Dual Ni/Organophotoredox Catalyzed Allylative Ring Opening Reaction of Oxabenzonorbornadienes and Analogs

A general approach for the allylation of oxa- and azabenzonorbornadienes is reported by merging organophotoredox and nickel catalysis. This methodology allowed the diastereoselective allylation of various heterocyclic alkene derivatives with a broader range of allylic acetate compounds compared to previously published procedures. Moreover, no air-sensitive organometallic species and no metal reductants (such as zinc or manganese) are required for the ring opening. Mechanistic studies suggest that the ring opening proceeds through a carbometalation process.