One-pot syntheses of macrocycles 1 and 2 (Scheme 1) were accomplished by reacting the commercially available 1,2-diiodo-3,4,5,6-tetrafluorobenzene (3) with diynes 4 and 5, which themselves were prepared following literature procedures. Macrocycle 1 was isolated as a brown solid in 22% yield after successive recrystallizations from PhMe/Me2CO and PhMe/MeCN solvent systems. Macrocycle 2 was obtained after column chromatography eluting with DCM/hexanes as a white solid in 5% yield. Their relatively low yields were caused by the presence of side products which were either linear uncyclized oligomers or the reduced unreactive materials in which the arylappended iodine atom was replaced with a hydrogen. These side products were not isolated, but the one-step synthesis allowed the preparation of sufficient amounts of 1 and 2.