[SnIV(TPP)(BF4)2]: An efficient and reusable catalyst for chemoselective trimethylsilylation of alcohols and phenols with hexamethyldisilazane

Tin(IV)tetraphenylporphyrinato tetrafluoroborate, [SnIV(TPP)(BF4)2], was used as an efficient catalyst for trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS). High-valent [SnIV(TPP)(BF4)2] catalyzes trimethylsilylation of primary, secondary and tertiary alcohols as well as phenols, and the corresponding TMS-ethers were obtained in high yields and short reaction times at room temperature. While, under the same reaction conditions [SnIV(TPP)Cl2] is less efficient to catalyze these reactions. One important feature of this catalyst is its ability in the 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 abstractHigh-valent [SnIV(TPP)(BF4)2] was used as an efficient and reusable catalyst for trimethylsilylation of primary, secondary and tertiary alcohols as well as phenols, and the corresponding TMS-ethers were obtained in high yields. The chemoselective silylation of primary alcohols in the presence of secondary and tertiary alcohols and phenols was also investigated.Figure optionsDownload full-size imageDownload as PowerPoint slide