C–H, Si–H and C–F abstraction with an extremely electron poor I(iii) reagent

Abstract

The recently discovered I(III) reagent NO₂-C₆H₄-I(OTf)₂ is found to rapidly react with hydride sources, including HSiEt₃ and relatively hydridic C–H precursors. These represent the first distinct reactions involving direct hydride abstraction by I(III) under ambient conditions. Direct C–F abstraction is also demonstrated, as well as oxidation of cyclic alkenes to aromatic rings, all representing new reactions for I(III) demonstrating the very high reactivity of NO₂-C₆H₄-I(OTf)₂.