title: Electrochemical C-H amination: synthesis of aromatic primary amines via N-arylpyridinium ions.
abstract: We have developed a new method for C-H amination of aromatic compounds based on electrochemical oxidation of aromatic compounds in the presence of pyridine followed by the reaction of the resulting N-arylpyridinium ions with an alkylamine. This new transformation serves as a powerful method for synthesizing aromatic primary amines from aromatic compounds without using metal catalysts and harsh chemical reagents. High chemoselectivity of the present method is demonstrated by C-H amination of aromatic compounds bearing a nitro group to give a key intermediate for the synthesis of VLA-4 antagonist.
authors.affiliation: Department of Synthetic Chemistry, 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: D000586:Amination; D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D004563:Electrochemistry; D039041:Integrin alpha4beta1 / Q000037:antagonists & inhibitors; D007477:Ions; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011726:Pyridinium Compounds / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D000588:Amines; D039041:Integrin alpha4beta1; D007477:Ions; D011726:Pyridinium Compounds