• KF can also behave as a base in a wide variety of applications:
•
Reviews: Fluoride ion as a base in organic synthesis: Chem. Rev., 80, 429 (1980). Alkali metal fluorides in organic synthesis: Synthesis, 169 (1983). See also Cesium fluoride, 12885.•
In the Henry reaction of 1-nitropropane with an aldehyde: Org. Synth. Coll., 9, 242 (1998). For the methylenation of catechols with Dibromomethane, A10456, in DMF: Tetrahedron Lett., 3361 (1976). In an olefination reaction with 2,2,2-Trifluoroacetophenone, A11403: J. Org. Chem., 59, 2898 (1994). In combination with 18-crown-6 for selective removal of Fmoc protecting groups under mild conditions: Synth. Commun., 24, 187 (1994).• Widely used in "halex" fluorination reactions for the preparation of aryl fluorides from the corresponding chlorides by heating in a dipolar aprotic solvent, e.g. tetramethylene sulfone: J. Fluorine Chem., 46, 529 (1990). Other solvents including DMSO, DMA and NMP are also successfully employed. For a review of the preparation of aryl fluorides by halogen exchange, see: Chem. Ind. (London), 518 (1986). Aryl nitro groups can also be displaced in suitable molecules: J. Org. Chem., 56, 6406 (1991). Relative rates for aromatic fluorodenitration in different solvents were found to be: DMSO > tetramethylene sulfoxide > DMA > NMP > tetramethylene sulfone >> acetonitrile > DME: J. Fluorine Chem., 35, 591 (1987).
• An active form of KF has been prepared by recrystallization from methanol followed by drying at 100oC: Tetrahedron, 51, 6363 (1995).
•
For use in trifluoromethylation of aromatic, allylic and ɑ-carboxy halides, see Methyl chlorodifluoroacetate, A18623.•
Has been used in cleavage of silyl protecting groups under phase-transfer conditions (see tert-Butyldimethylchlorosilane, A13064): J. Am. Chem. Soc., 90, 4462, 4464 (1968); 96, 2250 (1974); J. Chem. Soc., Chem. Commun., 514 (1979).