HOF·CH 3CN complex

Abstract

Rozen and coworkers reported the first direct oxidation of aliphatic and aromatic azides into nitro compounds with HOF·CH 3CN complex in excellent yields. (Diagram presented). As a strong oxidant, HOF¡CH 3CN complex can oxidize aromatic amines to nitroarenes in high yields. It can also oxidize the amino group of α-amino esters to α-nitro esters without affecting the aromatic ring. (Diagram presented). HOF·CH 3CN complex is an ecologically friendly oxidizing agent and can oxidize alcohols and methyl ethers to ketones. Ketones also undergo Baeyer-Villiger oxidation to give esters under the same reaction conditions. All these reactions are ionic in nature. (Diagram presented). With its strong electrophilic oxygen, HOF·CH 3CN complex is an excellent oxygen transfer agent that epoxidizes a wide variety of alkenes and alkynes, including very deactivated ones that cannot be directly epoxidized by other methods. (Diagram presented). HOF·CH 3CN complex can oxidize all types of sulfides to sulfones in excellent yields in only a few minutes at or below room temperature. The reaction proceeds through the formation of sulfoxides which, at low temperatures of around -78 °C, can be isolated in good yields. (Diagram presented). HOF·CH 3CN complex can also hydroxylate and otherwise oxidize many aromatic compounds, though yields are moderate. (Diagram presented). © Georg Thieme Verlag Stuttgart.