A Three-Step Process To Facilitate the Annulation of Polycyclic Aromatic Hydrocarbons

A new
efficient three-step process to annulate polycyclic aromatic
hydrocarbons (PAHs) has been developed, providing access to PAHs with
saturated rings that under current chemical methods would be difficult
to produce in an efficient manner. This method relies on a palladium-catalyzed
cross-coupling reaction of various brominated PAHs with cyclohexanone
to yield α-arylated ketones, which are converted to regiospecific
vinyl triflates and cyclized by a palladium-catalyzed intramolecular
arene–vinyl triflate coupling to produce PAHs with incorporated
saturated rings or “tetrahydroindeno-annulated” PAHs.