramolecular cascade reaction of electron-deficient ynenones to deliver products featuring a 2,3,5-trisubstituted furan bearing a fused cyclopropyl substituent at the 5-position. Synthetically relevant polycyclic building blocks featuring rings of various sizes and heteroatoms have been synthesized in high yield using this mild acid-catalyzed reaction.

    6. Hypervalent Compounds

      Tandem Catalytic C(sp3)[BOND]H Amination/Sila-Sonogashira–Hagihara Coupling Reactions with Iodine Reagents

      Dr. Julien Buendia, Dr. Benjamin Darses and Dr. Philippe Dauban

      Article first published online: 17 MAR 2015 | DOI: 10.1002/anie.201412364

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      I(003) is a double agent: A tandem C[BOND]N and C[BOND]C bond-forming reaction has been achieved through RhII/Pd0 catalysis. The sequence first involves an iodine(III) oxidant, then the in situ generated iodine(I) by-product is used as a coupling partner. The overall process affords complex building blocks with high yields, and demonstrates the synthetic value of iodoarenes produced in trivalent iodine reagent mediated oxidations.

    7. Cyclic Peptides

      Intracellular Delivery of Peptidyl Ligands by Reversible Cyclization: Discovery of a PDZ Domain Inhibitor that Rescues CFTR Activity

      Dr. Ziqing Qian, Dr. Xiaohua Xu, Dr. Jeanine F. Amacher, Prof. Dr. Dean R. Madden, Prof. Dr. Estelle Cormet-Boyaka and Prof. Dr. Dehua Pei

      Article first published online: 17 MAR 2015 | DOI: 10.1002/anie.201411594

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      Roll in, unroll: Peptide cargoes were fused to cell-penetrating peptides (CPPs) and cyclized through a disulfide bond. This cyclization increases their proteolytic stability and cell permeability. Once they enter the cell, the disulfide bond is reduced by intracellular thiols, thus leading to regeneration of the functional linear peptides.

    8. C[BOND]C Coupling | Very Important Paper

      Direct C(sp2)[BOND]C(sp3) Cross-Coupling of Diaryl Zinc Reagents with Benzylic, Primary, Secondary, and Tertiary Alkyl Halides

      Dr. Jay J. Dunsford, Dr. Ewan R. Clark and Dr. Michael J. Ingleson

      Article first published online: 17 MAR 2015 | DOI: 10.1002/anie.201411403

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      Zinc and you’ll miss it! Direct C(sp2)[BOND]C(sp3) cross-coupling of diaryl zinc reagents with alkyl halides proceeded rapidly at ambient temperature without a coordinating ethereal solvent or an added catalyst (see scheme). This versatile, operationally simple approach to C(sp2)[BOND]C(sp3) bond formation enables the expedient construction of a diverse array of carbon-based structural motifs.

    9. Palladium Complexes

      Characterization of a Palladium Dihydrogen Complex

      Samantha J. Connelly, Andrew G. Chanez, Prof. Werner Kaminsky and Prof. D. Michael Heinekey

      Article first published online: 17 MAR 2015 | DOI: 10.1002/anie.201412076

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      Palladium binds H2: The first dihydrogen complex of palladium has been synthesized and characterized, employing a tBuPCP (κ3-2,6-(tBu2PCH2)2C6H3) pincer ligand. The complex is investigated by X-ray crystallography and NMR spectroscopy, which reveals a very short H[BOND]H bond length.

    10. Protein Analysis

      You have full text access to this OnlineOpen article
      Secondary-Ion Mass Spectrometry of Genetically Encoded Targets

      Ingrid C. Vreja, Selda Kabatas, Dr. Sinem K. Saka, Katharina Kröhnert, Dr. Carmen Höschen, Dr. Felipe Opazo, Prof. Dr. Ulf Diederichsen and Prof. Dr. Silvio O. Rizzoli

      Article first published online: 17 MAR 2015 | DOI: 10.1002/anie.201411692

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      SPILLing the beans: a method of labeling specific proteins for secondary-ion mass spectrometry (SIMS), termed SPILL (specific protein isotopic and fluorescence labeling) is developed which involves unnatural amino acid incorporation and click reaction with a fluorescent probe enriched in 19F (see scheme). The applicability of this method extends from cell culture systems to invertebrate model organisms.

