One-pot esterification-click (CuAAC) and esterification-acetylene coupling (Glaser/Eglinton) for functionalization of Wang polystyrene resin

We report three new sets of one-pot reactions for functionalization of Wang polystyrene resin and its derivatives. We first show that it is possible to combine esterification and CuAAC (Copper-Catalyzed Alkyne-Azide Cycloaddition) in a one-pot reaction with a very high yield. We also demonstrate for the first time that it is possible to combine esterification with either Glaser or Eglinton acetylene-couplings in a one-pot reaction. Finally, we show that the esterification, CuAAC, and Glaser-coupling reactions are all compatible with each other, and it is possible to run in parallel esterification/CuAAC and esterification/Glaser coupling in a single vessel. All reactions are performed at room temperature while the only separation method required is filtering and washing the resin.