1,6-Conjugate addition of in situ generated aryldiazenes to p -quinone methides

Herein we report a transition-metal free, base-mediated 1,6-conjugate addition of aryldiazenes to -quinone methides ( -QMs). Arylhydrazines were used for the generation of aryldiazenes using a base-mediated protocol in the presence of air as the oxidant. The 1,6-conjugate addition of aryldiazenes to -quinone methides a radical mechanism is followed by an oxidative rearrangement to furnish the desired product, arylhydrazones. Interestingly, our synthetic protocol results in the formation of an aryldiazene radical, which undergoes 1,6-conjugate addition with -QMs to furnish the arylhydrazones.