A versatile copper-induced synthesis of fluorinated oligo(para-phenylenes)

Ullmann-like reductive coupling of 1,4-diiodo-2,3,5,6-tetrafluorobenzene, promoted by copper(I) thiophene-2-carboxylate in N-methylpyrrolidinone at room temperature, followed by treatment with lithium aluminum hydride in THF, allowed us to obtain fluorinated poly(para-phenylene) oligomers containing up to five aromatic rings with hydrogen atoms as terminal groups.