Iron-Based Imidazolium Salts as Versatile Catalysts for the Synthesis of Quinolines and 2- and 4-Allylanilines by Allylic Substitution of Alcohols

Abstract

Readily available iron(III)-based imidazolium salts have proven to be very versatile catalysts for the allylic substitution reaction of alcohols with anilines, allowing the synthesis of quinolines, 2-allylanilines and 4-allylanilines just by modulating the reaction conditions. Noteworthy, the formation of quinoline derivatives proceeds by ortho-allylation of the corresponding aniline and subsequent oxidative cyclization mediated by atmospheric oxygen. The reaction using anilines as nucleophiles is selective to the C-alkylation versus the N-alkylation, under any reaction conditions studied.