Rhodium(I)-Catalyzed C8-Alkylation of 1‑Naphthylamide Derivatives with Alkenes through a Bidentate Picolinamide Chelation System

The rhodium­(I)-catalyzed
C–H alkylation of 1-naphthylamide
derivatives with alkenes at the C8-position using a picolinamide directing
group is reported. Various alkenes including styrene derivatives,
α,β-unsaturated carbonyl compounds, and even unactivated
alkene could also be used as coupling partners. The reaction mechanism
was investigated in kinetic studies, deuterium labeling studies, and
control experiments. The reaction appears to proceed through a rhodium
carbene intermediate, which is generated from an alkene.