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Visible-Light-Mediated Three-Component Alkene 1,2-Alkylpyridylation Reaction Using Alkylboronic Acids as Radical Precursors for the Synthesis of 4-Alkylpyridines

Zi-Jun Lei, Yi-Jian Ma, Qian-Qian Fan, Zhihua Wu, Yi-Yang Zheng, Guoming Sun, Zi-Wei Xi, Chengshuo Shen, Yong‐Miao Shen

2025The Journal of Organic Chemistry11 citationsDOI

Abstract

We report the photocatalyzed three-component alkene 1,2-alkylpyridylation reaction between alkylboronic acids, 4-cyanopyridine, and an olefin to achieve the pyridination and alkylation of the olefin and the synthesis of structurally diversified 4-alkylpyridines. The readily available and easily manipulated alkylboronic acids were used as alkyl radical precursors. The reactions take place under mild conditions with a broad substrate scope and are easy to scale up to gram level, and they are therefore of potential practical value for the synthesis and structural modification of biologically active alkylpyridine derivatives.

Topics & Concepts

AlkeneComponent (thermodynamics)ChemistryVisible spectrumOrganic chemistryCombinatorial chemistryPhotochemistryCatalysisMaterials scienceThermodynamicsOptoelectronicsPhysicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
Visible-Light-Mediated Three-Component Alkene 1,2-Alkylpyridylation Reaction Using Alkylboronic Acids as Radical Precursors for the Synthesis of 4-Alkylpyridines | Litcius