Synthesis of polymeric supports with spacer-modified triazene linkers: aldol and Grignard reactions of immobilized nortropinone

Four new polymeric supports with 3- and 6-carbon atom spacers and triazene linkers derived from meta- and para-aminophenol were synthesized from commercial Merrifield polymer. The supports could be used for immobilization of secondary amines in SPOS. A new strategy based on the use of diethylamine triazenes as masked precursors for the generation of polymer-supported diazonium ions was used. The performance of the new linkers was tested on Grignard and aldol reactions of solid-phase immobilized nortropinone. The new supports with C3-T2 linkers gave products with better yields and purities than the classical T2 supports or the supports with the C6-T2 linkers.