Iron-Mediated Reductive Amidation of Triazine Esters with Nitroarenes

Org Lett. 2024 Jan 12;26(1):416-420. doi: 10.1021/acs.orglett.3c04180. Epub 2023 Dec 31.

Abstract

A reductive amidation of triazine esters with nitroarenes by using cheap iron as a reducing metal in the presence of TMSCl in DMF was developed. The reactions proceeded efficiently under transition metal-free conditions to give the corresponding amides in moderate to good yields with good functional group compatibility. Preliminary mechanistic investigations indicated that nitrosobenzene, N-phenyl hydroxylamine, azoxybenzene, azobenzene, aniline, and N-arylformamide possibly served as the intermediates of the reaction.