Transition-metal-free, room-temperature radical azidofluorination of unactivated alkenes in aqueous solution

Abstract

We report herein the transition-metal-free azidofluorination of unactivated alkenes. Thus, the condensation of various alkenes with TMSN₃ and Selectfluor in aqueous CH₃CN at RT led to the efficient and regioselective synthesis of β-fluorinated alkyl azides with excellent functional group compatibility and good stereoselectivity. A single electron transfer mechanism involving the oxidative generation of azidyl radicals is proposed.