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Fluorine Chemistry

Rapid improvements in the understanding of fluorine and organofluorine chemistry are allowing fluorinated compounds to be synthesised more easily and safely than ever before. By using innovative fluorination techniques, chemists can harness the unique properties of fluorine for novel applications in biological, pharmaceutical and materials science. Recently, there has been increased interest in research on the development of new radiolabelling reagents and methods for the late-stage introduction of 18F into biologically active molecules for applications in positron emission tomography.

The image is taken from the cover featuring a Microreview by T. Billard et al. on direct trifluoromethylthiolation reactions published in the European Journal of Organic Chemistry.

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Synthesis of N-Nitroso CHF2-Pyrazolines and Their Transformation into CHF2-Isoxazolines and -Pyrazoles

Synthesis of N‐Nitroso CHF2‐Pyrazolines and Their Transformation into CHF2‐Isoxazolines and ‐Pyrazoles

[Full Paper]
Pavlo S. Lebed, Johan Fenneteau, Yong Wu, Janine Cossy, Pavel K. Mykhailiuk
Eur. J. Org. Chem., August 15, 2017, https://doi.org/10.1002/ejoc.201700803 Read article

Monitoring Fluorinated Dendrimer-Based Self-Assembled Drug-Delivery Systems with 19F Magnetic Resonance

Monitoring Fluorinated Dendrimer‐Based Self‐Assembled Drug‐Delivery Systems with 19F Magnetic Resonance

Monitoring drug-delivery systems with an imaging modality is of great importance to achieve optimal therapeutic effects. Here, 19F magnetic resonance is used as a convenient and sensitive tool to monitor self-assembled drug-delivery systems because changes in the self-assembly profile sensitively induce corresponding 19F magnetic resonance responses.

[Full Paper]
Xin Liu, Yaping Yuan, Shaowei Bo, Yu Li, Zhigang Yang, Xin Zhou, Shizhen Chen, Zhong-Xing Jiang
Eur. J. Org. Chem., August 15, 2017, https://doi.org/10.1002/ejoc.201700566 Read article

Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling of Secondary α-(Trifluoromethyl)benzyl Tosylates

Palladium‐Catalyzed Suzuki–Miyaura Cross‐Coupling of Secondary α‐(Trifluoromethyl)benzyl Tosylates

Only with fluorine: A palladium-catalyzed cross-coupling of secondary α-(trifluoromethyl)benzyl tosylates with (hetero)aryl boronic acids enables the stereoselective synthesis of more than twenty 1,1-diaryl-2,2,2-trifluoroethanes. The cross-coupling was shown to occur with predominant inversion of configuration.

[Communication]
Marta Brambilla, Matthew Tredwell
Angew. Chem. Int. Ed., August 15, 2017, https://doi.org/10.1002/anie.201706631 Read article

Direct Monofluoromethylthiolation with S-(Fluoromethyl) Benzenesulfonothioate

Direct Monofluoromethylthiolation with S‐(Fluoromethyl) Benzenesulfonothioate

An electrophilic shelf-stable monofluoromethylthiolating reagent, S-(fluoromethyl) benzenesulfonothioate (1), was developed. Reagent 1 couples with a variety of aryl boronic acids or unactivated alkenes to give the corresponding monofluoromethylthiolated arenes and alkanes in high yields.

[Communication]
Qunchao Zhao, Long Lu, Qilong Shen
Angew. Chem. Int. Ed., August 11, 2017, https://doi.org/10.1002/anie.201705633 Read article

Fluoro-Carba-Sugars are Glycomimetic Activators of the glmS Ribozyme

Fluoro‐Carba‐Sugars are Glycomimetic Activators of the glmS Ribozyme

Fluorinated sugar mimics: Mono-fluorinated carba-sugar analogs of glucoseamine-6-phosphate and idosamine-6-phosphate were synthesized. Fluoro-carba-glucosamine-6-phosphate acts as an activator of the unique self-cleavage mechanism of the glmS ribozyme.

[Full Paper]
Daniel Matzner, Anna Schüller, Torben Seitz, Valentin Wittmann, Günter Mayer
Chem. Eur. J., August 10, 2017, https://doi.org/10.1002/chem.201702371 Read article

Aryne Insertion into σ Bonds

Aryne Insertion into σ Bonds

Double trouble: The application of Kobayashi′s aryne precursor for the simultaneous construction of two sigma bonds on an arene ring and its importance in organic chemistry are described. Examples include transformations that employ transition-metal catalysis and those that do not.

[Focus Review]
Manjoorahmed Asamdi, Kishor H. Chikhalia
Asian J. Org. Chem., August 10, 2017, https://doi.org/10.1002/ajoc.201700284 Read article

Fluorinated Boronic Acids: Acidity and Hydrolytic Stability of Fluorinated Phenylboronic Acids

Fluorinated Boronic Acids: Acidity and Hydrolytic Stability of Fluorinated Phenylboronic Acids

Introduction of fluorine into an aromatic ring of phenylboronic acid enhances its Lewis acidity, but makes it prone to the hydrodeboronation reaction. The pKa values obtained by potentiometric and spectrophotometric methods are in good agreement.

[Full Paper]
Dorota Zarzeczańska, Agnieszka Adamczyk-Woźniak, Amanda Kulpa, Tadeusz Ossowski, Andrzej Sporzyński
Eur. J. Inorg. Chem., August 07, 2017, https://doi.org/10.1002/ejic.201700546 Read article

Synthesis of Pinpoint-Fluorinated Polycyclic Aromatic Hydrocarbons: Benzene Ring Extension Cycle Involving Microwave-Assisted SNAr Reaction

Synthesis of Pinpoint‐Fluorinated Polycyclic Aromatic Hydrocarbons: Benzene Ring Extension Cycle Involving Microwave‐Assisted SNAr Reaction

Lords of the rings: Fluoroarenes bearing no electron-withdrawing groups (non-activated fluoroarenes) readily underwent nucleophilic aromatic substitution with α-cyanocarbanions under microwave irradiation. The sequence (i) formylalkylation involving cyanoalkylation of fluoroarenes, (ii) difluorovinylidenation, and (iii) Friedel–Crafts-type cyclization, afforded extended fluoroarenes by one benzene ring per cycle. Furthermore, the performance of multiple cycles successfully provided higher-order pinpoint-fluorinated polycyclic aromatic hydrocarbons (F-PAHs).

[Communication]
Kohei Fuchibe, Hisanori Imaoka, Junji Ichikawa
Chem. Asian J., August 02, 2017, https://doi.org/10.1002/asia.201700870 Read article

Effect of Fluoride-Modification on the Phillips Cr/SiO2 Catalyst for Ethylene Polymerization

Effect of Fluoride‐Modification on the Phillips Cr/SiO2 Catalyst for Ethylene Polymerization

The fluorine effect: Fluorinated Phillips catalysts (Cr/F-SiO2) exhibit an enhanced reactivity towards ethylene polymerization and copolymerization. DFT calculations show that the difference of the Gibbs free energy barriers between chain transfer and chain propagation increased after the introduction of the fluoride onto the silica surface, which is in accordance with the increased molecular weight of the polyethylene formed using the Cr/F-SiO2 catalyst.

[Full Paper]
Qiaoqiao Sun, Ruihua Cheng, Zhen Liu, Xuelian He, Ning Zhao, Boping Liu
ChemCatChem, July 27, 2017, https://doi.org/10.1002/cctc.201700375 Read article

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