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 aqueous medium, using 18-crown-6 as an additive, is reported. Subsequent Cu(I) chloride-assisted decarbonylative oxidation of the resulting 1,2-diketones under an oxygen atmosphere affords the corresponding naphthofurans in good yields. The final outcome highlights the efficiency of these orthogonal oxidative protocols for the streamlined synthesis of functionalized products from readily accessible β-naphthols.