Fluoroalkylations and Fluoroalkenylations with Iodonium Salts

Synthesis and applications of fluoroalkyl and fluoroalkenyliodonium salts are summarized in this account article, focusing preferably to the reagents designed in our laboratory in the last decade. Among these reagents trifluoroethyl(aryl)iodonium salts have been used most frequently to build carbon-carbon and carbon-heteroatom bonds in simple nucleophilic substitutions and through transition metal catalyzed coupling reactions. Iodonium salts equipped with unsaturated fluorinated function showed diverse reactivity due to their electron deficient character, and these molecular motifs enable cycloadditions and nucleophilic additions to prepare fluorinated carbo- and heterocyclic molecules. Beyond the overview of existing transformations, with the presented collection, we aim to inspire future developments of iodonium reagents and their application in organic synthesis.

Automated summary

This account article summarizes the synthesis and applications of fluoroalkyl and fluoroalkenyliodonium salts, with a focus on the reagents designed in the author's laboratory in the past decade. Trifluoroethyl(aryl)iodonium salts have been frequently used to build carbon-carbon and carbon-heteroatom bonds through simple nucleophilic substitutions and transition metal catalyzed coupling reactions. Iodonium salts equipped with unsaturated fluorinated function exhibit diverse reactivity and enable the preparation of fluorinated carbo- and heterocyclic molecules through cycloaddition and nucleophilic addition reactions. The presented collection aims to inspire future developments and applications of iodonium reagents in organic synthesis.