Advances in Nucleophilic Allylic Fluorination
Alexandre M. Sorlin, Fuad O. Usman, Connor K. English, Hien M. Nguyen
Abstract
Numerous procedures focus on inserting the fluorine atom into the carbon frameworks of synthetically useful target molecules using various nucleophilic fluorinating reagents. Among these approaches, allylic fluorination is a reaction that relies on a key carbon–fluorine bond-forming step to generate allylic fluorides. These fluorinated products can serve as building blocks for the preparation of valuable fluorine-containing synthons. Such important motifs can be found in agrochemicals, pharmaceutical agents, and PET radiotracers. Despite their prevalence and the importance of their applications, efficient methodology for their selective synthesis remains underdeveloped. Significant progress has been made in the past decade with the use of transition metals as catalysts. The search for a triad of transition metal, nucleophilic fluoride source, and leaving group enables the discovery of new allylic fluorination methods. This Perspective critically assesses recent efforts made to expand the methodology used to construct allylic C–F bonds via nucleophilic fluoride sources and provides a thorough analysis of their performance.