A convenient synthesis of β,β’-dioxochlorins: New application for Bobbitt's salt

Oxidation of β-aminoporphyrins with 4-acetamido-2,2,6,6-tetramethylpiperidine−1-oxoammonium tetrafluoroborate (Bobbitt's salt) provides an efficient synthesis of the corresponding 2,3-dioxochlorins. The synthesis is simple and exhibit good universality. In addition, Bobbitt's salt can be further applied to oxidize more aromatic amines. Preliminary studies have shown that aromatic amines with structures similar to 9-aminophenanthrene can be selectively oxidized to corresponding ortho-diketones.