Palladium-Catalyzed Annulation Reaction of Bay-Iodobiphenyls with Maleimides to Access 9,10-Phenanthrenedicarboximides

J Org Chem. 2025 Jan 10;90(1):401-411. doi: 10.1021/acs.joc.4c02359. Epub 2024 Dec 17.

Abstract

A palladium-catalyzed annulation reaction of bay-iodobiphenyls with maleimides was developed. This approach allows for the efficient synthesis of a variety of 9,10-phenanthrenedicarboximides, particularly polyalkoxy-substituted 9,10-phenanthrenedicarboximides with potential liquid-crystalline properties. Research findings indicate that the resulting product, N-hexyl-2,3,6,7-tetrakis(hexyloxy)-9,10-phenanthrenedicarboximide, exhibits promising, good liquid-crystalline properties.