Angewandte Chemie International Edition

Cover image for Vol. 53 Issue 17

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, Zeitschrift für Chemie

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April 23, 2014

VIP: Efficient Synthesis of THP/THF-Containing Macrolides by Palladium-Catalyzed Alkoxycarbonylative Macrolactonizations

Yu Bai, Dexter C. Davis, and Mingji Dai*

A novel Pd-catalyzed cascade alkoxycarbonylative macrolactonization to construct tetrahydropyran/tetrahydrofuran- (THP/THF-) containing bridged macrolactones in one step from alkendiols is described. Products with various ring sizes and substituents were obtained. Challenging macrolactones involving tertiary alcohols were synthesized smoothly as well. Mechanistically, experimental evidence to support a trans-oxypalladation step has been provided. The method was applied to the synthesis of potent anticancer 9-demethylneopeltolide.

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April 22, 2014

VIP: Harnessing Quinone Methides: Total Synthesis of (+/-)-Vaticanol A

Tue H. Jepsen, Stephen B. Thomas, Yunqing Lin, Christos I. Stathakis, Irene de Miguel, and Scott A. Snyder*

The resveratrol trimer vaticanol A, along with a number of diastereomeric congeners, has been synthesized for the first time through an effective strategy using three reactive quinone methide intermediates to forge three critical bonds. These events, one of which succeeded only under very specific conditions, expediently generated its [7,5]-carbocyclic core and afforded a unique sequence for dihydrobenzofuran formation.

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April 22, 2014

VIP: A Novel Vanadosilicate with Hexadeca-Coordinated Cs+ as a Highly Effective Cs+ Remover

Shuvo Jit Datta, Won Kyung Moon, Do Young Choi, In Chul Hwang, and Kyung Byung Yoon*

The effective removal of 137Cs+ from the contaminated groundwater and seawater and from the radioactive nuclear waste solutions is an important issue. A novel microporous vanadosilicate shows an excellent Cs+-capturing and immobilizing properties from the groundwater, seawater, and nuclear waste solution. This material greatly excels compared to other known materials in terms of selectivity, capacity, and kinetics, in particular, at very low Cs+ concentrations, distinguishing itself as the best material for the removal of radioactive Cs+ under the given test conditions. The novel vanadosilicate also contains hexadeca-coordinated Cs+, which is the highest coordination number ever observed.

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April 22, 2014

VIP: Unlock the N2-Selectivity of Benzotriazoles: Regiodivergent and Highly Selective Coupling of Benzotriazoles with Allenes

Kun Xu, Niels Thieme, and Bernhard Breit*

Rhodium-catalyzed, highly N2- and N1-selective coupling of benzotriazoles with allenes are reported. The exceptionally high N2 and N1 selectivities were achieved applying a rhodium(I)/DPEphos and rhodium(I)/JoSPOphos catalyst, respectively. This method permits the atom-economic synthesis of valuable branched N2 and N1-allylated benzotriazole derivatives and makes possible preliminary studies of their reactivity.



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April 22, 2014

Hot Paper: Highly Active Electrocatalysis of the Hydrogen Evolution Reaction by Cobalt Phosphide Nanoparticles

Hot Paper: Highly Active Electrocatalysis of the Hydrogen Evolution Reaction by Cobalt Phosphide Nanoparticles

Eric J. Popczun, Carlos G. Read, Christopher W. Roske, Nathan S. Lewis*, Raymond E. Schaak*

One step closer to Pt: Nanoparticles of cobalt phosphide (CoP) catalyze the hydrogen evolution reaction with high activity and stability under strongly acidic conditions. Its electrocatalytic performance places CoP amongst the best Earth-abundant alternatives to platinum.

