C-H Amination of Aromatic Compounds Based on Electrochemical Oxidation

We have developed a new method for synthesizing aromatic primary amines from 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 transformation serves as a powerful method for C−H amination of aromatic compounds without using metal catalysts and harsh chemical reagents. Synthetic utility of the method is demonstrated by C−H amination of aromatic compounds bearing a nitro group to give a key intermediate for the synthesis of bioactive compounds such as a VLA-4 antagonist.