Alpha-heteroarylation of esters, lactones, amides, and lactams by nucleophilic aromatic substitution.

ABSTRACT

[reaction see text] A mild and efficient alpha-heteroarylation of simple esters and amides was developed via nucleophilic aromatic substitution. The choice of NaHMDS in toluene gave the best results. A tandem alpha-heteroarylation and hydroxylation protocol using air as the oxidant afforded tertiary alcohols in good yields.