Published online, DOI: 10.1002/anie.201402646 – Read now

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April 21, 2014

Hot Paper: Gold-Catalyzed Synthesis of Functionalized Pyridines by Using 2H-Azirines as Synthetic Equivalents of Alkenyl Nitrenes

Hot Paper: Gold-Catalyzed Synthesis of Functionalized Pyridines by Using 2H-Azirines as Synthetic Equivalents of Alkenyl Nitrenes

Agnes Prechter, Guilhem Henrion, Pierre Faudot dit Bel, Fabien Gagosz*

Ringing the changes: A series of easily accessible 2-propargyl 2H-azirine derivatives were efficiently converted into the corresponding functionalized pyridines in the presence of a gold catalyst. This transformation, which exhibits a high functional-group tolerance and a wide substrate scope, corresponds to the formal intramolecular transfer of an alkenyl nitrene to an alkyne.

Published online, DOI: 10.1002/anie.201402470 – Read now

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April 20, 2014

Hot Paper: Organocatalytic Atroposelective Aldol Condensation: Synthesis of Axially Chiral Biaryls by Arene Formation

Hot Paper: Organocatalytic Atroposelective Aldol Condensation: Synthesis of Axially Chiral Biaryls by Arene Formation

Achim Link, Christof Sparr*

Head-turning! An organocatalytic atroposelective aldol condensation to tri-ortho-substituted biaryls is described. Key to the process is an efficient transfer of the stereochemical information of a secondary amine catalyst into the axis of chirality of binaphthyl products. The reaction proceeds analogous to the aromatic polyketide biosynthesis and is distinct in its initiation by virtue of dienamine formation. This method allows for the synthesis of axially chiral biaryls with remarkable atroposelectivity of up to e.r. 99:1.

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April 20, 2014

Hot Paper: Palladium-Catalyzed C(sp3)–H Activation: A Facile Method for the Synthesis of 3,4-Dihydroquinolinone Derivatives

Hot Paper: Palladium-Catalyzed C(sp3)–H Activation: A Facile Method for the Synthesis of 3,4-Dihydroquinolinone Derivatives

Jia-Xuan Yan, Hu Li, Xiang-Wei Liu, Jiang-Ling Shi, Xin Wang, Zhang-Jie Shi*

3,4-Dihydroquinolinones were synthesized by the palladium-catalyzed, oxidative-addition-initiated activation and arylation of inert C(sp3)–H bonds. Pd(OAc)2 and P(o-tol)3 were used as the catalyst and ligand, respectively, to improve the efficiency of the reaction. A further advantage of this reaction is that it could be performed in air.

Published online, DOI: 10.1002/anie.201402562 – Read now

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April 19, 2014

Hot Paper: Stabilization of Catalytically Active Cu+ Surface Sites on Titanium–Copper Mixed-Oxide Films

Hot Paper: Stabilization of Catalytically Active Cu+ Surface Sites on Titanium–Copper Mixed-Oxide Films

Ashleigh E. Baber, Xiaofang Yang, Hyun You Kim, Kumudu Mudiyanselage, Markus Soldemo, Jonas Weissenrieder, Sanjaya D. Senanayake, Abdullah Al-Mahboob, Jerzy T. Sadowski, Jaime Evans, José A. Rodriguez, Ping Liu, Friedrich M. Hoffmann, Jingguang G. Chen, Darío J. Stacchiola*

Positively active: Copper oxide based structures were the first that could catalyze the oxidation of CO at room temperature. Their deactivation, however, is facile, because the required Cu+ state cannot be preserved under the reaction conditions. The addition of the right amount of titanium leads to mixed CuTiOx films that are thermally and chemically stable and more active CO oxidation catalysts than pure copper oxide materials.

