Regioselectivity for nucleophilic substitutions of aryl halides with DMF in deep eutectic solvent

Abstract

Deep eutectic solvent-promoted substitution of aryl halides with N,N-dimethylformamide (DMF) has been developed in this report. The process was successful obtained a wide range of N,N-dimethylaniline compounds from different substrates in moderate to good yields (52 %–93 %) and exhibited specific regioselectivity in the para position. The possible mechanism to explain the regioselectivity was that the para halogen atom of electron-withdrawing group possessed a less spatial resistance, and the stability of the transition states forming ortho-substituted products was destructed due to the hydrogen bonds between deep eutectic solvent and aryl halides. This work was expected to provide a useful guidance for enhancing nucleophilic substitution reactivity of halogen atoms in the para-position of an electron-withdrawing group.