Ni-catalyzed cross-electrophile coupling of α-hydroxy carbonyl compound-derived oxalates with vinyl triflates

[Display omitted] •Efficient nickel-catalyzed reductive coupling reactions.•Low toxic C–O electrophiles serving as coupling partners.•High-yielding synthesis of β,γ-unsaturated carbonyl compounds. A nickel-catalyzed reductive vinylation of α-hydroxy carbonyl compound-derived C–O electrophiles to access β,γ-unsaturated carbonyl compounds is reported here. By this method, a library of vinyl triflates can serve as vinylating reagents, while various alkyl oxalates undergo C–O bond fragmentation to provide α-carbonyl radicals. This work expands the scope of cross-electrophile coupling reactions that employ two low toxic C–O electrophiles as coupling partners.