Published online, DOI: 10.1002/anie.201402435 – Read now

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April 19, 2014

Hot Paper: Design of Monodisperse and Well-Defined Polypeptide-Based Polyvalent Inhibitors of Anthrax Toxin

Hot Paper: Design of Monodisperse and Well-Defined Polypeptide-Based Polyvalent Inhibitors of Anthrax Toxin

Sanket Patke, Mohan Boggara, Ronak Maheshwari, Sunit K. Srivastava, Manish Arha, Marc Douaisi, Jacob T. Martin, Ian B. Harvey, Matthew Brier, Tania Rosen, Jeremy Mogridge, Ravi S. Kane*

Quantity and spacing: A protein-engineering approach was designed to develop monodisperse polyvalent molecules based on tandem-repeat polypeptide scaffolds. This approach allowed for precise control over ligand spacing and valency of the polyvalent molecules. This approach was applied to develop potent inhibitors of anthrax lethal toxin.

Published online, DOI: 10.1002/anie.201400870 – Read now

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April 18, 2014

Hot Paper: Flow-Through Synthesis on Teflon-Patterned Paper To Produce Peptide Arrays for Cell-Based Assays

Hot Paper: Flow-Through Synthesis on Teflon-Patterned Paper To Produce Peptide Arrays for Cell-Based Assays

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

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.

Published online, DOI: 10.1002/anie.201402037 – Read now

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April 18, 2014

Hot Paper: A Shape-Persistent Quadruply Interlocked Giant Cage Catenane with Two Distinct Pores in the Solid State

Hot Paper: A Shape-Persistent Quadruply Interlocked Giant Cage Catenane with Two Distinct Pores in the Solid State

Gang Zhang, Oliver Presly, Fraser White, Iris M. Oppel, Michael Mastalerz*

Two is better than one: During the crystallization of a giant shape-persistent organic cage compound, a dimeric catenated structure is formed by a 96-fold condensation reaction of 40 molecular subunits. The crystals of the molecular catenane contain one intrinsic mesopore (2.0 nm) and one extrinsic micropore (1.3 nm).

Published online, DOI: 10.1002/anie.201400285 – Read now

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April 23, 2014
VIP: Efficient Synthesis of THP/THF-Containing Macrolides by Palladium-Catalyzed Alkoxycarbonylative Macrolactonizations

April 22, 2014
VIP: Harnessing Quinone Methides: Total Synthesis of (+/-)-Vaticanol A

April 22, 2014
VIP: A Novel Vanadosilicate with Hexadeca-Coordinated Cs+ as a Highly Effective Cs+ Remover

April 22, 2014
VIP: Unlock the N2-Selectivity of Benzotriazoles: Regiodivergent and Highly Selective Coupling of Benzotriazoles with Allenes

April 22, 2014
Hot Paper: Highly Active Electrocatalysis of the Hydrogen Evolution Reaction by Cobalt Phosphide Nanoparticles

April 21, 2014
Hot Paper: Gold-Catalyzed Synthesis of Functionalized Pyridines by Using 2H-Azirines as Synthetic Equivalents of Alkenyl Nitrenes

April 20, 2014
Hot Paper: Organocatalytic Atroposelective Aldol Condensation: Synthesis of Axially Chiral Biaryls by Arene Formation

April 20, 2014
Hot Paper: Palladium-Catalyzed C(sp3)–H Activation: A Facile Method for the Synthesis of 3,4-Dihydroquinolinone Derivatives

April 19, 2014
Hot Paper: Stabilization of Catalytically Active Cu+ Surface Sites on Titanium–Copper Mixed-Oxide Films

April 19, 2014
Hot Paper: Design of Monodisperse and Well-Defined Polypeptide-Based Polyvalent Inhibitors of Anthrax Toxin

April 18, 2014
Hot Paper: Flow-Through Synthesis on Teflon-Patterned Paper To Produce Peptide Arrays for Cell-Based Assays

April 18, 2014
Hot Paper: A Shape-Persistent Quadruply Interlocked Giant Cage Catenane with Two Distinct Pores in the Solid State

April 17, 2014
Hot Paper: Co-existence of Two Different α-Synuclein Oligomers with Different Core Structures Determined by Hydrogen/Deuterium Exchange Mass Spectrometry

