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

Chemical Communications Pub Date: 2022-08-09 DOI: 10.1039/D2CC02999E

Abstract

Nucleophilic aromatic substitution (SNAr) 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 SNAr pathway.

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