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Efficient Synthesis of Biologically Interesting 3,4‐Diaryl‐Substituted Succinimides and Maleimides: Application of Iron‐Catalyzed Carbonylations
Author(s) -
Prateeptongkum Saisuree,
Driller Katrin Marie,
Jackstell Ralf,
Spannenberg Anke,
Beller Matthias
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000369
Subject(s) - succinimides , chemistry , catalysis , carbonylation , aryl , yield (engineering) , combinatorial chemistry , organic chemistry , dehydrogenation , selectivity , materials science , alkyl , carbon monoxide , metallurgy
Abstract A straightforward two‐step synthesis of trans ‐3,4‐disubstituted succinimides through a palladium‐catalyzed Sonogashira reaction and an iron‐catalyzed double carbonylation is described. In situ oxidative dehydrogenation gave the corresponding 3,4‐diarylmaleimides. By starting from readily available aryl and heteroaryl halides, a variety of new analogues and derivatives of bioactive 3,4‐bisindolylmaleimides are obtained in good yield and selectivity.