AI Article Synopsis
- A new method using visible light and a catalyst allows for the selective reduction of imines, which are compounds derived from aldehydes or ketones, employing EtN as a hydrogen source.
- This method can effectively reduce imines even when other sensitive groups, like nitriles or halides, are present in the molecule.
- The continuous-flow technique makes it easier to scale up the reaction for larger production, and various experiments confirmed how EtN functions in this process.
Article Abstract
A visible-light photocalytic method for the chemoselective transfer hydrogenation of imines in batch and continuous flow is described. The reaction utilizes EtN as both hydrogen source and single-electron donor, enabling the selective reduction of imines derived from diarylketimines containing other reducible functional groups including nitriles, halides, esters, and ketones. The dual role of EtN was confirmed by fluorescence quenching measurements, transient absorption spectroscopy, and deuterium-labeling studies. Continuous-flow processing facilitates straightforward scale-up of the reaction.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.7b03565 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Light-Dependent Chemoselective Amide or Thioamide Ligation of Acylsilanes with Amines using Elemental Sulfur.
Chemistry
January 2025
Xi'an Jiaotong University, School of Chemistry, No.28, West Xianning Road, 710049, Xi'an, CHINA.
Due to the diverse chemical and physical properties of functional groups, mild and controllable ligation methods are often required to construct complex drugs and functional materials. To make diverse sets of products with tunable physicochemical properties, it is also useful to employ complimentary ligation methods that adopt the same starting materials. Here, we disclose the efficient and modular synthesis of amides or thioamides through the chemical ligation of acyl silanes with amines, simply by turning a light on or off.
View Article and Find Full Text PDFCatalysis activity and chemoselectivity control with the ligand in Ru-H pincer complexes.
Dalton Trans
January 2025
Division of Chemical and Biological Sciences, Ames National Laboratory, Ames, IA 50011, USA.
(PhPNP)Ru(H)(Cl)(CO) serves as a precatalyst to a variety of important catalytic transformations but most improvements have been restricted to the replacement of the CO ligand to the hydride or changing the Ph groups of the pincer for other aryl or alkyl groups. The ligand to the hydride is often another hydride and studies that utilize other ligands in catalysis are limited. In this work, we synthesized a series of [(PhPNP)Ru(H)(CO)(L)][BPh] complexes bearing isonitrile, PMe, or a N-heterocyclic ligand to the Ru-H.
View Article and Find Full Text PDFCO2 Reduction at a Borane-Modified Iron Complex: A Secondary Coordination Sphere Strategy.
Angew Chem Int Ed Engl
January 2025
Western University, Chemistry, 1151 Richmond Street, N6A3K7, London, CANADA.
This work addresses fundamental questions that deepen our understanding of secondary coordination sphere effects on carbon dioxide (CO2) reduction using derivatized hydride analogues of the type, [Cp*Fe(diphosphine)H] (Cp* = C5Me5-) - a well-studied family of organometallic complex - as models. More precisely, we describe the general reactivity of [(Cp*-BR2)Fe(diphosphine)H], which contains an intramolecularly positioned Lewis acid, and its cooperative reactivity with CO2. Control experiments underscore the critical nature of borane incorporation for CO2 to reduced products, a reaction that does not occur for unfunctionalized [Cp*Fe(diphosphine)H]).
View Article and Find Full Text PDFAccessing Azetidines through Magnesium-Mediated Nitrogen Group Transfer from Iminoiodinane to Donor-Acceptor Cyclopropanes.
Angew Chem Int Ed Engl
January 2025
New York University, Chemistry, 29 Washington Place, RM 10001, 10003, New York, UNITED STATES OF AMERICA.
Herein, we report a Lewis acid-mediated ring expansion of donor-acceptor cyclopropanes (DACs) to substituted azetidines via nucleophilic nitrogen group transfer from readily accessible iminoiodinane. This protocol operates under mild, transition-metal-free conditions, and showcases excellent chemoselectivity, along with broad functional group tolerance. We report for the first time that challenging alkyl donor-acceptor cyclopropanes can undergo ring expansion leading to aliphatic azetidines without relying on external oxidants or precious transition-metal catalysts.
View Article and Find Full Text PDFIridium-Catalyzed Highly Selective 1,4-Reduction of α,β-Unsaturated Carbonyl Compounds.
Molecules
December 2024
Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China.
In this study, an iridium-catalyzed selective 1,4-reduction of α,β-unsaturated carbonyl compounds is realized, with water as a solvent and formic acid as a hydride donor. The new efficient iridium catalyst features a 2-(4,5-dihydroimidazol-2-yl)quinoline ligand. The chemoselectivity and catalyst efficiency are highly dependent on the electronic and steric properties of the substrates.
View Article and Find Full Text PDFWant 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!