NaIO4-driven oxidative dimerization and Cu(i)-catalyzed oxidative decarbonylation: modular synthesis of 1,2-naphthoquinones and aryl naphtho[2,b]furans

Abstract

Sodium metaperiodate-mediated oxidative C–C homocoupling of diverse β-naphthols to 1,2-naphthoquinones in an aqueous medium, using 18-crown-6 as an additive, is reported. Subsequent Cu(I) chloride-assisted decarbonylative oxidation of these resulting 1,2-diketones under an oxygen atmosphere affords the corresponding naphthofurans in good yields. These findings demonstrate the effectiveness of orthogonal oxidative protocols in facilitating the efficient synthesis of functionalized biaryl scaffolds from readily available β-naphthols.