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Articles from Wiley

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Visible-Light-Mediated Regioselective Allylation, Benzylation, and Silylation of Methylene-Malononitriles via Photoredox-Induced Radical Cation Fragmentation

12 agosto, 2019 - 00:00

Visible-light-mediated regioselevtive allylation, benzylation, and silylation of methylene-malononitriles with silanes have been realized. The reactions proceed via a photoredox-catalyzed σ-C-Si+· or σ-Si-Si+· type radical cation fragmentation.

[Communications]
Rongfang Liu, Shane Pui Mun Chia, Yi Yiing Goh, Han Wen Cheo, Binbin Fan, Ruifeng Li, Rong Zhou, Jie Wu
doi.org/10.1002/ejoc.201900902

Employing α-Diazocarbonyl Compound Chemistry in the Assembly of Medicinally Important Aryl(alkyl)thiolactam Scaffold

12 agosto, 2019 - 00:00

The RhII-catalyzed S-H insertion reaction of α-diazo-γ-butyrolactams provides a straightforward access to α-aryl(alkyl)thiolactams. The same diazo lactams can be easily converted to β-aryl(alkyl)thiolactams through AgI-catalyzed β-hydride shift followed by a sulfa-Michael addition. These two reactions of α-diazo-γ-butyrolactams pave the way toward two medicinally important scaffolds.

[Communications]
Darina Barkhatova, Daniil Zhukovsky, Dmitry Dar'in, Mikhail Krasavin
doi.org/10.1002/ejoc.201900944

Metal-Free Aerobic Oxidative C-O Coupling of C(<i>sp</i><sup>3</sup>)-H with Carboxylic Acids Catalyzed by DDQ and <i>tert</i>-Butyl Nitrite

12 agosto, 2019 - 00:00

A metal-free aerobic oxidative cross-coupling reaction between a benzylic C(sp3)-H bond and a carboxylic acid catalyzed by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and tert-butyl nitrite has been developed. This protocol provides a mild and efficient route to obtain diarylmethanol esters and phthalides. It can be regarded as a typical example of green chemistry in oxidative C-O coupling.

[Full Papers]
Decheng Pan, Zilong Pan, Zhiming Hu, Meichao Li, Xinquan Hu, Liqun Jin, Nan Sun, Baoxiang Hu, Zhenlu Shen
doi.org/10.1002/ejoc.201900773

An efficient Benzannulation protocol for the synthesis of 9,9-Diphenyl-9<i>H</i>-fluorenols using Intramolecular Allene Friedel-Crafts Annulation

12 agosto, 2019 - 00:00

A one-pot synthesis of 9,9-diphenyl-9H-fluorenols was developed starting from tert-propargyl alcohols and substituted acetylacetones using calcium triflate in good to excellent yields. This benzannulation reaction involves the formation of an allenyl ketone and a subsequent allene Friedel-Crafts annulation.

[Full Papers]
Srinivasarao Yaragorla, P. Rajesh
doi.org/10.1002/ejoc.201900895

A Fusion Method to Develop an Expanded Artificial Genomic RNA Replicable by Qβ Replicase

5 agosto, 2019 - 00:00

Length and functionality: A replication system for RNA-based genetic information consists of artificial genomic RNA (Beta-RNA) that encodes a part of RNA replicase. In this study, expanded long genomic RNAs which are also replicable, are obtained by fusing two replicable RNAs.

[Communications]
Kensuke Ueda, Ryo Mizuuchi, Fumio Matsuda, Dr. Norikazu Ichihashi
doi.org/10.1002/cbic.201900120

Synthesis of β-Chiral Amines by Dynamic Kinetic Resolution of α-Branched Aldehydes Applying Imine Reductases

5 agosto, 2019 - 00:00

From aldehydes to amines: Here, the proof of concept for enzymatic β-chiral secondary amine synthesis via dynamic kinetic resolution (DKR) employing imine reductases is demonstrated.

