Polymer-supported syntheses of thiophene-containing compounds using a new type of traceless linker

Abstract

A new type of traceless linker is described for use in polymer-supported (PS) syntheses of thiophene-containing compounds. It is based on the cleavage of PS aryl 2-thienyl ketones by a mixture of potassium t-butoxide and water (typical mol ratio 10 : 3) in an ethereal solvent. Cleavage occurs to give the soluble thiophene-containing product. The method is used to prepare a range of eight thiophene-containing compounds including a terthiophene and a dialkylquaterthiophene. PS unsymmetrical diaryl ketones incorporating, for example, ortho-methoxyphenyl or pyrrole moieties could also serve as traceless linkers.