Graphene oxide-bound electron-deficient tin(IV) porphyrin: a highly efficient and selective catalyst for trimethylsilylation of alcohols and phenols with hexamethyldisilazane

The catalytic activity of graphene oxide-bound tetrakis(p-aminophenyl) porphyrinatotin (IV) trifluoromethanesulfonate, [SnIV(TNH2PP)(OTf)(2)], in the trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) is reported. The prepared catalyst was characterized using inductively coupled plasma analysis, scanning electron microscopy, transmission electron microscopy, and Fourier transform infrared and diffuse reflectance UV-visible spectroscopies. This heterogeneous catalyst was used for selective trimethylsilylation of various alcohols and phenols with HMDS in short reaction times and high yields. Also, the catalyst is of high reusability and stability, in that it was recovered several times without loss of its initial activity. The chemoselectivity of this catalytic system in the silylation of primary alcohols in the presence of secondary and tertiary alcohols and also phenols was investigated.