A novel electrochemical synthesis protocol has been achieved for reductive amination between aldehydes and amines in undivided cells at room temperature. Under metal-free and external-reductant-free electrolysis conditions, various important secondary amine products are obtained in moderate-to-high yields. Deuterium-labeling experiments have demonstrated that low-toxicity DMSO acts both as a solvent and a H-donor in the reaction. On this basis, various deuterium-labeled products with good-to-excellent D-incorporation have been synthesized by using DMSO-d6 as a solvent. Furthermore, a molecule with GR-antagonistic activity has been synthesized through further sulfonylation.

Download full-text PDF

Source
http://dx.doi.org/10.1039/d0ob01163kDOI Listing

Publication Analysis

Top Keywords

reductive amination
8
amination aldehydes
8
aldehydes amines
8
direct electrochemical
4
electrochemical reductive
4
amines h/d-donor
4
h/d-donor solvent
4
solvent novel
4
novel electrochemical
4
electrochemical synthesis
4

Similar Publications

Photocatalytic Three-Component Reductive Coupling Synthesis of -Difluorohomoallyl Secondary Amines.

J Org Chem

January 2025

Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Sciences, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, P. R. China.

-Difluorohomoallyl amines, an important class of -difluoroalkenes, are prevalent moieties in many bioactive compounds. However, limited methods are suitable for the synthesis of this type of compound containing secondary amines. Here, we display a photocatalytic multicomponent protocol for the synthesis of -difluoroalkenes containing secondary amines, which makes use of readily available materials: arylamines, alkyl aldehydes, and α-trifluoromethyl alkenes.

View Article and Find Full Text PDF

Secondary amines are vital functional groups in pharmaceuticals, agrochemicals, and natural products, necessitating efficient synthetic methods. Traditional approaches, including N-monoalkylation and reductive amination, suffer from limitations such as poor chemoselectivity and complexity. Herein, we present a streamlined deoxygenative photochemical alkylation of secondary amides, enabling the efficient synthesis of α-branched secondary amines.

View Article and Find Full Text PDF

We report the development and optimization of a scalable flow process for metallaphotoredox (Ir/Ni) C-O coupling, a mild and efficient approach for forming alkyl-aryl ethers, a common motif in medicinal and process chemistry settings. Time-resolved infrared spectroscopy (TRIR) highlighted the amine as the major quencher of the photocatalyst triplet excited state, along with the formation of an Ir(II) species that, in the presence of the Ni cocatalyst, has its lifetime shortened, suggesting reductive quenching of Ir(III)*, followed by reoxidation facilitated by the Ni cocatalyst. TRIR and batch reaction screening was used to develop conditions transferrable to flow, and many processing benefits of performing the reaction in flow were then demonstrated using a simple to construct/operate, small-footprint FEP coil flow reactor, including short (<10 min) space times and reduced catalyst loadings (down to 0.

View Article and Find Full Text PDF

This work reports the step-wise fabrication of a core-shell plasmonic nanocomposite Pd@BTL-Cd consisting of a BTL-Cd shell and a palladium nanoparticle core. BTL-Cd is the [Cd(BTL)·CdCl] complex where the heptadentate framework of the bis-compartmental ligand encapsulated two Cd(II) centres in separate pockets. Pd@BTL-Cd has been found to be highly efficient for the photocatalytic conversion of furfural (a biomass-derived aldehyde) to furfuryl amine reductive amination in aqueous ammonia at room temperature.

View Article and Find Full Text PDF

Acridine/Lewis Acid Complexes as Powerful Photocatalysts: A Combined Experimental and Mechanistic Study.

ACS Catal

October 2024

Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.

A class of generated Lewis acid (LA) activated acridine complexes is reported, which act as potent photochemical catalysts for the oxidation of a variety of protected secondary amines. Acridine/LA complexes exhibit tunable excited state reduction potentials ranging from +2.07 to 2.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!