Nucleophilic coupling of alkali 2-naphthoxides with 1-bromo-2 naphthols. Ion-pairing and halogen dance in the formation of 1,1′-binaphthalene-2,2′-diols

A very pronounced effect of solvent and cation has been found in the investigated reaction, indicating that ion-pairing is indispensable in the title product formation. A simple rationale has been provided assuming self assembly of the complementary reactants driven by hydrogen bonding and ion-pairing interactions. Concomitantly, halogen exchange between the reaction partners has been demonstrated to be a concurrent pathway, resulting from the nucleophilic 2-naphthoxide attack at the bromine terminus of the Cα–Br bond in the participating 1-bromo-2-naphthol.