Versatile Synthesis of Symmetric and Unsymmetric Imines via Photoelectrochemical Catalysis: Application to N-Terminal Modification of Phenylalanine

A strategy that combines electrochemical synthesis and photoredox catalysis was reported for the efficient synthesis of imines. This approach was demonstrated to be highly versatile in producing various types of imines, including symmetric and unsymmetric imines, by exploring the impact of different substituents on the benzene ring of the arylamine. Additionally, the method was specifically applied to modify N-terminal phenylalanine residues and was found to be successful in the photoelectrochemical cross-coupling reaction between NH2-Phe-OMe and aryl methylamines, leading to the synthesis of phenylalanine-containing imines. Therefore, this technique would present a convenient and efficient platform for synthesizing imines, with promising applications in chemical biology, drug development, and organic synthesis. A photoelectrochemical strategy for synthesizing imines efficiently is introduced, including both symmetric and unsymmetric imines. Of note, the method is successfully applied to perform the cross-coupling of N-terminal phenylalanine residues, highlighting its potential in chemical biology applications. This strategy presents a convenient platform for imine synthesis with broad implications in drug development and organic synthesis.image

Automated summary

This study reported a strategy that combines electrochemical synthesis and photoredox catalysis for the efficient synthesis of imines. The approach showed high versatility in producing symmetric and unsymmetric imines by exploring different substituents on the benzene ring. Specifically, the method was successfully applied to modify N-terminal phenylalanine residues, demonstrating its potential in chemical biology applications. This technique provides a convenient and efficient platform for imine synthesis with broad implications in drug development and organic synthesis.