The Heck reaction at a silica surface. Functionalisation of simple organo-modified silicas

Abstract

The Heck reaction has been shown to be a useful method for the functionalisation of simple organically modified silica. Four organically modified silicas, representing four preparative routes, were further modified by Heck coupling of aryl halides and alkenes. The reaction proceeds at temperatures of 120–150 °C, and functions best in the absence of solvent. Triethylamine is favoured over inorganic bases, and leads to good conversions. The reaction is particularly effective when the surface-bound species is the alkene coupling partner.