Understanding organofluorine chemistry. An introduction to the C–F bond

Abstract

Fluorine is the most electronegative element in the periodic table. When bound to carbon it forms the strongest bonds in organic chemistry and this makes fluorine substitution attractive for the development of pharmaceuticals and a wide range of speciality materials. Although highly polarised, the C-F bond gains stability from the resultant electrostatic attraction between the polarised C delta+ and F delta- atoms. This polarity suppresses lone pair donation from fluorine and in general fluorine is a weak coordinator. However, the C-F bond has interesting properties which can be understood either in terms of electrostatic/dipole interactions or by considering stereoelectronic interactions with neighbouring bonds or lone pairs. In this tutorial review these fundamental aspects of the C-F bond are explored to rationalise the geometry, conformation and reactivity of individual organofluorine compounds.

Two‐Dimensional Fluorinated Graphene: Synthesis, Structures, Properties and Applications

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A cell-based, high-throughput homogeneous time-resolved fluorescence assay for the screening of potential κ-opioid receptor agonists

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“…These palladium complexes incorporate nitrogenous, bidentate ligands which resist oxidation by electrophilic fluorination reagents, can support high-valence aryl palladium fluorides for subsequent carbon-fluorine reductive elimination and do not induce competing nitrogen-fluorine reductive elimination. Complex 10, which was prepared from 2-benzofuranylboronic acid (8), was successfully fluorinated on treatment with Selectfluor ® to furnish 7, albeit in a modest overall yield of 8% (Scheme 4).…”

“…properties [8], and can alter binding affinities with enzymes and receptors [9], rate of metabolism [10], clearance, absorption and transport [11].…”