Nickel-Catalyzed Hydrofluorination of Unactivated Alkenes through a HAT Pathway

We report the hydrofluorination of unactivated alkenes using N-fluorobenzenesulfonimide as a fluorination reagent. The reaction produces exclusively Markovnikov hydrofluorination products under mild conditions. It is not affected by air or moisture and uses an inexpensive and readily available nickel compound as a catalyst. Distinct from the previously reported ionic pathway of the NiH-catalyzed hydrofunctionalization of olefins, this reaction was shown to proceed through a hydrogen atom transfer pathway.