Cyclic diaryliodonium ions: old mysteries solved and new applications envisagedDedicated to the memory of Dr Aleksandr Nikolaevich Vanchikov (1952–1998), a brilliant experimentalist, a co-author of the most exciting recent pieces of work discussed in this review, and a great friend and teacher to me during the years of my graduate studies.

Abstract

For a long time the unusually poor reactivity of cyclic diaryliodonium ions toward nucleophiles remained a mystery. Only very recently has a solution to this puzzle been found, shedding light on the mechanism of aromatic nucleophilic substitution reactions of iodonium salts. This article provides an overview of the most important current advances in the field, both theoretical and practical.