Rapid, highly efficient and chemoselective trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) catalyzed by reusable electron-deficient tin(IV)porphyrin

Abstract

In this paper, rapid and highly efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) in the presence of catalytic amounts of high-valent [SnIV(TPP)(OTf)2] is reported. This catalytic system 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. 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 timeswithout loss of its catalytic activity. © 2009 John Wiley & Sons, Ltd.