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.
1521-3773/asset/2002_left.gif?v=1&s=ac6b0d94a94d7ce7a210002b8096b42feffc0bcf)
1521-3773/asset/olbannercenter.gif?v=1&s=c083e1920cd41ed129901c116018eab93b5ad3c4)
1521-3773/asset/2002_right.gif?v=1&s=451042aa3415ae3ad0729984d26dee1866aca82e)
Communication
Oxidative Annulation of β-Aminoporphyrins into Pyrazine-Fused Diporphyrins†
Article first published online: 8 FEB 2012
DOI: 10.1002/anie.201108037
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Akita, M., Hiroto, S. and Shinokubo, H. (2012), Oxidative Annulation of β-Aminoporphyrins into Pyrazine-Fused Diporphyrins . Angew. Chem. Int. Ed., 51: 2894–2897. doi: 10.1002/anie.201108037
- †
Publication History
- Issue published online: 13 MAR 2012
- Article first published online: 8 FEB 2012
- Manuscript Received: 15 NOV 2011
- Manuscript Revised: 5 JAN 2011
Funded by
- MEXT
- Nagoya University
- Toray Science Foundation
Keywords:
- fused-ring systems;
- oxidation;
- porphyrinoids;
- pyrazines
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).