Construction of a Bicyclo[2.2.2]octene Skeleton via a Visible-Light-Mediated Radical Cascade Reaction of Amino Acid Derivatives with N-(2-Phenyl)benzoyl Groups

Bridged polycyclic ring systems constitute the core structuresof numerous natural products and biologically active molecules. Wefound that simple biphenyl substrates derived from amino acids participatein a radical cascade reaction under visible light irradiation in thepresence of [Ir{dF(CF3)ppy}(2)(dtbpy)]PF6 to enable the direct construction of bicyclo[2.2.2]octene structures.Isotopic labeling experiments suggested that intramolecular hydrogenatom transfer is involved in the cascade processes.

Automated summary

In this study, it was found that simple biphenyl substrates derived from amino acids can participate in a radical cascade reaction under visible light irradiation in the presence of [Ir{dF(CF3)ppy}(2)(dtbpy)]PF6, enabling the direct construction of bicyclo[2.2.2]octene structures. Isotopic labeling experiments suggested that intramolecular hydrogen atom transfer is involved in the cascade processes.