The cross-aldol reaction of hexafluoroacetone (HFA) with ketones catalyzed by an acid

The cross-aldol reactions of hexafluoroacetone (HFA) and ketones using an acid catalyst are reported. When concentrated sulfuric acid was employed as the catalyst, HFA reacted regioselectively with various ketones at 50–100 °C to give the aldol adducts (6) in good yields. The reaction is initiated by an acid-catalyzed transformation of the ketone into the corresponding enol that reacts with HFA. The obtained adducts (6) can be reduced with hydrogen under a Ru/C catalyst to lead to the corresponding fluorine-containing diols (13).

Graphical abstractThe cross-aldol reaction of hexafluoroacetone (HFA) and ketones using an acid catalyst occurred efficiently.Figure optionsDownload full-size imageDownload as PowerPoint slide