Nickel-Catalyzed Hydrofluorination Of Unactivated Alkenes

Fluorinated organic molecules are widely used in medicinal chemistry and life science.Owing to the small Van der Walls radius and strong electronegativity,fluorinated organic molecules have unique chemical bioactivity and chemical-physical stability.Hence fluorination of drug candidates is a good method to modify the lipophilicity or electron density of a molecule without presenting a major steric perturbation in it.Latest reports show that 20% of the drug molecules and 35% of the agrochemicals contain at least one fluorine atom.It is important to develop new methodology to introduce a fluorine atom into an organic molecule.Here we report a nickel-catalyzed reductive hydrofluorination process of unactivated alkenes using N-fluorobenzenesulfonimide as the fluorination reagent.Markovnikov hydrofluorination products were obtained under mild conditions.The reaction is not sensitive to air or moisture.Different from the previously proposed ionic pathway in NiH-catalyzed alkene hydrofunctionalization,the reaction here was proposed to proceed through a hydrogen atom transfer(HAT)pathway.