Light-induced dehydrogenative cascade trifluoromethylation with water

What is it about?

Unprecedented light-induced oxidant and metal-free tandem radical cyclization–trifluoromethylation and dehydrogenative oxygenation of 1,6-enynes have been achieved using a photoredox catalyst, CF3SO2Na, and phenanthrene-9,10-dione (PQ), Langlois’ reagent (CF3SO2Na) and water as the oxygen source. The mechanistic investigations by UV-visible and ESR spectroscopy, electrochemical studies, isotope labelling and density functional theory (DFT) suggest that light induced PQ produced a CF3 radical from CF3SO2Na.

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Why is it important?

The generated CF3 radical adds to the alkene, followed by cyclization, to provide a vinylic radical that transfers an electron to PQ and induced a vinylic cation. Alternatively, electron transfer may occur from the CF3-added alkene moiety, forming a carbocation, which would undergo cationic cyclization to generate a vinylic carbocation. The subsequent addition of water to the vinylic cation, followed by the elimination of hydrogen gas, led to the formation of trifluoromethylated C3-aryloyl/acylated heterocycles.