Synthesis of ortho-perfluoroalkyl phenones from hemifluorinated enones as key building blocks

The title compounds are prepared by cycloaddition of perfluoroalkenyl ketones and 1,3-dienes, with a subsequent aromatization by basic dehydrofluorination. The perfluoroalkenyl ketones were prepared by the reaction of perfluoroorganometallic reagents with acylsilanes. The transformation may be performed more efficiently in a simplified process without purification of the intermediate cycloadducts. The overall methodology is an interesting entry to ortho-perfluoroalkyl phenones with the possibility to vary the substitution at the acyl and on the ring moiety. (c) 2006 Elsevier Ltd. All rights reserved.