!!10.1002/cssc.201900546!!!!10.1002/cmdc.201900176!!!!10.1002/chem.201902119!!!!10.1002/chem.201900852!!!!10.1002/cctc.201900597!!!!10.1002/chem.201901248!!!!10.1002/chem.201900950!!!!10.1002/cmdc.201900097!!!!10.1002/chem.201901321!!!!10.1002/cctc.201900462!!!!10.1002/chem.201900645!!!!10.1002/open.201900119!!!!10.1002/cphc.201900128!!!!10.1002/ejoc.201900683!!!!10.1002/chem.201901079!!!!10.1002/chem.201900275!!!!10.1002/cbic.201800770!!!!10.1002/cphc.201900193!!!!10.1002/chem.201900584!!!!10.1002/chem.201901770!!!!10.1002/chem.201805361!!!!10.1002/chem.201901769!!!!10.1002/cmdc.201900193!!!!10.1002/ejoc.201900247!!!!10.1002/chem.201900441!!!!10.1002/cssc.201900369!!!!10.1002/cssc.201900316!!!!10.1002/cssc.201803043!!!!10.1002/ejoc.201900061!!!!10.1002/ejoc.201801864!!!!10.1002/slct.201802918!!!!10.1002/slct.201803007!!!!10.1002/slct.201802745!!

Tackling Capacity Fading in Vanadium Redox Flow Batteries with Amphoteric Polybenzimidazole/Nafion Bilayer Membranes

Minimized battery capacity fading: Amphoteric polybenzimidazole/Nafion bilayer membranes are proposed to minimize capacity fading in the vanadium flow battery. The bilayer membrane with varying thickness can be used to tune the net transport of vanadium from the negative to the positive electrolyte across the ion-exchange membrane during charge-discharge cycling.

[Full Papers]

Fabio J. Oldenburg, Elisabeth Nilsson, Prof. Dr. Thomas J. Schmidt, Dr. Lorenz Gubler

doi.org/10.1002/cssc.201900546

The Discovery of LML134, a Histamine H3 Receptor Inverse Agonist for the Clinical Treatment of Excessive Sleep Disorders

Wake up, enjoy the day and sleep again! The histamine H3 receptor inverse agonist LML134 (18 b) achieves rapid oral absorption and brain penetration, leading to strong wakefulness-enhancing effects in rats. It also rapidly disengages from the receptor, a desirable profile to limit the risk of insomnia during the night following treatment. Clinical trials are ongoing to confirm its clinical efficacy in humans.

[Full Papers]

Dr. Thomas Troxler, Dr. Dominik Feuerbach, Dr. Xuechun Zhang, Dr. Charles R. Yang, Dr. Bharat Lagu, Dr. Mark Perrone, Dr. Tie-Lin Wang, Dr. Karin Briner, Dr. Mark G. Bock, Dr. Yves P. Auberson

doi.org/10.1002/cmdc.201900176

Atomically Defined Monocarborane Copper(I) Acetylides with Structural and Luminescence Properties Tuned by Ligand Sterics

The monocarborane cluster is used as a building block for the preparation of luminescent copper(I) complexes. Treatment of the 12-alkynyl-substituted cage with CuI and ammonia affords an isolable polymeric intermediate. Addition of phosphine and pyridine ligands transforms this intermediate to products featuring two to ten Cu centers. In the solid state, the products exhibit phosphorescence across the visible spectrum in colors from blue to deep red. The picture shows how the starting materials are transformed into copper complexes stabilized by N and P ligands. More information can be found in the Full Paper by N. Finney, B. Spingler, S. Duttwyler et al. (DOI: 10.1002/chem.201900584).

[Cover Pictures]

Kang Zhang, Dr. Yunjun Shen, Xiaoli Yang, Jiyong Liu, Tao Jiang, Prof. Dr. Nathaniel Finney, Prof. Dr. Bernhard Spingler, Prof. Dr. Simon Duttwyler

doi.org/10.1002/chem.201902119

The Quest for Molecular Grippers: Photo-Electric Control of Molecular Gripping Machinery

Molecular gripping: The emergence of nanoscale machines has inspired the quest for molecular grippers, and the effort has been expedited by the development of redox-active, quinone-based resorcin[4]arene cavitands. This Concept article describes the breakthroughs in the design and control of resorcin[4]arenes by electronic and electromagnetic stimuli using various electroanalytical, spectroscopic, and spectroelectrochemical methods. It outlines the current state and future perspectives of molecular grippers.

