Introduction
<P>Selectfluor
[
1]
is one of the most reactive electrophilic fluorinating reagents. It is a white, free-flowing,
virtually non-hygroscopic, high-melting solid (mp 170 °C)
[
2]
and is soluble in few polar solvents, e.g. MeCN, DMF, H
2O, MeNO
2, ionic liquids. It is a safe, stable, non-toxic, easy-to-handle reagent that is amenable
to industrial production. It provides an alternative to molecular fluorine which is
a hazardous, highly toxic, strong oxidant, with little or no specificity.
[
1]
Selectfluor helps in the fluorination of steroidal enol acetates,
[
3]
monofluoro ketomethylene dipeptide isosterase,
[
4]
carbanions, and Grignard reagents, and in the α-fluorination of sulfides,
[
2]
aldehydes and ketones.
[
5]
Besides these properties (in two-electron processes), it also shows oxidative characteristics,
and forms potent indium sources with molecular iodine, although it decomposes in
the presence of iodide ion. It is also useful in the conversion of common anions into
electrophiles.
[
6]
</P>
Preparation
<P>Selectfluor is commercially available. It can be prepared by the alkylation of
DABCO (TEDA) with dichloromethane. After counter-anion exchange with NaBF
4 and precipitation of NaCl from MeCN solution, fluorination with F
2 provides F-TEDA-BF
4.
[
1]
</P>
