A series of aryl ether oligomers end-capped with ethynyl groups have been synthesised via a three-step process, ie iodination of oligo-aryl ethers, nucleophilic substitution of the iodide group with 2-methyl-3-butyn-2-ol catalysed by Pd/Cu and subsequent deacetonation in KOH/toluene. Effects of reaction temperature and the Pd/Cu catalyst on iodination and the substitution reaction are discussed.