[Concepts]

Dr. Jovana V. Milić, Prof. Dr. François Diederich

doi.org/10.1002/chem.201900852

Data Mining the C−C Cross-Coupling Genome

Digging with precision: The tandem of dimensionality-reducing data-clustering maps, machine-learning, and molecular volcano plots permits a database of ∼25000 catalysts to be mined with precision in order to extract overarching chemical trends or to focus on the anticipated behavior of specific classes of catalysts.

[Full Papers]

Boodsarin Sawatlon, Dr. Matthew D. Wodrich, Dr. Benjamin Meyer, Alberto Fabrizio, Prof. Clémence Corminboeuf

doi.org/10.1002/cctc.201900597

Helicene Monomers and Dimers: Chiral Chromophores Featuring Strong Circularly Polarized Luminescence

Chiral emitters: Enantiomerically pure dimeric bis[6]helicenes with varying linker moieties and terminal groups were synthesized. They display intense UV/Vis absorptions and strong Cotton effects in the ECD spectra, with large gabs factors up to 0.047. High absolute fluorescence quantum yields (Φf) up to 0.35 were measured, and the circularly polarized luminescence (CPL) intensities (glum up to |0.025|), are among the strongest reported for pure organic molecules.

[Communications]

Cédric Schaack, Lorenzo Arrico, Eric Sidler, Marcin Górecki, Lorenzo Di Bari, Prof. Dr. François Diederich

doi.org/10.1002/chem.201901248

Ethynylbenziodazolones (EBZ) as Electrophilic Alkynylation Reagents for the Highly Enantioselective Copper-Catalyzed Oxyalkynylation of Diazo Compounds

Enantioselective reagents: Ethynylbenziodazolone (EBZ) cyclic hypervalent iodine reagents are synthesized for the first time, and display similar structure and reactivity to the established ethynylbenziodoxolone (EBX) reagents. They are used in the oxyalkynylation of diazo compounds to access imidate derivatives in high yield and enantioselectivity for a broad scope of diazo compounds and alkynes (see figure).

[Full Papers]

Dr. Durga Prasad Hari, Lionel Schouwey, Verity Barber, Dr. Rosario Scopelliti, Dr. Farzaneh Fadaei-Tirani, Prof. Dr. Jerome Waser

doi.org/10.1002/chem.201900950

Design of Natural-Product-Inspired Multitarget Ligands by Machine Learning

Natural products (NP) are precious sources of inspiration for medicinal chemists. We present a machine learning workflow for the identification of NP mimetics with desired polypharmacology. Starting from (−)-galantamine, a natural-product-based drug for the treatment of Alzheimer's disease, we identified eight synthetically accessible compounds with different multitarget profiles on disease-related targets. Two compounds constitute suitable starting points for hit-to-lead expansion.

[Communications]

Dr. Francesca Grisoni, Dr. Daniel Merk, Lukas Friedrich, Prof. Dr. Gisbert Schneider

doi.org/10.1002/cmdc.201900097

CS2 Reductive Coupling to Acetylenedithiolate by a Dinuclear Ytterbium(II) Complex

It takes two to couple: The unusual symmetric binding of CS2 by two YbII centers in a dinuclear complex supported by siloxide ligands led to the first example of reduction of CS2 to acetylenedithiolate (C2S22−) in a metal complex.

[Communications]

Davide Toniolo, Aurélien R. Willauer, Dr. Julie Andrez, Yan Yang, Dr. Rosario Scopelliti, Prof. Laurent Maron, Prof. Marinella Mazzanti

doi.org/10.1002/chem.201901321

Discovery of a Highly Active Catalyst for Hydrogenolysis of C−O Bonds via Systematic, Multi-metallic Catalyst Screening

Systematic screening: Application of a multi-metallic screening approach highlights the surprising activity of PdPt bimetallic nanoparticles in the hydrogenolysis of diphenyl ether.

