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Issue 10, 2018
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Selective remote C–H trifluoromethylation of aminoquinolines with CF3SO2Na under visible light irradiation in the absence of an external photocatalyst

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Abstract

A highly selective remote C–H trifluoromethylation of 8-aminoquinoline scaffolds in the C5-position with CF3SO2Na under visible light irradiation without an external photocatalyst has been developed. The protocol employs commercially available sodium trifluoromethanesulfinate (CF3SO2Na) as a trifluoromethylation reagent and shows a broad substrate scope, generating various 5-trifluoromethylated quinolines in good yields under photocatalyst-free, simple and mild conditions. Investigations indicated that both the starting material and product act as photosensitizers and 1O2 coexists with O2˙ during the reaction through energy transfer and single electron transfer processes. It is important to note that the electronic effect of the CF3 group as a substituent introduced into quinoline rings makes their trifluoromethylation more efficient under photo-irradiation from ultraviolet to visible light in the absence of an external photocatalyst.

Graphical abstract: Selective remote C–H trifluoromethylation of aminoquinolines with CF3SO2Na under visible light irradiation in the absence of an external photocatalyst

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Publication details

The article was received on 04 Mar 2018, accepted on 29 Mar 2018 and first published on 30 Mar 2018


Article type: Research Article
DOI: 10.1039/C8QO00229K
Citation: Org. Chem. Front., 2018,5, 1689-1697
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    Selective remote C–H trifluoromethylation of aminoquinolines with CF3SO2Na under visible light irradiation in the absence of an external photocatalyst

    L. Zhao, P. Li, X. Xie and L. Wang, Org. Chem. Front., 2018, 5, 1689
    DOI: 10.1039/C8QO00229K

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