Iodine(III)-Mediated para-Selective Direct Imidation of Anilides

Abstract

The direct, nucleophilic imidation of acetanilide derivatives has been performed under mild, iodine(III)-mediated or -catalyzed conditions, employing lithium triflimide as the nitrogen source. The reaction exhibits exclusive regioselectivity for the para position and shows a good tolerance for varied functional groups at both the ortho or meta positions. Preliminary mechanistic data suggest that the LiNTf2 reagent plays a key role in the reactivity.

Keywords: CN bond formation; hypervalent iodine; oxidative coupling; para-phenylenediamines; umpolung.