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Electrophilic fluorination is the combination of a carbon-centered nucleophile with an electrophilic source of fluorine to afford organofluorine compounds. Although elemental fluorine and reagents incorporating an oxygen-fluorine bond can be used for this purpose, they have largely been replaced by reagents containing a nitrogen-fluorine bond.
Electrophilic fluorinating reagents could in principle operate by electron transfer pathways or an S N 2 attack at fluorine. This distinction has not been decided. [2] By using a charge-spin separated probe, [3] it was possible to show that the electrophilic fluorination of stilbenes with Selectfluor proceeds through an SET/fluorine atom transfer mechanism.
Starting in the late 1940s, a series of electrophilic fluorinating methodologies were introduced, beginning with CoF 3. Electrochemical fluorination ("electrofluorination") was announced, which Joseph H. Simons had developed in the 1930s to generate highly stable perfluorinated materials compatible with uranium hexafluoride. [15]
In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. [1] Because electrophiles accept electrons, they are Lewis acids. [2] Most electrophiles are positively charged, have an atom that carries a partial positive charge, or have an atom that does not have an octet of electrons.
Electrochemical fluorination (ECF), or electrofluorination, is a foundational organofluorine chemistry method for the preparation of fluorocarbon-based organofluorine compounds. [1] The general approach represents an application of electrosynthesis .
More recently, trifluoromethylation of diazonium salts has been developed and is referred to as a 'Sandmeyer-type' reaction. Diazonium salts also react with boronates, iodide, thiols, water, hypophosphorous acid and others, [6] and fluorination can be carried out using tetrafluoroborate anions (Balz–Schiemann reaction). However, since these ...
Radical fluorination is a type of fluorination reaction, complementary to nucleophilic and electrophilic approaches. [1] It involves the reaction of an independently generated carbon-centered radical with an atomic fluorine source and yields an organofluorine compound .
As mentioned above, aryl and alkenyl nonaflates are useful as electrophiles in palladium catalyzed cross coupling reactions. Their reactivity generally mirrors that of the more commonly encountered triflate electrophiles, but nonaflates tend to be less prone to hydrolysis to ketones (in the case of alkenyl sulfonates) and phenols (in the case of aryl sulfonates).