Copper-catalyzed divergent oxidative pathways of 2-naphthol derivatives: ortho-naphthoquinones versus 2-BINOLs

Abstract

Catalyst-dependent divergent pathways of 2-naphthol derivatives have been investigated. A readily available CuCl₂–DMAP catalyst system promotes the aerobic oxidation of 2-naphthol derivatives to ortho-naphthoquinones whereas switching the catalyst system to Cu(OAc)₂–DBN under an argon atmosphere allows the oxidative coupling of 2-naphthols to 1,1′-bi-2-naphthols (BINOLs) in good to excellent yields.