[Full Papers]

Antoine P. van Muyden, Dr. Sviatlana Siankevich, Prof. Ning Yan, Prof. Paul J. Dyson

doi.org/10.1002/cctc.201900462

Bent Phosphaallenes With “Hidden” Lone Pairs as Ligands

Lone pair or no lone pair? The question whether bent phosphaallenes, R−P=C=L, show a “hidden” lone pair at the central carbon atom was investigated experimentally by exploring their ability to coordinate to CuI and AuI. An extensive EDA-NOCV bonding analysis shows the subtle differences between these heteroallenes in dependence of L in free and coordinated form (L = N-heterocyclic or alkyl(amino)carbene).

[Full Papers]

Dr. Xiaodan Chen, Dr. Zhongshu Li, Prof. Dr. Gernot Frenking, Prof. Dr. Israel Fernández, Prof. Lili Zhao, Prof. Dr. Hansjörg Grützmacher

doi.org/10.1002/chem.201900645

gem-Diethyl Pyrroline Nitroxide Spin Labels: Synthesis, EPR Characterization, Rotamer Libraries and Biocompatibility

Conserving the spin: The synthesis and characterization of iodoacetamide- and maleimide-functionalized spin labels based on the gem-diethyl pyrroline structure has been reported. The two nitroxide labels are compared to conventional gem-dimethyl analogs by site-directed spin labeling (SDSL) electron paramagnetic resonance (EPR) spectroscopy, using two water soluble proteins (see Figure: comparing the structures of three nitroxide labels attached to a cysteine residue)

[Full Papers]

Dr. Stephanie Bleicken, Tufa E. Assafa, Dr. Hui Zhang, Christina Elsner, Irina Ritsch, Dr. Maren Pink, Dr. Suchada Rajca, Prof. Dr. Gunnar Jeschke, Prof. Dr. Andrzej Rajca, Prof. Dr. Enrica Bordignon

doi.org/10.1002/open.201900119

An Additivity Scheme for Aromaticity: The Heteroatom Case

Heterocyclic building blocks: Using a newly expanded set of building blocks, the aromatic profiles of polycyclic (hetero)aromatic hydrocarbons are predicted with an additivity scheme based on nucleus-independent chemical shift (NICS)-XY-Scans. This approach enables simple and rapid access to the aromatic properties of complex systems and functional compounds.

[Articles]

Patrick Finkelstein, Dr. Renana Gershoni-Poranne

doi.org/10.1002/cphc.201900128

Front Cover: Beyond Simple Substitution Patterns - Symmetrically Tetrasubstituted [2.2]Paracyclophanes as 3D Functional Materials (Eur. J. Org. Chem. /2019)

The Front Cover shows the regioselective functionalization of already doubly substituted [2.2]paracyclophanes, resulting in symmetrical fourfold substituted three dimensional building blocks. The variety of synthetic accesses to these structures is summarized in the minireview entitled: “Beyond Simple Substitution Patterns - Symmetrically Tetrasubstituted [2.2]Paracyclophanes as 3D Functional Materials”. More information can be found in the Minireview by M. Mayor et al.

[Cover Picture]

Kevin J. Weiland, Almudena Gallego, Marcel Mayor

doi.org/10.1002/ejoc.201900683

Iron-Catalysed Remote C(sp3)−H Azidation of O-Acyl Oximes and N-Acyloxy Imidates Enabled by 1,5-Hydrogen Atom Transfer of Iminyl and Imidate Radicals: Synthesis of γ-Azido Ketones and β-Azido Alcohols

Dual roles for two reagents: In the presence of a catalytic amount of iron(III) acetylacetonate, the reaction of structurally diverse ketoxime esters with trimethylsilyl azide afforded γ-azido ketones in good to excellent yields. Fe acted as reductant and redox azido transfer reagent, while azide served not only as a nitrogen source to functionalise the unactivated C(sp3)−H bond, but also as a reductant to generate the catalytically active FeII species (see scheme).

[Full Papers]

Dr. Rubén O. Torres-Ochoa, Alexandre Leclair, Dr. Qian Wang, Dr. Jieping Zhu

doi.org/10.1002/chem.201901079

The Link between ZSM-5 Zeolite Crystallization and Mesopore Formation by Leaching

Crystal growth and crystal leaching: The crystal growth of ZSM-5 zeolites depend on the consumption of nanoparticles and oligomers. The variation in the consumption rates of each species leads to crystals with different properties, which can be reflected by crystal leaching. Hollow zeolites with microporous or mesoporous shells can be produced by optimizing the synthesis and post-synthetic conditions.

