Iron-Catalyzed ortho-Alkylation of Carboxamides

Cook et al. have reported Fe(acac)₃ catalyzed a direct ortho-alkylation of carboxamides. In this report, 8-aminoquinoline-based aryl carboxamide reacts with secondary alkyl halides or benzyl halides to give corresponding ortho-alkylated products in high yield in the presence of 1,2-bis(diphenyl-phosphino)ethane (dppe) and phenylmagnesium bromide as a Grignard reagent. The reactions are complete within 10 min, and can be performed in air with reagent-grade THF.