We present our investigations into the regioselective borylation and halogenation of polyoxygenated naphthalene systems that are key precursors to dimeric pyranonaphthoquinone natural products. A variety of oxygenated naphthalenes were successfully borylated with pinacolborane in high yield and excellent regioselectivity using [Ir (COD) OMe] 2 and di-tert-butylbipyridine (dtbpy). The boronates were also readily ...