The reaction of arynes with münchnones: synthesis of isoindoles and azaisoindoles

Arynes derived from silyltriflate precursors undergo a smooth 1,3-dipolar cycloaddition with münchnones to furnish isoindoles and azaisoindoles in moderate to high yields. Modification of the fluoride source, solvent, and temperature allows for the selective generation of either isoindoles or benzanthracenimines, the latter of which serve as precursors to polycyclic aromatic hydrocarbons.