Simple α-fluorobenzyl anions reacted with electrophiles such as non-activated alkyl halides and chlorotrimethylsilane. Upon treatment with LTMP as the base, fluoromethylbenzenes took part in the formation of α-monofluorobenzyl anions without stabilizing o-substituents. Furthermore, the resulting α-silyl fluoromethylbenzenes reacted with electrophiles such as acetophenone and benzaldehyde in the presence of cesium fluoride to form α-fluorobenzylated alcohols.