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

Authors :
Chiang CW
Li HL
Lin TJ
Chen HC
Chou YH
Chou CJ
Source :
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2023 Oct 13; Vol. 29 (57), pp. e202301379. Date of Electronic Publication: 2023 Sep 12.
Publication Year :
2023

Abstract

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 NH <subscript>2</subscript> -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.<br /> (© 2023 Wiley-VCH GmbH.)

Details

Language :
English
ISSN :
1521-3765
Volume :
29
Issue :
57
Database :
MEDLINE
Journal :
Chemistry (Weinheim an der Bergstrasse, Germany)
Publication Type :
Academic Journal
Accession number :
37434348
Full Text :
https://doi.org/10.1002/chem.202301379