Transition-Metal-Free, Room-Temperature Radical Azidofluorination of Unactivated Alkenes in Aqueous Solution

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.