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Facile meso Functionalization of Porphyrins by Nucleophilic Substitution with Organolithium Reagents
Author(s) -
Kalisch Werner W.,
Senge Mathias O.
Publication year - 1998
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/(sici)1521-3773(19980504)37:8<1107::aid-anie1107>3.0.co;2-z
Subject(s) - reagent , alkylation , chemistry , porphyrin , nucleophilic aromatic substitution , nucleophilic substitution , butyllithium , nucleophile , surface modification , hydrolysis , substitution reaction , combinatorial chemistry , benzoquinone , nickel , medicinal chemistry , photochemistry , organic chemistry , catalysis
The ruffle of the porphyrin increases with the number of meso substituents. (Octaethylporphyrin)nickel( II ) undergoes nucleophilic substitution reactions upon treatment with alkylating reagents such as butyllithium, hydrolysis with water, and oxidation with 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone [DDQ; Eq. (a)]. Alkylation can be achieved at all four meso positions, and access is provided to new nonplanar porphyrins and asymmetrically substituted systems.