Synthesis of Biaryl Carboxylic Acids through a Cascade Suzuki-Miyaura Coupling/Friedel-Crafts Alkylation/Lewis-Acid-Catalyzed Rearrangement/Aromatization Process.

Abstract

In this study, we present a series of 1,3-dicarbonyls that can undergo a cascade Suzuki coupling, followed by a Friedel-Crafts reaction to produce molecules containing polycyclic alcohols. These polycyclic alcohols can then be converted into biaryl carboxylic acids through ring-opening rearrangement reactions catalyzed by a Lewis acid. The Friedel-Crafts reaction exhibits selective para-positioning of the hydroxyl group and demonstrates good compatibility with functional groups with a yield of up to 82%. Substrates with substituted hydroxyl groups can also be converted into biaryl carboxylic acids through a Lewis-acid-catalyzed ring-opening rearrangement.