The cleavage of aryl-metal bonds by elemental fluorine: synthesis of aryl-fluorides

Abstract

The reaction of elemental fluorine with phenyl derivatives of tin, lead, germanium, silicon, mercury, and thallium has been studied with the aim of developing a general method for labelling aromatic compounds with radioactive 18F. Rapid synthesis of fluorobenzene was achieved in varying chemical yields up to 70%, depending largely upon the metal substrate used, with aryl–tin compounds giving the highest yields. Radiochemical yields are also given for the synthesis of 18F-fluorobenzene from the cleavage of aryl–tin bonds with 18F-F2.