[Communications]
Philipp Matzel, Sebastian Wenske, Dr. Simon Merdivan, Prof. Dr. Sebastian Günther, Dr. Matthias Höhne
doi.org/10.1002/cctc.201900806

Toolbox of Post-synthetic Mordenite Modification Strategies: Impact on Textural, Acidic and Catalytic Properties

5 agosto, 2019 - 00:00

Which is best? Mordenite is one of the big five zeolites and finds extensive industrial application particularly in petrochemistry. Mordenite features a fascinating structure and its structural and chemical modification allow to impact catalytic outputs. But which post-synthetic modification strategy is the best suited for the generation of particular textural or chemical features in mordenite for a desired catalytic application?

[Full Papers]
Dr. Hussein Issa, Dr. Nourrddine Chaouati, Prof. Joumana Toufaily, Prof. Tayssir Hamieh, Dr. Alexander Sachse, Dr. Ludovic Pinard
doi.org/10.1002/cctc.201900927

Base-Assisted Electrografting of Aromatic Amines

5 agosto, 2019 - 00:00

Basicity is a strength: The role of organic bases in surface modification through the oxidation of aromatic amines is clarified and a grafting efficiency index is proposed to help choose the most suitable base. With strong bases, the covalent attachment of aromatic amines can occur at almost the open-circuit potential.

[Communications]
Corentin Anex, Dr. Ewen Touzé, Léonard Curet, Dr. Frédéric Gohier, Dr. Charles Cougnon
doi.org/10.1002/celc.201900979

Ratiometric DNA Walking Machine for Accurate and Amplified Bioassay

5 agosto, 2019 - 00:00

Don′t run before you can walk! A ratiometric DNA walking machine was developed based on the elemental isotope ratio measurement. The target DNA-triggered walking machine converted and amplified biological signals into mass spectrometric signal ratios (197Au/115In) by a burnt-bridge mechanism (see scheme).

[Communications]
Chaoqun Wang, Prof. Rui Liu, Jianyu Hu, Prof. Yi Lv
doi.org/10.1002/chem.201903034

Chirality-Controlled Self-Assembly of Amphiphilic Dibenzo[6]helicenes into Langmuir-Blodgett Thin Films

5 agosto, 2019 - 00:00

“…we have observed an interesting behaviour of bare amphiphilic helicenes in Langmuir layers and Langmuir-Blodgett films that is controlled by molecular chirality and the nature of the polar group.” Read more about the story behind the cover in the Cover Profile and about the research itself on page ▪▪ ff. (DOI: 10.1002/chem.201901695).

[Cover Profile]
Jan Holec, Dr. Jiří Rybáček, Dr. Jaroslav Vacek, Dr. Manfred Karras, Dr. Lucie Bednárová, Dr. Miloš Buděšínský, Michaela Slušná, Dr. Petr Holý, Prof. Bernd Schmidt, Dr. Irena G. Stará, Dr. Ivo Starý
doi.org/10.1002/chem.201903286

Photoinitiated Charge Transfer in a Triangular Silver(I) Hydride Complex and Its Oxophilicity

5 agosto, 2019 - 00:00

Inspired by previous studies on multinuclear silver hydrides and our work on bimetallic phosphine-stabilized compounds, we extended the nuclearity by designing a trimetallic system that allows for direct optical excitation of a metal-centered chromophore.” Read more about the story behind the cover in the Cover Profile and about the research itself on page ▪▪ ff. (DOI: 10.1002/chem.201901981).

[Cover Profile]
Sebastian V. Kruppa, Cedric Groß, Xin Gui, Florian Bäppler, Björn Kwasigroch, Dr. Yu Sun, Prof. Dr. Rolf Diller, Prof. Dr. Wim Klopper, Prof. Dr. Gereon Niedner-Schatteburg, Dr. Christoph Riehn, Prof. Dr. Werner R. Thiel
doi.org/10.1002/chem.201903111

The Distinct Conformational Landscapes of 4<i>S</i>-Substituted Prolines That Promote an <i>endo</i> Ring Pucker

5 agosto, 2019 - 00:00

Conformational control: 4S-Substituted prolines with electron-withdrawing 4-substitutents strongly promote the endo ring pucker and the δ conformation central to β-turns (ϕ, ψ=−80°, 0°), as determined by X-ray crystallography and calculations. This work suggests their broader application in protein design, medicinal chemistry, and catalysis.

