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Practical Synthesis of Polysubstituted Imidazoles via Iodine‐ Catalyzed Aerobic Oxidative Cyclization of Aryl Ketones and Benzylamines
Author(s) -
Huang Huawen,
Ji Xiaochen,
Wu Wanqing,
Jiang Huanfeng
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200582
Subject(s) - chemistry , imidazole , aryl , electrophile , catalysis , iodine , combinatorial chemistry , organic chemistry , oxidative phosphorylation , alkyl , biochemistry
A practical synthetic method for polysubstituted imidazoles via iodine‐catalyzed aerobic oxidative cyclization of aryl ketones and benzylamines has been developed. It was found to tolerate a broad range of substrates to prepare polysubstituted imidazole derivatives in a one‐pot manner, and thus importantly allowed product diversity for imidazole chemistry. Additionally, the resultant 1,2,4‐trisubstituted imidazoles could be conveniently transformed to functionalized 1,2,4,5‐tetrasubstituted imidazoles via electrophilic substitution or direct CH functionalization, or 2,4‐diaryl‐1 H ‐imidazoles by debenzylation reaction, which further indicates potential applications of this method in synthetic and pharmaceutical chemistry.