An organophotoredox-catalyzed decarboxylative cross-coupling between azole nucleophiles and aliphatic carboxylic acid-derived redox-active esters is demonstrated. This protocol efficiently installs various tertiary or secondary alkyl fragments onto the nitrogen atom of azole nucleophiles under mild and transition-metal-free conditions. The pyridinium additive successfully inhibits the formation of elimination byproducts from the carbocation intermediate. This reaction is applicable to the synthesis of a protein-degrader-like molecule containing an azole and a thalidomide.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.1c01745 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Photocatalyzed Azidofunctionalization of Alkenes via Radical-Polar Crossover.
Angew Chem Int Ed Engl
January 2025
Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, École Polytechnique Fédérale de Lausanne, CH-1015, Lausanne, Switzerland.
The azidofunctionalization of alkenes under mild conditions using commercially available starting materials and easily accessible reagents is reported based on a radical-polar crossover strategy. A broad range of alkenes, including vinyl arenes, enamides, enol ethers, vinyl sulfides, and dehydroamino esters, were regioselectively functionalized with an azide and nucleophiles such as azoles, carboxylic acids, alcohols, phosphoric acids, oximes, and phenols. The method led to a more efficient synthesis of 1,2-azidofunctionalized pharmaceutical intermediates when compared to previous approaches, resulting in both reduction of step count and increase in overall yield.
View Article and Find Full Text PDFApplication of a nucleophilic substitution rection for spectrofluorimetric quantification of ketamine in pharmaceutical and plasma matrices.
Sci Rep
December 2024
Pharmaceutical Analytical Chemistry Department, Faculty of Pharmacy, Al-Azhar University, Nasr City, 11751, Cairo, Egypt.
Ketamine is a dissociative anesthetic drug that is abused by teenagers and young adults, commonly for recreational purposes in dance clubs, to generate euphoria and dissociation, and sometimes employed as a date-rape drug. Herein, a highly sensitive, and environmentally friendly spectrofluorimetric method was developed for detection of ketamine in pharmaceutical and plasma samples. The technique is based on a nucleophilic substitution reaction occurring between ketamine and NBD-Cl (4-chloro-7-nitrobenzo-2-oxa-1,3-diazole), resulting in the formation of a fluorescent derivative that exhibits detectability at a remarkable level.
View Article and Find Full Text PDFThermally stable and polar zwitterionic liquid stationary phases for gas chromatography: Understanding the impact of chemical structure.
J Chromatogr A
January 2025
Restek Corporation, 110 Benner Circle, Bellefonte, PA, 16823, USA. Electronic address:
The chemical structure of nine imidazolium sulfonate and triflimide zwitterionic liquids (ZILs) were systematically tuned to increase their thermal stability for gas chromatography (GC) separations. Substituents for imidazolium and 2-phenylimidazolium cation systems, comprised of alkyl, benzyl, and oligoether groups of varying chain lengths, were studied as stationary phases in GC. Propanesulfonate, ethanesulfonate, and propanetriflimide anions were examined to understand the effect of linker length and nucleophilicity on ZIL thermal stability.
View Article and Find Full Text PDFMethoxyquinolone-Benzothiazole Hybrids as New Aggregation-Induced Emission Luminogens and Efficient Fluorescent Chemosensors for Cyanide Ions.
Int J Mol Sci
November 2024
Departamento de Química y Biología, División de Ciencias Básicas, Universidad del Norte, Km 5 vía Puerto Colombia, Barranquilla 081007, Colombia.
This work describes the synthesis and characterization of new quinolone-benzothiazole hybrids, the study of their aggregation-induced emission (AIE) properties, and the use of these systems as efficient fluorescent probes for cyanide ions. These conjugated derivatives are linked through a double bond favoring electronic communication, and together with their planar geometry, can strongly aggregate under solvophobic environments, leading to aggregation and exhibiting significant AIE behavior. The double bond between electroactive units is prone to nucleophilic addition reactions by cyanide ions, selectively, conducive to turning off the fluorescence properties, making this hybrid system an efficient probe for cyanide ions.
View Article and Find Full Text PDF1-Butyl-3-methylimidazolium-Based Ionic Liquid in Biomass Fractionation-Green Solvent or Active Reagent Toward Lignin Compounds?
Int J Mol Sci
November 2024
Core Facility Center 'Arktika', Northern (Arctic) Federal University, Arkhangelsk 163002, Russia.
N,N'-Dialkylimidazolium-based ionic liquids are capable of completely dissolving lignocellulosic biomass at elevated temperatures and are considered as promising green solvents for future biorefining technologies. However, the obtained ionic liquid lignin preparations may contain up to several percent nitrogen. This indicates strong interactions between the biopolymer and the IL cation, the nature of which has not yet been clarified.
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!