Highly efficient and chemoselective trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) catalyzed by reusable electron-deficient [TiIV(salophen)(OTf)2]

In the present work, highly efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) catalyzed by high-valent [TiIV(salophen)(OTf)2] is reported. Under these conditions, primary, secondary and tertiary alcohols as well as phenols were silylated in short reaction times and high yields. It is noteworthy that this method can be used for chemoselective silylation of primary alcohols in the presence of secondary and tertiary alcohols and phenols. The catalyst was reused several times without loss of its catalytic activity.

Graphical abstractHighly efficient trimethylsilylation of primary, secondary and tertiary alcohols as well as phenols with hexamethyldisilazane catalyzed by high-valent [TiIV(salophen)(OTf)2] is reported. It is noteworthy that this method can be used for chemoselective silylation of primary alcohols in the presence of secondary and tertiary alcohols and phenols. The catalyst was reused several times without loss of its catalytic activity.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Electron-deficient Ti(IV)salophen was used as catalyst. ► The corresponding trimethylsilyl ethers were obtained by the reaction of alcohols and phenols with HMDS. ► The reaction was carried out at room temperature. ► The catalyst was reusable.