Nucleophilic aromatic substitution of non-activated aryl fluorides with aliphatic amides

Abstract

Nucleophilic aromatic substitution (S_NAr) reactions of non-activated aryl fluorides with amide enolates are reported. The reaction proceeds under relatively mild reaction conditions. Lactams also participate in the reaction to give 2-arylated lactams. DFT calculations suggest that the reaction proceeds through a concerted S_NAr pathway.