Solid-Phase Synthesis of Unfunctionalized Arenes Via the Traceless Cleavage of Sulfonate Linkers

Abstract

The hydrogenolysis of polymer-bound arenesulfonates by 2-propylmagnesium chloride was performed through reductive cleavage of the C-S bond in the presence of a nickel catalyst. The reaction underwent in the highest efficiency by adding 15 equiv of the nucleophile in two additions with dppfNiCl(2) in THF. Various unfunctionalized naphthalene, biphenyl, and stilbene derivatives were produced in good yields by the traceless sulfonate linker system at room temperature.