First application of ionic liquids in electrophilic fluorination of arenes; Selectfluor™ (F-TEDA-BF4) for “green” fluorination

Regioselective iodination of arenes in ionic liquids mediated by SelectfluorTM reagent F-TEDA-BF4

“…One intriguing alternative to molecular solvents, that has recently received a good deal of attention, is represented by the use of ionic liquids. 13 These solvents, mainly owing to their high thermal stability and lack of measurable vapor pressure, appear to be ideal media for performing reactions under, "eco-friendly" conditions. Herein we report an efficient method for the iodination of representative aromatic rings using iodine and 1-(chloromethyl) The present study was therefore undertaken to determine the efficacy of this iodinating system in an ionic liquid and to obtain, from comparison with molecular solvents, further information about the properties of these new reaction media.…”

Selectfluor: Mechanistic Insight and Applications

“…Recently, the use of ionic liquids, such as triflate, tetrafluoroborate, and phosphorous hexafluoride salts of 1-ethyl-3-methylimidazolium or 1-butyl-3-ethylimidazolium, for reactions with 1 has received attention. [23,24] As reaction efficiencies are higher for many substrates in these reusable and environmentally friendly media, these studies have opened an interesting avenue for further investigation.…”

Ring-fluorinated naphthalene and indene synthesis via 6- and 5-endo-trig cyclizations of gem-difluoroalkenes by carbon nucleophiles

“…Such compounds are less accessible by conventional electrophilic methods. Electrophilic fluorination of naphthalenes affords 1-fluoronaphthalenes as major products and is severely deactivated by electron-withdrawing groups [3][4][5] (for the synthesis of fluoronaphthalenes, see [23,24]; for the synthesis of naphthalenes, see [25]). …”