Oxidation of α-CF3 and Other Secondary Alcohols to Ketones Using a Nitroxide Catalyst
Oxidation of α-Trifluoromethyl and Nonfluorinated Secondary Alcohols to Ketones Using a Nitroxide Catalyst: F. Politano, W. P. Brydon, N. E. Leadbeater
Synthesis 2023, DOI: 10.1055/s-0042-1752398
α-Trifluoromethyl ketones are valuable building blocks for the synthesis of more complex and functionalized fluorinated compounds, as well as important compounds in medicinal and biological chemistry, for example displaying remarkable properties as enzyme inhibitors.
A direct access route to α-trifluoromethyl ketones would be the oxidation of the corresponding secondary alcohols, but classical methods for alcohol oxidation are typically inefficient, because the inductive effect of the strongly electron-withdrawing CF3 group raises the activation barrier for oxidation. Recently, the group of Professor Nicholas E. Leadbeater from the University of Connecticut (Storrs, USA) reported a novel oxidative strategy for achieving the target transformation.
Professor Leadbeater said: “Using a clean, green oxidation approach, we have developed a method for making trifluoromethyl ketones, a class of compounds that can be really challenging to make yet very interesting in its own right and serving as starting material for other classes of fluorine-containing molecules. The method can also be applied to non-fluorinated alcohols, thereby increasing its utility even more.”