[Full Papers]

Teng Li, Dr. Johannes Ihli, Julian T. C. Wennmacher, Dr. Frank Krumeich, Prof. Jeroen A. van Bokhoven

doi.org/10.1002/chem.201900275

Novel Old Yellow Enzyme Subclasses

To expand the biocatalytic toolbox of available ene reductases, we screened selected bacterial strains for double bond reduction activity. The genomes of strains exhibiting activity were analysed bio-informatically, and 47 genes encoding putative ene reductases were identified. Interestingly, our combinatorial approach of phylogenetic and biochemical analysis allowed us to identify two novel Old Yellow Enzyme subclasses.

[Full Papers]

Dr. Christin Peters, David Frasson, Prof. Dr. Martin Sievers, Prof. Dr. Rebecca Buller

doi.org/10.1002/cbic.201800770

Examining the Structure Sensitivity of the Oxygen Evolution Reaction on Pt Single-Crystal Electrodes: A Combined Experimental and Theoretical Study

The structure sensitivity of the oxygen evolution reaction is studied by combining electrochemistry, in situ spectroscopy, and density functional theory calculations.

[Articles]

Francesco Bizzotto, Dr. Hassan Ouhbi, Dr. Yongchun Fu, Dr. Gustav K. H. Wiberg, Prof. Dr. Ulrich Aschauer, Prof. Dr. Matthias Arenz

doi.org/10.1002/cphc.201900193

Atomically Defined Monocarborane Copper(I) Acetylides with Structural and Luminescence Properties Tuned by Ligand Sterics

The carborane cage [CB11H12] is used as a versatile building block for the preparation of luminescent copper(I) complexes. The compound {(CB11H11-12-C≡C)2Cu4(NH3)3}n is transformed to homometallic products 3-13 bearing simple phosphine or pyridine ligands, all of which have been characterized by X-ray crystallography. Complexes 3-13 exhibit room-temperature phosphorescence across the visible spectrum in colors from blue to deep red.

[Full Papers]

Kang Zhang, Dr. Yunjun Shen, Xiaoli Yang, Jiyong Liu, Tao Jiang, Prof. Dr. Nathaniel Finney, Prof. Dr. Bernhard Spingler, Prof. Dr. Simon Duttwyler

doi.org/10.1002/chem.201900584

Antibody-Prodrug Conjugates with KSP Inhibitors and Legumain-Mediated Metabolite Formation

The use of legumain-cleavable caps as demonstrated here for antibody-prodrug conjugates (APDCs) holds promise in applying it to different types of solid tumor indications to improve the therapeutic window.” Read more about the story behind the cover in the Cover Profile and about the research itself on page ▪▪ ff. (DOI: 10.1002/chem.201900441).

[Cover Profile]

Dr. Hans-Georg Lerchen, Dr. Beatrix Stelte-Ludwig, Dr. Sandra Berndt, Dr. Anette Sommer, Dr. Lisa Dietz, Dr. Anne-Sophie Rebstock, Dr. Sarah Johannes, Dr. Leo Marx, Dr. Hannah Jörißen, Dr. Christoph Mahlert, Simone Greven

doi.org/10.1002/chem.201901770

Design and Structural Evolution of Matrix Metalloproteinase Inhibitors

On-target expansion: This review highlights the structural evolution of matrix metalloproteinase inhibitors (see figure). The repertoire of modulators has been expanded from broad-spectrum to subtype-selective inhibitors by structure-based drug design and is currently experiencing a further boost due to new insights into the disease relevance of this target class.

[Reviews]

Thomas Fischer, Nicole Senn, Prof. Dr. Rainer Riedl

doi.org/10.1002/chem.201805361

Antibody-Prodrug Conjugates with KSP Inhibitors and Legumain-Mediated Metabolite Formation

In the lysosome, legumain (LGMN in the picture) is required to release the active KSPi-metabolite from antibody-prodrug conjugates, in addition to complete antibody degradation. High LGMN expression in solid tumors compared with healthy tissue may lead to drugs with further increased tumor selectivity and lower off-target toxicity. More information can be found in the Communication by H.-G. Lerchen et al. (DOI: 10.1002/chem.201900441). The authors thank the graphic designers at The New Atlantic (Cologne) and Jürgen Franz for designing the cover image.

