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

Lulu Zhao, Pinhua Li, Xiaoyu Xie, Lei Wang

Index: 10.1039/C8QO00229K

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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.