Hydroaminoalkylation of 1,3-dienes by dual photoredox and nickel catalysis

Abstract

A dual nickel/photoredox catalyzed hydroaminoalkylation of 1,3-dienes is presented. In this atom-economic and energetic protocol, the bulk industrial raw material isoprene and its derivatives are employed as allylic electrophile surrogates, which undergo a coupling with photoredox-generated α-amino alkyl radical species to produce valuable homoallylic amines efficiently. Preliminary mechanism experiments support the intervention of Ni-hydride species that undergo diene insertion to form Ni-allyl intermediates.