Angewandte Chemie International Edition

Cover image for Vol. 54 Issue 28

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

Upcoming VIPs

The following papers are very important in the opinion of two referees.

You are invited to comment on published VIPs. Please use the link given at the end of each such abstract. Scientific comments may be forwarded to the authors by the editorial office and may be posted on this page. Kindly let us know if your comments are for the editorial office only, the author, or the public as well.

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1,3-Butadienyl Dianions as Non-Innocent Ligands: Synthesis and Characterization of Aromatic Dilithio Rhodacycles

Junnian Wei, Yongliang Zhang, Prof. Dr. Wen-Xiong Zhang and Prof. Dr. Zhenfeng Xi

1,3-Butadienyl Dianions as Non-Innocent Ligands: Synthesis and Characterization of Aromatic Dilithio RhodacyclesGive and take: Dilithio reagents that are a type of 1,3-butadienyl dianion react with [{RhCl(cod)}2] to give aromatic dilithio rhodacycles. In this process, the dilithio compounds behave as non-innocent ligands and formal oxidants. Thus organolithium compounds with suitable π conjugation can act as electron acceptors.

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Forming Stereogenic Centers in Acyclic Systems from Alkynes

Dr. Roxane Vabre, M. Sc. Biana Island, B. Sc. Claudia J. Diehl, Prof. Dr. Peter R. Schreiner and Prof. Dr. Ilan Marek

Forming Stereogenic Centers in Acyclic Systems from AlkynesAll-carbon quaternary stereocenter: The combined carbometalation/zinc homologation of alkynes followed by reactions with α-heterosubstituted aldehydes and imines provides access to functionalized acyclic adducts. These adducts obtained in a single-pot reaction have three new carbon–carbon bonds and two to three stereogenic centers, including a quaternary carbon stereocenter.

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Protonation-Dependent Base Flipping at Neutral pH in the Catalytic Triad of a Self-Splicing Bacterial Group II Intron

Dr. Maria Pechlaner, Dr. Daniela Donghi, Dr. Veronika Zelenay and Prof. Dr. Roland K. O. Sigel

Protonation-Dependent Base Flipping at Neutral pH in the Catalytic Triad of a Self-Splicing Bacterial Group II IntronStrongly shifted: Two adenines in the highly conserved and catalytically essential domain 5 of group II introns become protonated near physiological pH values. The associated dynamic equilibria play an important role in group II intron assembly and catalysis.

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Reductive Insertion of Elemental Chalcogens into Boron–Boron Multiple Bonds

Prof. Dr. Holger Braunschweig, Theresa Dellermann, Dr. William C. Ewing, Thomas Kramer, Christoph Schneider and Stefan Ullrich

Reductive Insertion of Elemental Chalcogens into Boron–Boron Multiple BondsBond order determined by reactivity: Polychalcogenido bi- and monocyclic compounds have been synthesized through use of the reducing equivalents stored in the form of boron–boron multiple bonds. The triple bond of the diboryne is capable of initiating six-electron reductions, while the boron–boron double bond of a diborene provides four reducing equivalents.

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Methylamine-Gas Induced Defect-Healing Behavior of CH3NH3PbI3 Thin Films for Perovskite Solar Cells

Dr. Zhongmin Zhou, Zaiwei Wang, Yuanyuan Zhou, Dr. Shuping Pang, Dong Wang, Dr. Hongxia Xu, Dr. Zhihong Liu, Prof. Nitin P. Padture and Dr. Guanglei Cui

Methylamine-Gas Induced Defect-Healing Behavior of CH3NH3PbI3 Thin Films for Perovskite Solar CellsA perovskite smoothie: Treating CH3NH3PbI3 (MAPbI3) perovskite thin films with methylamine gas induces a rapid collapse of the perovskite structure and formation of a liquid phase. Removing the gas causes conversion back into the perovskite structure giving a smooth defect-free film. Using the film in perovskite solar cells enhances their performance.

