title: Heterocyclization Approach for Electrooxidative Coupling of Functional Primary Alkylamines with Aromatics.
abstract: A new approach for electrooxidative coupling of aromatic compounds and primary alkylamines bearing a functional group such as a hydroxyl group and an amino group was developed. The key to the success of the transformation is heterocyclization of functional primary alkylamines. Treatment of primary alkylamines bearing a functional group with nitriles or their equivalents gives the corresponding heterocycles. The electrochemical oxidation of aromatic substrates in the presence of the heterocycles followed by chemical reaction under nonoxidative conditions gave the desired coupling products.
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.affiliation: Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan.
authors.forename: Akihiro
authors.initials: A
authors.lastname: Shimizu
authors.affiliation: Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan.
authors.forename: Jun-ichi
authors.initials: J
authors.lastname: Yoshida
mesh_terms: D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004563:Electrochemistry; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: D000588:Amines; D006841:Hydrocarbons, Aromatic