Organofluorine compounds play a vital role in modern medicine ranging from pharmaceuticals to medical diagnoses. Successful fluorination methods and reagents have been developed on both laboratory and industrial scales over the past, resulting in that many fluorinated building blocks are now available for synthesizing complex organofluorine molecules as drug or drug candidates. Searching for safer and more economical fluorination methods and reagents is still important, developing new fluorination methods with widely available reagents for on-demand late-stage-fluorination of broader substrates is a paramount task in modern organofluorine chemistry. In this presentation, a new nucleophilic fluorination method that utilizes widely available electron-deficient fluoroarenes (<i>e.g.</i> tetrafluorophthalonitrile) and fluoride salts (<i>e.g.</i> KF, tetramethylammonium fluoride) to deoxyfluorinate alcohols, aldehydes, selected phenols, and carboxylic acids will be discussed. Our experimental and computational results show a correlation between deoxyfluorination reactivity and fluoride-π interaction strength. A potential implication of such correlation is that one can adjust the deoxyfluorination reactivity and selectivity by tuning the electron-deficiency of the fluoroaromatics and by preparing different combinations of the electron-deficient fluoroaromatics and fluoride salts.

Deoxyfluorination and fluoride-π interaction: What we learned from experiments and theories

Fall 2022 abstracts, posters, and presentations will launch in mid-September.

ACS Fall 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.