Cu(II)-Catalysed Hydrocarboxylation of Imines Utilizing CO₂ to Synthesize α-Unsaturated Aminocarboxylic Acids

• Main Authors: Allen T. Gordon (Author), Eric C. Hosten (Author), Adeniyi S. Ogunlaja (Author)
• Format: Book
• Published: MDPI AG, 2022-10-01T00:00:00Z.
• Subjects: article
• Online Access: Connect to this object online.

Summary

Here, we report the Cu(II)-photocatalysed hydrocarboxylation of imines (C=N) from a series of synthesized Schiff Base derivatives, namely <i>(E)-1-(4-((4-methylbenzylidene)amino)phenyl)ethanone</i>, (<i>E</i>)-1-(3-((5-bromo-2-hydroxybenzylidene)amino)phenyl)ethanone, (E)-4-((5-bromo-2-hydroxybenzylidene)amino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one, and (E)-1,5-dimethyl-4-((4-methylbenzylidene)amino)-2-phenyl-1H-pyrazol-3(2H)-one, with carbon dioxide (CO₂) to generate disubstituted amino acids. Under mild conditions (atmospheric pressure of CO₂, room temperature, and 30 W Blue LED light), good to excellent yields confirming the formation of substituted amino acid unsaturated acid derivatives were obtained. Single crystal X-ray diffraction (SC-XRD) and UV-Vis diffuse reflectance spectroscopy (UV-Vis-DRS) confirmed the square pyramidal geometry of the Cu(II) photocatalyst. Docking and DFT calculations of the substituted amino acid unsaturated acid derivatives showed their potential as antimicrobial molecules.

Item Description

10.3390/ph15101240
1424-8247