A sulfinate-azide hybrid reagent for sequential radical fluoroalkylation and click reaction.

A new clickable radical fluoroalkylating reagent, sodium 2-azido-1,1,2,2-tetrafluoroethanesulfinate, was prepared in one step from tetrafluoroethylene, sodium azide and sulfur dioxide. Oxidant-induced radical fluoroalkylation of arenes, heteroarenes, alkenes, and thiols, using this reagent, afforded azidotetrafluoroalkylated adducts. Their subsequent click reactions with alkynes led to N-fluoroalkylated triazoles. The synthetic sequence demonstrated the use of the new reagent as a clickable azidotetrafluoroethyl radical synthon, enabling connection to a diverse array of moieties, including a monoclonal antibody, via a triazole linker.