ELECTROPHILIC RADIOFLUORATION OF ARYLTRIMETHYLSILANES AS A GENERAL ROUTE TO 18F-LABELED ARYL FLUORIDES

Article abstract of DOI:10.1016/S0022-1139(00)80525-4

The reaction of a variety of aryltrimethylsilanes with elemental fluorine and acetyl hypofluorite have been studied with the aim of developing a general method for labeling aromatic compounds with fluorine-18.Extensive 18F incorporation into the aromatic ring of the selected aryltrimethylsilanes was invariably observed, leading to the ipso(18F-for Si) electrophilic substitution products together with variable yields of other (18F-for-H) electrophilic substitution products.The relative extent of the 18F substitution processes <(C-Si/C-H)_subst.> is found to depend largely upon the substituent group on the aromatic ring of the substrate, the leaving moiety, and the radiofluoration procedure used.The utility of aryltrimethylsilyl derivates as precursors for the rapid synthesis of high specific activity of 18F-labeled radiopharmaceuticals is discussed.