Intramolecular cyclization using palladium-catalyzed arylation toward formyl and nitro groups

Article abstract of DOI:10.1016/S0040-4039(99)00185-9

Intramolecular arylation of properly designed substrates bearing a formyl or nitro terminating group was achieved employing a PdCl₂(Ph₃P)₂- Cs₂-CO₃ catalyst system to form various carbocyclic compounds. Arylation toward the formyl group occurred at the α-position (α-arylation) or at the carbonyl carbon (carbonyl-arylation) depending on the structure of the substrates and on the reaction solvent. The α-arylated secondary nitro group was partially transformed to ketone, whereas the tertiary nitro group was partially eliminated to a styrene type of olefin.