A new synthetic approach to porphyrin-α-diones and a -2,3,12,13-tetraone: building blocks for laterally conjugated porphyrin arrays

Abstract

We report the first use of the Dess–Martin periodinane (DMP) for the oxidation of an arylamine to an α-dione. The methodology is illustrated by the preparation of free-base and metal chelated porphyrin-α-diones in up to 52% yield by oxidation of 2-aminoporphyrins with the DMP. We also found that DMP could be used to oxidise a 2,3-diaminoporphyrin to a porphyrin-α-dione in good yield with other free-base diaminoporphyrin isomers forming a trans-porphyrintetraone in 20% yield.