An efficient synthesis of 2,2'-diamino-1,1'-binaphthalene (2) from 2-naphthylamine (1) was carried out at room temperature in methanol by copper-amine mediated oxidative coupling [x(CuCl_2):x(benzylamine or ethanolamine) = 2:1, equivalent to 1] for 2 hours. The precipitated complex of 2-CuCl_2 was separated and decomposed to give 2 in 74% yield. The oxidant was CuCl_2-amine while O_2 regenerated Cu(II) by oxidizing the Cu(I) species. The aerobic oxidation of 1 at room temperature in methanol under the catalysis of cupric salt [Cu(ClO_4) _2, Cu(NO_3)_2 or Cu(OAc)_2] resulted in 2-amino-1,4- naphthoquinone-4- 2'-naphthylimide (3) with high yield up to 86%. X-Ray single crystal diffraction analysis of the acetylized product of 3 shows that its structure is 2-acetoamino-1,4-naphthoquinone-(E)-4-2'-naphthylimide (4) . Cyclic voltammetry analysis suggests that the selectivity of the oxidation of 1 can be related to the reductive potentials of the copper(II) compounds. The fact that under anaerobic condition 1 is inert to Cu(ClO_4)_2, Cu(NO_3)_2 or Cu(OAc)_2 infers that O_2 acts as the electron acceptor and is activated by Cu(II) to oxidize 1. ESI-MS analysis indicates that the intermediate is 1,2- naphthoquione-2-imide (6), which forms 3 via addition with 1 followed by oxidation.

Key words: NAPHTHALENEAMINE P, COPPER COMPLEX, OXIDATION, COUPLING REACTION, CYCLOVOLTAMGRAPH, NAPHTHQUINONE P, IMINE