April 17, 2014
Hot Paper: A Molecular Approach to Self-Supported Cobalt-Substituted ZnO Materials as Remarkably Stable Electrocatalysts for Water Oxidation

April 16, 2014
VIP: Decay of FeV Nitride Complexes by a N–N Bond Coupling Reaction in Solution: A Combined Spectroscopic and Theoretical Analysis

April 16, 2014
Hot Paper: Engineering Multifunctional Capsules through the Assembly of Metal–Phenolic Networks

April 15, 2014
Angewandte Chemie 16/2014: Straight to Your Heart

April 15, 2014
Hot Paper: Geminate Recombination as a Photoprotection Mechanism for Fluorescent Dyes

April 15, 2014
VIP: Copper-Chelating Azides for Efficient Click Conjugations in Complex Media

April 09, 2014
Hot Paper: High-Quality Three-Dimensional Nanoporous Graphene

April 08, 2014
Hot Paper: Construction of Quaternary Stereogenic Carbon Centers through Copper-Catalyzed Enantioselective Allylic Cross-Coupling with Alkylboranes

April 07, 2014
Hot Paper: Constructing 3D Branched Nanowire Coated Macroporous Metal Oxide Electrodes with Homogeneous or Heterogeneous Compositions for Efficient Solar Cells

April 06, 2014
Hot Paper: Controlled Electropolymerization of Ruthenium(II) Vinylbipyridyl Complexes in Mesoporous Nanoparticle Films of TiO2

April 05, 2014
Hot Paper: Arylphosphonylation and Arylazidation of Activated Alkenes

April 04, 2014
Hot Paper: Gold-Catalyzed Intermolecular C–S Bond Formation: Efficient Synthesis of α-Substituted Vinyl Sulfones

April 03, 2014
Angewandte Chemie 15/2014: New Pathways

April 01, 2014
Hot Paper: Fusing N-Heterocyclic Carbenes with Carborane Anions

March 31, 2014
Hot Paper: Bidirectional Regulation of mRNA Translation in Mammalian Cells by Using PUF Domains

March 30, 2014
Hot Paper: Structure of a Reactive Gold Carbenoid

March 29, 2014
Hot Paper: Single Crystals Popping Under UV Light: A Photosalient Effect Triggered by a [2+2] Cycloaddition Reaction

March 28, 2014
Angewandte Chemie 14/2014: Can You Do Without?

March 28, 2014
Hot Paper: Late-Stage Functionalization of Biologically Active Heterocycles Through Photoredox Catalysis

March 27, 2014
Hot Paper: Metal-Free Photochemical Aromatic Perfluoroalkylation of α-Cyano Arylacetates

March 25, 2014
VIP: Sequential Intra-Intercellular Nanoparticle Delivery System for Deep Tumor Penetration

March 25, 2014
Hot Paper: Amide Synthesis by Nucleophilic Attack of Vinyl Azides

March 24, 2014
Hot Paper: An Integrated Photoelectrochemical–Chemical Loop for Solar-Driven Overall Splitting of Hydrogen Sulfide

March 23, 2014
Hot Paper: A New Pathway of DNA G-Quadruplex Formation

March 22, 2014
Hot Paper: A Facile Synthesis of Dynamic, Shape-Changing Polymer Particles

March 21, 2014
Hot Paper: A Trinuclear Pd3O2 Intermediate in Aerobic Oxidation Catalysis

March 20, 2014
Hot Paper: Selective Janus Particle Assembly at Tipping Points of Thermally-Switched Wetting

March 19, 2014
VIP: Threshold Sensing by a Synthetic Enzymatic Reaction–Diffusion Network

March 16, 2014
Hot Paper: Total Chemical Synthesis of the Enzyme Sortase AΔN59 with Full Catalytic Activity

March 15, 2014
Hot Paper: A Simple 3,4-Ethylenedioxythiophene Based Hole-Transporting Material for Perovskite Solar Cells

