Dreier AL, Beutel B, Mück-Lichtenfeld C, Matsnev AV, Thrasher JS, Haufe G.
J Org Chem. 2016 Dec 30. doi: 10.1021/acs.joc.6b02805. [Epub ahead of print]Earlier studies have shown that [3,3]-sigmatropic rearrangements of allyl esters are useful for the construction of fluorine-containing carboxylic acid derivatives. This paper describes the synthesis of 3-aryl-pent-4-enoic acid derivatives bearing either a pentafluorosulfanyl (SF5) or a trifluoromethyl (CF3) substituent in the 2-position by treatment of corresponding SF5 or CF3 acetates of p-substituted cinnamyl alcohols with trimethylamine followed by trimethylsilyl triflate (TMSOTf). Read More