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Novel Process for Generating Useful Electrophiles from Common Anions Using Selectfluor® Fluorination Agent

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journal contribution
posted on 15.05.2002, 00:00 by Robert G. Syvret, Kathleen M. Butt, Tung P. Nguyen, Victoria L. Bulleck, Ryan D. Rieth
In the present work, the electrophile equivalents Cl+, Br+, SCN+, and NO2+ are generated from their respective sodium, potassium, and in some cases ammonium salts (M+X-) by reaction with Selectfluor electrophilic fluorination agent in acetonitrile solution at room temperature. These generated electrophilic species subsequently react in situ with a variety of aromatic substrates containing one or more substituent groups including H, F, Cl, CH3, COOH, C(O)CH3, NO2, and OR‘ and NR‘R‘ ‘ where R‘ and R‘ ‘ are H or CH3. The resulting substitution products are, in most cases, isolable as pure compounds in high yield. Variations in the process include the use of other anions, electrophilic fluorination agents, and solvents.