We have developed a copper-mediated direct �-trifluoromethylation of a- and �-substituted N,N-diethylacrylamides. The amide moiety acts as a directing group for the regio- and the stereo-controlled construction of Csp2-CF3 bond. The reaction is carried out under acidic conditions in the presence of Umemoto's reagent. This method does not require prefunctionalized substrates and delivers excellent stereoselectivity toward the otherwise difficult to access Z diastereoisomers. This method was not limited to terminal alkenes but was also applied to sterically more hindered, substituted alkenes, offering a straightforward approach for the synthesis of valuable fluorinated building blocks.

Contribution to the study of trifluoromethylation and trifluoromethylthiolation reactions

248th National Meeting (2014)

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