Electroorganic synthesis has defied application in Solid-Phase Organic Synthesis (SPOS)
so far. Typically more than 99.9% of the substrate molecules immobilized on a polymeric
support are buried in the interior of the bead, and therefore are unable to undergo
direct contact with a heterogeneous reagent such as an electrode. This intrinsic impediment
for an electrochemical reaction can be overcome by the use of a redox mediator which
shuttles electrons from the electrode to the polymer bound substrate molecules. This
approach of indirect electroorganic synthesis was successfully applied for the 2,5-dialkoxylation
of furans on solid phase. The oxidation products can be hydrolyzed and through condensation
with hydrazine hydrate substituted pyridazines are produced in 50-65% overall yield.
combinatorial chemistry - electrochemistry - furans - heterocycles - solid-phase synthesis
