Directed nucleophilic aromatic substitution reaction†

Abstract

In this study, we discovered a directed nucleophilic aromatic substitution reaction, “directed SNAr (dSNAr),” in the reaction of ortho-iodobezamides and amine in the presence of pyridine. The reaction proceeded ortho-specifically and did not require a strong electron-withdrawing group on the arene substrate. Most reactions proceeded at room temperature in the presence of Py, and a wide range of amine nucleophiles can be applied. Furthermore, the reactions with benzamide substituted with multiple halogens were found to be 100% ortho-selective.