98%
921
2 minutes
20
The aminomethylation reaction, a fundamental and versatile organic transformation is extensively utilized to incorporate an aminomethyl group into target molecules and plays a significant role in the synthesis of natural products and functional molecules. In recent years, N-Aryl glycines and their analogues have been widely explored in visible-light-promoted photoredox reactions to install an aminomethyl moiety or construct various N-heterocycles under mild conditions. Their key reaction intermediates are α-aminoalkyl radicals, imines, or iminium ions. Recent advances in this field have been summarized into five categories according to the proposed reaction mechanisms: (i) radical addition initiated aminomethylation reactions, (ii) radical-radical cross coupling reactions, (iii) radical-triggered annulation reactions, (iv) transformations involving imines, and (v) metallophotoredox dual catalysis. We hope this review will give an overview of visible-light-promoted photoredox reactions of N-aryl glycines and their analogues and drive further research progress in this area.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1002/asia.202500153 | DOI Listing |
Chem Asian J
August 2025
Department of Undergraduate Education-School of Food and Drug, Shenzhen Polytechnic University, Shenzhen, 518055, China.
The aminomethylation reaction, a fundamental and versatile organic transformation is extensively utilized to incorporate an aminomethyl group into target molecules and plays a significant role in the synthesis of natural products and functional molecules. In recent years, N-Aryl glycines and their analogues have been widely explored in visible-light-promoted photoredox reactions to install an aminomethyl moiety or construct various N-heterocycles under mild conditions. Their key reaction intermediates are α-aminoalkyl radicals, imines, or iminium ions.
View Article and Find Full Text PDFRSC Adv
June 2025
School of Biotechnology, Amrita Vishwa Vidyapeetham, Amritapuri Campus Clappana Kollam Kerala 690525 India
A mild and efficient one-pot procedure was developed for the synthesis of substituted aryl glycines from 2-chloro-aryl acetamides by intermolecular cyclization in the presence of CuCl·2HO and KOH under reflux condition in acetonitrile medium. The reaction mechanism substantiates the formation of the intermediate 1,4-diarylpiperazine-2,5-dione, which on cleaving with ethanolic KOH afforded the desired products in high yields and in short durations. Both electron-donating and electron-withdrawing substituents on the aromatic rings were well tolerated.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
June 2025
Department of Chemistry, University of Liverpool, Crown Street, Liverpool, L69 7ZD, UK.
A cationic Ir(I)-complex modified with the chiral diphosphine DM-SEGPHOS mediates the hydroalkylation of diverse α-methyl styrenes with N-aryl glycine derivatives. The processes occur with complete branched selectivity and high enantioselectivity. Styrenes possessing higher α-alkyl substituents also participate to provide the targets with moderate to excellent levels of diastereoselectivity.
View Article and Find Full Text PDFOrg Biomol Chem
May 2025
Department of Polymers & Functional Materials, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500 007, India.
We present an effective, visible light-driven method for the synthesis of -(β-amino)pyrazolidin-3-ones from -aryl glycine and azomethine imines. This additive-free protocol utilizes blue light ( = 435-445 nm) at room temperature, enabling a radical-mediated cascade reaction that delivers a diverse range of pyrazolidinones in yields up to 99%. The mild conditions, high efficiency, and broad substrate scope of this process make it an attractive strategy for streamlined synthesis in drug discovery and material science.
View Article and Find Full Text PDFOrg Biomol Chem
March 2025
Department of Chemistry, Capital Normal University, Beijing 100048, P. R. China.
A novel catalytic system has been developed, comprising 3,6-dichloro-1,2,4,5-tetrazine as the catalyst, zinc acetate as an additive, dichloromethane as the solvent, and air as the oxidizing agent. Under ambient conditions, this system effectively activates C-S bonds. Specifically, it facilitates the reaction between α-benzylthioglycine ester and electron-rich aromatics, achieving functionalization of the C-S bond.
View Article and Find Full Text PDF