In recent years, a great deal of effort has been devoted to the development of synthetic methods for the introduction of the CF3 moiety into organic molecules. Of particular interest is the C(sp2)–CF3 bond formation. Available methods usually start from C(sp2)–X (X= halide, pseudohalide). However, the corresponding transformation using C(sp2)–H has been much less developed and most available protocols rely on pre-formed electrophilic CF3-transfer reagents. In this presentation, a convenient method for the C–H trifluoromethylation of enamides is disclosed. Under oxidative conditions, a series of versatile beta-CF3 enamides can be accessed using TMSCF3 as a convenient, inexpensive and readily available CF3 source, thus avoiding the use of expensive electrophilic trifluoromethylating reagents. Results of our investigations on the further functionalization of the obtained products will also be discussed.

Oxidative C(sp2)–H trifluoromethylation of enamides using TMSCF3

254th National Meeting (2017)

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