Catalytic Iodination of the Aliphatic C-F Bond by YbI3(THF)3: Mechanistic Insight and Synthetic Utility

A facile iodination protocol, of unactivated alkyl fluorides: using catalytic amounts of YbI3(THF)(3) in the presence of iodotrimethylsilane as a stoichiometric fluoride trapping agent is presented. H-1 NMR spectroscopy demonstrates a two-step :catalytic cycle where TMSI regenerates active YbI3(THF)(3). Finally, the catalytic reaction is extended a one-pot procdure to demonstrate a potential application of the method Overall, the findings present a distinct strategy for C-F bond transformations in the presence of catalytic YbI3(THF)(3).