TsCl-promoted thiolation of quinoline N-oxides with thiophenols.

Chengxian Hu, Ruikai Liu, Zhitao Ning, Dan Mou, Ying Fu, Zhengyin Du

Organic & biomolecular chemistry 2022 Nov 02

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A metal-free method for the regioselective synthesis of 2-thiolated quinolines from quinoline N-oxides in water at room temperature is developed. The reaction is conducted using benzenethiols as thiolation reagents in the presence of p-toluenesulfonyl chloride via p-toluenesulfonyl chloride-assisted tandem C-H bond activation, nucleophilic addition, deoxygenation and aromatization processes. This method does not require the use of metal catalysts and oxidants. It shows the advantages of wide functional group tolerance, short reaction times and simple operation.

Citation

Chengxian Hu, Ruikai Liu, Zhitao Ning, Dan Mou, Ying Fu, Zhengyin Du. TsCl-promoted thiolation of quinoline N-oxides with thiophenols. Organic & biomolecular chemistry. 2022 Nov 02;20(42):8280-8284