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Tetrabutylammonium Phthalimide-N-oxyl: An Efficient Organocatalyst for Trimethylsilylation of Alcohols and Phenols with Hexamethyldisilazane

M.G. Dekamin*, N. Yazdaninia, J. Mokhtari and M.R. Naimi-Jamal

Pharmaceutical and Biologically-Active Compounds Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran 16846-13114, Iran

     Tetrabutylammonium phthalimide-N-oxyl (TBAPINO) was found to be an effective organocatalyst for rapid, simple and chemoselective protection of the hydroxyl group of alcohols and phenols using hexamethyldisilazane (HMDS) under mild conditions. The low catalyst loading, high to quantitative yields and simple removal of the catalyst from the reaction mixture illustrate the other attractive features of this protocol.

Keywords: Trimethylsilylation, Alcohols, Phenols, Hexamethyldisilazane, Tetrabutylammonium phthalimide-N-oxyl, Organocatalysis