March 14, 2014
VIP: Towards a Sustainable Synthesis of Formate Salts: Combined Catalytic Methanol Dehydrogenation and Bicarbonate Hydrogenation

March 14, 2014
VIP: Structure of Transient Amyloid-β Oligomers Differs From Less Toxic Fibrils in Regions Known to Harbor Familial Alzheimer Mutations

March 14, 2014
Hot Paper: Peapod-Type Nanocomposites through the In Situ Growth of Gold Nanoparticles within Preformed Hexaniobate Nanoscrolls

March 13, 2014
Hot Paper: Functionalizing Single Crystals: Incorporation of Nanoparticles Inside Gel-Grown Calcite Crystals

March 12, 2014
Hot Paper: Rhodium Enalcarbenoids: Direct Synthesis of Indoles by Rhodium(II)-Catalyzed [4+2] Benzannulation of Pyrroles

March 10, 2014
VIP: How Does a Coordinated Radical Ligand Affect the Spin Crossover Properties in an Octahedral Iron(II) Complex?

March 10, 2014
Hot Paper: A Brønsted Acid Catalyzed Redox Arylation

March 07, 2014
VIP: The Compressibility of pH-Sensitive Microgels at the Oil–Water Interface: Higher Charge Leads to Less Repulsion

March 06, 2014
VIP: Chemoselective Intermolecular α-Arylation of Amides

March 05, 2014
VIP: Rate Coefficients of Criegee Intermediate (CH2OO and CH3CHOO) Reactions with Formic and Acetic Acid Are Close to Their Collision Limit: Direct Kinetics Measurements and Atmospheric Implications

March 05, 2014
Hot Paper: All Organic Sodium-Ion Batteries with Na4C8H2O6

March 04, 2014
Hot Paper: The Formation and Self-Assembly of Long Prebiotic Oligomers Produced by the Condensation of Unactivated Amino Acids on Oxide Surfaces

March 03, 2014
VIP: Synthesis of Tris- and Tetrakis(pentafluoroethyl)silanes

February 28, 2014
VIP: An Efficient and Modular Route to Sequence-Defined Polymers Appended to DNA

February 26, 2014
Hot Paper: Carbon Nanotubes/Heteroatom-Doped Carbon Core–Sheath Nanostructures as Highly Active, Metal-Free Oxygen Reduction Electrocatalysts for Alkaline Fuel Cells

February 26, 2014
VIP: Confirmed by X-ray Crystallography: The B·B One-Electron σ Bond

February 25, 2014
VIP: In Vivo Liver Cancer Chemoembolization and Magnetic Resonance Imaging Using Iron Oxide Nanoshell/Doxorubicin/Poly(vinyl alcohol) Hybrid Composites

February 24, 2014
VIP: A Volatile Lactone of Hymenoscyphus Pseudoalbidus, Pathogen of European Ash Dieback, Inhibits Host Germination

February 24, 2014
VIP: Metal- and Reagent-Free Highly Selective Anodic Cross-Coupling Reaction of Phenols

February 24, 2014
VIP: Mechanically Driven Activation of Polyaniline into Its Conductive Form

February 24, 2014
VIP: Probing Transient Conformational States of Proteins by Solid-State R Relaxation-Dispersion NMR Spectroscopy

February 24, 2014
VIP: Merging Aerobic Oxidation and Enamine Catalysis in Asymmetric α-Amination of β-Ketocarbonyls Using N-Hydroxycarbamates as Nitrogen Sources

January 13, 2014
VIP: Total Chemical Synthesis and Biological Activities of Glycosylated and Non-Glycosylated Forms of the Chemokines CCL1 and Ser-CCL1

November 28, 2013
VIP: A Diiron(III,IV) Imido Species Active in Nitrene Transfer Reactions

October 25, 2013
VIP: Recoding the Genetic Code with Selenocysteine

October 25, 2013
VIP: Foldamer-Mediated Remote Stereocontrol: Up to 1,60-Asymmetric Induction

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