Catalyst‐Free Regioselective 1,2‐Diheterofunctionalization of Vinylferrocene

Abstract

AbstractIn this study, we report a catalyst‐free aminohalogenation process applied to vinylferrocene, employing N‐halosuccinimides (NXS; X=Cl, Br, I) as dual nitrogen and halogen sources. This 1,2‐diheterofunctionalization reaction takes place with complete regioselectivity, wherein the terminal carbon atom of the vinyl group selectively reacts with the electrophilic halogenating reagent, resulting in the formation of a cationic intermediate, which is subsequently captured by the succinimide anion. The structure of the key cationic intermediate was studied using theoretical methods. This intermediate can react with alternative nucleophiles, enabling a three‐component strategy for the synthesis of novel 1,2‐diheterofunctionalized ferrocene derivatives.