High-valent titanium(IV)salophen: An efficient catalyst for rapid conversion of aldehydes to 1,1-diacetates with acetic anhydride

In the present work, a mild and highly efficient method for protection of aldehydes with acetic anhydride in the presence of high-valent titanium (IV) salophen trifluoromethanesulfonate, [TiIV(salophen)(OTf)2], at room temperature is reported. Under these conditions, different aldehydes bearing electron-withdrawing and electron-donating substituents were reacted with acetic anhydride and the corresponding 1,1-diacetates were obtained in good to excellent yields. The results showed that the yields were higher for aldehydes bearing electron-withdrawing substituents such as nitro, chloro, bromo and 3-methoxy, while aldehydes containing electron donating groups such as 4-methoxy and 4-methyl produced the lower yields. The catalyst was reused several times without loss of its catalytic activity.

A mild and highly efficient method for protection of aldehydes with acetic anhydride in the presence of high-valent [TiIV(salophen)(OTf)2] is reported. Under these conditions, different aldehydes bearing electron-withdrawing and electron-donating substituents were reacted with acetic anhydride and the corresponding 1,1-diacetates were obtained in good to excellent yield. The catalyst was reused several times without loss of its catalytic activity.Figure optionsDownload as PowerPoint slideHighlights
► Electron-deficient Ti(IV)salophene was used as catalyst.
► 1,1-Diacetates were obtained by the reaction of aldehydes with acetic anhydride.
► The reaction was carried out at room temperature.
► The catalyst was reusable.