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A Cell-Permeable ATP Analogue for Kinase-Catalyzed Biotinylation

Ahmed E. Fouda and Mary Kay H. Pflum

A Cell-Permeable ATP Analogue for Kinase-Catalyzed BiotinylationA cell-permeable ATP analogue, ATP–polyamine–biotin (APB), acts as a cosubstrate for kinase-catalyzed biotinylation in cellulo. APB provides a foundation for the development of additional cell-permeable ATP analogues for cell-signaling research.

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Photocontrolled Reversible Conversion of Nanotube and Nanoparticle Mediated by β-Cyclodextrin Dimers

He-Lue Sun, Dr. Yong Chen, Jin Zhao and Prof. Dr. Yu Liu

Photocontrolled Reversible Conversion of Nanotube and Nanoparticle Mediated by β-Cyclodextrin DimersPhotodriven interconversion: A photoswitchable supramolecular nanotube–nanoparticle system was constructed through secondary assembly of self-aggregates of amphiphilic porphyrin derivatives (see picture). These nanoassemblies repeatedly interconvert upon irradiation at 365 and 450 nm.

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Selective Photooxidation of a Mustard-Gas Simulant Catalyzed by a Porphyrinic Metal–Organic Framework

Dr. Yangyang Liu, Dr. Ashlee J. Howarth, Prof. Joseph T. Hupp and Prof. Omar K. Farha

Selective Photooxidation of a Mustard-Gas Simulant Catalyzed by a Porphyrinic Metal–Organic FrameworkLights, camera, oxidation! Inexpensive and commercially available LEDs are used to generate singlet oxygen with a MOF catalyst. The singlet oxygen is then used for the selective oxidation of a mustard-gas simulant, 2-chloroethyl ethyl sulfide, to give relatively nontoxic 2-chloroethyl ethyl sulfoxide; this safe, convenient, and effective process proceeds without formation of the toxic sulfone.

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Chemical Ligation and Isotope Labeling to Locate Dynamic Effects during Catalysis by Dihydrofolate Reductase

Dr. Louis Y. P. Luk, Dr. J. Javier Ruiz-Pernía, Aduragbemi S. Adesina, Dr. E. Joel Loveridge, Dr. Iñaki Tuñón, Prof. Dr. Vincent Moliner and Prof. Dr. Rudolf K. Allemann

Chemical Ligation and Isotope Labeling to Locate Dynamic Effects during Catalysis by Dihydrofolate ReductaseHeavy enzyme: Two dihydrofolate reductase (DHFR) hybrids were prepared; one hybrid contained heavy isotopes (2H, 13C, 15N) only in the mobile N-terminal segment, whereas in the other hybrid, only the C-terminal segment was isotopically labeled. Kinetic studies showed that isotopic substitution of the N-terminal segment affected only a physical step of catalysis, whereas the enzyme chemistry was affected by protein motions from the C-terminal segment.

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In Situ Modification of Metal–Organic Frameworks in Mixed-Matrix Membranes

Michael S. Denny Jr. and Prof. Dr. Seth M. Cohen

In Situ Modification of Metal–Organic Frameworks in Mixed-Matrix MembranesTriple M: Mixed-matrix membranes (MMMs) were obtained from a wide range of metal–organic frameworks. The membranes are flexible, easily handled, and contain highly crystalline MOFs, with large surface areas that remain amenable to chemical modification by postsynthetic methods.

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Access to Stable Metalloradical Cations with Unsupported and Isomeric Metal–Metal Hemi-Bonds

Xin Zheng, Dr. Xingyong Wang, Dr. Zaichao Zhang, Yunxia Sui, Prof. Xinping Wang and Prof. Philip P. Power

Access to Stable Metalloradical Cations with Unsupported and Isomeric Metal–Metal Hemi-BondsMetal–metal interactions: Three metalloradical cations are stabilized with weakly coordinating polyfluoroaluminate anions in the solid state, featuring supported, unsupported (see picture) and isomeric cobalt–cobalt hemi-bonds (bond order about 0.5). The first examples of isolable unsupported metal–metal hemi-bonds are reported, suggesting that other similar metalloradical species are accessible too.

