Mixed Organofluorine-Organosilicon Chemistry. 3. A Highly Efficient and Convenient Synthesis of Aryl Perfluoroalk-1-enyl Ketones from Perfluoroalkyl Iodides and Aroylsilanes

Article abstract of DOI:10.1021/jo00076a028

A one-pot procedure is described to synthesize aryl perfluoroalkenyl ketones with high yields from perfluoroalkyl iodides and aroylsilanes.It consists of conversion of the iodide to the perfluoroorganomagnesium bromide followed by reaction with the aroylsilane, in ether, at low temperatures (-45 deg C).Warming to room temperature and addition of triethylamine accelerate the process leading quantitatively to the enones, which can be isolated in the pure E-configuration.The mechanism of this synthesis, involving a Brook rearrangement, is discussed.An alternative procedure is proposed to synthesize the same enones, with equivalent efficiency, from 1-aryl-1-(trimethylsilyl)perfluoroalkan-1-ols.