A direct
C–H cyanoalkylation of heteroaromatic <i>N</i>-oxides
and quinones with cyclobutanone oximes is reported. This
redox-neutral, operationally simple cyanoalkylation reaction is successfully
amenable to a wide range of heteroaromatic <i>N</i>-oxides,
quinones, and cyclobutanone oximes. A novel catalytic system consisting
of a nickel source proved crucial for cleavage of the C–C bond
of cyclobutanone oximes and for selective C–C bond formation
over β-hydride elimination. Mechanistic studies suggest that
a radical intermediate might be involved in this transformation
