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

โœ Scribed by Majid Moghadam; Shahram Tangestaninejad; Valiollah Mirkhani; Iraj Mohammadpoor-Baltork; Shadab Gharaati

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
162 KB
Volume
23
Category
Article
ISSN
0268-2605

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โœฆ Synopsis

Abstract

In this paper, rapid and highly efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) in the presence of catalytic amounts of highโ€valent [Sn^IV^(TPP)(OTf)~2~] is reported. This catalytic system catalyzes trimethylsilylation of primary, secondary and tertiary alcohols as well as phenols, and the corresponding TMSโ€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 times without loss of its catalytic activity. Copyright ยฉ 2009 John Wiley & Sons, Ltd.

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