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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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Formation of a Cubic Liquid Crystalline Nanostructure with π-Conjugated Fluorinated Rods on the Gyroid Minimal Surface

Formation of a Cubic Liquid Crystalline Nanostructure with π‐Conjugated Fluorinated Rods on the Gyroid Minimal Surface

The power of fluorination: Tailoring the fluorination pattern modifies the soft self-assembly of oligo(phenylene ethynylene)-based X-shaped polyphiles, leading to the first thermotropic liquid crystalline cubic phase with the π-conjugated rods forming the gyroid minimal surface. The organization of the rods perpendicular to the minimal surface and parallel to each other allows π-stacking interactions in all three dimensions of space (see figure).

[Communication]
Marco Poppe, Changlong Chen, Feng Liu, Silvio Poppe, Carsten Tschierske
Chem. Eur. J., April 27, 2017, https://doi.org/10.1002/chem.201700905 Read article

Tris(pentafluoroethyl)germane: Deprotonation and Hydrogermylation Reactions

Tris(pentafluoroethyl)germane: Deprotonation and Hydrogermylation Reactions

Generating germanium complexes: The chemistry around (C2F3)3GeH is explored. Treating the germane with different bases yields the germanate(II) ion [Ge(C2F5)3], serving as a germyl group transfer reagent. The reaction with different metal complexes opens access to a variety of different compounds. Hydrogermylation reactions of (C2F5)3GeH with alkynes afforded different stereoisomers, depending on the respective reaction conditions and substrates.

[Full Paper]
Stefanie Pelzer, Beate Neumann, Hans-Georg Stammler, Nikolai Ignat'ev, Berthold Hoge
Chem. Eur. J., April 27, 2017, https://doi.org/10.1002/chem.201700634 Read article

Suzuki–Miyaura Cross-Coupling Reactions of Highly Fluorinated Arylboronic Esters: Catalytic Studies and Stoichiometric Model Reactions on the Transmetallation Step

Suzuki–Miyaura Cross‐Coupling Reactions of Highly Fluorinated Arylboronic Esters: Catalytic Studies and Stoichiometric Model Reactions on the Transmetallation Step

Deserves a metal: The Suzuki–Miyaura cross-coupling reaction of highly fluorinated boronic esters, such as 2-Bpin-C5NF4, was investigated by using [Pd(Me)2(tmeda)] or trans-[PdBr{4-C6H4CH2CH{NHC(O)CH3}CO2Et}(PiPr3)2] as precatalysts. Stoichiometric studies on the transmetallation step revealed the high reactivity of a Pd fluorido derivative towards 2-BpinC5NF4, which leads to the formation of an ionic intermediate and finally yields the cross-coupling product.

[Full Paper]
Johannes Kohlmann, Thomas Braun, Reik Laubenstein, Roy Herrmann
Chem. Eur. J., April 26, 2017, https://doi.org/10.1002/chem.201700549 Read article

19F NMR Spectroscopic Analysis of the Binding Modes in Triple-Helical Peptide Nucleic Acid (PNA)/MicroRNA Complexes

19F NMR Spectroscopic Analysis of the Binding Modes in Triple‐Helical Peptide Nucleic Acid (PNA)/MicroRNA Complexes

Seeing into the complex: The stoichiometry of the binding, thermal denaturation of complexes, and transition between triple-helical peptide nucleic acid (PNA)/microRNA and (PNA)2/microRNA complexes were characterized by 19F NMR spectroscopy (see figure).

[Full Paper]
Ville Tähtinen, Lotta Granqvist, Merita Murtola, Roger Strömberg, Pasi Virta
Chem. Eur. J., April 25, 2017, https://doi.org/10.1002/chem.201700601 Read article

Selective Late-Stage Hydrodefluorination of Trifluoromethylarenes: A Facile Access to Difluoromethylarenes

Selective Late‐Stage Hydrodefluorination of Trifluoromethylarenes: A Facile Access to Difluoromethylarenes

[Communication]
Socrates B. Munoz, Chuanfa Ni, Zhe Zhang, Fang Wang, Nan Shao, Thomas Mathew, George A. Olah, G. K. Surya Prakash
Eur. J. Org. Chem., April 20, 2017, https://doi.org/10.1002/ejoc.201700396 Read article

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

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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