Initial investigations focused on the synthesis of dibromide 3a, driven by ongoing research in the synthesis of electronically-differentiated macrocycles (Scheme 1). A screen of various reaction conditions quickly led to the identification of optimal conditions (Table 1, entry 6): tetrahydrofuran (THF) solvent, 2.2 equiv of DBDMH and triphenylphosphine, 2 h reaction time, and a reaction temperature of 0 C to room temperature.