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Visible-Light-Induced Alkoxypyridylation of Alkenes Using N-Alkoxypyridinium Salts as Bifunctional Reagents

Jie Liu, Haowen Jiang, Xiu‐Qin Hu, Peng‐Fei Xu

2024Organic Letters19 citationsDOI

Abstract

Considering the ubiquitous presence of pyridine moieties in pharmaceutical compounds, it holds immense value to develop practical and straightforward methodologies for accessing heterocyclic aromatic hydrocarbons. In recent years, N-alkoxypyridinium salts have emerged as convenient radical precursors, enabling the generation of the corresponding alkoxy radicals and pyridine through single-electron transfer. Herein, we present the first report on visible-light-mediated intermolecular alkoxypyridylation of alkenes employing N-alkoxylpyridinium salts as bifunctional reagents with an exceptionally low catalyst loading (0.5 mol %).

Topics & Concepts

BifunctionalChemistryReagentPyridineIntermolecular forceRadicalAlkoxy groupCatalysisCombinatorial chemistryElectron transferPhotochemistryOrganic chemistryMoleculeAlkylRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
Visible-Light-Induced Alkoxypyridylation of Alkenes Using N-Alkoxypyridinium Salts as Bifunctional Reagents | Litcius