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Synthesis of 1,2‐Diaryl‐ and 1‐Aryl‐2‐alkylimidazoles with Sterically Demanding Substituents
Author(s) -
Micksch Maik,
Tenne Mario,
Strassner Thomas
Publication year - 2013
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.201300688
Subject(s) - chemistry , steric effects , aryl , imidazole , benzoic acid , metal , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , alkyl
1,2‐Diarylimidazoles are an important class of compounds. They are frequently used as ligands for photophysically active metal complexes and also display physiological activity. We developed a new, high‐yielding procedure for the synthesis of 1,2‐diaryl‐substituted imidazoles with sterically demanding substituents at the respective ortho positions by starting from commercially available anilines and benzoic acids through the corresponding acid chlorides. The metal‐free method provides access to a variety of different substituents on the phenyl rings at N‐1 and C‐2 as well as at the 4,5‐positions of the imidazole backbone. Our new method is also suitable for the preparation of 1‐aryl‐2‐alkylimidazoles.