AI Article Synopsis
Article Abstract
Reported herein is a convenient and efficient method for one-pot, catalytic reductive amination, as well as the first multi-component tandem reductive amination-functionalization of bench-stable and readily available common carboxylic esters. This method is based on the cationic [Ir(COD)]BArF-catalyzed chemoselective hydrosilylation of esters, followed by one-pot acid-mediated amination and nucleophilic addition. The reaction was conducted under mild conditions at a very low catalyst loading (0.1 mol % of Ir), which could be further reduced to 0.001 mol %, as demonstrated by a reaction at a 15 g scale. The method is highly versatile, allowing the use of esters with or without α-protons for the N-mono-alkylation of primary and secondary amines to produce diverse secondary and tertiary amines, as well as α-branched/functionalized amines. The method is highly chemoselective and tolerates a variety of functional groups such as bromo, trifluoromethyl, ester, and cyano groups. The value of the method was demonstrated by the one-step catalytic synthesis of two bio-relevant N-mono-methyl α-amino esters and the antiparkinsonian agent piribedil, as well as by the use of two shorter chain triglycerides as alkylating feedstock.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/anie.202422742 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Iron-Assisted and Cu-Mediated Direct Aminocarbonylation of Nitroarene with Boronic Acid.
J Org Chem
December 2024
Department of Chemistry, Malaviya National Institute of Technology Jaipur, JLN Marg, Jaipur 302017, Rajasthan, India.
Herein, we have established the formation of diaryl amide by aminocarbonylation of nitrobenzene with boronic acids. The method works in the catalytic presence of economical and commercially available CuI salt, which was significantly promoted by the FeSe(CO) cluster. Mo(CO) serves as a source of CO, and it also acts as a reductant with a combination of iron cluster.
View Article and Find Full Text PDFPhotoredox/Cobalt-Catalyzed Chemo-, Regio-, Diastereo- and Enantioselective Reductive Coupling of 1,1-Disubstituted Allenes and Cyclobutenes.
Angew Chem Int Ed Engl
December 2024
Shanghai Institute of Organic Chemistry, State Key Lab of Organometallic Chemistry, 345 Lingling Road, 200032, Shanghai, CHINA.
A dual photoredox/cobalt-catalyzed protocol for chemo-, regio-, diastereo- and enantioselective reductive coupling of 1,1-disubstituted allenes and cyclobutenes through chemo-, regio-, diastereo- and enantioselective oxidative cyclization followed by stereoselective protonation promoted by a chiral phosphine-cobalt complex is presented. Such process represents an unprecedented reaction pathway for cobalt catalysis that enables selective transformation of the less sterically congested alkenes of 1,1-disubstituted allenes with cyclobutenes, incorporating a broad scope of tetrasubstituted alkenes into the cyclobutane scaffolds in up to 86% yield, >98:2 chemo- and regioselectivity, >98:2 dr and >99.5:0.
View Article and Find Full Text PDFDivalent Intermediates in Lanthanide-Based Photocatalysts: Spectroscopic Characterization and Reactivity.
Inorg Chem
December 2024
Department of Chemistry, Ångström Laboratory, Uppsala University, 75120 Uppsala, Sweden.
The reduction of stable trivalent lanthanide species (Ln(III)) by the excited states of organic chromophores is the basis of photocatalytic divalent lanthanide-mediated reduction reactions. While indirect evidence of the photochemical formation of the reactive Ln(II) species is abundant, direct spectroscopic evidence of their presence is scarce. Here, nine chromophores with absorptions covering the near UV and visible ranges were systematically investigated in the presence of Ln(III) ions to evaluate their ability to reduce Eu(III) upon excitation with visible light to the catalytically active Eu(II) species.
View Article and Find Full Text PDFDual Activities of Flower-like Gold-Iron Oxide Nanozyme for Peroxidase-mimicking and Glucose Detection.
Chem Asian J
December 2024
Indian Institute of Technology Roorkee, Department of Chemistry, Indian Institute of Technology Roorkee, 247667, Roorkee, INDIA.
Nanozymes, constituting of inorganic nanomaterials, are the sustainable and cost-effective alternatives of the naturally abundant enzymes. For more than a decade, nanozymes have shown astonishingly enhanced enzymatic activity as compared to its naturally occurring counterpart and emerged as a potential platform in biomedical science. The current study reports a novel flower shaped gold-iron oxide nanocomposite prepared via a facile and green solution phase redox mediated synthesis.
View Article and Find Full Text PDFReductive Zincke Reaction: Opening of Pyridinium Rings to δ-Amino Ketones via Transfer Hydrogenation.
Chemistry
December 2024
University of Liverpool, Department of Chemistry, Oxford Street, L69 7ZD, Liverpool, UNITED KINGDOM OF GREAT BRITAIN AND NORTHERN IRELAND.
The Zincke reaction and Birch reduction have been one of the few reactions that allow for ring opening of pyridines ever since the discovery of pyridine more than a century ago. This paper presents a new addition to the list of pyridine ring-opening reactions, reductive Zincke reaction, which affords saturated δ-amino ketones. Under the catalysis of a simple rhodium complex, pyridinium salts with diverse substituents are reduced with formic acid, ring-opened with water, transaminated with a secondary amine and further reduced to afford a wide range of δ-amino ketones, including those in which the alkane chain of the ketones is selectively deuterated or fluorinated.
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!