Photoinduced synthesis of α-trifluoromethylated ketones through the oxidative trifluoromethylation of styrenes using CF3SO2Na as a trifluoromethyl reagent without an external photoredox catalyst?

Organic Chemistry Frontiers Pub Date: 2018-11-22 DOI: 10.1039/C8QO01079J

Abstract

A photoinduced strategy to access α-CF3-substituted ketones through the reaction of simple styrenes with sodium trifluoromethanesulfinate (CF3SO2Na) in the absence of an external photosensitizer under LED (380–385 nm) irradiation and an air atmosphere at room temperature was developed. This reaction employs the commercially available, low cost, and easy to handle Langlois reagent (CF3SO2Na) as a CF3-radical source, and the reaction has advantages of mild conditions, a simple system and good functional group tolerance. Investigations indicated that the product acts as a photosensitizer and 1O2 coexists with O2˙? during the reaction through the energy transfer and single electron transfer process.

Graphical abstract: Photoinduced synthesis of α-trifluoromethylated ketones through the oxidative trifluoromethylation of styrenes using CF3SO2Na as a trifluoromethyl reagent without an external photoredox catalyst
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