    11. Antigens | Hot Paper

      Bioorthogonal Deprotection on the Dendritic Cell Surface for Chemical Control of Antigen Cross-Presentation

      Joanna B. Pawlak, Geoffroy P. P. Gential, Dr. Tracy J. Ruckwardt, Jessica S. Bremmers, Nico J. Meeuwenoord, Prof. Ferry A. Ossendorp, Prof. Herman S. Overkleeft, Dr. Dmitri V. Filippov and Dr. Sander I. van Kasteren

      Article first published online: 17 MAR 2015 | DOI: 10.1002/anie.201500301

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      Antigen cross-presentation is the uptake of exogenous antigens followed by processing in the MHC-I complex, which is normally reserved for endogenous antigens. This process may now be studied by using masked epitopes: Azides are exploited as bioorthogonal protecting groups to generate antigens that are not recognized by their cognate T-cell unless they are deprotected using an on-cell Staudinger reduction.

    12. Catalytic Thiolation | Hot Paper

      Heterogeneously Catalyzed Direct C[BOND]H Thiolation of Heteroarenes

      Suhelen Vásquez-Céspedes, Dr. Angélique Ferry, Dr. Lisa Candish and Prof. Dr. Frank Glorius

      Article first published online: 17 MAR 2015 | DOI: 10.1002/anie.201411997

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      (Hetero)genius: A general method for the direct thiolation of electron-rich heteroarenes was developed by employing Pd/Al2O3, a recoverable and commercially available heterogeneous catalyst, and CuCl2. Preliminary mechanistic studies indicate a heterogeneous active catalytic species, with the two metals playing complementary roles in the formation of the thiolated products.

    13. Supramolecular Chemistry

      Mixing Biomimetic Heterodimers of Nucleopeptides to Generate Biocompatible and Biostable Supramolecular Hydrogels

      Dan Yuan, Xuewen Du, Junfeng Shi, Ning Zhou, Jie Zhou and Prof. Dr. Bing Xu

      Article first published online: 17 MAR 2015 | DOI: 10.1002/anie.201412448

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      Just mix it! The simple mixing of heterodimers of nucleopeptides provides a facile approach to generate biostable and biocompatible supramolecular hydrogels as soft biomaterials.

    14. Zeolites

      Fabrication of b-Oriented MFI Zeolite Films under Neutral Conditions without the Use of Hydrogen Fluoride

      Dr. Yong Peng, Xiaofei Lu, Prof. Dr. Zhengbao Wang and Prof. Dr. Yushan Yan

      Article first published online: 17 MAR 2015 | DOI: 10.1002/anie.201412482

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      In one direction: Highly b-oriented MFI zeolite films have been successfully prepared for the first time under neutral conditions without the use of hydrogen fluoride. The Na2O species dissolved from the glass plate support or a trace amount of NaOH facilitates the secondary growth of MFI seed crystals.

    15. Synthetic Methods

      Highly Regio- and Stereoselective Hydrosilylation of Internal Thioalkynes under Mild Conditions

      Shengtao Ding, Li-Juan Song, Yong Wang, Prof. Xinhao Zhang, Prof. Lung Wa Chung, Prof. Yun-Dong Wu and Prof. Jianwei Sun

      Article first published online: 17 MAR 2015 | DOI: 10.1002/anie.201500372

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      A rich source of vinyl silanes: A general, mild, and highly stereoselective hydrosilylation of electron-rich alkynes gave a range of stereodefined multisubstituted vinyl silanes with high efficiency (see scheme; R1, R2=alkyl, aryl; TMS=trimethylsilyl). Unprecedented syn selectivity was observed with the cationic catalyst [Cp*Ru(MeCN)3]+. DFT calculations provided important insight into the mechanism.

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