Hydrofluorination of Alkenes: A Review

Abstract

In this minireview, we explore the different approaches used to perform the hydrofluorination reaction of alkenes. Contrary to other hydrohalogenation reactions, the hydrofluorination requires specific conditions due to the lower reactivity of HF. Over the years, many different approaches have been explored among which the use of HF complexes has particularly proved to be useful as these reagents are easier to handle. The enantioselective hydrofluorination has been demonstrated using electrophilic sources of fluorine, while radical fluorination proved compatible with a vast range of functional groups that are generally problematic with strong acids and some fluoride sources. This review will cover the different conditions developed through the years, starting with the first reported addition using gaseous HF, up to the most recent method described in October 2020.

Keywords: alkene; hydrofluorination; hydrogen fluoride; organofluorine compounds; synthetic methodologies.