Visible-light-induced three-component 1,2-alkylpyridylation of alkenes with unactivated alkyl iodides and aryl cyanides is reported via a photocatalytic halogen-atom transfer (XAT) strategy. This metal-free protocol utilizes readily available tertiary alkylamine as the terminal reductant to smoothly convert alkyl iodides into the corresponding carbon radical species. The reaction features a broad substrate scope, excellent functional group tolerance, high efficiency, and mild reaction conditions. The practicability of this methodology is further demonstrated in the late-stage difunctionalization of bioactive molecules.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.3c02388 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Metal-organic frameworks (MOFs) of an MIL-101-supported iridium(III) complex as efficient photocatalysts in the three-component alkoxycyanomethylation of alkenes.
Dalton Trans
January 2025
College of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, PR China.
Metal-organic frameworks (MOFs) exhibit intriguing physicochemical properties due to their manageable structure, abundant porosity, and uniform pore size, which provide ideal environments for photocatalysts to achieve highly efficient photocatalysis. In this work, -Ir(ppy) is directly anchored to MOFs of MIL-101 with different morphologies Friedel-Crafts alkylation, affording various MIL-101-supported -Ir(ppy) without the molecular modification of -Ir(ppy). The as-fabricated photocatalysts possess high specific surface areas (785-962 m g), pore volumes (0.
View Article and Find Full Text PDFVisible-light-induced cascade chromone cyclization/chalcogenation to access 3-chalcogenyl-chromones using elemental sulfur/selenium.
Chem Commun (Camb)
December 2024
School of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou, Henan 450001, P. R. China.
A mild and efficient visible-light-induced cascade undergoing a chromone cyclization/chalcogenation at room temperature has been developed. This three-component reaction employs user-friendly elemental S and Se as the chalcogenide source, providing an attractive route for the convenient synthesis of 3-chalcogenyl-chromones with a wide substrate scope and good functional group tolerance.
View Article and Find Full Text PDFStabilized Carbon Radical-Mediated Assembly of Arylthianthrenium Salts, Alkenes and Amino Acid/Peptide Derivatives.
Adv Sci (Weinh)
January 2025
National and Local Joint Engineering Research Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing, 210023, P. R. China.
Efficiently assembling amino acids and peptides with bioactive molecules facilitates the modular and streamlined synthesis of a diverse library of peptide-related compounds. Particularly notable is their application in pharmaceutical development, leveraging site-selective late-stage functionalization. Here, a visible light-induced three-component reaction involving arylthianthrenium salts, amino acid/peptide derivatives, and alkenes are introduced.
View Article and Find Full Text PDFVisible Light-Induced Three-Component Alkoxyalkylation of Alkenes with α-Halocarbonyls and Alcohols.
J Org Chem
December 2024
Center for Metareceptome Research, Graduate School of Pharmaceutical Sciences, Chung-Ang University, 84 Heukseok-ro, Dongjak, Seoul 06974, Republic of Korea.
A visible-light-induced three-component alkoxyalkylation of alkenes has been developed under the photocatalysis of -Ir(ppy). The alkene substrate scope included aryl and aliphatic alkenes as well as electron-rich and electron-deficient alkenes, allowing the facile coupling with a diverse array of α-halocarbonyl compounds. The redox potential-guided orchestration of radical processes with precision allows rapid access to highly functionalized products that are useful building blocks in organic synthesis.
View Article and Find Full Text PDFThree-Component Photochemical Cyclization/Dithiocarbamate Formation of -Difluoro Quinolin-2(1)-ones.
Org Lett
November 2024
College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang, 455000, P. R. China.
Herein, a novel visible-light-induced 6- difluoromethylation cyclization and subsequent carbo-thioesterification reaction is described. This protocol allows efficient access to valuable -difluoro quinolin-2(1)-ones in moderate to excellent yields under mild conditions. Broad amino sources compatibility, including cyclic morpholine, thiazolidine, thiomorpholine, pyrrolidine, 1,4-oxazepane, 2,6-dimethylmorpholine, -butyl piperazine-1-carboxylate and noncyclic diethylamine, -ethylpropan-1-amine, -benzylethanamine, -benzyl-trimethylsilanamine, dibenzylamine, and -(4-methoxybenzyl)ethanamine, demonstrated the practicability of this strategy.
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!