Palladium-Catalyzed Annulation Reaction of Bay-Diiodinated Arenes with o-Chloroaromatic Carboxylic Acids to Access Polycyclic Aromatic Compounds

Abstract

A palladium-catalyzed annulation reaction of bay-diiodinated arenes with o-chloroaromatic carboxylic acids was established. This approach enables the synthesis of a variety of polycyclic aromatic compounds, especially polyalkoxy-substituted polycyclic aromatic compounds, frequently found in discotic liquid-crystalline materials. The investigations indicate that the product 2,3,8,9,12,13-hexakis(hexyloxy)-5-azadibenzo[fg,op]tetracene demonstrates favorable room-temperature liquid-crystalline properties.