1,2-Dicarba-closo-dodecaboran-1-yl Naphthalene Derivatives

1,2-Dicarba-closo-dodecaboranes (o-carboranes) and naphthalenes have potential value as components or building blocks for supramolecular systems. We have efficiently synthesized 1-(1,2-dicarba-closo-dodecaboran-1-yl)naphthalene and 2-(1,2-dicarba-closo-dodecaboran-1-yl)naphthalene derivatives by employing three preparative methods: cyclization of the corresponding acetylenes with decaborane(14), an Ullmann-type coupling reaction of carboranes with aryl halide, and the aromatic nucleophilic substitution (S(N)Ar) reaction of aryl-o-carboranes with nitrophenyl halide. The optimum conditions of each method for synthesis of the title compounds were also investigated.