Fe(III)/NaBH4-Mediated Free Radical Hydrofluorination of Unactivated Alkenes

Abstract

A powerful Fe(III)/NaBH₄-mediated free radical hydrofluorination of unactivated alkenes is disclosed using Selectfluor reagent as a source of fluorine and resulting in exclusive Markovnikov addition. In contrast to the traditional and unmanageable free radical hydrofluorination of alkenes, the Fe(III)/NaBH₄-mediated reaction is conducted under exceptionally mild reaction conditions (0 °C, 5 min, CH₃CN/H₂O). The reaction can be conducted open to the air and with water as a cosolvent and demonstrates an outstanding substrate scope and functional group tolerance.