[Full Papers]
Nicholas V. Costantini, Dr. Himal K. Ganguly, Maxwell I. Martin, Nicole A. Wenzell, Prof. Dr. Glenn P. A. Yap, Prof. Dr. Neal J. Zondlo
doi.org/10.1002/chem.201902382

Isolation and Crystallographic Characterization of Two, Nonisolated Pentagon Endohedral Fullerenes: Ho<sub>3</sub>N@<i>C</i><sub>2</sub>(22010)-C<sub>78</sub> and Tb<sub>3</sub>N@<i>C</i><sub>2</sub>(22010)-C<sub>78</sub>

5 agosto, 2019 - 00:00

Purified samples of Ho3N@C2(22010)-C78 and Tb3N@C2(22010)-C78 have been isolated from fullerenes and endohedral fullerenes present in carbon soot from graphite rods doped with Ho2O3 or Tb4O7. Crystallographic analysis of the endohedral fullerenes as cocrystals with Ni(OEP) shows that both molecules contain the chiral C2(22010)-C78 cage, which does not obey the isolated pentagon rule but has two sites where two pentagons share a common C−C bond (see figure).

[Full Papers]
Prof. Dr. Steven Stevenson, Amanda J. Rothgeb, Katelyn R. Tepper, Prof. Dr. James Duchamp, Prof. Dr. Harry C. Dorn, Xian B. Powers, Mrittika Roy, Prof. Dr. Marilyn M. Olmstead, Prof. Dr. Alan L. Balch
doi.org/10.1002/chem.201902559

Lithium-Bromide Exchange versus Nucleophilic Addition of Schiff's base: Unprecedented Tandem Cyclisation Pathways

5 agosto, 2019 - 00:00

Book-breaking boundaries: Standard textbook methodology of rapid, selective lithium-bromide exchange has been challenged in the case of bromo-substituted imines. Employing tert-butyllithium (tBuLi), five products are identified, revealing an unprecedented competitive nucleophilic addition pathway, along with tandem inter/intra-molecular cyclisations.

[Full Papers]
Dr. Samantha A. Orr, Dr. Emily C. Border, Prof. Philip C. Andrews, Dr. Victoria L. Blair
doi.org/10.1002/chem.201902140

Preparation of (Pentafluorosulfanyl)benzenes by Direct Fluorination of Diaryldisulfides: Synthetic Approach and Mechanistic Aspects

5 agosto, 2019 - 00:00

Taking the direct route: Direct fluorination of substituted aromatic disulfides or thiols provided arylsulfur pentafluorides (see scheme). The scope and limitation of the direct fluorination for the synthesis of new SF5-containing building blocks is described. The mechanism of the second step was investigated computationally.

[Full Papers]
Javier Ajenjo, Dr. Blanka Klepetářová, Dr. Martin Greenhall, Dr. Daniel Bím, Dr. Martin Culka, Dr. Lubomír Rulíšek, Dr. Petr Beier
doi.org/10.1002/chem.201902651

Bis(merocyanine) Hetero-Folda-Dimers: Evaluation of Exciton Coupling between Different Types of π-Stacked Chromphores

5 agosto, 2019 - 00:00

Exciting coupling: Three well-defined hetero-dye stacks comprising two chromophores are obtained upon folding of bis(merocyanine) dyes in nonpolar solvents. Theoretical investigations reveal a strong coupling between the dyes’ transition dipole moments within the dye stacks leading to significant changes of the absorption properties upon aggregation, which can be rationalized by molecular exciton theory.

