Synthesis of diaryliodonium salts for use in nucleophilic substitution reactions

Abstract

Diaryliodonium salts are a type of hypervalent iodine compound that are capable of arylating a variety of nucleophiles. Unsymmetrical diaryliodonium salts provide varying degrees of selectivity during reactions with nucleophiles where one aryl group is preferentially transferred to the nucleophile. It is the goal of this research to develop a diaryliodonium salt where the substituents on one of the aryl groups are modified in such a manner that it causes a nucleophile to couple with the other aryl group with >95% selectivity. This research finds practical application as it relates to Positron Emission Tomography (PET). Positron Emission Tompgraphy is an area of molecular imaging that is used to visualize human physiology by the detection of positron-emitting radiopharmaceuticals labeled with short lived positron-emitting radionuclides. Recent research has focused on efficiently introducing the [18F]fluoride ion into an aryl group of diaryliodonium salts.