Photocatalytic C(sp2)–OMe bond cleavage and amidation of anisoles with N-hydroxyphthalimides and phthalimides

Abstract

The cleavage of the inert C(sp²)–OMe bond via photocatalysis is an attractive alternative to the well-established Ni-catalyzed methods, and is also a challenge in organic chemistry. Herein we report a metal-free photocatalytic C(sp²)–OMe bond cleavage strategy using 4CzIPN as a mild oxidizing photoredox catalyst. N-Hydroxyphthalimides and phthalimides are effective coupling reagents for this C–O bond cleavage and amidation of anisoles, as evidenced by 48 examples. PhthN radical and arene radical cation pathways are suggested for the amidation of anisoles with N-hydroxyphthalimides and phthalimides, respectively.