[Full Papers]
Dr. Eva Kirchner, Dr. David Bialas, Prof. Frank Würthner
doi.org/10.1002/chem.201901757

Bis(merocyanine) Homo-Folda-Dimers: Evaluation of Electronic and Spectral Changes in Well-Defined Dye Aggregate Geometries

5 agosto, 2019 - 00:00

Facing stacks: Folding of three bis(merocyanine) dyes comprising chromophores of different conjugation lengths leads to cofacial π-stacks of two chromophores. Hence, detailed studies on the electronic and spectral changes of the chromophores upon aggregation are enabled.

[Full Papers]
Dr. Eva Kirchner, Dr. David Bialas, Marius Wehner, Dr. David Schmidt, Prof. Frank Würthner
doi.org/10.1002/chem.201901754

σ-Silane Platinum(II) Complexes as Intermediates in C−Si Bond-Coupling Processes

5 agosto, 2019 - 00:00

Intermediacy of σ-SiH PtII complexes: Primary silanes are shown to form σ-SiH complexes with cationic electron-deficient PtII complexes, [Pt(NHC′)(NHC)]+ (see graphic). These compounds evolve at room temperature through a double Si−H bond activation process that involves the formation of C−Si and Si−Pt bonds with concomitant extrusion of H2. Localized orbital analysis has revealed enhanced silylium character of the silicon atom when the silyl fragment is located at the apical position, which presumably favors the C−Si coupling event.

[Full Papers]
Pablo Ríos, Hugo Fouilloux, Dr. Josefina Díez, Dr. Pietro Vidossich, Prof. Dr. Agustí Lledós, Dr. Salvador Conejero
doi.org/10.1002/chem.201902226

Aminomethyl Transfer (Mannich) Reactions Between an O-Triethylsilylated Hemiaminal and Anilines, R<sub><i>n</i></sub>C<sub>6</sub>H<sub>5−<i>n</i></sub>NH<sub>2</sub> Leading to New Diamines, Triamines, Imines, or 1,3,5-Triazines Dependent upon Substituen

5 agosto, 2019 - 00:00

The reactions of the Mannich reagent Et3SiOCH2NMe2 with a variety of anilines (mono-substituted RC6H4NH2, R=H, 4-CN, 4-NO2, 4-Ph, 4-Me, 4-MeO, 4-Me2N; R2C6H3NH2; di-substituted R2=3,5-(CH3)2, 3,5-(CF3)2; R3C6H2NH2; tri-substituted R3=3,5-Me2-4-Br; and a “super bulky” aniline (Ar*NH2) [Ar*=2,6-bis(diphenylmethyl)-4-tert-butylphenyl]) have been investigated. These led to the formation of di- and triamines, as well as 1,3,5-triazines, or imines, depending on the substituent.

[Full Papers]
Anwar Jacintomoreno, Dr. Hemant K. Sharma, Dr. Alejandro Metta-Magaña, Prof. Dr. Keith H. Pannell
doi.org/10.1002/chem.201901877

Direct Synthesis of N-Heterocyclic Carbene-Stabilized Copper Nanoparticles from an N-Heterocyclic Carbene-Borane

5 agosto, 2019 - 00:00

Carbene-stabilized NPs: N-Heterocyclic carbene (NHC)-stabilized copper nanoparticles (NPs, see figure) were synthesized in toluene from mesitylcopper and an NHC-borane reagent, which plays a dual role of contributing to the reduction of [CuMes]2 to release Cu0 species and providing NHC ligands to stabilize the Cu NPs. The one-step reaction is quantitative with respect to the copper precursor.

[Full Papers]
Dr. Xavier Frogneux, Dr. Laura Hippolyte, Dr. Dimitri Mercier, Dr. David Portehault, Prof. Corinne Chanéac, Prof. Clément Sanchez, Prof. Philippe Marcus, Dr. François Ribot, Prof. Louis Fensterbank, Dr. Sophie Carenco
doi.org/10.1002/chem.201901534

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