Metal-Catalyzed Cross-Coupling of 1,8-Diaminonaphthalene and Aryl Halides

Abstract

A new, facile, single step, methodology for the synthesis of pure 1,8- Bis(arylamino)naphthalene compounds in moderate to high yields via cross-coupling of aryl halides and 1,8-Diaminonaphthalene, employing CuI as metal and (t-bu)3P as ancillary ligand, is introduced. The new and versatile procedure was used to prepare 1,8-Bis(mxylylamino)naphthalene (77% yield) and 1,8-Bis(phenylamino)naphthlanene (54% yield) in significantly higher yields than obtained using existing methodologies (35% and 1%, respectively). 1,8-Bis(1-naphthylamino)naphthalene (32% yield) and 1,8-Bis(otolylamino)naphthalene (96% yield), previously unreported in literature, were also synthesized utilizing the new methodology.