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269.Org. Lett. 2024, 26, 17, 3661–3666

date:2024-05-10

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


Jie Liu, Hao-Wen Jiang, Xiu-Qin Hu,* and Peng-Fei Xu*


https://doi.org/10.1021/acs.orglett.4c01186







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 Nalkoxylpyridinium salts as bifunctional reagents with an exceptionally low catalyst loading (0.5 mol %).