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Strand-Biased Formation of G-Quadruplexes in DNA Duplexes Transcribed with T7 RNA Polymerase

Dr. Jia-quan Liu, Dr. Shan Xiao, Yu-hua Hao and Prof. Dr. Zheng Tan

Strand-Biased Formation of G-Quadruplexes in DNA Duplexes Transcribed with T7 RNA PolymeraseStrand discrimination: During transcription, the different interactions between a T7 RNA polymerase and the two strands of a DNA duplex result in G-quadruplex formation on the non-template strand, but not on the template strand. Structural analysis reveals that the polymerase induces distortion in the DNA duplex both inside and in front of the enzyme.

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Identification of tert-Butyl Cations in Zeolite H-ZSM-5: Evidence from NMR Spectroscopy and DFT Calculations

Dr. Weili Dai, Prof.Dr. Chuanming Wang, Dr. Xianfeng Yi, Prof. Dr. Anmin Zheng, Prof. Dr. Landong Li, Prof. Dr. Guangjun Wu, Prof. Dr. Naijia Guan, Prof. Dr. Zaiku Xie, Dipl.-Chem. Michael Dyballa and Prof. Dr. Michael Hunger

Identification of tert-Butyl Cations in Zeolite H-ZSM-5: Evidence from NMR Spectroscopy and DFT CalculationsCaptured and characterized: The intermediacy of tert-butyl cations in the acid-catalyzed conversion of isobutene on zeolite H-ZSM-5 was confirmed by their capture with ammonia. The resulting stable surface compounds were characterized by 1H/13C MAS NMR spectroscopy and analyzed by density functional theory (DFT) calculations.

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Precise Molecular Fission and Fusion: Quantitative Self-Assembly and Chemistry of a Metallo-Cuboctahedron

Dr. Ting-Zheng Xie, Dr. Kai Guo, Zaihong Guo, Wen-Yang Gao, Dr. Lukasz Wojtas, Dr. Guo-Hong Ning, Mingjun Huang, Dr. Xiaocun Lu, Jing-Yi Li, Dr. Sheng-Yun Liao, Dr. Yu-Sheng Chen, Dr. Charles N. Moorefield, Dr. Mary Jane Saunders, Prof. Stephen Z. D. Cheng, Prof. Chrys Wesdemiotis and Prof. George R. Newkome

Precise Molecular Fission and Fusion: Quantitative Self-Assembly and Chemistry of a Metallo-CuboctahedronBigger and bigger: A giant, 6 nm, shape-persistent, Archimedean-inspired cuboctahedron was quantitatively assembled and characterized by synchrotron X-ray analysis. The structure consists of one type of X-shaped, terpyridine-based ligand and 24 metal ions (Zn2+ or Cd2+). A fusion–fission switching process between a cuboctahedron and an octahedron could be induced by changing the concentration or the counterions.

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Oxidative Decarboxylation of Short-Chain Fatty Acids to 1-Alkenes

Dr. Alexander Dennig, Miriam Kuhn, Sebastian Tassoti, Anja Thiessenhusen, Dr. Stefan Gilch, Dr. Thomas Bülter, Dr. Thomas Haas, Dr. Mélanie Hall and Prof. Dr. Kurt Faber

Oxidative Decarboxylation of Short-Chain Fatty Acids to 1-AlkenesBiocatalysis: The oxidative decarboxylation of fatty acids using the P450 monooxygenase OleT in combination with the CamAB electron-transfer system and NAD(P)H recycling gave terminal alkenes (e.g., propene, 1-butene) with excellent conversion. The reaction may become applicable to the transformation of biomass into chemical compounds for organic synthesis.

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A Photoresponsive Smart Covalent Organic Framework

Ning Huang, Dr. Xuesong Ding, Dr. Jangbae Kim, Prof. Dr. Hyotcherl Ihee and Prof. Dr. Donglin Jiang

A Photoresponsive Smart Covalent Organic FrameworkSmart sheets: A “smart” covalent organic framework that is responsive to external stimuli is described. The anthracene-based framework is reversibly switchable between two-dimension sheets and concavo-convex skeletons upon irradiation and thermal stimuli. The structural transformation is accompanied by profound changes in porosity and π-electronic functions, demonstrating the usefulness of organic frameworks in exploring smart materials.

