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A Facile and Reliable Method for the Synthesis of Tetrabenzoporphyrin from 4,7‐Dihydroisoindole
Author(s) -
Filatov Mikhail A.,
Cheprakov Andrei V.,
Beletskaya Irina P.
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700014
Subject(s) - chemistry , isoindole , bottleneck , combinatorial chemistry , characterization (materials science) , key (lock) , stereochemistry , nanotechnology , computer science , materials science , embedded system , computer security
A new route to tetrabenzoporphyrins from the closest possible precursor of the unstable isoindole was developed. A key feature of this route is a dramatic facilitation of thearomatization of annelated rings, which is the most serious bottleneck in previous syntheses of tetrabenzoporphyrins. The capabilities of the new method are illustrated by the synthesis of meso ‐tetraaryltetrabenzoporphyrins, as well as the first unambiguous synthesis and characterization of 5,15‐diphenyltetrabenzoporphyrin.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)