The palladium(II)-catalysed carbon-carbon-coupling reaction (Heck reaction) between a variety of metalated beta-monohalosubstituted porphyrins (2-bromotetraphenylporphyrin, 2-bromo-3,7,8,12,13,17,18-heptaethylporphyrin, and 3(8)monoiodo-deuterporphyrin IX dimethyl ester) and a series of terminally substituted acetylenic derivatives, is reported. A few disubstituted porphyrin analogs were also synthesized using the corresponding beta-dihalogenated porphyrin precursors.