title: Direct C-N coupling of imidazoles with aromatic and benzylic compounds via Electrooxidative C-H functionalization.
abstract: A method for the C-N coupling of imidazoles based on electrooxidative C-H functionalization of aromatic and benzylic compounds has been developed. The key to the success is the formation of protected imidazolium ions as initial products, avoiding overoxidation. Deprotection under nonoxidative conditions affords N-substituted imidazoles. Various functional groups are compatible with the present transformation. To demonstrate the power of the method, a P450 17 inhibiter and an antifungal agent having N-substituted imidazole structures were synthesized.
authors.affiliation: Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University , Nishikyo-ku, Kyoto 615-8510, Japan.
authors.forename: Tatsuya
authors.initials: T
authors.lastname: Morofuji
authors.forename: Akihiro
authors.initials: A
authors.lastname: Shimizu
authors.forename: Jun-ichi
authors.initials: J
authors.lastname: Yoshida
mesh_terms: D001554:Benzene / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D006859:Hydrogen / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry*; D009584:Nitrogen / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: D007093:Imidazoles; D002244:Carbon; C029899:imidazole; D006859:Hydrogen; D001554:Benzene; D009584:Nitrogen