Regioselective synthesis of tetraalkynylarenes by consecutive dual sonogashira coupling reactions of the bis(triflate) of 4,5-diiodobenzene-1,2- diol

The regioselective synthesis of nonsymmetric tetraalkynylarenes has been readily achieved through consecutive sets of Sonagashira cross-coupling reactions of the bis(triflate) derivative of 4,5-diiodobenzene-1,2-diol. The initial coupling reactions proceeded with nearly complete selectivity for the reaction at the Ar-I linkages. Subsequent coupling reactions at the Ar-OTf linkages were efficiently conducted. The tetraalkynylarene products are of interest as components of organic molecular materials.