A novel route to access trifluoromethylketones (TFMKs) from Weinreb amides is presented. This methodology represents the first documented case of an amide reacting with the Ruppert-Prakash reagent (TMS-CF3) in a targeted synthesis of TFMKs, without any double-trifluoromethlyation. Various aryl and alkyl substrates have been shown to undergo this transformation in moderate to excellent yields. The proposed mechanistic route is evidenced by an isolatable intermediate. As well as an overview of the synthetic methodology, a discussion of the unusual reactivity of these amides, and the selectivity towards monotrifluoromethlyation of the reaction will be presented.

Synthesis of trifluoromethylketones via a Weinreb amide approach

244th National Meeting (2012)

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