Synthesis of meta-substituted aniline derivatives by nucleophilic substitution

Article abstract of DOI:10.1016/S0040-4020(99)00818-2

Substitution by amines of fluorobenzenes containing a meta- substituted electron withdrawing group (EWG), in DMSO at 100 °C over 60 h gave meta-substituted aniline derivatives in isolated yields of up to 98%. The scope of the reaction is explored in terms of reaction conditions and substrates. It is postulated that facile meta-substitutions are facilitated through field stabilisation of the intermediate anion by EWG substituents.