Oxidative Annulation of β-Aminoporphyrins into Pyrazine-Fused Diporphyrins


  • This work at Nagoya University was supported by Grant-in-Aids for Scientific Research (no. 23655033 and no. 22750036) from MEXT (Japan) and the Global COE program in Chemistry of Nagoya University. H.S. acknowledges the Toray Science Foundation for financial support.


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Dimers are a girl's best friend: The oxidative fusion reaction of β-aminoporphyrins with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) under high-dilution conditions furnishes pyrazine-fused diporphyrins 1 in high yields. In a further application of the reaction, the oxidation of a 5,10,15,20-tetraphenylporphyrin derivative provides a singly linked diaminodiporphyrin 2 along with the pyrazine-fused diporphyrin (see scheme; only core structures are shown).