Synthesis of Biaryl Carboxylic Acids through a Cascade
Suzuki–Miyaura Coupling/Friedel–Crafts Alkylation/Lewis-Acid-Catalyzed
Rearrangement/Aromatization Process
posted on 2024-02-29, 14:04authored byShaodong Liu, Liang Cheng, Li Liu
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.