[Cover Pictures]

Dr. Hans-Georg Lerchen, Dr. Beatrix Stelte-Ludwig, Dr. Sandra Berndt, Dr. Anette Sommer, Dr. Lisa Dietz, Dr. Anne-Sophie Rebstock, Dr. Sarah Johannes, Dr. Leo Marx, Dr. Hannah Jörißen, Dr. Christoph Mahlert, Simone Greven

doi.org/10.1002/chem.201901769

Chemical Validation of DegS As a Target for the Development of Antibiotics with a Novel Mode of Action

Synergism: The development of small-molecule DegS inhibitors enabled validation of the bacterial HtrA S1 serine protease DegS and the outer membrane stress-response pathway as targets for the development of antibiotics with a novel mechanism of action. Importantly, these DegS inhibitors were found to act synergistically with established membrane-perturbing antibiotics such as colistin.

[Communications]

Dr. Jens Bongard, Dr. Anna Laura Schmitz, Dr. Alex Wolf, Dr. Gunther Zischinsky, Dr. Michel Pieren, Birgit Schellhorn, Dr. Kenny Bravo-Rodriguez, Dr. Jasmin Schillinger, Dr. Uwe Koch, Dr. Peter Nussbaumer, Dr. Bert Klebl, Prof. Dr. Jörg Steinmann, Prof. Dr. Jan Buer, Prof. Elsa Sanchez-Garcia, Prof. Dr. Michael Ehrmann, Prof. Dr. Markus Kaiser

doi.org/10.1002/cmdc.201900193

Adsorption of a Chiral Amine on Alginate Gel Beads and Evaluation of its Efficiency as Heterogeneous Enantioselective Catalyst

An organic catalyst derived from quinine can be adsorbed on alginate gels by following a simple protocol. The resulting solvogel beads are competent and highly stereoselective catalysts for an asymmetric Michael reaction.

[Full Papers]

Daniel Antonio Aguilera, Lisa Spinozzi Di Sante, Asja Pettignano, Riccardo Riccioli, Joël Roeske, Luce Albergati, Vasco Corti, Mariafrancesca Fochi, Luca Bernardi, Françoise Quignard, Nathalie Tanchoux

doi.org/10.1002/ejoc.201900247

Antibody-Prodrug Conjugates with KSP Inhibitors and Legumain-Mediated Metabolite Formation

Preferential metabolism in tumor versus healthy tissues. To further increase tumor selectivity of payload delivery, a new class of antibody-prodrug conjugates (APDCs) has been developed. In addition to antibody degradation, the lysosomal cleavage of a short peptide (“the cap”) mediated by the tumor-associated protease legumain is a key step for release of the active metabolite.

[Communications]

Dr. Hans-Georg Lerchen, Dr. Beatrix Stelte-Ludwig, Dr. Sandra Berndt, Dr. Anette Sommer, Dr. Lisa Dietz, Dr. Anne-Sophie Rebstock, Dr. Sarah Johannes, Dr. Leo Marx, Dr. Hannah Jörißen, Dr. Christoph Mahlert, Simone Greven

doi.org/10.1002/chem.201900441

Coolade. A Low-Foaming Surfactant for Organic Synthesis in Water

Diet foam: Foaming is a serious issue for organic syntheses performed under aqueous micellar-catalysis conditions. In this regard, the new designer surfactant ‘Coolade’ offers low-foaming properties while still enabling several important types of reactions to be performed in water.

[Full Papers]

Nicholas R. Lee, Dr. Margery Cortes-Clerget, Alex B. Wood, Dr. Daniel J. Lippincott, Haobo Pang, Farbod A. Moghadam, Dr. Fabrice Gallou, Prof. Bruce H. Lipshutz

doi.org/10.1002/cssc.201900369

Shielding Effect of Micelle for Highly Effective and Selective Monofluorination of Indoles in Water

Micelles make the difference: Highly selective direct monofluorination of indoles and arenes is developed through an approach that allows site-specific solubility of substrate and fluorine source in the micelle. This approach is suitable for a broad range of substrates with excellent functional group tolerance. Differences in binding constant and solubility of indoles and arenes in the micelle allow the fine-tuning of selectivity.

