The development of methods for the introduction of trifluoromethyl groups onto aromatic rings or alkenyl groups has been of great interest due to the unique physical and biological activities of compounds containing trifluoromethyl group.Recently, visible light photoredox catalysis has attracted substantial attention due to its environmental compatibility and versatility in promoting a large number of synthetically important reactions. This eco-friendly chemistry has also been applied to trifluoromethylations. A variety of electron-rich heterocycles and alkenes were transformed into trifluoromethylated products by using CF3I as the trifluoromethyl radical source and ruthenium photocatalysts under mild reaction conditions. In addition, efficient methods for the generation of CF3-containing epoxides and aziridines, which are potential trifluoromethylated building blocks, have been developed.Controlling a reaction that can form multiple products is highly attractive and challenging in synthetic chemistry. We obtained three different valuable alkenyl� and alkynyl�CF3 compounds from the same starting materials, an alkyne and CF3I, by the judicious choice of reaction conditions using different photoredox catalysts, bases, and solvents.  

Trifluoromethylation by visible light photoredox catalysis

248th National Meeting (2014)

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