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Oxidative Annulation of β‐Aminoporphyrins into Pyrazine‐Fused Diporphyrins
Author(s) -
Akita Masanari,
Hiroto Satoru,
Shinokubo Hiroshi
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201108037
Subject(s) - pyrazine , annulation , chemistry , oxidative phosphorylation , tetraphenylporphyrin , derivative (finance) , photochemistry , medicinal chemistry , azulene , stereochemistry , organic chemistry , porphyrin , catalysis , biochemistry , financial economics , economics
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).