Rhodium(III)-catalyzed oxidative mono- and di-olefination of isonicotinamides.

[RhCp*Cl(2)](2) can catalyze the oxidative coupling of secondary isonicotinamides with activated olefins using Cu(OAc)(2) as an oxidant. The selectivity can be controlled by the solvent. In MeCN, the mono-olefination and two-fold oxidation reaction is the major pathway, while in THF this reaction gave mostly diolefination products. In both cases, the coupled products contain an exocyclic C=C bond.