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Visible-Light-Promoted C2 Selective Arylation of Quinoline and Pyridine <i>N</i>-Oxides with Diaryliodonium Tetrafluoroborate

Dazhi Li, Ce Liang, Zaixing Jiang, Junzheng Zhang, Wang-Tao Zhuo, Fan-Yue Zou, Wanpeng Wang, Guo‐Lin Gao, Jinzhu Song

2020The Journal of Organic Chemistry47 citationsDOI

Abstract

A protocol of visible-light-promoted C2 selective arylation of quinoline and pyridine N-oxides, with diaryliodonium tetrafluoroborate as an arylation reagent, using eosin Y as a photocatalyst for the construction of N-heterobiaryls was presented. This methodology provided an efficient way for the synthesis of 2-aryl-substituted quinoline and pyridine N-oxides. This strategy has the following advantages: specific regioselectivity, simple operation, good functional group tolerance, and high to moderate yields under mild conditions.

Topics & Concepts

QuinolineTetrafluoroborateReagentPyridineChemistryRegioselectivityArylCombinatorial chemistryFunctional groupCatalysisOrganic chemistryAlkylIonic liquidPolymerRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
Visible-Light-Promoted C2 Selective Arylation of Quinoline and Pyridine <i>N</i>-Oxides with Diaryliodonium Tetrafluoroborate | Litcius