Copper-catalyzed nitration of electron-deficient BN-naphthalene

Abstract

Under Cu-catalysis, a regioselective nitration of 1,8-dihalogenated BN-naphthalene (ABN) compounds (4a–4c) has been established with the use of tert-butyl nitrite as the nitrating reagent. The syntheses of dihalo-ABN nitro products (6a–6c; halo = Cl, Br and I) were case-studied in conjunction with the first synthesis and characterization of diiodo-ABN compound 4c. The molecular structures of these compounds have been spectroscopically characterized and further confirmed by X-ray single crystal diffraction experiments. This method allows direct regioselective nitration of electron-deficient ABN systems, providing a step-economical entry to novel nitro-ABN structural motifs with potential applications in agrochemicals, materials sciences, and the medicinal and pharmaceutical industries.