1,4-Additions of electron-rich heterocycles onto β-perfluoroalkyl enones

β-(Trifluoromethyl) enones, easily obtained in few steps from commercially available methyl hemiketal of trifluoroacetaldehyde, react with electron-rich O- and N-containing heterocycles (furans and benzofurans, pyrroles and indoles, hydroxycoumarins), through a 1,4 addition, to give heterocycles bearing a functionalized side-chain. β-(chlorodifluoromethyl)enones and β-(pentafluoroethyl)enones behave in the same way.

β-(Fluoroalkyl)enones react with O- and N-containing heterocycles to yield various heterocycles bearing a functionalized, fluorinated, side-chain.Figure optionsDownload as PowerPoint slideHighlights
► β-(Fluoroalkyl)enones.
► 1,4-Addition with heterocycles.
► Furans, benzofurans, indoles and coumarins give good yields.
► Various heterocycles bearing a functionalized, fluorinated, side-chain obtained.