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elemental fluorine and reagents incorporating an oxygen-fluorine bond can be used for this purpose, they have largely been replaced by reagents containing a nitrogen-fluorine bond.[1]
Electrophilic fluorination offers an alternative to nucleophilic fluorination methods employing alkali or ammonium fluorides and methods employing sulfur fluorides for the preparation of organofluorine compounds. Development of electrophilic fluorination reagents has always focused on removing electron density from the atom attached to fluorine; however, compounds containing nitrogen-fluorine bonds have proven to be the most economical, stable, and safe electrophilic fluorinating agents. Electrophilic N-F reagents are either neutral or cationic and may possess either sp2- or sp3-hybridized nitrogen. Although the precise mechanism of electrophilic fluorination is currently unclear, highly efficient and stereoselective methods have been developed.
Some common fluorinating agents used for organic synthesis are N-fluoro-o-benzenedisulfonimide (NFOBS), N-fluorobenzenesulfonimide (NFSI), and Selectfluor.[1]
^ abBaudoux, Jérôme; Cahard, Dominique (2008). "Electrophilic Fluorination with <SCP>N</SCP> – <SCP>F</SCP> Reagents". Organic Reactions. pp. 1–326. doi:10.1002/0471264180.or069.02. ISBN 978-0-471-26418-7.
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reagents containing a nitrogen-fluorine bond. Electrophilicfluorination offers an alternative to nucleophilic fluorination methods employing alkali or ammonium...
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treatment with fluorine. A colourless salt that tolerates air, Selectfluor has been commercialized for use for electrophilicfluorination. As an unhindered...
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propellant NF 3–F 2 gas generators. They are also used as reagents for electrophilicfluorination of aromatic compounds in organic chemistry. As fluorinating agents...
Science at the University of Paris after doing research regarding electrophilicfluorination of uranium dioxide at the Zoé reactor in Fontenay-aux-Roses. He...
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understand this reactivity phenomenon. Each series varied by degree of fluorination. Bond lengths and charge densities are shown as functions of how many...
direct fluorination of chlorine with excess fluorine gas at 350 °C and 250 atm, and on a small scale by reacting metal chlorides with fluorine gas at...
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properties of pyridine, as it easily supports bond formation via an electrophilic attack. However, because of the separation of the lone pair from the...
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