[Communications]

Dr. Pranjal P. Bora, Dr. Manisha Bihani, Dr. Scott Plummer, Dr. Fabrice Gallou, Prof. Sachin Handa

doi.org/10.1002/cssc.201900316

Appraisement of Crystal Expansion in CH3NH3PbI3 on Doping: Improved Photovoltaic Properties

Bigger and better: Imidazolium iodide (ImI) has been used as additive organic cation inside the CH3NH3PbI3 matrix. ImI primarily acts as a reservoir to control the spontaneous loss of iodide, thereby improving the stability of perovskite solar cells. Furthermore, optimized incorporation of ImI positively impacts crystallization of perovskite, passivates the surface, and minimize recombination losses.

[Full Papers]

Dr. Manuel Salado, Dr. Samrana Kazim, Prof. Mohammad Khaja Nazeeruddin, Prof. Shahzada Ahmad

doi.org/10.1002/cssc.201803043

Beyond Simple Substitution Patterns - Symmetrically Tetrasubstituted [2.2]Paracyclophanes as 3D Functional Materials

Symmetrically tetrasubstituted [2.2]paracyclophanes (PCs) are highlighted. The synthetic strategies are dominated by transannular effects arising from the face-to-face orientation of the benzene rings. Prominent patterns together with astonishing physical properties arising from the spatial arrangements enforced by the PC subunits are discussed.

[Minireview]

Kevin J. Weiland, Almudena Gallego, Marcel Mayor

doi.org/10.1002/ejoc.201900061

Slow Formation of Pseudorotaxanes in Water

Kinetically inert and thermodynamically stable pseudorotaxanes with slow formation kinetics in water are developed. The substitution pattern of the hydrophilic end-group of rigid OPE axles controls the association kinetics with a Diederich-type cyclophane.

[Communications]

Yves Aeschi, Laurent Jucker, Daniel Häussinger, Marcel Mayor

doi.org/10.1002/ejoc.201801864

Copper Catalyzed Direct Synthesis of Nitriles from Acyl Azides

A novel and general protocol for the copper catalyzed reductive elimination of acyl azides to nitriles using triethoxysilane is reported. Various nitriles are obtained in moderate to excellent yields with good functional group tolerance and high chemoselectivity.

[Communications]

Prof. Yang Chen, Yu Liu, Xiao Zhang, Da Lu, Lixin Yang, Junfeng Deng, Prof. Shengqi Deng

doi.org/10.1002/slct.201802918

Aerobic Oxidation of Methyl-substituted β-Carbolines Catalyzed by N-Hydroxyphthalimide and Metal Catalyst

Carboxylic functionalized β-carbolines have been synthesized in good to excellent yields and high selectivity by oxygen in the presence of NHPI and transition metal salt under mild conditions

[Communications]

Hongda Qiu, Weida Liang, Dr. Gongjun Zhang, Miaoman Lin, Wanmin Liu, Prof. Zhanghua Gao, Dr. Wenting Wei, Dr. Chunlan Tang, Dr. Haixiao Jin, Prof. Hongze Liang, Prof. Xiaojun Yan

doi.org/10.1002/slct.201803007

Betti Bases from 4-(3-Pyridazo)-1-naphthol: Synthesis, Coordination Behaviour and Unusual Substitution Reactions

Synthesis, characterization and complexation ability study of a series of Betti bases from 4-(3-pyridyl)azo-1-naphthol dye, possessing flexible methylene or more constrained aryl-methyne spaced NH-containing side-chains, is presented. An unexpected result with side-chain pyridyl group replacement was obtained and the product was analysed by XRD. A possible pathway was suggested and synthetically confirmed.

[Full Papers]

Prof. Dr. Vanya B. Kurteva, Dr. Lubomir A. Lubenov, Prof. Dr. Boris L. Shivachev, Prof. Dr. Rositsa P. Nikolova, Prof. Dr. Katharina M. Fromm

doi.org/10.1002/slct.201802745