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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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Hexaphyrin as a Potential Theranostic Dye for Photothermal Therapy and 19F Magnetic Resonance Imaging

Hexaphyrin as a Potential Theranostic Dye for Photothermal Therapy and 19F Magnetic Resonance Imaging

meso-Aryl-substituted expanded porphyrins have two key features as potential theranostic agents: excellent NIR absorption and the possibility for the introduction of multiple fluorine atoms at the meso-aryl groups. Hexaphyrin exhibited an intense photothermal effect and potential for use in visualization by 19F MRI. These results shed light on the utility of expanded porphyrins as theranostic agents.

[Full Paper]
Tomohiro Higashino, Hirotaka Nakatsuji, Ryosuke Fukuda, Haruki Okamoto, Hirohiko Imai, Tetsuya Matsuda, Hidehito Tochio, Masahiro Shirakawa, Nikolai V. Tkachenko, Mitsuru Hashida, Tatsuya Murakami, Hiroshi Imahori
ChemBioChem, March 24, 2017, https://doi.org/10.1002/cbic.201700071 Read article

Erythrosine B Catalyzed Visible-Light Photoredox Arylation–Cyclization of N-Alkyl-N-aryl-2-(trifluoromethyl)acrylamides to 3-(Trifluoromethyl)indolin-2-one Derivatives

Erythrosine B Catalyzed Visible‐Light Photoredox Arylation–Cyclization of N‐Alkyl‐N‐aryl‐2‐(trifluoromethyl)acrylamides to 3‐(Trifluoromethyl)indolin‐2‐one Derivatives

Erythrosine B has been utilized as a novel photoredox sensitizer in the arylation-cyclization reaction of N-alkyl-N-aryl-2-(trifluoromethyl)acrylamides to indolin-2-ones. Arenediazonium tetrafluoroborates served as the source aryl radicals under the irradiation of blue LEDs at –50 °C. The scope and the limitations were investigated, and 27 examples (up to 83 % yield) are presented.

[Communication]
Zsombor Gonda, Ferenc Béke, Orsolya Tischler, Milán Petró, Zoltán Novák, Balázs L. Tóth
Eur. J. Org. Chem., February 10, 2017, https://doi.org/10.1002/ejoc.201601493 Read article

Photocatalytic Trifluoromethylthiolation of Aromatic Alkenes Associated with Hydroxylation and Alkoxylation

Photocatalytic Trifluoromethylthiolation of Aromatic Alkenes Associated with Hydroxylation and Alkoxylation

Activator-free: An additive-free photoredox-catalyzed trifluoromethylthiolation of aromatic alkenes has been developed. Trifluoromethanesulfenyl radical (.SCF3) is efficiently generated from a photocatalyst and an electrophilic triflouromethylthiolating reagent. This photoredox system induces a regioselective oxytrifluoromethylthiolation of carbon–carbon double bonds through catalytic processes without any activator.

[Communication]
Yanjie Li, Takashi Koike, Munetaka Akita
Asian J. Org. Chem., January 18, 2017, https://doi.org/10.1002/ajoc.201600562 Read article

Step Transfer-Addition and Radical-Termination (START) Polymerization of α,ω-Unconjugated Dienes under Irradiation of Blue LED Light

Step Transfer‐Addition and Radical‐Termination (START) Polymerization of α,ω‐Unconjugated Dienes under Irradiation of Blue LED Light

A novel polymerization method, step transfer-addition and radical-termination, suitable for α,ω-unconjugated dienes has been discovered through the construction of perfluorocarbon-containing alternating copolymers under irradiation of visible light at room temperature for the first time.

[Communication]
Tianchi Xu, Hongnan Yin, Xiaohong Li, Lifen Zhang, Zhenping Cheng, Xiulin Zhu
Macromol. Rapid Commun., November 11, 2016, https://doi.org/10.1002/marc.201600587 Read article

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