Copper-catalyzed [1,3]-alkoxy rearrangement for the selective synthesis of polycyclic ortho-aminoarenol derivatives

Abstract

Copper-catalyzed [1,3]-alkoxy rearrangement reactions of polycyclic arenes, such as naphthalenes and phenanthrenes, proceeded efficiently to afford the corresponding ortho-aminoarenol derivatives in good to excellent yields with excellent ortho-selectivity. Through appropriate choice of an N-heterocyclic carbene (NHC) ligand, the reactions are applicable to not only a methoxy group but also readily deprotectable p-nitrobenzyloxy and methoxymethoxy groups. Moreover, the rearrangement of the N-methoxyamino group on the benzene ring of indoles proceeded efficiently, affording the corresponding functionalized indoles in a site-selective manner.