tert-Butylhydroperoxide mediated radical cyanoalkylation/cyanoalkenylation of 2-anilino-1,4-naphthoquinones with vinylarenes/arylalkynes and azobis(alkylcarbonitrile)s

Abstract

A novel sustainable methodology based on one-pot cyanoalkylation/cyanoalkenylation of 2-anilino-1,4-naphthoquinones with vinylarenes/arylalkynes and azobis(alkylcarbonitrile)s involving a three-component radical cascade pathway has been achieved. Here, tert-butylhydroperoxide (TBHP) acts as an efficient oxidant, and it smoothly drives the reaction, producing the three-component products in very good to excellent yields. This cascade reaction eliminates the use of any base, additive, metal and hazardous cyanating agent. Additionally, this protocol exclusively delivers a stereospecific product in the case of arylalkynes. The involvement of radicals is evidenced through various radical trapping experiments.