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Recruitment and Immobilization of a Fluorinated Biomarker Across an Interfacial Phospholipid Film using a Fluorocarbon Gas

Guang Yang, Miriam O'Duill, Prof. Véronique Gouverneur and Dr. Marie Pierre Krafft

Recruitment and Immobilization of a Fluorinated Biomarker Across an Interfacial Phospholipid Film using a Fluorocarbon GasAttractive interactions can arise between a fluorocarbon gas and a C2F5-labeled compound (red triangle with green tail) across a phospholipid monolayer, allowing recruitment and immobilization of the fluorinated compound in the phospholipid layer. This new phenomenon allowed preparation of microbubbles loaded with a C2F5-labeled hypoxia biomarker.

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Stereoselective Synthesis of Highly Substituted Tetrahydrofurans through Diverted Carbene O[BOND]H Insertion Reaction

Simon M. Nicolle, Dr. William Lewis, Prof. Dr. Christopher J. Hayes and Prof. Dr. Christopher J. Moody

Stereoselective Synthesis of Highly Substituted Tetrahydrofurans through Diverted Carbene O<img src="http://onlinelibrarystatic.wiley.com/undisplayable_characters/00f8ff.gif" alt="[BOND]" />H Insertion ReactionGone astray: Copper- or rhodium-catalyzed reactions of diazocarbonyl compounds with β-hydroxyketones give highly substituted tetrahydrofurans with excellent diastereoselectivity. The single-step reaction proceeds under mild conditions, starting as a carbene O[BOND]H insertion reaction, but then diverting to an intramolecular aldol reaction.

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Dynamic Release of Bending Stress in Short dsDNA by Formation of a Kink and Forks

Cheolhee Kim, O-chul Lee, Dr. Jae-Yeol Kim, Prof. Wokyung Sung and Prof. Nam Ki Lee

Dynamic Release of Bending Stress in Short dsDNA by Formation of a Kink and ForksGetting the bends: Strong bending induces two types of short dsDNA deformations, namely a kink in the middle and forks at the ends, as a mechanism of releasing the energy cost of bending (see figure). The two types of deformed dsDNA structures dynamically interconvert on a millisecond timescale. The transition from a fork to a kink is dominated by entropic contributions.

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Fluorine Rich Fluorides: New Insights into the Chemistry of Polyfluoride Anions

M. Sc. Thomas Vent-Schmidt, Dipl.-Chem. Felix Brosi, B. Sc. Jens Metzger, Dr. Tobias Schlöder, Prof. Xuefeng Wang, Prof. Lester Andrews, Dr. Carsten Müller, Dr. Helmut Beckers and Prof. Sebastian Riedel

Fluorine Rich Fluorides: New Insights into the Chemistry of Polyfluoride AnionsGive me F,F,F,F,F, five: The polyfluoride anions [F5] and Cs+[F3] have been identified by matrix-isolation spectroscopy and quantum-chemical methods. The V shaped [F5] ion gives rise to a band found in many IR laser ablation experiments that, up to now, could not be assigned.

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Highly Efficient Glutathione Peroxidase and Peroxiredoxin Mimetics Protect Mammalian Cells against Oxidative Damage

Dr. Debasish Bhowmick, Shubhi Srivastava, Prof. Dr. Patrick D'Silva and Prof. Dr. Govindasamy Mugesh

Highly Efficient Glutathione Peroxidase and Peroxiredoxin Mimetics Protect Mammalian Cells against Oxidative DamageIsoselenazoles display high glutathione peroxidase (GPx) and peroxiredoxin (Prx) activities and provide remarkable cytoprotection to human cells, mainly by catalyzing the reduction of H2O2 in the presence of cellular thiols. These compounds thus have the potential to be used as therapeutic agents for disorders mediated by reactive oxygen species (ROS; UT=untreated).

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Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of α-Oxo Acids

Dr. Lingling Chu, Jeffrey M. Lipshultz and Prof. Dr. David W. C. MacMillan

Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of α-Oxo AcidsThe direct decarboxylative arylation of α-oxo acids has been achieved by synergistic visible-light-mediated photoredox and nickel catalysis. This method offers rapid entry to aryl and alkyl ketone architectures from simple α-oxo acid precursors via an acyl radical intermediate. Significant substrate scope is observed with respect to both the oxo acid and arene coupling partners.

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