Living cascade enyne metathesis polymerization of an allylic acetate monomer and post-polymerization modification via a Tsuji–Trost reaction†

Here we report the design and synthesis of an allylic acetate-containing monomer suitable for post-polymerization modification through a Tsuji–Trost reaction. This monomer is capable of living cascade enyne metathesis polymerization, as evidenced by the kinetics studies as well as a diblock copolymer formation. The resultant polymers are amenable to efficient palladium-catalyzed Tsuji–Trost reactions using a range of nitrogen, oxygen, and sulfur nucleophiles to furnish structural elaboration. Additionally, the pristine and modified polymers possessed acid-responsive degradability and further tunability depending on the structure.