Reinvestigation of the Pummerer arylation of quinones: a selective approach to 2,2′,5′-trihydroxybiaryls

Abstract

A reinvestigation of the Pummerer arylation of quinones in light of the metal-template catalysis has provided a direct and selective route to 2,2′,5′-trihydroxybiaryls 7, a class of compounds useful in the synthesis of polycyclic natural products. Compounds 7 are readily synthesized by mixing dichloroaluminium phenolates 8 with a slurry of the 1 : 2 adduct formed between p-benzoquinone and AlCl₃ in CS₂(room temp., 4 h).