Organic chemists commonly use palladium catalysis to create carbon-carbon bonds. We utilized palladium to catalyze the γ-arylation of α, β-unsaturated ketones, and esters. This work expands on palladium-catalyzed α-arylation chemistry and extends it to the vinylogous variation at the γ-arylation position. We reported the synthesis of γ-arylated 7-methoxy-4-methylcoumarin, which achieved mono-γ-arylation regioselectivity. We report efforts towards applying our reaction conditions to other α,β-unsaturated ketones and esters to expand the scope of our reaction conditions.
We also utilized palladium to catalyze the enantioselective asymmetric Heck reaction to produce potentially bioactive phenanthidinone analogs. We achieve this through the Birch-Heck sequence, a 5-step sequence that includes Birch reduction/alkylation of benzoic acid, acid chloride formation/amide formation, triflation, and then the enantioselective Mizoroki-Heck reaction. In this process, we report N-H and N-Me phenanthridinone analogs' synthesis, which may have bioactivity. A protection/deprotection protocol was found to be the key to accessing phenanthridinone derivatives with N-H.