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Controlled Regioselective Amination of Peryleneimides
Author(s) -
George Lijo,
Ahmed Zafar,
Lemmetyinen Helge,
Efimov Alexander
Publication year - 2015
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.201403299
Subject(s) - amination , chemistry , imide , regioselectivity , perylene , organic chemistry , bay , combinatorial chemistry , catalysis , molecule , civil engineering , engineering
Perylenediimides (PDIs) and perylenemonoimide diesters (PMIs) can be selectively substituted at the 1,6‐ or 7,12‐ positions of the bay region, respectively, by direct amination reactions. The reactions proceed by the formation of a perylene radical anion and its subsequent oxidation, and the yields range from 20–97 %. The amination can be tuned to obtain either mono‐ or disubstituted perylenes by varying the oxidants involved. The presence of the imide cycle is crucial for the transformation, although the amination occurs regioselectively at the bay‐region positions distant from the imide cycle.